Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8da2071d-5e2f-43da-9bb1-2c7b30c078af","title":"High Growth Enterprise Account Executive","department":"Sales","team":"Sales","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-07-16T04:01:12.707+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8da2071d-5e2f-43da-9bb1-2c7b30c078af","applyUrl":"https://jobs.ashbyhq.com/sierra/8da2071d-5e2f-43da-9bb1-2c7b30c078af/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting and Lead Generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our Commercial customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage Relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our customers. Serve as the primary point of contact for commercial clients, ensuring high levels of customer satisfaction.
Negotiating and Closing Complex Deal Cycles: Lead negotiations with existing customers and prospective clients, addressing objections and closing deals. Ensure all contracts and agreements are completed accurately and in a timely manner. Work closely with legal and finance teams to finalize terms and conditions.
Sales Strategy and Planning: Develop and execute sales strategies to meet or exceed sales targets. Create tailored sales presentations and proposals to address the specific needs of enterprise clients. Collaborate with the marketing team to develop and implement effective sales campaigns and presentations.
Help Define our Sales Motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds!
Collaborate Cross-Functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Market Analysis: Conduct market research to identify new business opportunities.
5-7+ years of experience in a customer-facing sales role, either with Mid-market or SMB accounts.
Strong Communication Skills: Exceptional verbal and written communication abilities.
Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting and Lead Generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our Commercial customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage Relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our customers. Serve as the primary point of contact for commercial clients, ensuring high levels of customer satisfaction.\n\n - Negotiating and Closing Complex Deal Cycles: Lead negotiations with existing customers and prospective clients, addressing objections and closing deals. Ensure all contracts and agreements are completed accurately and in a timely manner. Work closely with legal and finance teams to finalize terms and conditions.\n\n - Sales Strategy and Planning: Develop and execute sales strategies to meet or exceed sales targets. Create tailored sales presentations and proposals to address the specific needs of enterprise clients. Collaborate with the marketing team to develop and implement effective sales campaigns and presentations.\n\n - Help Define our Sales Motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds!\n\n - Collaborate Cross-Functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Market Analysis: Conduct market research to identify new business opportunities.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years of experience in a customer-facing sales role, either with Mid-market or SMB accounts.\n\n - Strong Communication Skills: Exceptional verbal and written communication abilities.\n\n - Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"41e66706-b647-4ab1-8c7f-8f2975babba7","title":"Enterprise Sales Director - Majors","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-22T02:47:27.634+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/41e66706-b647-4ab1-8c7f-8f2975babba7","applyUrl":"https://jobs.ashbyhq.com/sierra/41e66706-b647-4ab1-8c7f-8f2975babba7/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d77487f9-bab3-44c6-be18-744e7125c8b3","title":"Software Engineer, Platform","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2024-08-28T22:10:59.372+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d77487f9-bab3-44c6-be18-744e7125c8b3","applyUrl":"https://jobs.ashbyhq.com/sierra/d77487f9-bab3-44c6-be18-744e7125c8b3/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Sierra’s platform. At Sierra, we believe agent development is an evolution of software development that requires new tools and systems. You will work on the platform primitives that power how agents are built, orchestrated, and deployed.
Invent the foundations of agent development. You’ll design systems that enable engineers and customers to build reliable, steerable agents, including runtime systems, developer tooling, and internal infrastructure.
Enable engineers to move faster. You’ll build tools and workflows that accelerate how engineers build and deploy agents across Sierra.
A passion for being on the frontier of AI products.
Pride in building reliable, maintainable, and secure systems that scale.
Motivation and high-agency to drive outcomes in a high-autonomy culture.
4+ years hands-on experience building production systems.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building developer platforms or SDKs.
Experience working on distributed systems.
Experience building AI-powered products.
Leadership experience on technical projects.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Sierra’s platform. At Sierra, we believe agent development is an evolution of software development that requires new tools and systems. You will work on the platform primitives that power how agents are built, orchestrated, and deployed.\n\n - Invent the foundations of agent development. You’ll design systems that enable engineers and customers to build reliable, steerable agents, including runtime systems, developer tooling, and internal infrastructure.\n\n - Enable engineers to move faster. You’ll build tools and workflows that accelerate how engineers build and deploy agents across Sierra.\n\n\nWHAT YOU'LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Pride in building reliable, maintainable, and secure systems that scale.\n\n - Motivation and high-agency to drive outcomes in a high-autonomy culture.\n\n - 4+ years hands-on experience building production systems.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER\n\n - Experience building developer platforms or SDKs.\n\n - Experience working on distributed systems.\n\n - Experience building AI-powered products.\n\n - Leadership experience on technical projects.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"effd7cd2-8a28-4bae-a3b8-40720ba09717","title":"Product Manager, Agent Development","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-03-12T17:39:46.539+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/effd7cd2-8a28-4bae-a3b8-40720ba09717","applyUrl":"https://jobs.ashbyhq.com/sierra/effd7cd2-8a28-4bae-a3b8-40720ba09717/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9501ffa2-b433-4f51-b7f0-d8e53e37442d","title":"Enterprise Sales Director, Europe","department":"Sales","team":"Sales","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-04-11T23:09:39.816+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9501ffa2-b433-4f51-b7f0-d8e53e37442d","applyUrl":"https://jobs.ashbyhq.com/sierra/9501ffa2-b433-4f51-b7f0-d8e53e37442d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b7d1dbcd-ca72-472f-b15e-5b4b0f886be0","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-02-13T20:44:17.436+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b7d1dbcd-ca72-472f-b15e-5b4b0f886be0","applyUrl":"https://jobs.ashbyhq.com/sierra/b7d1dbcd-ca72-472f-b15e-5b4b0f886be0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ba780c1d-ebd7-45b8-8c99-12666af5bfa3","title":"Product Designer","department":"Product Design","team":"Product Design","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-05-15T23:00:57.287+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ba780c1d-ebd7-45b8-8c99-12666af5bfa3","applyUrl":"https://jobs.ashbyhq.com/sierra/ba780c1d-ebd7-45b8-8c99-12666af5bfa3/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Solve for the customer: We serve multiple stakeholders – People looking for help from our Agents via chat & voice, CX managers using our tools to monitor and improve the process, and Developers looking to build on and extend our platform. Each of these has a unique set of needs and product challenges.
Innovate: AI Agents represent a new frontier. Discovering new tools and processes for building agents will be among the defining characteristics of the next generation of companies.
End-to-End Ownership: Drive the entire design process from concept to execution to iteration, in close collaboration with cross-functional partners.
Collaborate Across Teams: Partner closely engineering, product, leadership, and the entire company to define and build a seamless and cohesive experience.
Gather Feedback: Get your hand dirty with customer feedback and usability testing to gather insights and iterate to ensure we solve user problems effectively.
Build Design Systems: Develop and maintain a scalable design system that ensures consistency and efficiency across all products and platforms.
Proven Experience: Extensive experience in UI/UX design, with background leading design projects from ideation to launch.
Curiosity: Passion for deeply understanding user needs and finding the right solutions from first principles.
Full-Stack Design: Visual design is the baseline. You should be fluent in creating beautiful, high-quality designs—working end-to-end from shaping product direction to defining the right interactions and ensuring every pixel is crafted with care.
Great Collaboration: Design is a team sport, and building great products means working closely with product, engineering, and leadership to help bring ideas to life.
Excellent Communication: Strong verbal and written communication skills, with the ability to articulate problems, design concepts and decisions to various stakeholders.
Research Skills: Experience gathering customer feedback, usability testing, and translating findings into actionable design improvements.
Technical Proficiency: Mastery of Figma, along with classics like Photoshop and Illustrator. Strong ability to prototype—whether in Figma, Principal, or code—quickly and effectively.
Adaptability and Resilience: Comfort working in a fast-paced startup environment, able to adapt to changing priorities and handle ambiguity with grace.
Experience designing for AI-driven products or conversational interfaces.
Experience working on developer-driven products, including SDKs, APIs, and technical tooling.
Experience with Typescript, React, and other programming languages.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO:\n\n - Solve for the customer: We serve multiple stakeholders – People looking for help from our Agents via chat & voice, CX managers using our tools to monitor and improve the process, and Developers looking to build on and extend our platform. Each of these has a unique set of needs and product challenges.\n\n - Innovate: AI Agents represent a new frontier. Discovering new tools and processes for building agents will be among the defining characteristics of the next generation of companies.\n\n - End-to-End Ownership: Drive the entire design process from concept to execution to iteration, in close collaboration with cross-functional partners.\n\n - Collaborate Across Teams: Partner closely engineering, product, leadership, and the entire company to define and build a seamless and cohesive experience. \n\n - Gather Feedback: Get your hand dirty with customer feedback and usability testing to gather insights and iterate to ensure we solve user problems effectively.\n\n - Build Design Systems: Develop and maintain a scalable design system that ensures consistency and efficiency across all products and platforms.\n\n\nWHAT YOU'LL BRING:\n\n - Proven Experience: Extensive experience in UI/UX design, with background leading design projects from ideation to launch.\n\n - Curiosity: Passion for deeply understanding user needs and finding the right solutions from first principles. \n\n - Full-Stack Design: Visual design is the baseline. You should be fluent in creating beautiful, high-quality designs—working end-to-end from shaping product direction to defining the right interactions and ensuring every pixel is crafted with care.\n\n - Great Collaboration: Design is a team sport, and building great products means working closely with product, engineering, and leadership to help bring ideas to life.\n\n - Excellent Communication: Strong verbal and written communication skills, with the ability to articulate problems, design concepts and decisions to various stakeholders.\n\n - Research Skills: Experience gathering customer feedback, usability testing, and translating findings into actionable design improvements.\n\n - Technical Proficiency: Mastery of Figma, along with classics like Photoshop and Illustrator. Strong ability to prototype—whether in Figma, Principal, or code—quickly and effectively.\n\n - Adaptability and Resilience: Comfort working in a fast-paced startup environment, able to adapt to changing priorities and handle ambiguity with grace.\n\n\nEVEN BETTER...\n\n - Experience designing for AI-driven products or conversational interfaces.\n\n - Experience working on developer-driven products, including SDKs, APIs, and technical tooling.\n\n - Experience with Typescript, React, and other programming languages.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"fed8ca9a-0bb7-44ef-a541-0be6a8ae7bba","title":"Product Manager, Agent Development (German speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:29:19.304+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/fed8ca9a-0bb7-44ef-a541-0be6a8ae7bba","applyUrl":"https://jobs.ashbyhq.com/sierra/fed8ca9a-0bb7-44ef-a541-0be6a8ae7bba/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Professional fluency in both German and English.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Professional fluency in both German and English.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"e9f5fdb6-91ee-4c55-9230-41ec8865650e","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2025-04-18T20:23:18.804+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/e9f5fdb6-91ee-4c55-9230-41ec8865650e","applyUrl":"https://jobs.ashbyhq.com/sierra/e9f5fdb6-91ee-4c55-9230-41ec8865650e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ddae4a0c-2f6c-4cc3-80aa-da74a0dd667a","title":"Research Engineer, Applied Research","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-05T23:31:01.724+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ddae4a0c-2f6c-4cc3-80aa-da74a0dd667a","applyUrl":"https://jobs.ashbyhq.com/sierra/ddae4a0c-2f6c-4cc3-80aa-da74a0dd667a/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra’s Applied Research team advances the quality, speed, and cost efficiency of the models powering our agents across a wide range of tasks. Our work spans post-training open-weight models for specialized capabilities and pioneering new approaches to voice AI, turning research breakthroughs into reliable production systems.
Tackle unsolved applied AI and ML problems. Pushing the boundaries of post-training, voice AI, and long-horizon task execution, building agents that can reason, adapt, and reliably carry out complex tasks for customers.
Determine when to build specialized models and when to use externally provided frontier intelligence, balancing quality, speed, and cost to deliver customer value.
Turn ambiguous product and customer problems into well-framed machine learning problems.
Develop, fine-tune, evaluate, and deploy models that improve Sierra’s customer-facing AI agents.
Advance our post-training work, from supervised fine-tuning toward reinforcement learning and long-horizon optimization.
Build rigorous evaluations that connect model performance to real-world agent quality.
Work with large-scale, proprietary datasets spanning text and audio interactions.
Collaborate across Sierra while taking ideas from experimentation through production deployment and customer impact.
Strong experience building and deploying production machine learning and AI systems. We welcome backgrounds across applied ML, including search, ranking, recommendations, advertising, language, and speech.
Excellent judgment in framing product problems as ML tasks and selecting the simplest & most effective approach.
Experience working deeply with data, experimentation, evaluation, and model iteration.
A practical, evidence-driven approach to ML, with strong judgement around when a problem calls for modeling and when a simpler solution will deliver the best outcome.
The ability to operate with high agency and work across the stack when needed to deliver an outcome.
Alignment with Sierra’s values, including Craftsmanship, Customer Obsession, and Competitive Intensity.
A degree in computer science, machine learning, or a related field, or equivalent professional experience.
Experience with supervised fine-tuning or reinforcement learning.
Experience in search, ranking, recommendations, or advertising systems.
Experience training and deploying language, speech, or multimodal models.
Experience designing model evaluations tied to real-world product outcomes.
Experience working with large-scale consumer datasets or high-volume ML products.
Contributions to applied ML research or benchmarks.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nSierra’s Applied Research team advances the quality, speed, and cost efficiency of the models powering our agents across a wide range of tasks. Our work spans post-training open-weight models for specialized capabilities and pioneering new approaches to voice AI, turning research breakthroughs into reliable production systems.\n\n\n\n\nWHAT YOU’LL DO\n\n - Tackle unsolved applied AI and ML problems. Pushing the boundaries of post-training, voice AI, and long-horizon task execution, building agents that can reason, adapt, and reliably carry out complex tasks for customers.\n\n - Determine when to build specialized models and when to use externally provided frontier intelligence, balancing quality, speed, and cost to deliver customer value.\n\n - Turn ambiguous product and customer problems into well-framed machine learning problems.\n\n - Develop, fine-tune, evaluate, and deploy models that improve Sierra’s customer-facing AI agents.\n\n - Advance our post-training work, from supervised fine-tuning toward reinforcement learning and long-horizon optimization.\n\n - Build rigorous evaluations that connect model performance to real-world agent quality.\n\n - Work with large-scale, proprietary datasets spanning text and audio interactions.\n\n - Collaborate across Sierra while taking ideas from experimentation through production deployment and customer impact.\n\n\n\n\nWHAT YOU’LL BRING\n\n - Strong experience building and deploying production machine learning and AI systems. We welcome backgrounds across applied ML, including search, ranking, recommendations, advertising, language, and speech.\n\n - Excellent judgment in framing product problems as ML tasks and selecting the simplest & most effective approach.\n\n - Experience working deeply with data, experimentation, evaluation, and model iteration.\n\n - A practical, evidence-driven approach to ML, with strong judgement around when a problem calls for modeling and when a simpler solution will deliver the best outcome.\n\n - The ability to operate with high agency and work across the stack when needed to deliver an outcome.\n\n - Alignment with Sierra’s values, including Craftsmanship, Customer Obsession, and Competitive Intensity.\n\n - A degree in computer science, machine learning, or a related field, or equivalent professional experience.\n\n\nEVEN BETTER…\n\n - Experience with supervised fine-tuning or reinforcement learning.\n\n - Experience in search, ranking, recommendations, or advertising systems.\n\n - Experience training and deploying language, speech, or multimodal models.\n\n - Experience designing model evaluations tied to real-world product outcomes.\n\n - Experience working with large-scale consumer datasets or high-volume ML products.\n\n - Contributions to applied ML research or benchmarks.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b4b762e6-8ce7-4ea7-b9b3-40c04f62135a","title":"Product Manager, Agent Development","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-04-08T21:29:16.254+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b4b762e6-8ce7-4ea7-b9b3-40c04f62135a","applyUrl":"https://jobs.ashbyhq.com/sierra/b4b762e6-8ce7-4ea7-b9b3-40c04f62135a/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b3829801-8e0b-4047-8cd8-8a51c87028fd","title":"Software Engineer, Agent Runtime","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-03-27T02:59:29.568+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b3829801-8e0b-4047-8cd8-8a51c87028fd","applyUrl":"https://jobs.ashbyhq.com/sierra/b3829801-8e0b-4047-8cd8-8a51c87028fd/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build the core systems that power agents. You’ll work on the Agent SDK — the orchestration engine, runtime, and primitives that define how agents reason, take actions, and interact with users and systems.
Design the agentic loop. What primitives do we need to build agents that are steerable and verifiable, while still conversational and adaptive? You’ll help define how agents operate in real-world environments.
Improve retrieval and grounding. You’ll build systems that ensure agents provide accurate, trustworthy responses by effectively retrieving and using knowledge.
Build evaluation systems. You’ll design frameworks that allow us and our customers to measure and improve agent quality over time.
A passion for being on the frontier of AI products.
Strong software engineering fundamentals and experience building production systems.
Motivation and high-agency to drive outcomes in a high-autonomy culture.
4+ years hands-on experience building production products and systems.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building AI-powered systems or agent frameworks.
Experience with retrieval, evaluation systems, or LLM-based applications.
Experience building developer platforms or SDKs.
Experience with Go and Typescript.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build the core systems that power agents. You’ll work on the Agent SDK — the orchestration engine, runtime, and primitives that define how agents reason, take actions, and interact with users and systems.\n\n - Design the agentic loop. What primitives do we need to build agents that are steerable and verifiable, while still conversational and adaptive? You’ll help define how agents operate in real-world environments.\n\n - Improve retrieval and grounding. You’ll build systems that ensure agents provide accurate, trustworthy responses by effectively retrieving and using knowledge.\n\n - Build evaluation systems. You’ll design frameworks that allow us and our customers to measure and improve agent quality over time.\n\n\nWHAT YOU'LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Strong software engineering fundamentals and experience building production systems.\n\n - Motivation and high-agency to drive outcomes in a high-autonomy culture.\n\n - 4+ years hands-on experience building production products and systems.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER\n\n - Experience building AI-powered systems or agent frameworks.\n\n - Experience with retrieval, evaluation systems, or LLM-based applications.\n\n - Experience building developer platforms or SDKs.\n\n - Experience with Go and Typescript.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"bbef339c-3365-40df-804b-ece245386b43","title":"Security Engineer","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2025-04-30T04:19:10.982+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/bbef339c-3365-40df-804b-ece245386b43","applyUrl":"https://jobs.ashbyhq.com/sierra/bbef339c-3365-40df-804b-ece245386b43/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Security Engineering builds the foundations that let Sierra deliver powerful AI agents while protecting customer data and trust. We partner across product and platform to make security, privacy, and safety core product capabilities and secure defaults.
Our work spans several security domains. You’ll go deep where your strengths and interests are strongest, with opportunities to explore new areas alongside the team.
Build the Foundations of Trust.
Design and ship systems and controls that make Sierra secure by default — spanning product security, infrastructure security, enterprise security, identity, and detection and response. You’ll work across all layers of our platform to identify risk, strengthen architectures, and build durable defenses.
Own Cross-Cutting Systems.
Partner with product, platform, and infrastructure team to threat model designs, review code and architectures, and implement and evolve Sierra’s security primitives. You’ll make pragmatic design trade-offs between usability, performance, reliability, and security.
Find and Reduce Real Risk.
Identify vulnerabilities, investigate suspicious behavior, and improve detections and response workflows across applications, cloud infrastructure, identity, endpoints, and internal systems. Turn what you learn into systemic fixes and controls that prevent entire classes of issues.
Automate and Scale Security Workflows.
Create developer-friendly tooling to reduce risk and friction — whether through automating security checks in CI/CD, building secure paved paths, improving vulnerability discovery, or instrumenting high-signal detection and response.
Deep Security Expertise.
Strong security fundamentals and depth in at least one domain, such as product security, platform or cloud security, enterprise security, identity, detection and response, or offensive security. You can apply that expertise across unfamiliar systems and emerging threats.
Product and Platform Mindset.
You care about building secure, scalable systems that enable, not block, innovation. You work closely with teams across Sierra to make trade-offs clear and help them move quickly without sacrificing trust.
Software Engineering and Systems Thinking.
You’re comfortable reading and writing code, understanding how production systems fit together, and building pragmatic software solutions to security problems. You can reason about system design and contribute to APIs, services, and security controls, with an eye toward reliability and maintainability.
Curiosity and Ownership.
You take ambiguous, cross-cutting problems from first principles to production and go deep when needed: threat modeling a distributed system, tracing an authorization decision across services, or following an investigation from weak signal to root cause. You define the problem, align partners, build the solution, and own it in production.
You’ve worked across more than one of product security, infrastructure security, enterprise security, detection and response, or offensive security.
You’ve built security frameworks, platforms, or solutions that engineers and responders rely on to prevent, detect, investigate, and remediate security issues at scale.
You have exposure to AI systems or care about designing secure-by-default LLM applications and agentic systems.
You think like an attacker — you naturally ask “what could go wrong?” when reviewing designs or investigating systems. You’ve found or fixed real security issues in production.
You thrive in 0→1 environments, where foundational systems have to balance speed, reliability, and trust.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\n\n\nSECURITY ENGINEER\n\nSecurity Engineering builds the foundations that let Sierra deliver powerful AI agents while protecting customer data and trust. We partner across product and platform to make security, privacy, and safety core product capabilities and secure defaults.\n\n\n\n\nWHAT YOU’LL DO\n\nOur work spans several security domains. You’ll go deep where your strengths and interests are strongest, with opportunities to explore new areas alongside the team.\n\nBuild the Foundations of Trust.\nDesign and ship systems and controls that make Sierra secure by default — spanning product security, infrastructure security, enterprise security, identity, and detection and response. You’ll work across all layers of our platform to identify risk, strengthen architectures, and build durable defenses.\n\nOwn Cross-Cutting Systems.\nPartner with product, platform, and infrastructure team to threat model designs, review code and architectures, and implement and evolve Sierra’s security primitives. You’ll make pragmatic design trade-offs between usability, performance, reliability, and security.\n\nFind and Reduce Real Risk.\n\nIdentify vulnerabilities, investigate suspicious behavior, and improve detections and response workflows across applications, cloud infrastructure, identity, endpoints, and internal systems. Turn what you learn into systemic fixes and controls that prevent entire classes of issues.\n\nAutomate and Scale Security Workflows.\nCreate developer-friendly tooling to reduce risk and friction — whether through automating security checks in CI/CD, building secure paved paths, improving vulnerability discovery, or instrumenting high-signal detection and response.\n\n \n \n\n\nWHAT YOU’LL BRING\n\nDeep Security Expertise.\nStrong security fundamentals and depth in at least one domain, such as product security, platform or cloud security, enterprise security, identity, detection and response, or offensive security. You can apply that expertise across unfamiliar systems and emerging threats.\n\nProduct and Platform Mindset.\nYou care about building secure, scalable systems that enable, not block, innovation. You work closely with teams across Sierra to make trade-offs clear and help them move quickly without sacrificing trust.\n\nSoftware Engineering and Systems Thinking.\nYou’re comfortable reading and writing code, understanding how production systems fit together, and building pragmatic software solutions to security problems. You can reason about system design and contribute to APIs, services, and security controls, with an eye toward reliability and maintainability.\n\nCuriosity and Ownership.\nYou take ambiguous, cross-cutting problems from first principles to production and go deep when needed: threat modeling a distributed system, tracing an authorization decision across services, or following an investigation from weak signal to root cause. You define the problem, align partners, build the solution, and own it in production.\n\n \n \n\n\nEVEN BETTER IF…\n\n - You’ve worked across more than one of product security, infrastructure security, enterprise security, detection and response, or offensive security.\n\n - You’ve built security frameworks, platforms, or solutions that engineers and responders rely on to prevent, detect, investigate, and remediate security issues at scale.\n\n - You have exposure to AI systems or care about designing secure-by-default LLM applications and agentic systems.\n\n - You think like an attacker — you naturally ask “what could go wrong?” when reviewing designs or investigating systems. You’ve found or fixed real security issues in production.\n\n - You thrive in 0→1 environments, where foundational systems have to balance speed, reliability, and trust.\n\n\n\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ba9ca2da-c0c3-4673-b496-f820223c77c1","title":"Enterprise Sales Engineer","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-06-02T12:31:36.620+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ba9ca2da-c0c3-4673-b496-f820223c77c1","applyUrl":"https://jobs.ashbyhq.com/sierra/ba9ca2da-c0c3-4673-b496-f820223c77c1/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"66324233-f3af-496a-b43d-ebe1a6a0e2d0","title":"Product Marketing Manager","department":"Marketing & Communications","team":"Marketing","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-05T04:35:50.773+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/66324233-f3af-496a-b43d-ebe1a6a0e2d0","applyUrl":"https://jobs.ashbyhq.com/sierra/66324233-f3af-496a-b43d-ebe1a6a0e2d0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is growing fast, and product marketing sits at the center of how we go to market. You'll make sure customers and prospects understand what we build, why it matters to their industry and role, and why Sierra is the right choice. You'll own positioning, messaging, launches, sales enablement, and content, working closely with product, sales, agent development and the rest of marketing.
Shape how we tell our story. You’re a passionate product marketer, energized by messaging and positioning and skilled at building a message for a feature, product, industry or buyer. One day you may update web copy, the next you build an event session, craft a sales narrative, write a launch blog post, or create content for a campaign.
Lead product launches. When a product or new feature ships, you lead how we go to market - the messaging, the assets, and the sales enablement. Sometimes this means translating to industries or buyers.
Arm our sales team. You build and maintain the playbooks and assets our GTM teams use to sell including slide decks, landing pages, demos and more.
Build with AI-first. You’re AI fluent, and your first instinct is to self-serve and improve how you work. You’ll help build the automations, templates, and systems that keep our work consistent across industries and workstreams.
Go wide and deep. You flex across channels and activations, and you can go deep on one area, such as an industry vertical, a persona, or our web strategy. You’re comfortable with ambiguity and a fast pace, and you like to build.
4+ years of B2B or B2C product marketing experience.
Expertise in positioning and messaging, leading product or feature launches, and building sales-facing and customer-facing assets for different audiences and industries.
Strong operational instincts. You think in process, systems, and repeatable frameworks, and you’re comfortable building structure where none exists.
Fluency with tools like ChatGPT or Claude to work faster and automate where it makes sense.
A passion for storytelling and experience building presentations in Google Slides.
Comfort being on a lean team that’s still being defined, and enthusiasm for shaping how it works.
Take a new product from roadmap to launch: positioning, messaging, sales assets, enablement, and demo.
Go deep on an industry and understand how our product can help that segment, build messaging that resonates, and downstream assets.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE ROLE\n\nSierra is growing fast, and product marketing sits at the center of how we go to market. You'll make sure customers and prospects understand what we build, why it matters to their industry and role, and why Sierra is the right choice. You'll own positioning, messaging, launches, sales enablement, and content, working closely with product, sales, agent development and the rest of marketing.\n\n\n\nWHAT YOU'LL DO\n\n - Shape how we tell our story. You’re a passionate product marketer, energized by messaging and positioning and skilled at building a message for a feature, product, industry or buyer. One day you may update web copy, the next you build an event session, craft a sales narrative, write a launch blog post, or create content for a campaign.\n\n - Lead product launches. When a product or new feature ships, you lead how we go to market - the messaging, the assets, and the sales enablement. Sometimes this means translating to industries or buyers.\n\n - Arm our sales team. You build and maintain the playbooks and assets our GTM teams use to sell including slide decks, landing pages, demos and more.\n\n - Build with AI-first. You’re AI fluent, and your first instinct is to self-serve and improve how you work. You’ll help build the automations, templates, and systems that keep our work consistent across industries and workstreams.\n\n - Go wide and deep. You flex across channels and activations, and you can go deep on one area, such as an industry vertical, a persona, or our web strategy. You’re comfortable with ambiguity and a fast pace, and you like to build.\n\n\nWHAT YOU'LL BRING\n\n - 4+ years of B2B or B2C product marketing experience.\n\n - Expertise in positioning and messaging, leading product or feature launches, and building sales-facing and customer-facing assets for different audiences and industries.\n\n - Strong operational instincts. You think in process, systems, and repeatable frameworks, and you’re comfortable building structure where none exists.\n\n - Fluency with tools like ChatGPT or Claude to work faster and automate where it makes sense.\n\n - A passion for storytelling and experience building presentations in Google Slides.\n\n - Comfort being on a lean team that’s still being defined, and enthusiasm for shaping how it works.\n\n\nSAMPLE PROJECTS\n\n - Take a new product from roadmap to launch: positioning, messaging, sales assets, enablement, and demo.\n\n - Go deep on an industry and understand how our product can help that segment, build messaging that resonates, and downstream assets.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"742020b7-5a2a-495d-8ac9-d74d31dc91c6","title":"IT Infrastructure Engineer","department":"IT","team":"IT","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-21T22:53:42.780+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/742020b7-5a2a-495d-8ac9-d74d31dc91c6","applyUrl":"https://jobs.ashbyhq.com/sierra/742020b7-5a2a-495d-8ac9-d74d31dc91c6/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We’re looking for a hands-on IT Infrastructure Engineer to help scale Sierra’s internal systems during a critical period of growth. You’ll be the second member of our IT Engineering team, partnering closely with our IT Lead, GRC Lead, and Platform Engineering team to build and operate the systems that support our company day-to-day.
This is an engineering-first role. Our team approaches IT the same way product engineering teams build software: through code, automation, and well-designed systems. We build internal tools, ship integrations, and operate CI/CD-style workflows to manage identity, security, and infrastructure at scale.
This is a foundational role with significant ownership. You’ll help design and implement core infrastructure, strengthen security controls, and improve how we operate internally. The right person enjoys building high-leverage systems, automating repetitive work, and creating well-documented, scalable solutions that make the entire company more effective.
In your first few months, you’ll focus on:
Iterating on and improving internal tools that power IT and security workflows
Deploying a DLP solution and integrating it into automated enforcement pipelines
Building API-driven integrations between internal systems and our compliance automation platform
More broadly, you will:
Design and scale internal infrastructure using code and infrastructure-as-code practices
Build and maintain internal tools and services
Improve and develop automation pipelines for provisioning, access management, and security controls
Treat IT systems like software: versioned, tested, and continuously improved
Partner with Platform Engineering and Security to implement scalable, programmatic solutions
Create clear, durable documentation to support long-term scalability
Think of IT problems as engineering problems, and default to building over manual work
Have strong experience with identity platforms (Okta, Google Workspace, SSO, MFA, SCIM, OIDC)
Have deployed or managed DLP or related security solutions (e.g., ZTNA, Cloudflare)
Have extensive experience with IaC (Terraform)
Are comfortable writing code for automation (e.g., Python, Bash, or similar)
Have experience building internal tools or services that integrate via APIs
Are comfortable working with CI/CD concepts and automation pipelines
Are fluent in using and administering modern AI tooling
Understand SaaS lifecycle management and compliance requirements
Communicate clearly and document your systems well
Are comfortable operating independently in a fast-moving environment
Background in software engineering or prior experience on a product engineering team
Experience building internal platforms or developer tooling
Familiarity with security tooling such as CASB, EDR, or MDM
Experience with access audits, data residency, or compliance controls
Experience deploying systems using AWS and infrastructure-as-code
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nWe’re looking for a hands-on IT Infrastructure Engineer to help scale Sierra’s internal systems during a critical period of growth. You’ll be the second member of our IT Engineering team, partnering closely with our IT Lead, GRC Lead, and Platform Engineering team to build and operate the systems that support our company day-to-day.\n\nThis is an engineering-first role. Our team approaches IT the same way product engineering teams build software: through code, automation, and well-designed systems. We build internal tools, ship integrations, and operate CI/CD-style workflows to manage identity, security, and infrastructure at scale.\n\nThis is a foundational role with significant ownership. You’ll help design and implement core infrastructure, strengthen security controls, and improve how we operate internally. The right person enjoys building high-leverage systems, automating repetitive work, and creating well-documented, scalable solutions that make the entire company more effective.\n\n\nWHAT YOU'LL DO\n\nIn your first few months, you’ll focus on:\n\n - Iterating on and improving internal tools that power IT and security workflows\n\n - Deploying a DLP solution and integrating it into automated enforcement pipelines\n\n - Building API-driven integrations between internal systems and our compliance automation platform\n\nMore broadly, you will:\n\n - Design and scale internal infrastructure using code and infrastructure-as-code practices\n\n - Build and maintain internal tools and services\n\n - Improve and develop automation pipelines for provisioning, access management, and security controls\n\n - Treat IT systems like software: versioned, tested, and continuously improved\n\n - Partner with Platform Engineering and Security to implement scalable, programmatic solutions\n\n - Create clear, durable documentation to support long-term scalability\n\n\nWHAT YOU’LL BRING\n\n - Think of IT problems as engineering problems, and default to building over manual work\n\n - Have strong experience with identity platforms (Okta, Google Workspace, SSO, MFA, SCIM, OIDC)\n\n - Have deployed or managed DLP or related security solutions (e.g., ZTNA, Cloudflare)\n\n - Have extensive experience with IaC (Terraform)\n\n - Are comfortable writing code for automation (e.g., Python, Bash, or similar)\n\n - Have experience building internal tools or services that integrate via APIs\n\n - Are comfortable working with CI/CD concepts and automation pipelines\n\n - Are fluent in using and administering modern AI tooling\n\n - Understand SaaS lifecycle management and compliance requirements\n\n - Communicate clearly and document your systems well\n\n - Are comfortable operating independently in a fast-moving environment\n\n\nEVEN BETTER...\n\n - Background in software engineering or prior experience on a product engineering team\n\n - Experience building internal platforms or developer tooling\n\n - Familiarity with security tooling such as CASB, EDR, or MDM\n\n - Experience with access audits, data residency, or compliance controls\n\n - Experience deploying systems using AWS and infrastructure-as-code\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"6c3fb4c1-e6ba-4e47-8d02-93ea89e75619","title":"Event Marketer","department":"Marketing & Communications","team":"Marketing","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-07-08T03:59:29.203+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/6c3fb4c1-e6ba-4e47-8d02-93ea89e75619","applyUrl":"https://jobs.ashbyhq.com/sierra/6c3fb4c1-e6ba-4e47-8d02-93ea89e75619/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build the third-party event portfolio: Own Sierra's strategy for industry conferences and sponsorships across our key verticals. Decide where we show up and why—evaluating each opportunity against pipeline goals, audience fit, and brand impact—and shape a portfolio of third-party events that builds our presence in the industries that matter most.
Program high-impact event experiences: Design the formats that drive real conversations with enterprise buyers—executive roundtables, panels, fireside chats, dinners, and field events—and define the content and messaging behind them. Develop our booth content and on-site narrative so every touchpoint reflects our brand and clearly tells the Sierra story.
Own sales enablement for events: Partner closely with Sales to make events a true pipeline engine. Build the pre-event targeting and outreach, equip the field with talk tracks and materials, and develop the post-event templates, follow-up sequences, and handoff motions that turn conversations into meetings and opportunities.
Think in integrated campaigns: Treat events as one channel in a larger story rather than standalone moments. Connect each event to the broader marketing campaign—content, demand gen, social, and ABM—so our presence builds toward a coherent narrative and compounding results.
Measure and iterate: Track event performance, gather attendee and sales feedback, and turn it into reusable playbooks. Compile post-event reporting that captures what worked, what didn't, and how we make the next program sharper.
5+ years of event marketing experience planning and executing corporate events, ideally in-house, though agency experience will also be considered.
A strategic track record building event programs that drive measurable pipeline—not just well-run logistics, but a clear point of view on which events to invest in and why.
Experience designing and programming event formats (roundtables, panels, fireside chats, field events) and developing the content and messaging that make them land with senior audiences.
A strong partnership instinct with Sales: you understand how events feed pipeline and can build the targeting, outreach, enablement, and follow-up that convert attendees into opportunities.
Demonstrated ability to manage producers, agencies, vendors, and conference/sponsorship relationships—directing execution to a high bar without owning every logistical detail yourself.
Exceptional organizational skills and meticulous attention to detail, with the ability to juggle multiple events, timelines, and partners at once without missing a beat.
Strong communication and teamwork skills, with the ability to articulate plans, campaign logic, and post-event insights to all levels of the organization.
Enthusiasm for managing events nationwide or internationally, with the flexibility to accommodate a dynamic event calendar that requires regular travel.
Integrated campaign experience: A history of connecting events to broader demand gen, content, and ABM programs so they reinforce a single, compounding narrative.
Enterprise and field marketing experience: Familiarity with creating targeted, high-impact initiatives designed specifically for enterprise customers, aligned closely with sales teams and strategic business objectives.
A proactive attitude: Ability to thrive in a fast-paced environment with high expectations. You are resourceful and calm under pressure, willing to roll up your sleeves and solve challenges on the fly.
Passion for Sierra's mission and brand: A creative flair for designing event experiences that embody our values and leave a lasting impression. You take pride in building an events portfolio that showcases Sierra's innovation and company values.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Build the third-party event portfolio: Own Sierra's strategy for industry conferences and sponsorships across our key verticals. Decide where we show up and why—evaluating each opportunity against pipeline goals, audience fit, and brand impact—and shape a portfolio of third-party events that builds our presence in the industries that matter most.\n\n - Program high-impact event experiences: Design the formats that drive real conversations with enterprise buyers—executive roundtables, panels, fireside chats, dinners, and field events—and define the content and messaging behind them. Develop our booth content and on-site narrative so every touchpoint reflects our brand and clearly tells the Sierra story.\n\n - Own sales enablement for events: Partner closely with Sales to make events a true pipeline engine. Build the pre-event targeting and outreach, equip the field with talk tracks and materials, and develop the post-event templates, follow-up sequences, and handoff motions that turn conversations into meetings and opportunities.\n\n - Think in integrated campaigns: Treat events as one channel in a larger story rather than standalone moments. Connect each event to the broader marketing campaign—content, demand gen, social, and ABM—so our presence builds toward a coherent narrative and compounding results.\n\n - Measure and iterate: Track event performance, gather attendee and sales feedback, and turn it into reusable playbooks. Compile post-event reporting that captures what worked, what didn't, and how we make the next program sharper.\n\n\nWHAT YOU’LL BRING\n\n - 5+ years of event marketing experience planning and executing corporate events, ideally in-house, though agency experience will also be considered.\n\n - A strategic track record building event programs that drive measurable pipeline—not just well-run logistics, but a clear point of view on which events to invest in and why.\n\n - Experience designing and programming event formats (roundtables, panels, fireside chats, field events) and developing the content and messaging that make them land with senior audiences.\n\n - A strong partnership instinct with Sales: you understand how events feed pipeline and can build the targeting, outreach, enablement, and follow-up that convert attendees into opportunities.\n\n - Demonstrated ability to manage producers, agencies, vendors, and conference/sponsorship relationships—directing execution to a high bar without owning every logistical detail yourself.\n\n - Exceptional organizational skills and meticulous attention to detail, with the ability to juggle multiple events, timelines, and partners at once without missing a beat.\n\n - Strong communication and teamwork skills, with the ability to articulate plans, campaign logic, and post-event insights to all levels of the organization.\n\n - Enthusiasm for managing events nationwide or internationally, with the flexibility to accommodate a dynamic event calendar that requires regular travel.\n\n\nEVEN BETTER…\n\n - Integrated campaign experience: A history of connecting events to broader demand gen, content, and ABM programs so they reinforce a single, compounding narrative.\n\n - Enterprise and field marketing experience: Familiarity with creating targeted, high-impact initiatives designed specifically for enterprise customers, aligned closely with sales teams and strategic business objectives.\n\n - A proactive attitude: Ability to thrive in a fast-paced environment with high expectations. You are resourceful and calm under pressure, willing to roll up your sleeves and solve challenges on the fly.\n\n - Passion for Sierra's mission and brand: A creative flair for designing event experiences that embody our values and leave a lasting impression. You take pride in building an events portfolio that showcases Sierra's innovation and company values.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f391b10c-7a4a-42b4-9887-dd32b31d6e4e","title":"Software Engineer, Frontend","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2025-06-04T04:50:18.696+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f391b10c-7a4a-42b4-9887-dd32b31d6e4e","applyUrl":"https://jobs.ashbyhq.com/sierra/f391b10c-7a4a-42b4-9887-dd32b31d6e4e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own frontend across product and marketing surfaces: You will work across both our core product interface and customer-facing web pages, ensuring a cohesive, polished user experience across all touch points. This includes building features in the web app and also collaborating on our website to keep branding and user experience consistent and high-quality.
Lead design system and UI components: You’ll design, build, and maintain a scalable design system and reusable component library that empowers all our engineers and designers. By delivering robust, high-quality UI components and infrastructure, you will ensure consistency and excellence across all product surfaces. You’ll also collaborate with designers to establish guidelines and patterns, enabling the team to rapidly build beautiful, consistent UIs with confidence.
Craft pixel-perfect user experiences: Work closely with our design team to translate Figma designs into reality with pixel-perfect precision and delightful interactions. You will partner with designers to refine UI patterns and ensure every detail is right – from typography and spacing to motion and hover states. We care deeply about design craft, so you’ll sweat the details to build an interface that feels elegant, intuitive, and “just right” for users.
Champion frontend excellence: As the senior frontend expert, you will set and uphold high standards for performance, accessibility, and code quality. You’ll optimize our frontend for speed (efficient loading, bundle size, smooth rendering) and ensure our product works flawlessly across browsers and devices. You will also incorporate best practices for accessibility and internationalization, making our product usable by all customers.
Move fast with pragmatism and quality: In our startup environment, you’ll iterate quickly to ship improvements and new features. You’ll make thoughtful engineering trade-offs that balance rapid delivery with maintainability and polish. This means knowing when to build a quick solution and when to invest in the long-term path – always keeping user experience and business impact in mind.
Full-stack involvement: While your focus will be frontend, you should be comfortable venturing into the backend when needed. You’ll integrate frontend features with our GraphQL API and occasionally update server-side code (we use Go/gqlgen) to unblock frontend work. In short, you’ll do what it takes across the stack to deliver a great end-to-end product experience – without ever sacrificing our high bar for UI quality.
Frontend expertise and modern skills: Extensive experience (5+ years) building world-class web interfaces using React, TypeScript, HTML and CSS. You have a proven track record of shipping polished user interfaces in production products . Bonus points if you’ve worked with Tailwind or similar modern CSS frameworks for rapid development.
Design sense and attention to detail: You have a keen eye for good design and care deeply about the details of the user experience. We look for people who share our passion for software craftsmanship and getting even the smallest details right—this aligns with Sierra’s value of craftsmanship. You take pride in creating pixel-perfect, intuitive UIs and will proactively fix even minor UI issues because you value quality.
Strong collaboration and communication: You excel at working closely with designers and product managers to achieve the best outcome. You partner with product and design teams to craft beautiful user experiences , and you communicate clearly about tradeoffs and solutions. You’re open to feedback and can articulate your ideas in discussions, ensuring everyone is on the same page.
Self-motivation and drive: You are intensely goal-oriented and proactive, able to take ownership of projects with minimal guidance. You’ve thrived in fast-paced environments and have a track record of delivering projects quickly and frequently. You can manage ambiguity and complexity, breaking down big problems into simple, workable solutions. In short, you get things done with speed and quality in equal measure.
Pragmatic problem-solving: You approach engineering with practicality. You make effective trade-offs between ideal solutions and pragmatic deliverables, always considering the user impact and long-term maintainability. You’re not ideological about technology – you choose the best tool for the job and can learn new technologies on the fly as needed.
Front-to-back understanding: While specializing in frontend, you have a solid understanding of backend fundamentals. You know how web APIs, databases, and servers work. If needed, you can read and write server-side code. In particular, experience with GraphQL APIs and/or Golang (our backend language) is a plus for this role.
Design systems experience: Previous experience building or contributing to design systems or component libraries – either at a company or in open-source—would be a big plus . This means you’ve helped create shared UI frameworks with Figma.
UI/UX specialization: An eye for user experience beyond coding —e.g. some experience with user research, visual design, or interaction design—would help you excel in crafting a delightful product. If you’ve worked closely with UX designers or have design skills yourself, that’s a bonus.
Domain experience: Exposure to AI or ML products, especially building UIs for complex data or AI-driven features. For example, if you’ve built chat interfaces, analytics dashboards, or enterprise SaaS products before, you’ll have useful relevant experience.
Full-stack prowess: Experience with our broader tech stack is helpful. This could mean familiarity with GraphQL (and libraries like gqlgen or Relay), Go or other back-end languages, and cloud platforms. While not required, such experience means you can hit the ground running across our codebase .
Startup mentality: You’ve been an early engineer at a startup or small team before. You understand the intensity and flexibility needed in a startup environment and are excited to wear many hats. If you love taking initiative and having a broad impact, you’ll fit right in.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO:\n\n - Own frontend across product and marketing surfaces: You will work across both our core product interface and customer-facing web pages, ensuring a cohesive, polished user experience across all touch points. This includes building features in the web app and also collaborating on our website to keep branding and user experience consistent and high-quality.\n\n - Lead design system and UI components: You’ll design, build, and maintain a scalable design system and reusable component library that empowers all our engineers and designers. By delivering robust, high-quality UI components and infrastructure, you will ensure consistency and excellence across all product surfaces. You’ll also collaborate with designers to establish guidelines and patterns, enabling the team to rapidly build beautiful, consistent UIs with confidence.\n\n - Craft pixel-perfect user experiences: Work closely with our design team to translate Figma designs into reality with pixel-perfect precision and delightful interactions. You will partner with designers to refine UI patterns and ensure every detail is right – from typography and spacing to motion and hover states. We care deeply about design craft, so you’ll sweat the details to build an interface that feels elegant, intuitive, and “just right” for users.\n\n - Champion frontend excellence: As the senior frontend expert, you will set and uphold high standards for performance, accessibility, and code quality. You’ll optimize our frontend for speed (efficient loading, bundle size, smooth rendering) and ensure our product works flawlessly across browsers and devices. You will also incorporate best practices for accessibility and internationalization, making our product usable by all customers.\n\n - Move fast with pragmatism and quality: In our startup environment, you’ll iterate quickly to ship improvements and new features. You’ll make thoughtful engineering trade-offs that balance rapid delivery with maintainability and polish. This means knowing when to build a quick solution and when to invest in the long-term path – always keeping user experience and business impact in mind.\n\n - Full-stack involvement: While your focus will be frontend, you should be comfortable venturing into the backend when needed. You’ll integrate frontend features with our GraphQL API and occasionally update server-side code (we use Go/gqlgen) to unblock frontend work. In short, you’ll do what it takes across the stack to deliver a great end-to-end product experience – without ever sacrificing our high bar for UI quality.\n\n\nWHAT YOU'LL BRING:\n\n - Frontend expertise and modern skills: Extensive experience (5+ years) building world-class web interfaces using React, TypeScript, HTML and CSS. You have a proven track record of shipping polished user interfaces in production products . Bonus points if you’ve worked with Tailwind or similar modern CSS frameworks for rapid development.\n\n - Design sense and attention to detail: You have a keen eye for good design and care deeply about the details of the user experience. We look for people who share our passion for software craftsmanship and getting even the smallest details right—this aligns with Sierra’s value of craftsmanship. You take pride in creating pixel-perfect, intuitive UIs and will proactively fix even minor UI issues because you value quality.\n\n - Strong collaboration and communication: You excel at working closely with designers and product managers to achieve the best outcome. You partner with product and design teams to craft beautiful user experiences , and you communicate clearly about tradeoffs and solutions. You’re open to feedback and can articulate your ideas in discussions, ensuring everyone is on the same page.\n\n - Self-motivation and drive: You are intensely goal-oriented and proactive, able to take ownership of projects with minimal guidance. You’ve thrived in fast-paced environments and have a track record of delivering projects quickly and frequently. You can manage ambiguity and complexity, breaking down big problems into simple, workable solutions. In short, you get things done with speed and quality in equal measure.\n\n - Pragmatic problem-solving: You approach engineering with practicality. You make effective trade-offs between ideal solutions and pragmatic deliverables, always considering the user impact and long-term maintainability. You’re not ideological about technology – you choose the best tool for the job and can learn new technologies on the fly as needed.\n\n - Front-to-back understanding: While specializing in frontend, you have a solid understanding of backend fundamentals. You know how web APIs, databases, and servers work. If needed, you can read and write server-side code. In particular, experience with GraphQL APIs and/or Golang (our backend language) is a plus for this role.\n\n\nEVEN BETTER...\n\n - Design systems experience: Previous experience building or contributing to design systems or component libraries – either at a company or in open-source—would be a big plus . This means you’ve helped create shared UI frameworks with Figma.\n\n - UI/UX specialization: An eye for user experience beyond coding —e.g. some experience with user research, visual design, or interaction design—would help you excel in crafting a delightful product. If you’ve worked closely with UX designers or have design skills yourself, that’s a bonus.\n\n - Domain experience: Exposure to AI or ML products, especially building UIs for complex data or AI-driven features. For example, if you’ve built chat interfaces, analytics dashboards, or enterprise SaaS products before, you’ll have useful relevant experience.\n\n - Full-stack prowess: Experience with our broader tech stack is helpful. This could mean familiarity with GraphQL (and libraries like gqlgen or Relay), Go or other back-end languages, and cloud platforms. While not required, such experience means you can hit the ground running across our codebase .\n\n - Startup mentality: You’ve been an early engineer at a startup or small team before. You understand the intensity and flexibility needed in a startup environment and are excited to wear many hats. If you love taking initiative and having a broad impact, you’ll fit right in.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"548eccd8-85c7-4cfa-a145-1c6ba5c17dc2","title":"Strategist, Agent Development","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-06-12T17:19:05.111+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/548eccd8-85c7-4cfa-a145-1c6ba5c17dc2","applyUrl":"https://jobs.ashbyhq.com/sierra/548eccd8-85c7-4cfa-a145-1c6ba5c17dc2/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"38f06024-4ee9-47d6-a36f-f2791ac1e412","title":"Product Manager, Agent Development (French speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:29:47.706+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/38f06024-4ee9-47d6-a36f-f2791ac1e412","applyUrl":"https://jobs.ashbyhq.com/sierra/38f06024-4ee9-47d6-a36f-f2791ac1e412/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Professional fluency in both French and English.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Professional fluency in both French and English.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"4892f01e-8871-4b32-8963-527f1cf8db5d","title":"Product Manager, Agent Development (Spanish speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:31:58.791+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/4892f01e-8871-4b32-8963-527f1cf8db5d","applyUrl":"https://jobs.ashbyhq.com/sierra/4892f01e-8871-4b32-8963-527f1cf8db5d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Professional fluency in both Spanish and English.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Professional fluency in both Spanish and English.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"c25ca18c-dbe6-439d-9a40-ce23b40c323c","title":"Strategist, Agent Development","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2025-07-29T00:28:56.262+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/c25ca18c-dbe6-439d-9a40-ce23b40c323c","applyUrl":"https://jobs.ashbyhq.com/sierra/c25ca18c-dbe6-439d-9a40-ce23b40c323c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9ebc3a79-82bf-478d-bd98-d473d41bdeaf","title":"Software Engineer, Agent (German speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:27:31.304+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9ebc3a79-82bf-478d-bd98-d473d41bdeaf","applyUrl":"https://jobs.ashbyhq.com/sierra/9ebc3a79-82bf-478d-bd98-d473d41bdeaf/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both German and English.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both German and English.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9d9e7d4a-2a27-4f64-9b1f-d79c5d3f129a","title":"Software Engineer, Agent (French speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:27:50.024+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9d9e7d4a-2a27-4f64-9b1f-d79c5d3f129a","applyUrl":"https://jobs.ashbyhq.com/sierra/9d9e7d4a-2a27-4f64-9b1f-d79c5d3f129a/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both French and English.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both French and English.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"2e5e46fd-9444-4768-94aa-2ef2bba54618","title":"Enterprise Sales Director, France","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Paris","secondaryLocations":[],"publishedAt":"2026-07-06T10:44:01.664+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"France","addressLocality":"Paris"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/2e5e46fd-9444-4768-94aa-2ef2bba54618","applyUrl":"https://jobs.ashbyhq.com/sierra/2e5e46fd-9444-4768-94aa-2ef2bba54618/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in French and English.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in French and English.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"aadfc0a0-93f6-454b-9767-c24793fa3eff","title":"Software Engineer, Agent (Spanish speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-08-21T19:28:09.367+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/aadfc0a0-93f6-454b-9767-c24793fa3eff","applyUrl":"https://jobs.ashbyhq.com/sierra/aadfc0a0-93f6-454b-9767-c24793fa3eff/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both Spanish and English.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences. Professional fluency in both Spanish and English.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ef109d91-43de-4f96-94e5-fac6f1d8c8e1","title":"Enterprise Sales Director, Spain","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Madrid","secondaryLocations":[],"publishedAt":"2026-04-28T14:40:03.110+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Spain","addressLocality":"Madrid"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ef109d91-43de-4f96-94e5-fac6f1d8c8e1","applyUrl":"https://jobs.ashbyhq.com/sierra/ef109d91-43de-4f96-94e5-fac6f1d8c8e1/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in both Spanish and English.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in both Spanish and English.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b514c750-efde-46ca-b9d3-6e76e64eb6c7","title":"Enterprise Sales Director","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-06-09T03:26:20.028+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b514c750-efde-46ca-b9d3-6e76e64eb6c7","applyUrl":"https://jobs.ashbyhq.com/sierra/b514c750-efde-46ca-b9d3-6e76e64eb6c7/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3914e14a-2339-4d49-97e8-3a0de793cfb1","title":"Software Engineer, Site Reliability (SRE)","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2025-10-21T16:14:19.273+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3914e14a-2339-4d49-97e8-3a0de793cfb1","applyUrl":"https://jobs.ashbyhq.com/sierra/3914e14a-2339-4d49-97e8-3a0de793cfb1/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Software Engineer on our Site Reliability team at Sierra, you will be responsible for defining and building the foundation of reliability, observability, and scalability across Sierra’s AI-driven infrastructure. You’ll partner closely with our core engineering and product teams to ensure our systems are highly available, efficient, and built for growth.
Own Sierra’s observability stack—monitoring, alerting, logging, and tracing—to give engineers clear visibility into system health and performance.
Partner with product and platform engineers to design systems that are reliable and scalable from day one—not as an afterthought.
Design and implement scalable, reliable, and secure cloud infrastructure (AWS) using Terraform and modern DevOps tooling.
Improve the reliability and scalability of our LLM deployments, ensuring robust, performant, and cost-effective operation.
Lead improvements to deployment pipelines, CI/CD tooling, and incident management processes to reduce downtime and response time.
Define the foundation of SRE practices at Sierra, influencing culture, tooling, and best practices across the engineering org.
5+ years of hands-on experience in Site Reliability or Infrastructure engineering roles for complex SaaS or cloud-based systems.
Experience designing for availability, scalability, and reliability at both infrastructure and application layers.
Deep experience with Terraform, AWS services, container orchestration, and cloud networking (including IAM and VPC architecture).
Strong background in observability systems (e.g., Prometheus, Grafana, Datadog, or similar).
Experience working with enterprise customers and familiarity with their compliance and networking needs along with integration patterns.
Comfortable working in fast-moving environments and collaborating across product, ML, and core engineering teams.
Degree in Computer Science or a related field, or equivalent professional experience.
Experience with LLM infrastructure — optimizing inference performance, managing fine-tuned models, or large-scale model deployment.
Past experience in an early-stage startup environment, especially defining SRE culture and tooling from scratch.
Familiarity with incident management automation or self-healing infrastructure patterns.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs a Software Engineer on our Site Reliability team at Sierra, you will be responsible for defining and building the foundation of reliability, observability, and scalability across Sierra’s AI-driven infrastructure. You’ll partner closely with our core engineering and product teams to ensure our systems are highly available, efficient, and built for growth.\n\n - Own Sierra’s observability stack—monitoring, alerting, logging, and tracing—to give engineers clear visibility into system health and performance.\n\n - Partner with product and platform engineers to design systems that are reliable and scalable from day one—not as an afterthought.\n\n - Design and implement scalable, reliable, and secure cloud infrastructure (AWS) using Terraform and modern DevOps tooling.\n\n - Improve the reliability and scalability of our LLM deployments, ensuring robust, performant, and cost-effective operation.\n\n - Lead improvements to deployment pipelines, CI/CD tooling, and incident management processes to reduce downtime and response time.\n\n - Define the foundation of SRE practices at Sierra, influencing culture, tooling, and best practices across the engineering org.\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of hands-on experience in Site Reliability or Infrastructure engineering roles for complex SaaS or cloud-based systems.\n\n - Experience designing for availability, scalability, and reliability at both infrastructure and application layers.\n\n - Deep experience with Terraform, AWS services, container orchestration, and cloud networking (including IAM and VPC architecture).\n\n - Strong background in observability systems (e.g., Prometheus, Grafana, Datadog, or similar).\n\n - Experience working with enterprise customers and familiarity with their compliance and networking needs along with integration patterns.\n\n - Comfortable working in fast-moving environments and collaborating across product, ML, and core engineering teams.\n\n - Degree in Computer Science or a related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience with LLM infrastructure — optimizing inference performance, managing fine-tuned models, or large-scale model deployment.\n\n - Past experience in an early-stage startup environment, especially defining SRE culture and tooling from scratch.\n\n - Familiarity with incident management automation or self-healing infrastructure patterns.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"2dee25a0-a0c1-425e-b67a-9d49fc821369","title":"Engineering Manager, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}}],"publishedAt":"2026-08-11T16:50:39.982+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/2dee25a0-a0c1-425e-b67a-9d49fc821369","applyUrl":"https://jobs.ashbyhq.com/sierra/2dee25a0-a0c1-425e-b67a-9d49fc821369/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead the design and delivery of production-grade AI agents: We believe the best managers lead from being hands-on and close to the work. Our managers operate as ICs for their first 3-6 months at Sierra, and then evolve to manage and grow a team of engineers, all while building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact.
Own the Agent Development Life Cycle (ADLC): You’ll both build directly, and guide your team through the full lifecycle—from initial pilot through deployment and continuous iteration—coaching engineers to set and maintain the standard for ADLC best practices. You’ll ensure projects are delivered on time, meet customer needs, and scale effectively in production environments.
Partner with large enterprises and cutting-edge startups: You’ll collaborate with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and guide your team in building AI agents that transform how they operate at scale. You’ll also work with innovative startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Shape the future of the platform: Your team’s direct work with customers will guide the evolution of Sierra’s core platform. You’ll surface unmet needs, prioritize initiatives, and collaborate with research, product, and platform teams to shape the future of AI agent development and Sierra’s product.
Experience building and scaling, as well as leading engineering teams that build and scale, end-to-end production systems
Strong technical problem-solving skills and the ability to guide teams through ambiguous, fast-changing environments
A leadership style that comes from being hands-on, and blends high standards with empathy, fostering both speed and quality
Proven ability to work closely with customers and translate business needs into technical deliverables
Excellent communication skills across technical and non-technical audiences
Degree in Computer Science or related field, or equivalent professional experience.
AI-related experience (experience developing AI agents a plus).
Experience building or deploying AI/LLM systems in production
Background as a founder, engineering lead, or startup builder with high ownership and urgency
Familiarity with tools for today’s AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Experience interfacing with customers or leading technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Lead the design and delivery of production-grade AI agents: We believe the best managers lead from being hands-on and close to the work. Our managers operate as ICs for their first 3-6 months at Sierra, and then evolve to manage and grow a team of engineers, all while building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact.\n\n - Own the Agent Development Life Cycle (ADLC): You’ll both build directly, and guide your team through the full lifecycle—from initial pilot through deployment and continuous iteration—coaching engineers to set and maintain the standard for ADLC best practices. You’ll ensure projects are delivered on time, meet customer needs, and scale effectively in production environments.\n\n - Partner with large enterprises and cutting-edge startups: You’ll collaborate with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and guide your team in building AI agents that transform how they operate at scale. You’ll also work with innovative startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Shape the future of the platform: Your team’s direct work with customers will guide the evolution of Sierra’s core platform. You’ll surface unmet needs, prioritize initiatives, and collaborate with research, product, and platform teams to shape the future of AI agent development and Sierra’s product.\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling, as well as leading engineering teams that build and scale, end-to-end production systems\n\n - Strong technical problem-solving skills and the ability to guide teams through ambiguous, fast-changing environments\n\n - A leadership style that comes from being hands-on, and blends high standards with empathy, fostering both speed and quality\n\n - Proven ability to work closely with customers and translate business needs into technical deliverables\n\n - Excellent communication skills across technical and non-technical audiences\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience developing AI agents a plus).\n\n - Experience building or deploying AI/LLM systems in production\n\n - Background as a founder, engineering lead, or startup builder with high ownership and urgency\n\n - Familiarity with tools for today’s AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Experience interfacing with customers or leading technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8d46d44c-8294-4807-a6b1-5087f0506a38","title":"Strategist, Agent Development (Spanish speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"Madrid","secondaryLocations":[],"publishedAt":"2025-10-24T15:07:32.473+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Spain","addressLocality":"Madrid"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8d46d44c-8294-4807-a6b1-5087f0506a38","applyUrl":"https://jobs.ashbyhq.com/sierra/8d46d44c-8294-4807-a6b1-5087f0506a38/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b1fc320b-d0d2-4ca5-9ce3-2ce8f51cf70e","title":"Strategist, Agent Development (French speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"Paris","secondaryLocations":[],"publishedAt":"2025-10-24T15:05:41.371+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"France","addressLocality":"Paris"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b1fc320b-d0d2-4ca5-9ce3-2ce8f51cf70e","applyUrl":"https://jobs.ashbyhq.com/sierra/b1fc320b-d0d2-4ca5-9ce3-2ce8f51cf70e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3437596e-e545-42a9-af82-9947fabf828c","title":"Strategist, Agent Development (Spanish speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-10-22T22:56:13.236+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3437596e-e545-42a9-af82-9947fabf828c","applyUrl":"https://jobs.ashbyhq.com/sierra/3437596e-e545-42a9-af82-9947fabf828c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ed38b1c1-2862-4e40-9894-3c6f20f7a785","title":"Strategist, Agent Development (French speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-10-22T22:56:08.948+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ed38b1c1-2862-4e40-9894-3c6f20f7a785","applyUrl":"https://jobs.ashbyhq.com/sierra/ed38b1c1-2862-4e40-9894-3c6f20f7a785/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"df431e56-56f5-42ed-bc62-7d6f7041bd27","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Madrid","secondaryLocations":[],"publishedAt":"2025-12-05T10:55:00.657+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Spain","addressLocality":"Madrid"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/df431e56-56f5-42ed-bc62-7d6f7041bd27","applyUrl":"https://jobs.ashbyhq.com/sierra/df431e56-56f5-42ed-bc62-7d6f7041bd27/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ea3d33e7-d5cb-480a-b542-535d70fe2736","title":"Enterprise Sales Engineer (APAC)","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-09-25T10:34:58.531+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ea3d33e7-d5cb-480a-b542-535d70fe2736","applyUrl":"https://jobs.ashbyhq.com/sierra/ea3d33e7-d5cb-480a-b542-535d70fe2736/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
AI-related experience (or experience in a similarly modern and highly technical industry).
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (or experience in a similarly modern and highly technical industry).\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"6207b02d-d334-4000-b84e-2af779171838","title":"Software Engineer, Agent (Italian speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:47:18.493+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/6207b02d-d334-4000-b84e-2af779171838","applyUrl":"https://jobs.ashbyhq.com/sierra/6207b02d-d334-4000-b84e-2af779171838/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b89816c1-80b2-449b-b69e-2c261b8e9e23","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Paris","secondaryLocations":[],"publishedAt":"2025-12-05T10:54:22.559+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"France","addressLocality":"Paris"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b89816c1-80b2-449b-b69e-2c261b8e9e23","applyUrl":"https://jobs.ashbyhq.com/sierra/b89816c1-80b2-449b-b69e-2c261b8e9e23/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalising product recommendations
Create generalisable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalising product recommendations\n\n - Create generalisable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9dc1651d-43e9-4970-a757-a5223cef1c4d","title":"Product Manager, Agent Development (Arabic speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:45:16.494+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9dc1651d-43e9-4970-a757-a5223cef1c4d","applyUrl":"https://jobs.ashbyhq.com/sierra/9dc1651d-43e9-4970-a757-a5223cef1c4d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1045b1db-228b-40df-97d8-a8f9371d35bd","title":"Strategist, Agent Development (German speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:42:53.865+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1045b1db-228b-40df-97d8-a8f9371d35bd","applyUrl":"https://jobs.ashbyhq.com/sierra/1045b1db-228b-40df-97d8-a8f9371d35bd/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"034c2c56-357f-4ed2-9da7-f4d36a999385","title":"Strategist, Agent Development (Arabic speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:43:47.710+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/034c2c56-357f-4ed2-9da7-f4d36a999385","applyUrl":"https://jobs.ashbyhq.com/sierra/034c2c56-357f-4ed2-9da7-f4d36a999385/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"2e07f536-bbaa-4cc0-957a-774ddf99de64","title":"Product Manager, Agent Development (Italian speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:45:42.176+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/2e07f536-bbaa-4cc0-957a-774ddf99de64","applyUrl":"https://jobs.ashbyhq.com/sierra/2e07f536-bbaa-4cc0-957a-774ddf99de64/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build Enterprise-grade AI Agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with Customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the Product Roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU’LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ce463311-0c6c-43d9-ab79-dd751743104f","title":"Software Engineer, Agent (Arabic speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:46:54.620+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ce463311-0c6c-43d9-ab79-dd751743104f","applyUrl":"https://jobs.ashbyhq.com/sierra/ce463311-0c6c-43d9-ab79-dd751743104f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"0e73be8d-e05f-4c47-aa74-416b2984334c","title":"Strategist, Agent Development (Italian speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2025-12-04T20:44:15.997+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/0e73be8d-e05f-4c47-aa74-416b2984334c","applyUrl":"https://jobs.ashbyhq.com/sierra/0e73be8d-e05f-4c47-aa74-416b2984334c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8646493c-93a6-482e-a810-4a0aa6e3438f","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Munich","secondaryLocations":[],"publishedAt":"2025-12-16T18:57:31.442+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Germany","addressLocality":"Munich"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8646493c-93a6-482e-a810-4a0aa6e3438f","applyUrl":"https://jobs.ashbyhq.com/sierra/8646493c-93a6-482e-a810-4a0aa6e3438f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"44120ba5-4cf7-48a1-86af-7981c41c179e","title":"Strategist, Agent Development ","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"Munich","secondaryLocations":[],"publishedAt":"2025-12-16T18:58:15.203+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Germany","addressLocality":"Munich"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/44120ba5-4cf7-48a1-86af-7981c41c179e","applyUrl":"https://jobs.ashbyhq.com/sierra/44120ba5-4cf7-48a1-86af-7981c41c179e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"a9e0b5c2-3b06-4dba-94eb-ca8fb057d70c","title":"Sales Director, DACH","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Munich","secondaryLocations":[],"publishedAt":"2025-12-16T19:01:03.524+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Germany","addressLocality":"Munich"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/a9e0b5c2-3b06-4dba-94eb-ca8fb057d70c","applyUrl":"https://jobs.ashbyhq.com/sierra/a9e0b5c2-3b06-4dba-94eb-ca8fb057d70c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9a630c65-af8c-461b-8fd4-b52ccb431f6f","title":"Technical Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-01-06T21:51:25.420+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9a630c65-af8c-461b-8fd4-b52ccb431f6f","applyUrl":"https://jobs.ashbyhq.com/sierra/9a630c65-af8c-461b-8fd4-b52ccb431f6f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting process for technical roles (engineering, product, data, and infrastructure), delivering a high-quality experience for candidates, interviewers, and hiring managers
Partner closely with hiring managers as a trusted advisor to define role requirements, develop compelling position profiles, and align on hiring priorities and timelines
Develop and execute targeted sourcing strategies across multiple channels (LinkedIn, referrals, communities, events, etc.) to attract both active and passive technical talent
Proactively identify, engage, and close top technical candidates in a competitive market
Manage and continuously optimize the interview process, ensuring efficiency, consistency, and equitable hiring practices
Track, analyze, and report on key recruiting metrics (pipeline health, time-to-fill, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence
5+ years of full-cycle recruiting experience, preferably in a fast-paced, high-growth tech environment.
Proven ability to develop and execute recruiting strategies that align with business objectives.
A well-established network within the tech industry and a passion for building new connections.
Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.
Proficiency in using recruiting metrics and data to inform decisions and improve processes.
Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.
Understanding of technical roles and the ability to assess technical talent is a plus.
Proficiency working with Ashby (ATS).
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting process for technical roles (engineering, product, data, and infrastructure), delivering a high-quality experience for candidates, interviewers, and hiring managers\n\n - Partner closely with hiring managers as a trusted advisor to define role requirements, develop compelling position profiles, and align on hiring priorities and timelines\n\n - Develop and execute targeted sourcing strategies across multiple channels (LinkedIn, referrals, communities, events, etc.) to attract both active and passive technical talent\n\n - Proactively identify, engage, and close top technical candidates in a competitive market\n\n - Manage and continuously optimize the interview process, ensuring efficiency, consistency, and equitable hiring practices\n\n - Track, analyze, and report on key recruiting metrics (pipeline health, time-to-fill, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of full-cycle recruiting experience, preferably in a fast-paced, high-growth tech environment.\n\n - Proven ability to develop and execute recruiting strategies that align with business objectives.\n\n - A well-established network within the tech industry and a passion for building new connections.\n\n - Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.\n\n - Proficiency in using recruiting metrics and data to inform decisions and improve processes.\n\n - Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.\n\n\nEVEN BETTER...\n\n - Understanding of technical roles and the ability to assess technical talent is a plus.\n\n - Proficiency working with Ashby (ATS).\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d9c7693d-2bc9-452a-94e8-f322366922fd","title":"Sales Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-07-24T14:06:28.616+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d9c7693d-2bc9-452a-94e8-f322366922fd","applyUrl":"https://jobs.ashbyhq.com/sierra/d9c7693d-2bc9-452a-94e8-f322366922fd/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting process for business roles across go-to-market (Sales, Marketing, Customer Success), Operations, Finance, People, and other cross-functional teams, delivering an exceptional experience for candidates, interviewers, and hiring managers
Act as a strategic hiring partner to business leaders, collaborating closely to define role requirements, develop clear position profiles, and align on hiring plans, priorities, and timelines
Design and execute proactive sourcing strategies across multiple channels to attract both active and passive candidates for business roles in competitive markets
Build and maintain strong candidate pipelines, effectively assessing, engaging, and closing top business talent
Drive an efficient, structured, and equitable interview process while continuously improving hiring workflows and candidate experience
Track, analyze, and report on key recruiting metrics (time-to-fill, pipeline conversion, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence
5–8+ years of full-cycle recruiting experience in a high-growth tech company, with early-stage startup experience preferred
Proven success recruiting and closing candidates across business functions, including GTM, operations, and corporate roles
Strong ability to build trusted, consultative relationships with hiring managers and interview teams
Excellent stakeholder management, communication, and prioritization skills in a fast-paced environment
Data-driven approach to recruiting with experience using metrics to inform hiring decisions and process improvements
Experience recruiting for GTM teams in a SaaS or B2B environment
Experience with Ashby ATS
Experience scaling business teams during periods of rapid growth
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting process for business roles across go-to-market (Sales, Marketing, Customer Success), Operations, Finance, People, and other cross-functional teams, delivering an exceptional experience for candidates, interviewers, and hiring managers\n\n - Act as a strategic hiring partner to business leaders, collaborating closely to define role requirements, develop clear position profiles, and align on hiring plans, priorities, and timelines\n\n - Design and execute proactive sourcing strategies across multiple channels to attract both active and passive candidates for business roles in competitive markets\n\n - Build and maintain strong candidate pipelines, effectively assessing, engaging, and closing top business talent\n\n - Drive an efficient, structured, and equitable interview process while continuously improving hiring workflows and candidate experience\n\n - Track, analyze, and report on key recruiting metrics (time-to-fill, pipeline conversion, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5–8+ years of full-cycle recruiting experience in a high-growth tech company, with early-stage startup experience preferred\n\n - Proven success recruiting and closing candidates across business functions, including GTM, operations, and corporate roles\n\n - Strong ability to build trusted, consultative relationships with hiring managers and interview teams\n\n - Excellent stakeholder management, communication, and prioritization skills in a fast-paced environment\n\n - Data-driven approach to recruiting with experience using metrics to inform hiring decisions and process improvements\n\n\nEVEN BETTER...\n\n - Experience recruiting for GTM teams in a SaaS or B2B environment\n\n - Experience with Ashby ATS\n\n - Experience scaling business teams during periods of rapid growth\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"c0c29aa8-0c94-4d03-858e-201d19ee6937","title":"Sales Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-31T20:11:41.973+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/c0c29aa8-0c94-4d03-858e-201d19ee6937","applyUrl":"https://jobs.ashbyhq.com/sierra/c0c29aa8-0c94-4d03-858e-201d19ee6937/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting process for business roles across go-to-market teams, delivering an exceptional experience for candidates, interviewers, and hiring managers
Act as a strategic hiring partner to business leaders, collaborating closely to define role requirements, develop clear position profiles, and align on hiring plans, priorities, and timelines
Design and execute proactive sourcing strategies across multiple channels to attract both active and passive candidates for business roles in competitive markets
Build and maintain strong candidate pipelines, effectively assessing, engaging, and closing top business talent
Drive an efficient, structured, and equitable interview process while continuously improving hiring workflows and candidate experience
Track, analyze, and report on key recruiting metrics (time-to-fill, pipeline conversion, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence
5–8+ years of full-cycle recruiting experience in a high-growth tech company, with early-stage startup experience preferred
Proven success recruiting and closing candidates across business functions, including GTM, operations, and corporate roles
Strong ability to build trusted, consultative relationships with hiring managers and interview teams
Excellent stakeholder management, communication, and prioritization skills in a fast-paced environment
Data-driven approach to recruiting with experience using metrics to inform hiring decisions and process improvements
Experience recruiting for GTM teams in a SaaS or B2B environment
Experience with Ashby ATS
Experience scaling business teams during periods of rapid growth
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting process for business roles across go-to-market teams, delivering an exceptional experience for candidates, interviewers, and hiring managers\n\n - Act as a strategic hiring partner to business leaders, collaborating closely to define role requirements, develop clear position profiles, and align on hiring plans, priorities, and timelines\n\n - Design and execute proactive sourcing strategies across multiple channels to attract both active and passive candidates for business roles in competitive markets\n\n - Build and maintain strong candidate pipelines, effectively assessing, engaging, and closing top business talent\n\n - Drive an efficient, structured, and equitable interview process while continuously improving hiring workflows and candidate experience\n\n - Track, analyze, and report on key recruiting metrics (time-to-fill, pipeline conversion, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5–8+ years of full-cycle recruiting experience in a high-growth tech company, with early-stage startup experience preferred\n\n - Proven success recruiting and closing candidates across business functions, including GTM, operations, and corporate roles\n\n - Strong ability to build trusted, consultative relationships with hiring managers and interview teams\n\n - Excellent stakeholder management, communication, and prioritization skills in a fast-paced environment\n\n - Data-driven approach to recruiting with experience using metrics to inform hiring decisions and process improvements\n\n\nEVEN BETTER...\n\n - Experience recruiting for GTM teams in a SaaS or B2B environment\n\n - Experience with Ashby ATS\n\n - Experience scaling business teams during periods of rapid growth\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"201c6046-acb5-4fd4-a685-e993f34ec0d1","title":"Software Engineer, Security","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-01-07T22:15:42.038+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/201c6046-acb5-4fd4-a685-e993f34ec0d1","applyUrl":"https://jobs.ashbyhq.com/sierra/201c6046-acb5-4fd4-a685-e993f34ec0d1/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Security Engineering builds the foundations that let Sierra deliver powerful AI agents while protecting customer data and trust. We partner across product and platform to make security, privacy, and safety core product capabilities and secure defaults.
Our work spans several security domains. You’ll go deep where your strengths and interests are strongest, with opportunities to explore new areas alongside the team.
Build the Foundations of Trust.
Design and ship systems that make Sierra’s platform secure by default — spanning agent safety/security, privacy, identity, authentication, authorization, and data security. You’ll work across all layers of production (agents, infrastructure, backend, frontend) to embed security-conscious design into the core of our product.
Own Cross-Cutting Systems.
Partner with product and platform teams to implement and evolve Sierra’s trust primitives: identity management, access control, auditability, and data lifecycle management. You’ll make pragmatic design trade-offs between usability, performance, and security.
Secure Agentic AI Systems.
Build controls that ensure AI agents can't leak customer data, execute unauthorized actions, or be manipulated into unintended behavior. Design runtime policy enforcement for tool use, implement safe agent sandboxing, and create boundaries that protect data while keeping agents powerful and useful.
Automate and Scale Security-Adjacent Workflows.
Create developer-friendly tooling to reduce risk and friction — whether through automating security checks in CI/CD, enforcing privacy boundaries through schema validation, or instrumenting runtime monitoring for sensitive events.
Strong Software Engineering Skills.
Experience building and maintaining production systems. You’re comfortable designing APIs, integrating with authentication or identity frameworks, and thoughtfully using AI-assisted development tools to build, test, and ship high-quality code faster without lowering the quality bar.
Security Mindset.
You think like a security engineer — considering how data flows, where it’s stored, who can access it, and how to design for least privilege and transparency.
Product and Platform Mindset.
You care about building secure scalable systems that enable, not block, innovation. You work closely with product teams to make trade-offs clear and help them move quickly without sacrificing trust.
Curiosity and Ownership.
You take ambiguous, cross-cutting problems from first principles to production and go deep when needed: tracing an authorization decision from agent intent through policy enforcement and downstream effects, or following sensitive data across model context, logs, storage, and tenant boundaries. You define the problem, align partners, ship the solution, and own it in production.
You’ve worked on privacy, identity, trust & safety, authN/authz, or data protection systems.
You’ve built security frameworks, libraries, or tooling that developers actually use or integrated security automation into CI/CD pipelines.
You have exposure to AI systems or care about designing secure-by-default LLM applications.
You think like an attacker — you naturally ask \"what could go wrong?\" when reviewing designs or while building systems. You've found or fixed real security issues in production systems.
You thrive in 0→1 environments, where foundational systems have to balance speed, reliability, and trust.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\n\n\nSOFTWARE ENGINEER, SECURITY\n\nSecurity Engineering builds the foundations that let Sierra deliver powerful AI agents while protecting customer data and trust. We partner across product and platform to make security, privacy, and safety core product capabilities and secure defaults.\n\n \n\n\nWHAT YOU’LL DO\n\nOur work spans several security domains. You’ll go deep where your strengths and interests are strongest, with opportunities to explore new areas alongside the team.\n\nBuild the Foundations of Trust.\nDesign and ship systems that make Sierra’s platform secure by default — spanning agent safety/security, privacy, identity, authentication, authorization, and data security. You’ll work across all layers of production (agents, infrastructure, backend, frontend) to embed security-conscious design into the core of our product.\n\nOwn Cross-Cutting Systems.\nPartner with product and platform teams to implement and evolve Sierra’s trust primitives: identity management, access control, auditability, and data lifecycle management. You’ll make pragmatic design trade-offs between usability, performance, and security.\n\nSecure Agentic AI Systems.\n\nBuild controls that ensure AI agents can't leak customer data, execute unauthorized actions, or be manipulated into unintended behavior. Design runtime policy enforcement for tool use, implement safe agent sandboxing, and create boundaries that protect data while keeping agents powerful and useful.\n\nAutomate and Scale Security-Adjacent Workflows.\nCreate developer-friendly tooling to reduce risk and friction — whether through automating security checks in CI/CD, enforcing privacy boundaries through schema validation, or instrumenting runtime monitoring for sensitive events.\n\n \n\n\nWHAT YOU’LL BRING\n\nStrong Software Engineering Skills.\nExperience building and maintaining production systems. You’re comfortable designing APIs, integrating with authentication or identity frameworks, and thoughtfully using AI-assisted development tools to build, test, and ship high-quality code faster without lowering the quality bar.\n\nSecurity Mindset.\nYou think like a security engineer — considering how data flows, where it’s stored, who can access it, and how to design for least privilege and transparency.\n\nProduct and Platform Mindset.\nYou care about building secure scalable systems that enable, not block, innovation. You work closely with product teams to make trade-offs clear and help them move quickly without sacrificing trust.\n\nCuriosity and Ownership.\nYou take ambiguous, cross-cutting problems from first principles to production and go deep when needed: tracing an authorization decision from agent intent through policy enforcement and downstream effects, or following sensitive data across model context, logs, storage, and tenant boundaries. You define the problem, align partners, ship the solution, and own it in production.\n\n\n\n\nEVEN BETTER IF…\n\n - You’ve worked on privacy, identity, trust & safety, authN/authz, or data protection systems.\n\n - You’ve built security frameworks, libraries, or tooling that developers actually use or integrated security automation into CI/CD pipelines.\n\n - You have exposure to AI systems or care about designing secure-by-default LLM applications.\n\n - You think like an attacker — you naturally ask \"what could go wrong?\" when reviewing designs or while building systems. You've found or fixed real security issues in production systems.\n\n - You thrive in 0→1 environments, where foundational systems have to balance speed, reliability, and trust.\n\n \n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"39e15cc4-a16e-4ddb-b609-a345e2dd67c8","title":"GTM Operations, Pricing","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-05T15:26:41.218+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/39e15cc4-a16e-4ddb-b609-a345e2dd67c8","applyUrl":"https://jobs.ashbyhq.com/sierra/39e15cc4-a16e-4ddb-b609-a345e2dd67c8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra’s outcomes-based pricing model is central to how we partner with customers. In this role, you will work with senior leaders across Sales, Operations, Product, Finance, and Legal. You will help negotiate complex partnerships with Fortune 500 companies, build business cases that demonstrate Sierra’s value, and shape pricing strategies for AI agents that drive revenue, improve retention, and transform core business processes.
Lead pricing strategy for major enterprise opportunities, from early customer discussions through negotiation and close
Develop commercial models and ROI analyses that connect Sierra’s performance to measurable customer value
Bring clear analysis and sound judgment to high-stakes customer negotiations
Partner across the company to turn new product capabilities into scalable commercial offerings
4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.
Experience negotiating complex customer partnerships and familiarity with navigating sales cycles
Strong financial modeling skills and the ability to turn analysis into a clear executive recommendation
Excellent commercial judgment, including the ability to make thoughtful decisions with incomplete information
Clear written and verbal communication with senior leaders
Degree in Business Administration, Finance, or related field, or equivalent professional experience
Experience in partnerships, business development, and value engineering roles
Familiarity with AI or conversational AI technologies
Previous 0-1 startup or fast-paced high-growth environment experience
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nSierra’s outcomes-based pricing model is central to how we partner with customers. In this role, you will work with senior leaders across Sales, Operations, Product, Finance, and Legal. You will help negotiate complex partnerships with Fortune 500 companies, build business cases that demonstrate Sierra’s value, and shape pricing strategies for AI agents that drive revenue, improve retention, and transform core business processes.\n\n - Lead pricing strategy for major enterprise opportunities, from early customer discussions through negotiation and close\n\n - Develop commercial models and ROI analyses that connect Sierra’s performance to measurable customer value\n\n - Bring clear analysis and sound judgment to high-stakes customer negotiations\n\n - Partner across the company to turn new product capabilities into scalable commercial offerings\n\n\nWHAT YOU'LL BRING:\n\n - 4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.\n\n - Experience negotiating complex customer partnerships and familiarity with navigating sales cycles\n\n - Strong financial modeling skills and the ability to turn analysis into a clear executive recommendation\n\n - Excellent commercial judgment, including the ability to make thoughtful decisions with incomplete information\n\n - Clear written and verbal communication with senior leaders\n\n - Degree in Business Administration, Finance, or related field, or equivalent professional experience\n\n\nEVEN BETTER...\n\n - Experience in partnerships, business development, and value engineering roles\n\n - Familiarity with AI or conversational AI technologies\n\n - Previous 0-1 startup or fast-paced high-growth environment experience\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ab15547e-5c50-48a8-a560-f56c7bdad587","title":"Strategist, Agent Development (Cantonese Speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-10-03T02:14:58.689+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ab15547e-5c50-48a8-a560-f56c7bdad587","applyUrl":"https://jobs.ashbyhq.com/sierra/ab15547e-5c50-48a8-a560-f56c7bdad587/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1a0a0334-41f8-4c15-9ed8-615336855e5e","title":"Engineering Manager, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-02-27T14:12:28.892+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1a0a0334-41f8-4c15-9ed8-615336855e5e","applyUrl":"https://jobs.ashbyhq.com/sierra/1a0a0334-41f8-4c15-9ed8-615336855e5e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead the design and delivery of production-grade AI agents: You’ll manage and grow a team of engineers building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact.
Own the Agent Development Life Cycle (ADLC): You’ll guide your team through the full lifecycle—from initial pilot through deployment and continuous iteration—coaching engineers to set and maintain the standard for ADLC best practices. You’ll ensure projects are delivered on time, meet customer needs, and scale effectively in production environments.
Partner with large enterprises and cutting-edge startups: You’ll collaborate with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and guide your team in building AI agents that transform how they operate at scale. You’ll also work with innovative startups in Europe, embedding AI agents across their entire business stack to drive innovation and efficiency.
Shape the future of the platform: Your team’s direct work with customers will guide the evolution of Sierra’s core platform. You’ll surface unmet needs, prioritise initiatives, and collaborate with research, product, and platform teams to shape the future of AI agent development and Sierra’s product.
Experience leading engineering teams that build and scale end-to-end production systems
Strong technical problem-solving skills and the ability to guide teams through ambiguous, fast-changing environments
A leadership style that blends high standards with empathy, fostering both speed and quality
Proven ability to work closely with customers and translate business needs into technical deliverables
Excellent communication skills across technical and non-technical audiences
Degree in Computer Science or related field, or equivalent professional experience.
AI-related experience (experience developing AI agents a plus).
Experience building or deploying AI/LLM systems in production
Background as a founder, engineering lead, or startup builder with high ownership and urgency
Familiarity with tools for today’s AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Experience interfacing with customers or leading technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Lead the design and delivery of production-grade AI agents: You’ll manage and grow a team of engineers building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact.\n\n - Own the Agent Development Life Cycle (ADLC): You’ll guide your team through the full lifecycle—from initial pilot through deployment and continuous iteration—coaching engineers to set and maintain the standard for ADLC best practices. You’ll ensure projects are delivered on time, meet customer needs, and scale effectively in production environments.\n\n - Partner with large enterprises and cutting-edge startups: You’ll collaborate with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and guide your team in building AI agents that transform how they operate at scale. You’ll also work with innovative startups in Europe, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Shape the future of the platform: Your team’s direct work with customers will guide the evolution of Sierra’s core platform. You’ll surface unmet needs, prioritise initiatives, and collaborate with research, product, and platform teams to shape the future of AI agent development and Sierra’s product.\n\n\nWHAT YOU'LL BRING\n\n - Experience leading engineering teams that build and scale end-to-end production systems\n\n - Strong technical problem-solving skills and the ability to guide teams through ambiguous, fast-changing environments\n\n - A leadership style that blends high standards with empathy, fostering both speed and quality\n\n - Proven ability to work closely with customers and translate business needs into technical deliverables\n\n - Excellent communication skills across technical and non-technical audiences\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience developing AI agents a plus).\n\n - Experience building or deploying AI/LLM systems in production\n\n - Background as a founder, engineering lead, or startup builder with high ownership and urgency\n\n - Familiarity with tools for today’s AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Experience interfacing with customers or leading technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"a4376f1f-10bd-4804-899e-4b98b8245198","title":"Enterprise Sales Leader ","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-01-16T22:32:30.143+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/a4376f1f-10bd-4804-899e-4b98b8245198","applyUrl":"https://jobs.ashbyhq.com/sierra/a4376f1f-10bd-4804-899e-4b98b8245198/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1c991675-099f-49dd-9b9b-bd3c9111e65c","title":"GTM Engineer","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-01-29T19:00:05.861+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1c991675-099f-49dd-9b9b-bd3c9111e65c","applyUrl":"https://jobs.ashbyhq.com/sierra/1c991675-099f-49dd-9b9b-bd3c9111e65c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Implement Go-to-Market software for our marketing, sales, and agent development teams
Design and build the automated workflows, integrations, and AI-powered systems that turn signal into pipeline, across enrichment, scoring, routing, and outbound activation
Own our enrichment infrastructure end-to-end: the pipelines that take a new signup, demo request, or event attendee list and return a fully enriched, scored, Salesforce-upserted record across Clay, ZoomInfo, Cognism, and LLM-powered sources
Build AI agents and AI-powered internal tools that compound sales team output — account research, call summarization, RFP and security questionnaire response, proposal generation, and Slack-accessible agents that surface account intel on demand
Build and improve the fit scoring pipeline that evaluates every account against our ICP and writes results to Postgres and Salesforce, including signal design, batching, retry logic, and continuous improvement of the underlying models
Develop data architecture using Postgres, Fivetran pipelines, and reverse ETL. Keep data jobs healthy and in sync with the tools that consume them; track downstream impact when schemas and apps change
Ship production code with PR review, observability, and proper error handling and debug production incidents (Salesforce platform failures, enrichment failures, LLM timeouts)
3+ years in GTM Engineering, Revenue Operations, Sales Engineering, Growth Engineering, or a closely adjacent technical role at a high-growth B2B SaaS company
Python and TypeScript skills: You write clean code, understand async patterns, can design a database schema, and can debug a production incident from logs alone
Hands-on experience inside a modern GTM stack (Salesforce, HubSpot, Outreach, Clay, enrichment providers): You understand how leads flow through a CRM and why data quality degrades over time
Production experience with LLMs: Prompt design, eval loops, error handling, and the difference between a demo and a system you can trust at scale
Strong working knowledge of SQL, schemas, and data flow across GTM and warehouse systems
Systems thinking: You’ve built data pipelines and think about what happens at 10x volume, when an API goes down, or when the same account hits your queue five times in parallel
Owner's mindset: You take accountability from code to deployment to adoption, define scope with minimal direction, and ship good solutions over perfect ones
Built applications using LLMs, ideally with exposure to production-grade AI/ML systems
Developed custom Salesforce solutions using apex classes, apex triggers, LWC, SLDS
Integrated salesforce with other business systems using REST/SOAP APIs, Platform Events, and External Services
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Implement Go-to-Market software for our marketing, sales, and agent development teams\n\n - Design and build the automated workflows, integrations, and AI-powered systems that turn signal into pipeline, across enrichment, scoring, routing, and outbound activation\n\n - Own our enrichment infrastructure end-to-end: the pipelines that take a new signup, demo request, or event attendee list and return a fully enriched, scored, Salesforce-upserted record across Clay, ZoomInfo, Cognism, and LLM-powered sources\n\n - Build AI agents and AI-powered internal tools that compound sales team output — account research, call summarization, RFP and security questionnaire response, proposal generation, and Slack-accessible agents that surface account intel on demand\n\n - Build and improve the fit scoring pipeline that evaluates every account against our ICP and writes results to Postgres and Salesforce, including signal design, batching, retry logic, and continuous improvement of the underlying models\n\n - Develop data architecture using Postgres, Fivetran pipelines, and reverse ETL. Keep data jobs healthy and in sync with the tools that consume them; track downstream impact when schemas and apps change\n\n - Ship production code with PR review, observability, and proper error handling and debug production incidents (Salesforce platform failures, enrichment failures, LLM timeouts)\n\n\nWHAT YOU'LL BRING\n\n - 3+ years in GTM Engineering, Revenue Operations, Sales Engineering, Growth Engineering, or a closely adjacent technical role at a high-growth B2B SaaS company\n\n - Python and TypeScript skills: You write clean code, understand async patterns, can design a database schema, and can debug a production incident from logs alone\n\n - Hands-on experience inside a modern GTM stack (Salesforce, HubSpot, Outreach, Clay, enrichment providers): You understand how leads flow through a CRM and why data quality degrades over time\n\n - Production experience with LLMs: Prompt design, eval loops, error handling, and the difference between a demo and a system you can trust at scale\n\n - Strong working knowledge of SQL, schemas, and data flow across GTM and warehouse systems\n\n - Systems thinking: You’ve built data pipelines and think about what happens at 10x volume, when an API goes down, or when the same account hits your queue five times in parallel\n\n - Owner's mindset: You take accountability from code to deployment to adoption, define scope with minimal direction, and ship good solutions over perfect ones\n\n\nEVEN BETTER…\n\n - Built applications using LLMs, ideally with exposure to production-grade AI/ML systems\n\n - Developed custom Salesforce solutions using apex classes, apex triggers, LWC, SLDS\n\n - Integrated salesforce with other business systems using REST/SOAP APIs, Platform Events, and External Services\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"bc98b50a-d6ea-42b8-b1c6-f55099d1bb1c","title":"Product Manager, Agent Development - Financial Services","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-08-30T23:34:08.661+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/bc98b50a-d6ea-42b8-b1c6-f55099d1bb1c","applyUrl":"https://jobs.ashbyhq.com/sierra/bc98b50a-d6ea-42b8-b1c6-f55099d1bb1c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-10+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience in financial services, such as banking, fintech, lending, payments, insurance, mortgages, or wealth management.
A track record of taking products from ambiguous customer problems through launch and meaningful scale.
Strong technical fluency and the ability to reason about APIs, data flows, system architecture, AI systems, integrations, and failure modes.
Exceptional product judgment, including the ability to balance customer needs, speed, reliability, risk, and long-term platform leverage.
Experience working directly with enterprise customers and communicating effectively with both executives and deeply technical teams.
A builder mindset: you prototype, investigate, and work hands-on rather than relying solely on process.
Clear, structured communication, with the ability to explain complex technical and AI concepts to diverse audiences and create alignment in fast-moving, ambiguous environments.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\n\n\nWHAT YOU'LL BRING\n\n - 5-10+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience in financial services, such as banking, fintech, lending, payments, insurance, mortgages, or wealth management.\n\n - A track record of taking products from ambiguous customer problems through launch and meaningful scale.\n\n - Strong technical fluency and the ability to reason about APIs, data flows, system architecture, AI systems, integrations, and failure modes.\n\n - Exceptional product judgment, including the ability to balance customer needs, speed, reliability, risk, and long-term platform leverage.\n\n - Experience working directly with enterprise customers and communicating effectively with both executives and deeply technical teams.\n\n - A builder mindset: you prototype, investigate, and work hands-on rather than relying solely on process.\n\n - Clear, structured communication, with the ability to explain complex technical and AI concepts to diverse audiences and create alignment in fast-moving, ambiguous environments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"fc6eaada-479c-4ff6-be79-7e267b9ed2b4","title":"Software Engineer, Admin Experience","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-02-04T21:09:46.335+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/fc6eaada-479c-4ff6-be79-7e267b9ed2b4","applyUrl":"https://jobs.ashbyhq.com/sierra/fc6eaada-479c-4ff6-be79-7e267b9ed2b4/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build Sierra’s enterprise platform capabilities.
You’ll design and build the foundational systems and capabilities that enable Sierra to serve the world’s largest and most demanding enterprises. This includes the identity, access management, integration points, and extensibility that enterprise customers require to allow customers to embed Sierra into their existing ecosystems.
Scale with our largest customers.
Our enterprise customers have complex environments, strict security requirements, and high expectations for reliability. You’ll ensure Sierra’s platform scales across organizations, regions, and use cases while maintaining performance and simplicity.
Form the foundation of trust.
Enterprise customers trust Sierra with their most sensitive workflows and data. You’ll help set and uphold a high bar for security, compliance readiness, reliability, and operational excellence across the platform.
A passion for being on the frontier of AI products.
Pride in building reliable, maintainable, and secure systems that scale.
Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.
Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.
4+ years hands-on experience building production products and systems.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building enterprise features such as SSO, RBAC, IAM, audit logs, or compliance-adjacent systems.
Experience with integrations, APIs, and working with complex customer environments.
Backend-leaning full-stack experience building enterprise SaaS applications.
Security-adjacent experience (e.g., auth, permissions, data isolation, threat modeling).
Experience building AI-powered products or platforms.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Build Sierra’s enterprise platform capabilities.\n You’ll design and build the foundational systems and capabilities that enable Sierra to serve the world’s largest and most demanding enterprises. This includes the identity, access management, integration points, and extensibility that enterprise customers require to allow customers to embed Sierra into their existing ecosystems.\n\n - Scale with our largest customers.\n Our enterprise customers have complex environments, strict security requirements, and high expectations for reliability. You’ll ensure Sierra’s platform scales across organizations, regions, and use cases while maintaining performance and simplicity.\n\n - Form the foundation of trust.\n Enterprise customers trust Sierra with their most sensitive workflows and data. You’ll help set and uphold a high bar for security, compliance readiness, reliability, and operational excellence across the platform.\n\n\nWHAT YOU’LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Pride in building reliable, maintainable, and secure systems that scale.\n\n - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.\n\n - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.\n\n - 4+ years hands-on experience building production products and systems.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER…\n\n - Experience building enterprise features such as SSO, RBAC, IAM, audit logs, or compliance-adjacent systems.\n\n - Experience with integrations, APIs, and working with complex customer environments.\n\n - Backend-leaning full-stack experience building enterprise SaaS applications.\n\n - Security-adjacent experience (e.g., auth, permissions, data isolation, threat modeling).\n\n - Experience building AI-powered products or platforms.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"06453dd1-a29f-4aea-bb06-2d49862860e8","title":"Developer Relations Engineer","department":"Partnerships","team":"Developer Relations","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}}],"publishedAt":"2026-02-06T17:22:42.616+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/06453dd1-a29f-4aea-bb06-2d49862860e8","applyUrl":"https://jobs.ashbyhq.com/sierra/06453dd1-a29f-4aea-bb06-2d49862860e8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Write the playbook for onboarding and educating customers onto Sierra – both the Agent SDK and Agent Studio, our no-code platform.
Lead the creation and execution of developer training and enablement programs.
Build content that scales — including technical documentation, educational videos, onboarding paths, and sample repositories for SDK adoption.
Develop and deploy AI Agents as an Agent Software Engineer, building the knowledge to become a world-leading expert on agent development.
Work with our marketing teams to publish developer case studies and success stories to inspire and connect our growing technical community.
One important aspect of this role is presenting educational content to customers, both live and on video. If you have recordings of any presentations you've given in the past, add links to one or two of your favorites here.
Passion for helping customers across small and large enterprises learn to build exceptional AI Agents.
Degree in Computer Science or related field, or equivalent professional experience.
4+ years of experience in hands-on software development of highly technical products or developer relations roles.
Excellent written and verbal communication skills and a desire to apply them in hands-on training sessions.
Desire, excitement, and enthusiasm for building an in-person, global community around developing AI Agents.
Strong technical skills and familiarity with modern software development — especially developer tooling, SDKs, and APIs.
Demonstrated experience in designing and executing technical training, certification, or community initiatives.
Previous experience developing agents using open source tools like LangGraph or interacting with MCP servers.
Familiarity with agent platforms, developer communities, or early-stage developer product ecosystems.
Proficiency with TypeScript, and comfort with writing code in collaboration with agents like Claude, Codex or Cursor
Experience collaborating across product, engineering, and go-to-market teams to launch strategic initiatives.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Write the playbook for onboarding and educating customers onto Sierra – both the Agent SDK and Agent Studio, our no-code platform. \n\n - Lead the creation and execution of developer training and enablement programs.\n\n - Build content that scales — including technical documentation, educational videos, onboarding paths, and sample repositories for SDK adoption.\n\n - Develop and deploy AI Agents as an Agent Software Engineer, building the knowledge to become a world-leading expert on agent development.\n\n - Work with our marketing teams to publish developer case studies and success stories to inspire and connect our growing technical community.\n\n - One important aspect of this role is presenting educational content to customers, both live and on video. If you have recordings of any presentations you've given in the past, add links to one or two of your favorites here.\n\n\nWHAT YOU'LL BRING\n\n - Passion for helping customers across small and large enterprises learn to build exceptional AI Agents.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n - 4+ years of experience in hands-on software development of highly technical products or developer relations roles.\n\n - Excellent written and verbal communication skills and a desire to apply them in hands-on training sessions.\n\n - Desire, excitement, and enthusiasm for building an in-person, global community around developing AI Agents.\n\n - Strong technical skills and familiarity with modern software development — especially developer tooling, SDKs, and APIs.\n\n - Demonstrated experience in designing and executing technical training, certification, or community initiatives.\n\n\nEVEN BETTER...\n\n - Previous experience developing agents using open source tools like LangGraph or interacting with MCP servers.\n\n - Familiarity with agent platforms, developer communities, or early-stage developer product ecosystems.\n\n - Proficiency with TypeScript, and comfort with writing code in collaboration with agents like Claude, Codex or Cursor\n\n - Experience collaborating across product, engineering, and go-to-market teams to launch strategic initiatives.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ae9e7e56-df4e-420f-8130-91b4c59e0fb0","title":"Office Coordinator (Contract)","department":"Operations","team":"Workplace","employmentType":"Contract","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-11T00:50:12.523+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ae9e7e56-df4e-420f-8130-91b4c59e0fb0","applyUrl":"https://jobs.ashbyhq.com/sierra/ae9e7e56-df4e-420f-8130-91b4c59e0fb0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an office coordinator at Sierra, you will be responsible for creating and operating exceptional workplace environments that enable our teams to do the best work. You will bring the same level of craftsmanship, intensity, and customer obsession to our physical spaces that we bring to the products we build for our customers.
In this role, you will own day-to-day office operations, including the experience across our customer facing spaces at our San Francisco headquarters. You will partner closely with Operations, IT and HR teams to ensure every office runs seamlessly and reflects Sierra’s high standards.
We are looking for a hospitality-minded, detail-oriented person who can effectively prioritize in a fast-paced environment. You should take deep pride in delivering an exceptional experience for employees, candidates, customers, and visitors.
This role is based in San Francisco and is fully onsite five days per week given the hands-on nature of the position.
Oversee the daily operations of our customer-facing spaces.
Greet guests at reception and foster a warm, welcoming office environment.
Pick up incoming mail, distribute packages to employees, and coordinate package pickups.
Maintain the organization and appearance of kitchens, storage rooms, and self-service stations.
Manage office inventory and assemble gift packages, including baby and customer gifts.
Support Executive Assistants with meeting logistics, including lunch and coffee setup for customer and internal executive meetings.
Track CPR and First Aid certifications for office staff and ensure first aid kits and safety equipment are stocked and up to date.
Serve as the primary point of contact for facilities requests and repairs, partnering with property management as needed.
Partner with the People team on new hire onboarding logistics, including workspace setup, badge access, and office orientation.
This is a 6-month contract position that is ineligible for the benefits listed below. The role may be extended or converted to full-time.
2–4 years of experience in office coordination, administrative, or a similar role.
Strong organizational and communication skills.
The ability to work effectively in a fast-paced environment and adapt to shifting priorities.
A commitment to unreasonable hospitality and a willingness to go above and beyond for employees and guests.
Previous experience in a customer-facing position is preferred.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nAs an office coordinator at Sierra, you will be responsible for creating and operating exceptional workplace environments that enable our teams to do the best work. You will bring the same level of craftsmanship, intensity, and customer obsession to our physical spaces that we bring to the products we build for our customers.\n\nIn this role, you will own day-to-day office operations, including the experience across our customer facing spaces at our San Francisco headquarters. You will partner closely with Operations, IT and HR teams to ensure every office runs seamlessly and reflects Sierra’s high standards.\n\nWe are looking for a hospitality-minded, detail-oriented person who can effectively prioritize in a fast-paced environment. You should take deep pride in delivering an exceptional experience for employees, candidates, customers, and visitors. \n\nThis role is based in San Francisco and is fully onsite five days per week given the hands-on nature of the position.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Oversee the daily operations of our customer-facing spaces.\n\n - Greet guests at reception and foster a warm, welcoming office environment.\n\n - Pick up incoming mail, distribute packages to employees, and coordinate package pickups.\n\n - Maintain the organization and appearance of kitchens, storage rooms, and self-service stations.\n\n - Manage office inventory and assemble gift packages, including baby and customer gifts.\n\n - Support Executive Assistants with meeting logistics, including lunch and coffee setup for customer and internal executive meetings.\n\n - Track CPR and First Aid certifications for office staff and ensure first aid kits and safety equipment are stocked and up to date.\n\n - Serve as the primary point of contact for facilities requests and repairs, partnering with property management as needed.\n\n - Partner with the People team on new hire onboarding logistics, including workspace setup, badge access, and office orientation.\n\n - This is a 6-month contract position that is ineligible for the benefits listed below. The role may be extended or converted to full-time.\n\n\nWHAT YOU’LL BRING:\n\n - 2–4 years of experience in office coordination, administrative, or a similar role.\n\n - Strong organizational and communication skills.\n\n - The ability to work effectively in a fast-paced environment and adapt to shifting priorities.\n\n - A commitment to unreasonable hospitality and a willingness to go above and beyond for employees and guests.\n\n - Previous experience in a customer-facing position is preferred.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"687a56db-9f2a-42f9-94a0-fa06730c1e10","title":"Security and Compliance Manager","department":"Security Programs & GRC","team":"Security Programs & GRC","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-02-12T22:34:40.748+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/687a56db-9f2a-42f9-94a0-fa06730c1e10","applyUrl":"https://jobs.ashbyhq.com/sierra/687a56db-9f2a-42f9-94a0-fa06730c1e10/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own independent audits and regulatory programs including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, HIPAA, and related frameworks.
Drive scope definition, readiness assessments, auditor engagement, remediation planning, and executive level reporting.
Develop a strong working understanding of Sierra’s Conversational AI Platform, model providers, and cloud architecture. Partner with Platform and Agent Engineering to design and operationalize controls across multi cloud environments, infrastructure, inference and data platforms.
Build a centralized and evolving security controls library mapped to compliance, regulatory and customer requirements. Continuously assess control effectiveness, identify gaps, prioritize risk, and drive remediation that strengthens Sierra’s security and compliance posture.
Define and enforce security baselines for cloud infrastructure, containerized workloads, Kubernetes, identity, encryption, logging, and network security controls. Partner with engineering teams to integrate security requirements into configuration and change management.
Design and operate automated compliance workflows using AI, infrastructure as code, and security tooling to reduce manual effort, improve control assurance, and scale with platform evolution.
You will act as a strategic partner to Platform, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity.
8+ years of experience in security compliance or GRC or security adjacent roles within fast growing technology companies.
Deep expertise in security compliance frameworks including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, and similar regulatory environments.
A systems oriented and engineering focused GRC mindset, with the ability to reason about cloud architecture, data flows, and control effectiveness alongside engineers.
Experience owning complex audits and driving risk based remediation across distributed teams.
Hands-on experience with multi-cloud infrastructure (AWS, Azure, GCP).
Strong experience implementing and automating security controls across cloud infrastructure, configuration management, container security, Kubernetes, encryption, identity, and authentication systems.
Ability to clearly communicate compliance requirements internally to engineering teams and externally to customers in a technically credible way.
Relevant certifications such as CISSP, CISA, PCI ISA, ISO 27001 Lead Auditor, or equivalent experience.
Experience supporting AI platforms, fintech, healthcare, or other highly regulated environments.
Familiarity with global regulatory environments including GDPR, DORA, the EU AI Act, and emerging security and AI governance requirements across APAC regions.
Experience supporting public sector or FedRAMP aligned environments.
You will operate at the center of AI systems, cloud infrastructure, and global compliance, shaping how security controls are designed and scaled for modern AI platforms. This role offers high ownership, deep technical partnership with engineering, and the opportunity to define what strong GRC looks like at Sierra.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own independent audits and regulatory programs including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, HIPAA, and related frameworks.\n\n - Drive scope definition, readiness assessments, auditor engagement, remediation planning, and executive level reporting.\n\n - Develop a strong working understanding of Sierra’s Conversational AI Platform, model providers, and cloud architecture. Partner with Platform and Agent Engineering to design and operationalize controls across multi cloud environments, infrastructure, inference and data platforms.\n\n - Build a centralized and evolving security controls library mapped to compliance, regulatory and customer requirements. Continuously assess control effectiveness, identify gaps, prioritize risk, and drive remediation that strengthens Sierra’s security and compliance posture.\n\n - Define and enforce security baselines for cloud infrastructure, containerized workloads, Kubernetes, identity, encryption, logging, and network security controls. Partner with engineering teams to integrate security requirements into configuration and change management.\n\n - Design and operate automated compliance workflows using AI, infrastructure as code, and security tooling to reduce manual effort, improve control assurance, and scale with platform evolution.\n\n\nWHO YOU’LL WORK WITH\n\nYou will act as a strategic partner to Platform, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity.\n\n\n\n\nWHAT YOU’LL BRING\n\n - 8+ years of experience in security compliance or GRC or security adjacent roles within fast growing technology companies.\n\n - Deep expertise in security compliance frameworks including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, and similar regulatory environments.\n\n - A systems oriented and engineering focused GRC mindset, with the ability to reason about cloud architecture, data flows, and control effectiveness alongside engineers.\n\n - Experience owning complex audits and driving risk based remediation across distributed teams.\n\n - Hands-on experience with multi-cloud infrastructure (AWS, Azure, GCP).\n\n - Strong experience implementing and automating security controls across cloud infrastructure, configuration management, container security, Kubernetes, encryption, identity, and authentication systems.\n\n - Ability to clearly communicate compliance requirements internally to engineering teams and externally to customers in a technically credible way.\n\n - Relevant certifications such as CISSP, CISA, PCI ISA, ISO 27001 Lead Auditor, or equivalent experience.\n\n\nEVEN BETTER...\n\n - Experience supporting AI platforms, fintech, healthcare, or other highly regulated environments.\n\n - Familiarity with global regulatory environments including GDPR, DORA, the EU AI Act, and emerging security and AI governance requirements across APAC regions.\n\n - Experience supporting public sector or FedRAMP aligned environments.\n\n\nWHY JOIN US?\n\nYou will operate at the center of AI systems, cloud infrastructure, and global compliance, shaping how security controls are designed and scaled for modern AI platforms. This role offers high ownership, deep technical partnership with engineering, and the opportunity to define what strong GRC looks like at Sierra.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f3308520-6d7d-45ac-b96d-3f5a5012e6c9","title":"Software Engineer, Agent - Healthcare","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}}],"publishedAt":"2026-09-23T17:05:12.660+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f3308520-6d7d-45ac-b96d-3f5a5012e6c9","applyUrl":"https://jobs.ashbyhq.com/sierra/f3308520-6d7d-45ac-b96d-3f5a5012e6c9/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Design and deliver production-grade AI agents for healthcare: You'll build and ship highly performant, reliable, and empathetic AI agents that handle sensitive patient and member interactions. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments serving healthcare payers, providers, and platforms.
Partner with healthcare leaders: You'll work directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their most pressing challenges - from managing high call volumes to reducing administrative burden and building AI agents that transform how they operate at scale.
Navigate healthcare complexity: You’ll develop deep expertise in healthcare systems and workflows, including integrations across EHR and patient access platforms, payer and provider operations, and common healthcare data and interoperability standards. You’ll become fluent in the nuances of benefits and eligibility, claims and billing, scheduling and intake, and translate that understanding into exceptional, trustworthy AI experiences.
Build the future of the platform: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare.
These are examples of projects our healthcare team has worked on:
Build AI agents for major health insurance networks that handle detailed questions such as, \"What's my co-pay for a primary care visit?\" and \"How many physical therapy sessions do I have left?\"
Develop voice and chat agents for healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location;
Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics;
Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates;
Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility - all while maintaining HIPAA compliance and strong PHI/data privacy safeguards.
Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions;
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Genuine interest in healthcare and improving patient/member experiences.
Experience in healthcare technology, health IT or working with healthcare organizations
Familiarity with healthcare systems: Major EHR ecosystems (e.g., Epic, Cerner/Oracle Health, athenahealth); X12 EDI transactions and clearinghouse workflows; scheduling/patient access, practice management, and contact center platforms.
Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy).
Experience building or deploying AI/LLM systems in production.
Have been a founder or founding engineer—you know what it means to balance craft, ownership, and speed.
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering.
Prior experience with React, TypeScript, and/or Go.
Previous roles where you interfaced with customers or led technical projects with external stakeholders.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Design and deliver production-grade AI agents for healthcare: You'll build and ship highly performant, reliable, and empathetic AI agents that handle sensitive patient and member interactions. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands.\n\n - Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments serving healthcare payers, providers, and platforms.\n\n - Partner with healthcare leaders: You'll work directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their most pressing challenges - from managing high call volumes to reducing administrative burden and building AI agents that transform how they operate at scale.\n\n - Navigate healthcare complexity: You’ll develop deep expertise in healthcare systems and workflows, including integrations across EHR and patient access platforms, payer and provider operations, and common healthcare data and interoperability standards. You’ll become fluent in the nuances of benefits and eligibility, claims and billing, scheduling and intake, and translate that understanding into exceptional, trustworthy AI experiences.\n\n - Build the future of the platform: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare.\n\n\nEXAMPLE PROJECTS\n\nThese are examples of projects our healthcare team has worked on:\n\n - Build AI agents for major health insurance networks that handle detailed questions such as, \"What's my co-pay for a primary care visit?\" and \"How many physical therapy sessions do I have left?\"\n\n - Develop voice and chat agents for healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location;\n\n - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics;\n\n - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates;\n\n - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility - all while maintaining HIPAA compliance and strong PHI/data privacy safeguards.\n\n - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions;\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Genuine interest in healthcare and improving patient/member experiences.\n\n\nEVEN BETTER...\n\n - Experience in healthcare technology, health IT or working with healthcare organizations\n\n - Familiarity with healthcare systems: Major EHR ecosystems (e.g., Epic, Cerner/Oracle Health, athenahealth); X12 EDI transactions and clearinghouse workflows; scheduling/patient access, practice management, and contact center platforms.\n\n - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy).\n\n - Experience building or deploying AI/LLM systems in production.\n\n - Have been a founder or founding engineer—you know what it means to balance craft, ownership, and speed.\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering.\n\n - Prior experience with React, TypeScript, and/or Go.\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"bb4e7a94-5a6c-4dd0-8121-8c95a94c14b6","title":"Senior Commercial Counsel","department":"Legal","team":"Legal","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-14T18:11:05.351+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/bb4e7a94-5a6c-4dd0-8121-8c95a94c14b6","applyUrl":"https://jobs.ashbyhq.com/sierra/bb4e7a94-5a6c-4dd0-8121-8c95a94c14b6/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We’re hiring a Senior Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact.
Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus.
Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability.
Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so.
Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed. As the team grows, you will train and mentor more junior members.
Judgement: Understand risk in the context of a hyper-scaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement calls, and you will be empowered to do so.
Approach: A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others.
Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives.
6+ years of legal experience, with a combination of both large law firm and in-house experience at a tech company. While we are looking for a Senior Legal Counsel, we are open to considering exceptional candidates with less experience as Commercial Counsel.
A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software.
Strong communication skills and the ability to partner with both legal and non-legal stakeholders.
A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment.
Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions.
A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues.
Significant law firm experience at a top-tier, internationally recognized law firm.
Experience working at a high-growth startup and operating with a sense of ownership.
Industry specific knowledge in any of the following: Financial Services, Healthcare, Telecoms, Insurance and/or Consumer.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nWe’re hiring a Senior Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact.\n\n - Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus.\n\n - Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability.\n\n - Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so.\n\n - Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed. As the team grows, you will train and mentor more junior members.\n\n - Judgement: Understand risk in the context of a hyper-scaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement calls, and you will be empowered to do so.\n\n - Approach: A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others.\n\n - Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives.\n\n\nWHAT YOU’LL BRING\n\n - 6+ years of legal experience, with a combination of both large law firm and in-house experience at a tech company. While we are looking for a Senior Legal Counsel, we are open to considering exceptional candidates with less experience as Commercial Counsel.\n\n - A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software.\n\n - Strong communication skills and the ability to partner with both legal and non-legal stakeholders.\n\n - A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment.\n\n\nEVEN BETTER…\n\n - Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions.\n\n - A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues.\n\n - Significant law firm experience at a top-tier, internationally recognized law firm.\n\n - Experience working at a high-growth startup and operating with a sense of ownership.\n\n - Industry specific knowledge in any of the following: Financial Services, Healthcare, Telecoms, Insurance and/or Consumer.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f64a5b9d-9650-45ca-8596-bc845e9d8d10","title":"Enterprise Sales Engineer","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"Sydney","secondaryLocations":[],"publishedAt":"2026-06-08T06:46:18.795+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Australia","addressLocality":"Sydney"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f64a5b9d-9650-45ca-8596-bc845e9d8d10","applyUrl":"https://jobs.ashbyhq.com/sierra/f64a5b9d-9650-45ca-8596-bc845e9d8d10/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d48840fa-f567-482b-af77-afa4df4d0bce","title":"Enterprise Sales Director","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:12:51.191+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d48840fa-f567-482b-af77-afa4df4d0bce","applyUrl":"https://jobs.ashbyhq.com/sierra/d48840fa-f567-482b-af77-afa4df4d0bce/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"cf34359f-1ac3-4eda-aa96-acbdf87fbc3b","title":"Enterprise Sales Director, Financial Services","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:12:19.447+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/cf34359f-1ac3-4eda-aa96-acbdf87fbc3b","applyUrl":"https://jobs.ashbyhq.com/sierra/cf34359f-1ac3-4eda-aa96-acbdf87fbc3b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"49e6bfed-2d22-40eb-a3e3-1dfb10566546","title":"Enterprise Sales Director","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[{"location":"Toronto","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-08-05T04:12:49.376+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/49e6bfed-2d22-40eb-a3e3-1dfb10566546","applyUrl":"https://jobs.ashbyhq.com/sierra/49e6bfed-2d22-40eb-a3e3-1dfb10566546/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"43765060-50c1-4574-8134-428facdb388b","title":"Enterprise Sales Director - Majors","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[{"location":"Toronto","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-07-22T02:47:30.170+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/43765060-50c1-4574-8134-428facdb388b","applyUrl":"https://jobs.ashbyhq.com/sierra/43765060-50c1-4574-8134-428facdb388b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"631848ec-1a74-4067-8b9f-cd04a71aab6d","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Toronto","secondaryLocations":[],"publishedAt":"2026-03-01T02:13:14.422+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/631848ec-1a74-4067-8b9f-cd04a71aab6d","applyUrl":"https://jobs.ashbyhq.com/sierra/631848ec-1a74-4067-8b9f-cd04a71aab6d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"85e1d0f9-e0d5-4a82-9b30-fa4372e32872","title":"GTM Operations, Agent Development","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-07-21T04:06:36.950+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/85e1d0f9-e0d5-4a82-9b30-fa4372e32872","applyUrl":"https://jobs.ashbyhq.com/sierra/85e1d0f9-e0d5-4a82-9b30-fa4372e32872/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Support the business of Agent Development: Serve as the strategy and operations partner to Agent Dev leadership, and bring the same operational rigor to Agent Dev that powers our Sales organization.
Stand up the operating cadence: Partner with Agent Dev leaders to provide clear visibility into business health, including pipeline, deployment progress, utilization, expansion opportunities, and risks.
Operationalize best practices for enterprise agent deployment: Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises.
Drive account expansion strategy: Work closely with account teams to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.
Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high leverage decisions.
Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage across Agent Dev.
5-7 years of experience in management consulting, investment banking, private equity, or strategy and operations at top-tier technology companies.
Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.
Demonstrated experience supporting sales, post-sales, or commercial teams in a strategy and operations capacity.
Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.
Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.
Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.
A growth mindset, coachability, and willingness to roll up your sleeves. No task is too small if it helps the team win.
Technical fluency and coding comfort: You have built apps or internal tools before and can confidently use AI coding tools such as Claude Code, Cursor, or Codex to create production-ready internal solutions.
Previous 0-1 operating experience at a growth stage technology company.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Support the business of Agent Development: Serve as the strategy and operations partner to Agent Dev leadership, and bring the same operational rigor to Agent Dev that powers our Sales organization.\n\n - Stand up the operating cadence: Partner with Agent Dev leaders to provide clear visibility into business health, including pipeline, deployment progress, utilization, expansion opportunities, and risks.\n\n - Operationalize best practices for enterprise agent deployment: Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises.\n\n - Drive account expansion strategy: Work closely with account teams to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.\n\n - Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high leverage decisions.\n\n - Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage across Agent Dev.\n\n\nWHAT YOU’LL BRING\n\n - 5-7 years of experience in management consulting, investment banking, private equity, or strategy and operations at top-tier technology companies.\n\n - Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.\n\n - Demonstrated experience supporting sales, post-sales, or commercial teams in a strategy and operations capacity.\n\n - Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.\n\n - Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.\n\n - Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.\n\n - A growth mindset, coachability, and willingness to roll up your sleeves. No task is too small if it helps the team win.\n\n\nEVEN BETTER...\n\n - Technical fluency and coding comfort: You have built apps or internal tools before and can confidently use AI coding tools such as Claude Code, Cursor, or Codex to create production-ready internal solutions.\n\n - Previous 0-1 operating experience at a growth stage technology company.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"65eb2c63-c936-4e8e-87e7-ea080dcdca73","title":"Product Manager, Agent Development - Healthcare","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-02-28T00:02:52.509+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/65eb2c63-c936-4e8e-87e7-ea080dcdca73","applyUrl":"https://jobs.ashbyhq.com/sierra/65eb2c63-c936-4e8e-87e7-ea080dcdca73/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Build enterprise-grade AI agents for healthcare: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands.
Discover where agents will make an impact: Ground-up discovery is a critical part of the role. Work closely with providers, payers, RCMs and pharmaceutical companies to identify new use cases and opportunities for AI Agents to deliver impact for their business. You should be our customer’s trusted advisor, and be able drive strategic decisions for our customers.
Engage with customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the platform and healthcare roadmap: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare.
These are examples of projects our healthcare team has worked on:
Develop net new agentic healthcare products that can cut costs and drive revenue in the healthcare ecosystem.
Build AI agents for major health insurance networks that handle detailed questions like \"what's my co-pay for a primary care visit?\" and \"how many physical therapy sessions do I have left?\"
Develop voice and chat agents for nonprofit healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location
Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics
Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates
Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility.
Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Degree in a technical or related field, or equivalent professional experience.
Genuine interest in healthcare and improving patient/member experiences
Experience in healthcare technology, health IT or working with healthcare organizations
Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy)
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents for healthcare: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands.\n\n - Discover where agents will make an impact: Ground-up discovery is a critical part of the role. Work closely with providers, payers, RCMs and pharmaceutical companies to identify new use cases and opportunities for AI Agents to deliver impact for their business. You should be our customer’s trusted advisor, and be able drive strategic decisions for our customers.\n\n - Engage with customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the platform and healthcare roadmap: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare.\n\n\nEXAMPLE PROJECTS\n\nThese are examples of projects our healthcare team has worked on:\n\n - Develop net new agentic healthcare products that can cut costs and drive revenue in the healthcare ecosystem.\n\n - Build AI agents for major health insurance networks that handle detailed questions like \"what's my co-pay for a primary care visit?\" and \"how many physical therapy sessions do I have left?\"\n\n - Develop voice and chat agents for nonprofit healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location\n\n - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics\n\n - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates\n\n - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility.\n\n - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n - Genuine interest in healthcare and improving patient/member experiences\n\n\nEVEN BETTER...\n\n - Experience in healthcare technology, health IT or working with healthcare organizations\n\n - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy)\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"2bba25d3-f5c1-4d84-b3fb-846b40597ff5","title":"Security and Compliance Manager","department":"Security Programs & GRC","team":"Security Programs & GRC","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-03-13T19:45:16.471+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/2bba25d3-f5c1-4d84-b3fb-846b40597ff5","applyUrl":"https://jobs.ashbyhq.com/sierra/2bba25d3-f5c1-4d84-b3fb-846b40597ff5/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Act as a primary point of accountability for customer trust enablement, including participation in customer meetings, security reviews and AI governance.
Contribute to AI Governance including building guardrails to align with AI regulations (EU AI Act, ISO 42001, NIST AI RMF and local EU laws).
Partner closely with Legal and Privacy to interpret regulatory requirements and support complex, security-sensitive contractual discussions, escalating risks and tradeoffs appropriately.
Collaborate with Engineering and Product to ensure expectations are reflected in system design and operational effectiveness.
Translate regulatory and privacy expectations into scalable, region-aware technical controls across model governance, agent security and safety, and data handling.
Own and evolve customer-facing trust materials and narratives related to AI, privacy, and security.
Represent Sierra in customer audits and formal assessments, clearly explaining security posture, governance decisions, and risk management approaches.
Support resilience and response expectations as part of broader governance, with an emphasis on learning and continuous improvement.
Continuously improve trust by identifying opportunities to streamline workflows, increase automation, and improve signal quality, while maintaining a high bar for accuracy and quality.
You will act as a strategic partner to Platform, Security, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity.
8+ years of experience in security compliance, privacy, or regulatory roles in SaaS, fintech, or AI companies.
Deep experience with EU regulatory frameworks, including GDPR, DORA, EU AI Act and emerging AI regulations, paired with strong awareness of US and APAC regulatory norms.
Demonstrated ability to operate globally understanding where requirements must diverge and where alignment is possible.
Experience engaging directly with enterprise and regulated customers as a trusted representative of security, privacy, and compliance.
Ability to translate abstract or evolving regulatory requirements into defensible, real-world practices.
Comfort operating in ambiguity, making reasoned judgment calls, and clearly articulating rationale and tradeoffs.
Strong written and verbal communication skills, including close collaboration with Legal and external stakeholders.
Direct experience preparing for or operationalizing DORA, EU AI Act or ISO/IEC 42001.
Experience working in and/or supporting fintech or AI companies globally
Familiarity with AI governance frameworks such as NIST AI RMF or CSA AI controls.
Experience navigating cross-border data transfer, residency, and localization consideration in a multi-cloud environment.
Prior experience in customer-facing, sales-adjacent, or deal-support contexts.
Experience automating global security and compliance workflows.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Act as a primary point of accountability for customer trust enablement, including participation in customer meetings, security reviews and AI governance.\n\n - Contribute to AI Governance including building guardrails to align with AI regulations (EU AI Act, ISO 42001, NIST AI RMF and local EU laws).\n\n - Partner closely with Legal and Privacy to interpret regulatory requirements and support complex, security-sensitive contractual discussions, escalating risks and tradeoffs appropriately.\n\n - Collaborate with Engineering and Product to ensure expectations are reflected in system design and operational effectiveness.\n\n - Translate regulatory and privacy expectations into scalable, region-aware technical controls across model governance, agent security and safety, and data handling.\n\n - Own and evolve customer-facing trust materials and narratives related to AI, privacy, and security.\n\n - Represent Sierra in customer audits and formal assessments, clearly explaining security posture, governance decisions, and risk management approaches.\n\n - Support resilience and response expectations as part of broader governance, with an emphasis on learning and continuous improvement.\n\n - Continuously improve trust by identifying opportunities to streamline workflows, increase automation, and improve signal quality, while maintaining a high bar for accuracy and quality.\n\n\nWHO YOU’LL WORK WITH\n\nYou will act as a strategic partner to Platform, Security, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity.\n\n\n\n\nWHAT YOU’LL BRING\n\n - 8+ years of experience in security compliance, privacy, or regulatory roles in SaaS, fintech, or AI companies.\n\n - Deep experience with EU regulatory frameworks, including GDPR, DORA, EU AI Act and emerging AI regulations, paired with strong awareness of US and APAC regulatory norms.\n\n - Demonstrated ability to operate globally understanding where requirements must diverge and where alignment is possible.\n\n - Experience engaging directly with enterprise and regulated customers as a trusted representative of security, privacy, and compliance.\n\n - Ability to translate abstract or evolving regulatory requirements into defensible, real-world practices.\n\n - Comfort operating in ambiguity, making reasoned judgment calls, and clearly articulating rationale and tradeoffs.\n\n - Strong written and verbal communication skills, including close collaboration with Legal and external stakeholders.\n\n\nEVEN BETTER...\n\n - Direct experience preparing for or operationalizing DORA, EU AI Act or ISO/IEC 42001.\n\n - Experience working in and/or supporting fintech or AI companies globally\n\n - Familiarity with AI governance frameworks such as NIST AI RMF or CSA AI controls.\n\n - Experience navigating cross-border data transfer, residency, and localization consideration in a multi-cloud environment.\n\n - Prior experience in customer-facing, sales-adjacent, or deal-support contexts.\n\n - Experience automating global security and compliance workflows.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"39355227-d7a2-4066-b930-2bf2eeebc20c","title":"Enterprise Sales Engineer (Spain)","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"Madrid","secondaryLocations":[],"publishedAt":"2026-09-22T08:31:55.375+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Spain","addressLocality":"Madrid"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/39355227-d7a2-4066-b930-2bf2eeebc20c","applyUrl":"https://jobs.ashbyhq.com/sierra/39355227-d7a2-4066-b930-2bf2eeebc20c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Exceptional verbal and written communication abilities. Professional fluency in both Spanish and English.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
AI-related experience (or experience in a similarly modern and highly technical industry).
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Exceptional verbal and written communication abilities. Professional fluency in both Spanish and English.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (or experience in a similarly modern and highly technical industry).\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8e477331-3525-4e87-b311-e500f0fa61e9","title":"Enterprise Sales Director (ANZ)","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Sydney","secondaryLocations":[],"publishedAt":"2026-03-24T03:49:36.349+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Australia","addressLocality":"Sydney"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8e477331-3525-4e87-b311-e500f0fa61e9","applyUrl":"https://jobs.ashbyhq.com/sierra/8e477331-3525-4e87-b311-e500f0fa61e9/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical, and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical, and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"99e82c10-977f-4b42-a737-2d9812ce614d","title":"Strategist, Agent Development","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"Sydney","secondaryLocations":[],"publishedAt":"2026-03-24T20:05:11.405+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Australia","addressLocality":"Sydney"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/99e82c10-977f-4b42-a737-2d9812ce614d","applyUrl":"https://jobs.ashbyhq.com/sierra/99e82c10-977f-4b42-a737-2d9812ce614d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ea1b36ce-fba8-4a11-8f37-d880a1f4f14e","title":"Executive Assistant","department":"Operations","team":"Executive Assistant","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-14T13:23:31.185+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ea1b36ce-fba8-4a11-8f37-d880a1f4f14e","applyUrl":"https://jobs.ashbyhq.com/sierra/ea1b36ce-fba8-4a11-8f37-d880a1f4f14e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Proactively manage calendars, including coordinating sales and partnership meetings, discovery calls, legal contract negotiations, etc.
Ensure the effectiveness of meetings by sending preparation and follow-up materials, such as sales agreements, legal documents, etc.
Plan and execute internal events (in-person and virtual), including team offsites, trainings, and team travel weeks. Support external events, including happy hours, sporting events, leadership in market tours, and beyond.
Establish new and improve existing administrative systems and processes while helping build the founding Sierra admin team.
5+ years of Executive Assistant or similar role.
Ability to build relationships and partner effectively with cross-functional teams and external partners.
Excellent time management skills, willingness and ability to quickly shift tasks and priorities, and anticipate the needs of others before they arise.
Ability to organize, analyze, and prioritize workflows, often interpreting and leveraging data.
Willingness and ability to be in the London office 4 days per week and ability to travel with leaders if needed (~est 1x per quarter).
Advanced proficiency with Google Suite & Slack.
Experience in a fast-growing, in-person start-up environment.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Proactively manage calendars, including coordinating sales and partnership meetings, discovery calls, legal contract negotiations, etc.\n\n - Ensure the effectiveness of meetings by sending preparation and follow-up materials, such as sales agreements, legal documents, etc.\n\n - Plan and execute internal events (in-person and virtual), including team offsites, trainings, and team travel weeks. Support external events, including happy hours, sporting events, leadership in market tours, and beyond.\n\n - Establish new and improve existing administrative systems and processes while helping build the founding Sierra admin team.\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of Executive Assistant or similar role.\n\n - Ability to build relationships and partner effectively with cross-functional teams and external partners.\n\n - Excellent time management skills, willingness and ability to quickly shift tasks and priorities, and anticipate the needs of others before they arise.\n\n - Ability to organize, analyze, and prioritize workflows, often interpreting and leveraging data.\n\n - Willingness and ability to be in the London office 4 days per week and ability to travel with leaders if needed (~est 1x per quarter).\n\n - Advanced proficiency with Google Suite & Slack.\n\n\nEVEN BETTER...\n\n - Experience in a fast-growing, in-person start-up environment.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8d4fe1fb-fb7c-40b2-8667-313e61970e46","title":"Regional VP, Sales","department":"Sales","team":"Sales","employmentType":"FullTime","location":"South Korea","secondaryLocations":[],"publishedAt":"2026-08-25T13:36:37.874+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"South Korea"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8d4fe1fb-fb7c-40b2-8667-313e61970e46","applyUrl":"https://jobs.ashbyhq.com/sierra/8d4fe1fb-fb7c-40b2-8667-313e61970e46/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Start Selling - On day zero, you will be a player/coach. Prospect, build pipeline, manage customers, and close deals, We're looking for candidates who are coming from a leadership role, but are open to getting their hands dirty.
Lead & develop a high-performing sales team - Over the next year, you will hire, onboard, and develop AEs across Korea. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team
Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights
Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy
10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.
People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.
Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Communication: Strong English and Korean written and verbal communication.
Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Start Selling - On day zero, you will be a player/coach. Prospect, build pipeline, manage customers, and close deals, We're looking for candidates who are coming from a leadership role, but are open to getting their hands dirty.\n\n - Lead & develop a high-performing sales team - Over the next year, you will hire, onboard, and develop AEs across Korea. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team\n\n - Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights\n\n - Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy\n\n\nWHAT YOU'LL BRING\n\n - 10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.\n\n - Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Communication: Strong English and Korean written and verbal communication.\n\n\nEVEN BETTER...\n\n - Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"787c1efd-2327-46e7-9335-59a20ad4be18","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Sydney","secondaryLocations":[],"publishedAt":"2026-04-13T15:25:27.714+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressCountry":"Australia","addressLocality":"Sydney"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/787c1efd-2327-46e7-9335-59a20ad4be18","applyUrl":"https://jobs.ashbyhq.com/sierra/787c1efd-2327-46e7-9335-59a20ad4be18/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d9c0aa93-e35d-4752-9cef-4c39dcad5365","title":"Deployed Infrastructure Engineer ","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-04-21T22:00:03.218+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d9c0aa93-e35d-4752-9cef-4c39dcad5365","applyUrl":"https://jobs.ashbyhq.com/sierra/d9c0aa93-e35d-4752-9cef-4c39dcad5365/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Forward Deployed Infrastructure Engineer at Sierra, and a founding member of this function, you will own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments. You'll work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra's AI platform infrastructure — ensuring every deployment meets their security, compliance, and operational requirements. In addition, you’ll establish the standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success. This role will define how Sierra scales some of its most complex customer engagements.
Own deployment architecture conversations and execution — designing and implementing deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning.
Manage the full infrastructure lifecycle for some of Sierra’s most critical customers: initial deployment, ongoing upgrades, scaling, and incident support.
Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to make operations repeatable and reliable.
Partner with engineering teams to ensure Sierra's platform is deployable and operable across diverse customer requirements.
Work with customers' platform engineering, security, and DevOps teams to navigate their infrastructure constraints and compliance requirements.
Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans.
4+ years of experience in infrastructure, DevOps, platform engineering, or solutions architecture roles — with significant time spent on customer-facing deployment work.
Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing).
Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes.
Ability to navigate ambiguity with enterprise stakeholders — from platform engineers to CISOs — and turn infrastructure conversations into actionable deployment plans.
Strong operational instincts: you think about upgrades, rollbacks, monitoring, and failure modes from the start, not as an afterthought.
Comfortable working in a fast-moving environment and collaborating across engineering, product, and go-to-market teams.
Degree in Computer Science or a related field, or equivalent professional experience.
Hands-on experience with Go services, GraphQL APIs, or LLM infrastructure in production environments.
Past experience at an early-stage company where you built deployment operations, playbooks, and tooling.
Familiarity with observability and incident management in distributed systems (Prometheus, Grafana, Datadog, or similar).
Experience with CI/CD pipeline design, deployment automation, or infrastructure self-service tooling for enterprise customers.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n\nAs a Forward Deployed Infrastructure Engineer at Sierra, and a founding member of this function, you will own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments. You'll work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra's AI platform infrastructure — ensuring every deployment meets their security, compliance, and operational requirements. In addition, you’ll establish the standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success. This role will define how Sierra scales some of its most complex customer engagements.\n\n\n - Own deployment architecture conversations and execution — designing and implementing deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning.\n\n - Manage the full infrastructure lifecycle for some of Sierra’s most critical customers: initial deployment, ongoing upgrades, scaling, and incident support.\n\n - Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to make operations repeatable and reliable.\n\n - Partner with engineering teams to ensure Sierra's platform is deployable and operable across diverse customer requirements.\n\n - Work with customers' platform engineering, security, and DevOps teams to navigate their infrastructure constraints and compliance requirements.\n\n - Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans.\n\n\n\n\nWHAT YOU'LL BRING\n\n\n\n - 4+ years of experience in infrastructure, DevOps, platform engineering, or solutions architecture roles — with significant time spent on customer-facing deployment work.\n\n - Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing).\n\n - Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes.\n\n - Ability to navigate ambiguity with enterprise stakeholders — from platform engineers to CISOs — and turn infrastructure conversations into actionable deployment plans.\n\n - Strong operational instincts: you think about upgrades, rollbacks, monitoring, and failure modes from the start, not as an afterthought.\n\n - Comfortable working in a fast-moving environment and collaborating across engineering, product, and go-to-market teams.\n\n - Degree in Computer Science or a related field, or equivalent professional experience.\n\n\n\n\nEVEN BETTER…\n\n - Hands-on experience with Go services, GraphQL APIs, or LLM infrastructure in production environments.\n\n - Past experience at an early-stage company where you built deployment operations, playbooks, and tooling.\n\n - Familiarity with observability and incident management in distributed systems (Prometheus, Grafana, Datadog, or similar).\n\n - Experience with CI/CD pipeline design, deployment automation, or infrastructure self-service tooling for enterprise customers.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b90d210e-c622-46c1-a0c3-d3ef3b3696dd","title":"Enterprise Sales Engineer","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"Munich","secondaryLocations":[],"publishedAt":"2026-05-19T17:05:10.178+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Germany","addressLocality":"Munich"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b90d210e-c622-46c1-a0c3-d3ef3b3696dd","applyUrl":"https://jobs.ashbyhq.com/sierra/b90d210e-c622-46c1-a0c3-d3ef3b3696dd/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"140ea7e3-425a-46dd-93e3-a471fab07a4f","title":"Technical Recruiter (Fixed Term Position) ","department":"Operations","team":"Recruiting","employmentType":"Contract","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-05-22T19:44:52.040+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/140ea7e3-425a-46dd-93e3-a471fab07a4f","applyUrl":"https://jobs.ashbyhq.com/sierra/140ea7e3-425a-46dd-93e3-a471fab07a4f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting processes in a fast paced environment , delivering a high-quality experience for candidates, interviewers, and hiring managers
Partner closely with hiring managers as a trusted advisor to define role requirements, develop compelling position profiles, and align on hiring priorities and timelines
Develop and execute targeted sourcing strategies across multiple channels (LinkedIn, referrals, communities, events, etc.) to attract both active and passive technical talent
Proactively identify, engage, and close top technical candidates in a competitive market
Manage and continuously optimize the interview process, ensuring efficiency, consistency, and equitable hiring practices
Track, analyze, and report on key recruiting metrics (pipeline health, time-to-fill, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence
5+ years of full-cycle recruiting experience, preferably in a fast-paced, high-growth tech environment.
Proven ability to develop and execute recruiting strategies that align with business objectives.
A well-established network within the tech industry and a passion for building new connections.
Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.
Proficiency in using recruiting metrics and data to inform decisions and improve processes.
Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.
This is 12-month fixed-term position. The benefits listed below vary and not all apply to fixed-term opportunities.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting processes in a fast paced environment , delivering a high-quality experience for candidates, interviewers, and hiring managers\n\n - Partner closely with hiring managers as a trusted advisor to define role requirements, develop compelling position profiles, and align on hiring priorities and timelines\n\n - Develop and execute targeted sourcing strategies across multiple channels (LinkedIn, referrals, communities, events, etc.) to attract both active and passive technical talent\n\n - Proactively identify, engage, and close top technical candidates in a competitive market\n\n - Manage and continuously optimize the interview process, ensuring efficiency, consistency, and equitable hiring practices\n\n - Track, analyze, and report on key recruiting metrics (pipeline health, time-to-fill, source effectiveness, candidate experience) and share insights with hiring managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of full-cycle recruiting experience, preferably in a fast-paced, high-growth tech environment.\n\n - Proven ability to develop and execute recruiting strategies that align with business objectives.\n\n - A well-established network within the tech industry and a passion for building new connections.\n\n - Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.\n\n - Proficiency in using recruiting metrics and data to inform decisions and improve processes.\n\n - Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.\n\nThis is 12-month fixed-term position. The benefits listed below vary and not all apply to fixed-term opportunities.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"97ca0c70-f371-4167-9908-2adca3464b8d","title":"Healthcare Integrations Architect","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-11T14:23:37.396+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/97ca0c70-f371-4167-9908-2adca3464b8d","applyUrl":"https://jobs.ashbyhq.com/sierra/97ca0c70-f371-4167-9908-2adca3464b8d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Design integrations grounded in real healthcare workflows. Translate customer requirements into clear recommendations on interfaces, data flows, and EHR configuration. Identify assumptions, tradeoffs, and limitations so engineering teams have an actionable implementation plan.
Resolve customer-specific EHR complexity. Understand how each organization configures and operates its EHR, including scheduling rules, patient identity, permissions, and workflow dependencies. Work with customer analysts, vendor teams, and Sierra engineers to investigate unexpected behavior and resolve integration blockers.
Guide integration readiness through go-live. Define customer setup requirements, dependencies, and validation criteria. Guide EHR and IT teams through application registration, access provisioning, environment setup, and workflow testing, partnering with engineers to verify that integrations behave as intended.
Bring EHR expertise to customer discovery. Partner with Sales, Sales Engineering, and Agent Development to assess feasibility, explain integration requirements, and scope achievable projects. Make clear what Sierra supports today and what requires additional configuration or development.
Shape Sierra’s healthcare integration roadmap. Evaluate vendor capabilities, integration programs, and emerging customer needs. Recommend where to invest, distinguishing reusable platform capabilities from customer-specific configuration and implementation work.
Make each implementation easier than the last. Turn deployment experience into reference designs, implementation guides, and internal training. Help teams apply proven approaches and recognize when a customer’s requirements call for a different design.
5+ years of experience in healthcare interoperability or EHR implementation, with direct responsibility for designing or delivering integrations at an EHR vendor, health system, healthcare technology company, or implementation consultancy.
Deep expertise in at least one major EHR ecosystem, such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, or similar systems. You understand its integration options, configuration model, and implementation processes, and can investigate unfamiliar capabilities independently.
Practical knowledge of patient-access workflows, such as scheduling, registration, or referral management. You can explain how operational rules and customer configuration affect what an integration can do.
Technical fluency in healthcare integrations. You can read API documentation, interpret requests and responses, and troubleshoot data and configuration issues. You have hands-on experience with relevant approaches such as FHIR, HL7v2, vendor APIs, or file-based exchange, and can explain when to use them.
A track record of taking third-party integrations through deployment. You have worked through application registration, authentication and permissions, test and production environments, workflow validation, and go-live dependencies.
Clear communication and independent judgment. You can lead discovery with EHR analysts and operational teams, turn incomplete information into an implementation plan, and explain recommendations to software engineers and business stakeholders. You know when to validate an assumption before committing to an approach.
Epic certifications in areas such as Bridges, Cadence, Prelude, or Interconnect, or comparable expertise in another EHR ecosystem.
Experience across multiple EHR vendors or health systems, particularly integrating third-party products into patient-access or contact-center workflows.
Experience using SQL, scripts, or code to investigate integration issues, or working with teams building AI agents for healthcare.
Hands-on software development experience, including building or extending integrations with EHRs or other healthcare systems.
Comfortable contributing directly to integration code, including implementing API calls, troubleshooting failures, and writing tests. Experience with TypeScript, Go, or Python is a plus.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Design integrations grounded in real healthcare workflows. Translate customer requirements into clear recommendations on interfaces, data flows, and EHR configuration. Identify assumptions, tradeoffs, and limitations so engineering teams have an actionable implementation plan.\n\n - Resolve customer-specific EHR complexity. Understand how each organization configures and operates its EHR, including scheduling rules, patient identity, permissions, and workflow dependencies. Work with customer analysts, vendor teams, and Sierra engineers to investigate unexpected behavior and resolve integration blockers.\n\n - Guide integration readiness through go-live. Define customer setup requirements, dependencies, and validation criteria. Guide EHR and IT teams through application registration, access provisioning, environment setup, and workflow testing, partnering with engineers to verify that integrations behave as intended.\n\n - Bring EHR expertise to customer discovery. Partner with Sales, Sales Engineering, and Agent Development to assess feasibility, explain integration requirements, and scope achievable projects. Make clear what Sierra supports today and what requires additional configuration or development.\n\n - Shape Sierra’s healthcare integration roadmap. Evaluate vendor capabilities, integration programs, and emerging customer needs. Recommend where to invest, distinguishing reusable platform capabilities from customer-specific configuration and implementation work.\n\n - Make each implementation easier than the last. Turn deployment experience into reference designs, implementation guides, and internal training. Help teams apply proven approaches and recognize when a customer’s requirements call for a different design.\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of experience in healthcare interoperability or EHR implementation, with direct responsibility for designing or delivering integrations at an EHR vendor, health system, healthcare technology company, or implementation consultancy.\n\n - Deep expertise in at least one major EHR ecosystem, such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, or similar systems. You understand its integration options, configuration model, and implementation processes, and can investigate unfamiliar capabilities independently.\n\n - Practical knowledge of patient-access workflows, such as scheduling, registration, or referral management. You can explain how operational rules and customer configuration affect what an integration can do.\n\n - Technical fluency in healthcare integrations. You can read API documentation, interpret requests and responses, and troubleshoot data and configuration issues. You have hands-on experience with relevant approaches such as FHIR, HL7v2, vendor APIs, or file-based exchange, and can explain when to use them.\n\n - A track record of taking third-party integrations through deployment. You have worked through application registration, authentication and permissions, test and production environments, workflow validation, and go-live dependencies.\n\n - Clear communication and independent judgment. You can lead discovery with EHR analysts and operational teams, turn incomplete information into an implementation plan, and explain recommendations to software engineers and business stakeholders. You know when to validate an assumption before committing to an approach.\n\n\nEVEN BETTER...\n\n - Epic certifications in areas such as Bridges, Cadence, Prelude, or Interconnect, or comparable expertise in another EHR ecosystem.\n\n - Experience across multiple EHR vendors or health systems, particularly integrating third-party products into patient-access or contact-center workflows.\n\n - Experience using SQL, scripts, or code to investigate integration issues, or working with teams building AI agents for healthcare.\n\n - Hands-on software development experience, including building or extending integrations with EHRs or other healthcare systems.\n\n - Comfortable contributing directly to integration code, including implementing API calls, troubleshooting failures, and writing tests. Experience with TypeScript, Go, or Python is a plus.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"0b6fd623-0dc8-4a91-8d62-f1901272490c","title":"Recruiting Manager","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"Tokyo","secondaryLocations":[],"publishedAt":"2026-07-28T13:30:46.326+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Japan"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/0b6fd623-0dc8-4a91-8d62-f1901272490c","applyUrl":"https://jobs.ashbyhq.com/sierra/0b6fd623-0dc8-4a91-8d62-f1901272490c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead recruiting across Japan, supporting both technical and non-technical hiring, including Engineering, Product Management, Sales, G&A, and leadership roles.
Build and develop a high-performing recruiting team while fostering a culture of excellence, collaboration, and continuous improvement.
Partner closely with senior leaders to translate business priorities into scalable hiring strategies and market plans.
Serve as a trusted advisor on the Japan talent market, providing insights on the competitive landscape, compensation trends, hiring strategies, and organizational design.
Develop innovative sourcing strategies to attract exceptional talent.
Personally recruit and close senior and business-critical hires when needed.
Continuously improve recruiting operations, interview quality, and candidate experience while ensuring hiring decisions remain thoughtful, efficient, and consistent.
Partner cross-functionally with People, Compensation, Immigration, and Recruiting Operations to support the continued growth of our Japan business.
Use recruiting data and market insights to influence hiring priorities, capacity planning, and long-term workforce strategy.
10+ years of recruiting experience, including experience leading recruiting teams in Japan.
Experience hiring across both technical and business functions within high-growth technology companies.
Deep understanding of the Japan talent market, including experience building engineering and enterprise sales organizations.
Strong people leadership skills with a track record of coaching and developing recruiters.
Experience partnering directly with executives and senior hiring managers on organizational growth and talent strategy.
Excellent judgment, prioritization, and problem-solving skills in fast-changing environments.
Passion for delivering an exceptional candidate and hiring manager experience.
Native fluency in Japanese and strong written and verbal English communication, with the ability to influence and build trust across global and local stakeholders.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Lead recruiting across Japan, supporting both technical and non-technical hiring, including Engineering, Product Management, Sales, G&A, and leadership roles.\n\n - Build and develop a high-performing recruiting team while fostering a culture of excellence, collaboration, and continuous improvement.\n\n - Partner closely with senior leaders to translate business priorities into scalable hiring strategies and market plans.\n\n - Serve as a trusted advisor on the Japan talent market, providing insights on the competitive landscape, compensation trends, hiring strategies, and organizational design.\n\n - Develop innovative sourcing strategies to attract exceptional talent.\n\n - Personally recruit and close senior and business-critical hires when needed.\n\n - Continuously improve recruiting operations, interview quality, and candidate experience while ensuring hiring decisions remain thoughtful, efficient, and consistent.\n\n - Partner cross-functionally with People, Compensation, Immigration, and Recruiting Operations to support the continued growth of our Japan business.\n\n - Use recruiting data and market insights to influence hiring priorities, capacity planning, and long-term workforce strategy.\n\n\nWHAT YOU’LL BRING\n\n - 10+ years of recruiting experience, including experience leading recruiting teams in Japan.\n\n - Experience hiring across both technical and business functions within high-growth technology companies.\n\n - Deep understanding of the Japan talent market, including experience building engineering and enterprise sales organizations.\n\n - Strong people leadership skills with a track record of coaching and developing recruiters.\n\n - Experience partnering directly with executives and senior hiring managers on organizational growth and talent strategy.\n\n - Excellent judgment, prioritization, and problem-solving skills in fast-changing environments.\n\n - Passion for delivering an exceptional candidate and hiring manager experience.\n\n - Native fluency in Japanese and strong written and verbal English communication, with the ability to influence and build trust across global and local stakeholders.\n\n\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8fe2757e-13e9-47e0-9d5a-90b2596a975c","title":"Software Engineer, Payments Infrastructure","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-02T17:38:25.749+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8fe2757e-13e9-47e0-9d5a-90b2596a975c","applyUrl":"https://jobs.ashbyhq.com/sierra/8fe2757e-13e9-47e0-9d5a-90b2596a975c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
The agent must collect and use a card number but can never see it. This work sits across four hard technical domains: payments, security, real-time voice, and LLMs. Voice is the core challenge. A caller speaks or types a card number in a live, low-latency audio stream, and the digits must never reach the model, while the model stays on the call.
Sierra owns every system that touches card data, and one small team owns it end to end across three workstreams: Platform, Product, and Safety & Integrity. Customers keep their own telephony and payment gateways. Payments is live in production for some of the largest consumer enterprises, on a platform that handles hundreds of millions of calls a year. The platform is certified to PCI DSS Level 1.
Build real-time card capture for voice: intercept keypad and spoken digits in a live audio stream, upstream of the agent runtime in a network-segmented environment, while the LLM stays live on the call. Make it work across every telephony provider and protocol Sierra supports.
Build and extend the tokenization platform: agents receive and send short-lived tokens, and the platform swaps a token for the real value only when it calls the customer's payment gateway.
Own the payments egress control plane: every destination for card data is approved, versioned with the agent release, and enforced by infrastructure below the application, not by convention.
Make payment actions correct: an at-most-once action primitive in the Agent SDK, validated amounts and items, and monitoring that compares what the agent said about a payment with what really happened.
Keep card data out of places it should not be: deterministic detection in the agent's hot path that catches what general-purpose models miss. No LLM, including any we build ourselves, ever sees a plaintext card number.
Make payments self-serve: one payments API across Agent Studio, the Agent SDK, and Ghostwriter, Sierra's agent-building agent; gateway middleware that developers write against tokens; and support for single-tenant and customer-cloud deployments. Any team can add payments to an agent without a payments engineer in the loop.
Grow the platform beyond cards: extend tokenization into a privacy vault for all PII.
5+ years building backend, platform, or infrastructure systems, with a track record of shipping and operating high-reliability services in production.
A deep security instinct. You design as though every component will eventually be compromised, and you reason naturally about blast radius, least privilege, and making bad states impossible rather than reacting to them.
Rigor about correctness under failure: retries, idempotency, at-most-once behavior, and clear handling of timeouts and unclear results from external systems.
Fluency in a systems language (we use Go) and comfort owning critical systems end to end, from design through production and on-call.
Range and ownership. You like a small team with broad scope, you build clean abstractions over messy external systems, and you're never satisfied solving a problem once per customer.
Clear communication. You can explain a design or a risk to other engineering teams and to non-engineers.
Degree in Computer Science or a related field, or equivalent professional experience.
You don't need payments experience. The engineers who built this platform came from backend, infrastructure, and security work, not payments. We care more about how you build correct, secure systems than about the word \"payments\" on your resume.
Real-time or streaming systems: voice, telephony, media, or low-latency pipelines.
Applied cryptography and key management, network isolation, egress control, or cloud security.
Platforms other engineering teams build on, such as APIs, SDKs, and self-serve developer services.
Deployments into customer-owned clouds or single-tenant environments.
Customer-facing technical work, such as architecture reviews with customers.
Setting technical direction on ambiguous, high-stakes problems.
Payments, fintech, or another sensitive-data domain such as healthcare or identity.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nThe agent must collect and use a card number but can never see it. This work sits across four hard technical domains: payments, security, real-time voice, and LLMs. Voice is the core challenge. A caller speaks or types a card number in a live, low-latency audio stream, and the digits must never reach the model, while the model stays on the call.\n\nSierra owns every system that touches card data, and one small team owns it end to end across three workstreams: Platform, Product, and Safety & Integrity. Customers keep their own telephony and payment gateways. Payments is live in production for some of the largest consumer enterprises, on a platform that handles hundreds of millions of calls a year. The platform is certified to PCI DSS Level 1.\n\n - Build real-time card capture for voice: intercept keypad and spoken digits in a live audio stream, upstream of the agent runtime in a network-segmented environment, while the LLM stays live on the call. Make it work across every telephony provider and protocol Sierra supports.\n\n - Build and extend the tokenization platform: agents receive and send short-lived tokens, and the platform swaps a token for the real value only when it calls the customer's payment gateway.\n\n - Own the payments egress control plane: every destination for card data is approved, versioned with the agent release, and enforced by infrastructure below the application, not by convention.\n\n - Make payment actions correct: an at-most-once action primitive in the Agent SDK, validated amounts and items, and monitoring that compares what the agent said about a payment with what really happened.\n\n - Keep card data out of places it should not be: deterministic detection in the agent's hot path that catches what general-purpose models miss. No LLM, including any we build ourselves, ever sees a plaintext card number.\n\n - Make payments self-serve: one payments API across Agent Studio, the Agent SDK, and Ghostwriter, Sierra's agent-building agent; gateway middleware that developers write against tokens; and support for single-tenant and customer-cloud deployments. Any team can add payments to an agent without a payments engineer in the loop.\n\n - Grow the platform beyond cards: extend tokenization into a privacy vault for all PII.\n\n\nWHAT YOU'LL BRING\n\n - 5+ years building backend, platform, or infrastructure systems, with a track record of shipping and operating high-reliability services in production.\n\n - A deep security instinct. You design as though every component will eventually be compromised, and you reason naturally about blast radius, least privilege, and making bad states impossible rather than reacting to them.\n\n - Rigor about correctness under failure: retries, idempotency, at-most-once behavior, and clear handling of timeouts and unclear results from external systems.\n\n - Fluency in a systems language (we use Go) and comfort owning critical systems end to end, from design through production and on-call.\n\n - Range and ownership. You like a small team with broad scope, you build clean abstractions over messy external systems, and you're never satisfied solving a problem once per customer.\n\n - Clear communication. You can explain a design or a risk to other engineering teams and to non-engineers.\n\n - Degree in Computer Science or a related field, or equivalent professional experience.\n\nYou don't need payments experience. The engineers who built this platform came from backend, infrastructure, and security work, not payments. We care more about how you build correct, secure systems than about the word \"payments\" on your resume.\n\n\nEVEN BETTER…\n\n - Real-time or streaming systems: voice, telephony, media, or low-latency pipelines.\n\n - Applied cryptography and key management, network isolation, egress control, or cloud security.\n\n - Platforms other engineering teams build on, such as APIs, SDKs, and self-serve developer services.\n\n - Deployments into customer-owned clouds or single-tenant environments.\n\n - Customer-facing technical work, such as architecture reviews with customers.\n\n - Setting technical direction on ambiguous, high-stakes problems.\n\n - Payments, fintech, or another sensitive-data domain such as healthcare or identity.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"26d1f737-94a6-497e-a672-93f4f652fca7","title":"Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"Tokyo","secondaryLocations":[],"publishedAt":"2026-06-03T10:01:02.292+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Japan"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/26d1f737-94a6-497e-a672-93f4f652fca7","applyUrl":"https://jobs.ashbyhq.com/sierra/26d1f737-94a6-497e-a672-93f4f652fca7/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting process, creating a positive candidate, interviewer, and Hiring Manager experience
Be a strategic partner, working closely with Hiring Managers to develop position profiles, understand overall needs and requirements, as well as the candidate market
Create and execute sourcing strategies across multiple channels for both active and passive candidates for each role
Track and analyze recruiting metrics and report to Hiring Managers and Sierra leadership on a regular cadence
5-8+ years of full-cycle recruiting experience at a high-growth tech company, with early-stage start-up experience preferred
Demonstrated expertise in recruiting, outbound sourcing, and closing candidates across technical and business roles
Ability to build impactful relationships with hiring managers and interview teams
Strong English and Japanese written and verbal communication
Experience with Ashby ATS
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting process, creating a positive candidate, interviewer, and Hiring Manager experience\n\n - Be a strategic partner, working closely with Hiring Managers to develop position profiles, understand overall needs and requirements, as well as the candidate market\n\n - Create and execute sourcing strategies across multiple channels for both active and passive candidates for each role\n\n - Track and analyze recruiting metrics and report to Hiring Managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5-8+ years of full-cycle recruiting experience at a high-growth tech company, with early-stage start-up experience preferred\n\n - Demonstrated expertise in recruiting, outbound sourcing, and closing candidates across technical and business roles\n\n - Ability to build impactful relationships with hiring managers and interview teams\n\n - Strong English and Japanese written and verbal communication\n\n\nEVEN BETTER...\n\n - Experience with Ashby ATS\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"78c5dce4-3670-4c9b-a666-98f435c56324","title":"Software Engineer, Context Engine","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-05T18:26:10.009+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/78c5dce4-3670-4c9b-a666-98f435c56324","applyUrl":"https://jobs.ashbyhq.com/sierra/78c5dce4-3670-4c9b-a666-98f435c56324/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
You’ll join a full-stack data team building the systems making our AI agents measurably smarter with every interaction, building the real-time pipelines, analytics products, and deep personalization primitives that turn millions of conversations into business outcomes. You’ll work across these areas:
Data Foundations: Architect and build our core platform to handle data at scale with low latency. This includes our real-time eventing infrastructure, streaming and batch ETL pipelines, and our Iceberg-based data lakehouse. You will own the systems for interactive OLAP querying, orchestration, and experimentation, ensuring our data is trustworthy, fast, and easy to use for the entire organization.
Memory & Personalization: Power the next generation of intelligent experiences. You will develop the systems for long-term agent memory, build reusable Customer Data Platform (CDP) primitives, and implement the optimization loops that allow our agents to personalize interactions and demonstrably lift business outcomes.
We’re excited to meet candidates who bring depth in one of these areas:
Platform Engineering
You have designed, built, and operated large-scale data systems, processing terabytes or petabytes of data with technologies like Spark, Flink, Trino/Presto, and data lakehouse formats like Iceberg or Hudi.
You possess strong backend and distributed systems fundamentals in a language like Go, Scala, or Python. You understand the trade-offs of different storage engines, query plans, and data serialization formats.
You have a history of implementing pragmatic data governance, lineage, and testing. You’ve built platforms that are cost-aware, highly operable, and a delight for other engineers to build upon.
You're well-versed in data modeling best practices (dimensional modeling, star/snowflake schemas, slowly changing dimensions) and know how to optimize analytical query patterns for both traditional OLAP systems and modern cloud data warehouses.
Product Engineering
You have a portfolio of shipped data products, including analytics dashboards, data visualization tools, or alerting and exploration systems.
You are a skilled full-stack engineer (e.g., TypeScript/React and a service layer like Go), with a keen eye for performance, API design, and polish.
You excel at turning ambiguous questions into clear, intuitive interfaces. You have strong product sense around information architecture, handling empty states, and making complex data explainable.
You have practical experience with ML-powered product features, such as personalization, recommendations, or classification systems.
Shared Qualities
Strong software engineering background with 4-7+ years of hands-on development experience in building and shipping production systems or products.
A passion for being on the frontier of AI products.
High agency and a bias to action in a high-autonomy environment.
Degree in Computer Science or related field, or equivalent professional experience.
Deep experience with event streaming platforms (e.g., Kafka, Kinesis) and real-time data processing.
Experience with modern data visualization libraries (e.g., ECharts, D3.js) and the principles of building performant, reusable charting components for complex data.
Production experience with recommender systems or optimization loops (e.g., multi-armed bandits, ranking).
A track record of leading complex technical projects or mentoring other engineers.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nYou’ll join a full-stack data team building the systems making our AI agents measurably smarter with every interaction, building the real-time pipelines, analytics products, and deep personalization primitives that turn millions of conversations into business outcomes. You’ll work across these areas:\n\n - Data Foundations: Architect and build our core platform to handle data at scale with low latency. This includes our real-time eventing infrastructure, streaming and batch ETL pipelines, and our Iceberg-based data lakehouse. You will own the systems for interactive OLAP querying, orchestration, and experimentation, ensuring our data is trustworthy, fast, and easy to use for the entire organization.\n\n - Memory & Personalization: Power the next generation of intelligent experiences. You will develop the systems for long-term agent memory, build reusable Customer Data Platform (CDP) primitives, and implement the optimization loops that allow our agents to personalize interactions and demonstrably lift business outcomes.\n\n\nWHAT YOU'LL BRING\n\nWe’re excited to meet candidates who bring depth in one of these areas:\n\nPlatform Engineering\n\n - You have designed, built, and operated large-scale data systems, processing terabytes or petabytes of data with technologies like Spark, Flink, Trino/Presto, and data lakehouse formats like Iceberg or Hudi.\n\n - You possess strong backend and distributed systems fundamentals in a language like Go, Scala, or Python. You understand the trade-offs of different storage engines, query plans, and data serialization formats.\n\n - You have a history of implementing pragmatic data governance, lineage, and testing. You’ve built platforms that are cost-aware, highly operable, and a delight for other engineers to build upon.\n\n - You're well-versed in data modeling best practices (dimensional modeling, star/snowflake schemas, slowly changing dimensions) and know how to optimize analytical query patterns for both traditional OLAP systems and modern cloud data warehouses.\n\nProduct Engineering\n\n - You have a portfolio of shipped data products, including analytics dashboards, data visualization tools, or alerting and exploration systems.\n\n - You are a skilled full-stack engineer (e.g., TypeScript/React and a service layer like Go), with a keen eye for performance, API design, and polish.\n\n - You excel at turning ambiguous questions into clear, intuitive interfaces. You have strong product sense around information architecture, handling empty states, and making complex data explainable.\n\n - You have practical experience with ML-powered product features, such as personalization, recommendations, or classification systems.\n\nShared Qualities\n\n - Strong software engineering background with 4-7+ years of hands-on development experience in building and shipping production systems or products.\n\n - A passion for being on the frontier of AI products.\n\n - High agency and a bias to action in a high-autonomy environment.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n \n\n\nEVEN BETTER...\n\n - Deep experience with event streaming platforms (e.g., Kafka, Kinesis) and real-time data processing.\n\n - Experience with modern data visualization libraries (e.g., ECharts, D3.js) and the principles of building performant, reusable charting components for complex data.\n\n - Production experience with recommender systems or optimization loops (e.g., multi-armed bandits, ranking).\n\n - A track record of leading complex technical projects or mentoring other engineers.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"802d17c5-fe47-4b44-90e5-65e5e731ff88","title":"Software Engineer, Infrastructure","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-05T18:27:43.314+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/802d17c5-fe47-4b44-90e5-65e5e731ff88","applyUrl":"https://jobs.ashbyhq.com/sierra/802d17c5-fe47-4b44-90e5-65e5e731ff88/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Software Engineer, Infrastructure at Sierra, you will be responsible for designing, building, and maintaining the core systems that make our AI platform possible. You’ll focus on making Sierra’s infrastructure secure, reliable, and scalable, enabling product teams to deliver with speed and confidence.
Ensure the reliability, scalability, and performance of our platform and LLM inference serving as we rapidly grow traffic.
Build and maintain cloud infrastructure using Terraform to ensure scalable, secure, and reproducible environments.
Create and maintain a self-serve infrastructure platform that enables the rest of engineering to deploy and operate services.
Own and evolve CI/CD pipelines and release management, enabling fast, reliable deployments for Sierra’s platform.
Architect and operate distributed systems that leverage distributed databases, retrieval systems, and ML models.
Develop and maintain core data serving abstractions along with authentication and security features (SSO, RBAC, authentication controls).
Navigate and integrate our stack with enterprise customer environments in scalable and maintainable ways.
Enhance observability tooling (metrics, logging, tracing) to provide deep visibility into platform health and performance.
Lead and participate in incident management, improving system resilience through proactive monitoring, root cause analysis, and postmortems.
Strong software engineering background with 5–7+ years of hands-on development experience in highly technical products.
A strong inclination towards building automation, tooling, and platform, along with designing maintainable systems.
Proven experience with cloud platforms (AWS, GCP, or Azure) and infrastructure as code (Terraform preferred).
Hands-on expertise in CI/CD systems, release management, and container orchestration (e.g., Docker, Kubernetes).
Experience with observability tools (Prometheus, Grafana, Datadog, OpenTelemetry, etc.).
Experience in incident response and operating distributed systems in production.
Degree in Computer Science or related field, or equivalent professional experience
Production experience working with LLMs and machine learning models.
Background in distributed systems, running SaaS services at scale, and agentic architecture.
Familiarity with security and authentication protocols (OAuth, SSO, mTLS).
Previous experience in a fast-paced startup environment or platform/infra-focused team.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs a Software Engineer, Infrastructure at Sierra, you will be responsible for designing, building, and maintaining the core systems that make our AI platform possible. You’ll focus on making Sierra’s infrastructure secure, reliable, and scalable, enabling product teams to deliver with speed and confidence.\n\n - Ensure the reliability, scalability, and performance of our platform and LLM inference serving as we rapidly grow traffic.\n\n - Build and maintain cloud infrastructure using Terraform to ensure scalable, secure, and reproducible environments.\n\n - Create and maintain a self-serve infrastructure platform that enables the rest of engineering to deploy and operate services.\n\n - Own and evolve CI/CD pipelines and release management, enabling fast, reliable deployments for Sierra’s platform.\n\n - Architect and operate distributed systems that leverage distributed databases, retrieval systems, and ML models.\n\n - Develop and maintain core data serving abstractions along with authentication and security features (SSO, RBAC, authentication controls).\n\n - Navigate and integrate our stack with enterprise customer environments in scalable and maintainable ways.\n\n - Enhance observability tooling (metrics, logging, tracing) to provide deep visibility into platform health and performance.\n\n - Lead and participate in incident management, improving system resilience through proactive monitoring, root cause analysis, and postmortems.\n\n\nWHAT YOU’LL BRING\n\n - Strong software engineering background with 5–7+ years of hands-on development experience in highly technical products.\n\n - A strong inclination towards building automation, tooling, and platform, along with designing maintainable systems.\n\n - Proven experience with cloud platforms (AWS, GCP, or Azure) and infrastructure as code (Terraform preferred).\n\n - Hands-on expertise in CI/CD systems, release management, and container orchestration (e.g., Docker, Kubernetes).\n\n - Experience with observability tools (Prometheus, Grafana, Datadog, OpenTelemetry, etc.).\n\n - Experience in incident response and operating distributed systems in production.\n\n - Degree in Computer Science or related field, or equivalent professional experience\n\n\nEVEN BETTER…\n\n - Production experience working with LLMs and machine learning models.\n\n - Background in distributed systems, running SaaS services at scale, and agentic architecture.\n\n - Familiarity with security and authentication protocols (OAuth, SSO, mTLS).\n\n - Previous experience in a fast-paced startup environment or platform/infra-focused team.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"5ae78769-a3a1-491c-8b4b-95472f1fb36c","title":"Software Engineer, Product","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-05T18:28:21.257+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/5ae78769-a3a1-491c-8b4b-95472f1fb36c","applyUrl":"https://jobs.ashbyhq.com/sierra/5ae78769-a3a1-491c-8b4b-95472f1fb36c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Agent Architecture: What primitives do we need to build agents that are steerable and verifiable, but also conversational and empathetic? How do we future-proof this as LLMs evolve?
Retrieval: How do we ground answers in a customer’s knowledge base? How do we use retrieved context conversationally, handling cases where the answer is unclear or needs clarification from the user?
Evals: How do we measure an agent’s quality? How do empower our customers to improve agent quality?
Voice: How do we make our chat agents “just work” over the phone? How do we deliver lifelike conversations at low latency?
Simulation & Benchmarking: How can we craft a simulation platform to test AI agents against every real-world scenario imaginable? (See 𝜏-Bench)
Content Management: How do we create intuitive, no-code tools that allow anyone to guide and test AI agents?
Agent Development Lifecycle: How do we adapt traditional software development methodologies to accommodate AI agents’ non-deterministic behavior, natural language interactions, and reliance on large language models? (See Sierra’s ADLC)
Generative Agent Development: How do we accelerate agent creation using generative tools like Cursor and Claude Code? Can we build self-improving systems based on real-world interactions, customer-driven feedback, and self-play?
A passion for being on the frontier of AI products.
Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.
Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.
4+ years hands-on experience building production products and systems.
Experience and comfort to build and ship full-stack solutions.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building AI-powered products.
A sharp eye for design.
Experience with Go and Typescript.
Experience building developer tooling, programming languages, or databases.
Leadership experience on technical projects or teams.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Agent Architecture: What primitives do we need to build agents that are steerable and verifiable, but also conversational and empathetic? How do we future-proof this as LLMs evolve?\n\n - Retrieval: How do we ground answers in a customer’s knowledge base? How do we use retrieved context conversationally, handling cases where the answer is unclear or needs clarification from the user?\n\n - Evals: How do we measure an agent’s quality? How do empower our customers to improve agent quality?\n\n - Voice: How do we make our chat agents “just work” over the phone? How do we deliver lifelike conversations at low latency?\n\n - Simulation & Benchmarking: How can we craft a simulation platform to test AI agents against every real-world scenario imaginable? (See 𝜏-Bench https://sierra.ai/blog/benchmarking-ai-agents)\n\n - Content Management: How do we create intuitive, no-code tools that allow anyone to guide and test AI agents?\n\n - Agent Development Lifecycle: How do we adapt traditional software development methodologies to accommodate AI agents’ non-deterministic behavior, natural language interactions, and reliance on large language models? (See Sierra’s ADLC https://sierra.ai/blog/agent-development-life-cycle)\n\n - Generative Agent Development: How do we accelerate agent creation using generative tools like Cursor and Claude Code? Can we build self-improving systems based on real-world interactions, customer-driven feedback, and self-play?\n\n\nWHAT YOU'LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.\n\n - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.\n\n - 4+ years hands-on experience building production products and systems.\n\n - Experience and comfort to build and ship full-stack solutions.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience building AI-powered products.\n\n - A sharp eye for design.\n\n - Experience with Go and Typescript.\n\n - Experience building developer tooling, programming languages, or databases.\n\n - Leadership experience on technical projects or teams.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9b70b937-9634-4bcd-a10e-2671145f3a07","title":"Software Engineer, Agent Builder","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-05T18:28:46.684+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9b70b937-9634-4bcd-a10e-2671145f3a07","applyUrl":"https://jobs.ashbyhq.com/sierra/9b70b937-9634-4bcd-a10e-2671145f3a07/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Simulation & Benchmarking: How can we craft a simulation platform to test AI agents against every real-world scenario imaginable? (See 𝜏-Bench)
Content Management: How do we create intuitive, no-code tools that allow anyone to guide and test AI agents?
Agent Development Lifecycle: How do we adapt traditional software development methodologies to accommodate AI agents’ non-deterministic behavior, natural language interactions, and reliance on large language models? (See Sierra’s ADLC)
Generative Agent Development: How do we accelerate agent creation using generative tools like Cursor and Claude Code? Can we build self-improving systems based on real-world interactions, customer-driven feedback, and self-play?
A passion for being on the frontier of AI products.
Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.
Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.
4+ years hands-on experience building production products and systems.
Experience and comfort to build and ship full-stack solutions.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building AI-powered products.
A sharp eye for design.
Experience with Go and Typescript.
Experience building developer tooling, programming languages, or databases.
Leadership experience on technical projects or teams.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Simulation & Benchmarking: How can we craft a simulation platform to test AI agents against every real-world scenario imaginable? (See 𝜏-Bench https://sierra.ai/blog/benchmarking-ai-agents)\n\n - Content Management: How do we create intuitive, no-code tools that allow anyone to guide and test AI agents?\n\n - Agent Development Lifecycle: How do we adapt traditional software development methodologies to accommodate AI agents’ non-deterministic behavior, natural language interactions, and reliance on large language models? (See Sierra’s ADLC https://sierra.ai/blog/agent-development-life-cycle)\n\n - Generative Agent Development: How do we accelerate agent creation using generative tools like Cursor and Claude Code? Can we build self-improving systems based on real-world interactions, customer-driven feedback, and self-play?\n\n\nWHAT YOU'LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.\n\n - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.\n\n - 4+ years hands-on experience building production products and systems.\n\n - Experience and comfort to build and ship full-stack solutions.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience building AI-powered products.\n\n - A sharp eye for design.\n\n - Experience with Go and Typescript.\n\n - Experience building developer tooling, programming languages, or databases.\n\n - Leadership experience on technical projects or teams.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8cca0a0d-7359-410b-81ed-331a0bb4667f","title":"Software Engineer, Insights","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-05T18:29:12.015+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8cca0a0d-7359-410b-81ed-331a0bb4667f","applyUrl":"https://jobs.ashbyhq.com/sierra/8cca0a0d-7359-410b-81ed-331a0bb4667f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Reporting & Experimentation: Build a system for analyzing and visualizing millions of data points about agent performance. Enable agent developers to run A/B test their agents to make data-driven decisions about agent behavior.
Data Exploration: Build Explorer, the equivalent of ChatGPT + AI-powered clustering over conversational data.
Monitoring: Build systems for proactively monitoring agents for defects or new patterns.
A passion for being on the frontier of AI products.
Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.
Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.
4+ years hands-on experience building production products and systems.
Experience and comfort to build and ship full-stack solutions.
Degree in Computer Science or related field, or equivalent professional experience.
Experience building AI-powered products.
A sharp eye for design.
Experience with Go and Typescript.
Experience building developer tooling, programming languages, or databases.
Leadership experience on technical projects or teams.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Reporting & Experimentation: Build a system for analyzing and visualizing millions of data points about agent performance. Enable agent developers to run A/B test their agents to make data-driven decisions about agent behavior.\n\n - Data Exploration: Build Explorer, the equivalent of ChatGPT + AI-powered clustering over conversational data.\n\n - Monitoring: Build systems for proactively monitoring agents for defects or new patterns.\n\n\nWHAT YOU'LL BRING\n\n - A passion for being on the frontier of AI products.\n\n - Motivation and high-agency to drive outcomes - we have a high-autonomy culture and each team member has lots of agency to overcome obstacles and achieve customer impact.\n\n - Alignment to our company values throughout your work, notably finding a balance between Craftsmanship, Customer Obsession, and Competitive Intensity.\n\n - 4+ years hands-on experience building production products and systems.\n\n - Experience and comfort to build and ship full-stack solutions.\n\n - Degree in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience building AI-powered products.\n\n - A sharp eye for design.\n\n - Experience with Go and Typescript.\n\n - Experience building developer tooling, programming languages, or databases.\n\n - Leadership experience on technical projects or teams.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"4f0e65ba-b262-4d79-b926-3988f8eb0c00","title":"Product Manager, Agent Development (Brazilian Portuguese speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-06-18T17:23:11.153+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/4f0e65ba-b262-4d79-b926-3988f8eb0c00","applyUrl":"https://jobs.ashbyhq.com/sierra/4f0e65ba-b262-4d79-b926-3988f8eb0c00/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
5-7+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Professional fluency in both Brazilian Portuguese and English.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Professional fluency in both Brazilian Portuguese and English.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ae8840cd-f46e-4c96-87b1-53fedf40f94d","title":"Software Engineer, Agent (Dutch speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-06-10T21:12:57.089+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ae8840cd-f46e-4c96-87b1-53fedf40f94d","applyUrl":"https://jobs.ashbyhq.com/sierra/ae8840cd-f46e-4c96-87b1-53fedf40f94d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in London, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"611a6f2c-b6f8-4dfd-9ae8-4b0b986ac258","title":"Strategist, Agent Development (Dutch speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-06-10T21:13:21.753+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/611a6f2c-b6f8-4dfd-9ae8-4b0b986ac258","applyUrl":"https://jobs.ashbyhq.com/sierra/611a6f2c-b6f8-4dfd-9ae8-4b0b986ac258/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9d54f016-7919-457b-a298-17a536ab8c5c","title":"Strategist, Agent Development (Flemish speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-06T13:59:16.510+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9d54f016-7919-457b-a298-17a536ab8c5c","applyUrl":"https://jobs.ashbyhq.com/sierra/9d54f016-7919-457b-a298-17a536ab8c5c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"8a906ec6-5ec5-4619-82de-7a3c665998f5","title":"Marketing Operations & Analytics Lead","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-12T13:56:38.056+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/8a906ec6-5ec5-4619-82de-7a3c665998f5","applyUrl":"https://jobs.ashbyhq.com/sierra/8a906ec6-5ec5-4619-82de-7a3c665998f5/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
The role
This is a foundational role on Sierra's Operations team, sitting at the intersection of marketing and GTM. As Marketing Operations and Analytics Lead, you'll own two things: the measurement infrastructure that connects marketing programs to pipeline and revenue; and the operational processes that make the marketing engine run efficiently and at scale.
What you'll do
Full-funnel attribution: Design and own Sierra's marketing attribution framework, connecting campaigns, events, content, and demand gen programs to pipeline generation and ultimately LTC conversions.
Pipeline analytics: Partner with Marketing and Sales to analyze pipegen by vertical, region, and segment. Track conversion rates at each stage and surface where marketing programs are—and aren't—generating high-quality opportunities.
Performance reporting: Build and maintain the marketing team's core performance dashboards—campaign ROI, event pipeline influence, channel mix, lead quality, and funnel velocity.
ICP & account intelligence: Develop data-driven ICP scoring and account prioritization models to focus marketing investment on segments with the highest win rates and ASPs. Integrate signals from first-party and third-party intent sources to keep targeting sharp.
Experiment design & optimization: Design rigorous A/B and multivariate tests across marketing channels. Establish the statistical standards the team uses to evaluate new programs; translate results into clear, actionable recommendations—not just p-values.
Lead management & routing: Define and maintain lead scoring models, MQL thresholds, and routing logic from first touch to Sales handoff. Partner with Sales to ensure lead quality, minimize friction, and continuously improve conversion from MQL to pipeline.
Campaign operations: Own the operational infrastructure behind campaign execution—email programs, landing page workflows, event lead capture, and list management. Build processes that let the demand gen and events teams move quickly without creating data debt.
Cross-functional partnership: Serve as the analytical and operational bridge between Marketing, GTM Ops, Finance, and Sales leadership—ensuring marketing metrics are aligned with company PG, POC, and ARR targets; contribute to quarterly business reviews (QBRs) and annual planning with marketing-specific performance analysis and forecasts
What you'll bring
12+ years spanning marketing analytics and marketing operations
Deep expertise in attribution modeling, multi-touch funnel analysis, and pipeline/revenue measurement in long, multi-stage enterprise sales cycles
Hands-on martech stack experience—marketing automation (Marketo, HubSpot, or similar), Salesforce, lead routing, and third-party enrichment tools
Strong SQL skills; fluency working with large datasets in modern data stacks (ClickHouse, Snowflake, BigQuery, or similar)
Proven ability to translate complex analyses into clear narratives for non-technical stakeholders, including C-suite executives
High attention to detail and a strong point of view on what \"good\" looks like—you've built this infrastructure before and know where the landmines are
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nThe role\n\nThis is a foundational role on Sierra's Operations team, sitting at the intersection of marketing and GTM. As Marketing Operations and Analytics Lead, you'll own two things: the measurement infrastructure that connects marketing programs to pipeline and revenue; and the operational processes that make the marketing engine run efficiently and at scale.\n\nWhat you'll do\n\n - Full-funnel attribution: Design and own Sierra's marketing attribution framework, connecting campaigns, events, content, and demand gen programs to pipeline generation and ultimately LTC conversions.\n\n - Pipeline analytics: Partner with Marketing and Sales to analyze pipegen by vertical, region, and segment. Track conversion rates at each stage and surface where marketing programs are—and aren't—generating high-quality opportunities.\n\n - Performance reporting: Build and maintain the marketing team's core performance dashboards—campaign ROI, event pipeline influence, channel mix, lead quality, and funnel velocity.\n\n - ICP & account intelligence: Develop data-driven ICP scoring and account prioritization models to focus marketing investment on segments with the highest win rates and ASPs. Integrate signals from first-party and third-party intent sources to keep targeting sharp.\n\n - Experiment design & optimization: Design rigorous A/B and multivariate tests across marketing channels. Establish the statistical standards the team uses to evaluate new programs; translate results into clear, actionable recommendations—not just p-values.\n\n - Lead management & routing: Define and maintain lead scoring models, MQL thresholds, and routing logic from first touch to Sales handoff. Partner with Sales to ensure lead quality, minimize friction, and continuously improve conversion from MQL to pipeline.\n\n - Campaign operations: Own the operational infrastructure behind campaign execution—email programs, landing page workflows, event lead capture, and list management. Build processes that let the demand gen and events teams move quickly without creating data debt.\n\n - Cross-functional partnership: Serve as the analytical and operational bridge between Marketing, GTM Ops, Finance, and Sales leadership—ensuring marketing metrics are aligned with company PG, POC, and ARR targets; contribute to quarterly business reviews (QBRs) and annual planning with marketing-specific performance analysis and forecasts\n\nWhat you'll bring\n\n - 12+ years spanning marketing analytics and marketing operations\n\n - Deep expertise in attribution modeling, multi-touch funnel analysis, and pipeline/revenue measurement in long, multi-stage enterprise sales cycles\n\n - Hands-on martech stack experience—marketing automation (Marketo, HubSpot, or similar), Salesforce, lead routing, and third-party enrichment tools\n\n - Strong SQL skills; fluency working with large datasets in modern data stacks (ClickHouse, Snowflake, BigQuery, or similar)\n\n - Proven ability to translate complex analyses into clear narratives for non-technical stakeholders, including C-suite executives\n\n - High attention to detail and a strong point of view on what \"good\" looks like—you've built this infrastructure before and know where the landmines are\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b37a6f9e-53c7-4c47-beb5-1ab4451f3001","title":"Software Engineer, Agent (Mandarin Speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-06-12T15:52:13.611+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b37a6f9e-53c7-4c47-beb5-1ab4451f3001","applyUrl":"https://jobs.ashbyhq.com/sierra/b37a6f9e-53c7-4c47-beb5-1ab4451f3001/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Proficiency in Mandarin is required to support interactions with Mandarin speaking clients.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n - Proficiency in Mandarin is required to support interactions with Mandarin speaking clients.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"afc1d541-7442-4bae-80f4-7ed8d444efe9","title":"People Partner, Sales","department":"Operations","team":"HR","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-06-25T21:40:41.257+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/afc1d541-7442-4bae-80f4-7ed8d444efe9","applyUrl":"https://jobs.ashbyhq.com/sierra/afc1d541-7442-4bae-80f4-7ed8d444efe9/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Employee Relations: Serve as a key resource for employees and managers, providing guidance on HR policies, addressing and resolving employee conflicts, and fostering a positive and productive work environment.
HR Administration: Manage HR systems, maintain accurate employee records, benefits enrollment, and generating HR reports.
Employee Onboarding: Ensure a seamless experience from candidate offer approval to new hire start date.
HR Policy Implementation: Develop and ensure the effective implementation of HR policies and procedures across Sierra, ensuring alignment with legal requirements and company values.
Employee Engagement: Design and implement employee engagement programs to enhance employee satisfaction and foster transparent and effective communication.
Organizational design: (structuring teams for efficiency and scalability, defining roles and responsibilities, aligning talent with business strategy), strategic thinking, coaching, business acumen
5+ years of experience in human resources or people operations, ideally in a fast-growing environment supporting Sales organizations.
Demonstrated expertise and understanding of HR best practices, employment laws, and regulation.
Excellent organizational skills, attention to detail, and ability to manage multiple priorities in a fast-paced environment.
Proactive, innovative mindset with a focus on continuous improvement and strategic impact.
Experience partnering with engineering, product, or other technical teams.
Hands-on experience implementing HR systems and processes in a scaling company.
Exposure to international HR compliance, including global employment laws and cross-border workforce considerations.
Understanding of international compensation structures and total rewards programs.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Employee Relations: Serve as a key resource for employees and managers, providing guidance on HR policies, addressing and resolving employee conflicts, and fostering a positive and productive work environment.\n\n - HR Administration: Manage HR systems, maintain accurate employee records, benefits enrollment, and generating HR reports.\n\n - Employee Onboarding: Ensure a seamless experience from candidate offer approval to new hire start date.\n\n - HR Policy Implementation: Develop and ensure the effective implementation of HR policies and procedures across Sierra, ensuring alignment with legal requirements and company values.\n\n - Employee Engagement: Design and implement employee engagement programs to enhance employee satisfaction and foster transparent and effective communication.\n\n - Organizational design: (structuring teams for efficiency and scalability, defining roles and responsibilities, aligning talent with business strategy), strategic thinking, coaching, business acumen\n\n\nWHAT YOU’LL BRING\n\n - 5+ years of experience in human resources or people operations, ideally in a fast-growing environment supporting Sales organizations.\n\n - Demonstrated expertise and understanding of HR best practices, employment laws, and regulation.\n\n - Excellent organizational skills, attention to detail, and ability to manage multiple priorities in a fast-paced environment.\n\n - Proactive, innovative mindset with a focus on continuous improvement and strategic impact.\n\n - Experience partnering with engineering, product, or other technical teams.\n\n\nEVEN BETTER…\n\n - Hands-on experience implementing HR systems and processes in a scaling company.\n\n - Exposure to international HR compliance, including global employment laws and cross-border workforce considerations.\n\n - Understanding of international compensation structures and total rewards programs.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f51d6c09-d767-4e86-bc62-216b2051e318","title":"Software Engineer, Agent (Brazilian Portuguese speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-06-22T21:57:03.449+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f51d6c09-d767-4e86-bc62-216b2051e318","applyUrl":"https://jobs.ashbyhq.com/sierra/f51d6c09-d767-4e86-bc62-216b2051e318/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Language fluency - professional fluency in both Brazilian Portuguese and English
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Language fluency - professional fluency in both Brazilian Portuguese and English\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3935e2a4-eb85-44dd-8e50-1443402bc2b4","title":"GTM Operations, Pricing","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-14T11:19:33.297+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3935e2a4-eb85-44dd-8e50-1443402bc2b4","applyUrl":"https://jobs.ashbyhq.com/sierra/3935e2a4-eb85-44dd-8e50-1443402bc2b4/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We're looking for a pricing strategist to join our GTM operations team. You'll work with our sales team to develop and deliver pricing proposals and ROI case studies for customers, and to help them execute deals. You'll also collaborate with product, marketing, and operations teams to define our overall pricing and packaging strategy.
4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.
Experience negotiating complex customer partnerships
Familiarity with navigating sales cycles
Strong understanding of developing GTM operations using data-driven decision-making
Degree in Business Administration, Finance, or related field, or equivalent professional experience
Experience in partnerships, business development, and value engineering roles
Familiarity with AI or conversational AI technologies
Previous 0-1 startup or fast-paced high-growth environment experience
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nWe're looking for a pricing strategist to join our GTM operations team. You'll work with our sales team to develop and deliver pricing proposals and ROI case studies for customers, and to help them execute deals. You'll also collaborate with product, marketing, and operations teams to define our overall pricing and packaging strategy.\n\n\nWHAT YOU’LL BRING\n\n - 4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred.\n\n - Experience negotiating complex customer partnerships\n\n - Familiarity with navigating sales cycles\n\n - Strong understanding of developing GTM operations using data-driven decision-making\n\n - Degree in Business Administration, Finance, or related field, or equivalent professional experience\n\n\nEVEN BETTER…\n\n - Experience in partnerships, business development, and value engineering roles\n\n - Familiarity with AI or conversational AI technologies\n\n - Previous 0-1 startup or fast-paced high-growth environment experience\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b61f6eb8-2485-4ba8-b569-fa26eba5a6e8","title":"Commercial Counsel","department":"Legal","team":"Legal","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[],"publishedAt":"2026-07-02T00:49:40.585+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b61f6eb8-2485-4ba8-b569-fa26eba5a6e8","applyUrl":"https://jobs.ashbyhq.com/sierra/b61f6eb8-2485-4ba8-b569-fa26eba5a6e8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We’re hiring a Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact.
Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus.
Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability.
Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so.
Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed.
Judgement: Understand risk in the context of a hyperscaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement calls, and you will be empowered to do so.
Approach: A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others.
Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives.
2-6 years of legal experience, with a combination of both large law firm and in-house experience at a tech company.
A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software.
Strong communication skills (verbal and written) and the ability to partner with both legal and non-legal stakeholders.
A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment.
Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions.
A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues.
Law firm experience at a top-tier, internationally recognized law firm.
Experience working at a high-growth startup and operating with a sense of ownership.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nWe’re hiring a Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact.\n\n - Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus.\n\n - Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability.\n\n - Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so.\n\n - Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed.\n\n - Judgement: Understand risk in the context of a hyperscaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement calls, and you will be empowered to do so.\n\n - Approach: A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others.\n\n - Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives.\n\n\nWHAT YOU’LL BRING\n\n - 2-6 years of legal experience, with a combination of both large law firm and in-house experience at a tech company.\n\n - A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software.\n\n - Strong communication skills (verbal and written) and the ability to partner with both legal and non-legal stakeholders.\n\n - A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment.\n\n\nEVEN BETTER…\n\n - Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions.\n\n - A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues.\n\n - Law firm experience at a top-tier, internationally recognized law firm.\n\n - Experience working at a high-growth startup and operating with a sense of ownership.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b5ade182-e434-4f3d-9ce2-d14359036864","title":"Enterprise Sales Director - Majors, Healthcare","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-10T22:28:30.422+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b5ade182-e434-4f3d-9ce2-d14359036864","applyUrl":"https://jobs.ashbyhq.com/sierra/b5ade182-e434-4f3d-9ce2-d14359036864/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"63d41476-9621-4566-a6fa-8fde0d643836","title":"Enterprise Sales Director - Majors, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-10T22:39:00.975+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/63d41476-9621-4566-a6fa-8fde0d643836","applyUrl":"https://jobs.ashbyhq.com/sierra/63d41476-9621-4566-a6fa-8fde0d643836/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7ffb9df7-d413-45b1-91a4-27702f26ef6d","title":"Enterprise Sales Leader, Healthcare","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-10T22:41:04.249+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7ffb9df7-d413-45b1-91a4-27702f26ef6d","applyUrl":"https://jobs.ashbyhq.com/sierra/7ffb9df7-d413-45b1-91a4-27702f26ef6d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"675b6dab-6f04-4d9e-a6bd-c001f2784c0b","title":"Enterprise Sales Leader, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-07-10T22:42:48.722+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/675b6dab-6f04-4d9e-a6bd-c001f2784c0b","applyUrl":"https://jobs.ashbyhq.com/sierra/675b6dab-6f04-4d9e-a6bd-c001f2784c0b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1781b6b1-0f80-4163-bff1-321317554c22","title":"Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"Sydney","secondaryLocations":[],"publishedAt":"2026-07-30T23:13:00.070+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Australia","addressLocality":"Sydney"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1781b6b1-0f80-4163-bff1-321317554c22","applyUrl":"https://jobs.ashbyhq.com/sierra/1781b6b1-0f80-4163-bff1-321317554c22/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the full-cycle, end-to-end recruiting process, creating a positive candidate, interviewer, and Hiring Manager experience
Be a strategic partner, working closely with Hiring Managers to develop position profiles, understand overall needs and requirements, as well as the candidate market
Create and execute sourcing strategies across multiple channels for both active and passive candidates for each role
Track and analyze recruiting metrics and report to Hiring Managers and Sierra leadership on a regular cadence
5-8+ years of full-cycle recruiting experience at a high-growth tech company, with early-stage start-up experience preferred
Demonstrated expertise in recruiting, outbound sourcing, and closing candidates across technical and business roles
Ability to build impactful relationships with hiring managers and interview teams
Experience with Ashby ATS
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the full-cycle, end-to-end recruiting process, creating a positive candidate, interviewer, and Hiring Manager experience\n\n - Be a strategic partner, working closely with Hiring Managers to develop position profiles, understand overall needs and requirements, as well as the candidate market\n\n - Create and execute sourcing strategies across multiple channels for both active and passive candidates for each role\n\n - Track and analyze recruiting metrics and report to Hiring Managers and Sierra leadership on a regular cadence\n\n\nWHAT YOU'LL BRING\n\n - 5-8+ years of full-cycle recruiting experience at a high-growth tech company, with early-stage start-up experience preferred\n\n - Demonstrated expertise in recruiting, outbound sourcing, and closing candidates across technical and business roles\n\n - Ability to build impactful relationships with hiring managers and interview teams\n\n\nEVEN BETTER...\n\n - Experience with Ashby ATS\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"282771b4-9d75-4098-a660-beb4337a617c","title":"Enterprise Sales Director - Majors, Healthcare","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-07-16T00:18:25.974+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/282771b4-9d75-4098-a660-beb4337a617c","applyUrl":"https://jobs.ashbyhq.com/sierra/282771b4-9d75-4098-a660-beb4337a617c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n\n - 8- 10 YEARS OF ENTERPRISE CUSTOMER-FACING SALES EXPERIENCE, IDENTIFYING AND CLOSING LARGE ACCOUNTS.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"82d714bd-4908-4648-b72e-3322ad4211b6","title":"Enterprise Sales Director - Majors, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-07-16T00:18:48.293+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/82d714bd-4908-4648-b72e-3322ad4211b6","applyUrl":"https://jobs.ashbyhq.com/sierra/82d714bd-4908-4648-b72e-3322ad4211b6/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.
Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.
Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.
Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.
Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.
Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Proven ability to multi-thread and build trusted relationships across customer C-suites.
Exceptional verbal and written communication.
Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.
Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close.\n\n - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders.\n\n - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts.\n\n - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem.\n\n - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal.\n\n - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Proven ability to multi-thread and build trusted relationships across customer C-suites.\n\n - Exceptional verbal and written communication.\n\n - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9b94e279-5869-4a33-b50f-9aa01ff61a22","title":"Product Manager, Agent Development (Spanish speaking)","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-07-23T18:26:56.398+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9b94e279-5869-4a33-b50f-9aa01ff61a22","applyUrl":"https://jobs.ashbyhq.com/sierra/9b94e279-5869-4a33-b50f-9aa01ff61a22/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.
Engage with customers: In the role, you will engage with all levels of our customers’ businesses:
Discover and assess their requirements.
Prepare and present demonstrations of Sierra’s agent.
Address and overcome technical challenges in the business process by working with technical counterparts.
Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.
Become trusted advisors and drive strategic technical strategies for our customers.
Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.
3-5+ years experience in product development of highly technical products.
Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.
Experience crafting and tailoring a message for potential customers, including executives.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.
Professional fluency in both Spanish and English.
Degree in a technical or related field, or equivalent professional experience.
AI-related experience (experience with product development for AI agents a plus).
Some coding experience with React, Typescript, and Go.
MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).
Past roles that interface with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day.\n\n - Engage with customers: In the role, you will engage with all levels of our customers’ businesses:\n \n - Discover and assess their requirements.\n \n - Prepare and present demonstrations of Sierra’s agent.\n \n - Address and overcome technical challenges in the business process by working with technical counterparts.\n \n - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes.\n \n - Become trusted advisors and drive strategic technical strategies for our customers.\n\n - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers.\n\n\nWHAT YOU'LL BRING\n\n - 3-5+ years experience in product development of highly technical products.\n\n - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager.\n\n - Experience crafting and tailoring a message for potential customers, including executives.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments.\n\n - Professional fluency in both Spanish and English.\n\n - Degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - AI-related experience (experience with product development for AI agents a plus).\n\n - Some coding experience with React, Typescript, and Go.\n\n - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles).\n\n - Past roles that interface with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"6c246883-6335-413e-9183-ece94780590c","title":"Agent Development, Operations","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-07-30T07:55:45.547+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/6c246883-6335-413e-9183-ece94780590c","applyUrl":"https://jobs.ashbyhq.com/sierra/6c246883-6335-413e-9183-ece94780590c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Serve as the Strategy and Operations partner to support the part of our business focused on world class Agent Development for and with our Customers across the APAC region
Assist our Agent Development team with the planning, organisation and trade offs required to optimise the weekly deployment of multi disciplinary resources across different customers, agent builds and countries, including the timely and accurate maintenance of key systems that provide transparency and help the business make better decisions
Help define and scale the playbook for how Sierra designs, builds, evaluates, launches AI agents at large enterprises, including some of the less obvious areas needed to attend to the needs of these customers in each stage of this process
Work closely with Agent Strategist account leads to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.
Turn insight into action: Analyze complex datasets and translate findings across all aspects of the Agent Development organisation into clear, executive-ready recommendations that drive high leverage decisions and operationalize best practices
Coordinate cross-functional initiatives that span Strategy, Product, Eng, Legal and Ops teams including partnerships relevant to Agent Development - driving alignment, timelines, and accountability
Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create other operational leverage across Agent Development.
5+ years of experience in management consulting, or strategy and operations at top-tier technology companies.
Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.
Demonstrated experience supporting multi-disciplinary operational teams as a trusted strategy and operations adviser.
High standard of written work and the development and delivery of succinct executive communications - a master at making the complex simple.
Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.
Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.
Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.
A growth mindset and willingness to roll up your sleeves. No task is too small if it helps the team win.
Proficiency finding and using the best AI tools available to deliver your work faster and smarter allowing you to provide leveraged impact.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO:\n\n - Serve as the Strategy and Operations partner to support the part of our business focused on world class Agent Development for and with our Customers across the APAC region\n\n - Assist our Agent Development team with the planning, organisation and trade offs required to optimise the weekly deployment of multi disciplinary resources across different customers, agent builds and countries, including the timely and accurate maintenance of key systems that provide transparency and help the business make better decisions\n\n - Help define and scale the playbook for how Sierra designs, builds, evaluates, launches AI agents at large enterprises, including some of the less obvious areas needed to attend to the needs of these customers in each stage of this process\n\n - Work closely with Agent Strategist account leads to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.\n\n - Turn insight into action: Analyze complex datasets and translate findings across all aspects of the Agent Development organisation into clear, executive-ready recommendations that drive high leverage decisions and operationalize best practices\n\n - Coordinate cross-functional initiatives that span Strategy, Product, Eng, Legal and Ops teams including partnerships relevant to Agent Development - driving alignment, timelines, and accountability\n\n - Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create other operational leverage across Agent Development.\n\n\nWHAT YOU'LL BRING:\n\n - 5+ years of experience in management consulting, or strategy and operations at top-tier technology companies.\n\n - Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.\n\n - Demonstrated experience supporting multi-disciplinary operational teams as a trusted strategy and operations adviser.\n\n - High standard of written work and the development and delivery of succinct executive communications - a master at making the complex simple.\n\n - Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.\n\n - Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.\n\n - Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.\n\n - A growth mindset and willingness to roll up your sleeves. No task is too small if it helps the team win.\n\n - Proficiency finding and using the best AI tools available to deliver your work faster and smarter allowing you to provide leveraged impact.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"bae30d56-4257-430e-b1d7-590c8555995d","title":"Enterprise Sales Director (Brazilian Portuguese speaking)","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-04T02:52:33.206+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/bae30d56-4257-430e-b1d7-590c8555995d","applyUrl":"https://jobs.ashbyhq.com/sierra/bae30d56-4257-430e-b1d7-590c8555995d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
We are open to hiring for this role in New York City, NY; Atlanta, Georgia, Remote — Floria, or Remote - Texas.
Language fluency: professional fluency in both Brazilian Portuguese and English
8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - We are open to hiring for this role in New York City, NY; Atlanta, Georgia, Remote — Floria, or Remote - Texas.\n\n\nWHAT YOU'LL BRING\n\n - Language fluency: professional fluency in both Brazilian Portuguese and English\n\n - 8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"47fd7def-71fa-4585-a625-14e2f25f5058","title":"Security Technical Program Manager","department":"Security Programs & GRC","team":"Security Programs & GRC","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-05T00:01:19.867+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/47fd7def-71fa-4585-a625-14e2f25f5058","applyUrl":"https://jobs.ashbyhq.com/sierra/47fd7def-71fa-4585-a625-14e2f25f5058/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Drive high-impact security and infrastructure initiatives end-to-end. Lead complex, cross-functional programs spanning cloud infrastructure, platform security, identity and access management, detection and response, vulnerability management, and secure software delivery from problem definition through execution and sustained outcomes.
Own execution, planning, and program health. Be accountable for sequencing work, managing dependencies, tracking risk, and ensuring delivery of Sierra’s most critical security programs, with clear milestones and outcomes.
Help shape Sierra’s security strategy. Partner with security and engineering leadership to define priorities, investment areas, and execution plans that align risk reduction with platform growth, customer trust, and long-term scalability.
Build and strengthen security foundations. Drive programs that establish durable security primitives such as identity boundaries, access controls, logging and detection baselines, incident readiness, and secure defaults that future teams and features can confidently build on.
Translate ambiguity into clear execution. Decompose loosely defined security, risk, and compliance challenges particularly in emerging AI domains into structured programs, prioritized workstreams, and measurable outcomes.
Lead communication and alignment. Provide clear updates to leadership on program health, risks, dependencies, and tradeoffs; surface issues early and drive cross-functional alignment.
Engineering: Infrastructure, Data Platform and Agent SDK engineers to shape technical requirements, manage dependencies, and deliver resilient systems.
Security & GRC: Security engineering, risk, compliance, and privacy partners to align on threat models, control strategy, audits, and risk management in a rapidly evolving AI landscape.
Product and GTM: Product, Agent Development, and Sales to operationalize security commitments and respond to sophisticated customer and regulator expectations.
Legal: On security terms, third-party risk, and contractual obligations.
Executive Leadership: Senior leaders who rely on you for clarity, prioritization, and confidence in Sierra’s security strategy and execution.
Experience running security-focused technical programs in fast-growing SaaS or platform environments.
Strong technical fluency across cloud infrastructure, IAM, infrastructure as code, observability, secure CI/CD, and incident response.
Ability to execute through ambiguity, prioritize effectively, and keep teams moving.
Comfort operating in environments where things aren’t fully built yet and helping decide what needs to be built first.
Clear, concise communication with senior technical and business leaders.
A collaborative, pragmatic style with high ownership and high agency.
Experience scaling security programs globally in AI-first or data-intensive SaaS environments.
Exposure to emerging AI risk, data governance, or agent and model-related security considerations.
Experience supporting security initiatives in public-sector, regulated and/or multi-cloud environments (AWS, GCP, Azure).
Relevant security, cloud, AI or technical program management certifications.
Familiarity with regulatory and compliance frameworks (ISO 27001, PCI DSS, FedRAMP, HIPAA)
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Drive high-impact security and infrastructure initiatives end-to-end. Lead complex, cross-functional programs spanning cloud infrastructure, platform security, identity and access management, detection and response, vulnerability management, and secure software delivery from problem definition through execution and sustained outcomes.\n\n - Own execution, planning, and program health. Be accountable for sequencing work, managing dependencies, tracking risk, and ensuring delivery of Sierra’s most critical security programs, with clear milestones and outcomes.\n\n - Help shape Sierra’s security strategy. Partner with security and engineering leadership to define priorities, investment areas, and execution plans that align risk reduction with platform growth, customer trust, and long-term scalability.\n\n - Build and strengthen security foundations. Drive programs that establish durable security primitives such as identity boundaries, access controls, logging and detection baselines, incident readiness, and secure defaults that future teams and features can confidently build on.\n\n - Translate ambiguity into clear execution. Decompose loosely defined security, risk, and compliance challenges particularly in emerging AI domains into structured programs, prioritized workstreams, and measurable outcomes.\n\n - Lead communication and alignment. Provide clear updates to leadership on program health, risks, dependencies, and tradeoffs; surface issues early and drive cross-functional alignment.\n\n\nWHO YOU'LL WORK WITH\n\n - Engineering: Infrastructure, Data Platform and Agent SDK engineers to shape technical requirements, manage dependencies, and deliver resilient systems.\n\n - Security & GRC: Security engineering, risk, compliance, and privacy partners to align on threat models, control strategy, audits, and risk management in a rapidly evolving AI landscape.\n\n - Product and GTM: Product, Agent Development, and Sales to operationalize security commitments and respond to sophisticated customer and regulator expectations.\n\n - Legal: On security terms, third-party risk, and contractual obligations.\n\n - Executive Leadership: Senior leaders who rely on you for clarity, prioritization, and confidence in Sierra’s security strategy and execution.\n\n\nWHAT YOU'LL BRING\n\n - Experience running security-focused technical programs in fast-growing SaaS or platform environments.\n\n - Strong technical fluency across cloud infrastructure, IAM, infrastructure as code, observability, secure CI/CD, and incident response.\n\n - Ability to execute through ambiguity, prioritize effectively, and keep teams moving.\n\n - Comfort operating in environments where things aren’t fully built yet and helping decide what needs to be built first.\n\n - Clear, concise communication with senior technical and business leaders.\n\n - A collaborative, pragmatic style with high ownership and high agency.\n\n\nEVEN BETTER...\n\n - Experience scaling security programs globally in AI-first or data-intensive SaaS environments.\n\n - Exposure to emerging AI risk, data governance, or agent and model-related security considerations.\n\n - Experience supporting security initiatives in public-sector, regulated and/or multi-cloud environments (AWS, GCP, Azure).\n\n - Relevant security, cloud, AI or technical program management certifications.\n\n - Familiarity with regulatory and compliance frameworks (ISO 27001, PCI DSS, FedRAMP, HIPAA)\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"177590bb-3851-4c40-a5c3-fffdf999d3b5","title":"Enterprise Sales Director, Financial Services","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-08-05T04:12:21.367+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/177590bb-3851-4c40-a5c3-fffdf999d3b5","applyUrl":"https://jobs.ashbyhq.com/sierra/177590bb-3851-4c40-a5c3-fffdf999d3b5/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7ec62895-e3b6-4a01-8d4b-df3909cbbbb8","title":"Enterprise Sales Director - Strategic, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-08-05T04:11:51.713+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7ec62895-e3b6-4a01-8d4b-df3909cbbbb8","applyUrl":"https://jobs.ashbyhq.com/sierra/7ec62895-e3b6-4a01-8d4b-df3909cbbbb8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
Mastery of complex deal structuring, risk navigation, and pricing.
Exceptional executive communication and a reputation for precision and trust.
Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.
Experience operating alongside founders/executives in front of strategic customers.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.\n\n - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.\n\n - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.\n\n - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.\n\n - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.\n\n - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.\n\n - Mastery of complex deal structuring, risk navigation, and pricing.\n\n - Exceptional executive communication and a reputation for precision and trust.\n\n\nEVEN BETTER...\n\n - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.\n\n - Experience operating alongside founders/executives in front of strategic customers.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"e17cc0d2-9eee-476f-8fe2-b7b7ba8faa85","title":"Enterprise Sales Director - Strategic, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:11:49.353+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/e17cc0d2-9eee-476f-8fe2-b7b7ba8faa85","applyUrl":"https://jobs.ashbyhq.com/sierra/e17cc0d2-9eee-476f-8fe2-b7b7ba8faa85/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
Mastery of complex deal structuring, risk navigation, and pricing.
Exceptional executive communication and a reputation for precision and trust.
Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.
Experience operating alongside founders/executives in front of strategic customers.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.\n\n - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.\n\n - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.\n\n - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.\n\n - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.\n\n - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.\n\n - Mastery of complex deal structuring, risk navigation, and pricing.\n\n - Exceptional executive communication and a reputation for precision and trust.\n\n\nEVEN BETTER...\n\n - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.\n\n - Experience operating alongside founders/executives in front of strategic customers.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b5250817-ec41-449a-aeee-c4d7a68850d9","title":"Ecosystem Operations ","department":"Partnerships","team":"Partnerships","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}}],"publishedAt":"2026-09-17T19:28:59.636+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b5250817-ec41-449a-aeee-c4d7a68850d9","applyUrl":"https://jobs.ashbyhq.com/sierra/b5250817-ec41-449a-aeee-c4d7a68850d9/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Help build the operational foundation that powers Sierra's ecosystem—and the global community building the future of AI agents.
Sierra's ecosystem is growing rapidly. Customers, partners, and developers around the world are building on Sierra to create the next generation of AI-powered experiences. As that community grows, we're looking for an Ecosystem Operations Manager to help scale the programs, systems, and operations that enable it to thrive.
This is a high-impact, cross-functional role within Sierra's Partnerships & Ecosystems team. You'll help operate and improve Sierra University, partner enablement, developer relations, and builder community programs while strengthening the operational foundation that enables the ecosystem to scale.
Working closely with Product, Engineering, Marketing, GTM, Agent Development, and Partnerships, you'll improve processes, coordinate programs, and build the operational rigor that allows our ecosystem to grow efficiently.
We're looking for someone who enjoys bringing order to complexity—someone who can build scalable processes, execute high-impact programs, and continuously improve how we serve customers, partners, and builders.
Scale Sierra University by managing curriculum operations, certification programs, learner journeys, platform administration, and governance.
Coordinate programs that grow Sierra's global builder community, creating opportunities for customers and partners to learn, connect, and succeed.
Drive partner enablement operations in partnership with the Partnerships team, ensuring partners have the training, resources, and operational support they need to activate quickly.
Create and maintain developer-facing resources—including documentation, tutorials, videos, and technical enablement materials—that help builders get the most from Sierra's platform.
Plan and execute ecosystem events, including certification launches, builder summits, partner workshops, developer days, and community activations.
Build and improve the operational systems, reporting, and processes that enable the Partnerships & Ecosystems team to scale efficiently.
Partner across Product, Engineering, Marketing, GTM, Agent Development, and Partnerships to coordinate ecosystem initiatives and keep programs moving.
Measure ecosystem health through certification adoption, partner activation, community engagement, content effectiveness, and customer feedback, and use those insights to continuously improve how Sierra serves builders and partners.
6–8+ years of experience in ecosystem operations, developer relations, community programs, partner enablement, program management, or a related function at an enterprise SaaS or developer platform company.
Experience operating and scaling customer, partner, or developer programs.
Experience creating developer-facing content, including documentation, tutorials, videos, or technical enablement materials.
Fluent in modern AI tools and workflows, with hands-on experience leveraging AI to improve productivity and a strong understanding of how AI agents, LLMs, and developer tools are transforming the way software is built, shipped, and adopted.
Excellent written and verbal communication skills, with experience producing both customer-facing content and executive-ready communications.
Highly organized, execution-oriented, and energized by building scalable programs in fast-moving environments.
Willingness to travel as needed to support Sierra University, partner enablement, ecosystem events, builder programs, and community engagement.
Experience at companies with scaled developer ecosystems, learning platforms, or partner communities.
Experience supporting both customer and partner audiences.
Familiarity with learning management systems, community platforms, event operations, and modern content creation tools.
Experience working with AI platforms, developer tools, or enterprise software ecosystems.
Prior software development, solutions engineering, or technical implementation experience.
Experience scaling global ecosystem programs in fast-growing environments with limited existing processes or playbooks.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nHelp build the operational foundation that powers Sierra's ecosystem—and the global community building the future of AI agents.\n\nSierra's ecosystem is growing rapidly. Customers, partners, and developers around the world are building on Sierra to create the next generation of AI-powered experiences. As that community grows, we're looking for an Ecosystem Operations Manager to help scale the programs, systems, and operations that enable it to thrive.\n\nThis is a high-impact, cross-functional role within Sierra's Partnerships & Ecosystems team. You'll help operate and improve Sierra University, partner enablement, developer relations, and builder community programs while strengthening the operational foundation that enables the ecosystem to scale.\n\nWorking closely with Product, Engineering, Marketing, GTM, Agent Development, and Partnerships, you'll improve processes, coordinate programs, and build the operational rigor that allows our ecosystem to grow efficiently.\n\nWe're looking for someone who enjoys bringing order to complexity—someone who can build scalable processes, execute high-impact programs, and continuously improve how we serve customers, partners, and builders.\n\n\n\n\nWHAT YOU'LL DO\n\n - Scale Sierra University by managing curriculum operations, certification programs, learner journeys, platform administration, and governance.\n\n - Coordinate programs that grow Sierra's global builder community, creating opportunities for customers and partners to learn, connect, and succeed.\n\n - Drive partner enablement operations in partnership with the Partnerships team, ensuring partners have the training, resources, and operational support they need to activate quickly.\n\n - Create and maintain developer-facing resources—including documentation, tutorials, videos, and technical enablement materials—that help builders get the most from Sierra's platform.\n\n - Plan and execute ecosystem events, including certification launches, builder summits, partner workshops, developer days, and community activations.\n\n - Build and improve the operational systems, reporting, and processes that enable the Partnerships & Ecosystems team to scale efficiently.\n\n - Partner across Product, Engineering, Marketing, GTM, Agent Development, and Partnerships to coordinate ecosystem initiatives and keep programs moving.\n\n - Measure ecosystem health through certification adoption, partner activation, community engagement, content effectiveness, and customer feedback, and use those insights to continuously improve how Sierra serves builders and partners.\n\n\nWHAT YOU'LL BRING\n\n - 6–8+ years of experience in ecosystem operations, developer relations, community programs, partner enablement, program management, or a related function at an enterprise SaaS or developer platform company.\n\n - Experience operating and scaling customer, partner, or developer programs.\n\n - Experience creating developer-facing content, including documentation, tutorials, videos, or technical enablement materials.\n\n - Fluent in modern AI tools and workflows, with hands-on experience leveraging AI to improve productivity and a strong understanding of how AI agents, LLMs, and developer tools are transforming the way software is built, shipped, and adopted.\n\n - Excellent written and verbal communication skills, with experience producing both customer-facing content and executive-ready communications.\n\n - Highly organized, execution-oriented, and energized by building scalable programs in fast-moving environments.\n\n - Willingness to travel as needed to support Sierra University, partner enablement, ecosystem events, builder programs, and community engagement.\n\n\nEVEN BETTER...\n\n - Experience at companies with scaled developer ecosystems, learning platforms, or partner communities.\n\n - Experience supporting both customer and partner audiences.\n\n - Familiarity with learning management systems, community platforms, event operations, and modern content creation tools.\n\n - Experience working with AI platforms, developer tools, or enterprise software ecosystems.\n\n - Prior software development, solutions engineering, or technical implementation experience.\n\n - Experience scaling global ecosystem programs in fast-growing environments with limited existing processes or playbooks.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"a79b2ff9-fa5e-4ab5-ac08-91916998bf91","title":"Enterprise Sales Director - Strategic","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[{"location":"Toronto","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-08-05T04:11:21.800+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/a79b2ff9-fa5e-4ab5-ac08-91916998bf91","applyUrl":"https://jobs.ashbyhq.com/sierra/a79b2ff9-fa5e-4ab5-ac08-91916998bf91/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
Mastery of complex deal structuring, risk navigation, and pricing.
Exceptional executive communication and a reputation for precision and trust.
Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.
Experience operating alongside founders/executives in front of strategic customers.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.\n\n - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.\n\n - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.\n\n - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.\n\n - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.\n\n - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.\n\n - Mastery of complex deal structuring, risk navigation, and pricing.\n\n - Exceptional executive communication and a reputation for precision and trust.\n\n\nEVEN BETTER...\n\n - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.\n\n - Experience operating alongside founders/executives in front of strategic customers.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3ad32de4-8fe4-4a68-8be9-30a28a320046","title":"Enterprise Sales Director - Strategic","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:11:19.387+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3ad32de4-8fe4-4a68-8be9-30a28a320046","applyUrl":"https://jobs.ashbyhq.com/sierra/3ad32de4-8fe4-4a68-8be9-30a28a320046/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.
Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.
Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.
Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.
Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.
Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.
Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.
Mastery of complex deal structuring, risk navigation, and pricing.
Exceptional executive communication and a reputation for precision and trust.
Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.
Experience operating alongside founders/executives in front of strategic customers.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Architect Sierra's most complex deals: Lead our largest multi-BU, multi-geo opportunities, designing sophisticated deal structures and managing risk with precision and conviction.\n\n - Operate as part of the customer's team: Hold trusted relationships across the customer C-suite and working teams.\n\n - Engage at the founder level: Be trusted to regularly engage and manage Sierra's co-founders in front of customers, pitching with co-founder-like conviction and expertise.\n\n - Bring precision to everything: Operate with exacting craft in messaging, positioning, and timing across every interaction.\n\n - Shape strategy: Influence how Sierra approaches its most important accounts and set the standard for the broader sales org.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 10-12+ years of enterprise/strategic sales experience, owning the largest and most complex accounts.\n\n - Demonstrated success closing multi-million-dollar, multi-stakeholder deals spanning business units and geographies.\n\n - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Deep, sustained C-suite relationships and the gravitas to be treated as a peer by executive buyers.\n\n - Mastery of complex deal structuring, risk navigation, and pricing.\n\n - Exceptional executive communication and a reputation for precision and trust.\n\n\nEVEN BETTER...\n\n - Deep familiarity with the AI landscape and the ability to speak credibly to technical and business stakeholders alike.\n\n - Experience operating alongside founders/executives in front of strategic customers.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1e89171e-b7c4-4eca-a624-db96771505ce","title":"Enterprise Sales Director, Healthcare","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-08-05T04:13:15.340+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1e89171e-b7c4-4eca-a624-db96771505ce","applyUrl":"https://jobs.ashbyhq.com/sierra/1e89171e-b7c4-4eca-a624-db96771505ce/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7103380f-de16-4d28-968d-38fb5f0c9ce6","title":"Enterprise Sales Director, Healthcare","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:13:13.288+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7103380f-de16-4d28-968d-38fb5f0c9ce6","applyUrl":"https://jobs.ashbyhq.com/sierra/7103380f-de16-4d28-968d-38fb5f0c9ce6/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"99858356-70b7-4c3a-aefb-87415e3fdbad","title":"Enterprise Sales Director, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Canada - Remote","secondaryLocations":[],"publishedAt":"2026-08-05T04:13:26.814+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"Canada"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/99858356-70b7-4c3a-aefb-87415e3fdbad","applyUrl":"https://jobs.ashbyhq.com/sierra/99858356-70b7-4c3a-aefb-87415e3fdbad/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ae852ea8-a4fb-40b2-a390-e06f34622d9e","title":"Enterprise Sales Director, Retail","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T04:13:24.623+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ae852ea8-a4fb-40b2-a390-e06f34622d9e","applyUrl":"https://jobs.ashbyhq.com/sierra/ae852ea8-a4fb-40b2-a390-e06f34622d9e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.
6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.\n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow.\n\n\nWHAT YOU'LL BRING\n\n - 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals.\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"84c568d0-28ba-4a7d-829a-fa21b1ab2aaf","title":"Enterprise Sales Leader, Consumer Business Services","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-21T19:38:34.004+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/84c568d0-28ba-4a7d-829a-fa21b1ab2aaf","applyUrl":"https://jobs.ashbyhq.com/sierra/84c568d0-28ba-4a7d-829a-fa21b1ab2aaf/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.
This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.
Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE CONSUMER BUSINESS SERVICES TEAM\n\n - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.\n\n - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.\n\n - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"17bd055c-c281-4c01-bf61-671710b25cc0","title":"Enterprise Sales Engineer, Retail","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T21:26:31.300+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/17bd055c-c281-4c01-bf61-671710b25cc0","applyUrl":"https://jobs.ashbyhq.com/sierra/17bd055c-c281-4c01-bf61-671710b25cc0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ab7ce8a1-d088-4808-93e2-a4162c315821","title":"Enterprise Sales Engineer, Healthcare","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-05T21:26:34.070+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ab7ce8a1-d088-4808-93e2-a4162c315821","applyUrl":"https://jobs.ashbyhq.com/sierra/ab7ce8a1-d088-4808-93e2-a4162c315821/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"cbf21891-c044-427f-80a4-e03474df702e","title":"Enterprise Sales Engineer","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"South Korea","secondaryLocations":[],"publishedAt":"2026-08-25T13:35:19.609+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"South Korea"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/cbf21891-c044-427f-80a4-e03474df702e","applyUrl":"https://jobs.ashbyhq.com/sierra/cbf21891-c044-427f-80a4-e03474df702e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Strong English and Korean written and verbal communication
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n - Strong English and Korean written and verbal communication\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3cdeb98c-a25c-4f3b-a704-1418556454bc","title":"Software Engineer, Agent","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"South Korea","secondaryLocations":[],"publishedAt":"2026-08-25T14:18:00.377+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"South Korea"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3cdeb98c-a25c-4f3b-a704-1418556454bc","applyUrl":"https://jobs.ashbyhq.com/sierra/3cdeb98c-a25c-4f3b-a704-1418556454bc/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Strong English and Korean communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Strong English and Korean communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"575cf637-3a7a-4d9c-883c-8b0265811984","title":"Agent Strategist","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"South Korea","secondaryLocations":[],"publishedAt":"2026-08-25T14:16:56.252+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"South Korea"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/575cf637-3a7a-4d9c-883c-8b0265811984","applyUrl":"https://jobs.ashbyhq.com/sierra/575cf637-3a7a-4d9c-883c-8b0265811984/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Strong English and Korean communication skills. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Strong English and Korean communication skills. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"09d3d084-02f2-49a2-acb9-d1fe380b817c","title":"Operations Manager, Product & Engineering","department":"Operations","team":"Business Operations","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-08-10T13:49:03.588+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/09d3d084-02f2-49a2-acb9-d1fe380b817c","applyUrl":"https://jobs.ashbyhq.com/sierra/09d3d084-02f2-49a2-acb9-d1fe380b817c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Run the operating cadence for Product & Engineering: own planning cycles, roadmap workflows, initiative tracking, sprint planning, and team initiatives
Design and optimize key processes like product reviews, retrospectives, team syncs, and engineering demos to drive clarity and velocity
Build and maintain operational artifacts such as roadmaps, planning docs, capacity trackers, dashboards, and retros that keep everyone informed and aligned
Coordinate cross-functional initiatives that span Product, Eng, Design, Brand, Sales, and Ops teams—driving alignment, timelines, and accountability
Partner with product, eng and marketing leads to create scalable frameworks for goal-setting (e.g., OKRs), prioritization, and execution
Analyze operational data and team feedback to identify friction points and implement systems that improve execution and outcomes
Build our internationalization operations playbook and continuously improve it so we can scale with quality and intention
6-8+ years of experience in Product Operations, Business Operations, or Program Management in a high-growth, product-led company
Proven track record building and scaling operational processes from scratch
Highly organized and methodical; you bring rigor, structure, and momentum to ambiguous situations
Excellent written and verbal communicator—clear, succinct, and persuasive across stakeholders and levels
Comfortable using tools like Linear, Figma, Google Drive, or similar to create systems that stick
Strong analytical instincts with proficiency in Excel/Sheets; SQL or dashboard experience is a plus
Experience at an early-stage startup or scaling product org
Familiarity with OKR frameworks, roadmap tools, or product analytics platforms
Background in product management, engineering, or consulting/strategy with deep operational exposure
Experience with vendor management and localization expansion efforts
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Run the operating cadence for Product & Engineering: own planning cycles, roadmap workflows, initiative tracking, sprint planning, and team initiatives\n\n - Design and optimize key processes like product reviews, retrospectives, team syncs, and engineering demos to drive clarity and velocity\n\n - Build and maintain operational artifacts such as roadmaps, planning docs, capacity trackers, dashboards, and retros that keep everyone informed and aligned\n\n - Coordinate cross-functional initiatives that span Product, Eng, Design, Brand, Sales, and Ops teams—driving alignment, timelines, and accountability\n\n - Partner with product, eng and marketing leads to create scalable frameworks for goal-setting (e.g., OKRs), prioritization, and execution\n\n - Analyze operational data and team feedback to identify friction points and implement systems that improve execution and outcomes\n\n - Build our internationalization operations playbook and continuously improve it so we can scale with quality and intention\n\n\nWHAT YOU’LL BRING\n\n - 6-8+ years of experience in Product Operations, Business Operations, or Program Management in a high-growth, product-led company\n\n - Proven track record building and scaling operational processes from scratch\n\n - Highly organized and methodical; you bring rigor, structure, and momentum to ambiguous situations\n\n - Excellent written and verbal communicator—clear, succinct, and persuasive across stakeholders and levels\n\n - Comfortable using tools like Linear, Figma, Google Drive, or similar to create systems that stick\n\n - Strong analytical instincts with proficiency in Excel/Sheets; SQL or dashboard experience is a plus\n\n\nEVEN BETTER…\n\n - Experience at an early-stage startup or scaling product org\n\n - Familiarity with OKR frameworks, roadmap tools, or product analytics platforms\n\n - Background in product management, engineering, or consulting/strategy with deep operational exposure\n\n - Experience with vendor management and localization expansion efforts\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"cc6e10fd-9420-446c-915d-6edac6ca93ef","title":"Operations Manager, Product & Engineering","department":"Operations","team":"Business Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-10T13:54:19.158+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/cc6e10fd-9420-446c-915d-6edac6ca93ef","applyUrl":"https://jobs.ashbyhq.com/sierra/cc6e10fd-9420-446c-915d-6edac6ca93ef/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Run the operating cadence for Product & Engineering: own planning cycles, roadmap workflows, initiative tracking by region and channel, sequencing, and team initiatives
Design and optimize key processes like product reviews, retrospectives, team syncs, and engineering demos to drive clarity and velocity
Build and maintain operational artifacts such as roadmaps, planning docs, capacity trackers, dashboards, and retros that keep everyone informed and aligned
Coordinate cross-functional initiatives that span Product, Eng, Design, Legal, Sales, and Ops teams—driving alignment, timelines, and accountability
Partner with product, eng and marketing leads to create scalable frameworks for goal-setting (e.g., OKRs), prioritization, and execution
Analyze operational data and team feedback to identify friction points and implement systems that improve execution and outcomes
Build our outbound operations playbook in partnership with Legal and continuously improve it so we can scale with quality and intention
6-8+ years of experience in Product Operations, Business Operations, or Program Management in a high-growth, product-led company
Proven track record building and scaling operational processes from scratch
Highly organized and methodical; you bring rigor, structure, and momentum to ambiguous situations
Excellent written and verbal communicator—clear, succinct, and persuasive across stakeholders and levels
Experience partnering closely with Legal, Product, and Engineering, including third-party vendors
Comfortable using tools like Linear, Figma, Google Drive, or similar to create systems that stick
Strong analytical instincts with proficiency in Excel/Sheets; SQL or dashboard experience is a plus
Experience with outbound communications compliance — TCPA, do-not-call, SMS sender registration, or similar calling/messaging regulations in the US or internationally
Experience at an early-stage startup or scaling product org
Familiarity with OKR frameworks, roadmap tools, or product analytics platforms
Background in product management, engineering, or consulting/strategy with deep operational exposure
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Run the operating cadence for Product & Engineering: own planning cycles, roadmap workflows, initiative tracking by region and channel, sequencing, and team initiatives\n\n - Design and optimize key processes like product reviews, retrospectives, team syncs, and engineering demos to drive clarity and velocity\n\n - Build and maintain operational artifacts such as roadmaps, planning docs, capacity trackers, dashboards, and retros that keep everyone informed and aligned\n\n - Coordinate cross-functional initiatives that span Product, Eng, Design, Legal, Sales, and Ops teams—driving alignment, timelines, and accountability\n\n - Partner with product, eng and marketing leads to create scalable frameworks for goal-setting (e.g., OKRs), prioritization, and execution\n\n - Analyze operational data and team feedback to identify friction points and implement systems that improve execution and outcomes\n\n - Build our outbound operations playbook in partnership with Legal and continuously improve it so we can scale with quality and intention\n\n\nWHAT YOU’LL BRING\n\n - 6-8+ years of experience in Product Operations, Business Operations, or Program Management in a high-growth, product-led company\n\n - Proven track record building and scaling operational processes from scratch\n\n - Highly organized and methodical; you bring rigor, structure, and momentum to ambiguous situations\n\n - Excellent written and verbal communicator—clear, succinct, and persuasive across stakeholders and levels\n\n - Experience partnering closely with Legal, Product, and Engineering, including third-party vendors\n\n - Comfortable using tools like Linear, Figma, Google Drive, or similar to create systems that stick\n\n - Strong analytical instincts with proficiency in Excel/Sheets; SQL or dashboard experience is a plus\n\n\nEVEN BETTER…\n\n - Experience with outbound communications compliance — TCPA, do-not-call, SMS sender registration, or similar calling/messaging regulations in the US or internationally\n\n - Experience at an early-stage startup or scaling product org\n\n - Familiarity with OKR frameworks, roadmap tools, or product analytics platforms\n\n - Background in product management, engineering, or consulting/strategy with deep operational exposure\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"adaa6543-00df-4e5f-8e40-e4327ccb764c","title":"Enterprise Sales Engineer (Spanish speaking)","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-11T00:05:16.363+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/adaa6543-00df-4e5f-8e40-e4327ccb764c","applyUrl":"https://jobs.ashbyhq.com/sierra/adaa6543-00df-4e5f-8e40-e4327ccb764c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
Language fluency - professional fluency in both Spanish and English
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - Language fluency - professional fluency in both Spanish and English\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"102b597d-876d-458f-bf11-58924df4b73d","title":"Enterprise Sales Engineer (Brazilian Portuguese speaking)","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-11T00:05:12.283+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/102b597d-876d-458f-bf11-58924df4b73d","applyUrl":"https://jobs.ashbyhq.com/sierra/102b597d-876d-458f-bf11-58924df4b73d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
Language fluency - professional fluency in both Brazilian Portuguese and English
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - Language fluency - professional fluency in both Brazilian Portuguese and English\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"218bb363-73f9-4f4e-beac-d667a28b65ff","title":"Enterprise Sales Director - Majors, Public Sector","department":"Sales","team":"Sales","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}},{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-01T04:25:09.691+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/218bb363-73f9-4f4e-beac-d667a28b65ff","applyUrl":"https://jobs.ashbyhq.com/sierra/218bb363-73f9-4f4e-beac-d667a28b65ff/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Build Sierra’s public sector business: Own a portfolio of strategic Federal, state or local government accounts, develop territory and account plans, build qualified pipeline, and consistently achieve or exceed revenue targets.
Create opportunities around mission outcomes: Develop trusted relationships with agency leaders, program executives, technology teams, procurement officials, and other stakeholders. Translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities.
Lead complex sales cycles from discovery through award: Orchestrate executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close across long, multi-stakeholder government buying processes.
Design the path to contract: Understand how each customer can buy and shape a practical acquisition strategy early. Navigate direct awards, competitive solicitations, pilots, task orders, and contract vehicles—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements—as relevant to the opportunity.
Build and execute capture plans: Qualify opportunities with discipline; map decision-makers, influencers, incumbents, competitors, funding sources, fiscal-year timing, acquisition milestones, and win themes; and lead the internal cadence required to move from early demand to award.
Develop Sierra’s partner ecosystem: Build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and other technology providers. Know when Sierra should sell directly, participate as a subcontractor, establish a teaming arrangement, or pursue a partner-led transaction—and align incentives and responsibilities accordingly.
Shape prime and teaming relationships: Identify where Sierra can strengthen a prime contractor’s solution and where partners can provide customer access, past performance, implementation capacity, or a procurement pathway. Negotiate clear account alignment, deal registration, workshare, and go-to-market plans that create durable value for the customer and Sierra.
Run high-quality bids and proposals: Partner with public sector leadership, legal, security, product, engineering, and delivery teams on RFIs, RFPs, sources sought, oral presentations, and other procurement responses. Make thoughtful bid/no-bid recommendations and ensure every submission is compliant, differentiated, and precise.
Operate as part of the customer’s team: Earn trust across senior agency leadership and working teams by understanding the mission, communicating candidly, and remaining accountable from the first meeting through deployment and expansion.
Help build the public sector go-to-market motion: As an early member of the team, improve our account segmentation, capture process, partner strategy, contract-vehicle roadmap, forecasting, and repeatable sales playbooks. Bring market signals back to product and company leadership to help shape Sierra’s platform and public sector strategy.
Operate as an AI-native seller: Use AI throughout the sales cycle—from account research and personalized outreach to call synthesis, opportunity planning, proposal development, and forecasting—so you can spend more time on judgment, strategy, and customer relationships.
Meaningful enterprise technology sales or business development experience, including significant experience selling software, cloud, data, or AI solutions to U.S. government customers.
A demonstrated record of building pipeline, exceeding quota, and closing complex six- and seven-figure opportunities with long sales cycles and multiple technical, mission, executive, and procurement stakeholders.
Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles.
Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public.
A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners.
Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity.
The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward.
Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps.
A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve.
Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions.
Experience helping launch or scale a public sector business for a high-growth software company.
Established relationships across Federal civilian agencies, state governments, or the government contractor and systems integrator ecosystem.
Familiarity with the FAR and related acquisition frameworks, government cloud and security requirements, and the commercial implications of FedRAMP High.
Experience shaping and closing outcome-based, usage-based, or other nontraditional software agreements in the public sector.
Experience with AI, conversational systems, customer experience technology, contact centers, or digital government services—and the ability to speak credibly with both mission and technical leaders.
Experience operating alongside founders or senior executives in high-stakes customer and partner engagements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU'LL DO\n\n - Build Sierra’s public sector business: Own a portfolio of strategic Federal, state or local government accounts, develop territory and account plans, build qualified pipeline, and consistently achieve or exceed revenue targets.\n\n - Create opportunities around mission outcomes: Develop trusted relationships with agency leaders, program executives, technology teams, procurement officials, and other stakeholders. Translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities.\n\n - Lead complex sales cycles from discovery through award: Orchestrate executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close across long, multi-stakeholder government buying processes.\n\n - Design the path to contract: Understand how each customer can buy and shape a practical acquisition strategy early. Navigate direct awards, competitive solicitations, pilots, task orders, and contract vehicles—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements—as relevant to the opportunity.\n\n - Build and execute capture plans: Qualify opportunities with discipline; map decision-makers, influencers, incumbents, competitors, funding sources, fiscal-year timing, acquisition milestones, and win themes; and lead the internal cadence required to move from early demand to award.\n\n - Develop Sierra’s partner ecosystem: Build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and other technology providers. Know when Sierra should sell directly, participate as a subcontractor, establish a teaming arrangement, or pursue a partner-led transaction—and align incentives and responsibilities accordingly.\n\n - Shape prime and teaming relationships: Identify where Sierra can strengthen a prime contractor’s solution and where partners can provide customer access, past performance, implementation capacity, or a procurement pathway. Negotiate clear account alignment, deal registration, workshare, and go-to-market plans that create durable value for the customer and Sierra.\n\n - Run high-quality bids and proposals: Partner with public sector leadership, legal, security, product, engineering, and delivery teams on RFIs, RFPs, sources sought, oral presentations, and other procurement responses. Make thoughtful bid/no-bid recommendations and ensure every submission is compliant, differentiated, and precise.\n\n - Operate as part of the customer’s team: Earn trust across senior agency leadership and working teams by understanding the mission, communicating candidly, and remaining accountable from the first meeting through deployment and expansion.\n\n - Help build the public sector go-to-market motion: As an early member of the team, improve our account segmentation, capture process, partner strategy, contract-vehicle roadmap, forecasting, and repeatable sales playbooks. Bring market signals back to product and company leadership to help shape Sierra’s platform and public sector strategy.\n\n - Operate as an AI-native seller: Use AI throughout the sales cycle—from account research and personalized outreach to call synthesis, opportunity planning, proposal development, and forecasting—so you can spend more time on judgment, strategy, and customer relationships.\n\n\nWHAT YOU'LL BRING\n\n - Meaningful enterprise technology sales or business development experience, including significant experience selling software, cloud, data, or AI solutions to U.S. government customers.\n\n - A demonstrated record of building pipeline, exceeding quota, and closing complex six- and seven-figure opportunities with long sales cycles and multiple technical, mission, executive, and procurement stakeholders.\n\n - Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles.\n\n - Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public.\n\n - A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners.\n\n - Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity.\n\n - The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward.\n\n - Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps.\n\n - A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve.\n\n - Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions.\n\n\nEVEN BETTER...\n\n - Experience helping launch or scale a public sector business for a high-growth software company.\n\n - Established relationships across Federal civilian agencies, state governments, or the government contractor and systems integrator ecosystem.\n\n - Familiarity with the FAR and related acquisition frameworks, government cloud and security requirements, and the commercial implications of FedRAMP High.\n\n - Experience shaping and closing outcome-based, usage-based, or other nontraditional software agreements in the public sector.\n\n - Experience with AI, conversational systems, customer experience technology, contact centers, or digital government services—and the ability to speak credibly with both mission and technical leaders.\n\n - Experience operating alongside founders or senior executives in high-stakes customer and partner engagements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1131407f-e70a-4a23-9abc-3124c107d54a","title":"University Recruiter","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-11T13:55:22.856+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1131407f-e70a-4a23-9abc-3124c107d54a","applyUrl":"https://jobs.ashbyhq.com/sierra/1131407f-e70a-4a23-9abc-3124c107d54a/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead full-cycle recruitment processes, from sourcing and screening to closing and onboarding, ensuring a seamless and positive candidate experience.
Identify and engage with passive candidates through various channels, including online platforms, networking events, and industry connections, to build a strong, diverse talent pipeline.
Drive initiatives to ensure diverse hiring practices and build a team reflective of our values and culture.
Utilize metrics and analytics to track recruiting performance, identify areas for improvement, and optimize processes to achieve hiring targets, reporting regularly to hiring partners.
Develop and execute our campus recruiting strategy, building relationships with universities and student communities, and representing Sierra on campus through recruiting events, career fairs, and other programs that build awareness and attract exceptional early-career talent.
Help build and run Sierra’s internship and early-career programs, from campus recruiting and events to creating a high-quality intern experience that engages, develops, and converts exceptional early talent.
5+ years of full-cycle or university recruiting experience, preferably in a fast-paced, high-growth tech environment.
Proven ability to develop and execute recruiting strategies that align with business objectives.
Proficiency in using recruiting metrics and data to inform decisions and improve processes.
Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.
Relationships with career centers, student orgs, faculty, and ambassadors.
Experience in planning and executing campus engagement strategies, across universities through targeted events and partnerships.
Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.
Ability and willingness to travel during peak recruiting cycles and work flexible hours as needed
An interest in building from the ground up: launching intern programs, designing early talent hiring process
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO:\n\n - Lead full-cycle recruitment processes, from sourcing and screening to closing and onboarding, ensuring a seamless and positive candidate experience.\n\n - Identify and engage with passive candidates through various channels, including online platforms, networking events, and industry connections, to build a strong, diverse talent pipeline.\n\n - Drive initiatives to ensure diverse hiring practices and build a team reflective of our values and culture.\n\n - Utilize metrics and analytics to track recruiting performance, identify areas for improvement, and optimize processes to achieve hiring targets, reporting regularly to hiring partners.\n\n - Develop and execute our campus recruiting strategy, building relationships with universities and student communities, and representing Sierra on campus through recruiting events, career fairs, and other programs that build awareness and attract exceptional early-career talent.\n\n - Help build and run Sierra’s internship and early-career programs, from campus recruiting and events to creating a high-quality intern experience that engages, develops, and converts exceptional early talent.\n\n\nWHAT YOU'LL BRING:\n\n - 5+ years of full-cycle or university recruiting experience, preferably in a fast-paced, high-growth tech environment.\n\n - Proven ability to develop and execute recruiting strategies that align with business objectives.\n\n - Proficiency in using recruiting metrics and data to inform decisions and improve processes.\n\n - Strong collaboration skills with a willingness to work cross-functionally to achieve Sierra’s goals.\n\n - Relationships with career centers, student orgs, faculty, and ambassadors.\n\n - Experience in planning and executing campus engagement strategies, across universities through targeted events and partnerships.\n\n\nEVEN BETTER...\n\n - Ability to navigate ambiguity in order to adapt to the ever-changing needs of a growing organization.\n\n - Ability and willingness to travel during peak recruiting cycles and work flexible hours as needed\n\n - An interest in building from the ground up: launching intern programs, designing early talent hiring process\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"149f368c-52d5-408f-ba26-ad888f318a00","title":"Software Engineer, Agent (New Grad 2027)","department":"Early Career","team":"Agent Engineering New Grad","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-08-31T17:54:40.218+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/149f368c-52d5-408f-ba26-ad888f318a00","applyUrl":"https://jobs.ashbyhq.com/sierra/149f368c-52d5-408f-ba26-ad888f318a00/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"bde6daf0-ee01-4470-b1b2-77fc8d232f06","title":"Enterprise Sales Engineer, Consumer Business Services","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-08-21T18:44:44.574+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/bde6daf0-ee01-4470-b1b2-77fc8d232f06","applyUrl":"https://jobs.ashbyhq.com/sierra/bde6daf0-ee01-4470-b1b2-77fc8d232f06/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.
This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.
Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.
GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience translating code, technical logic and user requirements to product and engineering requirements.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE CONSUMER BUSINESS SERVICES TEAM\n\n - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.\n\n - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.\n\n - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.\n\n\nWHAT YOU'LL DO\n\n - GTM technical expert: Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales.\n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience translating code, technical logic and user requirements to product and engineering requirements.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"ef6ee85e-597e-49cd-b2fb-c304b8f3cda7","title":"IT Support Specialist","department":"IT","team":"IT","employmentType":"Contract","location":"New York, NY","secondaryLocations":[],"publishedAt":"2026-08-21T22:50:42.138+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/ef6ee85e-597e-49cd-b2fb-c304b8f3cda7","applyUrl":"https://jobs.ashbyhq.com/sierra/ef6ee85e-597e-49cd-b2fb-c304b8f3cda7/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an IT Support Specialist in New York, you'll be the hands-on, on-the-ground owner of day-to-day IT for one of our fastest-growing offices. You'll be the first person teammates turn to when something isn't working, and the person who makes sure hardware, conference rooms, and the office network simply work. This is a role for someone who thrives in execution mode and enjoys solving problems quickly and efficiently. Your responsibilities will include:
IT Support: Serve as the first line of defense for employee IT issues in New York, with deep focus on macOS troubleshooting, application support, and network connectivity.
Global Support Queue: Share responsibility for Sierra's global IT helpdesk queue during your regional working hours: triage new requests, resolve issues across offices, keep ownership clear, coordinate escalation, and provide clean cross-time-zone handoffs.
Technical User Support: Support engineers and other highly technical teammates with curiosity and confidence, using logs, command-line tools, and clear written communication when appropriate.
AI-Assisted Troubleshooting: Use approved AI tools thoughtfully to accelerate research, hypothesis generation, and documentation while protecting sensitive data and independently validating consequential recommendations.
Hardware Management: Own the full device lifecycle locally—procurement, deployment, inventory tracking, loaner pool oversight, and device re-provisioning for offboarded users.
AV & Conference Rooms: Keep every room meeting-ready. Maintain and troubleshoot conference room AV, proactively test rooms, and own the peripheral and accessory inventory.
Office Build-Out & Moves: Partner with Facilities, our project managers, and AV integrators to spec, stage, and commission IT and AV for our new New York space, and support the move from our current location.
Network & Vendor Coordination: Triage office network and connectivity issues, then drive them to resolution with our ISP, network, and building vendors.
IT Onboarding: Set up laptops and essential software for new hires, delivering a seamless first-day experience.
SaaS Administration: Handle routine administration in Okta, Google Workspace, and other core applications, including users and groups, app assignments, access changes, licensing, and basic audit-log review.
IT Projects: Take on well-scoped endpoint, SaaS, access, inventory, or workplace technology projects with clear success criteria, appropriate review, testing, documentation, and rollback planning.
Process Improvement: Look beyond the immediate ticket, respectfully challenge inefficient or fragile practices, propose practical improvements, and help implement and document better ways of working.
IT Logistics: Support software installs, device shipments to East Coast teammates, repair and warranty coordination, and proactive hardware refresh planning.
Experience: 2-5 years in hands-on IT support or systems administration, with strong macOS experience in a fast-paced or startup environment.
Technical Proficiency: Comfort with endpoint management and MDM systems (e.g., Jamf), identity tooling (e.g., Okta), and troubleshooting across Mac hardware and software.
SaaS Foundations: Hands-on experience with basic Okta, Google Workspace, or comparable SaaS administration and a desire to grow into broader systems ownership.
Engineering Environment: Experience supporting engineers or other highly technical users, or clear evidence that you can communicate credibly, work from technical evidence, and learn unfamiliar systems quickly.
Troubleshooting Judgment: A structured, hypothesis-driven approach; strong follow-through; and the judgment to recognize uncertainty, seek review, or escalate before a risky change.
Queue Ownership: Able to manage competing requests in a shared global queue, communicate priorities, maintain accurate status, and carry issues through resolution or a clear handoff.
Continuous Improvement: Curious about why work is done a certain way and comfortable constructively challenging the status quo with specific, practical recommendations.
AV & Network Fluency: Practical troubleshooting of conference room AV and office networking fundamentals—Wi-Fi, DHCP, VLANs—and the judgment to know when to escalate to a vendor.
Organization: Highly organized with a systems-oriented mindset—able to track devices, accessories, and inventory accurately across multiple offices.
Execution Focused: Bias for action and the ability to troubleshoot, solve problems, and follow through without constant direction, while knowing when to seek review or escalate.
Communication: Friendly, clear communicator who can help teammates quickly and patiently—whether they're in-office or remote.
Work model: This role is based in our New York office, with in-office work Monday through Thursday and remote work on Fridays.
Experience supporting an office build-out, relocation, or new-site commissioning from the IT and AV side.
Familiarity with Zoom Rooms and hardware such as Neat, Logitech, or Poly.
Past experience with Apple Business Manager or zero-touch deployment tools.
Passion for documentation, process improvement, and enabling others to solve simple issues themselves.
Change-Control Exposure: Familiarity with version control, peer review, staged rollout, rollback planning, infrastructure or configuration as code, or other disciplined change practices.
Automation: Experience using APIs, scripts, Terraform, or similar tools to make routine administration safer and more repeatable.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs an IT Support Specialist in New York, you'll be the hands-on, on-the-ground owner of day-to-day IT for one of our fastest-growing offices. You'll be the first person teammates turn to when something isn't working, and the person who makes sure hardware, conference rooms, and the office network simply work. This is a role for someone who thrives in execution mode and enjoys solving problems quickly and efficiently. Your responsibilities will include:\n\n - IT Support: Serve as the first line of defense for employee IT issues in New York, with deep focus on macOS troubleshooting, application support, and network connectivity.\n\n - Global Support Queue: Share responsibility for Sierra's global IT helpdesk queue during your regional working hours: triage new requests, resolve issues across offices, keep ownership clear, coordinate escalation, and provide clean cross-time-zone handoffs.\n\n - Technical User Support: Support engineers and other highly technical teammates with curiosity and confidence, using logs, command-line tools, and clear written communication when appropriate.\n\n - AI-Assisted Troubleshooting: Use approved AI tools thoughtfully to accelerate research, hypothesis generation, and documentation while protecting sensitive data and independently validating consequential recommendations.\n\n - Hardware Management: Own the full device lifecycle locally—procurement, deployment, inventory tracking, loaner pool oversight, and device re-provisioning for offboarded users.\n\n - AV & Conference Rooms: Keep every room meeting-ready. Maintain and troubleshoot conference room AV, proactively test rooms, and own the peripheral and accessory inventory.\n\n - Office Build-Out & Moves: Partner with Facilities, our project managers, and AV integrators to spec, stage, and commission IT and AV for our new New York space, and support the move from our current location.\n\n - Network & Vendor Coordination: Triage office network and connectivity issues, then drive them to resolution with our ISP, network, and building vendors.\n\n - IT Onboarding: Set up laptops and essential software for new hires, delivering a seamless first-day experience.\n\n - SaaS Administration: Handle routine administration in Okta, Google Workspace, and other core applications, including users and groups, app assignments, access changes, licensing, and basic audit-log review.\n\n - IT Projects: Take on well-scoped endpoint, SaaS, access, inventory, or workplace technology projects with clear success criteria, appropriate review, testing, documentation, and rollback planning.\n\n - Process Improvement: Look beyond the immediate ticket, respectfully challenge inefficient or fragile practices, propose practical improvements, and help implement and document better ways of working.\n\n - IT Logistics: Support software installs, device shipments to East Coast teammates, repair and warranty coordination, and proactive hardware refresh planning.\n\n\nWHAT YOU’LL BRING\n\n - Experience: 2-5 years in hands-on IT support or systems administration, with strong macOS experience in a fast-paced or startup environment.\n\n - Technical Proficiency: Comfort with endpoint management and MDM systems (e.g., Jamf), identity tooling (e.g., Okta), and troubleshooting across Mac hardware and software.\n\n - SaaS Foundations: Hands-on experience with basic Okta, Google Workspace, or comparable SaaS administration and a desire to grow into broader systems ownership.\n\n - Engineering Environment: Experience supporting engineers or other highly technical users, or clear evidence that you can communicate credibly, work from technical evidence, and learn unfamiliar systems quickly.\n\n - Troubleshooting Judgment: A structured, hypothesis-driven approach; strong follow-through; and the judgment to recognize uncertainty, seek review, or escalate before a risky change.\n\n - Queue Ownership: Able to manage competing requests in a shared global queue, communicate priorities, maintain accurate status, and carry issues through resolution or a clear handoff.\n\n - Continuous Improvement: Curious about why work is done a certain way and comfortable constructively challenging the status quo with specific, practical recommendations.\n\n - AV & Network Fluency: Practical troubleshooting of conference room AV and office networking fundamentals—Wi-Fi, DHCP, VLANs—and the judgment to know when to escalate to a vendor.\n\n - Organization: Highly organized with a systems-oriented mindset—able to track devices, accessories, and inventory accurately across multiple offices.\n\n - Execution Focused: Bias for action and the ability to troubleshoot, solve problems, and follow through without constant direction, while knowing when to seek review or escalate.\n\n - Communication: Friendly, clear communicator who can help teammates quickly and patiently—whether they're in-office or remote.\n\n - Work model: This role is based in our New York office, with in-office work Monday through Thursday and remote work on Fridays.\n\n\nEVEN BETTER…\n\n - Experience supporting an office build-out, relocation, or new-site commissioning from the IT and AV side.\n\n - Familiarity with Zoom Rooms and hardware such as Neat, Logitech, or Poly.\n\n - Past experience with Apple Business Manager or zero-touch deployment tools.\n\n - Passion for documentation, process improvement, and enabling others to solve simple issues themselves.\n\n - Change-Control Exposure: Familiarity with version control, peer review, staged rollout, rollback planning, infrastructure or configuration as code, or other disciplined change practices.\n\n - Automation: Experience using APIs, scripts, Terraform, or similar tools to make routine administration safer and more repeatable.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"cb841dfe-5d21-44ae-8496-fca6b5587ae6","title":"Product Manager, Agent Development - Public Sector","department":"Product","team":"Agent Product Management","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-08-24T18:06:54.065+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/cb841dfe-5d21-44ae-8496-fca6b5587ae6","applyUrl":"https://jobs.ashbyhq.com/sierra/cb841dfe-5d21-44ae-8496-fca6b5587ae6/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Build enterprise-grade AI agents for government institutions: As an Agent Product Manager at Sierra, you will partner directly with our engineers and public sector customers to build and ship AI agents that serve people across high-stakes, mission-critical interactions. These agents will help constituents navigate complex programs, complete important tasks, and get timely, trustworthy support while meeting the security, accessibility, and reliability standards government work demands.
Discover where agents can make the greatest impact: Ground-up discovery is a critical part of the role. Work closely with federal and state institutions to understand their missions, operating constraints, constituent needs, and service-delivery workflows. Identify and prioritize new opportunities for AI agents to improve access, responsiveness, and outcomes.
Engage with customers at every level: Become a trusted advisor to public sector leaders and a hands-on partner to their working teams. Discover and assess requirements, prepare and present demonstrations, navigate technical and operational challenges with customer counterparts, and continuously improve agents to fit each institution’s policies and workflows.
Own outcomes from concept through production: Translate mission goals into a clear product strategy, roadmap, and measurable definition of success. Coordinate across customer stakeholders, engineering, design, research, security, and operations to take agents from initial concept through launch and ongoing iteration.
Shape the platform and public sector roadmap: Your direct work with government institutions will guide the evolution of Sierra’s core platform. Surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform teams to shape the future of AI agent development for the public sector.
Help build Sierra’s public sector business: Partner closely with public sector leadership on market strategy, product investments, and repeatable approaches that allow the team to scale quickly while preserving the trust and craftsmanship our customers expect.
These are examples of projects our healthcare team has worked on:
Build agents that help people understand eligibility, apply for benefits, check case status, and navigate complex social-service programs.
Develop secure reporting experiences that make it easier to report fraud, waste, abuse, or other concerns and route each submission appropriately.
Create voice and chat agents that answer questions about licenses, permits, taxes, public records, and other high-volume government services across languages and channels.
Design proactive and long-horizon agents that keep constituents informed, collect missing information, and guide them through multi-step government processes over time.
Turn patterns in constituent conversations into actionable insights that help public officials understand emerging needs and improve service delivery.
5-7+ years of experience developing highly technical products.
Experience in Product Management or a similar product development role at or above the level of Senior Product Manager.
A passion for public sector work and a belief in the potential of our institutions to transform outcomes for the people they serve.
Comfort working directly with customers to understand their needs, navigate complex organizations, and solve real-world problems. A core part of the role is coordinating directly with public servants and technical stakeholders to understand their workflows.
Experience crafting and tailoring messages for different audiences, including senior executives and public sector leaders.
Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent developments in AI.
Strong product judgment and a track record of driving ambiguous, cross-functional initiatives from discovery through launch and measurable impact.
A degree in a technical or related field, or equivalent professional experience.
Experience building or deploying AI/LLM products, especially conversational or long-horizon agents, and familiarity with evaluation, retrieval, prompt engineering, or agent tooling.
Experience with government technology or working with public sector institutions, including an understanding of procurement, regulation, security, accessibility, and patterns of partnership.
A demonstrated track record of operating in ambiguity, for example as part of a founding team, a new initiative within a large organization, or a forward-deployed product or engineering team.
Some coding experience with React, TypeScript, and Go, or experience prototyping technical products directly with engineers.
An MBA or equivalent professional experience at the intersection of technology, operations, and strategy.
Past roles that involved working directly with end customers to influence software development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU'LL DO\n\n - Build enterprise-grade AI agents for government institutions: As an Agent Product Manager at Sierra, you will partner directly with our engineers and public sector customers to build and ship AI agents that serve people across high-stakes, mission-critical interactions. These agents will help constituents navigate complex programs, complete important tasks, and get timely, trustworthy support while meeting the security, accessibility, and reliability standards government work demands.\n\n - Discover where agents can make the greatest impact: Ground-up discovery is a critical part of the role. Work closely with federal and state institutions to understand their missions, operating constraints, constituent needs, and service-delivery workflows. Identify and prioritize new opportunities for AI agents to improve access, responsiveness, and outcomes.\n\n - Engage with customers at every level: Become a trusted advisor to public sector leaders and a hands-on partner to their working teams. Discover and assess requirements, prepare and present demonstrations, navigate technical and operational challenges with customer counterparts, and continuously improve agents to fit each institution’s policies and workflows.\n\n - Own outcomes from concept through production: Translate mission goals into a clear product strategy, roadmap, and measurable definition of success. Coordinate across customer stakeholders, engineering, design, research, security, and operations to take agents from initial concept through launch and ongoing iteration.\n\n - Shape the platform and public sector roadmap: Your direct work with government institutions will guide the evolution of Sierra’s core platform. Surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform teams to shape the future of AI agent development for the public sector.\n\n - Help build Sierra’s public sector business: Partner closely with public sector leadership on market strategy, product investments, and repeatable approaches that allow the team to scale quickly while preserving the trust and craftsmanship our customers expect.\n\n\nEXAMPLE PROJECTS\n\nThese are examples of projects our healthcare team has worked on:\n\n - Build agents that help people understand eligibility, apply for benefits, check case status, and navigate complex social-service programs.\n\n - Develop secure reporting experiences that make it easier to report fraud, waste, abuse, or other concerns and route each submission appropriately.\n\n - Create voice and chat agents that answer questions about licenses, permits, taxes, public records, and other high-volume government services across languages and channels.\n\n - Design proactive and long-horizon agents that keep constituents informed, collect missing information, and guide them through multi-step government processes over time.\n\n - Turn patterns in constituent conversations into actionable insights that help public officials understand emerging needs and improve service delivery.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years of experience developing highly technical products.\n\n - Experience in Product Management or a similar product development role at or above the level of Senior Product Manager.\n\n - A passion for public sector work and a belief in the potential of our institutions to transform outcomes for the people they serve.\n\n - Comfort working directly with customers to understand their needs, navigate complex organizations, and solve real-world problems. A core part of the role is coordinating directly with public servants and technical stakeholders to understand their workflows.\n\n - Experience crafting and tailoring messages for different audiences, including senior executives and public sector leaders.\n\n - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent developments in AI.\n\n - Strong product judgment and a track record of driving ambiguous, cross-functional initiatives from discovery through launch and measurable impact.\n\n - A degree in a technical or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM products, especially conversational or long-horizon agents, and familiarity with evaluation, retrieval, prompt engineering, or agent tooling.\n\n - Experience with government technology or working with public sector institutions, including an understanding of procurement, regulation, security, accessibility, and patterns of partnership.\n\n - A demonstrated track record of operating in ambiguity, for example as part of a founding team, a new initiative within a large organization, or a forward-deployed product or engineering team.\n\n - Some coding experience with React, TypeScript, and Go, or experience prototyping technical products directly with engineers.\n\n - An MBA or equivalent professional experience at the intersection of technology, operations, and strategy.\n\n - Past roles that involved working directly with end customers to influence software development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f5a8fe57-ea2d-4e62-91d8-80c439fca299","title":"Enterprise Sales Director","department":"Sales","team":"Sales","employmentType":"FullTime","location":"South Korea","secondaryLocations":[],"publishedAt":"2026-08-25T14:10:13.051+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"South Korea"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f5a8fe57-ea2d-4e62-91d8-80c439fca299","applyUrl":"https://jobs.ashbyhq.com/sierra/f5a8fe57-ea2d-4e62-91d8-80c439fca299/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.
Strong communication skills: Strong English and Korean written and verbal communication.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals.\n\n - Strong communication skills: Strong English and Korean written and verbal communication.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7730850d-d537-4c9a-8526-c8c772c9914a","title":"Communications & Marketing Manager, Japan","department":"Marketing & Communications","team":"Marketing & Communications","employmentType":"FullTime","location":"Tokyo","secondaryLocations":[],"publishedAt":"2026-10-02T01:35:59.878+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Japan"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7730850d-d537-4c9a-8526-c8c772c9914a","applyUrl":"https://jobs.ashbyhq.com/sierra/7730850d-d537-4c9a-8526-c8c772c9914a/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Set the standard for great marketing and PR in a hyper growth, founder-led company.
Work cross functionally to raise awareness of Sierra.
Maintain overall responsibility for local marketing as well as press, public speaking and social media.
Be a key part of Sierra’s global Marcomms team — pitching in as needed.
Deep knowledge of Japan and the Japanese tech/business environment.
Entrepreneurial and scrappy — you like to try new things, and you lean into risk.
A problem solver — you roll up your sleeves and solve what’s thrown at you.
Fast and calm — you move quickly and are poised under pressure.
Strong execution — you deliver what you promise, to a high standard.
Creative — you can set the standard for what drives conversation in enterprise PR.
Excellent communicator — you have strong written and verbal communications.
Great team player — you’re low ego and enjoy working with people at every level. You are good at building and maintaining relationships, internally and externally.
Understanding of marketing, the press and social media — either from working at a company, in government or as a journalist.
Good judgement and professionalism — you can navigate ambiguity and can be trusted with sensitive or confidential initiatives.
Proven track record working in a fast paced company.
Strong written and spoken English and Japanese.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Set the standard for great marketing and PR in a hyper growth, founder-led company.\n\n - Work cross functionally to raise awareness of Sierra.\n\n - Maintain overall responsibility for local marketing as well as press, public speaking and social media.\n\n - Be a key part of Sierra’s global Marcomms team — pitching in as needed.\n\n\nWHAT YOU’LL BRING\n\n - Deep knowledge of Japan and the Japanese tech/business environment.\n\n - Entrepreneurial and scrappy — you like to try new things, and you lean into risk.\n\n - A problem solver — you roll up your sleeves and solve what’s thrown at you.\n\n - Fast and calm — you move quickly and are poised under pressure.\n\n - Strong execution — you deliver what you promise, to a high standard.\n\n - Creative — you can set the standard for what drives conversation in enterprise PR.\n\n - Excellent communicator — you have strong written and verbal communications.\n\n - Great team player — you’re low ego and enjoy working with people at every level. You are good at building and maintaining relationships, internally and externally.\n\n - Understanding of marketing, the press and social media — either from working at a company, in government or as a journalist.\n\n - Good judgement and professionalism — you can navigate ambiguity and can be trusted with sensitive or confidential initiatives.\n\n\nEVEN BETTER\n\n - Proven track record working in a fast paced company.\n\n - Strong written and spoken English and Japanese.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"cfb17e80-6326-44b2-9c33-1f6e6cb0835b","title":"Enterprise Sales Director, Nordics","department":"Sales","team":"Sales","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-10-02T13:34:21.302+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/cfb17e80-6326-44b2-9c33-1f6e6cb0835b","applyUrl":"https://jobs.ashbyhq.com/sierra/cfb17e80-6326-44b2-9c33-1f6e6cb0835b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Strong communication skills: Exceptional verbal and written communication abilities in English, with fluency in Swedish, Norwegian, or Danish.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. \n\n - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.\n\n - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.\n\n - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.\n\n - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. \n\n - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.\n\n - Strong communication skills: Exceptional verbal and written communication abilities in English, with fluency in Swedish, Norwegian, or Danish.\n\n - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3258c9bc-1bae-4bd1-89d2-9d8a545e9f7b","title":"Area Vice President, Consumer Business Services","department":"Sales","team":"Sales","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-09-04T17:12:56.584+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3258c9bc-1bae-4bd1-89d2-9d8a545e9f7b","applyUrl":"https://jobs.ashbyhq.com/sierra/3258c9bc-1bae-4bd1-89d2-9d8a545e9f7b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.
This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.
Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.
Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.
People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE CONSUMER BUSINESS SERVICES TEAM\n\n - Sierra partners with the businesses that power everyday life for consumers and enterprises alike — from the CPG brands on every shelf to the logistics networks that get products there, the real estate and facilities teams that manage the buildings people live and work in, and the energy and utility providers that keep the lights on. Our agents handle everything from order tracking and account management to field service scheduling and billing support, tuned to the voice and workflows of each business.\n\n - This vertical spans a wide range of industries — consumer products, commercial real estate, automotive & mobility, transportation & logistics, industrial manufacturing, information & data services, consumer electronics, professional services, facilities management, construction, energy, and utilities — giving you the breadth to build relationships across some of the largest and most established companies in the world.\n\n - Join us to bring AI agents to the businesses that quietly run the economy — and help build technology that makes these essential services faster, more reliable, and more human for everyone who depends on them.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong communication skills: Exceptional verbal and written communication abilities.\n\n - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows.\n\n - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"34b31b67-268c-4270-b48f-72e59064c96e","title":"Software Engineer Intern, Agent (Summer 2027)","department":"Early Career","team":"Intern","employmentType":"Intern","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-08-31T21:42:19.593+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/34b31b67-268c-4270-b48f-72e59064c96e","applyUrl":"https://jobs.ashbyhq.com/sierra/34b31b67-268c-4270-b48f-72e59064c96e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.
Pursuing a bachelor's or master's degree in computer science or a related field
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
The intern program is open to students graduating December 2027 - June 2028
Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nAs a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.\n\n \n\n\nWHAT YOU'LL BRING\n\n - Pursuing a bachelor's or master's degree in computer science or a related field\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER\n\n - Experience building or deploying AI/LLM systems in production\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n\nINTERN QUALIFICATIONS\n\n - The intern program is open to students graduating December 2027 - June 2028\n\n - Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d9c445da-c7b4-43a3-8d71-d367681c3015","title":"APX (New Grad 2027)","department":"Early Career","team":"APX","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-08-31T22:47:06.440+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d9c445da-c7b4-43a3-8d71-d367681c3015","applyUrl":"https://jobs.ashbyhq.com/sierra/d9c445da-c7b4-43a3-8d71-d367681c3015/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
APX is Sierra’s rotational program to develop the next generation of AI builders.
In the age of AI, we believe generalists with diverse training and experience will become more important and empowered than ever. Instead of specializing early in an engineering, product management, or business subfield, the next generation of AI leaders will be able to do everything it takes to create, ship, and distribute great products.
As an APX, you’ll be among the first to live in this exciting future. You’ll build AI agents directly with top global brands and gain access to comprehensive training opportunities and rotations across our Agent Development and Core Product teams. If you’re hungry to shape the most important technological wave of our lifetimes, come build at Sierra.
The APX program is open to students graduating from undergraduate or Master’s programs by June 2027.
Build and ship AI agents with Sierra’s customers in a fast-paced, production environment.
Contribute directly to Sierra’s platform by writing code and designing products.
Learn how we build agents that operate at scale and evolve through real-world usage.
Collaborate closely with engineers, product managers, and operators across the company.
Participate in internal reviews and product discussions to push the boundaries of what agents can do.
Pursuing a Bachelor’s or Master’s degree (or comparable program) in Computer Science or a related field.
Professional experience in software engineering or product management, especially with customer-facing responsibilities.
Expertise in React, TypeScript, Python, Go, and other modern programming languages.
Demonstrated curiosity and interest in AI applications (e.g., research, jobs, side projects).
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nPROGRAM OVERVIEW\n\n - APX is Sierra’s rotational program to develop the next generation of AI builders.\n\n - In the age of AI, we believe generalists with diverse training and experience will become more important and empowered than ever. Instead of specializing early in an engineering, product management, or business subfield, the next generation of AI leaders will be able to do everything it takes to create, ship, and distribute great products.\n\n - As an APX, you’ll be among the first to live in this exciting future. You’ll build AI agents directly with top global brands and gain access to comprehensive training opportunities and rotations across our Agent Development and Core Product teams. If you’re hungry to shape the most important technological wave of our lifetimes, come build at Sierra.\n\n - The APX program is open to students graduating from undergraduate or Master’s programs by June 2027.\n\n\nWHAT YOU’LL DO\n\n - Build and ship AI agents with Sierra’s customers in a fast-paced, production environment.\n\n - Contribute directly to Sierra’s platform by writing code and designing products.\n\n - Learn how we build agents that operate at scale and evolve through real-world usage.\n\n - Collaborate closely with engineers, product managers, and operators across the company.\n\n - Participate in internal reviews and product discussions to push the boundaries of what agents can do.\n\n\nWHAT YOU'LL BRING\n\n - Pursuing a Bachelor’s or Master’s degree (or comparable program) in Computer Science or a related field.\n\n - Professional experience in software engineering or product management, especially with customer-facing responsibilities.\n\n - Expertise in React, TypeScript, Python, Go, and other modern programming languages.\n\n - Demonstrated curiosity and interest in AI applications (e.g., research, jobs, side projects).\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"e963514d-8b85-4747-9620-cf9a66ce9b4c","title":"Executive Assistant, Office of the Co-Founders","department":"Operations","team":"Executive Assistant","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-01T20:18:24.867+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/e963514d-8b85-4747-9620-cf9a66ce9b4c","applyUrl":"https://jobs.ashbyhq.com/sierra/e963514d-8b85-4747-9620-cf9a66ce9b4c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Executive Assistant supporting the Office of the Co-Founders at Sierra, you will provide a wide range of strategic and administrative support to our Co-Founders and their teams.
Play a pivotal, high-trust role in a dynamic, fast-paced environment. You’ll partner closely with the existing executive support team to execute complex logistics, travel, meetings, events, and special projects with precision and foresight.
Act as a second assistant to our Co-Founders, coordinating complex travel, running logistics for all onsite meetings, helping the team with projects (large trip planning, events, etc) and generally be ready and able to jump in when extra support is needed.
Anticipate needs, identify potential issues, and proactively develop solutions that keep priorities and commitments moving forward.
Serve as a trusted liaison to internal teams, vendors, and external partners, building strong relationships while safeguarding the priorities of the Office of the Co-Founders.
Plan and execute leadership travel, team off-sites, executive dinners, on-site meetings, and other internal or personal events as needed.
Take ownership of evolving requests and projects, remaining flexible and ready to provide additional support wherever it is most needed.
Handle sensitive information and materials with the utmost confidentiality, discretion, and sound judgment.
3+ years of experience in executive support or a similar high-level administrative role.
Willingness and ability to work on-site in San Francisco up to five days per week, including consistent presence when the co-founders are on-site.
Exceptional attention to detail and an anticipatory, white-glove service mindset, with the ability to operate independently and deliver polished, seamless support with limited direction.
Exceptional organizational and time-management skills, with the ability to manage competing priorities accurately in a fast-paced environment.
Proven ability to partner effectively with senior executives, cross-functional teams, vendors, and external stakeholders.
Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly.
Experience in a fast-growing, in-person start-up environment.
Experience working with C-suite executives.
Experience working within a dual, floating, or team-based Executive Assistant structure.
Experience managing complex travel, executive events, and high-touch on-site logistics.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - As an Executive Assistant supporting the Office of the Co-Founders at Sierra, you will provide a wide range of strategic and administrative support to our Co-Founders and their teams.\n\n - Play a pivotal, high-trust role in a dynamic, fast-paced environment. You’ll partner closely with the existing executive support team to execute complex logistics, travel, meetings, events, and special projects with precision and foresight.\n\n - Act as a second assistant to our Co-Founders, coordinating complex travel, running logistics for all onsite meetings, helping the team with projects (large trip planning, events, etc) and generally be ready and able to jump in when extra support is needed.\n\n - Anticipate needs, identify potential issues, and proactively develop solutions that keep priorities and commitments moving forward.\n\n - Serve as a trusted liaison to internal teams, vendors, and external partners, building strong relationships while safeguarding the priorities of the Office of the Co-Founders.\n\n - Plan and execute leadership travel, team off-sites, executive dinners, on-site meetings, and other internal or personal events as needed.\n\n - Take ownership of evolving requests and projects, remaining flexible and ready to provide additional support wherever it is most needed.\n\n - Handle sensitive information and materials with the utmost confidentiality, discretion, and sound judgment.\n\n\nWHAT YOU'LL BRING\n\n - 3+ years of experience in executive support or a similar high-level administrative role.\n\n - Willingness and ability to work on-site in San Francisco up to five days per week, including consistent presence when the co-founders are on-site.\n\n - Exceptional attention to detail and an anticipatory, white-glove service mindset, with the ability to operate independently and deliver polished, seamless support with limited direction.\n\n - Exceptional organizational and time-management skills, with the ability to manage competing priorities accurately in a fast-paced environment.\n\n - Proven ability to partner effectively with senior executives, cross-functional teams, vendors, and external stakeholders.\n\n - Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly.\n\n\nEVEN BETTER...\n\n - Experience in a fast-growing, in-person start-up environment.\n\n - Experience working with C-suite executives.\n\n - Experience working within a dual, floating, or team-based Executive Assistant structure.\n\n - Experience managing complex travel, executive events, and high-touch on-site logistics.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d8baf20a-4c20-496d-9f0c-bc47a25fddb8","title":"GTM Operations, Agent Development (London)","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-02T21:42:11.259+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d8baf20a-4c20-496d-9f0c-bc47a25fddb8","applyUrl":"https://jobs.ashbyhq.com/sierra/d8baf20a-4c20-496d-9f0c-bc47a25fddb8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Support the business of Agent Development: Serve as the strategy and operations partner to Agent Dev leadership, and bring the same operational rigor to Agent Dev that powers our Sales organization.
Stand up the operating cadence: Partner with Agent Dev leaders to provide clear visibility into business health, including pipeline, deployment progress, utilization, expansion opportunities, and risks.
Operationalize best practices for enterprise agent deployment: Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises.
Drive account expansion strategy: Work closely with account teams to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.
Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high leverage decisions.
Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage across Agent Dev.
5-7 years of experience in management consulting, investment banking, private equity, or strategy and operations at top-tier technology companies.
Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.
Demonstrated experience supporting sales, post-sales, or commercial teams in a strategy and operations capacity.
Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.
Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.
Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.
A growth mindset, coachability, and willingness to roll up your sleeves. No task is too small if it helps the team win.
Technical fluency and coding comfort: You have built apps or internal tools before and can confidently use AI coding tools such as Claude Code, Cursor, or Codex to create production-ready internal solutions.
Previous 0-1 operating experience at a growth stage technology company.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Support the business of Agent Development: Serve as the strategy and operations partner to Agent Dev leadership, and bring the same operational rigor to Agent Dev that powers our Sales organization.\n\n - Stand up the operating cadence: Partner with Agent Dev leaders to provide clear visibility into business health, including pipeline, deployment progress, utilization, expansion opportunities, and risks.\n\n - Operationalize best practices for enterprise agent deployment: Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises.\n\n - Drive account expansion strategy: Work closely with account teams to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth.\n\n - Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high leverage decisions.\n\n - Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage across Agent Dev.\n\n\nWHAT YOU’LL BRING\n\n - 5-7 years of experience in management consulting, investment banking, private equity, or strategy and operations at top-tier technology companies.\n\n - Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions.\n\n - Demonstrated experience supporting sales, post-sales, or commercial teams in a strategy and operations capacity.\n\n - Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution.\n\n - Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded.\n\n - Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor.\n\n - A growth mindset, coachability, and willingness to roll up your sleeves. No task is too small if it helps the team win.\n\n\nEVEN BETTER...\n\n - Technical fluency and coding comfort: You have built apps or internal tools before and can confidently use AI coding tools such as Claude Code, Cursor, or Codex to create production-ready internal solutions.\n\n - Previous 0-1 operating experience at a growth stage technology company.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"79953d72-60d4-43e0-8c8c-6eccda422dce","title":"Software Engineer, Agent (New Grad 2027)","department":"Early Career","team":"Agent Engineering New Grad","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-09-07T02:02:53.490+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/79953d72-60d4-43e0-8c8c-6eccda422dce","applyUrl":"https://jobs.ashbyhq.com/sierra/79953d72-60d4-43e0-8c8c-6eccda422dce/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"eb8e8b58-394b-43f0-b9bd-4f1407d9aa17","title":"Software Engineer Intern, Agent (Summer 2027)","department":"Early Career","team":"Intern","employmentType":"Intern","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-09-07T01:56:26.806+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/eb8e8b58-394b-43f0-b9bd-4f1407d9aa17","applyUrl":"https://jobs.ashbyhq.com/sierra/eb8e8b58-394b-43f0-b9bd-4f1407d9aa17/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.
Pursuing a bachelor's or master's degree in computer science or a related field
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
The intern program is open to students graduating December 2027 - June 2028
Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nAs a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.\n\n \n\n\nWHAT YOU'LL BRING\n\n - Pursuing a bachelor's or master's degree in computer science or a related field\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER\n\n - Experience building or deploying AI/LLM systems in production\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n\nINTERN QUALIFICATIONS\n\n - The intern program is open to students graduating December 2027 - June 2028\n\n - Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"dcd50512-6575-46e5-8c28-b2bcd6acf81f","title":"Strategist, Agent Development (Swedish speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-06T14:00:05.671+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/dcd50512-6575-46e5-8c28-b2bcd6acf81f","applyUrl":"https://jobs.ashbyhq.com/sierra/dcd50512-6575-46e5-8c28-b2bcd6acf81f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"837a134f-6ab3-485f-9cf7-a957cc1b8992","title":"Strategist, Agent Development (Norwegian speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-09-06T14:01:27.493+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/837a134f-6ab3-485f-9cf7-a957cc1b8992","applyUrl":"https://jobs.ashbyhq.com/sierra/837a134f-6ab3-485f-9cf7-a957cc1b8992/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU'LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"32f98c30-916c-41c2-9e10-a7095a81e3b5","title":"Strategist, Agent Development (Spanish speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-08T16:50:37.922+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/32f98c30-916c-41c2-9e10-a7095a81e3b5","applyUrl":"https://jobs.ashbyhq.com/sierra/32f98c30-916c-41c2-9e10-a7095a81e3b5/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"f662fde2-ac88-40aa-96d2-4b2fab82efb8","title":"Partnerships Manager, Government and Public Sector","department":"Partnerships","team":"Partnerships","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-09T16:44:32.479+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/f662fde2-ac88-40aa-96d2-4b2fab82efb8","applyUrl":"https://jobs.ashbyhq.com/sierra/f662fde2-ac88-40aa-96d2-4b2fab82efb8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the end-to-end partnership strategy for Sierra’s US, Canada, and UK Government & SLED ecosystem, identifying, prioritizing, recruiting, and structuring the systems integrator, reseller, distributor, and strategic alliances that will most accelerate Sierra’s growth and expand our public-sector reach.
Build and lead joint go-to-market strategies with key partners, developing compelling joint value propositions, identifying priority accounts and use cases, and aligning sales motions, pipeline goals, and shared success metrics to drive measurable commercial outcomes.
Build a scalable partner program and enablement engine from the ground up, including training, certification paths, sales plays, field-facing materials, commercial frameworks, and onboarding programs that give partners the tools and confidence to effectively position, sell, and deliver Sierra.
Own and grow strategic partner relationships from initial engagement through long-term success, cultivating executive-level sponsorship while establishing the operating rhythms, joint planning, business reviews, governance, and scorecards needed to keep partnerships accountable, productive, and scaling over time.
Serve as the connective tissue between Sierra and the broader public-sector partner ecosystem, partnering closely with Sales, Marketing, Product, and Legal; bringing market intelligence and partner feedback back into Sierra; representing the company at key industry and procurement events; and using pipeline and performance data to determine where to invest, course-correct, or evolve our partnership strategy.
10+ years of experience in strategic partnerships, alliances, or channel strategy, with significant experience across US, Canada, and/or UK Government and SLED markets and a proven track record of building and scaling partner programs that drive engagement and pipeline.
Strong relationships across the government technology ecosystem, including resellers, systems integrators, distributors, and strategic partners such as Carahsoft, Deloitte, Accenture Federal Services, or comparable public-sector organizations.
Deep understanding of government procurement and public-sector requirements, including RFPs/RFIs, cooperative purchasing vehicles, GSA schedules, CCS/G-Cloud frameworks, Canadian procurement vehicles, and relevant compliance, security, and accessibility requirements.
Strong executive presence and relationship-building skills, with a demonstrated ability to earn senior-level trust and sponsorship while developing GTM frameworks, enablement programs, and operating cadences that scale partnerships.
AI fluency and a builder mindset, with experience leveraging AI-powered tools and insights in day-to-day work and applying that knowledge to partnerships around an AI-native product like Sierra, along with the ability to travel across the US, Canada, and UK as needed.
Experience working at or partnering closely with government-focused organizations such as Carahsoft, Deloitte, or Accenture Federal, ideally within a high-growth enterprise company where you helped build and scale a public-sector partner ecosystem.
Experience structuring and growing strategic partnerships, including negotiating commercial terms, developing co-sell and governance frameworks, and driving joint GTM initiatives, customer events, executive engagement, and partner marketing programs.
Knowledge of the government technology landscape, ideally including CX/customer service technology, AI/ML applications and public-sector AI policy/procurement trends, with an existing security clearance or eligibility to obtain one where applicable.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the end-to-end partnership strategy for Sierra’s US, Canada, and UK Government & SLED ecosystem, identifying, prioritizing, recruiting, and structuring the systems integrator, reseller, distributor, and strategic alliances that will most accelerate Sierra’s growth and expand our public-sector reach.\n\n - Build and lead joint go-to-market strategies with key partners, developing compelling joint value propositions, identifying priority accounts and use cases, and aligning sales motions, pipeline goals, and shared success metrics to drive measurable commercial outcomes.\n\n - Build a scalable partner program and enablement engine from the ground up, including training, certification paths, sales plays, field-facing materials, commercial frameworks, and onboarding programs that give partners the tools and confidence to effectively position, sell, and deliver Sierra.\n\n - Own and grow strategic partner relationships from initial engagement through long-term success, cultivating executive-level sponsorship while establishing the operating rhythms, joint planning, business reviews, governance, and scorecards needed to keep partnerships accountable, productive, and scaling over time.\n\n - Serve as the connective tissue between Sierra and the broader public-sector partner ecosystem, partnering closely with Sales, Marketing, Product, and Legal; bringing market intelligence and partner feedback back into Sierra; representing the company at key industry and procurement events; and using pipeline and performance data to determine where to invest, course-correct, or evolve our partnership strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10+ years of experience in strategic partnerships, alliances, or channel strategy, with significant experience across US, Canada, and/or UK Government and SLED markets and a proven track record of building and scaling partner programs that drive engagement and pipeline.\n\n - Strong relationships across the government technology ecosystem, including resellers, systems integrators, distributors, and strategic partners such as Carahsoft, Deloitte, Accenture Federal Services, or comparable public-sector organizations.\n\n - Deep understanding of government procurement and public-sector requirements, including RFPs/RFIs, cooperative purchasing vehicles, GSA schedules, CCS/G-Cloud frameworks, Canadian procurement vehicles, and relevant compliance, security, and accessibility requirements.\n\n - Strong executive presence and relationship-building skills, with a demonstrated ability to earn senior-level trust and sponsorship while developing GTM frameworks, enablement programs, and operating cadences that scale partnerships.\n\n - AI fluency and a builder mindset, with experience leveraging AI-powered tools and insights in day-to-day work and applying that knowledge to partnerships around an AI-native product like Sierra, along with the ability to travel across the US, Canada, and UK as needed.\n\n\nEVEN BETTER...\n\n - Experience working at or partnering closely with government-focused organizations such as Carahsoft, Deloitte, or Accenture Federal, ideally within a high-growth enterprise company where you helped build and scale a public-sector partner ecosystem.\n\n - Experience structuring and growing strategic partnerships, including negotiating commercial terms, developing co-sell and governance frameworks, and driving joint GTM initiatives, customer events, executive engagement, and partner marketing programs.\n\n - Knowledge of the government technology landscape, ideally including CX/customer service technology, AI/ML applications and public-sector AI policy/procurement trends, with an existing security clearance or eligibility to obtain one where applicable.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"931cbf48-7e8a-485a-a45b-7e08adc62962","title":"Enterprise Sales Engineer, Public Sector","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"US - Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}},{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-14T16:36:59.053+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/931cbf48-7e8a-485a-a45b-7e08adc62962","applyUrl":"https://jobs.ashbyhq.com/sierra/931cbf48-7e8a-485a-a45b-7e08adc62962/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
GTM technical expert: Own the end-to-end technical pre-sales process for government institutions at the Federal and state level by scopong customer use cases, articulating business value. designing and demoing Sierra's incredible platform, leading technical and architecture reviews, and serving as a trusted technical expert throughout the sales cycle.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer -driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
Partner closely with industry leadership to build our public sector team, including our capture motion, market strategy, and product components to scale quickly.
5-7+ years experience, in Sales Engineering, Solutions Engineering, or customer facing technical sales, including 2+ years supporting U.S federal, state, or local government customers.
Past Experience in demo building, and presenting, and working iwth customers or clienrs in the GTM function.
Experience in relationship-building with potential customers, including exectuvies and techncial leaders.
Experience in leading the sales process with public sector customers; familairtiy with FedRAMP and government authorization processes.
Comfort and prior experience operating as an early or founding member of a new team or business
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Experience treanslating coadde, tehcnical logic and user requiremenrts to product and engineering requirements
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU'LL DO\n\n\n\n\n - GTM technical expert: Own the end-to-end technical pre-sales process for government institutions at the Federal and state level by scopong customer use cases, articulating business value. designing and demoing Sierra's incredible platform, leading technical and architecture reviews, and serving as a trusted technical expert throughout the sales cycle. \n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer -driven product development philosophy. \n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n - Partner closely with industry leadership to build our public sector team, including our capture motion, market strategy, and product components to scale quickly.\n\n\nWHAT YOU'LL BRING\n\n\n\n\n - 5-7+ years experience, in Sales Engineering, Solutions Engineering, or customer facing technical sales, including 2+ years supporting U.S federal, state, or local government customers. \n\n - Past Experience in demo building, and presenting, and working iwth customers or clienrs in the GTM function. \n\n - Experience in relationship-building with potential customers, including exectuvies and techncial leaders. \n\n - Experience in leading the sales process with public sector customers; familairtiy with FedRAMP and government authorization processes. \n\n - Comfort and prior experience operating as an early or founding member of a new team or business\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. With that, you know where these tools can help and where human judgment still is required. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it. This ownership looks like us not saying \"[AI tool of choice] built this\", but \"I built this with [AI tool of choice].\"\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nEVEN BETTER...\n\n - Experience treanslating coadde, tehcnical logic and user requiremenrts to product and engineering requirements \n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"4572d713-6df1-432a-9cce-67bdbbabf43b","title":"Strategist, Agent Development (Brazilian Portuguese speaking)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-17T13:19:25.285+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/4572d713-6df1-432a-9cce-67bdbbabf43b","applyUrl":"https://jobs.ashbyhq.com/sierra/4572d713-6df1-432a-9cce-67bdbbabf43b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"3f6911c0-b49b-4d8e-a434-4064df2cde44","title":"Web Developer, Marketing Site","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-16T21:15:34.318+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/3f6911c0-b49b-4d8e-a434-4064df2cde44","applyUrl":"https://jobs.ashbyhq.com/sierra/3f6911c0-b49b-4d8e-a434-4064df2cde44/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own frontend across product and marketing surfaces: You will work across both our core product interface and customer-facing web pages, ensuring a cohesive, polished user experience across all touch points. This includes building features in the web app and also collaborating on our website to keep branding and user experience consistent and high-quality.
Build content infrastructure that unblocks the team: You'll develop our CMS (we use Sanity) to give content and marketing teams self-serve tooling, structured content models, and preview/staging workflows, so routine changes don't depend on engineering. You'll design content schemas and editing experiences that let non-engineers move quickly and confidently.
Champion growth: You'll partner with marketing, sales, and operations to implement analytics and enable experimentation, turning business goals into shipped, instrumented features so we always know what's actually working.
Make localization first-class: You'll support localization and internationalization — multilingual content, translation workflows, and the infrastructure behind them, so non-English experiences are genuinely first-class rather than afterthoughts.
Treat performance as a feature: You'll own Core Web Vitals, media and asset optimization, and the diagnosis of the subtle issues: layout shift, lazy-loading, video quality, render timing. You care about speed, and you measure it.
Hold a high bar for accessibility: You'll champion semantic markup, keyboard navigation, screen-reader support, and WCAG-minded component design, ensuring the site is usable by everyone who visits it.
Marketing and growth fluency: You've worked on marketing or growth-facing web before, and you understand the business context — funnels, conversion, SEO, analytics, and A/B testing—not just the code. We care about this more than years of experience or exact seniority.
Strong frontend fundamentals: You're fluent in modern JavaScript and TypeScript and React (or a similar framework), with a real sense for UI/UX craft and an instinct for getting the small details right.
A genuine commitment to performance and accessibility: You care about both deeply and can point to specific, concrete things you've done to improve them in production.
Comfort with structured content: You've worked with a headless CMS and structured content models before. Sanity experience is a plus.
Strong cross-functional collaboration: You work well with non-engineers — designers, content writers, and marketers — and can translate their goals into technical work, and technical tradeoffs back into terms they can act on.
Even better...
Localization and i18n experience: You've worked with internationalization systems and translation tooling before.
Analytics and experimentation depth: You're familiar with web analytics and experimentation platforms and know how to use them to drive decisions.
Third-party integration experience: You've integrated services like video hosting or error monitoring into a content workflow.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Own frontend across product and marketing surfaces: You will work across both our core product interface and customer-facing web pages, ensuring a cohesive, polished user experience across all touch points. This includes building features in the web app and also collaborating on our website to keep branding and user experience consistent and high-quality.\n\n - Build content infrastructure that unblocks the team: You'll develop our CMS (we use Sanity) to give content and marketing teams self-serve tooling, structured content models, and preview/staging workflows, so routine changes don't depend on engineering. You'll design content schemas and editing experiences that let non-engineers move quickly and confidently.\n\n - Champion growth: You'll partner with marketing, sales, and operations to implement analytics and enable experimentation, turning business goals into shipped, instrumented features so we always know what's actually working.\n\n - Make localization first-class: You'll support localization and internationalization — multilingual content, translation workflows, and the infrastructure behind them, so non-English experiences are genuinely first-class rather than afterthoughts.\n\n - Treat performance as a feature: You'll own Core Web Vitals, media and asset optimization, and the diagnosis of the subtle issues: layout shift, lazy-loading, video quality, render timing. You care about speed, and you measure it.\n\n - Hold a high bar for accessibility: You'll champion semantic markup, keyboard navigation, screen-reader support, and WCAG-minded component design, ensuring the site is usable by everyone who visits it.\n\n\nWHAT YOU'LL BRING\n\n - Marketing and growth fluency: You've worked on marketing or growth-facing web before, and you understand the business context — funnels, conversion, SEO, analytics, and A/B testing—not just the code. We care about this more than years of experience or exact seniority.\n\n - Strong frontend fundamentals: You're fluent in modern JavaScript and TypeScript and React (or a similar framework), with a real sense for UI/UX craft and an instinct for getting the small details right.\n\n - A genuine commitment to performance and accessibility: You care about both deeply and can point to specific, concrete things you've done to improve them in production.\n\n - Comfort with structured content: You've worked with a headless CMS and structured content models before. Sanity experience is a plus.\n\n - Strong cross-functional collaboration: You work well with non-engineers — designers, content writers, and marketers — and can translate their goals into technical work, and technical tradeoffs back into terms they can act on.\n\nEven better...\n\n - Localization and i18n experience: You've worked with internationalization systems and translation tooling before.\n\n - Analytics and experimentation depth: You're familiar with web analytics and experimentation platforms and know how to use them to drive decisions.\n\n - Third-party integration experience: You've integrated services like video hosting or error monitoring into a content workflow.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"15f81581-ad9c-4b03-8ed7-097fbbce0469","title":"Strategist, Agent Development - Flagship Deployment","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-18T19:34:02.051+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/15f81581-ad9c-4b03-8ed7-097fbbce0469","applyUrl":"https://jobs.ashbyhq.com/sierra/15f81581-ad9c-4b03-8ed7-097fbbce0469/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As an Agent Strategist on a Flagship Deployment, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You own how Sierra's AI agents come to life, often managing scaled deployments as well as new proofs of concept within the same account. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer's working teams and executives day to day. Oversee overall program management while ensuring ongoing executive alignment on the long term roadmap.
Navigate enterprise complexity with cross-functional teams (engineering and product). At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
Manage internal resourcing requirements. Ensure that your deployment is appropriately resourced today and into the future
Drive financial success for both the customer and Sierra. Ensure value exchange is optimized, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins.
Partner with Sales on commercial strategy. You are a key player in closing new business within the deployment by identifying opportunities, aligning resources, and
These are the kinds of projects that strategists on our team have worked on recently:
Plan, organize, and execute on-site business reviews onsite at a Fortune 100 company with Sierra cofounders in attendance
Manage a portfolio of agents across a customer deployment as they scale nationally, to new use cases, and grow in technical complexity
Build relationships throughout the customer’s organization, unlocking high trust, social capital, and ultimately new ARR
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Proven track record: 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise account — you know what it means to be accountable for a relationship at that depth.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
You've run a company, business unit, forward deployed team, or have comparable experience in general management of business initiatives that require technical aptitude, strategic leadership, operational excellence, and financial outcome accountability.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai on a Flagship Deployment, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You own how Sierra's AI agents come to life, often managing scaled deployments as well as new proofs of concept within the same account. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer's working teams and executives day to day. Oversee overall program management while ensuring ongoing executive alignment on the long term roadmap.\n\n - Navigate enterprise complexity with cross-functional teams (engineering and product). At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n - Manage internal resourcing requirements. Ensure that your deployment is appropriately resourced today and into the future\n\n - Drive financial success for both the customer and Sierra. Ensure value exchange is optimized, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins.\n\n - Partner with Sales on commercial strategy. You are a key player in closing new business within the deployment by identifying opportunities, aligning resources, and\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Plan, organize, and execute on-site business reviews onsite at a Fortune 100 company with Sierra cofounders in attendance\n\n - Manage a portfolio of agents across a customer deployment as they scale nationally, to new use cases, and grow in technical complexity\n\n - Build relationships throughout the customer’s organization, unlocking high trust, social capital, and ultimately new ARR\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Proven track record: 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise account — you know what it means to be accountable for a relationship at that depth.\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - You've run a company, business unit, forward deployed team, or have comparable experience in general management of business initiatives that require technical aptitude, strategic leadership, operational excellence, and financial outcome accountability.\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"de46bdfc-6417-4682-9ef1-a3ead059d369","title":"GTM Operations, Business Value","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-21T23:06:41.572+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/de46bdfc-6417-4682-9ef1-a3ead059d369","applyUrl":"https://jobs.ashbyhq.com/sierra/de46bdfc-6417-4682-9ef1-a3ead059d369/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We're looking for a business value strategist to join our pricing team. You'll partner with sales and customers throughout complex enterprise sales cycles to develop customer-specific value frameworks, build rigorous ROI models and investment cases grounded in operating and financial metrics, and translate Sierra's impact into measurable outcomes such as lower operating costs, incremental revenue, and stronger customer loyalty. You'll also create and scale repeatable, industry-specific business cases and establish Sierra's business value framework from the ground up.
This is a hands-on role for someone who can bring structure to ambiguous problems, develop rigorous analysis, and has strong communciation.
Support complex enterprise sales cycles by developing ROI models, evaluating tradeoffs, and presenting recommendations to senior decision-makers
Shape commercial strategy by connecting the value Sierra delivers to our outcomes-based pricing model
Develop industry-specific benchmarks, frameworks, and tools that make Sierra’s business value clear and repeatable
5+ years of experience in value engineering, monetization strategy, consulting, strategic finance, or a similar role focused on quantifying and communicating business impact
Advanced financial modeling and analytical skills, with a track record of building rigorous ROI models and investment cases
Experience supporting complex enterprise sales cycles and engaging senior decision-makers
Ability to partner effectively with sales teams and customer stakeholders across finance, operations, and executive leadership
Degree in Business Administration, Finance, Economics, or a related field, or equivalent professional experience
Experience building and scaling a business value methodology, program, or center of excellence from the ground up
Familiarity with AI, conversational AI, or customer service operations
Previous experience in a zero-to-one startup or fast-paced, high-growth environment
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\nWe're looking for a business value strategist to join our pricing team. You'll partner with sales and customers throughout complex enterprise sales cycles to develop customer-specific value frameworks, build rigorous ROI models and investment cases grounded in operating and financial metrics, and translate Sierra's impact into measurable outcomes such as lower operating costs, incremental revenue, and stronger customer loyalty. You'll also create and scale repeatable, industry-specific business cases and establish Sierra's business value framework from the ground up.\n\nThis is a hands-on role for someone who can bring structure to ambiguous problems, develop rigorous analysis, and has strong communciation.\n\n - Support complex enterprise sales cycles by developing ROI models, evaluating tradeoffs, and presenting recommendations to senior decision-makers\n\n - Shape commercial strategy by connecting the value Sierra delivers to our outcomes-based pricing model\n\n - Develop industry-specific benchmarks, frameworks, and tools that make Sierra’s business value clear and repeatable\n\n\nWHAT YOU'LL BRING\n\n - 5+ years of experience in value engineering, monetization strategy, consulting, strategic finance, or a similar role focused on quantifying and communicating business impact\n\n - Advanced financial modeling and analytical skills, with a track record of building rigorous ROI models and investment cases\n\n - Experience supporting complex enterprise sales cycles and engaging senior decision-makers\n\n - Ability to partner effectively with sales teams and customer stakeholders across finance, operations, and executive leadership\n\n - Degree in Business Administration, Finance, Economics, or a related field, or equivalent professional experience\n\n\nEVEN BETTER...\n\n - Experience building and scaling a business value methodology, program, or center of excellence from the ground up\n\n - Familiarity with AI, conversational AI, or customer service operations\n\n - Previous experience in a zero-to-one startup or fast-paced, high-growth environment\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"01988f90-2d70-48ee-9c01-92e69c37706b","title":"Strategist, Agent Development - Retail","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-23T14:23:26.077+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/01988f90-2d70-48ee-9c01-92e69c37706b","applyUrl":"https://jobs.ashbyhq.com/sierra/01988f90-2d70-48ee-9c01-92e69c37706b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.
Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.
Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Launch an order management agent for a national apparel brand — order lookup, cancellations, returns, and exchanges — then hill-climb containment and CSAT week over week.
Partner with Product to build a shopping agent that plugs into a retailer’s existing search and recommendation systems to guide product discovery — turning the support channel into a revenue channel.
Stand up an in-store support voice agent for a big-box or grocery retailer, answering the stock-check and store-info calls that largely go unanswered today and converting them into store visits and sales.
Design a booking, payments, and outbound agent for a consumer services brand operating hundreds of locations.
Help a marketplace handle order status and buyer–seller disputes at enormous scale.
Launch outbound campaigns — cart recovery, win-back, churn saves, and subscription renewals — across voice and SMS.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Interest in retail and consumer experiences. Experience in e-commerce, retail technology, marketplaces, or consumer brands — and familiarity with commerce and CX stacks (e.g., commerce platforms, order management systems, contact center software) — is a strong plus.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice.\n\n - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line.\n\n - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Launch an order management agent for a national apparel brand — order lookup, cancellations, returns, and exchanges — then hill-climb containment and CSAT week over week.\n\n - Partner with Product to build a shopping agent that plugs into a retailer’s existing search and recommendation systems to guide product discovery — turning the support channel into a revenue channel.\n\n - Stand up an in-store support voice agent for a big-box or grocery retailer, answering the stock-check and store-info calls that largely go unanswered today and converting them into store visits and sales.\n\n - Design a booking, payments, and outbound agent for a consumer services brand operating hundreds of locations.\n\n - Help a marketplace handle order status and buyer–seller disputes at enormous scale.\n\n - Launch outbound campaigns — cart recovery, win-back, churn saves, and subscription renewals — across voice and SMS.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n - Interest in retail and consumer experiences. Experience in e-commerce, retail technology, marketplaces, or consumer brands — and familiarity with commerce and CX stacks (e.g., commerce platforms, order management systems, contact center software) — is a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"33dbd62f-8212-4ea8-9b59-74370c1f2803","title":"Software Engineer, Agent - Financial Services","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-09-23T17:05:41.540+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/33dbd62f-8212-4ea8-9b59-74370c1f2803","applyUrl":"https://jobs.ashbyhq.com/sierra/33dbd62f-8212-4ea8-9b59-74370c1f2803/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1e40515a-c2d9-4657-8a44-a99d6d49b15b","title":"Strategist, Agent Development - Travel, Transportation and Hospitality","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-10-01T15:39:57.968+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1e40515a-c2d9-4657-8a44-a99d6d49b15b","applyUrl":"https://jobs.ashbyhq.com/sierra/1e40515a-c2d9-4657-8a44-a99d6d49b15b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are pioneers in the travel space and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us not only to deliver exceptional customer experiences, but also to drive meaningful growth for their businesses.
Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint.
We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard for what it means to go beyond your role, and help build the travel industry of the future.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE TRAVEL, TRANSPORTATION AND HOSPITALITY TEAM\n\n - The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are pioneers in the travel space and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us not only to deliver exceptional customer experiences, but also to drive meaningful growth for their businesses.\n\n - Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint.\n\n - We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard for what it means to go beyond your role, and help build the travel industry of the future.\n\n\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7dae2e7c-6556-438c-bf60-509931d8188c","title":"Software Engineer, Agent - Public Sector","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-23T17:06:01.317+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7dae2e7c-6556-438c-bf60-509931d8188c","applyUrl":"https://jobs.ashbyhq.com/sierra/7dae2e7c-6556-438c-bf60-509931d8188c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Design and build production-grade AI agents for government institutions at the Federal and state level.
Partner closely with industry leadership to build our public sector team, including our capture motion, market strategy, and product components to scale quickly.
Work closely with institutions to understand their most urgent needs and identify novel opportunities to expand our impact - for example through outbound contacts or long-horizon agents.
Build the future of the platform: Your direct work with public sector customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development.
Full stack software development skills and familiarity with AI development processes.
A passion for public sector work and a faith in the potential of our institutions to transform outcomes for their constituents.
Comfort working directly with customers to understand their needs and solve real-world problems. A core part of the role is coordinating directly with public servants at our partners to understand their workflows.
Experience building conversational or long-horizon agents using proprietary or open source frameworks.
Demonstrated track record ambiguity, for example as part of a founding team, new initiative at a large enterprise, forward deployed engineering, or elsewhere.
A prior understanding of government work and its complexities, including procurement, regulation, and patterns of partnership.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU’LL DO\n\n - Design and build production-grade AI agents for government institutions at the Federal and state level.\n\n - Partner closely with industry leadership to build our public sector team, including our capture motion, market strategy, and product components to scale quickly.\n\n - Work closely with institutions to understand their most urgent needs and identify novel opportunities to expand our impact - for example through outbound contacts or long-horizon agents.\n\n - Build the future of the platform: Your direct work with public sector customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development.\n\n\nWHAT YOU'LL BRING\n\n - Full stack software development skills and familiarity with AI development processes.\n\n - A passion for public sector work and a faith in the potential of our institutions to transform outcomes for their constituents.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems. A core part of the role is coordinating directly with public servants at our partners to understand their workflows.\n\n\nEVEN BETTER…\n\n - Experience building conversational or long-horizon agents using proprietary or open source frameworks.\n\n - Demonstrated track record ambiguity, for example as part of a founding team, new initiative at a large enterprise, forward deployed engineering, or elsewhere.\n\n - A prior understanding of government work and its complexities, including procurement, regulation, and patterns of partnership.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"c729c633-0376-436e-8f2b-1501088b85b0","title":"Software Engineer, Agent - Retail","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}},{"location":"Toronto","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-09-23T17:06:32.307+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/c729c633-0376-436e-8f2b-1501088b85b0","applyUrl":"https://jobs.ashbyhq.com/sierra/c729c633-0376-436e-8f2b-1501088b85b0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
The Retail team on Agent Engineering supports some of the largest and most storied consumer brands in the world – including Gap, Wayfair, Sonos, and ADT. Together, we’re reinventing what commerce looks like in this new, AI-first era. Our customers rely on us to not only deliver novel experiences, but also host hundreds of millions of shopper and vendor interactions across web, app, phone, and in-store channels every year.
Our team supports our customers’ customers in the moments that matter – whether that's guiding a shopper to the right product during a limited drop or a Black Friday surge, locating a package that never arrived, or troubleshooting an appliance that stopped working. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.
Our team supports our customers' customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.
Every engineer on the Retail Team is a product-led thinker; every PM on Retail is also tinkering and developing tangible prototypes; and every strategist on Retail is capable of owning an agent end to end. As a part of this team, you'll set the standard on what it means to go beyond your role, and help build the groundwork for the retail industry in the future.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Abstracting complex commerce systems into packages: Modernize the sprawl of order management, fulfillment, returns, and warranty systems behind the large retailer ecosystem by creating scalable packages that optimize looking up and updating orders for customers – from Shopify storefronts to decades-old homegrown Order Management System (OMS) and claims platforms.
Shipping the full discovery-to-checkout lifecycle: Build personalized shopping flows that carry a shopper from a vague idea to a completed order. This includes everything from building a recommendation engine that combines transcript-aware planning, structured filters, and semantic and keyword search to payment and order placement.
Building production-grade agents at a truly global scale: Sierra’s retail agents serve some of the world’s largest global brands, handling traffic at unprecedented volumes during the busiest times of the year and across all geographic locales. You will be building at the frontier of enterprise applied AI.
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Excitement in the retail space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE RETAIL TEAM\n\n - The Retail team on Agent Engineering supports some of the largest and most storied consumer brands in the world – including Gap, Wayfair, Sonos, and ADT. Together, we’re reinventing what commerce looks like in this new, AI-first era. Our customers rely on us to not only deliver novel experiences, but also host hundreds of millions of shopper and vendor interactions across web, app, phone, and in-store channels every year.\n\n - Our team supports our customers’ customers in the moments that matter – whether that's guiding a shopper to the right product during a limited drop or a Black Friday surge, locating a package that never arrived, or troubleshooting an appliance that stopped working. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.\n\n - Our team supports our customers' customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty.\n\n - Every engineer on the Retail Team is a product-led thinker; every PM on Retail is also tinkering and developing tangible prototypes; and every strategist on Retail is capable of owning an agent end to end. As a part of this team, you'll set the standard on what it means to go beyond your role, and help build the groundwork for the retail industry in the future.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Abstracting complex commerce systems into packages: Modernize the sprawl of order management, fulfillment, returns, and warranty systems behind the large retailer ecosystem by creating scalable packages that optimize looking up and updating orders for customers – from Shopify storefronts to decades-old homegrown Order Management System (OMS) and claims platforms.\n\n - Shipping the full discovery-to-checkout lifecycle: Build personalized shopping flows that carry a shopper from a vague idea to a completed order. This includes everything from building a recommendation engine that combines transcript-aware planning, structured filters, and semantic and keyword search to payment and order placement.\n\n - Building production-grade agents at a truly global scale: Sierra’s retail agents serve some of the world’s largest global brands, handling traffic at unprecedented volumes during the busiest times of the year and across all geographic locales. You will be building at the frontier of enterprise applied AI.\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Excitement in the retail space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d0055259-9801-4767-b659-39e967a88b50","title":"Strategist, Agent Development - Financial Services","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-23T14:23:08.161+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d0055259-9801-4767-b659-39e967a88b50","applyUrl":"https://jobs.ashbyhq.com/sierra/d0055259-9801-4767-b659-39e967a88b50/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"d2dc9baf-30d4-4708-9227-62a946b4b37e","title":"Software Engineer, Agent - Travel & Hospitality","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-09-23T17:08:27.771+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/d2dc9baf-30d4-4708-9227-62a946b4b37e","applyUrl":"https://jobs.ashbyhq.com/sierra/d2dc9baf-30d4-4708-9227-62a946b4b37e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are frontiers in the travel space, and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us to not only deliver standout customer experiences, driving stronger growth in their business.
Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint.
We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard on what it means to go beyond your role, and help build the travel industry of the future.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Building innovative multimodal experiences: Spearhead cross-cutting initiatives, partnering with the voice and Experience SDK teams to bring to life embedded voice mode in mobile apps. This brand new product allows users to talk, tap and text with our agents all in a single view — unlocking communication through rich visualizations, and accuracy in input collection with chat, with the ease and efficiency of voice.
Shipping complex booking experiences: Build personalized booking flows, including leveraging Google Maps APIs to support searching for properties via an embedded map view, developing a recommendation engine based on past reservations and orchestrating seamless payment collection to complete the full booking lifecycle.
Abstracting complex systems into packages: Modernize legacy reservations systems by creating Sierra packages that optimize querying and updating trips for customers across the board. You’ll be challenged to think deeply about how to orchestrate each step of these workflows to maximize efficiency while upholding reliability and accuracy.
Improving the capabilities of our built in integrations: Expand platform extensibility by introducing new capabilities to our existing integrations. An example is extending our MCP integrations to support MCP UI, which allows customers to dynamically host their custom UI resources on our embedded chat windows.
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Excitement in the travel space and a genuine care for helping improve the guest experience as a whole. Our customers care deeply about their guests, and we carry that through what we build every day.
Language Fluency: Professional fluency in both Spanish and English.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE TRAVEL, TRANSPORTATION AND HOSPITALITY TEAM\n\n - The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are frontiers in the travel space, and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us to not only deliver standout customer experiences, driving stronger growth in their business. \n\n - Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint.\n\n - We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard on what it means to go beyond your role, and help build the travel industry of the future.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Building innovative multimodal experiences: Spearhead cross-cutting initiatives, partnering with the voice and Experience SDK teams to bring to life embedded voice mode in mobile apps. This brand new product allows users to talk, tap and text with our agents all in a single view — unlocking communication through rich visualizations, and accuracy in input collection with chat, with the ease and efficiency of voice.\n\n - Shipping complex booking experiences: Build personalized booking flows, including leveraging Google Maps APIs to support searching for properties via an embedded map view, developing a recommendation engine based on past reservations and orchestrating seamless payment collection to complete the full booking lifecycle.\n\n - Abstracting complex systems into packages: Modernize legacy reservations systems by creating Sierra packages that optimize querying and updating trips for customers across the board. You’ll be challenged to think deeply about how to orchestrate each step of these workflows to maximize efficiency while upholding reliability and accuracy.\n\n - Improving the capabilities of our built in integrations: Expand platform extensibility by introducing new capabilities to our existing integrations. An example is extending our MCP integrations to support MCP UI, which allows customers to dynamically host their custom UI resources on our embedded chat windows.\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Excitement in the travel space and a genuine care for helping improve the guest experience as a whole. Our customers care deeply about their guests, and we carry that through what we build every day.\n\n\nEVEN BETTER...\n\n - Language Fluency: Professional fluency in both Spanish and English.\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"a2e49318-5967-4509-a592-56f089647b32","title":"Strategist, Agent Development - Healthcare","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-23T14:22:43.481+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/a2e49318-5967-4509-a592-56f089647b32","applyUrl":"https://jobs.ashbyhq.com/sierra/a2e49318-5967-4509-a592-56f089647b32/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.
Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.
Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are examples of projects our healthcare team has worked on:
Lead the project for building AI agents for major health insurance networks that handle detailed questions like “what’s my co-pay for a primary care visit?” and “how many physical therapy sessions do I have left?”
Ideate and create a roadmap for growing value for large healthcare payers and providers.
Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics.
Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates.
Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Genuine interest in healthcare and improving patient/member experiences. Experience in healthcare technology, health IT or working with healthcare organizations and an understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) are a strong plus.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE HEALTHCARE TEAM\n\n - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system.\n\n - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms.\n\n - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are examples of projects our healthcare team has worked on:\n\n - Lead the project for building AI agents for major health insurance networks that handle detailed questions like “what’s my co-pay for a primary care visit?” and “how many physical therapy sessions do I have left?”\n\n - Ideate and create a roadmap for growing value for large healthcare payers and providers.\n\n - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics.\n\n - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates.\n\n - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n - Genuine interest in healthcare and improving patient/member experiences. Experience in healthcare technology, health IT or working with healthcare organizations and an understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) are a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"078f8499-1099-4675-b3df-47cf201e7427","title":"Strategist, Agent Development - Public Sector","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-23T14:23:53.701+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/078f8499-1099-4675-b3df-47cf201e7427","applyUrl":"https://jobs.ashbyhq.com/sierra/078f8499-1099-4675-b3df-47cf201e7427/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. Translate mission goals, policy requirements, and operational workflows into an agent that performs reliably in the real world.
Be a trusted strategic advisor to public sector leaders. Work shoulder-to-shoulder with agency executives and program leaders to define success, prioritize opportunities, and shape an AI strategy grounded in mission impact.
Partner with working teams day to day. Run working sessions with program, operations, technology, security, legal, and procurement stakeholders; resolve issues as they arise; and make the decisions that keep deployments moving toward launch.
Identify new ways to expand our impact. Understand our partners' most urgent needs and develop roadmaps for new use cases, including proactive outreach, multilingual access, and long-horizon agents that can support people across multi-step journeys.
Directly shape the product and our public sector strategy. Surface unmet needs from customer work, prototype new approaches, and partner with research, product, platform, and public sector leadership to influence Sierra's roadmap, market strategy, and repeatable solutions for government.
These are the kinds of projects that strategists on our public sector team have worked on recently:
Improve access to benefits and services. Launch an agent that helps residents understand eligibility, gather the right information, and navigate a complex application or recertification process across channels and languages.
Modernize constituent support. Design an agent that answers policy and program questions, provides case or application status, and routes sensitive or exceptional situations to the right public servant with full context.
Make critical reporting easier and safer. Build trusted conversational experiences for reporting fraud, safety concerns, or other high-stakes issues while meeting rigorous privacy, security, accessibility, and auditability requirements.
Enable proactive government services. Create a roadmap for outbound agents that remind people about deadlines, explain program changes, or help them complete important next steps before a benefit or service is interrupted.
Build repeatable public sector capabilities. Use a live agency deployment as a design partnership to shape new platform capabilities, evaluation standards, or implementation patterns that can serve institutions across federal, state, and local government.
Ownership and delivery. A track record of leading multiple complex, high-visibility initiatives and driving cross-functional teams from an ambiguous starting point to measurable outcomes - for example as part of an early team, consultancy, or otherwise..
Technical aptitude. Comfort engaging directly with technical concepts, including reading API documentation, understanding data models and system architecture, and following engineering and security tradeoffs in design discussions.
Commitment to public service. A passion for public sector work and a belief in the potential of institutions to improve outcomes for the people and communities they serve.
Communication. Clear, direct, and persuasive communication across executive, operational, policy, and technical audiences, with the ability to turn complexity into shared decisions.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as policy, stakeholder, or implementation conditions change.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
Experience working in or with federal, state, or local government, including familiarity with procurement, security and compliance, accessibility, policy implementation, or systems integration.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. Translate mission goals, policy requirements, and operational workflows into an agent that performs reliably in the real world.\n\n - Be a trusted strategic advisor to public sector leaders. Work shoulder-to-shoulder with agency executives and program leaders to define success, prioritize opportunities, and shape an AI strategy grounded in mission impact.\n\n - Partner with working teams day to day. Run working sessions with program, operations, technology, security, legal, and procurement stakeholders; resolve issues as they arise; and make the decisions that keep deployments moving toward launch.\n\n - Identify new ways to expand our impact. Understand our partners' most urgent needs and develop roadmaps for new use cases, including proactive outreach, multilingual access, and long-horizon agents that can support people across multi-step journeys.\n\n - Directly shape the product and our public sector strategy. Surface unmet needs from customer work, prototype new approaches, and partner with research, product, platform, and public sector leadership to influence Sierra's roadmap, market strategy, and repeatable solutions for government.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our public sector team have worked on recently:\n\n - Improve access to benefits and services. Launch an agent that helps residents understand eligibility, gather the right information, and navigate a complex application or recertification process across channels and languages.\n\n - Modernize constituent support. Design an agent that answers policy and program questions, provides case or application status, and routes sensitive or exceptional situations to the right public servant with full context.\n\n - Make critical reporting easier and safer. Build trusted conversational experiences for reporting fraud, safety concerns, or other high-stakes issues while meeting rigorous privacy, security, accessibility, and auditability requirements.\n\n - Enable proactive government services. Create a roadmap for outbound agents that remind people about deadlines, explain program changes, or help them complete important next steps before a benefit or service is interrupted.\n\n - Build repeatable public sector capabilities. Use a live agency deployment as a design partnership to shape new platform capabilities, evaluation standards, or implementation patterns that can serve institutions across federal, state, and local government.\n\n\nWHAT YOU’LL BRING\n\n - Ownership and delivery. A track record of leading multiple complex, high-visibility initiatives and driving cross-functional teams from an ambiguous starting point to measurable outcomes - for example as part of an early team, consultancy, or otherwise..\n\n - Technical aptitude. Comfort engaging directly with technical concepts, including reading API documentation, understanding data models and system architecture, and following engineering and security tradeoffs in design discussions.\n\n - Commitment to public service. A passion for public sector work and a belief in the potential of institutions to improve outcomes for the people and communities they serve.\n\n - Communication. Clear, direct, and persuasive communication across executive, operational, policy, and technical audiences, with the ability to turn complexity into shared decisions.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as policy, stakeholder, or implementation conditions change.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - Experience working in or with federal, state, or local government, including familiarity with procurement, security and compliance, accessibility, policy implementation, or systems integration.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b9b9b5e0-7304-4265-aa71-d71d80d29402","title":"Software Engineer, Agent - Insurance","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Atlanta, GA","address":{"postalAddress":{"addressRegion":"GA","addressCountry":"United States","addressLocality":"Atlanta"}}}],"publishedAt":"2026-09-23T17:07:19.284+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b9b9b5e0-7304-4265-aa71-d71d80d29402","applyUrl":"https://jobs.ashbyhq.com/sierra/b9b9b5e0-7304-4265-aa71-d71d80d29402/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Our financial services customers span insurers that provide protection for life’s most challenging moments, systemically important banks, neobanks committed to building more delightful banking software, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.
Our Financial Services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle—the hours after a family discovers their home has been damaged by a wildfire and begins filing a claim; the difficult conversation following the loss of a loved one as beneficiaries navigate a life insurance claim; the frustration of dropping a phone, shattering the screen, and trying to quickly understand coverage and arrange for a repair or replacement.
Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large insurance companies that consistently outperform human agents in filing claims quickly and consistently.
Develop and refine AI agents capable of navigating complex customer interactions, like generating a quote for insuring a modified 1960s Corvette.
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Genuine interest in Financial Services and improving the end customer experience. Experience in insurance technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.) are a strong plus.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE FINANCIAL SERVICES TEAM\n\n - Our financial services customers span insurers that provide protection for life’s most challenging moments, systemically important banks, neobanks committed to building more delightful banking software, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity.\n\n - Our Financial Services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle—the hours after a family discovers their home has been damaged by a wildfire and begins filing a claim; the difficult conversation following the loss of a loved one as beneficiaries navigate a life insurance claim; the frustration of dropping a phone, shattering the screen, and trying to quickly understand coverage and arrange for a repair or replacement.\n\n - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large insurance companies that consistently outperform human agents in filing claims quickly and consistently.\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like generating a quote for insuring a modified 1960s Corvette.\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Genuine interest in Financial Services and improving the end customer experience. Experience in insurance technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.) are a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"2c5928df-28ec-468f-99f3-42b7e73cbf93","title":"Strategist, Agent Development - Tech, Media & Telecom","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-23T14:23:39.239+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/2c5928df-28ec-468f-99f3-42b7e73cbf93","applyUrl":"https://jobs.ashbyhq.com/sierra/2c5928df-28ec-468f-99f3-42b7e73cbf93/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide.
We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup drive millions of customer interactions.
We bring Sierra’s Horizon vision to TMT by building agents that transform the entire customer relationship:
Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time.
Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention.
Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects strategists on our TMT team work on:
Scope and launch a subscription-retention agent for a telecommunications or media company, then tune it to save more at-risk customers while preserving trust and brand voice.
Launch a top-of-funnel sales agent for a telecommunications provider that qualifies prospects, recommends plans and devices, and converts interest into new subscriptions.
Build a new-subscriber onboarding agent that activates service, ports numbers, configures devices, and reduces early-life churn.
Create a proactive, long-running agent that detects service or account issues, reaches out across channels, and manages resolution before the customer contacts support.
Develop a media growth agent that drives content discovery, trial conversion, plan upgrades, and subscription renewal.
Partner with Product to develop capabilities for TMT-scale traffic, including low-latency voice, multilingual experiences, proactive communications, and resilient performance during major launches or service events.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts — reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Interest in telecommunications, media, and technology. Experience in telecom, streaming and digital media, enterprise or consumer technology, or subscription businesses — and familiarity with customer care, billing, identity, content, or technical support systems — is a strong plus.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.
Client-facing consulting, solutions, or strategy experience in a technically complex environment.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE TECH, MEDIA & TELECOM TEAM\n\n - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide.\n\n - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-share-7491200202284945410-Bg79/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions.\n\n - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship:\n \n - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time.\n \n - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention.\n \n - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew.\n\n\nWHAT YOU'LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects strategists on our TMT team work on:\n\n - Scope and launch a subscription-retention agent for a telecommunications or media company, then tune it to save more at-risk customers while preserving trust and brand voice.\n\n - Launch a top-of-funnel sales agent for a telecommunications provider that qualifies prospects, recommends plans and devices, and converts interest into new subscriptions.\n\n - Build a new-subscriber onboarding agent that activates service, ports numbers, configures devices, and reduces early-life churn.\n\n - Create a proactive, long-running agent that detects service or account issues, reaches out across channels, and manages resolution before the customer contacts support.\n\n - Develop a media growth agent that drives content discovery, trial conversion, plan upgrades, and subscription renewal.\n\n - Partner with Product to develop capabilities for TMT-scale traffic, including low-latency voice, multilingual experiences, proactive communications, and resilient performance during major launches or service events.\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts — reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n - Interest in telecommunications, media, and technology. Experience in telecom, streaming and digital media, enterprise or consumer technology, or subscription businesses — and familiarity with customer care, billing, identity, content, or technical support systems — is a strong plus.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business.\n\n - Client-facing consulting, solutions, or strategy experience in a technically complex environment.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"fd5df98a-e2c8-4d47-a803-daee5cccb36f","title":"Software Engineer, Agent - Tech, Media & Telecom","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-09-23T17:08:47.244+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/fd5df98a-e2c8-4d47-a803-daee5cccb36f","applyUrl":"https://jobs.ashbyhq.com/sierra/fd5df98a-e2c8-4d47-a803-daee5cccb36f/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide.
We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup drive millions of customer interactions.
We bring Sierra’s Horizon vision to TMT by building agents that transform the entire customer relationship:
Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time.
Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention.
Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Create agents that pursue goals over weeks and months, reasoning about when to reach out, which channel to use, and what next action will move a customer relationship forward.
Develop personalization and experimentation systems powered by Sierra's Context Engine that combine customer data, behavior, prior conversations, and real-time context to determine the right offer or experience, then learn from every interaction and experiment to autonomously improve personalization over time.
Design conversational discovery agents that reason across huge content catalogs and rich subscriber context, using interests, history, entitlements, and the moment at hand to help someone quickly find something they'll actually want to watch, read, or listen to.
Build agents that troubleshoot deeply integrated telecommunications and connected-device experiences, reasoning across account, billing, network, and device systems to diagnose issues and take the actions needed to resolve them.
Experiment with new voice experiences and Voice Personas tailored to each brand, customer, and moment, bringing the right empathy, energy, and conversational style to everything from navigating a frustrating telecom billing issue to helping someone discover their next favorite show or find the plan that's right for them.
Experience building and scaling end-to-end production systems.
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.
A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.
Comfort working directly with customers to understand their needs and solve real-world problems.
Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.
Excitement in the Tech, Media & Telecom space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers.
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE TECH, MEDIA & TELECOM TEAM\n\n - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide.\n\n - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-activity-7491200203899760641-I27d?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions.\n\n - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship:\n \n - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time.\n \n - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention.\n \n - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Create agents that pursue goals over weeks and months, reasoning about when to reach out, which channel to use, and what next action will move a customer relationship forward.\n\n - Develop personalization and experimentation systems powered by Sierra's Context Engine https://sierra.ai/blog/context-engine that combine customer data, behavior, prior conversations, and real-time context to determine the right offer or experience, then learn from every interaction and experiment to autonomously improve personalization over time.\n\n - Design conversational discovery agents that reason across huge content catalogs and rich subscriber context, using interests, history, entitlements, and the moment at hand to help someone quickly find something they'll actually want to watch, read, or listen to.\n\n - Build agents that troubleshoot deeply integrated telecommunications and connected-device experiences, reasoning across account, billing, network, and device systems to diagnose issues and take the actions needed to resolve them.\n\n - Experiment with new voice experiences and Voice Personas https://sierra.ai/blog/introducing-voice-personas tailored to each brand, customer, and moment, bringing the right empathy, energy, and conversational style to everything from navigating a frustrating telecom billing issue to helping someone discover their next favorite show or find the plan that's right for them.\n\n\nWHAT YOU'LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments.\n\n - A builder and tinkerer's mindset with high agency - you find creative ways to overcome obstacles and ship.\n\n - Comfort working directly with customers to understand their needs and solve real-world problems.\n\n - Excellent communication skills—clear, direct, and persuasive across technical and non-technical audiences.\n\n - Excitement in the Tech, Media & Telecom space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"6c3fa1ef-5eea-4afc-967e-2d3bb920ad96","title":"Strategist, Agent Development (MBA Grad 2027)","department":"Product","team":"Agent Strategist","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}}],"publishedAt":"2026-10-08T21:54:31.172+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/6c3fa1ef-5eea-4afc-967e-2d3bb920ad96","applyUrl":"https://jobs.ashbyhq.com/sierra/6c3fa1ef-5eea-4afc-967e-2d3bb920ad96/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
This role is open to MBA students graduating in spring 2027.
As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.
Own the Agent Development Life Cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.
Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.
Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.
Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.
These are the kinds of projects that strategists on our team have worked on recently:
Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.
Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.
Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog for examples.
Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.
Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome week over week.
Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.
Communication. Clear, direct, and persuasive across technical and non-technical audiences.
Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.
Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.
Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.
Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.
You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.
A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or experience at the intersection of technology and business.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\nThis role is open to MBA students graduating in spring 2027. \n\n\nWHAT YOU’LL DO\n\nAs an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business.\n\n - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome.\n\n - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there.\n\n - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch.\n\n - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next.\n\n\n\n\nEXAMPLE PROJECTS\n\nThese are the kinds of projects that strategists on our team have worked on recently:\n\n - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers.\n\n - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation.\n\n - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples.\n\n - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner.\n\n - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week.\n\n\n\n\nWHAT YOU’LL BRING\n\n - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships.\n\n - Communication. Clear, direct, and persuasive across technical and non-technical audiences.\n\n - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast.\n\n - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion.\n\n - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes.\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts.\n\n - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed.\n\n - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or experience at the intersection of technology and business.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"4190df3f-177e-46c3-8881-5ce55c653b4d","title":"Partnerships Account Manager","department":"Partnerships","team":"Partnerships","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-09T17:05:47.976+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/4190df3f-177e-46c3-8881-5ce55c653b4d","applyUrl":"https://jobs.ashbyhq.com/sierra/4190df3f-177e-46c3-8881-5ce55c653b4d/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Drive partner activation through onboarding, enablement, certification, governance, and operational support programs that help product, strategic, and channel partners become productive quickly.
Build and continuously improve the systems, playbooks, processes, and partner-facing resources that enable Sierra’s partnership ecosystem to scale, including onboarding guides, enablement content, FAQs, and operational documentation.
Coordinate cross-functional execution across Product, Engineering, Sales, Solutions Engineering, Customer Success, Marketing, Legal, GTM Operations, and Partnerships to support product launches, technology integrations, joint GTM programs, co-sell motions, and strategic initiatives.
Plan and execute ongoing partner engagement and governance, including enablement sessions, webinars, QBRs, executive business reviews, newsletters, office hours, partner events, and ongoing partnership management.
Build reporting and use data to improve partnership health, tracking partner activation, engagement, pipeline contribution, partner-influenced revenue, and overall performance while identifying friction and continuously improving how Sierra launches, activates, and scales partnerships.
6+ years of experience in partnership management, partner programs, partner success, ecosystem operations, program management, or a related function within an enterprise SaaS company.
Experience launching, activating, and scaling strategic partnerships, including partner onboarding, enablement, certification, joint GTM execution, technology launches, and ongoing partner success.
Strong cross-functional operator with experience influencing Product, Engineering, GTM, Customer Success, Marketing, Legal, and external partners without direct authority, and exceptional organizational, communication, analytical, and project management skills.
Comfortable with APIs, integrations, and technical product concepts, with the ability to collaborate closely with technical teams without needing to be an engineer.
Fluent with modern AI tools and workflows, actively using AI to improve your work and understanding how AI is changing enterprise software, customer engagement, and partnership models; thrives in ambiguity and enjoys turning strategy into repeatable execution.
Experience supporting and scaling strategic partnership programs across product and technology partnerships, cloud ecosystems, systems integrators, strategic alliances, or channel networks, ideally in a high-growth global environment.
Experience working across enterprise software ecosystems and partners such as AWS, Google Cloud, Microsoft, Salesforce, ServiceNow, Stripe, Twilio, Snowflake, Databricks, or large global systems integrators, with familiarity across PRM, CRM, partner enablement, learning management, and collaboration platforms.
Technical and AI ecosystem experience, including AI platforms, developer tools, or enterprise software, with prior software development, solutions engineering, or technical implementation experience a plus.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO:\n\n - Drive partner activation through onboarding, enablement, certification, governance, and operational support programs that help product, strategic, and channel partners become productive quickly.\n\n - Build and continuously improve the systems, playbooks, processes, and partner-facing resources that enable Sierra’s partnership ecosystem to scale, including onboarding guides, enablement content, FAQs, and operational documentation.\n\n - Coordinate cross-functional execution across Product, Engineering, Sales, Solutions Engineering, Customer Success, Marketing, Legal, GTM Operations, and Partnerships to support product launches, technology integrations, joint GTM programs, co-sell motions, and strategic initiatives.\n\n - Plan and execute ongoing partner engagement and governance, including enablement sessions, webinars, QBRs, executive business reviews, newsletters, office hours, partner events, and ongoing partnership management.\n\n - Build reporting and use data to improve partnership health, tracking partner activation, engagement, pipeline contribution, partner-influenced revenue, and overall performance while identifying friction and continuously improving how Sierra launches, activates, and scales partnerships.\n\n\nWHAT YOU'LL BRING:\n\n - 6+ years of experience in partnership management, partner programs, partner success, ecosystem operations, program management, or a related function within an enterprise SaaS company.\n\n - Experience launching, activating, and scaling strategic partnerships, including partner onboarding, enablement, certification, joint GTM execution, technology launches, and ongoing partner success.\n\n - Strong cross-functional operator with experience influencing Product, Engineering, GTM, Customer Success, Marketing, Legal, and external partners without direct authority, and exceptional organizational, communication, analytical, and project management skills.\n\n - Comfortable with APIs, integrations, and technical product concepts, with the ability to collaborate closely with technical teams without needing to be an engineer.\n\n - Fluent with modern AI tools and workflows, actively using AI to improve your work and understanding how AI is changing enterprise software, customer engagement, and partnership models; thrives in ambiguity and enjoys turning strategy into repeatable execution.\n\n\nEVEN BETTER...\n\n - Experience supporting and scaling strategic partnership programs across product and technology partnerships, cloud ecosystems, systems integrators, strategic alliances, or channel networks, ideally in a high-growth global environment.\n\n - Experience working across enterprise software ecosystems and partners such as AWS, Google Cloud, Microsoft, Salesforce, ServiceNow, Stripe, Twilio, Snowflake, Databricks, or large global systems integrators, with familiarity across PRM, CRM, partner enablement, learning management, and collaboration platforms.\n\n - Technical and AI ecosystem experience, including AI platforms, developer tools, or enterprise software, with prior software development, solutions engineering, or technical implementation experience a plus.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"87f2a303-c2a1-484e-9e4b-efdcaafa440e","title":"Software Engineer, Horizon","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-09-24T22:10:13.906+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/87f2a303-c2a1-484e-9e4b-efdcaafa440e","applyUrl":"https://jobs.ashbyhq.com/sierra/87f2a303-c2a1-484e-9e4b-efdcaafa440e/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Build primitives for self improvement: Create the feedback loops, evaluation systems, memory, signals, and decisioning infrastructure that help long-running agents learn from outcomes and improve over time.
Build the future of long-horizon agents: Design and ship agents that pursue complex business outcomes over days, weeks, or months across voice, SMS, email, and other channels.
Turn 0-to-1 work into a platform: Identify patterns and build reusable systems, abstractions, and tools that make future Horizon agents faster and easier to launch.
Solve technically complex problems: Build across orchestration, integrations, data, memory, signals, decisioning, observability, and multi-channel engagement.
Shape the Horizon product: Surface platform gaps through hands-on implementation and work with product and engineering to define Horizon’s architecture and roadmap.
Create a clean path beyond the POC: Once a solution is validated, translate what you built into durable product capabilities and enable a successful handoff for continued deployment.
Experience building and scaling end-to-end production systems.
Strong platform and systems engineering fundamentals.
The ability to move between customer problems, product design, and technical implementation.
Strong technical judgment in ambiguous, fast-changing environments.
A builder’s mindset and the ability to take products from zero to one.
Comfort working directly with customers and understanding complex business processes.
High agency, adaptability, and clear communication.
At least two years of professional software engineering experience
Experience with Python, TypeScript, or Go and React.
Experience as a founder, founding engineer, or early engineer at a startup.
Experience building workflow, orchestration, event-driven, or distributed systems.
Experience developing platforms or reusable infrastructure for other engineers.
Experience building or deploying AI and LLM-powered products.
Familiarity with enterprise integrations, APIs, data pipelines, and systems of record.
Experience working in complex industries such as financial services or healthcare.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Build primitives for self improvement: Create the feedback loops, evaluation systems, memory, signals, and decisioning infrastructure that help long-running agents learn from outcomes and improve over time.\n\n - Build the future of long-horizon agents: Design and ship agents that pursue complex business outcomes over days, weeks, or months across voice, SMS, email, and other channels.\n\n - Turn 0-to-1 work into a platform: Identify patterns and build reusable systems, abstractions, and tools that make future Horizon agents faster and easier to launch.\n\n - Solve technically complex problems: Build across orchestration, integrations, data, memory, signals, decisioning, observability, and multi-channel engagement.\n\n - Shape the Horizon product: Surface platform gaps through hands-on implementation and work with product and engineering to define Horizon’s architecture and roadmap.\n\n - Create a clean path beyond the POC: Once a solution is validated, translate what you built into durable product capabilities and enable a successful handoff for continued deployment.\n\n\nWHAT YOU’LL BRING\n\n - Experience building and scaling end-to-end production systems.\n\n - Strong platform and systems engineering fundamentals.\n\n - The ability to move between customer problems, product design, and technical implementation.\n\n - Strong technical judgment in ambiguous, fast-changing environments.\n\n - A builder’s mindset and the ability to take products from zero to one.\n\n - Comfort working directly with customers and understanding complex business processes.\n\n - High agency, adaptability, and clear communication.\n\n - At least two years of professional software engineering experience\n\n - Experience with Python, TypeScript, or Go and React.\n\n\nEVEN BETTER\n\n - Experience as a founder, founding engineer, or early engineer at a startup.\n\n - Experience building workflow, orchestration, event-driven, or distributed systems.\n\n - Experience developing platforms or reusable infrastructure for other engineers.\n\n - Experience building or deploying AI and LLM-powered products.\n\n - Familiarity with enterprise integrations, APIs, data pipelines, and systems of record.\n\n - Experience working in complex industries such as financial services or healthcare.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"460d88d5-6ae9-4cf8-95e8-c6d29aa4e5f2","title":"Sales Engineering Manager, APJ","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-09-25T10:34:24.935+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/460d88d5-6ae9-4cf8-95e8-c6d29aa4e5f2","applyUrl":"https://jobs.ashbyhq.com/sierra/460d88d5-6ae9-4cf8-95e8-c6d29aa4e5f2/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Team leadership: Manage and mentor a team of Sales Engineers, providing support to help onboard and develop team members. This role reports to our Head of Sales Engineering.
Set clear performance expectations: Establish and communicate key performance indicators (KPIs) and objectives for the team. Monitor individual and team performance to ensure everyone is working towards meeting or exceeding goals.
GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.
Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.
Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.
Identify & strengthen partnerships: Identify opportunities and strengthen partnership between Sales Engineering and Sales teams to ensure alignment in objectives, seamless customer engagement, and efficient handoffs. Promote a culture of teamwork and shared goals, creating joint strategies to enhance both technical and commercial outcomes.
Lead across APJ: Build and lead the Sales Engineering team across Southeast Asia, Australia & New Zealand, Korea, and Japan. Adapt our technical sales motion to each market's customers, languages, and buying processes, and partner with regional Sales leaders to grow Sierra's presence across the region.
6+ years experience in managing a team of Sales Engineers or Solutions Engineers.
Past experience in demo building, and presenting, and working with customers or clients in the GTM function.
Experience in relationship-building with potential customers, including executives and technical leaders.
Experience in leading the sales process with Enterprise customers.
A track record of deploying and leading Sales Engineering or Solutions Engineering teams across APJ markets, including Southeast Asia, ANZ, Korea, and Japan.
Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience
Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Team leadership: Manage and mentor a team of Sales Engineers, providing support to help onboard and develop team members. This role reports to our Head of Sales Engineering.\n\n - Set clear performance expectations: Establish and communicate key performance indicators (KPIs) and objectives for the team. Monitor individual and team performance to ensure everyone is working towards meeting or exceeding goals.\n\n - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions.\n\n - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy.\n\n - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution.\n\n - Identify & strengthen partnerships: Identify opportunities and strengthen partnership between Sales Engineering and Sales teams to ensure alignment in objectives, seamless customer engagement, and efficient handoffs. Promote a culture of teamwork and shared goals, creating joint strategies to enhance both technical and commercial outcomes.\n\n - Lead across APJ: Build and lead the Sales Engineering team across Southeast Asia, Australia & New Zealand, Korea, and Japan. Adapt our technical sales motion to each market's customers, languages, and buying processes, and partner with regional Sales leaders to grow Sierra's presence across the region. \n\n \n\n\nWHAT YOU'LL BRING\n\n - 6+ years experience in managing a team of Sales Engineers or Solutions Engineers. \n\n - Past experience in demo building, and presenting, and working with customers or clients in the GTM function.\n\n - Experience in relationship-building with potential customers, including executives and technical leaders.\n\n - Experience in leading the sales process with Enterprise customers.\n\n - A track record of deploying and leading Sales Engineering or Solutions Engineering teams across APJ markets, including Southeast Asia, ANZ, Korea, and Japan.\n\n - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience\n\n - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"693984cb-bc25-4d14-ac2f-ad2fbe6e0cd9","title":"Recruiting Coordinator (Contract)","department":"Operations","team":"Recruiting","employmentType":"FullTime","location":"Tokyo","secondaryLocations":[],"publishedAt":"2026-09-21T16:05:56.609+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Japan"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/693984cb-bc25-4d14-ac2f-ad2fbe6e0cd9","applyUrl":"https://jobs.ashbyhq.com/sierra/693984cb-bc25-4d14-ac2f-ad2fbe6e0cd9/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Coordinate a high volume of phone, onsite, and video conference interviews with speed and efficiency
Leverage applicant tracking system (Ashby) to automate tasks and focus on candidate experience
Improve efficiency by maintaining data accuracy and gathering metrics to help prepare reports to keep recruiters and hiring managers on target
Demonstrate ability to work effectively under pressure and manage multiple tasks simultaneously
Manage candidate travel arrangements and process expense claims
Meet and greet candidates while they are onsite for interviews
Deliver a best-in-class recruiting experience for all candidates
Take on projects to impact our workflow and office experiences
2+ years of experience as a Recruiting Coordinator in a scaling company
Able to communicate fluently in both English and Japanese
Operational excellence, a data-driven mindset, and a great attitude for multitasking and problem-solving
High level of integrity and trustworthiness, maintaining candidate confidentiality and privacy
Demonstrated experience in coordinating schedules and managing communications with C-suite leadership, ensuring efficient and effective collaboration
Ability to be in person in our office, Monday - Thursday
Experience working in an in-office culture
Ashby ATS experience
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Coordinate a high volume of phone, onsite, and video conference interviews with speed and efficiency\n\n - Leverage applicant tracking system (Ashby) to automate tasks and focus on candidate experience\n\n - Improve efficiency by maintaining data accuracy and gathering metrics to help prepare reports to keep recruiters and hiring managers on target\n\n - Demonstrate ability to work effectively under pressure and manage multiple tasks simultaneously\n\n - Manage candidate travel arrangements and process expense claims\n\n - Meet and greet candidates while they are onsite for interviews\n\n - Deliver a best-in-class recruiting experience for all candidates\n\n - Take on projects to impact our workflow and office experiences\n\n\nWHAT YOU'LL BRING\n\n - 2+ years of experience as a Recruiting Coordinator in a scaling company\n\n - Able to communicate fluently in both English and Japanese\n\n - Operational excellence, a data-driven mindset, and a great attitude for multitasking and problem-solving\n\n - High level of integrity and trustworthiness, maintaining candidate confidentiality and privacy\n\n - Demonstrated experience in coordinating schedules and managing communications with C-suite leadership, ensuring efficient and effective collaboration \n\n - Ability to be in person in our office, Monday - Thursday\n\n\nEVEN BETTER...\n\n - Experience working in an in-office culture\n\n - Ashby ATS experience\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"89b2027d-d019-46ca-8071-f8a1a4e647d8","title":"Area Vice President, Public Sector","department":"Sales","team":"Sales","employmentType":"FullTime","location":"US - Remote","secondaryLocations":[{"location":"San Francisco, CA","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Washington, D.C.","address":{"postalAddress":{"addressRegion":"DC","addressCountry":"United States of America","addressLocality":"Washington DC "}}}],"publishedAt":"2026-09-28T21:57:13.099+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States","addressLocality":""}},"jobUrl":"https://jobs.ashbyhq.com/sierra/89b2027d-d019-46ca-8071-f8a1a4e647d8","applyUrl":"https://jobs.ashbyhq.com/sierra/89b2027d-d019-46ca-8071-f8a1a4e647d8/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra recently received FedRAMP High certification and were awarded our first contract with a federal agency. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.
Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.
We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.
In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Build and lead Sierra’s public sector sales team: Recruit, develop, and lead a team of account executives serving strategic federal, state, or local government accounts. Set clear expectations, coach for performance, and build a culture of customer obsession, accountability, and consistent execution.
Own revenue growth and territory strategy: Translate Sierra’s public sector ambitions into territory coverage, account priorities, pipeline goals, and revenue plans. Allocate resources thoughtfully, maintain rigorous forecasts, and drive the team to consistently achieve or exceed revenue targets.
Create opportunities around mission outcomes: Build executive relationships with agency leaders and help your team translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. Serve as an executive sponsor for strategic accounts.
Guide complex sales cycles from discovery through award: Coach account executives through long, multi-stakeholder government buying processes and engage directly at critical moments. Mobilize cross-functional support for executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close.
Shape acquisition and capture strategy: Ensure every priority opportunity has a credible path to contract and a disciplined capture plan. Help the team navigate funding, fiscal-year timing, competitive dynamics, and procurement pathways—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements. Lead deal reviews that surface risks early and turn strategy into clear next steps.
Scale Sierra’s partner ecosystem: Partner with public sector and partnerships leadership to build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and technology providers. Guide decisions about direct sales, subcontracting, teaming, and partner-led transactions to expand customer access and accelerate growth.
Lead strategic prime and teaming relationships: Establish executive alignment with key partners and help shape account ownership, deal registration, workshare, and joint go-to-market plans. Ensure partnerships bring meaningful customer access, past performance, implementation capacity, or procurement pathways—and translate into qualified pipeline and successful delivery.
Drive disciplined pursuit and proposal decisions: Partner with the Public Sector GM on bid/no-bid recommendations and prioritize resources across strategic pursuits. Align sales, legal, security, product, engineering, and delivery teams to produce procurement responses that are compliant, differentiated, and precise.
Stay accountable for customer success: Build trust with senior agency leaders, establish strong handoffs from sales to delivery, and remain engaged through deployment and expansion. Help resolve escalations and ensure commitments made during the sales process support lasting customer relationships.
Build a repeatable public sector go-to-market motion: Work with public sector leadership to refine account segmentation, hiring and capacity plans, capture processes, partner strategy, contract-vehicle priorities, and sales playbooks. Bring market signals and customer feedback to product and company leadership to shape Sierra’s platform and public sector strategy.
Lead an AI-native sales organization: Embed AI into how the team researches accounts, develops outreach, synthesizes calls, plans opportunities, creates proposals, and forecasts. Model effective use, share successful practices, and help account executives spend more time on judgment, strategy, and customer relationships.
15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, specifically selling to the U.S. government.
People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team.
Enterprise experience: You've run and managed end-to-end complex deals ($1M+).
Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles.
Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public.
A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners.
Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity.
The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward.
Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps.
A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve.
Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE PUBLIC SECTOR TEAM\n\n - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification and were awarded our first contract with a federal agency. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry.\n\n - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies.\n\n - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions.\n\n - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\n\nWHAT YOU'LL DO\n\n - Build and lead Sierra’s public sector sales team: Recruit, develop, and lead a team of account executives serving strategic federal, state, or local government accounts. Set clear expectations, coach for performance, and build a culture of customer obsession, accountability, and consistent execution.\n\n - Own revenue growth and territory strategy: Translate Sierra’s public sector ambitions into territory coverage, account priorities, pipeline goals, and revenue plans. Allocate resources thoughtfully, maintain rigorous forecasts, and drive the team to consistently achieve or exceed revenue targets.\n\n - Create opportunities around mission outcomes: Build executive relationships with agency leaders and help your team translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. Serve as an executive sponsor for strategic accounts.\n\n - Guide complex sales cycles from discovery through award: Coach account executives through long, multi-stakeholder government buying processes and engage directly at critical moments. Mobilize cross-functional support for executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close.\n\n - Shape acquisition and capture strategy: Ensure every priority opportunity has a credible path to contract and a disciplined capture plan. Help the team navigate funding, fiscal-year timing, competitive dynamics, and procurement pathways—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements. Lead deal reviews that surface risks early and turn strategy into clear next steps.\n\n - Scale Sierra’s partner ecosystem: Partner with public sector and partnerships leadership to build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and technology providers. Guide decisions about direct sales, subcontracting, teaming, and partner-led transactions to expand customer access and accelerate growth.\n\n - Lead strategic prime and teaming relationships: Establish executive alignment with key partners and help shape account ownership, deal registration, workshare, and joint go-to-market plans. Ensure partnerships bring meaningful customer access, past performance, implementation capacity, or procurement pathways—and translate into qualified pipeline and successful delivery.\n\n - Drive disciplined pursuit and proposal decisions: Partner with the Public Sector GM on bid/no-bid recommendations and prioritize resources across strategic pursuits. Align sales, legal, security, product, engineering, and delivery teams to produce procurement responses that are compliant, differentiated, and precise.\n\n - Stay accountable for customer success: Build trust with senior agency leaders, establish strong handoffs from sales to delivery, and remain engaged through deployment and expansion. Help resolve escalations and ensure commitments made during the sales process support lasting customer relationships.\n\n - Build a repeatable public sector go-to-market motion: Work with public sector leadership to refine account segmentation, hiring and capacity plans, capture processes, partner strategy, contract-vehicle priorities, and sales playbooks. Bring market signals and customer feedback to product and company leadership to shape Sierra’s platform and public sector strategy.\n\n - Lead an AI-native sales organization: Embed AI into how the team researches accounts, develops outreach, synthesizes calls, plans opportunities, creates proposals, and forecasts. Model effective use, share successful practices, and help account executives spend more time on judgment, strategy, and customer relationships.\n\n\nWHAT YOU'LL BRING\n\n - 15+ years of selling experience: Extensive experience in enterprise customer-facing sales role, specifically selling to the U.S. government.\n\n - People leadership experience: 10+ years managing, mentoring, and developing a high-performing enterprise sales team.\n\n - Enterprise experience: You've run and managed end-to-end complex deals ($1M+).\n\n - Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles.\n\n - Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public.\n\n - A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners.\n\n - Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity.\n\n - The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward.\n\n - Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps.\n\n - A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve.\n\n - Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"49049bf3-c1bb-4109-ab10-b222f3057225","title":"Order Management","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-06T00:02:34.251+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/49049bf3-c1bb-4109-ab10-b222f3057225","applyUrl":"https://jobs.ashbyhq.com/sierra/49049bf3-c1bb-4109-ab10-b222f3057225/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
You'll own the operational backbone that connects what we sell to what we bill: turning executed contracts and agent usage into accurate bookings and reports, and turning the data behind both into critical insights the business acts on. This role sits at the center of the company’s business model and works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development.
Own Order Management across the Customer Lifecycle
Own the path from signature to booking: build, verify, and book quotes across the customer lifecycle, capturing all critical commercial terms
Collaborate across GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into all downstream systems and reporting
Leverage and spearhead order management guides and best practices, influencing policies and processes as new terms and products emerge
Accelerate usage tracking and reporting
Partner with Agent Development to set up, verify, and maintain outcome-based usage tracking across agents
Run the monthly consumption reporting and billing cycle for our growing customer base, delivering key reports to the company and to the Customer
Serve as the owner for usage questions from customers, Sales, and Agent Development
Support our Deal Operations and Velocity
Draft, review, and execute order forms, working with our Pricing team to align on commercial negotiation, deal forecast, and downstream operability
Partner with Sales, Legal, Pricing, and Finance across the deal lifecycle to execute deals cleanly and drive scalability over time
Build the Operational Machine with us
Continuously identify repetitive processes across the order management lifecycle and collaborate across the Go-to-Market Operations team to automate and scale them
Work with Revenue Operations and GTM systems to define billing processes and policies for new products and pricing models
Ramp from running standard processes to owning complex and ambiguous scenarios
2–4 years in deal desk, order management, billing operations, or revenue operations at a B2B SaaS company
Experience owning an operational booking and/or billing queue end-to-end with high accuracy against monthly deadlines
Experience with CRMs (e.g., Salesforce) and a CPQ or billing system; comfortable reading a contract and translating terms into system fields
Strong attention to detail and clear written communication skills to collaborate with Sales, Finance, Legal, and customers
Ability to identify areas for improvement and build solutions using AI tooling
Based in San Francisco and able to work in-office with the team
Experience with usage-based billing (commitments, overages, credits, true-ups)
Familiarity with Quoting and Contract Lifecycle Management tools
SQL or spreadsheet modeling skills
Exposure to sales compensation, revenue recognition, or partner and reseller billing
Experience at a high-growth company where you helped stand up a process from scratch
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nYou'll own the operational backbone that connects what we sell to what we bill: turning executed contracts and agent usage into accurate bookings and reports, and turning the data behind both into critical insights the business acts on. This role sits at the center of the company’s business model and works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development.\n\nOwn Order Management across the Customer Lifecycle\n\n - Own the path from signature to booking: build, verify, and book quotes across the customer lifecycle, capturing all critical commercial terms\n\n - Collaborate across GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into all downstream systems and reporting\n\n - Leverage and spearhead order management guides and best practices, influencing policies and processes as new terms and products emerge\n\nAccelerate usage tracking and reporting\n\n - Partner with Agent Development to set up, verify, and maintain outcome-based usage tracking across agents\n\n - Run the monthly consumption reporting and billing cycle for our growing customer base, delivering key reports to the company and to the Customer\n\n - Serve as the owner for usage questions from customers, Sales, and Agent Development\n\nSupport our Deal Operations and Velocity\n\n - Draft, review, and execute order forms, working with our Pricing team to align on commercial negotiation, deal forecast, and downstream operability\n\n - Partner with Sales, Legal, Pricing, and Finance across the deal lifecycle to execute deals cleanly and drive scalability over time\n\nBuild the Operational Machine with us\n\n - Continuously identify repetitive processes across the order management lifecycle and collaborate across the Go-to-Market Operations team to automate and scale them\n\n - Work with Revenue Operations and GTM systems to define billing processes and policies for new products and pricing models\n\n - Ramp from running standard processes to owning complex and ambiguous scenarios\n\n\n\n\nWHAT YOU’LL BRING\n\n - 2–4 years in deal desk, order management, billing operations, or revenue operations at a B2B SaaS company\n\n - Experience owning an operational booking and/or billing queue end-to-end with high accuracy against monthly deadlines\n\n - Experience with CRMs (e.g., Salesforce) and a CPQ or billing system; comfortable reading a contract and translating terms into system fields\n\n - Strong attention to detail and clear written communication skills to collaborate with Sales, Finance, Legal, and customers\n\n - Ability to identify areas for improvement and build solutions using AI tooling\n\n - Based in San Francisco and able to work in-office with the team\n \n \n\n\nEVEN BETTER…\n\n - Experience with usage-based billing (commitments, overages, credits, true-ups)\n\n - Familiarity with Quoting and Contract Lifecycle Management tools\n\n - SQL or spreadsheet modeling skills\n\n - Exposure to sales compensation, revenue recognition, or partner and reseller billing\n\n - Experience at a high-growth company where you helped stand up a process from scratch\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"7986993b-646f-4a27-b55a-decd6990448c","title":"Regional VP, Sales (South East Asia)","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Singapore","secondaryLocations":[],"publishedAt":"2026-10-09T10:48:03.869+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressCountry":"Singapore","addressLocality":"Singapore"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/7986993b-646f-4a27-b55a-decd6990448c","applyUrl":"https://jobs.ashbyhq.com/sierra/7986993b-646f-4a27-b55a-decd6990448c/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.
Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.
Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.
10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.
People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.
Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.
Strong Communication Skills: Exceptional verbal and written communication abilities.
Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team.\n\n - Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights.\n\n - Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy.\n\n\nWHAT YOU'LL BRING\n\n - 10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts.\n\n - People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team.\n\n - Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals.\n\n - Strong Communication Skills: Exceptional verbal and written communication abilities.\n\n - Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.\n\n\nEVEN BETTER...\n\n - Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends.\n\n - Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"1f8e393a-c50f-4616-b808-521e72d90139","title":"Sales Compensation Analyst","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-06T00:05:21.974+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/1f8e393a-c50f-4616-b808-521e72d90139","applyUrl":"https://jobs.ashbyhq.com/sierra/1f8e393a-c50f-4616-b808-521e72d90139/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Run the monthly and quarterly commission cycle, from pulling data and calculating commissions to validating payouts, getting approvals and handing off to payroll.
Investigate rep questions, document what you find, recommend fixes, and clear issues quickly so reps trust their payouts.
Work with Salesforce and data owners to keep source data clean, map new fields and deal types, and find upstream problems before they turn into payout errors.
Reconcile and audit payouts against payroll, bookings and plan terms every cycle.
Model the cost and payout impact of proposed plan changes and set up new plans in the system.
Automate manual steps, tighten SLAs and build reporting on attainment, payout cost and comp effectiveness.
5+ years in sales compensation, commissions operations or a closely related finance/RevOps role.
A track record of managing commission cycles across multiple regions, currencies, and payroll schedules, from data collection through payout validation, approvals, and payroll handoff.
Strong analytical skills, including payout modeling, data reconciliation, and investigating discrepancies against compensation plan terms.
Experience using Salesforce to pull and review sales data for commission calculations.
Ability to configure sales compensation tools to calculate, validate, and report commission payouts.
Clear, calm communication with sellers and leaders, including during difficult payout conversations.
Familiarity with commission accounting, including accruals, journal entries, and month-end close.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Run the monthly and quarterly commission cycle, from pulling data and calculating commissions to validating payouts, getting approvals and handing off to payroll.\n\n - Investigate rep questions, document what you find, recommend fixes, and clear issues quickly so reps trust their payouts.\n\n - Work with Salesforce and data owners to keep source data clean, map new fields and deal types, and find upstream problems before they turn into payout errors.\n\n - Reconcile and audit payouts against payroll, bookings and plan terms every cycle.\n\n - Model the cost and payout impact of proposed plan changes and set up new plans in the system.\n\n - Automate manual steps, tighten SLAs and build reporting on attainment, payout cost and comp effectiveness.\n\n\nWHAT YOU’LL BRING\n\n - 5+ years in sales compensation, commissions operations or a closely related finance/RevOps role.\n\n - A track record of managing commission cycles across multiple regions, currencies, and payroll schedules, from data collection through payout validation, approvals, and payroll handoff.\n\n - Strong analytical skills, including payout modeling, data reconciliation, and investigating discrepancies against compensation plan terms.\n\n - Experience using Salesforce to pull and review sales data for commission calculations.\n\n - Ability to configure sales compensation tools to calculate, validate, and report commission payouts.\n\n - Clear, calm communication with sellers and leaders, including during difficult payout conversations.\n\n\nEVEN BETTER…\n\n - Familiarity with commission accounting, including accruals, journal entries, and month-end close.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b8666a78-fcb1-47bb-ad07-5edb6cd3ad71","title":"Software Engineer, Inference","department":"Engineering","team":"Platform Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-05T23:30:38.889+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b8666a78-fcb1-47bb-ad07-5edb6cd3ad71","applyUrl":"https://jobs.ashbyhq.com/sierra/b8666a78-fcb1-47bb-ad07-5edb6cd3ad71/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra’s AI agents depend on foundation models to reason and act in real time. The Inference team builds the systems that make those models fast, reliable, and efficient at scale.
As a Software Engineer on Inference, you’ll help define Sierra’s inference architecture across both self-hosted models and third-party inference providers. You’ll work on the systems responsible for serving and routing inference, managing capacity and quota, and optimizing for latency, reliability, and cost.
This is a systems-first role at the intersection of distributed infrastructure and AI. You don’t need to be an ML researcher—we’re looking for engineers who love complex systems problems and are excited to apply that expertise to one of the fastest-moving areas of AI infrastructure.
Partner with frontier labs and providers. At our scale, we rely on frontier labs, and inference providers to supply capacity, training and inference infrastructure.
Shape Sierra’s inference architecture. Design how inference traffic flows across models, infrastructure, and providers, including new serving and proxy layers as Sierra scales.
Build for low latency and high reliability. Develop systems for routing, failover, capacity management, and quota that keep inference performant and available across large-scale production workloads.
Build and operate self-hosted inference. Run models on GPU infrastructure, from building containers and operating inference engines to managing the underlying compute capacity.
Optimize inference performance. Work with the Applied Research team on techniques such as speculative decoding and serving-engine optimizations that improve latency, throughput, and cost.
Build across a hybrid inference stack. Work with both Sierra-managed infrastructure and leading inference platforms, making architectural decisions about where and how workloads should run.
Push the serving stack forward. Work closely with inference providers to tune engines and infrastructure for Sierra’s workloads.
Support the broader model lifecycle. Contribute to infrastructure that enables post-training while partnering closely with our Models and Agent Runtime teams.
Deep systems thinking and strong distributed systems fundamentals.
Experience designing, building, and operating large-scale production systems.
Strong judgment around tradeoffs involving latency, reliability, capacity, and cost.
Experience taking ownership of complex infrastructure from architecture through production operation.
Excitement about applying systems expertise to AI infrastructure and learning quickly as the underlying technology evolves.
Experience with ML infrastructure, MLOps, or production inference systems.
Experience serving LLMs or other large models at scale.
Experience operating self-hosted inference and GPU infrastructure.
Familiarity with inference frameworks such as vLLM or SGLang.
Experience with post-training infrastructure or inference-performance optimization.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE ROLE\n\nSierra’s AI agents depend on foundation models to reason and act in real time. The Inference team builds the systems that make those models fast, reliable, and efficient at scale.\n\nAs a Software Engineer on Inference, you’ll help define Sierra’s inference architecture across both self-hosted models and third-party inference providers. You’ll work on the systems responsible for serving and routing inference, managing capacity and quota, and optimizing for latency, reliability, and cost.\n\nThis is a systems-first role at the intersection of distributed infrastructure and AI. You don’t need to be an ML researcher—we’re looking for engineers who love complex systems problems and are excited to apply that expertise to one of the fastest-moving areas of AI infrastructure.\n\n\n\n\nWHAT YOU'LL DO\n\n - Partner with frontier labs and providers. At our scale, we rely on frontier labs, and inference providers to supply capacity, training and inference infrastructure.\n\n - Shape Sierra’s inference architecture. Design how inference traffic flows across models, infrastructure, and providers, including new serving and proxy layers as Sierra scales.\n\n - Build for low latency and high reliability. Develop systems for routing, failover, capacity management, and quota that keep inference performant and available across large-scale production workloads.\n\n - Build and operate self-hosted inference. Run models on GPU infrastructure, from building containers and operating inference engines to managing the underlying compute capacity.\n\n - Optimize inference performance. Work with the Applied Research team on techniques such as speculative decoding and serving-engine optimizations that improve latency, throughput, and cost.\n\n - Build across a hybrid inference stack. Work with both Sierra-managed infrastructure and leading inference platforms, making architectural decisions about where and how workloads should run.\n\n - Push the serving stack forward. Work closely with inference providers to tune engines and infrastructure for Sierra’s workloads.\n\n - Support the broader model lifecycle. Contribute to infrastructure that enables post-training while partnering closely with our Models and Agent Runtime teams.\n\n\nWHAT YOU'LL BRING\n\n - Deep systems thinking and strong distributed systems fundamentals.\n\n - Experience designing, building, and operating large-scale production systems.\n\n - Strong judgment around tradeoffs involving latency, reliability, capacity, and cost.\n\n - Experience taking ownership of complex infrastructure from architecture through production operation.\n\n - Excitement about applying systems expertise to AI infrastructure and learning quickly as the underlying technology evolves.\n\n\nEVEN BETTER\n\n - Experience with ML infrastructure, MLOps, or production inference systems.\n\n - Experience serving LLMs or other large models at scale.\n\n - Experience operating self-hosted inference and GPU infrastructure.\n\n - Familiarity with inference frameworks such as vLLM or SGLang.\n\n - Experience with post-training infrastructure or inference-performance optimization.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"b5606bd2-4f10-4b44-8d81-f1e12f26d3ba","title":"Partnerships Development Lead","department":"Partnerships","team":"Partnerships","employmentType":"FullTime","location":"London","secondaryLocations":[],"publishedAt":"2026-10-07T14:28:20.630+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"England","addressCountry":"United Kingdom","addressLocality":"London"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/b5606bd2-4f10-4b44-8d81-f1e12f26d3ba","applyUrl":"https://jobs.ashbyhq.com/sierra/b5606bd2-4f10-4b44-8d81-f1e12f26d3ba/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
As a Partnerships Development Lead, you’ll play a critical role in building and nurturing a robust ecosystem of partners and stakeholders around Sierra, amplifying our reach and market impact.
Industry Partnerships: Develop and grow partnerships with key industry players and technology platforms
Strategic Customer Channels: Explore and cultivate alternative customer acquisition channels beyond traditional sales, leveraging Sierra’s ecosystem of investors, partners, and industry influencers to drive inbound interest and adoption
GTM Strategy & Collaboration: Align partnership efforts with Sierra’s broader GTM approach, collaborating closely with Sales and Marketing
Investor & VC/PE Engagement: Build and deepen relationships with VCs and PE firms to position Sierra as a strategic AI partner across their portfolios. Proactively identify opportunities to introduce Sierra to portfolio companies that would benefit from our agents
Industry & Market Expansion: Gather market intelligence, share insights to inform product development, and explore opportunities for potential growth across new market segments and geographies
8+ years in business development, strategic partnerships, or related roles in tech
Strong understanding of the VC/PE landscape and experience working with investors
Proven track record of structuring and closing high-value partnerships with senior stakeholders
Ability to engage and maintain relationships with C-level executives, investors, and key decision-makers
Analytical mindset to evaluate partnership opportunities and align them with Sierra’s long-term vision
Ability to navigate ambiguity in a fast-moving startup environment
Prior experience at a high-growth AI or enterprise SaaS startup
Deep expertise in a few of our key industries: financial services, healthcare, telecommunications, media, travel, transportation and hospitality, retain and consumer goods, and/or technology
Experience structuring and managing ecosystem partnerships
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAs a Partnerships Development Lead, you’ll play a critical role in building and nurturing a robust ecosystem of partners and stakeholders around Sierra, amplifying our reach and market impact.\n\n - Industry Partnerships: Develop and grow partnerships with key industry players and technology platforms\n\n - Strategic Customer Channels: Explore and cultivate alternative customer acquisition channels beyond traditional sales, leveraging Sierra’s ecosystem of investors, partners, and industry influencers to drive inbound interest and adoption\n\n - GTM Strategy & Collaboration: Align partnership efforts with Sierra’s broader GTM approach, collaborating closely with Sales and Marketing\n\n - Investor & VC/PE Engagement: Build and deepen relationships with VCs and PE firms to position Sierra as a strategic AI partner across their portfolios. Proactively identify opportunities to introduce Sierra to portfolio companies that would benefit from our agents\n\n - Industry & Market Expansion: Gather market intelligence, share insights to inform product development, and explore opportunities for potential growth across new market segments and geographies\n\n\nWHAT YOU’LL BRING\n\n - 8+ years in business development, strategic partnerships, or related roles in tech\n\n - Strong understanding of the VC/PE landscape and experience working with investors\n\n - Proven track record of structuring and closing high-value partnerships with senior stakeholders\n\n - Ability to engage and maintain relationships with C-level executives, investors, and key decision-makers\n\n - Analytical mindset to evaluate partnership opportunities and align them with Sierra’s long-term vision\n\n - Ability to navigate ambiguity in a fast-moving startup environment\n\n\nEVEN BETTER…\n\n - Prior experience at a high-growth AI or enterprise SaaS startup\n\n - Deep expertise in a few of our key industries: financial services, healthcare, telecommunications, media, travel, transportation and hospitality, retain and consumer goods, and/or technology\n\n - Experience structuring and managing ecosystem partnerships\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"9d59c96e-e7f7-43cc-8069-bcdf3798fe2b","title":"Software Engineer, Agent (Spanish speaking)","department":"Engineering","team":"Agent Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[{"location":"New York, NY","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York"}}},{"location":"Toronto","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-10-07T13:15:34.883+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/9d59c96e-e7f7-43cc-8069-bcdf3798fe2b","applyUrl":"https://jobs.ashbyhq.com/sierra/9d59c96e-e7f7-43cc-8069-bcdf3798fe2b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Design and deliver production-grade AI agents: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.
Drive the Agent Development Life Cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.
Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.
Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.
These are some examples of projects that engineers on our team have worked on recently:
Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn
Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations
Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog!
Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development
Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers
Language fluency - professional fluency in both Spanish and English
Experience building and scaling end-to-end production systems
Strong technical problem-solving skills, especially in fast-changing, ambiguous environments
A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship
Comfort working directly with customers to understand their needs and solve real-world problems
Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences
Experience building or deploying AI/LLM systems in production
Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed
Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering
Prior experience with React, TypeScript, and/or Go
Previous roles where you interfaced with customers or led technical projects with external stakeholders
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\n - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce.\n\n - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way.\n\n - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency.\n\n - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product.\n\n\nEXAMPLE PROJECTS\n\nThese are some examples of projects that engineers on our team have worked on recently:\n\n - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn\n\n - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations\n\n - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services!\n\n - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development\n\n - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers\n\n\nWHAT YOU'LL BRING\n\n - Language fluency - professional fluency in both Spanish and English\n\n - Experience building and scaling end-to-end production systems\n\n - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments\n\n - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship\n\n - Comfort working directly with customers to understand their needs and solve real-world problems\n\n - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences\n\n\nEVEN BETTER...\n\n - Experience building or deploying AI/LLM systems in production\n\n - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed\n\n - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering\n\n - Prior experience with React, TypeScript, and/or Go\n\n - Previous roles where you interfaced with customers or led technical projects with external stakeholders\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"fe3a612c-e4f1-447c-a518-3a2a26c5e10b","title":"Sales Engineering Manager, High Growth","department":"Sales","team":"Sales Engineering","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-12T14:00:23.953+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/fe3a612c-e4f1-447c-a518-3a2a26c5e10b","applyUrl":"https://jobs.ashbyhq.com/sierra/fe3a612c-e4f1-447c-a518-3a2a26c5e10b/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Scale The Function: Lead, coach, and develop a high-caliber SE team, providing guidance, assigning projects and ensuring technical excellence. Conduct regular performance evaluations, foster professional growth, and coach team members to reach their full potential.
Player-Coach: Be a true player-coach who stays in the work: own your own enterprise deals as an individual contributor, running discovery, demos, and technical deep dives alongside your team, while leading and growing a team of high-growth enterprise SEs. Set the bar by example, jump into the most strategic cycles, and turn what you learn in the field into coaching and playbooks that raise the whole team. As the team grows, become a strategic leader and more manager focused.
GTM Technical Expert: Guide your team in designing and delivering compelling technical demos and proofs of concept for Sierra’s platform, providing technical solutions to customer challenges, and addressing technical questions throughout the sales cycle.
Cross-Functional Work: Partner closely with Sales, Product, and Agent Engineering teams to define best practices, playbooks, and repeatable processes that enable your team and partnership to scale beyond 1:1 customer interactions.
Lead & Support Customers: Act as a technical leader in early-stage customer conversations, helping your team understand, anticipate, and solve customer needs to advance Sierra’s industry-leading AI solutions.
5-7+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales, with at least 3+ years in a leadership capacity.
Experience developing frameworks for how SEs partner with Sales, Product, and Engineering to deliver impact efficiently across accounts.
History of establishing metrics and systems that measure SE impact on pipeline health, win rates, and customer adoption.
Track record of leading presales processes and supporting enterprise and strategic sales cycles from discovery through close.
Ability to translate customer business problems into Sierra’s technical solutions and clearly communicate to both technical and non-technical stakeholders across complex organizations.
Experience building Sales Engineering orgs in emerging categories (e.g., AI, data, security).
Comfort with workflows, AI and ML concepts, APIs/webhooks, and JSON.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Scale The Function: Lead, coach, and develop a high-caliber SE team, providing guidance, assigning projects and ensuring technical excellence. Conduct regular performance evaluations, foster professional growth, and coach team members to reach their full potential.\n\n - Player-Coach: Be a true player-coach who stays in the work: own your own enterprise deals as an individual contributor, running discovery, demos, and technical deep dives alongside your team, while leading and growing a team of high-growth enterprise SEs. Set the bar by example, jump into the most strategic cycles, and turn what you learn in the field into coaching and playbooks that raise the whole team. As the team grows, become a strategic leader and more manager focused.\n\n - GTM Technical Expert: Guide your team in designing and delivering compelling technical demos and proofs of concept for Sierra’s platform, providing technical solutions to customer challenges, and addressing technical questions throughout the sales cycle.\n\n - Cross-Functional Work: Partner closely with Sales, Product, and Agent Engineering teams to define best practices, playbooks, and repeatable processes that enable your team and partnership to scale beyond 1:1 customer interactions.\n\n - Lead & Support Customers: Act as a technical leader in early-stage customer conversations, helping your team understand, anticipate, and solve customer needs to advance Sierra’s industry-leading AI solutions.\n\n\nWHAT YOU'LL BRING\n\n - 5-7+ years of experience in Sales Engineering, Solutions Engineering, or customer-facing technical sales, with at least 3+ years in a leadership capacity.\n\n - Experience developing frameworks for how SEs partner with Sales, Product, and Engineering to deliver impact efficiently across accounts.\n\n - History of establishing metrics and systems that measure SE impact on pipeline health, win rates, and customer adoption.\n\n - Track record of leading presales processes and supporting enterprise and strategic sales cycles from discovery through close.\n\n - Ability to translate customer business problems into Sierra’s technical solutions and clearly communicate to both technical and non-technical stakeholders across complex organizations.\n\n\nEVEN BETTER\n\n - Experience building Sales Engineering orgs in emerging categories (e.g., AI, data, security).\n\n - Comfort with workflows, AI and ML concepts, APIs/webhooks, and JSON.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"df132d37-cb0d-47fc-bed9-560a284bf7c7","title":"Sales Compensation Systems","department":"Operations","team":"GTM Operations","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-13T14:26:15.496+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/df132d37-cb0d-47fc-bed9-560a284bf7c7","applyUrl":"https://jobs.ashbyhq.com/sierra/df132d37-cb0d-47fc-bed9-560a284bf7c7/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Own the commission platform end to end, including plan configuration, crediting rules, user access, and changes each plan year.
Build and maintain the data flows between Salesforce, the commission tool, HRIS and payroll so that bookings, roster changes and payouts stay in sync.
Turn new plan designs, deal types and SPIFs into working system logic, and test them before they go live.
Automate manual steps, build self-serve dashboards on attainment and payout cost for reps and leaders, and keep clear documentation for every rule and process.
Partner with Accounting on monthly close: deliver commission accruals, reconcile commissionable bookings to billing and revenue, and support commission capitalization.
Keep employee changes (hires, transfers, leaves, and exits) accurate in the commission system, and manage role-based access so pay data stays confidential.
5+ years in sales compensation systems, commissions operations, or a related RevOps or finance systems role.
Hands-on experience administering a sales compensation platform such as CaptivateIQ, Xactly, Spiff or Varicent, including building plans and calculation logic from scratch.
Strong Salesforce knowledge: objects, fields, reports, and how opportunity and booking data flows into commission calculations.
Working knowledge of commission accounting, including accruals, month-end close, and reconciling payouts to the general ledger.
Experience integrating an HRIS (e.g., Workday) with a commission platform, and sound judgment handling sensitive employee and pay data.
Experience managing a commission platform at a fast-growing company.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU'LL DO\n\n - Own the commission platform end to end, including plan configuration, crediting rules, user access, and changes each plan year.\n\n - Build and maintain the data flows between Salesforce, the commission tool, HRIS and payroll so that bookings, roster changes and payouts stay in sync.\n\n - Turn new plan designs, deal types and SPIFs into working system logic, and test them before they go live.\n\n - Automate manual steps, build self-serve dashboards on attainment and payout cost for reps and leaders, and keep clear documentation for every rule and process.\n\n - Partner with Accounting on monthly close: deliver commission accruals, reconcile commissionable bookings to billing and revenue, and support commission capitalization.\n\n - Keep employee changes (hires, transfers, leaves, and exits) accurate in the commission system, and manage role-based access so pay data stays confidential.\n\n\nWHAT YOU'LL BRING\n\n - 5+ years in sales compensation systems, commissions operations, or a related RevOps or finance systems role.\n\n - Hands-on experience administering a sales compensation platform such as CaptivateIQ, Xactly, Spiff or Varicent, including building plans and calculation logic from scratch.\n\n - Strong Salesforce knowledge: objects, fields, reports, and how opportunity and booking data flows into commission calculations.\n\n - Working knowledge of commission accounting, including accruals, month-end close, and reconciling payouts to the general ledger.\n\n - Experience integrating an HRIS (e.g., Workday) with a commission platform, and sound judgment handling sensitive employee and pay data.\n\n\nEVEN BETTER...\n\n - Experience managing a commission platform at a fast-growing company.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"14ec93a4-a7f7-4afe-8e45-dc9dfaad68b0","title":"People Programs ","department":"Operations","team":"HR","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-12T19:34:21.880+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/14ec93a4-a7f7-4afe-8e45-dc9dfaad68b0","applyUrl":"https://jobs.ashbyhq.com/sierra/14ec93a4-a7f7-4afe-8e45-dc9dfaad68b0/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
At Sierra, we are building a fast-scaling, mission-driven AI company where people are at the center of everything we do. As our People Programs Manager, you will design, build, and operationalize the programs and processes that shape the employee experience across Sierra globally. You’ll play a critical role in helping us create clarity, alignment, and belonging as we grow — ensuring Sierra remains a world-class place to work.
Support the design, launch, and execution of Sierra’s core people programs including onboarding, manager training, targeted development initiatives, and more. You’ll build scalable, repeatable processes to strengthen existing programs and be part of the development and launch of new programs such as feedback, performance, engagement, recognition, and more.
Partner closely with HR, Legal, Finance, and business leaders on company-wide people programs, ensuring all programs meet the needs of the business and are executed with operational excellence and compliance.
Advise and support employees and leaders by providing clear guidance on people policies, programs, and best practices, backed by strong documentation and communication.
Use data and insights to measure, iterate, and evolve programs, while staying ahead of trends in People Ops and employee experience.
5+ years of experience in People Programs, People Operations, or a related people-focused function within high-growth environments.
Experience designing and scaling people programs across the employee lifecycle in fast-moving, global technology companies.
Strong communication and relationship-building skills — able to partner effectively with executives, managers, and cross-functional teams.
Exceptional program and project management capability, with the ability to drive complex initiatives from concept to execution.
Analytical and systems-thinking mindset, comfortable using data, tooling, and process design to improve operational efficiency.
A passion for building clarity, culture, and connection in a rapidly evolving startup environment.
Experience supporting or designing programs for global teams across multiple regions.
Familiarity with HR tools and platforms (HRIS, onboarding systems, performance tools, etc.).
Background in organizational development, employee experience, or Learning & Development.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nWHAT YOU’LL DO\n\nAt Sierra, we are building a fast-scaling, mission-driven AI company where people are at the center of everything we do. As our People Programs Manager, you will design, build, and operationalize the programs and processes that shape the employee experience across Sierra globally. You’ll play a critical role in helping us create clarity, alignment, and belonging as we grow — ensuring Sierra remains a world-class place to work.\n\n - Support the design, launch, and execution of Sierra’s core people programs including onboarding, manager training, targeted development initiatives, and more. You’ll build scalable, repeatable processes to strengthen existing programs and be part of the development and launch of new programs such as feedback, performance, engagement, recognition, and more. \n\n - Partner closely with HR, Legal, Finance, and business leaders on company-wide people programs, ensuring all programs meet the needs of the business and are executed with operational excellence and compliance.\n\n - Advise and support employees and leaders by providing clear guidance on people policies, programs, and best practices, backed by strong documentation and communication.\n\n - Use data and insights to measure, iterate, and evolve programs, while staying ahead of trends in People Ops and employee experience.\n\n\nWHAT YOU’LL BRING\n\n - 5+ years of experience in People Programs, People Operations, or a related people-focused function within high-growth environments.\n\n - Experience designing and scaling people programs across the employee lifecycle in fast-moving, global technology companies.\n\n - Strong communication and relationship-building skills — able to partner effectively with executives, managers, and cross-functional teams.\n\n - Exceptional program and project management capability, with the ability to drive complex initiatives from concept to execution.\n\n - Analytical and systems-thinking mindset, comfortable using data, tooling, and process design to improve operational efficiency.\n\n - A passion for building clarity, culture, and connection in a rapidly evolving startup environment.\n\n\nEVEN BETTER…\n\n - Experience supporting or designing programs for global teams across multiple regions.\n\n - Familiarity with HR tools and platforms (HRIS, onboarding systems, performance tools, etc.).\n\n - Background in organizational development, employee experience, or Learning & Development.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."},{"id":"be3dd739-0584-4d15-90ff-dea66bfdbc72","title":"Integrated Marketing Lead","department":"Marketing & Communications","team":"Marketing","employmentType":"FullTime","location":"San Francisco, CA","secondaryLocations":[],"publishedAt":"2026-10-14T16:27:24.328+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"CA","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/sierra/be3dd739-0584-4d15-90ff-dea66bfdbc72","applyUrl":"https://jobs.ashbyhq.com/sierra/be3dd739-0584-4d15-90ff-dea66bfdbc72/application","descriptionHtml":"Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
Sierra is hiring an Integrated Marketing Lead to build and lead the function that turns our business priorities into measurable, integrated marketing programs. You will own the global campaign portfolio across digital and offline channels and account-based programs, with responsibility for creating pipeline, accelerating priority opportunities, and supporting expansion within existing customers.
This is a builder role for a leader who’s excited to roll up their sleeves, set global strategy, establish a scalable operating model, develop a strong team, and maintain a high bar for craft and execution. You will partner closely with Sales, Marketing Operations, Product Marketing, Brand, Events, Communications, and regional Marketing leaders.
What You'll Do:
Drive our campaign strategy: Build an integrated, full-funnel campaign portfolio spanning paid media, organic search, web, email, content, social, OOH, print, and account-based programs. Give every program a clear audience, message, channel role, and business objective.
Turn business priorities into pipeline: Translate company priorities by account, vertical, buyer, and region into programs that support acquisition, deal acceleration, and customer expansion. Balance always-on programs with launches and high-impact market moments.
Build Sierra’s named-account motion: Orchestrate always-on account-based marketing for Sierra’s highest-priority accounts.
Own investment and performance: Set pipeline targets, manage budgets, and determine the right channel and program mix. Partner with our operations team on attribution, forecasting, reporting, and lead flow. Use performance data to scale what works, stop what does not, and reallocate investment quickly.
Set the standard for execution: Establish clear campaign planning, briefing, quality assurance, launch, and optimization rhythms. Inspect high-impact work personally and ensure Sales has the messaging, assets, and follow-up needed to convert engagement into opportunities.
Build and lead the team: Hire, coach, and develop a high-performing team of digital marketing and campaigns professionals. Establish clear ownership, strong operating rhythms, and a culture of accountability, experimentation, and continuous improvement.
Use AI to multiply impact: Embed AI and automation across research, audience development, content adaptation, experimentation, and reporting. Increase the team’s speed and reach while maintaining human judgment, accuracy, and brand quality.
You’ll partner closely with Sales, Operations and Agent Development to turn account, vertical, and regional priorities into measurable programs and shared goals — as well as the entire Marketing team to drive awareness, credibility and pipeline. You’ll also partner with Finance on investment planning and with executive leaders on priorities, performance, and tradeoffs. Together, these teams will create a coordinated buyer journey from first engagement through opportunity progression and customer expansion.
12+ years of digital marketing, integrated campaigns, or demand generation experience.
A proven record of building and leading teams responsible for pipeline targets, substantial marketing investments, and global campaign portfolios.
Deep experience with complex, sales-led enterprise motions, including named accounts, long sales cycles, multi-stakeholder buying committees, and both new-logo and expansion programs.
Experience creating global strategies that allow for meaningful regional and market-level adaptation.
Strong data fluency, including attribution, forecasting, experimentation, funnel analysis, and translating performance into clear investment recommendations.
The ability to move between executive-level strategy and detailed campaign decisions without losing speed or quality.
Strong cross-functional leadership and executive communication skills, especially across Sales, Operations, Finance, and Marketing.
Practical fluency with AI-powered marketing tools and sound judgment about where automation improves performance and where human expertise remains essential.
Experience building an integrated marketing function at a fast growing enterprise SaaS or AI company.
A track record of creating industry specific campaigns that engage senior executives and drive measurable pipeline within priority accounts.
Experience expanding marketing programs internationally, with a strong understanding of how buyer needs, messaging, and channels vary across markets.
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.
We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
","descriptionPlain":"ABOUT US\n\nSierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia.\n\nWe are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do.\n\nOur co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.\n\n\nABOUT THE ROLE\n\nSierra is hiring an Integrated Marketing Lead to build and lead the function that turns our business priorities into measurable, integrated marketing programs. You will own the global campaign portfolio across digital and offline channels and account-based programs, with responsibility for creating pipeline, accelerating priority opportunities, and supporting expansion within existing customers.\n\nThis is a builder role for a leader who’s excited to roll up their sleeves, set global strategy, establish a scalable operating model, develop a strong team, and maintain a high bar for craft and execution. You will partner closely with Sales, Marketing Operations, Product Marketing, Brand, Events, Communications, and regional Marketing leaders.\n\n\nWhat You'll Do:\n\n - Drive our campaign strategy: Build an integrated, full-funnel campaign portfolio spanning paid media, organic search, web, email, content, social, OOH, print, and account-based programs. Give every program a clear audience, message, channel role, and business objective.\n\n - Turn business priorities into pipeline: Translate company priorities by account, vertical, buyer, and region into programs that support acquisition, deal acceleration, and customer expansion. Balance always-on programs with launches and high-impact market moments.\n\n - Build Sierra’s named-account motion: Orchestrate always-on account-based marketing for Sierra’s highest-priority accounts.\n\n - Own investment and performance: Set pipeline targets, manage budgets, and determine the right channel and program mix. Partner with our operations team on attribution, forecasting, reporting, and lead flow. Use performance data to scale what works, stop what does not, and reallocate investment quickly.\n\n - Set the standard for execution: Establish clear campaign planning, briefing, quality assurance, launch, and optimization rhythms. Inspect high-impact work personally and ensure Sales has the messaging, assets, and follow-up needed to convert engagement into opportunities.\n\n - Build and lead the team: Hire, coach, and develop a high-performing team of digital marketing and campaigns professionals. Establish clear ownership, strong operating rhythms, and a culture of accountability, experimentation, and continuous improvement.\n\n - Use AI to multiply impact: Embed AI and automation across research, audience development, content adaptation, experimentation, and reporting. Increase the team’s speed and reach while maintaining human judgment, accuracy, and brand quality.\n\n\nWHO YOU’LL WORK WITH\n\nYou’ll partner closely with Sales, Operations and Agent Development to turn account, vertical, and regional priorities into measurable programs and shared goals — as well as the entire Marketing team to drive awareness, credibility and pipeline. You’ll also partner with Finance on investment planning and with executive leaders on priorities, performance, and tradeoffs. Together, these teams will create a coordinated buyer journey from first engagement through opportunity progression and customer expansion.\n\n\nWHAT YOU'LL BRING:\n\n - 12+ years of digital marketing, integrated campaigns, or demand generation experience.\n\n - A proven record of building and leading teams responsible for pipeline targets, substantial marketing investments, and global campaign portfolios.\n\n - Deep experience with complex, sales-led enterprise motions, including named accounts, long sales cycles, multi-stakeholder buying committees, and both new-logo and expansion programs.\n\n - Experience creating global strategies that allow for meaningful regional and market-level adaptation.\n\n - Strong data fluency, including attribution, forecasting, experimentation, funnel analysis, and translating performance into clear investment recommendations.\n\n - The ability to move between executive-level strategy and detailed campaign decisions without losing speed or quality.\n\n - Strong cross-functional leadership and executive communication skills, especially across Sales, Operations, Finance, and Marketing.\n\n - Practical fluency with AI-powered marketing tools and sound judgment about where automation improves performance and where human expertise remains essential.\n\n\nEVEN BETTER...\n\n - Experience building an integrated marketing function at a fast growing enterprise SaaS or AI company.\n\n - A track record of creating industry specific campaigns that engage senior executives and drive measurable pipeline within priority accounts.\n\n - Experience expanding marketing programs internationally, with a strong understanding of how buyer needs, messaging, and channels vary across markets.\n\n\nOUR VALUES\n\n - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.\n\n - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.\n\n - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.\n\n - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.\n\n - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.\n\n\nWHAT WE OFFER\n\nWe want our benefits to reflect our values and offer the following to full-time employees:\n\n - Flexible (unlimited) paid time off\n\n - Medical, dental, and vision benefits for you and your family\n\n - Life insurance and disability benefits\n\n - Retirement plan dependent on country of employment\n\n - Parental leave\n\n - Fertility and family building benefits through Carrot\n\n - Lunch, as well as delicious snacks and coffee to keep you energized \n\n - Discretionary benefit stipend giving people the ability to spend where it matters most\n\n - Free alphorn lessons\n\nThese benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies.\n\n\nBE YOU, WITH US\n\nWe're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class."}],"apiVersion":"1"}