Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply.
We are building our own platform, and have built our own coding agent Friday, which powers the majority of how we deliver. We're bootstrapped, cash-flow positive, and growing fast.
Engineers who thrive at Headstart are builders who want to understand both how businesses and code works. We take the work seriously and the culture deliberately. Pay is transparent, weekends are yours, and we don't confuse long hours with good work.
Operate as technical lead on complex and ambiguous client engagements end-to-end, from ideation and discovery through to production
Be the technical authority in sales and scoping conversations: lead with clear recommendations, drive technical strategy forward, and keep the conversation focused on accomplishing engagement goals
Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like
Build 0 -> 1 rapidly while ensuring long-term reliability, maintainability, and security
Balance multiple concurrent engagements, context-switching between different technical stacks and business domains
Contribute to the Headstart Platform by identifying and delivering high leverage investments across our tooling and infrastructure
Grow the engineers around you and act as player-coach to raise the floor of every project you work on
7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end
Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly
Communicates with structure: you answer the question that was asked, get to the point quickly, and can go deeper when someone asks without losing the thread
Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told
Have designed and shipped agentic systems to solve complex user challenges, and know when to lean on deterministic solutions
Enjoys a fast-paced, transparent, and collaborative environment
Proven full-stack depth: backend services (Python), datastores, React/Next.js, optionally ML
Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale
Bonus if you’ve been a founding engineer or startup early hire, with history building production products from scratch
Initial screen (30 min): a conversation with our recruiting partner about your background, what you're looking for, and how we work.
Technical screen (30 min): a short, real-world coding exercise with an engineer from our team.
Hiring manager interview (45 min): behavioral and past work with a member of the team. We also look at how clearly and concisely you communicate, since it’s a core part of client work.
Technical interviews (2.5 hrs total, split across two sessions): a coding interview and a systems design interview. You're encouraged to use AI tools in the coding interview; it reflects how we work day to day.
Project deep dive (1 hr): for Staff candidates only. A conversation with a fellow engineer about something significant you've built.
This role offers extensive benefits, including:
a base salary of $265,000 USD
competitive equity compensation
401k with 4.5% employer match
fully covered medical, dental, and vision premiums
monthly wellness stipend
Citi Bike + pre-tax commuter benefits
12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.
If you’re NYC based — we have a loft office in Soho and provide lunch and snacks
While this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada.
Note: Even if you don't meet all the requirements, we still encourage you to apply.
","descriptionPlain":"ABOUT THE COMPANY\n\nHeadstart https://www.headstart.nyc/ is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply.\n\nWe are building our own platform, and have built our own coding agent Friday, which powers the majority of how we deliver. We're bootstrapped, cash-flow positive, and growing fast.\n\n \n\n\nWHY JOIN US\n\nEngineers who thrive at Headstart are builders who want to understand both how businesses and code works. We take the work seriously and the culture deliberately. Pay is transparent, weekends are yours, and we don't confuse long hours with good work.\n\n\n\n\nABOUT THE ROLE\n\n - Operate as technical lead on complex and ambiguous client engagements end-to-end, from ideation and discovery through to production\n\n - Be the technical authority in sales and scoping conversations: lead with clear recommendations, drive technical strategy forward, and keep the conversation focused on accomplishing engagement goals \n\n - Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like\n\n - Build 0 -> 1 rapidly while ensuring long-term reliability, maintainability, and security\n\n - Balance multiple concurrent engagements, context-switching between different technical stacks and business domains\n\n - Contribute to the Headstart Platform by identifying and delivering high leverage investments across our tooling and infrastructure\n\n - Grow the engineers around you and act as player-coach to raise the floor of every project you work on\n \n \n\n\nYOUR BACKGROUND\n\n - 7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end\n\n - Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly\n\n - Communicates with structure: you answer the question that was asked, get to the point quickly, and can go deeper when someone asks without losing the thread\n\n - Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told\n\n - Have designed and shipped agentic systems to solve complex user challenges, and know when to lean on deterministic solutions\n\n - Enjoys a fast-paced, transparent, and collaborative environment\n\n - Proven full-stack depth: backend services (Python), datastores, React/Next.js, optionally ML\n\n - Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale\n\n - Bonus if you’ve been a founding engineer or startup early hire, with history building production products from scratch\n\n\n\n\nWHAT TO EXPECT\n\n 1. Initial screen (30 min): a conversation with our recruiting partner about your background, what you're looking for, and how we work.\n\n 2. Technical screen (30 min): a short, real-world coding exercise with an engineer from our team.\n\n 3. Hiring manager interview (45 min): behavioral and past work with a member of the team. We also look at how clearly and concisely you communicate, since it’s a core part of client work.\n\n 4. Technical interviews (2.5 hrs total, split across two sessions): a coding interview and a systems design interview. You're encouraged to use AI tools in the coding interview; it reflects how we work day to day.\n\n 5. Project deep dive (1 hr): for Staff candidates only. A conversation with a fellow engineer about something significant you've built.\n\n\n\n\nWHAT WE OFFER\n\nThis role offers extensive benefits, including:\n\n - a base salary of $265,000 USD \n\n - competitive equity compensation\n\n - 401k with 4.5% employer match\n\n - fully covered medical, dental, and vision premiums\n\n - monthly wellness stipend\n\n - Citi Bike + pre-tax commuter benefits\n\n - 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.\n\nIf you’re NYC based — we have a loft office in Soho and provide lunch and snacks\n\nWhile this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada.\n\n\n\nNote: Even if you don't meet all the requirements, we still encourage you to apply. \n\n\n\n"},{"id":"5890a597-f72d-4968-9a54-397bff0c0c9b","title":"Staff Product Manager","department":"Product","team":"Product","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[],"publishedAt":"2026-03-12T16:07:29.300+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York City"}},"jobUrl":"https://jobs.ashbyhq.com/Headstart/5890a597-f72d-4968-9a54-397bff0c0c9b","applyUrl":"https://jobs.ashbyhq.com/Headstart/5890a597-f72d-4968-9a54-397bff0c0c9b/application","descriptionHtml":"At Headstart our mission is to bring companies into the age of intelligence and automate software development. We are the team behind the coding agent Friday and are building frontier applied AI technologies including agent orchestration, memory, and more.
We specialize in solving problems with the latest LLM capabilities that deliver measurable outcomes and breakthrough results for organizations in many different industries. As the technology continues to advance at an unprecedented rate, we provide companies with custom software solutions and a suite of tools to stay ahead of the intelligence curve.
We are a lean, high-velocity team that ships breakthrough AI capabilities at startup speed. We work directly with our users, iterate rapidly, and measure success by the real-world impact we create for our clients. We believe that simplicity and product fundamentals are more important than ever in an AI driven world.
Lead product strategy and execution across complex enterprise engagements, from discovery through multi-SOW roadmaps and long-term platform vision.
Shape Headstart's cross-client product strategy by identifying patterns, building reusable frameworks, and scaling AI product delivery.
Own AI product quality end-to-end, defining success metrics, evaluation frameworks, guardrails, and production-readiness standards alongside engineering and leadership.
Turn delivery learnings into internal product IP, including telemetry standards, analytics boilerplates, and agentic curriculum.
Navigate complex stakeholder dynamics, build executive relationships, drive SOW expansion, and push back when it improves outcomes.
Lead 0→1 validation of AI products through rapid prototyping and fast iteration, advising senior client leaders on AI operating models and translating technical tradeoffs into business outcomes.
8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML, with a track record owning multi-phase, multi-stakeholder engagements from scoping through production.
Platform-level operator who builds frameworks, standards, and reusable IP that outlast individual engagements.
Comfortable working in AI/ML systems, including agent architectures, retrieval, evaluation pipelines, observability, LLM behavior, and the tradeoffs around model choice, latency, cost, and safety.
Strong judgment for AI product quality and readiness, with a track record defining success metrics and measurable business outcomes, not just shipping features.
Exceptional writing skills, producing clear, durable strategy docs, client specs, and internal frameworks.
Comfortable advising senior client leaders on AI operating models, investment priorities, and change management, translating technical complexity into business decisions.
Note: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $265,000 USD plus competitive equity compensation, 401k with employer match, fully covered medical, dental, and vision premiums, monthly wellness stipend, free lunch everyday in our NYC office, Citi Bike + pre-tax commuter benefits, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.
While this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada for the right fit.
","descriptionPlain":"ABOUT THE COMPANY\n\nAt Headstart our mission is to bring companies into the age of intelligence and automate software development. We are the team behind the coding agent Friday and are building frontier applied AI technologies including agent orchestration, memory, and more.\n\nWe specialize in solving problems with the latest LLM capabilities that deliver measurable outcomes and breakthrough results for organizations in many different industries. As the technology continues to advance at an unprecedented rate, we provide companies with custom software solutions and a suite of tools to stay ahead of the intelligence curve.\n\n\n\n\nABOUT THE TEAM\n\nWe are a lean, high-velocity team that ships breakthrough AI capabilities at startup speed. We work directly with our users, iterate rapidly, and measure success by the real-world impact we create for our clients. We believe that simplicity and product fundamentals are more important than ever in an AI driven world.\n\n\n\n\nABOUT THE ROLE\n\n - Lead product strategy and execution across complex enterprise engagements, from discovery through multi-SOW roadmaps and long-term platform vision.\n\n - Shape Headstart's cross-client product strategy by identifying patterns, building reusable frameworks, and scaling AI product delivery.\n\n - Own AI product quality end-to-end, defining success metrics, evaluation frameworks, guardrails, and production-readiness standards alongside engineering and leadership.\n\n - Turn delivery learnings into internal product IP, including telemetry standards, analytics boilerplates, and agentic curriculum.\n\n - Navigate complex stakeholder dynamics, build executive relationships, drive SOW expansion, and push back when it improves outcomes.\n\n - Lead 0→1 validation of AI products through rapid prototyping and fast iteration, advising senior client leaders on AI operating models and translating technical tradeoffs into business outcomes.\n\n\n\n\nYOUR BACKGROUND\n\n - 8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML, with a track record owning multi-phase, multi-stakeholder engagements from scoping through production.\n\n - Platform-level operator who builds frameworks, standards, and reusable IP that outlast individual engagements.\n\n - Comfortable working in AI/ML systems, including agent architectures, retrieval, evaluation pipelines, observability, LLM behavior, and the tradeoffs around model choice, latency, cost, and safety.\n\n - Strong judgment for AI product quality and readiness, with a track record defining success metrics and measurable business outcomes, not just shipping features.\n\n - Exceptional writing skills, producing clear, durable strategy docs, client specs, and internal frameworks.\n\n - Comfortable advising senior client leaders on AI operating models, investment priorities, and change management, translating technical complexity into business decisions.\n\n\n\nNote: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $265,000 USD plus competitive equity compensation, 401k with employer match, fully covered medical, dental, and vision premiums, monthly wellness stipend, free lunch everyday in our NYC office, Citi Bike + pre-tax commuter benefits, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.\n\nWhile this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada for the right fit."},{"id":"25dfc360-2b8e-4583-9acb-298b56cbe705","title":"Senior Engineering Manager, Applied AI","department":"Engineering","team":"Engineering","employmentType":"FullTime","location":"New York, NY","secondaryLocations":[{"location":"Toronto, Canada","address":{"postalAddress":{"addressRegion":"Ontario","addressCountry":"Canada","addressLocality":"Toronto"}}}],"publishedAt":"2026-09-29T22:16:03.830+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York City"}},"jobUrl":"https://jobs.ashbyhq.com/Headstart/25dfc360-2b8e-4583-9acb-298b56cbe705","applyUrl":"https://jobs.ashbyhq.com/Headstart/25dfc360-2b8e-4583-9acb-298b56cbe705/application","descriptionHtml":"Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.
Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room.
This role is part player, part coach, part staffing lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck. Then you'll build and lead a team and help shape the company as we grow.
Your team. Hold a high bar and grow each engineer through direct, actionable feedback. Develop senior engineers into staff. Give clear priorities and expectations without adding process before we understand the problem.
Technical leadership. Review architecture, agent prompts and structure, and eval design. Step into the hardest technical and client situations, like production regressions and unclear requirements, and make the call. Flag trouble early, while it's cheap to fix.
Closing the loop. Spot patterns across engagements and turn them into standing practice, reference implementations, and platform capabilities. Check that the next engagement is faster because of it.
Staffing. Shape who works on which engagement, plan transitions ahead, and flag risks before they reach a client.
Hiring. Run hiring for your team, from sourcing to onboarding. You define the bar.
Partnerships. Work closely with product, client partners, and client stakeholders so each engagement lands.
4+ years managing engineers and managers, including senior and staff, with real experience hiring and developing them.
8+ years in software engineering, deep enough to review designs and challenge the team's approach. Hands-on with Python.
Experience delivering software in real client environments and taking something from zero to one, whether a team, a practice, or a hiring process.
Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel. Fluent with AI coding tools. Depth matters more than prior title.
Bonus: Management experience in a consulting, services, or forward deployed engineering organization.
High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast.
We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves.
AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable.
Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view.
Breadth that compounds. You'll see more industries and problems in a year than most people see in a career.
Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.
Initial screen (30 min): with our recruiting partner.
Technical screen (30 min): a short, real-world coding exercise with an engineer.
Hiring manager interview (45 min): behavioral and past work.
Technical interviews (2.5 hrs, two sessions): coding and systems design. Use AI tools in the coding interview, since it reflects how we work.
Case study (75 min): a live, scenario-based discussion covering staffing, feedback, technical review, and closing the loop. No prep needed.
Base salary of $300,000 USD, plus competitive equity
401k with 4.5% employer match, and fully covered medical, dental, and vision premiums
Monthly wellness stipend, Citi Bike, and pre-tax commuter benefits
12 weeks parental leave, with an optional 4-week ramp-up at 50%
Loft office in Soho with lunch and snacks
Hybrid in NYC, and fully remote in the rest of the US and Canada.
Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.
Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room.
This role is part player, part coach, part staffing partner. Most of your time stays on a client engagement, hands-on, close to the work and to where engineers get stuck. You'll manage a group of engineers across a few engagements and grow with the team as we do.
Level: Reports to the Head of Engineering. You run a team inside our system: you apply the bar, keep your engineers growing, and stay close to the work.
Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead.
Technical leadership. Review architecture, agent, prompt, and eval design on your engagements. Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix.
Engagement delivery. Run the engagement-level relationship with clients and their stakeholders, alongside product and client partners, so each engagement lands.
Staffing. Manage transitions on your team, plan ahead, and flag risks before they reach a client. Escalate conflicts across engagements to the Head of Engineering.
Hiring. Interview, calibrate, close, and onboard new engineers against the bar the Head of Engineering sets.
Practice. Follow the team's practices and tell us what isn't working. Bring patterns you see to the wider team so they can become standing practice, and make sure your engineers use what exists.
3+ years managing engineers, with real experience giving feedback and developing people.
5+ years in software engineering, deep enough to review designs and challenge the team's approach. Hands-on with Python.
Experience delivering software in real client environments.
Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel. Fluent with AI coding tools. Depth matters more than prior title.
Bonus: management experience in a consulting, services, or forward deployed engineering organization, or experience taking a team or practice from zero to one.
High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast.
We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves.
AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable.
Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view.
Breadth that compounds. You'll see more industries and problems in a year than most people see in a career.
Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.
Initial screen (30 min): with our recruiting partner.
Technical screen (30 min): a short, real-world coding exercise with an engineer.
Hiring manager interview (45 min): behavioral and past work.
Technical interviews (2.5 hrs, two sessions): coding and systems design. Use AI tools in the coding interview, since it reflects how we work.
Case study (75 min): a live, scenario-based discussion covering staffing, feedback, technical review, and closing the loop. No prep needed.
Base salary of $285,000 USD plus competitive equity
401k with 4.5% employer match, and fully covered medical, dental, and vision premiums
Monthly wellness stipend, Citi Bike, and pre-tax commuter benefits
12 weeks parental leave, with an optional 4-week ramp-up at 50%
Loft office in Soho with lunch and snacks
Hybrid in NYC. We're open to fully remote candidates in the US or Canada.