Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
We’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.
You don’t need to have used every tool we use. What matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!
Design and develop web applications using modern frontend frameworks like Svelte
Build intuitive and user-friendly interfaces that delight users
Develop and maintain backend APIs using tools like FastAPI
Manage and optimize database systems like MongoDB
Collaborate with our ML research team to integrate AI experiences into our products
Proficiency in TypeScript or JavaScript
Experience with frontend frameworks such as React, Vue, or Svelte
Solid understanding of HTML and CSS
Hands-on experience building backend APIs
Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)
SvelteKit experience
Python proficiency and AI/ML framework exposure
Experience in creating AI-driven applications
Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)
Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows
Knowledge of secure coding practices and mitigating vulnerabilities in web applications
Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work
Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality
Understanding of AI safety principles or ethical considerations in AI systems
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You've learned things about your code only production traffic can teach
You're comfortable debugging across the stack – from browser devtools to database query plans.
You've worked in environments where moving fast matters and you know how to balance speed with sustainability.
You're interested in applying your security mindset to AI, where the threat model is still being written
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $180k-$220k plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.\n\nYou don’t need to have used every tool we use. What matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design and develop web applications using modern frontend frameworks like Svelte\n\n - Build intuitive and user-friendly interfaces that delight users\n\n - Develop and maintain backend APIs using tools like FastAPI\n\n - Manage and optimize database systems like MongoDB\n\n - Collaborate with our ML research team to integrate AI experiences into our products\n\n\n\n\nWHO YOU ARE:\n\n - Proficiency in TypeScript or JavaScript\n\n - Experience with frontend frameworks such as React, Vue, or Svelte\n\n - Solid understanding of HTML and CSS\n\n - Hands-on experience building backend APIs\n\n - Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - SvelteKit experience\n\n - Python proficiency and AI/ML framework exposure\n\n - Experience in creating AI-driven applications\n\n - Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)\n\n - Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows\n\n - Knowledge of secure coding practices and mitigating vulnerabilities in web applications\n\n - Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work\n\n - Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality\n\n - Understanding of AI safety principles or ethical considerations in AI systems\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You've learned things about your code only production traffic can teach\n\n - You're comfortable debugging across the stack – from browser devtools to database query plans.\n\n - You've worked in environments where moving fast matters and you know how to balance speed with sustainability.\n\n - You're interested in applying your security mindset to AI, where the threat model is still being written\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $180k-$220k plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application. "},{"id":"2edf0f4c-d356-41da-a7b8-9b54e95f140c","title":"Software Engineer ","department":"Software Engineering","team":"Software Engineering","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-01T19:43:22.852+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/2edf0f4c-d356-41da-a7b8-9b54e95f140c","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/2edf0f4c-d356-41da-a7b8-9b54e95f140c/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
We’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.
You don’t need to have used every tool we use– what matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!
Design and develop web applications using modern frontend frameworks like Svelte
Build intuitive and user-friendly interfaces that delight users
Develop and maintain backend APIs using tools like FastAPI
Manage and optimize database systems like MongoDB
Collaborate with our ML research team to integrate AI experiences into our products
Proficiency in TypeScript or JavaScript
Experience with frontend frameworks such as React, Vue, or Svelte
Solid understanding of HTML and CSS
Hands-on experience building backend APIs
Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)
SvelteKit experience
Python proficiency and AI/ML framework exposure
Experience in creating AI-driven applications
Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)
Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows
Knowledge of secure coding practices and mitigating vulnerabilities in web applications
Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work
Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality
Understanding of AI safety principles or ethical considerations in AI systems
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You've learned things about your code only production traffic can teach
You're comfortable debugging across the stack – from browser devtools to database query plans.
You've worked in environments where moving fast matters and you know how to balance speed with sustainability.
You're interested in applying your security mindset to AI, where the threat model is still being written
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Salary: $110k-185k plus performance based bonus
Equity: Competitive equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.\n\nYou don’t need to have used every tool we use– what matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design and develop web applications using modern frontend frameworks like Svelte\n\n - Build intuitive and user-friendly interfaces that delight users\n\n - Develop and maintain backend APIs using tools like FastAPI\n\n - Manage and optimize database systems like MongoDB\n\n - Collaborate with our ML research team to integrate AI experiences into our products\n\n\n\n\nWHO YOU ARE:\n\n - Proficiency in TypeScript or JavaScript\n\n - Experience with frontend frameworks such as React, Vue, or Svelte\n\n - Solid understanding of HTML and CSS\n\n - Hands-on experience building backend APIs\n\n - Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - SvelteKit experience\n\n - Python proficiency and AI/ML framework exposure\n\n - Experience in creating AI-driven applications\n\n - Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)\n\n - Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows\n\n - Knowledge of secure coding practices and mitigating vulnerabilities in web applications\n\n - Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work\n\n - Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality\n\n - Understanding of AI safety principles or ethical considerations in AI systems\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You've learned things about your code only production traffic can teach\n\n - You're comfortable debugging across the stack – from browser devtools to database query plans.\n\n - You've worked in environments where moving fast matters and you know how to balance speed with sustainability.\n\n - You're interested in applying your security mindset to AI, where the threat model is still being written\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nSalary: $110k-185k plus performance based bonus\n\nEquity: Competitive equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY:\n\nSubmit your resume, link to your portfolio, and answer the questions on the application. "},{"id":"09cf5387-81f0-4a40-a402-8a1d0c2b5cf0","title":"Senior Forward Deployed Engineer – Enterprise","department":"Forward Deployed","team":"Forward Deployed","employmentType":"FullTime","location":"San Francisco","secondaryLocations":[{"location":"Seattle","address":{"postalAddress":{"postalCode":"98101","addressRegion":"WA","addressCountry":"United States","addressLocality":"Seattle"}}}],"publishedAt":"2026-09-01T19:37:39.772+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"postalCode":"94108","addressRegion":"California","addressCountry":"United States","addressLocality":"San Francisco"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/09cf5387-81f0-4a40-a402-8a1d0c2b5cf0","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/09cf5387-81f0-4a40-a402-8a1d0c2b5cf0/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
As a Forward Deployed Engineer at Gray Swan, you’ll design, build, and deploy enterprise-grade software solutions directly inside customer environments. You’ll work hands-on with customer teams to integrate Gray Swan’s AI security platform into complex production systems, translating ambiguous, high-stakes requirements into reliable, scalable deployments.
This role is ideal for engineers who don’t want to work on the same narrow surface area every day. You’ll operate at the intersection of software engineering, systems integration, and customer delivery, partnering closely with customers, sales, product, and core engineering teams. You’ll own outcomes end-to-end and operate effectively in fast-moving, customer-facing environments where reliability, security, and trust matter.
Work directly with engineering, security, and platform teams to understand system architectures, constraints, and operational realities.
Design and implement integrations between Gray Swan’s platform and customer systems, APIs, data pipelines, and runtime environments.
Translate real-world enterprise requirements into well-scoped proofs of concept, deployment plans, and production architectures.
Act as the primary technical owner for customer deployments, rapidly identifying, scoping, and resolving issues across environments.
Build and extend backend services, integrations, and tooling to support secure deployment in diverse customer environments.
Ensure deployments meet enterprise expectations for reliability, security, observability, and maintainability.
Develop proofs of concept quickly to validate technical feasibility and customer value.
Iterate based on user feedback, operational learnings, and evolving requirements.
Balance speed with long-term maintainability and platform consistency.
Partner closely with sales, product, and core engineering teams to deliver successful customer outcomes.
Communicate technical findings, tradeoffs, and recommendations clearly to both internal teams and customers.
Hands-on experience building and deploying production-grade software systems.
Strong background in backend or full-stack software engineering, with experience designing APIs, services, and integrations.
Familiarity with cloud-native architectures and distributed systems, including AWS, GCP, or Azure.
Experience working in ambiguous, fast-moving environments and taking full ownership of outcomes.
Comfort working directly with customers and external stakeholders on technical delivery.
Strong programming experience in Python and at least one systems or backend-oriented language (e.g., Go, Java, C++, Rust).
Experience working with data pipelines, event-driven systems, or service-oriented architectures.
Understanding of security fundamentals, such as authentication, authorization, monitoring, and secure system design.
Bachelor’s degree in Computer Science, Engineering, or a related technical field is required.
Experience deploying or integrating enterprise software into customer environments.
Background in security, infrastructure, or platform engineering.
Familiarity with AI systems, ML-enabled products, or AI security concepts (not required to build models).
Experience in forward-deployed engineering, technical consulting, technical pre-sales, or customer-facing engineering roles.
Strong collaboration and problem-solving skills, especially in high-stakes customer contexts.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Want a role with real ownership and responsibility from day one.
Enjoy solving hard, ambiguous problems with customers.
Learn quickly and are naturally curious.
Care deeply about building reliable, secure systems that matter.
Are motivated by Gray Swan’s mission to help the world use AI safely and securely.
A competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Salary: $175,000-220,000 a competitive equity package in a startup with real revenue and globally recognized customers
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nAs a Forward Deployed Engineer at Gray Swan, you’ll design, build, and deploy enterprise-grade software solutions directly inside customer environments. You’ll work hands-on with customer teams to integrate Gray Swan’s AI security platform into complex production systems, translating ambiguous, high-stakes requirements into reliable, scalable deployments.\n\nThis role is ideal for engineers who don’t want to work on the same narrow surface area every day. You’ll operate at the intersection of software engineering, systems integration, and customer delivery, partnering closely with customers, sales, product, and core engineering teams. You’ll own outcomes end-to-end and operate effectively in fast-moving, customer-facing environments where reliability, security, and trust matter.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Work directly with engineering, security, and platform teams to understand system architectures, constraints, and operational realities.\n\n - Design and implement integrations between Gray Swan’s platform and customer systems, APIs, data pipelines, and runtime environments.\n\n - Translate real-world enterprise requirements into well-scoped proofs of concept, deployment plans, and production architectures.\n\n - Act as the primary technical owner for customer deployments, rapidly identifying, scoping, and resolving issues across environments.\n\n - Build and extend backend services, integrations, and tooling to support secure deployment in diverse customer environments.\n\n - Ensure deployments meet enterprise expectations for reliability, security, observability, and maintainability.\n\n - Develop proofs of concept quickly to validate technical feasibility and customer value.\n\n - Iterate based on user feedback, operational learnings, and evolving requirements.\n\n - Balance speed with long-term maintainability and platform consistency.\n\n - Partner closely with sales, product, and core engineering teams to deliver successful customer outcomes.\n\n - Communicate technical findings, tradeoffs, and recommendations clearly to both internal teams and customers.\n\n\nWHAT YOU BRING:\n\n - Hands-on experience building and deploying production-grade software systems.\n\n - Strong background in backend or full-stack software engineering, with experience designing APIs, services, and integrations.\n\n - Familiarity with cloud-native architectures and distributed systems, including AWS, GCP, or Azure.\n\n - Experience working in ambiguous, fast-moving environments and taking full ownership of outcomes.\n\n - Comfort working directly with customers and external stakeholders on technical delivery.\n\n - Strong programming experience in Python and at least one systems or backend-oriented language (e.g., Go, Java, C++, Rust).\n\n - Experience working with data pipelines, event-driven systems, or service-oriented architectures.\n\n - Understanding of security fundamentals, such as authentication, authorization, monitoring, and secure system design.\n\n - Bachelor’s degree in Computer Science, Engineering, or a related technical field is required.\n \n \n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience deploying or integrating enterprise software into customer environments.\n\n - Background in security, infrastructure, or platform engineering.\n\n - Familiarity with AI systems, ML-enabled products, or AI security concepts (not required to build models).\n\n - Experience in forward-deployed engineering, technical consulting, technical pre-sales, or customer-facing engineering roles.\n\n - Strong collaboration and problem-solving skills, especially in high-stakes customer contexts.\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Want a role with real ownership and responsibility from day one.\n\n - Enjoy solving hard, ambiguous problems with customers.\n\n - Learn quickly and are naturally curious.\n\n - Care deeply about building reliable, secure systems that matter.\n\n - Are motivated by Gray Swan’s mission to help the world use AI safely and securely.\n\n\n\n\nWHAT WE OFFER:\n\nA competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nSalary: $175,000-220,000 a competitive equity package in a startup with real revenue and globally recognized customers\n\n\n\n\nBENEFITS:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nINTERVIEW PROCESS:\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"23c94780-c876-4bf6-8d1e-09dc6156b274","title":"Senior Account Executive – AI Security","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[{"location":"Philadelphia","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Philadelphia"}}},{"location":"Seattle","address":{"postalAddress":{"postalCode":"98101","addressRegion":"WA","addressCountry":"United States","addressLocality":"Seattle"}}},{"location":"San Francisco","address":{"postalAddress":{"postalCode":"94108","addressRegion":"California","addressCountry":"United States","addressLocality":"San Francisco"}}},{"location":"New York City","address":{"postalAddress":{"addressRegion":"New York","addressCountry":"United States","addressLocality":"New York City"}}},{"location":"Remote (U.S. Only)","address":{"postalAddress":{"addressCountry":"United States"}}},{"location":"Boston","address":{"postalAddress":{"addressRegion":"Massachusetts","addressCountry":"United States","addressLocality":"Boston"}}}],"publishedAt":"2026-09-01T19:42:17.481+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/23c94780-c876-4bf6-8d1e-09dc6156b274","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/23c94780-c876-4bf6-8d1e-09dc6156b274/application","descriptionHtml":"About Gray Swan
Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
As an Account Executive at Gray Swan AI, you’ll own enterprise sales cycles end-to-end for a highly technical AI safety and security platform. This is not a replacement-level software sales role. We’re looking for someone who can operate credibly with technical buyers, learn complex products quickly, and thrive in a fast-moving startup environment where ownership and initiative matter.
You’ll work closely with founders, engineering, and product to turn inbound interest into paid pilots and long-term production deployments. This role blends enterprise selling, technical curiosity, and startup hustle, with significant autonomy and upside.
If you’re energized by building something early, working hard, and closing meaningful six-figure deals in a new and rapidly evolving market, this role is likely a great fit.
Own the full sales cycle from first conversation through close, often starting with paid pilots and expanding to production deployments.
Sell a complete AI safety and security platform, including automated adversarial testing/ red teaming and runtime defensive solutions for AI systems.
Build credibility with technical and executive stakeholders across AI, security, and engineering teams.
Learn and communicate technical concepts clearly, working closely with internal technical teams to scope solutions and answer customer questions.
Engage buyers in regulated and high-stakes industries such as financial services, healthcare, and insurance.
Generate pipeline through a mix of inbound leads, conference networking, referrals, and outbound efforts.
Maintain strong momentum through long, multi-stakeholder sales processes.
Work directly with founders, product, and engineering to shape customer pilots and deployments. Provide feedback from the field to influence product direction, positioning, and go-to-market strategy.
Proven experience selling enterprise software or platforms, ideally in AI, security, or adjacent technical domains.
Comfort learning technical material and engaging with technical buyers, even if you are not an engineer by training.
Experience selling into or having strong relationships within AI, security, financial services, healthcare, or insurance organizations.
Ability to operate independently, generate pipeline, and own outcomes end-to-end.
Ability to thrive in early-stage startup environments, comfortable wearing multiple hats, and contributing beyond a narrowly defined sales role.
Highly motivated, disciplined, and willing to work hard to build something meaningful.
Presence, credibility, and sound judgment to customer interactions.
Prior experience selling highly technical or emerging technology products.
Existing relationships with AI labs, security teams, or enterprise engineering organizations.
Experience closing six-figure enterprise deals with long, consultative sales cycles.
Familiarity with AI safety, security, testing, or infrastructure-level software.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Want to help define how enterprise AI safety and security software is sold.
Enjoy learning complex products and explaining them clearly to customers.
Are motivated by ownership, accountability, and upside rather than rigid structure.
Are excited by Gray Swan’s mission to help organizations deploy AI safely and securely.
A competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Base salary is targeted to $157k-$192k + commission ($314-$384k OTE)
Meaningful equity participation
Work from our office in Pittsburgh, or remotely
Opportunity for outsized earnings driven by high inbound interest and large deal sizes
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"About Gray Swan\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nAs an Account Executive at Gray Swan AI, you’ll own enterprise sales cycles end-to-end for a highly technical AI safety and security platform. This is not a replacement-level software sales role. We’re looking for someone who can operate credibly with technical buyers, learn complex products quickly, and thrive in a fast-moving startup environment where ownership and initiative matter.\n\nYou’ll work closely with founders, engineering, and product to turn inbound interest into paid pilots and long-term production deployments. This role blends enterprise selling, technical curiosity, and startup hustle, with significant autonomy and upside.\n\nIf you’re energized by building something early, working hard, and closing meaningful six-figure deals in a new and rapidly evolving market, this role is likely a great fit.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Own the full sales cycle from first conversation through close, often starting with paid pilots and expanding to production deployments.\n\n - Sell a complete AI safety and security platform, including automated adversarial testing/ red teaming and runtime defensive solutions for AI systems.\n\n - Build credibility with technical and executive stakeholders across AI, security, and engineering teams.\n\n - Learn and communicate technical concepts clearly, working closely with internal technical teams to scope solutions and answer customer questions.\n\n - Engage buyers in regulated and high-stakes industries such as financial services, healthcare, and insurance.\n\n - Generate pipeline through a mix of inbound leads, conference networking, referrals, and outbound efforts.\n\n - Maintain strong momentum through long, multi-stakeholder sales processes.\n\n - Work directly with founders, product, and engineering to shape customer pilots and deployments. Provide feedback from the field to influence product direction, positioning, and go-to-market strategy.\n\n\n\n\nWHAT YOU BRING:\n\n - Proven experience selling enterprise software or platforms, ideally in AI, security, or adjacent technical domains.\n\n - Comfort learning technical material and engaging with technical buyers, even if you are not an engineer by training.\n\n - Experience selling into or having strong relationships within AI, security, financial services, healthcare, or insurance organizations.\n\n - Ability to operate independently, generate pipeline, and own outcomes end-to-end.\n\n - Ability to thrive in early-stage startup environments, comfortable wearing multiple hats, and contributing beyond a narrowly defined sales role.\n\n - Highly motivated, disciplined, and willing to work hard to build something meaningful.\n\n - Presence, credibility, and sound judgment to customer interactions.\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Prior experience selling highly technical or emerging technology products.\n\n - Existing relationships with AI labs, security teams, or enterprise engineering organizations.\n\n - Experience closing six-figure enterprise deals with long, consultative sales cycles.\n\n - Familiarity with AI safety, security, testing, or infrastructure-level software.\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Want to help define how enterprise AI safety and security software is sold.\n\n - Enjoy learning complex products and explaining them clearly to customers.\n\n - Are motivated by ownership, accountability, and upside rather than rigid structure.\n\n - Are excited by Gray Swan’s mission to help organizations deploy AI safely and securely.\n\n\n\n\nWHAT WE OFFER:\n\nA competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\n - Base salary is targeted to $157k-$192k + commission ($314-$384k OTE)\n\n - Meaningful equity participation\n\n - Work from our office in Pittsburgh, or remotely\n\n - Opportunity for outsized earnings driven by high inbound interest and large deal sizes\n\n\n\n\nBENEFITS:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"3d7e2604-92c1-4c93-b168-0683ed2990d1","title":"Machine Learning Engineer","department":"Machine Learning","team":"Machine Learning","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[{"location":"Remote (U.S. or International)","address":{"postalAddress":{"addressCountry":"United States"}}}],"publishedAt":"2026-09-01T19:40:21.501+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/3d7e2604-92c1-4c93-b168-0683ed2990d1","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/3d7e2604-92c1-4c93-b168-0683ed2990d1/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.
As a Machine Learning Engineer at Gray Swan AI, you will play a pivotal role in shaping the future of AI safety solutions.
Research at Gray Swan AI is tightly tied to real-world impact. AI security is not a solved problem, and this role is a mix of applied research and system building: developing new approaches to adversarial testing, model evaluation, and robust inference that directly inform how secure AI systems are deployed in practice. You will work at the boundary between research and production, translating novel ideas into scalable AI systems that withstand adversarial pressure.
Your expertise in state-of-the-art deep learning architectures, distributed systems, and parallel computing will enable you to tackle complex challenges associated with resource-intensive models. You will be responsible for advancing our methodologies for controlling, monitoring, and analyzing these models, ensuring they meet the rigorous demands of production environments.
Join Gray Swan AI to work alongside leading minds in AI safety and apply your technical depth to problems that genuinely matter!
Lead the design, development, and deployment of advanced machine learning models to enhance system performance and scalability.
Tackle complex challenges associated with resource-intensive models using distributed systems and parallel computing.
Advance methodologies for controlling, monitoring, and analyzing machine learning models in production environments.
Develop new approaches to adversarial testing, model evaluation, and robust inference.
Translate research ideas into scalable AI systems deployed in real-world, adversarial settings.
Work closely with cross-functional teams to ensure research outcomes inform production systems.
Bachelor’s degree in Computer Science, Machine Learning, Engineering, or a related technical field is required.
Experience in building and deploying machine learning models and systems.
Demonstrated expertise in designing, training, and deploying deep learning models with frameworks like PyTorch.
Strong programming experience in Python and C++ (preferred)
Practical experience developing scalable machine learning pipelines and integrating them with cloud infrastructure (e.g., AWS, GCP, Azure).
Experience conducting ML research, including building research prototype systems, experiment design, empirical analysis of results, and communicating results via publications.
Good to have: experience with modern ML methods such as LLMs (training, finetuning, and/or analyzing), synthetic data generation pipelines, and AI safety or security work.
In-depth knowledge of neural network architectures, including sequence models, transformers, and other state-of-the-art approaches.
Strong algorithmic problem-solving skills and comprehensive knowledge of ML theory and optimization techniques.
Proficiency in data preprocessing, transformation, and handling large-scale, multi-modal datasets.
Experience with AI safety practices such as model validation, robustness testing, and continuous monitoring for safety and security incidents throughout deployment.
Experience with AI safety and security assessments and adversarial testing.
You are genuinely excited by the intersection of research and engineering, and want to both develop new AI safety ideas and see them running in real systems.
You are motivated by real-world impact and want your work to directly influence how major AI companies deploy models right now (we work with many of the leading AI labs).
You are eager to deepen your AI safety expertise by working alongside a team that includes some of the most respected and influential thinkers in the field.
You thrive in a fast-paced, dynamic startup environment where ambiguity is expected.
You bring strong collaboration and problem-solving skills, with a focus on driving meaningful, lasting impact.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Salary: $160-257k, depending on level, plus performance-based bonus and a competitive equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nAs a Machine Learning Engineer at Gray Swan AI, you will play a pivotal role in shaping the future of AI safety solutions.\n\nResearch at Gray Swan AI is tightly tied to real-world impact. AI security is not a solved problem, and this role is a mix of applied research and system building: developing new approaches to adversarial testing, model evaluation, and robust inference that directly inform how secure AI systems are deployed in practice. You will work at the boundary between research and production, translating novel ideas into scalable AI systems that withstand adversarial pressure.\n\nYour expertise in state-of-the-art deep learning architectures, distributed systems, and parallel computing will enable you to tackle complex challenges associated with resource-intensive models. You will be responsible for advancing our methodologies for controlling, monitoring, and analyzing these models, ensuring they meet the rigorous demands of production environments.\n\nJoin Gray Swan AI to work alongside leading minds in AI safety and apply your technical depth to problems that genuinely matter!\n\n\n\n\nWHAT YOU’LL DO\n\n - Lead the design, development, and deployment of advanced machine learning models to enhance system performance and scalability.\n\n - Tackle complex challenges associated with resource-intensive models using distributed systems and parallel computing.\n\n - Advance methodologies for controlling, monitoring, and analyzing machine learning models in production environments.\n\n - Develop new approaches to adversarial testing, model evaluation, and robust inference.\n\n - Translate research ideas into scalable AI systems deployed in real-world, adversarial settings.\n\n - Work closely with cross-functional teams to ensure research outcomes inform production systems.\n\n\n\n\nWHO YOU ARE\n\n\nEDUCATION\n\n - Bachelor’s degree in Computer Science, Machine Learning, Engineering, or a related technical field is required.\n\n\nEXPERIENCE\n\n - Experience in building and deploying machine learning models and systems.\n\n - Demonstrated expertise in designing, training, and deploying deep learning models with frameworks like PyTorch.\n\n - Strong programming experience in Python and C++ (preferred)\n\n - Practical experience developing scalable machine learning pipelines and integrating them with cloud infrastructure (e.g., AWS, GCP, Azure).\n\n - Experience conducting ML research, including building research prototype systems, experiment design, empirical analysis of results, and communicating results via publications.\n\n - Good to have: experience with modern ML methods such as LLMs (training, finetuning, and/or analyzing), synthetic data generation pipelines, and AI safety or security work.\n\n\nCORE TECHNICAL SKILLS\n\n - In-depth knowledge of neural network architectures, including sequence models, transformers, and other state-of-the-art approaches.\n\n - Strong algorithmic problem-solving skills and comprehensive knowledge of ML theory and optimization techniques.\n\n - Proficiency in data preprocessing, transformation, and handling large-scale, multi-modal datasets.\n\n\n\n\nBONUS POINTS IF YOU HAVE\n\n - Experience with AI safety practices such as model validation, robustness testing, and continuous monitoring for safety and security incidents throughout deployment.\n\n - Experience with AI safety and security assessments and adversarial testing.\n\n\n\n\nYOU’LL THRIVE HERE IF\n\n - You are genuinely excited by the intersection of research and engineering, and want to both develop new AI safety ideas and see them running in real systems.\n\n - You are motivated by real-world impact and want your work to directly influence how major AI companies deploy models right now (we work with many of the leading AI labs).\n\n - You are eager to deepen your AI safety expertise by working alongside a team that includes some of the most respected and influential thinkers in the field.\n\n - You thrive in a fast-paced, dynamic startup environment where ambiguity is expected.\n\n - You bring strong collaboration and problem-solving skills, with a focus on driving meaningful, lasting impact.\n\n\n\n\nCOMPENSATION & BENEFITS\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nSalary: $160-257k, depending on level, plus performance-based bonus and a competitive equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast."},{"id":"8a4d2f2d-5919-4b7d-bb85-a45da7e72e8a","title":"Head of Growth & Demand Generation","department":"Marketing","team":"Marketing","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-01T19:40:50.236+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/8a4d2f2d-5919-4b7d-bb85-a45da7e72e8a","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/8a4d2f2d-5919-4b7d-bb85-a45da7e72e8a/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
The Head of Growth & Demand Generation owns Gray Swan’s pipeline generation strategy. This is a revenue-critical leadership role responsible for building and scaling a repeatable demand engine that consistently generates high-quality, sales-accepted pipeline.
You’ll partner closely with Sales, Product, and company leadership to define our demand strategy, identify the highest-impact digital growth opportunities, and execute programs that accelerate revenue. As an early marketing leader, you’ll have the opportunity to shape both the function and the company’s long-term growth strategy.
This role includes a variable compensation component tied directly to qualified pipeline generation, aligning marketing performance with measurable business outcomes.
Build and scale a multi-channel demand generation engine across outbound, inbound, ABM, paid media, partnerships, content, events, and growth experiments.
Own quarterly and annual pipeline gen targets aligned with company revenue goals.
Define our targeted segmentation strategy and channel mix to maximize pipeline creation and conversion.
Partner closely with Sales leadership to improve lead quality, qualification, conversion rates, and overall pipeline efficiency.
Own marketing performance, including budget allocation, attribution, ROI, funnel conversion, and experimentation across every stage of the lead journey.
Collaborate with Product, GTM Operations, and executive leadership to continuously refine and develop high-converting generation campaigns to explode revenue growth.
5+ years of experience in B2B SaaS, Cyber Security or AI Security marketing, with a strong focus on demand generation, growth marketing, or revenue marketing.
Proven track record of building and scaling pipeline generation programs within a high-growth startup environment.
Experience developing integrated demand generation strategies across inbound, outbound, ABM, paid acquisition, partnerships, and events.
Strong understanding of marketing analytics, attribution, funnel optimization, and performance measurement.
Experience with modern marketing and sales technology (we currently use HubSpot), along with a data-driven approach to experimentation and optimization.
Comfortable operating as both a strategic leader and a hands-on builder in a fast-moving environment.
If you don’t meet 100% of these qualifications, we still encourage you to apply. We care more about your ability to create impact than checking every box.
Obsessed with building predictable, repeatable pipelines — not just generating marketing activity.
Experience using AI tools/automation as force multipliers to move faster, work smarter.
Highly analytical, naturally curious, and constantly testing new ideas to improve performance.
Comfortable owning ambitious growth goals and being measured by business outcomes.
Equally energized by developing strategy and rolling up your sleeves to execute.
Motivated by building something from the ground up and helping define the next phase of Gray Swan’s growth.
Ownership, high accountability - end to end campaigns
Self Starter
What We Offer:
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $170,000 - $250,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nThe Head of Growth & Demand Generation owns Gray Swan’s pipeline generation strategy. This is a revenue-critical leadership role responsible for building and scaling a repeatable demand engine that consistently generates high-quality, sales-accepted pipeline.\n\nYou’ll partner closely with Sales, Product, and company leadership to define our demand strategy, identify the highest-impact digital growth opportunities, and execute programs that accelerate revenue. As an early marketing leader, you’ll have the opportunity to shape both the function and the company’s long-term growth strategy.\n\nThis role includes a variable compensation component tied directly to qualified pipeline generation, aligning marketing performance with measurable business outcomes.\n\n\n\n\nWHAT YOU’LL DO\n\n - Build and scale a multi-channel demand generation engine across outbound, inbound, ABM, paid media, partnerships, content, events, and growth experiments.\n\n - Own quarterly and annual pipeline gen targets aligned with company revenue goals.\n\n - Define our targeted segmentation strategy and channel mix to maximize pipeline creation and conversion.\n\n - Partner closely with Sales leadership to improve lead quality, qualification, conversion rates, and overall pipeline efficiency.\n\n - Own marketing performance, including budget allocation, attribution, ROI, funnel conversion, and experimentation across every stage of the lead journey.\n\n - Collaborate with Product, GTM Operations, and executive leadership to continuously refine and develop high-converting generation campaigns to explode revenue growth.\n \n \n\n\nWHO YOU ARE\n\n - 5+ years of experience in B2B SaaS, Cyber Security or AI Security marketing, with a strong focus on demand generation, growth marketing, or revenue marketing.\n\n - Proven track record of building and scaling pipeline generation programs within a high-growth startup environment.\n\n - Experience developing integrated demand generation strategies across inbound, outbound, ABM, paid acquisition, partnerships, and events.\n\n - Strong understanding of marketing analytics, attribution, funnel optimization, and performance measurement.\n\n - Experience with modern marketing and sales technology (we currently use HubSpot), along with a data-driven approach to experimentation and optimization.\n\n - Comfortable operating as both a strategic leader and a hands-on builder in a fast-moving environment.\n\nIf you don’t meet 100% of these qualifications, we still encourage you to apply. We care more about your ability to create impact than checking every box.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU ARE\n\n - Obsessed with building predictable, repeatable pipelines — not just generating marketing activity.\n\n - Experience using AI tools/automation as force multipliers to move faster, work smarter.\n\n - Highly analytical, naturally curious, and constantly testing new ideas to improve performance.\n\n - Comfortable owning ambitious growth goals and being measured by business outcomes.\n\n - Equally energized by developing strategy and rolling up your sleeves to execute.\n\n - Motivated by building something from the ground up and helping define the next phase of Gray Swan’s growth.\n\n - Ownership, high accountability - end to end campaigns\n\n - Self Starter\n\n\n\nWhat We Offer:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $170,000 - $250,000 plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"d209ab12-9fac-4827-a5f6-d4bbe1f033b8","title":"Arena Growth Marketing Manager (Pittsburgh or Remote U.S.)","department":"Marketing","team":"Marketing","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-01T19:41:23.069+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d209ab12-9fac-4827-a5f6-d4bbe1f033b8","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d209ab12-9fac-4827-a5f6-d4bbe1f033b8/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
About Arena
The Gray Swan Arena is where the world's top frontier labs send their AI models to be stress-tested by our community of over 15,000 red teamers..
AI Researchers, security specialists, prompt engineers, and AI enthusiasts participate in challenges that uncover vulnerabilities, reveal model weaknesses, and generate valuable safety insights. Participants are not only incentivized by recognition and prizes, but for the opportunity to directly influence the future of AI safety and security.
We're building the premier destination for AI security talent. We're looking for someone who can help us scale it.
We're looking for an Arena Marketing Manager to own user acquisition, engagement, and community growth for Arena.
This is not a traditional marketing role.
You'll be responsible for growing a highly technical audience of AI red-teamers, security researchers, hackers, builders, and AI safety enthusiasts. You'll design experiments, launch campaigns, build partnerships, manage creators and influencers, activate communities, and develop repeatable growth engines that increase participation across Arena challenges.
Success in this role means attracting more qualified participants, increasing challenge engagement, and helping Arena become the default place where top AI security talent gathers.
You'll work closely with product, research, partnerships, and leadership teams while having significant autonomy to shape strategy and execution.
Drive User Growth
Own participant acquisition strategy across multiple channels
Design and execute growth experiments across social, influencer, community, partnership, event, and paid channels
dentify high-performing acquisition channels and scale what works
Build repeatable growth systems that increase registrations, challenge participation, and
retention
Own Challenge Launch Marketing
Develop and execute go-to-market plans for Arena challenges
Lead challenge announcements, launch campaigns, and ongoing promotional efforts
Coordinate with AI lab partners and internal teams to maximize visibility and participation
Create launch playbooks that improve performance over time
Build and Grow the Arena Community
Own Arena's community presence, particularly within Discord
Develop engagement programs, events, activations, and community initiatives that increase participation and retention
Foster a culture that attracts elite AI red-teamers and technical contributors
Surface community insights that improve both marketing and product decisions
Expand Partnerships & Influencer Programs
Grow relationships with creators, researchers, security experts, and technical influencers
Manage and expand strategic marketing partnerships
Develop systems to measure partnership and influencer ROI
Identify new opportunities to reach high-quality participants
Create Compelling Content
Help define Arena's consumer-facing brand voice
Translate community activity, challenge outcomes, and research insights into engaging content
Showcase how participant contributions influence AI safety and security research
Develop content that drives awareness, credibility, and participation
Measure and Optimize
Own acquisition, activation, engagement, and retention metrics
Build reporting frameworks and dashboards
Analyze campaign performance and make data-driven recommendations
Manage challenge marketing budgets for maximum impact
Support Community-Led Events
Research, plan, and execute hackathons, conferences, meetups, and other community events
Build relationships with organizations and communities aligned with Arena's mission
Use events as a channel for participant acquisition and brand building
Success in Your First 90 Days
Develop a deep understanding of Arena users and growth opportunities
Audit existing acquisition channels and marketing performance
Launch several growth experiments across multiple channels
Build a repeatable challenge launch process
Establish reporting around registrations, participation, retention, and channel ROI
Deliver measurable growth in qualified challenge participation
Proven track record of driving user growth through marketing initiatives
Experience owning and executing multi-channel campaigns
Strong analytical mindset with a focus on measurable outcomes
Exceptional written and verbal communication skills
Comfortable moving quickly, operating independently, and experimenting frequently
Highly organized and capable of managing multiple projects simultaneously
Curious about emerging technologies and online communities
Experience marketing to developers, researchers, security professionals, or technical audiences
Experience growing online communities, especially Discord
Experience managing influencer or creator programs
Familiarity with AI, AI safety, cybersecurity, or adjacent technical ecosystems
Experience running hackathons, competitions, or community-driven programs
Conversion rate optimization and growth experimentation experience
If you don't meet every qualification, we still encourage you to apply. We care more about your ability to learn, execute, and create impact than checking every box.
What We Offer:
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $90,000-160,000 for Tier 1 locations (San Francisco, Seattle, Boston, NYC) and $80,000-$145,000 for Tier 2 (all other U.S. locations)
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\nAbout Arena\n\nThe Gray Swan Arena is where the world's top frontier labs send their AI models to be stress-tested by our community of over 15,000 red teamers..\n\nAI Researchers, security specialists, prompt engineers, and AI enthusiasts participate in challenges that uncover vulnerabilities, reveal model weaknesses, and generate valuable safety insights. Participants are not only incentivized by recognition and prizes, but for the opportunity to directly influence the future of AI safety and security.\n\nWe're building the premier destination for AI security talent. We're looking for someone who can help us scale it.\n\n\n\n\nTHE ROLE\n\nWe're looking for an Arena Marketing Manager to own user acquisition, engagement, and community growth for Arena.\n\nThis is not a traditional marketing role.\n\nYou'll be responsible for growing a highly technical audience of AI red-teamers, security researchers, hackers, builders, and AI safety enthusiasts. You'll design experiments, launch campaigns, build partnerships, manage creators and influencers, activate communities, and develop repeatable growth engines that increase participation across Arena challenges.\n\nSuccess in this role means attracting more qualified participants, increasing challenge engagement, and helping Arena become the default place where top AI security talent gathers.\n\nYou'll work closely with product, research, partnerships, and leadership teams while having significant autonomy to shape strategy and execution.\n\n\n\n\nWHAT YOU’LL DO:\n\nDrive User Growth\n\n - Own participant acquisition strategy across multiple channels\n\n - Design and execute growth experiments across social, influencer, community, partnership, event, and paid channels\n\n - dentify high-performing acquisition channels and scale what works\n\n - Build repeatable growth systems that increase registrations, challenge participation, and\n\n retention\n\nOwn Challenge Launch Marketing\n\n - Develop and execute go-to-market plans for Arena challenges\n\n - Lead challenge announcements, launch campaigns, and ongoing promotional efforts\n\n - Coordinate with AI lab partners and internal teams to maximize visibility and participation\n\n - Create launch playbooks that improve performance over time\n\nBuild and Grow the Arena Community\n\n - Own Arena's community presence, particularly within Discord\n\n - Develop engagement programs, events, activations, and community initiatives that increase participation and retention\n\n - Foster a culture that attracts elite AI red-teamers and technical contributors\n\n - Surface community insights that improve both marketing and product decisions\n\nExpand Partnerships & Influencer Programs\n\n - Grow relationships with creators, researchers, security experts, and technical influencers\n\n - Manage and expand strategic marketing partnerships\n\n - Develop systems to measure partnership and influencer ROI\n\n - Identify new opportunities to reach high-quality participants\n\nCreate Compelling Content\n\n - Help define Arena's consumer-facing brand voice\n\n - Translate community activity, challenge outcomes, and research insights into engaging content\n\n - Showcase how participant contributions influence AI safety and security research\n\n - Develop content that drives awareness, credibility, and participation\n\nMeasure and Optimize\n\n - Own acquisition, activation, engagement, and retention metrics\n\n - Build reporting frameworks and dashboards\n\n - Analyze campaign performance and make data-driven recommendations\n\n - Manage challenge marketing budgets for maximum impact\n\nSupport Community-Led Events\n\n - Research, plan, and execute hackathons, conferences, meetups, and other community events\n\n - Build relationships with organizations and communities aligned with Arena's mission\n\n - Use events as a channel for participant acquisition and brand building\n\nSuccess in Your First 90 Days\n\n - Develop a deep understanding of Arena users and growth opportunities\n\n - Audit existing acquisition channels and marketing performance\n\n - Launch several growth experiments across multiple channels\n\n - Build a repeatable challenge launch process\n\n - Establish reporting around registrations, participation, retention, and channel ROI\n\n - Deliver measurable growth in qualified challenge participation\n\n\n\n\n\nWHO YOU ARE:\n\n - Proven track record of driving user growth through marketing initiatives\n\n - Experience owning and executing multi-channel campaigns\n\n - Strong analytical mindset with a focus on measurable outcomes\n\n - Exceptional written and verbal communication skills\n\n - Comfortable moving quickly, operating independently, and experimenting frequently\n\n - Highly organized and capable of managing multiple projects simultaneously\n\n - Curious about emerging technologies and online communities\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience marketing to developers, researchers, security professionals, or technical audiences\n\n - Experience growing online communities, especially Discord\n\n - Experience managing influencer or creator programs\n\n - Familiarity with AI, AI safety, cybersecurity, or adjacent technical ecosystems\n\n - Experience running hackathons, competitions, or community-driven programs\n\n - Conversion rate optimization and growth experimentation experience\n\nIf you don't meet every qualification, we still encourage you to apply. We care more about your ability to learn, execute, and create impact than checking every box.\n\n\n\nWhat We Offer:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $90,000-160,000 for Tier 1 locations (San Francisco, Seattle, Boston, NYC) and $80,000-$145,000 for Tier 2 (all other U.S. locations)\n\n \n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"2ade8bba-aea9-4c1d-a194-b88d3a13d1cb","title":"Staff Software Engineer (Pittsburgh)","department":"Software Engineering","team":"Software Engineering","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[],"publishedAt":"2026-09-01T19:43:39.296+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/2ade8bba-aea9-4c1d-a194-b88d3a13d1cb","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/2ade8bba-aea9-4c1d-a194-b88d3a13d1cb/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
We’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.
You don’t need to have used every tool we use. What matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!
Design and develop web applications using modern frontend frameworks like Svelte
Build intuitive and user-friendly interfaces that delight users
Develop and maintain backend APIs using tools like FastAPI
Manage and optimize database systems like MongoDB
Collaborate with our ML research team to integrate AI experiences into our products
Proficiency in TypeScript or JavaScript
Experience with frontend frameworks such as React, Vue, or Svelte
Solid understanding of HTML and CSS
Hands-on experience building backend APIs
Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)
SvelteKit experience
Python proficiency and AI/ML framework exposure
Experience in creating AI-driven applications
Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)
Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows
Knowledge of secure coding practices and mitigating vulnerabilities in web applications
Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work
Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality
Understanding of AI safety principles or ethical considerations in AI systems
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You've learned things about your code only production traffic can teach
You're comfortable debugging across the stack – from browser devtools to database query plans.
You've worked in environments where moving fast matters and you know how to balance speed with sustainability.
You're interested in applying your security mindset to AI, where the threat model is still being written
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $210k-$280k plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for a software engineer who wants to build things end to end and doesn’t mind getting their hands dirty. You’ll work across the stack—frontend, backend APIs, and databases—helping us turn ideas into real product and improve what’s already in production.\n\nYou don’t need to have used every tool we use. What matters is that you have solid full-stack experience, pick up new technologies quickly, and are comfortable owning work without a lot of process or hand-holding. We are still in the early stages of our growth, so if you like autonomy, responsibility, and moving fast, then please apply for this opportunity!\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design and develop web applications using modern frontend frameworks like Svelte\n\n - Build intuitive and user-friendly interfaces that delight users\n\n - Develop and maintain backend APIs using tools like FastAPI\n\n - Manage and optimize database systems like MongoDB\n\n - Collaborate with our ML research team to integrate AI experiences into our products\n\n\n\n\nWHO YOU ARE:\n\n - Proficiency in TypeScript or JavaScript\n\n - Experience with frontend frameworks such as React, Vue, or Svelte\n\n - Solid understanding of HTML and CSS\n\n - Hands-on experience building backend APIs\n\n - Knowledge of database systems (SQL or NoSQL; MongoDB is a plus)\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - SvelteKit experience\n\n - Python proficiency and AI/ML framework exposure\n\n - Experience in creating AI-driven applications\n\n - Experience deploying and scaling applications on cloud platforms (e.g., AWS, Google Cloud, Azure)\n\n - Familiarity with CI/CD pipelines and DevOps practices to streamline development workflows\n\n - Knowledge of secure coding practices and mitigating vulnerabilities in web applications\n\n - Contributions to open-source projects or an active GitHub/portfolio showcasing relevant work\n\n - Experience with testing frameworks (e.g., Jest, Playwright) to ensure code quality\n\n - Understanding of AI safety principles or ethical considerations in AI systems\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You've learned things about your code only production traffic can teach\n\n - You're comfortable debugging across the stack – from browser devtools to database query plans.\n\n - You've worked in environments where moving fast matters and you know how to balance speed with sustainability.\n\n - You're interested in applying your security mindset to AI, where the threat model is still being written\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $210k-$280k plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application. "},{"id":"d564e180-807e-4da1-9955-1bfdcdab1e38","title":"Head of Cyber Safety","department":"Red Team","team":"Red Team","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-12T23:38:30.636+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d564e180-807e-4da1-9955-1bfdcdab1e38","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d564e180-807e-4da1-9955-1bfdcdab1e38/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
Come build and lead Gray Swan's cyber safety capability from the ground up, serving as the technical authority on AI-enabled cyber risk across red-teaming, evaluation, benchmarking, defenses, and safety infrastructure development. You'll help define how frontier AI systems are evaluated for offensive cyber capabilities while partnering with leading AI labs to reduce real-world security risks.
This role sits at the intersection of offensive security, AI safety, and machine learning. You'll transform deep cybersecurity expertise into scalable evaluation methodologies, safety infrastructure, and automated defenses that help establish industry standards for frontier model security.
If you have deep expertise in offensive cybersecurity, vulnerability research, or adversarial AI security, experience evaluating frontier models, and are driven to reduce catastrophic cyber risks from increasingly capable AI systems, we'd love to hear from you.
Design and lead adversarial evaluations of frontier LLMs for offensive cyber capabilities, including vulnerability discovery, exploit development, malware generation, privilege escalation, social engineering, persistence, and autonomous cyber operations across text, agentic, and multimodal systems.
Partner closely with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, automated detection systems, and evaluation infrastructure for both internal products and frontier AI lab deployments.
Develop and maintain Gray Swan’s catastrophic cyber harm taxonomy, continuously evolving cyber evaluation frameworks as frontier model capabilities rapidly advance.
Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders, helping guide responsible model deployment and security mitigations.
Build, mentor, and lead a world-class team of cybersecurity subject matter experts while establishing scalable evaluation processes, quality standards, and technical infrastructure.
Represent Gray Swan as the company's cybersecurity authority, collaborating with frontier AI labs, security researchers, government partners, and the broader AI safety and cybersecurity communities.
Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or a closely related field through industry, research, or equivalent experience.
Significant experience assessing advanced cyber threats, offensive tooling, or AI-enabled cyber capabilities, especially in critical infrastructure domains.
Hands-on experience conducting adversarial evaluations, AI red-teaming, LLM security research, or building evaluation datasets for frontier AI systems.
Comfortable operating at the intersection of cybersecurity research, AI safety, and machine learning engineering.
Thrive in highly ambiguous, fast-moving environments where you'll define strategy while building entirely new capabilities.
A builder who enjoys creating teams, infrastructure, and evaluation systems from scratch.
Experience developing machine learning models, AI security classifiers, or automated cyber detection systems.
Hands-on experience red-teaming frontier language models, jailbreaking, prompt injection research, or agentic AI evaluations.
Experience working with frontier AI labs, national security organizations, or leading cybersecurity research teams.
Background in threat intelligence, autonomous cyber operations, AI agent security, or AI governance.
Strong software engineering experience in Python, Go, Rust, or other systems programming languages.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Want visibility across the frontier of AI security by evaluating multiple frontier models and working directly with the world's leading AI labs.
Are excited to build the infrastructure that makes AI cyber safety scalable.
Feel motivated to reduce catastrophic cyber risks posed by increasingly capable AI systems.
Enjoy turning offensive security research into practical defenses that improve the safety of frontier AI.
Have a vision for what world-class AI cyber safety should look like—and are excited to build it.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $230,000 - $280,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nCome build and lead Gray Swan's cyber safety capability from the ground up, serving as the technical authority on AI-enabled cyber risk across red-teaming, evaluation, benchmarking, defenses, and safety infrastructure development. You'll help define how frontier AI systems are evaluated for offensive cyber capabilities while partnering with leading AI labs to reduce real-world security risks.\n\nThis role sits at the intersection of offensive security, AI safety, and machine learning. You'll transform deep cybersecurity expertise into scalable evaluation methodologies, safety infrastructure, and automated defenses that help establish industry standards for frontier model security.\n\n\n\nIf you have deep expertise in offensive cybersecurity, vulnerability research, or adversarial AI security, experience evaluating frontier models, and are driven to reduce catastrophic cyber risks from increasingly capable AI systems, we'd love to hear from you.\n\n\n\nWHAT YOU’LL DO:\n\n - Design and lead adversarial evaluations of frontier LLMs for offensive cyber capabilities, including vulnerability discovery, exploit development, malware generation, privilege escalation, social engineering, persistence, and autonomous cyber operations across text, agentic, and multimodal systems.\n\n - Partner closely with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, automated detection systems, and evaluation infrastructure for both internal products and frontier AI lab deployments.\n\n - Develop and maintain Gray Swan’s catastrophic cyber harm taxonomy, continuously evolving cyber evaluation frameworks as frontier model capabilities rapidly advance.\n\n - Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders, helping guide responsible model deployment and security mitigations.\n\n - Build, mentor, and lead a world-class team of cybersecurity subject matter experts while establishing scalable evaluation processes, quality standards, and technical infrastructure.\n\n - Represent Gray Swan as the company's cybersecurity authority, collaborating with frontier AI labs, security researchers, government partners, and the broader AI safety and cybersecurity communities.\n \n\n\nWHO YOU ARE:\n\n - Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or a closely related field through industry, research, or equivalent experience.\n\n - Significant experience assessing advanced cyber threats, offensive tooling, or AI-enabled cyber capabilities, especially in critical infrastructure domains.\n\n - Hands-on experience conducting adversarial evaluations, AI red-teaming, LLM security research, or building evaluation datasets for frontier AI systems.\n\n - Comfortable operating at the intersection of cybersecurity research, AI safety, and machine learning engineering.\n\n - Thrive in highly ambiguous, fast-moving environments where you'll define strategy while building entirely new capabilities.\n\n - A builder who enjoys creating teams, infrastructure, and evaluation systems from scratch.\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience developing machine learning models, AI security classifiers, or automated cyber detection systems.\n\n - Hands-on experience red-teaming frontier language models, jailbreaking, prompt injection research, or agentic AI evaluations.\n\n - Experience working with frontier AI labs, national security organizations, or leading cybersecurity research teams.\n\n - Background in threat intelligence, autonomous cyber operations, AI agent security, or AI governance.\n\n - Strong software engineering experience in Python, Go, Rust, or other systems programming languages.\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Want visibility across the frontier of AI security by evaluating multiple frontier models and working directly with the world's leading AI labs.\n\n - Are excited to build the infrastructure that makes AI cyber safety scalable.\n\n - Feel motivated to reduce catastrophic cyber risks posed by increasingly capable AI systems.\n\n - Enjoy turning offensive security research into practical defenses that improve the safety of frontier AI.\n\n - Have a vision for what world-class AI cyber safety should look like—and are excited to build it.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $230,000 - $280,000 plus performance based bonus and meaningful equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"c138b218-30c4-4d08-ba4a-0db4fb64eb38","title":"Software Engineer, Infrastructure ","department":"Software Engineering","team":"Software Engineering","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[{"location":"Remote (U.S. Only)","address":{"postalAddress":{"addressCountry":"United States"}}}],"publishedAt":"2026-09-11T11:36:10.181+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/c138b218-30c4-4d08-ba4a-0db4fb64eb38","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/c138b218-30c4-4d08-ba4a-0db4fb64eb38/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
Gray Swan is looking for an Infrastructure Engineer to build and scale the systems that power our AI security platform. You'll design the backend services, distributed infrastructure, and cloud architecture that enable Gray Swan to build AI systems and for customers to safely deploy frontier AI models at scale.
This role is ideal for an engineer who enjoys solving infrastructure challenges across reliability, scalability, observability, and performance. You'll work closely with machine learning engineers, product engineers, and security researchers to ensure our platform remains fast, resilient, and secure as we grow.
You'll have significant ownership over foundational systems and the opportunity to influence technical direction in a rapidly evolving AI startup.
Design, build, and maintain highly available backend services and distributed systems that power Gray Swan's AI security platform.
Own cloud infrastructure across Kubernetes, AWS, networking, storage, and compute to ensure reliable production environments.
Build scalable APIs, internal platform services, and infrastructure tooling that improve developer productivity and system reliability.
Improve system observability through logging, metrics, tracing, dashboards, and automated alerting.
Optimize performance, latency, and infrastructure costs while maintaining reliability and security.
Partner closely with machine learning, security, and product engineering teams to deliver production-ready infrastructure for AI workloads.
5+ years of experience building backend infrastructure or distributed systems in production environments.
Strong programming skills in C/C++, Go, Python, Rust, or Java.
Experience operating services on Kubernetes and modern cloud platforms such as AWS, GCP, or Azure.
Deep understanding of networking, distributed systems, containers, service orchestration, and scalable architectures.
Experience designing APIs, microservices, asynchronous systems, and event-driven architectures.
Comfortable debugging complex production issues and improving reliability through automation and operational excellence.
Passionate about writing clean, maintainable code and building infrastructure that other engineers love using.
Excited to work in a fast-moving startup with significant ownership and ambiguity.
Experience supporting machine learning or LLM infrastructure.
Familiarity with infrastructure-as-code tools.
Experience with Kafka, Redis, PostgreSQL, ClickHouse, or similar distributed data systems.
Experience building internal developer platforms or platform engineering tooling.
Knowledge of cloud security, infrastructure hardening, or zero-trust architectures.
Previous experience at a high-growth startup or building products from zero to one.
Interest in AI safety, cybersecurity, or adversarial machine learning.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You thrive on ownership and solving hard problems. You're energized by ambiguity, enjoy building systems from the ground up, and take pride in delivering reliable solutions from design through production.
You think at scale. You enjoy designing resilient infrastructure, optimizing performance, and building systems that are secure, observable, and built to grow.
You collaborate across disciplines. You work effectively with machine learning engineers, security researchers, and product teams, knowing that the best infrastructure enables everyone else to move faster.
You're excited by our mission and startup environment. You enjoy moving quickly, adapting to change, and helping build the foundation for the future of secure AI.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $180,000 - $290,000 (depending on level) plus performance based bonus and meaningful equity package.
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nGray Swan is looking for an Infrastructure Engineer to build and scale the systems that power our AI security platform. You'll design the backend services, distributed infrastructure, and cloud architecture that enable Gray Swan to build AI systems and for customers to safely deploy frontier AI models at scale.\n\nThis role is ideal for an engineer who enjoys solving infrastructure challenges across reliability, scalability, observability, and performance. You'll work closely with machine learning engineers, product engineers, and security researchers to ensure our platform remains fast, resilient, and secure as we grow.\n\nYou'll have significant ownership over foundational systems and the opportunity to influence technical direction in a rapidly evolving AI startup.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design, build, and maintain highly available backend services and distributed systems that power Gray Swan's AI security platform.\n\n - Own cloud infrastructure across Kubernetes, AWS, networking, storage, and compute to ensure reliable production environments.\n\n - Build scalable APIs, internal platform services, and infrastructure tooling that improve developer productivity and system reliability.\n\n - Improve system observability through logging, metrics, tracing, dashboards, and automated alerting.\n\n - Optimize performance, latency, and infrastructure costs while maintaining reliability and security.\n\n - Partner closely with machine learning, security, and product engineering teams to deliver production-ready infrastructure for AI workloads.\n\n\n\n\nWHO YOU ARE:\n\n - 5+ years of experience building backend infrastructure or distributed systems in production environments.\n\n - Strong programming skills in C/C++, Go, Python, Rust, or Java.\n\n - Experience operating services on Kubernetes and modern cloud platforms such as AWS, GCP, or Azure.\n\n - Deep understanding of networking, distributed systems, containers, service orchestration, and scalable architectures.\n\n - Experience designing APIs, microservices, asynchronous systems, and event-driven architectures.\n\n - Comfortable debugging complex production issues and improving reliability through automation and operational excellence.\n\n - Passionate about writing clean, maintainable code and building infrastructure that other engineers love using.\n\n - Excited to work in a fast-moving startup with significant ownership and ambiguity.\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience supporting machine learning or LLM infrastructure.\n\n - Familiarity with infrastructure-as-code tools.\n\n - Experience with Kafka, Redis, PostgreSQL, ClickHouse, or similar distributed data systems.\n\n - Experience building internal developer platforms or platform engineering tooling.\n\n - Knowledge of cloud security, infrastructure hardening, or zero-trust architectures.\n\n - Previous experience at a high-growth startup or building products from zero to one.\n\n - Interest in AI safety, cybersecurity, or adversarial machine learning.\n\n\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You thrive on ownership and solving hard problems. You're energized by ambiguity, enjoy building systems from the ground up, and take pride in delivering reliable solutions from design through production.\n\n\n\n - You think at scale. You enjoy designing resilient infrastructure, optimizing performance, and building systems that are secure, observable, and built to grow.\n\n\n\n - You collaborate across disciplines. You work effectively with machine learning engineers, security researchers, and product teams, knowing that the best infrastructure enables everyone else to move faster.\n\n\n\n - You're excited by our mission and startup environment. You enjoy moving quickly, adapting to change, and helping build the foundation for the future of secure AI.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $180,000 - $290,000 (depending on level) plus performance based bonus and meaningful equity package.\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"e22e9376-8158-4b1d-bddf-e059bb846d6a","title":"Red Team Engineer","department":"Red Team","team":"Red Team","employmentType":"FullTime","location":"Remote (U.S. or International)","secondaryLocations":[],"publishedAt":"2026-09-01T19:35:04.674+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/e22e9376-8158-4b1d-bddf-e059bb846d6a","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/e22e9376-8158-4b1d-bddf-e059bb846d6a/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
Gray Swan Arena is where the world's top red-teamers test frontier AI models, learn about AI security, and win cash prizes. Leading labs use the resulting data to ensure that future LLMs are safe and aligned with human values.
Gray Swan’s Red Team Engineers are the hands-on practitioners behind both our popular Arena challenges and private red team engagements. You’ll design realistic attack scenarios, find vulnerabilities in frontier AI systems, and translate your findings into clear and actionable reports.
If you're a creative AI red teamer with thorough reporting skills, a strong technical background, and a knack for finding attack surfaces, we want to hear from you.
Design new challenges and adversarial scenarios for ongoing and upcoming Arena competitions
Work red teaming engagements with external clients, covering areas like prompt injection, tool use, and agent exploitation
Use Slack, Linear, our Arena design editor, and AI tools to deliver red-teaming results on time and with high quality
Build internal tools and processes for the Arena (e.g., cheating detection) and support operational tasks like break verification and prize distribution.
Work alongside Product and Engineering teams to create realistic scenarios that highlight attack surfaces in frontier systems
Help shape the future of Gray Swan Arena with novel ideas and challenge types
1+ years of experience in AI red teaming, adversarial ML, or related security research
Organized and comfortable working independently across multiple concurrent engagements
Proven ability to convey technical ideas in accessible reports
Comfortable with quick pivots and changing priorities.
Experience as a Gray Swan Arena competitor is a plus.
Background in traditional security research, CTFs, or penetration testing.
Experience with AI red teaming beyond LLM prompt injection
Degree or experience equivalent in Computer Science or related field
Familiarity with multimodal attack surfaces
Coding experience for automating or scaling test cases
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Have writing and scenario design skills with a collaborative communication style for effective cross-functional teamwork.
Have strong intuition about how AI systems fail in real-world deployments
Take ownership and deliver high-quality work under deadlines
Want to be on the cutting edge of AI safety and security, proactively defending against novel threat vectors
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $110,000 - $185,000 (depending on level & location) plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nGray Swan Arena is where the world's top red-teamers test frontier AI models, learn about AI security, and win cash prizes. Leading labs use the resulting data to ensure that future LLMs are safe and aligned with human values.\n\nGray Swan’s Red Team Engineers are the hands-on practitioners behind both our popular Arena challenges and private red team engagements. You’ll design realistic attack scenarios, find vulnerabilities in frontier AI systems, and translate your findings into clear and actionable reports.\n\nIf you're a creative AI red teamer with thorough reporting skills, a strong technical background, and a knack for finding attack surfaces, we want to hear from you.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design new challenges and adversarial scenarios for ongoing and upcoming Arena competitions\n\n - Work red teaming engagements with external clients, covering areas like prompt injection, tool use, and agent exploitation\n\n - Use Slack, Linear, our Arena design editor, and AI tools to deliver red-teaming results on time and with high quality\n\n - Build internal tools and processes for the Arena (e.g., cheating detection) and support operational tasks like break verification and prize distribution.\n\n - Work alongside Product and Engineering teams to create realistic scenarios that highlight attack surfaces in frontier systems\n\n - Help shape the future of Gray Swan Arena with novel ideas and challenge types\n\n\n\n\nWHO YOU ARE:\n\n - 1+ years of experience in AI red teaming, adversarial ML, or related security research\n\n - Organized and comfortable working independently across multiple concurrent engagements\n\n - Proven ability to convey technical ideas in accessible reports\n\n - Comfortable with quick pivots and changing priorities.\n\n - Experience as a Gray Swan Arena competitor is a plus.\n\n - Background in traditional security research, CTFs, or penetration testing.\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience with AI red teaming beyond LLM prompt injection\n\n - Degree or experience equivalent in Computer Science or related field\n\n - Familiarity with multimodal attack surfaces\n\n - Coding experience for automating or scaling test cases\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Have writing and scenario design skills with a collaborative communication style for effective cross-functional teamwork.\n\n - Have strong intuition about how AI systems fail in real-world deployments\n\n - Take ownership and deliver high-quality work under deadlines\n\n - Want to be on the cutting edge of AI safety and security, proactively defending against novel threat vectors\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $110,000 - $185,000 (depending on level & location) plus performance based bonus and meaningful equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"e38c5ee0-9a12-40aa-b218-4f5a7558e60a","title":"Director of Finance","department":"Operations","team":"Operations","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-01T19:23:48.408+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/e38c5ee0-9a12-40aa-b218-4f5a7558e60a","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/e38c5ee0-9a12-40aa-b218-4f5a7558e60a/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
We’re looking for our first Director of Finance to build and scale the financial foundation of Gray Swan as we enter our next phase of growth.
Reporting directly to executive leadership, this is a highly visible role that combines strategic finance with operational execution. You’ll own the company’s financial planning processes while building the systems, reporting, and operational rigor needed to support a rapidly scaling business.
This is not a role where you’ll simply oversee the work of others. We’re looking for a working director—someone equally comfortable owning the monthly close process, building complex financial models, implementing systems, preparing board materials, and partnering with leadership on strategic investments.
If you enjoy building from scratch, solving complex business problems, and operating with high ownership in a fast-moving startup, we’d love to talk.
Finance Operations
Own the monthly close process, partnering closely with external accounting partners to ensure accurate, timely financial reporting.
Oversee the order-to-cash process, including invoicing, customer payments, collections, and revenue operations.
Review and approve employee expense reports, ensuring policy compliance and operational efficiency.
Manage revenue recognition in accordance with GAAP and ensure accurate financial reporting.
Oversee day-to-day cash management, liquidity planning, and runway forecasting.
Develop financial reporting, KPI dashboards, and executive reporting that provide visibility into company performance.
Financial Planning and Analysis
Lead the annual budgeting process and rolling forecasts across all departments.
Build sophisticated financial models supporting hiring plans, infrastructure investments (including GPU spend), product initiatives, and strategic company investments.
Develop scenario analyses and long-range planning models that inform executive decision-making.
Partner with leadership on pricing, resource allocation, investment prioritization, and business planning.
Prepare financial reporting, analyses, and narratives for executive leadership, investors, and Board meetings.
Deliver actionable recommendations on growth opportunities, operating efficiency, margin improvement, and capital allocation.
Systems & Process
Evaluate, select, and lead implementation of a scalable ERP and financial systems stack.
Build finance processes that scale with company growth while improving reporting accuracy and operational efficiency.
Identify opportunities to automate workflows and leverage AI to improve forecasting, reporting, and financial operations.
Establish internal controls, financial policies, and operational best practices appropriate for a high-growth startup.
Cross-Functional Partnership
Partner closely with Accounting, Operations, and leadership on company-wide initiatives.
Serve as the primary finance business partner across the organization, translating financial insights into actionable business decisions.
Balance hands-on execution with strategic leadership, operating comfortably as both an individual contributor and functional leader.
Support fundraising, investor diligence, strategic planning, and special projects as the company scales.
8+ years of experience in strategic finance, FP&A, corporate finance, investment banking, consulting, or finance leadership roles within high-growth technology companies.
Experience building or scaling finance functions in startup or rapidly growing environments.
Strong understanding of accounting fundamentals, monthly close processes, revenue recognition, budgeting, forecasting, and cash management.
Exceptional financial modeling skills with experience building investment analyses, scenario planning, operating models, and board-level reporting.
Experience partnering directly with executive leadership to influence strategic decisions.
Comfortable owning both finance strategy and day-to-day operational execution.
Experience evaluating and implementing ERP systems or other finance technology platforms.
Strong executive communication skills with the ability to simplify complex financial information for diverse audiences.
Highly organized with exceptional attention to detail and a bias toward action.
Curious about AI and excited to leverage modern AI tools to improve financial planning and operational decision-making.
Thrives in ambiguity and enjoys building processes where none currently exist.
CPA, MBA, or advanced degree in Finance, Accounting, Economics, or Business.
Experience at a Series A or Series B SaaS startup.
Experience implementing NetSuite, Sage Intacct, Oracle, Workday, Adaptive Planning, Rippling, or similar ERP/FP&A platforms.
Experience supporting venture fundraising, investor relations, and Board reporting.
Deep understanding of SaaS metrics including ARR, burn multiple, CAC, gross margin, and cash runway.
Experience partnering closely with engineering organizations or evaluating infrastructure investments.
Experience building finance organizations from the ground up.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Established a predictable monthly close process and executive financial reporting cadence.
Built a scalable budgeting and forecasting process used across every department.
Improved visibility into cash flow, runway, revenue, and company performance.
Implemented stronger operational processes across invoicing, collections, expense management, and financial controls.
Delivered investment analyses that influence hiring, infrastructure, product, and go-to-market decisions.
Evaluated and began implementing the ERP and financial systems needed to support Gray Swan’s next stage of growth.
Become a trusted strategic advisor to leadership while remaining deeply involved in day-to-day finance execution.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $170,000 - $260,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
Submit your resume, link to your portfolio, and answer the questions on the application.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for our first Director of Finance to build and scale the financial foundation of Gray Swan as we enter our next phase of growth.\n\nReporting directly to executive leadership, this is a highly visible role that combines strategic finance with operational execution. You’ll own the company’s financial planning processes while building the systems, reporting, and operational rigor needed to support a rapidly scaling business.\n\nThis is not a role where you’ll simply oversee the work of others. We’re looking for a working director—someone equally comfortable owning the monthly close process, building complex financial models, implementing systems, preparing board materials, and partnering with leadership on strategic investments. \n\nIf you enjoy building from scratch, solving complex business problems, and operating with high ownership in a fast-moving startup, we’d love to talk.\n\n\n\n\nWHAT YOU’LL DO:\n\nFinance Operations\n\n - Own the monthly close process, partnering closely with external accounting partners to ensure accurate, timely financial reporting.\n\n - Oversee the order-to-cash process, including invoicing, customer payments, collections, and revenue operations.\n\n - Review and approve employee expense reports, ensuring policy compliance and operational efficiency.\n\n - Manage revenue recognition in accordance with GAAP and ensure accurate financial reporting.\n\n - Oversee day-to-day cash management, liquidity planning, and runway forecasting.\n\n - Develop financial reporting, KPI dashboards, and executive reporting that provide visibility into company performance.\n\nFinancial Planning and Analysis\n\n - Lead the annual budgeting process and rolling forecasts across all departments.\n\n - Build sophisticated financial models supporting hiring plans, infrastructure investments (including GPU spend), product initiatives, and strategic company investments.\n\n - Develop scenario analyses and long-range planning models that inform executive decision-making.\n\n - Partner with leadership on pricing, resource allocation, investment prioritization, and business planning.\n\n - Prepare financial reporting, analyses, and narratives for executive leadership, investors, and Board meetings.\n\n - Deliver actionable recommendations on growth opportunities, operating efficiency, margin improvement, and capital allocation.\n\nSystems & Process\n\n - Evaluate, select, and lead implementation of a scalable ERP and financial systems stack.\n\n - Build finance processes that scale with company growth while improving reporting accuracy and operational efficiency.\n\n - Identify opportunities to automate workflows and leverage AI to improve forecasting, reporting, and financial operations.\n\n - Establish internal controls, financial policies, and operational best practices appropriate for a high-growth startup.\n\nCross-Functional Partnership\n\n - Partner closely with Accounting, Operations, and leadership on company-wide initiatives.\n\n - Serve as the primary finance business partner across the organization, translating financial insights into actionable business decisions.\n\n - Balance hands-on execution with strategic leadership, operating comfortably as both an individual contributor and functional leader.\n\n - Support fundraising, investor diligence, strategic planning, and special projects as the company scales.\n\n\n\n\nWHO YOU ARE:\n\n - 8+ years of experience in strategic finance, FP&A, corporate finance, investment banking, consulting, or finance leadership roles within high-growth technology companies.\n\n - Experience building or scaling finance functions in startup or rapidly growing environments.\n\n - Strong understanding of accounting fundamentals, monthly close processes, revenue recognition, budgeting, forecasting, and cash management.\n\n - Exceptional financial modeling skills with experience building investment analyses, scenario planning, operating models, and board-level reporting.\n\n - Experience partnering directly with executive leadership to influence strategic decisions.\n\n - Comfortable owning both finance strategy and day-to-day operational execution.\n\n - Experience evaluating and implementing ERP systems or other finance technology platforms.\n\n - Strong executive communication skills with the ability to simplify complex financial information for diverse audiences.\n\n - Highly organized with exceptional attention to detail and a bias toward action.\n\n - Curious about AI and excited to leverage modern AI tools to improve financial planning and operational decision-making.\n\n - Thrives in ambiguity and enjoys building processes where none currently exist.\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - CPA, MBA, or advanced degree in Finance, Accounting, Economics, or Business.\n\n - Experience at a Series A or Series B SaaS startup.\n\n - Experience implementing NetSuite, Sage Intacct, Oracle, Workday, Adaptive Planning, Rippling, or similar ERP/FP&A platforms.\n\n - Experience supporting venture fundraising, investor relations, and Board reporting.\n\n - Deep understanding of SaaS metrics including ARR, burn multiple, CAC, gross margin, and cash runway.\n\n - Experience partnering closely with engineering organizations or evaluating infrastructure investments.\n\n - Experience building finance organizations from the ground up.\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nWHAT SUCCESS LOOKS LIKE:\n\n - Established a predictable monthly close process and executive financial reporting cadence.\n\n - Built a scalable budgeting and forecasting process used across every department.\n\n - Improved visibility into cash flow, runway, revenue, and company performance.\n\n - Implemented stronger operational processes across invoicing, collections, expense management, and financial controls.\n\n - Delivered investment analyses that influence hiring, infrastructure, product, and go-to-market decisions.\n\n - Evaluated and began implementing the ERP and financial systems needed to support Gray Swan’s next stage of growth.\n\n - Become a trusted strategic advisor to leadership while remaining deeply involved in day-to-day finance execution.\n \n \n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $170,000 - $260,000 plus performance based bonus and meaningful equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application.\n\n\n\n\n🔎 APPLICATION REVIEW. WE READ EVERYTHING; WE’LL RESPOND WITHIN 10 DAYS.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast."},{"id":"315e6de2-bae5-43c9-aafb-2e7187276a84","title":"Office Manager (PT)","department":"Operations","team":"Operations","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[],"publishedAt":"2026-08-06T16:41:56.738+00:00","isListed":true,"isRemote":false,"workplaceType":"OnSite","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/315e6de2-bae5-43c9-aafb-2e7187276a84","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/315e6de2-bae5-43c9-aafb-2e7187276a84/application","descriptionHtml":"Location: Pittsburgh, PA (On-site)
Employment Type: Part-Time (20 hours/week, 5 days/week)
Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
The Office Manager is the person who keeps our Pittsburgh office running smoothly.
This role combines hospitality, organization, and day-to-day operations. You'll ensure our team has what they need, visitors have a great experience, and the office remains an efficient, enjoyable place to work.
You'll work approximately 20 hours per week, with around four hours each day spent in the office supporting employees, coordinating vendors, and handling local errands as needed.
If you naturally notice what's missing before anyone else does, enjoy helping people, and take pride in creating great experiences, you'll thrive in this role.
Create a welcoming, professional experience for employees and visitors.
Manage office snacks, beverages, and common area supplies.
Coordinate and manage daily team lunches.
Maintain office equipment and supplies (excluding IT hardware and systems).
Welcome guests, coordinate visitor access, and prepare meeting spaces.
Submit and track building maintenance requests.
Coordinate deliveries, shipping, and local errands.
Maintain an organized, clean, and functional office environment.
Build relationships with vendors and building management.
Identify opportunities to improve office operations and employee experience.
You're hospitality-minded. You enjoy helping people and creating an environment where others feel welcome and supported.
You notice the details. You see what needs attention before someone has to ask.
You're organized. You can balance multiple priorities while keeping everything moving smoothly.
You take ownership. You don't wait for instructions—you solve problems and follow them through.
You're resourceful. You enjoy figuring things out and finding practical solutions.
You're dependable. People know they can count on you to keep things running.
Experience in office management, workplace operations, hospitality, executive support, customer service, or facilities coordination.
Excellent communication and interpersonal skills.
Strong organizational and time management abilities.
Comfort working independently in a fast-moving startup environment.
Ability to lift and move office supplies (up to approximately 25 lbs.) and complete occasional local errands.
Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
Our frontier lab business is Gray Swan's most strategic. We evaluate models for the leading AI labs before those models ship. This role owns the commercial side of those relationships end to end.
You will report to our SVP of Frontier Lab Safety and work alongside a Strategic Partnership Manager who owns technical scoping and delivery. You own the number: landing new lab accounts, converting first engagements into ongoing programs, and expanding accounts as their evaluation needs grow.
This is a small, high-trust market. A few dozen people worldwide decide how frontier AI gets evaluated, and they talk to each other. Credibility here is earned through technical fluency, discretion, and consistency, not volume outreach.
Own the full commercial cycle for a portfolio of frontier lab accounts: first conversation, scoping, pricing, contract, close.
Carry a quota spanning both new logos and expansion within existing accounts. Most of our growth comes from deepening engagements that already exist, so renewal and upsell are as central to the role as new business.
Set the commercial frame on engagements while our Strategic Partnership Manager and research team set the technical one, so that scopes are both sellable and deliverable.
Move deals through procurement, legal, and security review at organizations that take contracting extremely seriously, maintaining momentum across multi-month cycles.
Build relationships across research, safety, policy, and procurement functions. The champion and the signer are rarely the same person here.
Bring the field back inside: what labs and agencies are being asked to prove, what they are being asked to prove it against, and where our evaluation offering needs to go next.
Represent Gray Swan at the conferences, workshops, and standards conversations where this market is being defined.
5+ years closing complex six-figure-plus enterprise or professional services deals with long, consultative, multi-stakeholder cycles.
Enough fluency in AI safety and evaluation to hold a real conversation about model testing, red teaming, and agentic risk. You do not need to be a researcher, but you do need to be genuinely conversant with technical buyers.
Experience selling into or working alongside AI labs, research organizations, or government and regulatory bodies.
A record of growing accounts rather than only landing them: renewals, expansions, and multi-year programs you can speak to specifically.
Experience operating under NDA with pre-release or otherwise sensitive customer information.
Not a delivery role. Our Strategic Partnership Manager owns scope-to-milestone execution; you own the commercial relationship.
Not a broad enterprise territory. Our Account Executives cover financial services, healthcare, and insurance. Your accounts are frontier labs and some government evaluation bodies.
Not a management role. This is a senior individual contributor seat on a team we expect to grow.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Are energized by a market that did not exist three years ago and is being written as you sell into it.
Are discreet. You will be privy to sensitive commercial and research information.
Are motivated by ownership, accountability, and upside rather than rigid structure.
Would rather be the person a head of safety calls first than the person with the highest activity metrics.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $157k-$192k + commission ($314-$384k OTE) and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nOur frontier lab business is Gray Swan's most strategic. We evaluate models for the leading AI labs before those models ship. This role owns the commercial side of those relationships end to end.\n\nYou will report to our SVP of Frontier Lab Safety and work alongside a Strategic Partnership Manager who owns technical scoping and delivery. You own the number: landing new lab accounts, converting first engagements into ongoing programs, and expanding accounts as their evaluation needs grow.\n\nThis is a small, high-trust market. A few dozen people worldwide decide how frontier AI gets evaluated, and they talk to each other. Credibility here is earned through technical fluency, discretion, and consistency, not volume outreach.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Own the full commercial cycle for a portfolio of frontier lab accounts: first conversation, scoping, pricing, contract, close.\n\n - Carry a quota spanning both new logos and expansion within existing accounts. Most of our growth comes from deepening engagements that already exist, so renewal and upsell are as central to the role as new business.\n\n - Set the commercial frame on engagements while our Strategic Partnership Manager and research team set the technical one, so that scopes are both sellable and deliverable.\n\n - Move deals through procurement, legal, and security review at organizations that take contracting extremely seriously, maintaining momentum across multi-month cycles.\n\n - Build relationships across research, safety, policy, and procurement functions. The champion and the signer are rarely the same person here.\n\n - Bring the field back inside: what labs and agencies are being asked to prove, what they are being asked to prove it against, and where our evaluation offering needs to go next.\n\n - Represent Gray Swan at the conferences, workshops, and standards conversations where this market is being defined.\n\n\n\n\nWHO YOU ARE:\n\n - 5+ years closing complex six-figure-plus enterprise or professional services deals with long, consultative, multi-stakeholder cycles.\n\n - Enough fluency in AI safety and evaluation to hold a real conversation about model testing, red teaming, and agentic risk. You do not need to be a researcher, but you do need to be genuinely conversant with technical buyers.\n\n - Experience selling into or working alongside AI labs, research organizations, or government and regulatory bodies.\n\n - A record of growing accounts rather than only landing them: renewals, expansions, and multi-year programs you can speak to specifically.\n\n - Experience operating under NDA with pre-release or otherwise sensitive customer information.\n\n\n\n\nTHIS IS NOT …\n\n - Not a delivery role. Our Strategic Partnership Manager owns scope-to-milestone execution; you own the commercial relationship.\n\n - Not a broad enterprise territory. Our Account Executives cover financial services, healthcare, and insurance. Your accounts are frontier labs and some government evaluation bodies.\n\n - Not a management role. This is a senior individual contributor seat on a team we expect to grow.\n\n\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Are energized by a market that did not exist three years ago and is being written as you sell into it.\n\n - Are discreet. You will be privy to sensitive commercial and research information.\n\n - Are motivated by ownership, accountability, and upside rather than rigid structure.\n\n - Would rather be the person a head of safety calls first than the person with the highest activity metrics.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $157k-$192k + commission ($314-$384k OTE) and meaningful equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"f160a2ce-0f55-4843-a0f6-f27a8bc56a64","title":"Head of Biology ","department":"Red Team","team":"Red Team","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-03T00:36:42.145+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/f160a2ce-0f55-4843-a0f6-f27a8bc56a64","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/f160a2ce-0f55-4843-a0f6-f27a8bc56a64/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
Come build and lead Gray Swan's biology safety capability from the ground up, serving as the technical authority on biological misuse risk across red-teaming, evaluation, benchmarking, defenses, and safety infrastructure development. You'll play a critical role in reducing biological risks from frontier AI systems through partnerships with leading AI labs, translating deep biological expertise into scalable AI safety systems that help define the industry's standards for evaluating dangerous capabilities.
This is a rare opportunity to shape an entirely new technical function at one of the world's leading AI security companies, working at the intersection of synthetic biology, biosecurity, AI safety, and machine learning.
If you have PhD-level expertise in biosecurity, molecular biology, synthetic biology, microbiology, immunology, or a related field, significant experience with AI safety, biological risk assessment, or dual-use research, and a drive to reduce catastrophic AI risks, we'd love to hear from you.
Design and lead adversarial evaluations of frontier LLMs for biological misuse risks, including agent acquisition, pathogen characterisation and enhancement, biosecurity screening bypass, and emerging biotechnology capabilities across text, agentic, and multimodal systems.
Partner closely with machine learning engineers and AI researchers to translate biological expertise into technical requirements for scalable evaluation datasets, classifiers, guardrails, benchmarks, fine-tuned models, and automated red-teaming for both internal products and frontier AI lab partners.
Develop and maintain the B in Gray Swan's CBRN harm taxonomy, ensuring biological risk frameworks evolve alongside rapidly advancing model capabilities.
Produce clear technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, policymakers, and internal stakeholders.
Build, mentor, and lead a high-performing team of biology subject matter experts while establishing rigorous evaluation standards, quality processes, and scalable safety infrastructure.
Represent Gray Swan as the company's biology safety expert through collaborations with AI labs, biosecurity organizations, government partners, and the broader AI safety research community.
PhD in biology, particularly in microbiology, virology, synthetic biology, protein engineering, or a closely related discipline, with postdoctoral or equivalent research experience.
Deep understanding of biological misuse risks, dual-use research, pathogen biology, synthetic biology, or biosecurity.
Experience conducting adversarial evaluations, biological risk assessments, AI safety research, or developing safety datasets for frontier AI systems.
Familiarity with international biosecurity frameworks, dual-use governance, responsible biotechnology practices, and emerging AI safety standards.
Comfortable operating at the intersection of cutting-edge biology, machine learning, and AI security.
Thrive in ambiguous, fast-moving environments where you'll define strategy while building new systems from the ground up.
A builder who enjoys creating teams, processes, and technical infrastructure, not simply maintaining existing programs
Experience developing machine learning systems, biological safety classifiers, or evaluation pipelines for high-risk biological capabilities.
Hands-on experience with frontier AI model evaluations, red-teaming, prompt engineering, or AI capability benchmarking.
Experience working with government biosecurity organizations, frontier AI labs, or organizations focused on catastrophic biological risk.
Publications or significant contributions in AI safety, biosecurity, synthetic biology, or dual-use governance.
Strong programming or data science experience (Python, ML tooling, biological data analysis).
If you don't meet every qualification, we still encourage you to apply. We care more about your ability to solve important problems than checking every box.
Want visibility across the frontier of AI safety, helping evaluate multiple frontier models and working directly with leading AI labs.
Are excited to build the infrastructure that makes biological AI safety scalable.
Are motivated by reducing catastrophic risks from increasingly capable AI systems.
Enjoy turning cutting-edge scientific expertise into practical systems that improve AI safety.
Have a vision for what world-class biology safety should look like and are excited to build it.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $230,000 - $280,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\n\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nCome build and lead Gray Swan's biology safety capability from the ground up, serving as the technical authority on biological misuse risk across red-teaming, evaluation, benchmarking, defenses, and safety infrastructure development. You'll play a critical role in reducing biological risks from frontier AI systems through partnerships with leading AI labs, translating deep biological expertise into scalable AI safety systems that help define the industry's standards for evaluating dangerous capabilities.\n\nThis is a rare opportunity to shape an entirely new technical function at one of the world's leading AI security companies, working at the intersection of synthetic biology, biosecurity, AI safety, and machine learning.\n\nIf you have PhD-level expertise in biosecurity, molecular biology, synthetic biology, microbiology, immunology, or a related field, significant experience with AI safety, biological risk assessment, or dual-use research, and a drive to reduce catastrophic AI risks, we'd love to hear from you.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design and lead adversarial evaluations of frontier LLMs for biological misuse risks, including agent acquisition, pathogen characterisation and enhancement, biosecurity screening bypass, and emerging biotechnology capabilities across text, agentic, and multimodal systems.\n\n - Partner closely with machine learning engineers and AI researchers to translate biological expertise into technical requirements for scalable evaluation datasets, classifiers, guardrails, benchmarks, fine-tuned models, and automated red-teaming for both internal products and frontier AI lab partners.\n\n - Develop and maintain the B in Gray Swan's CBRN harm taxonomy, ensuring biological risk frameworks evolve alongside rapidly advancing model capabilities.\n\n - Produce clear technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, policymakers, and internal stakeholders.\n\n - Build, mentor, and lead a high-performing team of biology subject matter experts while establishing rigorous evaluation standards, quality processes, and scalable safety infrastructure.\n\n - Represent Gray Swan as the company's biology safety expert through collaborations with AI labs, biosecurity organizations, government partners, and the broader AI safety research community.\n\n\n\n\nWHO YOU ARE:\n\n - PhD in biology, particularly in microbiology, virology, synthetic biology, protein engineering, or a closely related discipline, with postdoctoral or equivalent research experience.\n\n - Deep understanding of biological misuse risks, dual-use research, pathogen biology, synthetic biology, or biosecurity.\n\n - Experience conducting adversarial evaluations, biological risk assessments, AI safety research, or developing safety datasets for frontier AI systems.\n\n - Familiarity with international biosecurity frameworks, dual-use governance, responsible biotechnology practices, and emerging AI safety standards.\n\n - Comfortable operating at the intersection of cutting-edge biology, machine learning, and AI security.\n\n - Thrive in ambiguous, fast-moving environments where you'll define strategy while building new systems from the ground up.\n\n - A builder who enjoys creating teams, processes, and technical infrastructure, not simply maintaining existing programs\n \n \n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience developing machine learning systems, biological safety classifiers, or evaluation pipelines for high-risk biological capabilities.\n\n - Hands-on experience with frontier AI model evaluations, red-teaming, prompt engineering, or AI capability benchmarking.\n\n - Experience working with government biosecurity organizations, frontier AI labs, or organizations focused on catastrophic biological risk.\n\n - Publications or significant contributions in AI safety, biosecurity, synthetic biology, or dual-use governance.\n\n - Strong programming or data science experience (Python, ML tooling, biological data analysis).\n\nIf you don't meet every qualification, we still encourage you to apply. We care more about your ability to solve important problems than checking every box.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Want visibility across the frontier of AI safety, helping evaluate multiple frontier models and working directly with leading AI labs.\n\n - Are excited to build the infrastructure that makes biological AI safety scalable.\n\n - Are motivated by reducing catastrophic risks from increasingly capable AI systems.\n\n - Enjoy turning cutting-edge scientific expertise into practical systems that improve AI safety.\n\n - Have a vision for what world-class biology safety should look like and are excited to build it.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\n\n\nCompensation: $230,000 - $280,000 plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast."},{"id":"d3e85b89-81fc-4c1e-8367-bdaa22f5d221","title":"Staff Product Designer","department":"Red Team","team":"Red Team","employmentType":"FullTime","location":"Remote (U.S. Only)","secondaryLocations":[],"publishedAt":"2026-09-01T19:20:30.190+00:00","isListed":true,"isRemote":true,"workplaceType":"Remote","address":{"postalAddress":{"addressCountry":"United States"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d3e85b89-81fc-4c1e-8367-bdaa22f5d221","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/d3e85b89-81fc-4c1e-8367-bdaa22f5d221/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..
We’re looking for a Staff Product Designer to join our small but mighty design team. You’ll work closely with the Arena Product team to build and grow the Gray Swan AI Arena. From collaborating with developers and marketing teams to translating complex technical workflows into clear, trustworthy, and refined product experiences, you’ll help shape how AI systems are tested, monitored, and secured.
This is a high ownership role. We care deeply about craft, but just as much about initiative. We’re looking for someone who can take a problem, run with it, collaborate cross functionally, and push the work to a high standard without waiting to be told what to do.
Design and improve Gray Swan’s Arena UI across web and mobile platforms
Own your work from end-to-end, from early concept sketches to production-ready specs
Translate complex technical workflows into clear, and intuitive user experiences.
Incorporate visual design and persuasive design principles to create joyful and engaging flows.
Build and maintain UI components, patterns, and visual standards in our design system
Collaborate with product, engineering, ML research, and GTM teams on cross-functional work
Contribute to ad hoc design needs as they arise: we all wear a few extra hats here!
6+ years’ professional experience in product UI/UX design, ideally in gamified consumer apps, bonus points for experience building tooling and/or chat interfaces
Able to balance the need of technical users with creating playful design
Proficient in modern design and prototyping tools
Solid grasp on user-centered design principles and usability testing methodologies
Detail-oriented with a knack for managing style guides and component libraries
Experience working at an early-stage startup
Understanding of AI safety principles or ethical considerations in AI systems
Some familiarity with front-end development or coding skills
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
Enjoy high-impact work. Your role will directly shape the experience of our early customers and set the tone for future growth
Embrace a collaborative, mission-focused team. You’ll work alongside passionate engineers, product leaders, and a supportive UX Lead
Lead with purpose: As we scale, you'll help formalize our design processes and co-lead design initiatives
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $205,000-$255,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\nWe're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for a Staff Product Designer to join our small but mighty design team. You’ll work closely with the Arena Product team to build and grow the Gray Swan AI Arena. From collaborating with developers and marketing teams to translating complex technical workflows into clear, trustworthy, and refined product experiences, you’ll help shape how AI systems are tested, monitored, and secured.\n\nThis is a high ownership role. We care deeply about craft, but just as much about initiative. We’re looking for someone who can take a problem, run with it, collaborate cross functionally, and push the work to a high standard without waiting to be told what to do.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Design and improve Gray Swan’s Arena UI across web and mobile platforms\n\n - Own your work from end-to-end, from early concept sketches to production-ready specs\n\n - Translate complex technical workflows into clear, and intuitive user experiences.\n\n - Incorporate visual design and persuasive design principles to create joyful and engaging flows.\n\n - Build and maintain UI components, patterns, and visual standards in our design system\n\n - Collaborate with product, engineering, ML research, and GTM teams on cross-functional work\n\n - Contribute to ad hoc design needs as they arise: we all wear a few extra hats here!\n\n\n\n\nWHO YOU ARE:\n\n - 6+ years’ professional experience in product UI/UX design, ideally in gamified consumer apps, bonus points for experience building tooling and/or chat interfaces\n\n - Able to balance the need of technical users with creating playful design\n\n - Proficient in modern design and prototyping tools\n\n - Solid grasp on user-centered design principles and usability testing methodologies\n\n - Detail-oriented with a knack for managing style guides and component libraries\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience working at an early-stage startup\n\n - Understanding of AI safety principles or ethical considerations in AI systems\n\n - Some familiarity with front-end development or coding skills\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - Enjoy high-impact work. Your role will directly shape the experience of our early customers and set the tone for future growth\n\n - Embrace a collaborative, mission-focused team. You’ll work alongside passionate engineers, product leaders, and a supportive UX Lead\n\n - Lead with purpose: As we scale, you'll help formalize our design processes and co-lead design initiatives\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $205,000-$255,000 plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."},{"id":"32821e39-a375-4ca6-8409-9383298e2f0d","title":"Sales Operations Associate ","department":"Sales","team":"Sales","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[],"publishedAt":"2026-09-14T19:06:35.999+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/32821e39-a375-4ca6-8409-9383298e2f0d","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/32821e39-a375-4ca6-8409-9383298e2f0d/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for enterprise teams deploying AI.
We're a team of approximately 50 people, well-funded and growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.
We’re looking for a Sales Operations Associate to build the systems, processes, and operational infrastructure that enable our sales organization to scale. This is a highly cross-functional, back-office role for someone who loves creating structure, solving operational problems, and making teams more efficient. You’ll work closely with Sales, Legal, Compliance, Finance, and Accounting to improve processes across the full sales lifecycle—from pre-sales and contracting through delivery, invoicing, and commissions. This role also has the opportunity to evolve as the company grows, with the possibility to take on additional Sales and Revenue Operations initiatives.
Build and improve scalable systems and processes across the sales lifecycle, including pre-sales, contracting, post-sales, project/deliverable tracking, and internal handoffs.
Own the operational side of our deal desk, coordinating contracts, SOWs, security questionnaires, vendor onboarding, RFPs, and other deal-related requirements with the appropriate internal teams.
Partner with Sales, Legal, Compliance, Finance, and Accounting to ensure the right stakeholders are engaged at the right time and that processes move efficiently.
Manage the sales-side invoice process and execute commission plans for quota-carrying team members.
Manage and optimize our CRM (HubSpot), reporting, workflows, and automations while continuously looking for opportunities to eliminate manual work.
Lead cross-functional projects and create playbooks, documentation, and processes that bring greater structure and scalability to the organization.
You’re a strong project manager who can take an ambiguous problem, create structure, coordinate stakeholders, and drive it through to completion.
You think in terms of workflows and flow charts, and have used tools like Zapier, n8n, etc. to build automations based on these.
You’re highly organized and detail-oriented, with strong judgment around what you can solve independently and when to pull in Legal, Finance, Compliance, or other teams.
You have hands-on experience working with sales teams and deal cycles.
You’re a process-minded problem solver who naturally asks, “How can we make this easier, more efficient, and more scalable?”
You’re comfortable working across multiple functions and managing several priorities at once in a fast-moving environment.
You have experience with CRM systems and reporting, and you’re comfortable learning and improving systems rather than simply maintaining them.
You’re a hands-on generalist who isn’t afraid to jump into the details, execute manually when necessary, and then find a way to automate it.
Experience with HubSpot or another CRM, including workflows, reporting, data management, and automation.
Experience in Sales Operations, Revenue Operations, Deal Desk, Business Operations, Sales, or a similar cross-functional role.
Experience working with Sales, Legal, Compliance, Finance, or Accounting on contracts, security requirements, vendor onboarding, or related processes.
Experience building contracting processes, deal desk workflows, playbooks, or other operational frameworks from the ground up.
Experience supporting commission administration, RFPs, security questionnaires, or sales-side invoicing processes.
Experience identifying opportunities for automation and using technology to streamline repetitive operational work.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You genuinely enjoy problem solving and get satisfaction from making the organization run better behind the scenes.
You’re energized by creating structure where there isn’t much structure yet, and you’re comfortable figuring things out as you go.
You’re naturally curious and enjoy learning how different parts of a business work together.
You have a strong sense of ownership and don’t wait to be told exactly what to do when you see something that needs fixing.
You’re a generalist at heart—you like having your hands in a variety of projects rather than being narrowly focused on one system or function.
You want a role that can grow with the company and are excited by the opportunity to shape what Sales Operations looks like as we scale.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $136,500 - $163,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assessment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3 references that you provide.
📃 Offer. If it’s mutual, we move fast.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for enterprise teams deploying AI.\n\n\n\nWe're a team of approximately 50 people, well-funded and growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nWe’re looking for a Sales Operations Associate to build the systems, processes, and operational infrastructure that enable our sales organization to scale. This is a highly cross-functional, back-office role for someone who loves creating structure, solving operational problems, and making teams more efficient. You’ll work closely with Sales, Legal, Compliance, Finance, and Accounting to improve processes across the full sales lifecycle—from pre-sales and contracting through delivery, invoicing, and commissions. This role also has the opportunity to evolve as the company grows, with the possibility to take on additional Sales and Revenue Operations initiatives.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Build and improve scalable systems and processes across the sales lifecycle, including pre-sales, contracting, post-sales, project/deliverable tracking, and internal handoffs.\n\n - Own the operational side of our deal desk, coordinating contracts, SOWs, security questionnaires, vendor onboarding, RFPs, and other deal-related requirements with the appropriate internal teams.\n\n - Partner with Sales, Legal, Compliance, Finance, and Accounting to ensure the right stakeholders are engaged at the right time and that processes move efficiently.\n\n - Manage the sales-side invoice process and execute commission plans for quota-carrying team members.\n\n - Manage and optimize our CRM (HubSpot), reporting, workflows, and automations while continuously looking for opportunities to eliminate manual work.\n\n - Lead cross-functional projects and create playbooks, documentation, and processes that bring greater structure and scalability to the organization.\n\n\n\n\nWHO YOU ARE:\n\n - You’re a strong project manager who can take an ambiguous problem, create structure, coordinate stakeholders, and drive it through to completion.\n\n - You think in terms of workflows and flow charts, and have used tools like Zapier, n8n, etc. to build automations based on these.\n\n - You’re highly organized and detail-oriented, with strong judgment around what you can solve independently and when to pull in Legal, Finance, Compliance, or other teams.\n\n - You have hands-on experience working with sales teams and deal cycles.\n\n - You’re a process-minded problem solver who naturally asks, “How can we make this easier, more efficient, and more scalable?”\n\n - You’re comfortable working across multiple functions and managing several priorities at once in a fast-moving environment.\n\n - You have experience with CRM systems and reporting, and you’re comfortable learning and improving systems rather than simply maintaining them.\n\n - You’re a hands-on generalist who isn’t afraid to jump into the details, execute manually when necessary, and then find a way to automate it.\n\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience with HubSpot or another CRM, including workflows, reporting, data management, and automation.\n\n - Experience in Sales Operations, Revenue Operations, Deal Desk, Business Operations, Sales, or a similar cross-functional role.\n\n - Experience working with Sales, Legal, Compliance, Finance, or Accounting on contracts, security requirements, vendor onboarding, or related processes.\n\n - Experience building contracting processes, deal desk workflows, playbooks, or other operational frameworks from the ground up.\n\n - Experience supporting commission administration, RFPs, security questionnaires, or sales-side invoicing processes.\n\n - Experience identifying opportunities for automation and using technology to streamline repetitive operational work.\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You genuinely enjoy problem solving and get satisfaction from making the organization run better behind the scenes.\n\n - You’re energized by creating structure where there isn’t much structure yet, and you’re comfortable figuring things out as you go.\n\n - You’re naturally curious and enjoy learning how different parts of a business work together.\n\n - You have a strong sense of ownership and don’t wait to be told exactly what to do when you see something that needs fixing.\n\n - You’re a generalist at heart—you like having your hands in a variety of projects rather than being narrowly focused on one system or function.\n\n - You want a role that can grow with the company and are excited by the opportunity to shape what Sales Operations looks like as we scale.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $136,500 - $163,000 plus performance based bonus and meaningful equity package\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n\n\nTYPICAL INTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assessment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n"},{"id":"0471ff48-7092-4a79-bcb3-a28481011f48","title":"General Interest ","department":"Gray Swan","team":"Gray Swan","employmentType":"FullTime","location":"Remote U.S. or Pittsburgh, PA","secondaryLocations":[],"publishedAt":"2026-09-17T22:32:35.695+00:00","isListed":true,"isRemote":null,"workplaceType":null,"address":null,"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/0471ff48-7092-4a79-bcb3-a28481011f48","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/0471ff48-7092-4a79-bcb3-a28481011f48/application","descriptionHtml":"Interested in joining Gray Swan, but don't see a role that is a perfect match? Submit your application here and the team will reach out if we have a fit.
","descriptionPlain":"Interested in joining Gray Swan, but don't see a role that is a perfect match? Submit your application here and the team will reach out if we have a fit. "},{"id":"4548dd3b-fc48-4252-8106-0ae28c3c9aad","title":"Senior Manager, Engineering ","department":"Software Engineering","team":"Software Engineering","employmentType":"FullTime","location":"Pittsburgh","secondaryLocations":[],"publishedAt":"2026-09-18T17:17:53.348+00:00","isListed":true,"isRemote":true,"workplaceType":"Hybrid","address":{"postalAddress":{"addressRegion":"Pennsylvania","addressCountry":"United States","addressLocality":"Pittsburgh"}},"jobUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/4548dd3b-fc48-4252-8106-0ae28c3c9aad","applyUrl":"https://jobs.ashbyhq.com/Gray%20Swan%20AI/4548dd3b-fc48-4252-8106-0ae28c3c9aad/application","descriptionHtml":"Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.
We're a team of approximately 60 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.
Gray Swan is looking for an Engineering Manager, Enterprise to lead the team responsible for building and scaling the systems that power our AI security platform. You'll combine strong technical judgment with people leadership to help design the enterprise experience, including infrastructure, backend services, and cloud architecture that enable Gray Swan to build AI systems and for customers to safely deploy frontier AI models at scale.
This role is ideal for an engineering leader who enjoys solving complex infrastructure challenges while building and developing a high-performing team. You'll work closely with machine learning engineers, product engineers, and security researchers to ensure our platform remains fast, resilient, secure, and scalable as we grow.
You'll have significant ownership over foundational systems, technical strategy, and team development. As one of the leaders shaping Gray Swan's infrastructure organization, you'll have the opportunity to influence architecture, engineering practices, and how we build and operate systems in a rapidly evolving AI startup.
Lead, mentor, and develop a team of infrastructure engineers, creating a culture of ownership, technical excellence, and continuous improvement.
Set technical direction and priorities for enterprise solutions in partnership with engineering leadership and other technical teams.
Oversee the design, development, and operation of highly available backend services and distributed systems that power Gray Swan's AI security platform.
Guide the team in owning and scaling cloud infrastructure across Kubernetes, AWS, GCP, Azure, networking, storage, and compute.
Drive the development of internal platform services, infrastructure tooling, and systems that improve developer productivity and reliability.
Establish and improve engineering practices around observability, monitoring, incident response, deployment, and operational excellence.
Partner closely with machine learning, security, and product engineering teams to build infrastructure capable of supporting increasingly complex AI workloads.
Identify and address opportunities to improve system performance, reliability, scalability, and infrastructure efficiency.
Help define long-term architecture and technical strategy while balancing immediate product and engineering priorities.
Participate in hiring and help build a world-class infrastructure engineering organization.
Provide technical guidance during complex production incidents and ensure the team learns from failures through effective post-incident reviews.
Communicate infrastructure strategy, tradeoffs, risks, and priorities clearly across engineering and company leadership.
7+ years of experience building enterprise solutions with experience implementing backend infrastructure or distributed systems in production environments.
2+ years of experience managing, mentoring, or leading software engineering teams.
Strong technical background in infrastructure, distributed systems, backend engineering, or platform engineering.
Strong programming experience in C/C++, Go, Python, Rust, Java, or a similar language.
Experience operating production services on Kubernetes and modern cloud platforms such as AWS, GCP, and Azure.
Deep understanding of networking, distributed systems, containers, service orchestration, and scalable architectures.
Experience designing and operating APIs, microservices, asynchronous systems, and event-driven architectures.
Strong understanding of reliability, observability, security, and performance at scale.
Comfortable diving into complex technical problems and debugging production systems alongside your team.
A strong people leader who enjoys coaching engineers, providing feedback, and helping individuals grow.
Able to balance technical depth with effective delegation and team leadership.
Excited to work in a fast-moving startup where you will have significant ownership and ambiguity.
Experience managing infrastructure or platform teams supporting machine learning or LLM workloads.
Experience with infrastructure-as-code tools such as Terraform.
Experience with Kafka, Redis, PostgreSQL, ClickHouse, or similar distributed data systems.
Experience building internal developer platforms or platform engineering organizations.
Knowledge of cloud security, infrastructure hardening, or zero-trust architectures.
Experience scaling infrastructure through a period of rapid company or product growth.
Previous experience at a high-growth startup or building products from zero to one.
Interest in AI safety, cybersecurity, or adversarial machine learning.
If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.
You lead from the front. You're technically curious, comfortable getting into the details when needed, and know how to empower engineers without becoming a bottleneck.
You build great teams. You care deeply about developing engineers, creating a strong team culture, and giving people the ownership and autonomy they need to do their best work.
You think at scale. You enjoy designing resilient infrastructure, making thoughtful architectural decisions, and building systems that are secure, observable, and built to grow.
You balance strategy with execution. You can zoom out to define long-term technical direction while staying close enough to the work to help the team navigate difficult technical problems.
You collaborate across disciplines. You work effectively with machine learning engineers, security researchers, and product teams, understanding that great infrastructure enables everyone else to move faster.
You're excited by our mission and startup environment. You enjoy moving quickly, adapting to change, and helping build the infrastructure foundation for the future of secure AI.
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.
Compensation: $255,000 - $315,000 plus performance based bonus and meaningful equity package
Benefits:
401k with up to 4% matching
28 days annual leave (vacation + holidays)
Health, dental, and vision coverage
Catered lunches (Pittsburgh office)
Flexible work arrangements
Visa sponsorship available for exceptional candidates
🔎 Application review. We read everything; we’ll respond within 10 days.
🗣 Recruiter Screen. We learn about you; you learn about us.
🧑💻 Technical interview or Hiring Manager Interview.
💻 Role related assesment
🗣 Experience & culture interview
😇 Reference checks. We’ll reach out to 3-5 references that you provide.
📃 Offer. If it’s mutual, we move fast.
Submit your resume, link to your portfolio, and answer the questions on the application.
","descriptionPlain":"ABOUT GRAY SWAN\n\nGray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.\n\n\n\nWe're a team of approximately 60 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.\n\nLearn more about how we work https://www.grayswan.ai/about.\n\n\n\n\nTHE ROLE\n\nGray Swan is looking for an Engineering Manager, Enterprise to lead the team responsible for building and scaling the systems that power our AI security platform. You'll combine strong technical judgment with people leadership to help design the enterprise experience, including infrastructure, backend services, and cloud architecture that enable Gray Swan to build AI systems and for customers to safely deploy frontier AI models at scale.\n\n\n\nThis role is ideal for an engineering leader who enjoys solving complex infrastructure challenges while building and developing a high-performing team. You'll work closely with machine learning engineers, product engineers, and security researchers to ensure our platform remains fast, resilient, secure, and scalable as we grow.\n\n\n\nYou'll have significant ownership over foundational systems, technical strategy, and team development. As one of the leaders shaping Gray Swan's infrastructure organization, you'll have the opportunity to influence architecture, engineering practices, and how we build and operate systems in a rapidly evolving AI startup.\n\n\n\n\nWHAT YOU’LL DO:\n\n - Lead, mentor, and develop a team of infrastructure engineers, creating a culture of ownership, technical excellence, and continuous improvement.\n\n - Set technical direction and priorities for enterprise solutions in partnership with engineering leadership and other technical teams.\n\n - Oversee the design, development, and operation of highly available backend services and distributed systems that power Gray Swan's AI security platform.\n\n - Guide the team in owning and scaling cloud infrastructure across Kubernetes, AWS, GCP, Azure, networking, storage, and compute.\n\n - Drive the development of internal platform services, infrastructure tooling, and systems that improve developer productivity and reliability.\n\n - Establish and improve engineering practices around observability, monitoring, incident response, deployment, and operational excellence.\n\n - Partner closely with machine learning, security, and product engineering teams to build infrastructure capable of supporting increasingly complex AI workloads.\n\n - Identify and address opportunities to improve system performance, reliability, scalability, and infrastructure efficiency.\n\n - Help define long-term architecture and technical strategy while balancing immediate product and engineering priorities.\n\n - Participate in hiring and help build a world-class infrastructure engineering organization.\n\n - Provide technical guidance during complex production incidents and ensure the team learns from failures through effective post-incident reviews.\n\n - Communicate infrastructure strategy, tradeoffs, risks, and priorities clearly across engineering and company leadership.\n \n\n\nWHO YOU ARE:\n\n - 7+ years of experience building enterprise solutions with experience implementing backend infrastructure or distributed systems in production environments.\n\n - 2+ years of experience managing, mentoring, or leading software engineering teams.\n\n - Strong technical background in infrastructure, distributed systems, backend engineering, or platform engineering.\n\n - Strong programming experience in C/C++, Go, Python, Rust, Java, or a similar language.\n\n - Experience operating production services on Kubernetes and modern cloud platforms such as AWS, GCP, and Azure.\n\n - Deep understanding of networking, distributed systems, containers, service orchestration, and scalable architectures.\n\n - Experience designing and operating APIs, microservices, asynchronous systems, and event-driven architectures.\n\n - Strong understanding of reliability, observability, security, and performance at scale.\n\n - Comfortable diving into complex technical problems and debugging production systems alongside your team.\n\n - A strong people leader who enjoys coaching engineers, providing feedback, and helping individuals grow.\n\n - Able to balance technical depth with effective delegation and team leadership.\n\n - Excited to work in a fast-moving startup where you will have significant ownership and ambiguity.\n\n\n\n\nBONUS POINTS IF YOU HAVE:\n\n - Experience managing infrastructure or platform teams supporting machine learning or LLM workloads.\n\n - Experience with infrastructure-as-code tools such as Terraform.\n\n - Experience with Kafka, Redis, PostgreSQL, ClickHouse, or similar distributed data systems.\n\n - Experience building internal developer platforms or platform engineering organizations.\n\n - Knowledge of cloud security, infrastructure hardening, or zero-trust architectures.\n\n - Experience scaling infrastructure through a period of rapid company or product growth.\n\n - Previous experience at a high-growth startup or building products from zero to one.\n\n - Interest in AI safety, cybersecurity, or adversarial machine learning.\n\n\n\nIf you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.\n\n\n\n\n\n\n\nYOU’LL THRIVE HERE IF YOU:\n\n - You lead from the front. You're technically curious, comfortable getting into the details when needed, and know how to empower engineers without becoming a bottleneck.\n\n - You build great teams. You care deeply about developing engineers, creating a strong team culture, and giving people the ownership and autonomy they need to do their best work.\n\n - You think at scale. You enjoy designing resilient infrastructure, making thoughtful architectural decisions, and building systems that are secure, observable, and built to grow.\n\n - You balance strategy with execution. You can zoom out to define long-term technical direction while staying close enough to the work to help the team navigate difficult technical problems.\n\n - You collaborate across disciplines. You work effectively with machine learning engineers, security researchers, and product teams, understanding that great infrastructure enables everyone else to move faster.\n\n - You're excited by our mission and startup environment. You enjoy moving quickly, adapting to change, and helping build the infrastructure foundation for the future of secure AI.\n\n\n\n\nWHAT WE OFFER:\n\nWe offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.\n\nCompensation: $255,000 - $315,000 plus performance based bonus and meaningful equity package\n\n\n\nBenefits:\n\n - 401k with up to 4% matching\n\n - 28 days annual leave (vacation + holidays)\n\n - Health, dental, and vision coverage\n\n - Catered lunches (Pittsburgh office)\n\n - Flexible work arrangements\n\n - Visa sponsorship available for exceptional candidates\n \n \n\n\nINTERVIEW PROCESS\n\n🔎 Application review. We read everything; we’ll respond within 10 days.\n\n🗣 Recruiter Screen. We learn about you; you learn about us.\n\n🧑💻 Technical interview or Hiring Manager Interview.\n\n💻 Role related assesment\n\n🗣 Experience & culture interview\n\n😇 Reference checks. We’ll reach out to 3-5 references that you provide.\n\n📃 Offer. If it’s mutual, we move fast.\n\n\n\n\nHOW TO APPLY\n\nSubmit your resume, link to your portfolio, and answer the questions on the application."}],"apiVersion":"1"}