ABOUT THE TEAM Security is at the foundation of OpenAI’s mission to ensure that artificial general intelligence benefits all of humanity. The Security team protects OpenAI’s technology, people, and products. We are technical in what we build but are operational in how we do our work, and are committed to supporting all products and research at OpenAI. Our Security team tenets include: prioritizing for impact, enabling researchers, preparing for future transformative technologies, and engaging a robust security culture. ABOUT THE ROLE We’re seeking an exceptional Principal-level Offensive Security Engineer focused on deep, hands-on penetration testing of OpenAI’s agent-powered products, infrastructure, and model-integrated application surfaces. You’ll assess complex systems end to end, identify realistic vulnerabilities, validate exploitability and impact, and partner closely with engineering teams to drive durable fixes. This role will be primarily focused on continuously testing our agent-powered products like Codex and Operator. These systems are uniquely valuable targets because they’re rapidly evolving, can perform sensitive actions on behalf of users, and have large, diverse attack surfaces. You will play a crucial role in securing our agents by finding vulnerabilities that emerge from the interactions between the applications, infrastructure, tools, and models that power them. You’ll have the chance to not only find vulnerabilities, but actively drive their resolution, build reusable testing approaches, automate offensive security workflows with cutting-edge technologies, and use your attacker perspective to improve the security of OpenAI’s products. IN THIS ROLE YOU WILL: - Conduct deep penetration tests of OpenAI’s agent-powered products, including web applications, APIs, cloud services, identity and authorization flows, CI/CD systems, and model-integrated product surfaces. - Continuously hunt for exploitable vulnerabilities in the interactions between the applications, infrastructure, tools, and models that power our agentic products. - Perform code review, architecture review, and hands-on exploitation to validate risk and identify subtle or novel failure modes. - Produce clear, actionable findings with reproduction steps, exploitability analysis, impact assessment, and practical remediation guidance. - Partner directly with engineering teams to drive fixes, validate remediation, and improve secure design patterns across agentic products. - Build tools, test harnesses, and automation to scale penetration testing across rapidly evolving product surfaces. - Leverage advanced automation and OpenAI technologies to optimize your offensive security work. - Share attacker-informed insights with security and engineering teams to improve threat models, mitigations, and defensive coverage. YOU MIGHT THRIVE IN THIS ROLE IF YOU HAVE: - 7+ years of hands-on penetration testing, product security assessment, application security, cloud security assessment, or equivalent offensive security experience. - Deep expertise finding, exploiting, documenting, and helping remediate vulnerabilities in complex production systems. - Experience performing offensive security assessments of modern technology products, including web applications, APIs, cloud infrastructure, identity systems, CI/CD pipelines, and distributed services. - Experience designing, developing, or assessing the security of AI-powered systems. - Experience finding, exploiting, and mitigating common vulnerabilities in AI systems, including prompt injection, confused deputies, unsafe tool use, and dynamically generated UI components. - Exceptional skill in code review to identify novel and subtle vulnerabilities. - Proven experience performing offensive security assessments in at least one hyperscaler cloud environment. Azure experience is preferred. - Demonstrated mastery assessing complex technology stacks, including: - Highly customized Kubernetes clusters - Container environments - CI/CD pipelines - GitHub security - macOS and Linux operating systems - Data science tooling and environments - Python-based web services - React-based frontend applications - Strong intuitive understanding of trust boundaries and risk assessment in dynamic contexts. - Excellent coding skills, capable of writing robust tools and automation for offensive security testing. - Ability to communicate complex technical concepts effectively through clear reports, practical remediation guidance, and compelling technical storytelling. - Proven track record of not just finding vulnerabilities, but actively contributing to solutions in complex codebases. BONUS POINTS: - Background or expertise in AI or data science. - Prior experience working in tech startups or fast-paced technology environments. - Experience in related disciplines such as Software Engineering, Product Security, Application Security, Detection Engineering, Site Reliability Engineering, Security Engineering, or IT Infrastructure. About OpenAI OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity. We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic. For additional information, please see OpenAI’s Affirmative Action a