Staff Software Engineer, AI Developer Tooling

Staff Software Engineer, AI Developer Tooling About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the Role You’ll own AI-assisted coding within Sentry’s Platform Engineering organization, building the systems and workflows AI coding agents need to contribute reliably to our codebase. Your work will span engineering teams, with Developer Infrastructure as your home base. Your first focus will be making internal developer systems accessible to agents. Many workflows currently depend on human interaction through a UI. You’ll identify the most valuable gaps, expose those capabilities through APIs, and connect tools such as Claude Code to complete development workflows. From there, you’ll improve the quality of AI-generated pull requests and automate recurring engineering work, including dependency upgrades, minor bug fixes, and maintenance. You’ll build the context and execution environment agents need: relevant repository information, tools and permissions, state management, tests, logs, recovery mechanisms, and evaluations. You’ll partner with engineers across Sentry to understand where agents succeed, where they fail, and which changes improve the development process. This role combines technical direction with hands‑on implementation, from choosing the problems to solve through building, measuring, and improving the solutions. This role is based in San Francisco, with three days per week in the office to work closely with Platform teams and engineering leadership. What You’ll Do Set priorities for AI-assisted development at Sentry, using engineer feedback and workflow data to identify where agents would provide the most value. Make internal developer systems accessible through APIs and build integrations enabling agents to complete workflows across those systems. Build context systems and agent execution tooling, including tool access, permissions, checkpoints, retries, and logging. Develop automated checks, evaluations, and feedback loops to improve the correctness, maintainability, and review readiness of AI-generated pull requests. Automate recurring work such as security dependency upgrades, minor bug fixes, and routine maintenance. Improve supporting developer workflows, including issue triage and CI/CD, where they limit agent effectiveness or create repetitive work for engineers. Lead changes across engineering teams, build agreement on priorities, and measure whether the tools reduce manual work and improve delivery. How You Work You’ve used AI coding agents on real development work and have informed views on their strengths, limitations, and failure modes. You bring structure to ambiguous problems, choose a practical starting point, and follow through on delivery. You move comfortably between infrastructure, backend systems, and developer tooling. You know when to build, integrate an existing tool, involve another team, or stop work with limited value. You combine data with direct feedback from engineers to assess whether a solution improves their work. You explain technical tradeoffs clearly and build alignment across teams and senior leadership. Qualifications 10+ years of software engineering experience, including hands‑on ownership of production systems. Experience building developer tools, infrastructure, or automation used by engineering teams, such as CI/CD systems, internal APIs, code review tooling, or agent workflows. Hands‑on experience using AI coding tools and agents, with an understanding of how context, tool access, and validation affect their output. Prior machine learning experience is not required. Strong software engineering and system design fundamentals, including experience building reliable integrations across systems. A track record of leading cross‑team technical initiatives from problem definition through implementation and adoption. Clear written and verbal communication, including explaining technical decisions and recommendations to senior engineering leaders. Nice to Have Experience building agent harnesses, context systems, evaluations, or automated pull request workflows. Experience with code review tooling, static analysis, or automated testing. Experience measuring and improving developer experience or engineering productivity. Experience with large‑scale distributed systems or monolith decomposition. Public contributions to developer tooling or AI‑assisted development projects. The base salary range that Sentry reasonably expects to pay for this position is $220,000 to $400,000 USD,plus an annual performance bonus of up to 15% of base salary. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job‑related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs. Equal Opportunity at Sentry Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally‑protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open‑source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible. Invest in your future with company match! (USandCanadaonly) Because you can never be too prepared. Commuter Stipend You shouldn't have to pay to get to work. Professional Development Stipend Keep your skills sharp. You'll need them. Stay healthy, stay happy, do yoga or something. Charitable Matching Program You're a good person. We like that. Flexible PTO You work, we pay. You take time off, we still pay. #J-18808-Ljbffr Jobleads-US