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 This isn’t a typical engineering role. You won’t be embedded in a single product team or siloed in one product area. Instead, you’ll sit within Platform Engineering, own the AI-assisted coding domain, and work across all of engineering at Sentry, focused specifically on how AI coding agents participate in our software development lifecycle. For AI coding agents to work well in our repo, the internal systems they depend on need to be accessible via API, not locked behind UIs that require human interaction. Right now, many of those systems aren’t agent-ready. You’ll audit and prioritize that gap, expose those systems programmatically, and build the connections that let tools like Claude Code operate on them end-to-end. From there, the scope expands to improving the quality of AI-generated pull requests and automating the engineering work that’s important but consistently deprioritized. You will look from context engineering standpoint to see what to send to our model; you will look from harness engineering standpoint to see the tools it can use, the permissions it has, the state it carries forward, the tests it has to pass, the logs you capture, the retries, checkpoints, guardrails, and evals. You’ll work closely with the dev infrastructure team as your home base, then collaborate across every product team coding in our repo once the tooling foundation is in place. It’s a broad role with real impact, and the work you do will directly change how Sentry engineers ship software. WHAT YOU’LL DO - Audit Sentry’s internal developer systems and make them API-ready for AI agents. You’ll prioritize and drive the work of exposing those systems programmatically, and build the connections that allow agents to operate on them end-to-end. - Build the harness tooling, context systems, and feedback loops that help agents generate high-quality, repository-aware pull requests, including automated pre-review checks and PR quality measurement tailored to Sentry’s codebase. - Automate high-volume, low-priority engineering work: security dependency upgrades, minor bug fixes, and routine maintenance, so engineers can focus on higher-value work. - Design and build internal tools that make engineering more effective: productivity dashboards, AI-assisted issue triage, CI/CD optimizations, and tooling that reduces toil. - Identify and remove organizational friction. Use data and direct observation to find where engineering is slowing down, recommend solutions to senior leadership, and build cross-team buy-in for changes. YOU’LL LOVE THIS JOB IF YOU… - You’re passionate about AI coding tools and curious about how to make them better. You follow the space closely, have opinions about what works, and want to be at the frontier of how AI participates in real-world software development. - You’re high agency. You don’t wait for permission. When you see a problem, you figure out the right solution and make it happen. You’re comfortable with ambiguity, can structure your own work, and know when to build it yourself, when to delegate, and when to say “this isn’t worth doing.” - You’ve seen enough systems and codebases to pattern-match quickly. You can move between infrastructure, backend, and developer tooling without friction, and you bring seasoned judgment to technical decisions. - You’re metric-driven but not metric-obsessed. You use data to make good decisions, and you know the best insights sometimes come from talking directly to the engineers feeling the pain. - You thrive on variety. You enjoy the pace of “figure this out and build it, then move to something completely different,” and you can shift b