Staff Software Engineer (AI Developer Tooling)

Join Sentry as a Staff Software Engineer (AI Developer Tooling) and play a crucial role in shaping the future of software development. In this unique position, you will work across all engineering teams, focusing on the integration of AI coding agents into our software development lifecycle. You will audit and prioritize internal developer systems, build connections for AI agents, and automate low-priority engineering tasks. This role offers a competitive compensation package, flexible PTO, and the opportunity to make a significant impact on how Sentry engineers ship software.

• Auditing and prioritizing Sentry’s internal developer systems to make them API-ready for AI agents, and building the connections that allow agents to operate on them end-to-end.
• Building 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.
• Automating high-volume, low-priority engineering work, such as security dependency upgrades, minor bug fixes, and routine maintenance, so engineers can focus on higher-value work.

• 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 between strategic and hands-on work without losing momentum
• 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’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’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’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 communicate clearly and can influence without authority. You work across team boundaries, present recommendations to senior leadership, and build buy-in for your ideas. People listen because you’ve done the work to understand things deeply
• Experience with large-scale distributed systems or monolith decomposition (nice to have)
• Strong software and system design fundamentals
• Experience building tools or workflows that improve how developers or AI agents work. This could be CI/CD or dev infra experience, or it could be AI harness tooling, AI-first coding workflows, or public contributions in this space. We’re open to a range of backgrounds
• 10+ years of software engineering experience
• Genuine curiosity and hands-on experience with AI coding tools and agents. Prior machine learning experience isn’t required
• Prior work on developer experience or engineering productivity programs (nice to have)
• Familiarity with code review tooling, static analysis, or automated PR pipelines (nice to have)
• Excellent written and verbal communication; comfortable presenting to senior technical leadership
• A track record of driving cross-team technical initiatives to completion