Prepper

Staff Software Engineer, AI Platform

Sentry·San Francisco, California·Remote·Posted 22 September 2026

About the role

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 Sentry already sees the moment software breaks: the error, the trace, the replay, the commit that caused it. Seer, our AI debugger, uses all of that to figure out what went wrong and how to fix it. We're looking for a Staff engineer to help decide how that system should evolve as models improve every few months. Some of what we build today will be obsolete by next spring. Part of the job is knowing which parts, and building the rest to last. IN THIS ROLE YOU WILL - Build state-of-the-art agentic AI systems to triage, debug, and solve real production issues - Set technical direction for how our agents get context, use tools, and decide when they're done - Build the evals that tell us whether a new model or prompt actually helped, fast enough that people use them - Decide when to use a frontier model, a…

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