Staff Software Engineer (Artificial Intelligence Platform)

• 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
• 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 smaller one, or one we trained, and revisit that as cost and capability shift
• Leverage Sentry’s novel (and massive) dataset of errors, spans, and profiles
• Own major AI initiatives end to end, alongside the developers and product teams shipping them
• Run what you ship in production and debug it with Sentry

Benefits

• Competitive Compensation + Equity
• Medical, Dental, Vision Insurance
• Commuter Stipend
• Professional Development Stipend
• Health & Wellness Benefits
• Charitable Matching Program
• Flexible PTO
• Paid Parental Leave
• 401k Plan

• Enjoy building things. You will have the opportunity to join the AI/ML team as one of its foundational members
• You have strong opinions on agent design and have changed at least one in the last year
• You write solid production Python
• You’ve owned a system or component and led work across multiple engineers and teams, with a design doc people actually read
• You’ve shipped an LLM-backed system people depended on, and can tell us what broke
• You write clear technical documentation, mentor other engineers, and present to technical audiences
• Are driven by impact and enjoy working on high-stakes, high-visibility projects
• You’ve trained or fine-tuned models when it was the right call, and you know when it isn’t
• Thrive in cross-functional teams and enjoy building features alongside developers and product teams