Staff / Principal

Sentry is an application monitoring platform trusted by 200,000+ organizations. The company helps developers fix errors and performance issues before users notice, and is building its AI-native future.

Sentry is looking for a Staff Software Engineer to join the AI/ML team as one of its foundational members. The role focuses on evolving Seer, Sentry's AI debugger, which uses error, trace, replay, and commit data to diagnose and fix software issues. The engineer will help decide how the system should evolve as models improve, building state-of-the-art agentic AI systems to triage, debug, and solve production issues.

• Build state-of-the-art agentic AI systems to triage, debug, and solve real production issues.
• Set technical direction for how agents get context, use tools, and decide when they're done.
• Build evals to determine whether a new model or prompt actually helped, fast enough for regular use.
• Decide when to use a frontier model, a smaller one, or a trained model, revisiting as cost and capability shift.
• Leverage Sentry's dataset of errors, spans, and profiles.
• Own major AI initiatives end to end, alongside developers and product teams.
• Run what you ship in production and debug it with Sentry.

• Shipped an LLM-backed system people depended on, and can explain what broke.
• Strong opinions on agent design, with at least one change in the last year.
• Trained or fine-tuned models when appropriate, and know when not to.
• Write solid production Python.
• Owned a system or component and led work across multiple engineers and teams, with a design doc that was read.
• Write clear technical documentation, mentor other engineers, and present to technical audiences.

Base salary range: $240,000 to $400,000. Eligible for incentive compensation, equity grants, paid time off, and group health insurance coverage. See Sentry Benefits for details.

Sentry is committed to equal employment opportunities and provides reasonable accommodations for disabilities. Contact accommodations@sentry.io for assistance.