Staff Software Engineer, AI Developer Tooling

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.

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.

Qualifications

• 10+ years of software engineering experience.
• 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.
• Strong software and system design fundamentals.
• Genuine curiosity and hands-on experience with AI coding tools and agents. Prior machine learning experience isn’t required.
• Excellent written and verbal communication; comfortable presenting to senior technical leadership.
• A track record of driving cross-team technical initiatives to completion.
• Experience with large-scale distributed systems or monolith decomposition (nice to have).
• 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).

Pay

The base salary range that Sentry reasonably expects to pay for this position is $240,000 to $300,000. A successful candidate’s actual base salary amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge.

Benefits

A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage).

Equal Opportunity

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry.