Staff Software Engineer, AI Developer Tooling

at Sentry

📍 San Francisco, United States

USD 240,000-300,000 per year

SENIOR

✅ Hybrid

Used Tools & Technologies

Machine Learning

Required Skills & Competences
Tag name is followed by "@" symbol and proficiency level value. About proficiency levels:

1-2 — basic awareness. Minimal hands-on experience, and a rudimentary understanding of the technology's purpose;

3-6 — daily use. Comfortable and regular usage, capable of handling common tasks and challenges related to the technology;

7-9 — you are an expert, you can teach others, you know all the pitfalls and tricks;

10 — exceptional knowledge, comprehensive understanding, and adeptness in all aspects of the technology, including advanced problem-solving. Think twice before claiming or demanding such level.

Security @ 4 Software Development @ 4 CI/CD @ 4 Distributed Systems @ 3 Leadership @ 4 Communication @ 4 API @ 4 Technical Leadership @ 6 Sentry @ 4 Audit @ 4 Claude Code @ 4 AI @ 4

Details

About Sentry

Bad software is everywhere, and Sentry is on a mission to help developers write better software faster so we can get back to enjoying technology.

With more than $217 million in funding and 100,000+ organizations, Sentry builds performance and error monitoring tools used by companies like Disney, Microsoft, and Atlassian. Sentry embraces a hybrid work model across its global hubs, with Mondays, Tuesdays, and Thursdays set as in-office anchor days to encourage meaningful collaboration.

About the Role

This role sits within Platform Engineering owning the AI-assisted coding domain and works across all of engineering at Sentry. The focus is on how AI coding agents participate in the software development lifecycle. Many internal systems are not currently agent-ready; you will audit and prioritize those gaps, expose systems programmatically (via APIs), and build connections that let tools like Claude Code operate end-to-end. The scope expands to improving AI-generated pull request quality and automating engineering work that is important but consistently deprioritized.

You will consider both context engineering (what to send to models) and harness engineering (tools agents can use, permissions, state carried forward, tests required, logs captured, retries, checkpoints, guardrails, and evaluations).

You will work closely with the dev infrastructure team as your home base and collaborate across product teams once the tooling foundation is in place. The work will directly change how Sentry engineers ship software.

Responsibilities

Audit Sentry's internal developer systems and make them API-ready for AI agents; prioritize and drive work to expose those systems programmatically.
Build harness tooling, context systems, and feedback loops to help agents generate high-quality, repository-aware pull requests, including automated pre-review checks and PR quality measurement tailored to Sentry's codebase.
Automate high-volume, low-priority engineering work such as security dependency upgrades, minor bug fixes, and routine maintenance.
Design and build internal tools to improve engineering effectiveness: productivity dashboards, AI-assisted issue triage, CI/CD optimizations, and tooling that reduces toil.
Identify and remove organizational friction using data and direct observation; recommend solutions to senior leadership and build cross-team buy-in.

You'll Love This Job If You…

You are passionate about AI coding tools and curious about how to make them better; you follow the space closely and want to be at the frontier of how AI participates in real-world software development.
You are high agency: comfortable with ambiguity, able to structure your own work, and know when to build, delegate, or stop.
You can pattern-match across systems and codebases and move between infrastructure, backend, and developer tooling without friction.
You are metric-driven but understand the value of talking directly to engineers experiencing the pain.
You enjoy variety and can shift between strategic and hands-on work.
You communicate clearly and can influence without authority, presenting recommendations to senior technical leadership and building buy-in.

Qualifications

10+ years of software engineering experience.
Experience building tools or workflows that improve how developers or AI agents work (CI/CD, dev infra, AI harness tooling, AI-first coding workflows, or public contributions in this space).
Strong software and system design fundamentals.
Genuine curiosity and hands-on experience with AI coding tools and agents (prior ML experience not required).
Excellent written and verbal communication; comfortable presenting to senior technical leadership.
Track record of driving cross-team technical initiatives to completion.
Nice to have: experience with large-scale distributed systems or monolith decomposition; prior work on developer experience or engineering productivity programs; familiarity with code review tooling, static analysis, or automated PR pipelines.

Compensation

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 will be determined by factors including work location, education, experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry's employee benefit plans/programs (including incentive compensation, equity grants, paid time off, and group health insurance coverage).

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities and reasonable accommodations to employees and candidates with disabilities. If you need assistance or an accommodation due to a disability, contact [email protected]. For details about applicant data handling, see Sentry's Applicant Privacy Policy: https://sentry.io/careers/applicantprivacy/