Staff Software Engineer, AI Developer Tooling

Sentry•San Francisco, CA

4d•$220,000 - $400,000

About The Position

Sentry is seeking a Staff Software Engineer to focus on AI Developer Tooling. This role is unique as it sits within Platform Engineering and owns the AI-assisted coding domain, working across all of engineering at Sentry. The primary focus will be on how AI coding agents participate in the software development lifecycle. The engineer will audit and prioritize systems that AI coding agents depend on, expose these systems via API, and build connections for tools like Claude Code to operate on them end-to-end. The scope will expand to improving AI-generated pull requests and automating engineering tasks. The role involves context engineering to determine what to send to the model and harness engineering to manage tools, permissions, state, tests, logs, retries, checkpoints, guardrails, and evaluations. The engineer will work closely with the dev infrastructure team and collaborate across all product teams. This role offers broad impact, directly changing how Sentry engineers ship software. It requires a high degree of agency, comfort with ambiguity, and the ability to structure one's own work. The ideal candidate will have a strong ability to pattern-match across systems and codebases, moving fluidly between infrastructure, backend, and developer tooling. A metric-driven approach, combined with direct engineer feedback, is valued. The role thrives on variety, shifting between strategic and hands-on work, and requires clear communication and the ability to influence without authority.

Requirements

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.

Nice To Haves

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

Responsibilities

Audit Sentry’s internal developer systems and make them API-ready for AI agents, prioritizing and driving the work of exposing these systems programmatically, and building the connections that allow agents to operate on them end-to-end.
Build the harness tooling, context systems, and feedback loops that 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: security dependency upgrades, minor bug fixes, and routine maintenance, so engineers can focus on higher-value work.
Design and build internal tools that make engineering more effective: productivity dashboards, AI-assisted issue triage, CI/CD optimizations, and tooling that reduces toil.
Identify and remove organizational friction. Use data and direct observation to find where engineering is slowing down, recommend solutions to senior leadership, and build cross-team buy-in for changes.