Staff Software Engineer, AI Developer Tooling

Sentry•San Francisco, CA

1d•$240,000 - $320,000

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, owning the AI-assisted coding domain and collaborating across all of engineering. The primary focus will be on integrating AI coding agents into Sentry's software development lifecycle. This involves making internal systems accessible via API for agents, auditing and prioritizing gaps, exposing systems programmatically, and building connections for tools like Claude Code to operate end-to-end. The role also expands to improving AI-generated pull requests and automating routine engineering tasks. You will work on context engineering, harness engineering, tool accessibility, permissions, state management, testing, logging, retries, checkpoints, guardrails, and evaluations. You will collaborate closely with the dev infrastructure team and across all product teams. The work you do will directly impact how Sentry engineers ship software. Responsibilities include auditing and API-enabling internal developer systems, building harness tooling, context systems, and feedback loops for high-quality pull requests, automating high-volume, low-priority engineering work (like dependency upgrades and bug fixes), designing and building internal tools for engineering effectiveness (dashboards, AI-assisted triage, CI/CD optimizations), and identifying and removing organizational friction by recommending solutions to senior leadership and building cross-team buy-in.

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.
Prioritize and drive the work of exposing those systems programmatically, and build 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.