Staff Software Engineer, Sentry
AI Developer Tooling
$240-320k
+ Equity + Bonus
Application performance monitoring & error tracking software
Job no longer available
Application performance monitoring & error tracking software
201-500 employees
Job no longer available
$240-320k
+ Equity + Bonus
201-500 employees
Company mission
To empower developer teams to build their best possible software, more quickly and easily.
Role
Who you are
- You’re passionate about AI coding tools and curious about how to make them better. You follow the space closely, have opinions about what works, and want to be at the frontier of how AI participates in real-world software development
- You’re high agency. You don’t wait for permission. When you see a problem, you figure out the right solution and make it happen. You’re comfortable with ambiguity, can structure your own work, and know when to build it yourself, when to delegate, and when to say “this isn’t worth doing.”
- You’ve seen enough systems and codebases to pattern-match quickly. You can move between infrastructure, backend, and developer tooling without friction, and you bring seasoned judgment to technical decisions
- You’re metric-driven but not metric-obsessed. You use data to make good decisions, and you know the best insights sometimes come from talking directly to the engineers feeling the pain
- You thrive on variety. You enjoy the pace of “figure this out and build it, then move to something completely different,” and you can shift between strategic and hands-on work without losing momentum
- You communicate clearly and can influence without authority. You work across team boundaries, present recommendations to senior leadership, and build buy-in for your ideas. People listen because you’ve done the work to understand things deeply
- 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)
What the job involves
- 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
- For AI coding agents to work well in our repo, the internal systems they depend on need to be accessible via API, not locked behind UIs that require human interaction. 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
- Audit Sentry’s internal developer systems and make them API-ready for AI agents. You’ll 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
Our take
Defective software leads to dissatisfied users, disruptions and potential financial losses for companies. Sentry has created application monitoring and error tracking software to help developers fix errors faster, easier and more cost effectively.
More than 1 million developers and 70,000 organizations worldwide, including the likes of Microsoft, Disney, Atlassian, Cloudflare and Slack, have used Sentry to monitor their code health. And the company is well-positioned for significant growth as there is an emerging need for solutions that address holistic application health. As more companies focus on digital to engage with their customers, the reliability of their applications is essential.
The global bug-tracking software market is expected to reach over $600 million by the end of 2026 with an annual growth rate of almost 10%. Further, the company opened another office in Denver in early 2023, expanding its regional presence, as it continues to broaden its market presence.
Freddie
Company Specialist at Welcome to the Jungle
Insights
28% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
May 2022
$90m
SERIES E
Feb 2021
$60m
SERIES D
Total funding: $216.5m
Company benefits
- Competitive Compensation + Equity
- Medical, Dental, Vision Insurance
- Commuter Stipend
- Professional Development Stipend
- Health & Wellness Benefits
- Charitable Matching Program
- Flexible PTO
- Paid Parental Leave
- 401k Plan
Company HQ
Financial District, San Francisco, CA
Leadership
David Cramer
(Co-Founder & CPO)They started their career as a Software Engineer at Curse, before roles at Enthropia, Disqus, and Dropbox. Having co-founded Sentry in January 2012, they left Dropbox in 2015.
Chris Jennings
(Co-Founder & Chief Creative Officer)They have been a Frontend Developer at AgencyTen, Director of Design and UX at Disqus and most recently a Product Designer at GitHub.
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