Senior Product Designer | Sentry

About Sentry

Sentry builds error and performance monitoring tools that developers actually want to use. The product is open source, installed by 160,000+ organizations — from solo developers to companies like Disney, Microsoft, and Atlassian. If you've ever started a new project and added error monitoring, chances are it was Sentry.

The company dominates the errors market. That part is done. What's happening now is more interesting: the team is expanding into distributed tracing, metrics, logs, session replays, and most actively, AI-powered developer workflows. Autofix already finds root causes and generates fixes. The next step is agentic issue resolution: bugs that find themselves, get triaged, and raise their own PRs. The interfaces for this don't exist yet. You'd be designing them.

Sentry raised $217M+ and is roughly at breakeven with most of the capital still unspent. Growth is 33%+ year over year. The culture is deeply technical: engineers are product-minded, opinionated, and collaborative. There's no large PM org by design. The CPO (ex-Apple) believes that for developer tools, designers and engineers should lead the product together.

The design team is in the middle of a rebuild. Aiden, the new Head of Product Design, is shifting the practice from pixel-focused execution toward strategic product thinking by starting with "why," talking to customers, and forming opinions. If you want to join a team at the beginning of that shift, this is the moment.

What You'll Be Responsible For

• Design tools that make complex developer workflows (error triage, distributed tracing, AI-assisted debugging) feel clear and effortless.

• Start with the problem, not the screen. Talk to users, understand the real pain, and form a point of view on your product space before you open Figma.

• Work daily with engineers, product managers, and designers (in design sprints, whiteboard sessions, and critiques). You'll sit with your engineering team, not in a design silo.

• Contribute to Sentry's design language by raising consistency, accessibility, and the quality bar across the platform.

• Present your work in critique twice a week. Give feedback, receive it, make each other better.

• Advocate for design decisions at every level from pixel-level detail to product strategy.

What You'll Need to Succeed

• 5+ years designing complex software products, with a portfolio that shows how you think, not just what you shipped. The team will look for the story: what was the problem, what did you explore, and why did you land where you did.

• Strong visual and interaction design skills (structure, hierarchy, clarity).

• Experience turning genuinely complex workflows into something that feels simple.

• Real experience talking to users. Not "I reviewed research someone else did", but actually sitting down with people, running interviews, turning what you heard into design decisions.

• Comfort with ambiguity while the team is rebuilding its design practice.

• A strong feedback metabolism. You need to give honest feedback and receive it without taking it personally.

Huge Plus If You Have

• Experience with developer tools, observability platforms, or technical infrastructure products.

• Built or significantly contributed to a design system.

• Open-source contributions or code in your portfolio (HTML/CSS, React, prototypes).

• Experience prototyping in code using tools like Cursor or Claude Code.

• Used Sentry yourself, even better if you have opinions about it.

What You'll Get

• $170,000–$220,000 base salary + incentive compensation + equity.

• Medical, dental, and vision in 100% covered for you, 75% for dependents. Zero deductible option available.

• Flexible PTO, 15 holidays, 4-week sabbatical at your 4-year mark, and 7–14 weeks paid family leave.

• 401(k) through Fidelity, plus HSA with company contributions.

• $1,000/year for learning and development, $600/year wellness benefit, $75/month tech stipend.

• A San Francisco office with excellent catering, snacks, and Thursday happy hours at 4 PM — beer, ice cream, and an unspoken agreement that the workday is done.

• Hybrid schedule: Mondays, Tuesdays, and Thursdays in the office. The rest is yours.

• Weekly 1:1 with the Head of Product Design. Direct line to leadership, no layers in between.

• A team that takes the work seriously, not themselves.

What's Great About This Role

Sentry's design practice is being rebuilt from the ground up. The previous culture was pixel-focused and operated more like a loose affiliation of independent contributors. Designers now start with strategy, talk to customers, and own the "why" behind what they build. This shift has been met with hunger, not resistance. Engineers and leadership are arm-in-arm with design.

You'd join at the inflection point. Your work won't disappear into a system of approvals. It'll ship, and it'll be visible. Meanwhile, the product problem is genuinely hard: how do you make error monitoring, distributed tracing, and AI-assisted debugging feel intuitive to millions of developers? Sentry already has the distribution, such as the SDK, which is the second thing most developers install after GitHub. Now the question is what the next generation of these tools looks like, and that answer increasingly involves AI.

If you want to design developer tools at a company that's both stable and ambitious, with a team figuring out how design earns its seat at the table, this is one of the best opportunities to do it.