Senior Product Designer | Sentry

hirehire • San Francisco, CA

12d • $170,000 - $220,000 • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• $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 This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed