Senior Product Designer

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Senior Product Designer to join their design team, focusing on enhancing the user experience for IT administrators, DevOps engineers, and security professionals who utilize Tailscale's products.

Responsibilities:

• Own discovery and design on problems that don't always come with a clear brief, from early framing through delivery and QA
• Work closely with engineers and PMs to move from a fuzzy problem to something well-reasoned and shippable
• Deliver across surfaces, GUI and CLI alike, and stay engaged through implementation, not just handoff
• Treat feedback as part of the work, not a checkpoint. Seek it out from peers, your team, and your manager, and use it to make the work better
• Take initiative in how you collaborate and push for clarity, even on projects you're not leading
• Understand the product areas you touch well enough to know when a decision has implications beyond the immediate problem
• Use AI tools where they actually help, synthesizing research, exploring directions faster, pressure-testing ideas

Requirements:

• 5+ years of product design experience, with a portfolio that shows you've owned complex work end-to-end, not just executed on it
• Experience with technically sophisticated B2B or infrastructure products. You're comfortable going deep on a domain and know how to lead discovery without waiting for a problem to be handed to you
• A real point of view on users and product quality, and the confidence to act on it
• At ease working alongside engineers and PMs who care a lot about how things actually work
• A clear, direct writer. You can explain a design decision to an engineer and a stakeholder without producing two different documents
• You run your own workload well, can shift between projects as priorities change, and don't need someone else to tell you what matters
• Experienced working distributed and async, and good at it
• Hands-on experience with Tailscale, or working familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing
• Experience designing for developer or IT administrator audiences
• Data-informed design practice including behavioral analytics or experimentation
• Fluency with AI tools as part of your design workflow and curiosity about where AI-assisted experiences fit in technical products