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, where the role involves collaborating with product managers and engineers to enhance the user experience for IT administrators, DevOps engineers, and security professionals using Tailscale.

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