Senior Product Designer

About Tailscale Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. Job Description We are looking for a Senior Product Designer to join the design team at Tailscale. You will work closely with product managers and engineers across our cross-functional teams, focused on the experience of IT administrators, DevOps engineers, and security professionals who use Tailscale to build and manage their organization's network. Your work will center on helping these users set up, monitor, and troubleshoot their tailnets. Your job is to make that process feel as clear and reliable as the product underneath it. The work varies in scale and shape. Some projects are well-defined with a clear user problem to solve. Others are improvements to existing features, small cleanup tweaks, or interaction problems that have been on the backlog for a while. You're comfortable moving between those contexts, bringing the same care and curiosity to a focused UI fix as you would to a larger, more open-ended challenge. Tailscale's design team is small and the company is growing fast. That means the work doesn't always arrive in neat packages. You might be deep in a multi-month project one week and pulled in to help unblock something urgent the next. People who thrive here are comfortable with technical subject matter, curious about how things work under the hood, and don't need a lot of scaffolding to figure out what to do next. Key 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. What We Are Looking For 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 Nice to Have 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 As a company,