Job Description
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 Staff Product Designer to join the design team at Tailscale. You will primarily partner with the Network Features team, which owns one of the most technically complex and strategically important surfaces in the product: how traffic finds its destination, how networks are segmented and connected, and how operators control that behavior at scale. That spans a wide range. On the user-facing side, Admin users orchestrate their networks by configuring settings related to: subnet routing, exit nodes, App Connectors, Services, and DNS. On the infrastructure side, you’ll interface with topics like: traffic steering, high availability, DERP servers, and cloud networking primitives. These are not features with obvious consumer analogues. The users are network engineers, IT administrators, and developers building on top of Tailscale, and the problems they bring are genuinely hard to make simple. At the staff level, scope is not handed to you. You will define where design attention is needed across this space, lead discovery on problems that don't yet have clear answers, and shape product direction alongside your engineering and PM partners. A significant part of that work is translation: taking abstract technical systems and surfacing the design problems hidden inside them clearly enough that engineers, PMs, and stakeholders can align on what to solve and why. Diagramming, system mapping, and other artifacts that make complexity legible are tools you reach for naturally, not as documentation but as a way of driving shared understanding and unblocking decisions. Your influence will extend beyond your immediate projects, affecting how the broader design team approaches craft, process, and product thinking. You will report to the product design manager and work closely with a team of five product designers and one design researcher. Most of your time will be spent embedded with the Network Features team, with some involvement in wider design team or product initiatives. People who do well here are genuinely curious about networking and security, comfortable going deep on technically complex domains, and fluent working asynchronously with highly technical teammates. Key Responsibilities Define where design attention is needed across the network features product space and lead discovery on complex, ambiguous problems that often span multiple features or product areas. Translate abstract technical systems into clear problem frames, using diagramming, system mapping, and design artifacts to build shared understanding and drive alignment across engineering, product, and other stakeholders, Deliver design solutions end-to-end as needed, whether that means changes to a GUI, a CLI experience, or both, working closely with engineers through implementation and QA. Explore forward-looking design questions in spaces that do not yet have clear owners or established answers. Partner closely with engineering and PM counterparts to move from ambiguous problem statements to clear, well-reasoned solutions. Raise the bar for craft and quality across your team and contribute to how the broader design organization approaches process and product thinking. Translate insights from user research, behavioral data, and your own product knowledge into design direction. Bring AI tools into your workflow in practical ways, whether for research synthesis, rapid prototyping, or solution exploration, and develop a point of view on where AI-assisted experiences belong in technically complex products. What We Are Looking For 10+ years of product design experience, with meaningful time operating at the staff level or equivalent scope Strong portfolio demonstrating experience with technically sophisticated B2B or infrastructure products, and a track record of leading discovery on problems without waiting for scope to be defined A developed point of view on users and product direction, with evidence of using that perspective to influence roadmap and strategy across engineering and product teams Genuine interest in the networking and security space and comfort engaging with technically complex subject matter Strong written communication and an ability to articulate design decisions clearly to both technical and non-technical partners Ease working in a distributed, asynchronous environment with highly technical teammates Nice to Have Hands-on experience with Tailscale, or working familiarity with netwo
