Senior Product Designer

Role overview

Join Tailscale as a Senior Product Designer working with product managers and engineers to improve the experience of IT administrators, DevOps engineers, and security professionals. You’ll help users set up, monitor, and troubleshoot tailnets with a focus on clarity and reliability, shipping end-to-end in a small, fast-growing design team.

Key responsibilities

• Own discovery and design for problems without a clear brief: from early framing through delivery and QA.
• Partner with engineers and PMs to turn ambiguous problems into well-reasoned, shippable solutions.
• Deliver across multiple surfaces, including GUI and CLI, and stay involved through implementation (not just handoff).

Requirements

• Strong comfort with technical subject matter and curiosity about systems “under the hood”.
• Clear, direct communicator able to explain decisions consistently to engineers and stakeholders.
• Ability to manage priorities independently and shift across projects as needed.
• Ability to collaborate effectively with engineers/PMs focused on how things work.
• Demonstrated user and product-quality judgment, with confidence to act on it.
• Technically sophisticated B2B/infrastructure product experience; able to go deep in the domain and lead discovery.
• 5+ years of product design experience with a portfolio showing end-to-end ownership.
• Experience working distributed and async.
• Hands-on experience with Tailscale or familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing.
• Data-informed design (behavioral analytics and/or experimentation).
• Experience designing for developer or IT administrator audiences.
• Curiosity and fluency with AI tools in the design workflow for technical products.

Nice to have

• Fluency with AI-assisted design workflows specifically tailored to technical products.