Senior Product Designer

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.

We are looking for a Senior Product Designer to join the design team  will work closely with product managers and engineers across our cross-functional teams, focused on the experience of IT administrators, Dev Ops 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.

• 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.

• 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.
• 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.

$146,000 - $183,000 USD

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company
  —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Connect with other Tail scalars IRL. Attend our annual company retreat, participate in team off-sites, and…