[Remote] Senior Product Designer

Note: The job is a remote job and is open to candidates in USA. Tailscale is a company focused on building a secure and interconnected Internet for users and organizations. They are seeking a Senior Product Designer to work closely with product managers and engineers to enhance the user experience for IT administrators and DevOps engineers.

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

Skills

• 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

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• 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).
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

Company Overview