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About the role

  • Senior Product Designer collaborating with product managers and engineers to enhance user experience at Tailscale. Focusing on IT administrators, DevOps engineers, and security professionals.

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.

Requirements

  • 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

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package.
  • Comprehensive group benefits with no waiting period.
  • Remote first company—most of our teams work fully remotely.
  • Connect with other Tailscalars IRL.
  • Support for your personal and professional development.
  • Paid time off and a healthy work-life integration.
  • A build-your-own home office setup.
  • Generous parental leave program from your first day.

Job type

Full Time

Experience level

Senior

Salary

CA$195,640 - CA$245,220 per year

Degree requirement

Bachelor's Degree

Location requirements

RemoteCanada

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