Staff Product Designer

7 hours, 54 minutes ago
Full-time
Lead
Design and User Experience
Tailscale

Tailscale

Tailscale is a zero config VPN service that simplifies network security and connectivity for teams of any scale, offering easy deployment, minimal latency, and compatibility with existing services.

Diversified Telecommunication Services
51-250
Founded 2019
$115M raised

Description

  • Define where design attention is needed across the network features space and lead discovery on ambiguous, multi-surface problems.
  • Translate abstract technical systems into clear problem frames using diagramming, system mapping, and other artifacts that align engineering, product, and stakeholders.
  • Design and deliver end-to-end solutions for GUI and CLI experiences, including implementation support and QA.
  • Explore forward-looking design questions in areas without clear owners or established answers.
  • Partner closely with engineering and product management to move from ambiguous problem statements to well-reasoned solutions.
  • Raise the bar for craft and quality across the team and contribute to broader design process and product thinking.
  • Translate user research, behavioral data, and product knowledge into design direction.
  • Use AI tools in practical ways for research synthesis, rapid prototyping, and solution exploration.
  • Develop a point of view on where AI-assisted experiences fit in technically complex products.

Requirements

  • 10+ years of product design experience, with meaningful time operating at the staff level or equivalent scope.
  • A strong portfolio showing work on technically sophisticated B2B or infrastructure products.
  • Experience leading discovery on problems without waiting for scope to be defined.
  • A developed point of view on users and product direction that has influenced roadmap and strategy.
  • Genuine interest in networking and security, with comfort engaging deeply in technical subject matter.
  • Strong written communication and the ability to explain design decisions to technical and non-technical partners.
  • Comfort working asynchronously in a distributed environment with highly technical teammates.
  • Hands-on experience with Tailscale or familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing (nice to have).
  • Hands-on experience with cloud-native deployment infrastructure such as AWS, GCP, or DigitalOcean (nice to have).
  • Experience designing for developer or IT administrator audiences, data-informed design practice, or fluency with AI tools (nice to have).

Benefits

  • Competitive total compensation package with base salary, equity incentive plan, and variable commission for quota-based roles.
  • CAN pay range of $226,460 to $282,740 CAD.
  • Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family.
  • Remote-first work environment with flexibility in how and when you work.
  • Support for in-person connection through company retreats, team off-sites, and coworking access.
  • $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off and healthy work-life integration.
  • Home office support, including a company-owned laptop, monthly internet reimbursement, and $1,000 USD for workstation setup.
  • Generous parental leave with top-ups for up to 26 weeks, available from the first day.

Interested in this position?

Apply directly on the company website

Apply Now

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