Senior Product Designer

1 week, 5 days ago
Full-time
Senior
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

  • Own discovery and design for ambiguous problems from early framing through delivery and QA.
  • Work closely with product managers and engineers to turn unclear problems into well-reasoned, shippable solutions.
  • Design across both GUI and CLI surfaces and stay engaged through implementation, not just handoff.
  • Seek, incorporate, and respond to feedback from peers, the team, and managers throughout the design process.
  • Take initiative in collaboration and push for clarity even on projects you are not directly leading.
  • Develop a strong understanding of product areas and the broader implications of design decisions.
  • Use AI tools to synthesize research, explore directions faster, and pressure-test ideas.

Requirements

  • 5+ years of product design experience with a portfolio showing end-to-end ownership of complex work.
  • Experience with technically sophisticated B2B or infrastructure products.
  • Ability to lead discovery in a complex domain without waiting for a brief.
  • A strong point of view on users and product quality, with the confidence to act on it.
  • Comfort working closely with engineers and product managers who care deeply about implementation details.
  • Clear, direct writing skills for communicating design decisions to both engineers and stakeholders.
  • Strong self-management skills with the ability to shift priorities across multiple projects.
  • Experience working in distributed, async environments.
  • Hands-on experience with Tailscale or familiarity with networking concepts such as DNS, VPNs, proxies, or traffic routing (preferred).
  • Experience designing for developer or IT administrator audiences (preferred).
  • Data-informed design practice, including behavioral analytics or experimentation (preferred).
  • Fluency with AI tools in a design workflow and curiosity about AI-assisted experiences in technical products (preferred).

Benefits

  • Competitive total compensation package with base salary, equity, and variable commission for quota-based roles.
  • Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family.
  • Remote-first work environment with flexibility in where and when you work.
  • $1,500 USD annually for professional development, plus mentorship, coaching, and internal promotion opportunities.
  • Flexible paid time off program to support work-life integration.
  • Home office support including a company-owned laptop, monthly home internet reimbursement, and $1,000 USD for workstation setup.
  • Generous parental leave with top-ups for up to 26 weeks from your first day.
  • Annual company retreat, team off-sites, and opportunities for in-person collaboration and social events.

Interested in this position?

Apply directly on the company website

Apply Now

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