Tailscale

18 open remote positions

Tailscale is making safe connection effortless by delivering software that securely interconnects people and devices. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Salary Distribution 17 of 18 jobs

PTO Distribution 4 of 18 jobs

Unlimited PTO 4 jobs (22%)

Parental Leave Distribution

Maternity Leave 15 jobs

20w
20w
20w

Paternity Leave 15 jobs

16w
16w
16w

Benefits Overview 16 of 18 jobs

Dental (16) Vision (16) Professional Development (12) Equity (11) Medical (11) PTO (11) Parental Leave (10) Retirement (9) Health (5) 401(k) (4) Home Office (4) Home Office Stipend (2) Retirement Matching (2) Flexible PTO (1) Remote Work (1) Retirement Match (1) Retirement Plan (1)

Open Positions

$195,345–$243,934/yr
Canada 20w maternity 16w paternity

  • Set the vision and roadmap for the Tailscale dataplane, including WireGuard behavior, DERP relay expansion, subnet routers, exit nodes, and client-side networking.
  • Define performance and reliability as customer-facing product requirements and own connectivity product strategy end to end.
  • Partner closely with GTM, Customer Success, and Solutions Engineering on production traffic commitments and strategic enterprise deals.

$158,000–$197,000/yr
United States 20w maternity 16w paternity

  • Lead and develop a high-performing team of Talent Acquisition Partners while partnering with business leaders to deliver exceptional hiring outcomes.
  • Drive recruiting strategy and performance by translating business priorities into actionable plans and using data to assess risks and improve outcomes.
  • Build trusted relationships with senior leaders and serve as a strategic advisor on hiring priorities, talent markets, and workforce needs.

$200,000–$225,000/yr
United States Unlimited PTO

  • Own and scale Tailscale's Developer Relations function as a strategic growth program, including strategy, roadmap, and team leadership.
  • Build and lead a high-performing DevRel organization, hiring and developing senior and junior technical talent.
  • Develop and manage repeatable DevRel programs across content, video, events, workshops, community, and integrations, partnering with Product, Engineering, and Marketing.

$146,000–$183,000/yr
US 20w maternity 16w paternity

  • Conduct usability and quality-validation testing, owning the full study lifecycle from recruiting to analysis and recommendations.
  • Coach designers and PMs on study design, and build reusable enablement assets like templates and guides.
  • Maintain research infrastructure including the library and tool stack, and manage participant panel and logistics.

$95,000–$119,000/yr
US 20w maternity 16w paternity

  • Create high-impact content that turns search insights, customer questions, and community trends into growth.
  • Partner with the AI & Organic Search Manager to craft content optimized for both search engines and AI platforms.
  • Build hands-on experience with Tailscale to produce technically accurate, high-velocity content that drives adoption.

$148,000–$246,000/yr
Canada Unlimited PTO 20w maternity 16w paternity

  • Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale.
  • Offer technical support and conduct QBRs to review usage, success metrics, and future goals, identifying opportunities for deeper engagement.
  • Build strong relationships with customers, acting as a trusted advisor, and serve as the voice of the customer internally to relay feedback.

$250,000–$250,000/yr
US 20w maternity 16w paternity

  • Lead technical discovery, solution architecture, demos, and proofs-of-concept for partner-sourced and co-sell deals.
  • Develop and deliver partner technical enablement including training, certification content, and reference architectures.
  • Collaborate with Channel Account Managers and AEs to identify, qualify, and close new and expansion opportunities through the channel.

$104,000–$156,000/yr
US 20w maternity 16w paternity

  • Partner closely with the VP of Engineering to maximize their effectiveness by managing calendars, priorities, and cross-functional coordination.
  • Own complex calendar management across time zones, coordinate meetings, offsites, and ensure clear purpose and outcomes.
  • Drive cross-functional collaboration with leaders across Engineering, Product, Design, and more to improve operational efficiency.