Tailscale

6 open remote positions

Tailscale builds software that securely interconnects people and devices, creating an easy, sensible, and safe internet experience. Founded in 2019 and fully distributed, the company is backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Salary Distribution 6 of 6 jobs

PTO Distribution 4 of 6 jobs

Unlimited PTO 4 jobs (67%)

Parental Leave Distribution

Maternity Leave 6 jobs

20w
20w
20w

Paternity Leave 6 jobs

16w
16w
16w

Benefits Overview 6 of 6 jobs

Dental (6) PTO (6) Vision (6) Medical (5) Retirement (5) Equity (3) Parental Leave (3) Professional Development (3) Home Office (2) Health (1) Internet Reimbursement (1) Retirement matching (1)

Open Positions

Software Engineer, AI Enablement

$160,000–$221,000/yr
Canada Unlimited PTO 20w maternity 16w paternity

  • Partner with engineering leadership and co-founders to define AI-enablement priorities and build internal tools for AI-assisted development.
  • Build, maintain, and iterate on tools and practices that help engineers use coding agents like Claude Code, Codex, and OpenCode more effectively.
  • Act as an internal advocate for effective AI practices through documentation, talks, and hands-on coaching to drive adoption across teams.

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Customer Support Engineer

$97,320–$121,399/yr
UK Unlimited PTO 20w maternity 16w paternity

  • Serve as the primary escalation point for technically complex tickets from paying customers, taking full ownership through resolution.
  • Diagnose and troubleshoot advanced Tailscale-specific issues like ACL misconfigurations, subnet routing, and identity provider integrations.
  • Manage a ticket queue with consistent focus on SLA adherence and drive high CSAT scores.

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Senior Customer Support Engineer (Tier 3), Customer Escalations

$112,493–$140,861/yr
Canada Unlimited PTO 20w maternity 16w paternity

  • Own high-severity technical escalations from intake through resolution or engineering handoff.
  • Partner with Support and Product/Engineering to close the gap between customer problems and engineering fixes.
  • Monitor patterns across escalations to catch systemic issues and translate into product improvements.

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Principal Product Manager (Dataplane)

$197,000–$246,000/yr
United States Unlimited PTO 20w maternity 16w paternity

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

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Windows Engineer

$139,883–$175,098/yr
Canada 20w maternity 16w paternity

  • Work with engineers on a native Windows desktop client using Windows App SDK, WinUI, C#, XAML and Go.
  • Implement support for the latest Windows platform features while maintaining compatibility with older versions.
  • Develop and optimize product features on Windows with a focus on UI components and platform integration.

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