Tailscale
Head of Legal
Remote (Canada) +2 · Remote · Director · Full-time · Posted Sep 18, 2026
- Location
- Remote (Canada)
Canada
United States - Experience
- Significant legal experience; no specific number of years stated.
- Education
- Law degree.
About the job
Build and lead Tailscale’s legal function, advising executives and teams on legal risk and business decisions as the company grows globally.
What you'll do
- Set the legal function’s strategy, operating model, priorities, and team; build scalable processes and capabilities.
- Advise executives and cross-functional teams on legal issues, risks, and practical business decisions.
- Lead commercial legal capability and manage internal legal talent and outside counsel across jurisdictions.
What they ask for
- Significant legal experience, including meaningful in-house experience at a technology company and a record of helping legal functions scale.
- Law degree and active membership in an applicable bar or equivalent authorization to practice law.
- Experience advising executives on complex or consequential decisions and partnering with technical, operational, and commercial teams.
- Track record of building or improving legal capabilities, teams, programs, processes, or areas of practice.
Nice to have
- Experience in technically complex software environments, such as developer tools, infrastructure, cloud, networking, or cybersecurity.
- Relevant experience with open-source software, privacy, data, AI-enabled products, or international operations.
Pay
$298,820 — $427,460 CAD (base salary)
AI focus
Advise on legal considerations involving AI and potentially AI-enabled products or AI use in company operations; hiring uses AI-assisted screening and assessment tools, with hiring decisions made by people.
Model-written summary · the original posting is authoritative