299K–427K CAD / year
Head of Legal
LegalRemote — unknown
Published on 2026-09-18
These details were extracted automatically from the original listing. They may not be complete or fully up to date — it's worth checking the original job post.
About this role
Tailscale seeks a Head of Legal to lead their legal function as the company grows. The role involves advising executives on various legal matters, managing risk, and building legal processes and teams. A focus will be on enhancing commercial legal capabilities and navigating complex regulatory landscapes.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
What you'll do
- Build and evolve Tailscale's legal strategy and team
- Serve as a trusted advisor to executives
- Help identify material risks and recommend safeguards
- Advise on corporate governance, product development, and compliance
- Build scalable legal processes and decision-making frameworks
- Manage outside counsel and legal capabilities
- Support strategic partnerships and corporate initiatives
- Anticipate emerging legal developments
What we're looking for
- Significant in-house legal experience in technology
- Active membership in a recognized bar association
- Demonstrated growth in legal scope and responsibility
- Ability to navigate complex legal issues
- Experience advising on consequential business decisions
- Strong communication and judgment skills
- Familiarity with legal considerations in tech environments
- Ability to operate in ambiguity
Nice to have
- Experience in developer tools or cybersecurity
- Understanding of open-source software and technology partnerships
- Knowledge of AI-enabled products
- Experience with data residency and localization
- Legal experience across multiple countries
- Corporate governance and strategic transaction expertise
- Experience building or scaling legal functions
- History of developing in-house legal professionals
Benefits
- Inclusive and flexible work environment
- Competetive total compensation package
- Comprehensive group benefits with no waiting period
- Employer-funded retirement contributions
- Remote-first company culture
- Support for personal and professional development
- Flexible paid time off
- Home office setup reimbursement