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Head of Legal

Tailscale· Office of the CEO
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Hybrid (Remote Canada)CA$298.8k - CA$427.5kfull-timePosted 4w ago

About the role

Senior legal leader responsible for building and leading Tailscale's legal function during growth, advising executives, managing risk, and developing scalable legal capabilities including a dedicated commercial legal capability.

Responsibilities

  • Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function.
  • Serve as a trusted advisor to executives and cross-functional leaders, translating legal complexity into clear, practical business guidance.
  • Help leaders identify material risks, evaluate tradeoffs, and move forward with appropriate safeguards.
  • Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams on company priorities.
  • Advise across corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations.
  • Build scalable legal processes, policies, systems, and decision-making frameworks without creating unnecessary complexity.
  • Determine which legal capabilities should be developed internally, delegated, or supported by outside counsel.
  • Hire and empower legal team members, including a dedicated commercial legal capability.
  • Select and manage outside counsel across operating countries, balancing expertise, responsiveness, cost, and business impact.
  • Coordinate guidance across jurisdictions and translate local requirements into practical, consistent company practices.
  • Support strategic partnerships, corporate initiatives, and other business-critical matters as the company grows.
  • Anticipate emerging legal and regulatory developments and help the company prepare for what comes next.

Qualifications

  • Significant legal experience, including meaningful in-house experience within a technology company and a track record of helping legal functions scale in startup or high-growth environments.
  • A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.
  • Progressive growth in the scope, complexity, ownership, and influence of your work.
  • Broad business judgment and ability to navigate legal issues beyond a single area of specialization.
  • Experience advising executives and senior leaders on complex or consequential decisions.
  • Ability to understand business goals, identify material risks, and recommend practical paths forward.
  • Experience partnering effectively with technical, operational, and commercial teams.
  • Familiarity with the legal considerations facing a growing software or technology company.
  • Experience working with outside counsel and turning specialized advice into clear recommendations for the business.
  • Track record of building or improving legal capabilities, teams, programs, processes, or areas of practice.
  • Strong communication skills and the ability to make complex issues understandable to different audiences.
  • Sound judgment, curiosity, and the confidence to challenge constructively when needed.
  • Comfort operating in ambiguity and moving between strategic leadership and hands-on execution.
  • Admission and good standing with at least one applicable state, provincial, or other recognized bar association.

Skills

Required:Legal leadership and strategyCross-functional partnershipCorporate governanceContract and commercial law

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package (base salary, equity incentive plan, and variable commission for quota-based roles).
  • Comprehensive group benefits with no waiting period (health, vision, dental, and more).
  • Remote first company with optional in-person collaboration noted per role.
  • Employer-funded retirement contributions with matching up to 0.75% of eligible compensation.
  • Company retreat and team off-sites; in-person collaboration across regions.
  • $1500 USD annual for professional development; mentorship and internal promotion opportunities.
  • Paid time off with flexible PTO program.
  • Build-your-own home office setup including company laptop choice, internet reimbursement, and workstation stipend.
  • Paid parental leave with top-ups (20 weeks birthing parents, 16 weeks non-birthing).
Last updated Sep 24, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
Company profileWebsite

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