Head of Legal

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Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Tailscale is looking for a pragmatic, business-minded Head of Legal to build and lead our legal function through our next stage of growth.

As Tailscale’s senior legal leader, you’ll partner with executives and teams across the company to navigate complex legal and business considerations, manage risk, and build the capabilities needed to support a growing, globally distributed technology company.

This is an opportunity to shape how Legal operates at Tailscale. You’ll establish priorities, advise on important company and product decisions, and determine the right combination of internal talent, outside counsel, processes, and systems to support the business. An early priority will be strengthening our commercial legal capabilities, including hiring a dedicated leader to own contracts and help scale our approach to commercial transactions.

You may already lead a broad legal organization, or you may be an experienced legal leader who has taken on progressively greater responsibility and is ready to step into the top legal role for the first time.

• 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 a range of matters that may include 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 to future team members, or supported by outside counsel.

• Hire and empower legal team members, including building a dedicated commercial legal capability.

• Select and manage outside counsel across the countries where Tailscale operates, 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 Tailscale continues to grow.

• Anticipate emerging legal and regulatory developments and help the company prepare for what comes next.

• Significant legal experience, including