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Salary: USD 223,000 - 319,000 / annual
Tailscale is seeking a pragmatic, business-minded Head of Legal to build and lead the legal function through the company's next stage of growth. As Tailscale's senior legal leader, you will 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.
You will 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 commercial legal capabilities, including hiring a dedicated leader to own contracts and help scale the approach to commercial transactions.
Key responsibilities include: building and evolving the strategy, priorities, operating model, and team for Tailscale's legal function; serving as a trusted advisor to executives and cross-functional leaders, translating legal complexity into clear, practical business guidance; helping leaders identify material risks, evaluate tradeoffs, and move forward with appropriate safeguards; partnering with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams on company priorities; advising across corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations; building scalable legal processes, policies, systems, and decision-making frameworks; determining which legal capabilities should be developed internally, delegated to future team members, or supported by outside counsel; hiring and empowering legal team members; selecting and managing outside counsel across jurisdictions; coordinating guidance across jurisdictions; supporting strategic partnerships and business-critical matters; and anticipating emerging legal and regulatory developments.
Tailscale is a fully distributed company founded in 2019, backed by Accel, CRV, Insight, Heavybit, and Uncork Capital. The company makes safe connection effortless by delivering software that securely interconnects people and their devices. Teams of every size use Tailscale to protect networks, share access to internal tools, and more.
REQUIREMENTS:
- 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
- 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 work
- Broad business judgment and the 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 ability to make complex issues understandable to different audiences
- Sound judgment, curiosity, and 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
NICE TO HAVE:
- Experience in developer tools, infrastructure, cloud, networking, cybersecurity, data, or technically complex software environments
- Open-source software, licensing, developer ecosystems, APIs, integrations, marketplaces, or technology partnerships
- Product counseling, privacy, data governance, cybersecurity, intellectual property, or emerging technology
- AI-enabled products or use of AI within company operations
- Cloud, on-premises, self-hosted, or hybrid software offerings
- Data residency, sovereignty, localization, or cross-border data considerations
- Supporting employees or business operations across multiple countries
- Corporate governance, financing, strategic transactions, or board-related matters
- Building or scaling a legal function within a growth-stage company
- Hiring, developing, or leading in-house legal professionals
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
