[Hiring] Head of Legal @Tailscale

Role Description

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.

• Establish priorities, advise on important company and product decisions.
• Determine the right combination of internal talent, outside counsel, processes, and systems to support the business.
• Strengthen our commercial legal capabilities, including hiring a dedicated leader to own contracts and help scale our approach to commercial transactions.

Key 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 a range of matters including 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.

Qualifications

• Significant legal experience, including meaningful in-house experience within a technology company.
• 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 the ability to navigate legal issues beyond a single area of specialization.
• Experience advising executives and senior leaders on complex or consequential decisions.
• The 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.
• A 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.

Nice to Have

• Experience in developer tools, infrastructure, cloud, networking, cybersecurity, data, or another technically complex software environment.
• Experience with open-source software, licensing, developer ecosystems, APIs, integrations, marketplaces, or technology partnerships.
• Experience in product counseling, privacy, data governance, cybersecurity, intellectual property, or emerging technology.
• Experience with AI-enabled products or the use of AI within company operations.
• Experience with cloud, on-premises, self-hosted, or hybrid software offerings.
• Experience with data residency, sovereignty, localization, or cross-border data considerations.
• Experience supporting employees or business operations across multiple countries.
• Experience in corporate governance, financing, strategic transactions, or board-related matters.
• Experience building or scaling a legal function within a growth-stage company.
• Experience hiring, developing, or leading in-house legal professionals.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family.
• Remote first company with most teams working fully remotely.
• Employer-funded retirement contributions, matching dollar-for-dollar up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Opportunities to connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program to support work-life integration.
• Build-your-own home office setup with a company-owned laptop and $500 USD to customize your workstation.
• Paid parental leave program with top-ups for birthing and non-birthing parents.