Head of Legal

Tailscale

. Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function .

Posted 9/18/2026full-timeRemote • United States, CanadaLead💰 $223,000 - $319,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive legal expertise with a focus on technology companies, including corporate governance, compliance, and intellectual property. Proven ability to build and scale legal functions while advising executives on complex business decisions and risks.

Highest-signal resume keywords

Significant Legal ExperienceIn-House Experience Within TechnologyLaw DegreeActive Bar MembershipExperience Advising Executives

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Corporate GovernanceComplianceIntellectual PropertyPrivacy LawData ProtectionOpen-Source SoftwareCommercial RelationshipsLegal Process DevelopmentRisk AssessmentLegal Capability Building

Soft Skills

Strong Communication SkillsSound JudgmentCuriosityAbility to Operate in Ambiguity

Certifications & Qualifications

Active Bar Membership

Industry Keywords

Technology CompanyHigh-Growth EnvironmentLegal Function ScalingOutside Counsel ManagementStrategic Partnerships

About the role

Key responsibilities & impact

Build and evolve the strategy, priorities, operating model, and team for Tailscale’s legal function
Advise executives and cross-functional leaders on legal and business considerations
Help leaders identify material risks, evaluate tradeoffs, and apply appropriate safeguards
Partner with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams
Advise on 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
Determine which legal capabilities should be developed internally, delegated to 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
Coordinate guidance across jurisdictions and translate local requirements into consistent company practices
Support strategic partnerships, corporate initiatives, and other business-critical matters
Anticipate emerging legal and regulatory developments and help the company prepare
Shape how Legal operates at Tailscale as the company grows

Requirements

What you’ll need

Significant legal experience, including meaningful in-house experience within a technology company
Track record of helping legal functions scale in startup or high-growth environments
A law degree
Active membership in at least one applicable bar or equivalent authorization to practice law
Progressive growth in scope, complexity, ownership, and influence
Broad business judgment 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 with technical, operational, and commercial teams
Familiarity with legal considerations facing a growing software or technology company
Experience working with outside counsel and turning specialized advice into clear business recommendations
Track record of building or improving legal capabilities, teams, programs, processes, or practice areas
Strong communication skills
Sound judgment and curiosity
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

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including base salary and an equity incentive plan
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Remote-first work environment with flexible work arrangements
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
Annual company retreat and team off-sites
$1,500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off
Company-owned laptop (Mac or PC)
Monthly home internet reimbursement
$500 USD home office setup allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
Accessible and inclusive hiring process with accommodations available