Head of Legal

Tailscale

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

Posted 9/18/2026full-timeRemote • Canada, United StatesLead💰 CA$298,820 - CA$427,460 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 cross-functional teams on complex legal matters.

Highest-signal resume keywords

In-House Legal ExperienceLaw DegreeActive Bar MembershipExperience Advising ExecutivesBuilding Legal Capabilities

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Corporate GovernanceComplianceIntellectual PropertyPrivacy LawData ProtectionOpen-Source SoftwareCommercial RelationshipsRisk ManagementLegal Process DevelopmentLegal Team Management

Soft Skills

Strong Communication SkillsSound JudgmentCuriosityConfidence in Challenging SituationsAbility to Navigate 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 matters
Help leaders identify material risks, evaluate tradeoffs, and implement 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 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 countries where Tailscale operates
Coordinate guidance across jurisdictions and translate local requirements into practical company practices
Support strategic partnerships, corporate initiatives, and business-critical matters
Anticipate emerging legal and regulatory developments and help the company prepare

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 the scope, complexity, ownership, and influence of work
Broad business judgment and ability to navigate legal issues beyond a single 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 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

Benefits

Comp & perks

Inclusive, flexible environment with flexibility in how and when you work
Competitive total compensation package including base salary and 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
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually
Annual company retreat and team off-sites
Team travel and distributed collaboration opportunities
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop, with choice of Mac or PC
Monthly home internet reimbursement
$500 USD home office workstation customization budget
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents