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Head of Legal

Tailscale

Canada · United StatesListed todayPosted by the employer Sep 18, 2026Listing ends Dec 28, 2026

Compensation: CA$298,820–CA$427,460
Location: Canada or United States
Fully remoteMore jobs: Canada More jobs: United States
Employment: Full-time
Category: Finance / Legal / People

Role skills

privacy compliance governance commercial legal legal product counseling security scaling

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About the job

6 min read7 sections

Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

About Tailscale

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.

About the Role

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.

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 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.

What We Are Looking For

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.
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

We do not expect candidates to bring experience in every area below. Relevant experience may include:

Developer tools, infrastructure, cloud, networking, cybersecurity, data, or another technically complex software environment.
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 the 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.

How You’ll Work

At Tailscale, Legal is a thoughtful and pragmatic partner. You’ll seek to understand the goals behind the work, help teams evaluate tradeoffs, and build frameworks that enable people to make sound decisions with increasing independence.

You’ll thrive in this role if you enjoy building, are curious about technical products, and want to shape a legal function as the company grows. You know when to engage directly, when to bring in specialized expertise, and when to empower others to lead.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Range $298,820 — $427,460 CAD

What We Offer

An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness .

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About Tailscale

Tailscale is proud to be a fully remote company with team members in the United States, Canada and the United Kingdom. We recognize an inclusive workplace start…