Head of Legal

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

• Develop and enhance the strategy, priorities, operational model, and team for Tailscale’s legal department.

• Provide counsel to executives and cross-functional leaders on legal and business issues.

• Assist leaders in identifying significant risks, assessing trade-offs, and implementing suitable safeguards.

• Collaborate with Product, Engineering, Security, Sales, Finance, People, Operations, Marketing, and other teams.

• Offer guidance on corporate governance, product development, open-source software, intellectual property, privacy, data, AI, security, employment, commercial relationships, compliance, and international operations.

• Create scalable legal processes, policies, systems, and decision-making structures.

• Decide which legal capabilities to develop internally, delegate to future team members, or seek assistance from external counsel.

• Recruit and empower legal team members, including establishing a dedicated commercial legal function.

• Choose and oversee outside counsel in all countries where Tailscale operates.

• Coordinate guidance across various jurisdictions and translate local requirements into actionable company practices.

• Support strategic partnerships, corporate initiatives, and critical business matters.

• Anticipate upcoming legal and regulatory changes and assist the company in preparing for them.

⛳️ Requirements

• Extensive legal experience, including substantial in-house experience within a technology firm.

• Proven track record of scaling legal functions in startup or high-growth settings.

• Juris Doctor degree.

• Active membership in at least one relevant bar or equivalent authorization to practice law.

• Progressive advancement in the scope, complexity, ownership, and influence of responsibilities.

• Broad business acumen and the ability to navigate legal issues beyond a single area of expertise.

• Experience advising executives and senior leaders on complex or impactful decisions.

• Capability to comprehend business objectives, identify significant risks, and suggest practical solutions.

• Experience collaborating with technical, operational, and commercial teams.

• Knowledge of legal considerations affecting a growing software or technology company.

• Experience working with outside counsel and translating specialized advice into clear business recommendations.

• Proven history of developing or enhancing legal capabilities, teams, programs, processes, or areas of practice.

• Excellent communication skills and the ability to simplify complex issues for diverse audiences.

• Sound judgment, curiosity, and confidence to constructively challenge when necessary.

• Comfort in navigating ambiguity and transitioning between strategic leadership and hands-on execution.

• Admission and good standing with at least one relevant state, provincial, or recognized bar association.

🏝️ Benefits

• Inclusive and flexible work environment with options for 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 setting.

• Virtual and in-person social gatherings.

• Corporate co-working program.

• Employer-funded retirement contributions that match employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually.

• Annual company retreat and team off-site meetings.

• Opportunities for team travel and collaborative efforts across distributed teams.

• $1500 USD annually allocated for professional development.

• Access to mentorship, coaching, and internal promotion opportunities.

• Flexible paid time off policy.

• Company-provided laptop, with the option of Mac or PC.

• Monthly reimbursement for home internet expenses.

• $500 USD budget for customizing home office workstation.

• Paid parental leave enhancements: 20 weeks for birthing parents and 16 weeks for non-birthing parents.