Head of Legal

Job not on LinkedIn

🔥 2 hours ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $298.8k - $427.5k / year

⏰ Full Time

🔴 Lead

⚖️ Legal Counsel / General Counsel

👻 Ghost score 20%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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

• 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

• 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