Commercial Legal Counsel

🕒 September 18

🌐 United States, Canada – Remote

🇺🇸 United States – Remote 🇨🇦 Canada – Remote

💵 $187k - $234k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

⚖️ 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

• Lead day-to-day commercial legal support as Tailscale grows • Own and negotiate enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements • Advise Sales and go-to-market teams on deal structure, contracting strategy, risk, and escalation paths • Translate legal issues into clear options and recommendations for timely decisions • Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources • Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies • Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters • Support international transactions and coordinate with outside counsel when local or specialized expertise is needed • Identify negotiation patterns and use data to improve cycle time, consistency, and customer and internal-team experience • Contribute to other legal priorities as the company and legal function evolve • Report to the Head of Legal

🎯 Requirements

• A law degree and active membership in at least one applicable bar or equivalent authorization to practice law • Meaningful experience advising technology companies on commercial transactions, including in-house experience or equivalent experience working closely with technology clients • Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment • Strong judgment and ability to distinguish material business risk from issues addressable through practical guardrails • Record of leading negotiations with sophisticated customers, partners, vendors, or counterparties • Clear, concise communication and ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams • Ability to work independently, prioritize competing demands, and make progress with incomplete information • Collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck

🏖️ Benefits

• Base salary, equity incentive plan, and variable commission for quota-based roles • Comprehensive health, vision, and dental benefits with no waiting period • Flexible 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 • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off program • Company-owned laptop (Mac or PC) • Monthly home internet reimbursement • $500 USD home office customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents