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Commercial Legal Counsel

Tailscale· Office of the CEO
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Hybrid (Canada)CA$250.6k - CA$313.6kfull-timePosted 4w ago

About the role

Commercial Legal Counsel to lead day-to-day commercial legal support, partnering with Sales, Partnerships, Finance, Security, Product, and Operations to help close business, manage risk, and scale contracting practices.

Responsibilities

  • Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements.
  • Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths.
  • Translate legal issues into clear options and recommendations that help teams make 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 patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams.
  • Contribute to other legal priorities as the company and legal function evolve.

Qualifications

  • 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 the ability to distinguish material business risk from issues that can be addressed through practical guardrails.
  • A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.
  • Clear, concise communication and the ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams.
  • Comfort working independently, prioritizing competing demands, and making progress with incomplete information.
  • A collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck.

Skills

Required:Commercial contract negotiationDeal structuring and risk assessment
Nice to have:Contract lifecycle management

Benefits

  • An inclusive, flexible environment where you can be your authentic self.
  • A competitive total compensation package (base salary, equity incentive plan and variable commission for quota-based roles).
  • Comprehensive group benefits with no waiting period (health, vision, dental, and more).
  • Remote first company with opportunities for in-person collaboration where noted; corporate co-working program.
  • Employer-funded retirement contributions with matching up to 0.75% of eligible compensation.
  • Annual company retreat and opportunities for in-person collaboration across regions.
  • Personal and professional development support including $1500 USD annually for development; mentorship and internal promotion opportunities.
  • Paid time off and flexible paid time off program.
  • Build-your-own home office setup: laptop, internet reimbursement, and $500 USD to customize workstation.
  • Paid parental leave with top-ups (20 weeks birthing parents, 16 weeks non-birthing).
Last updated Sep 24, 2026. Interested? Apply on the company site.

About Tailscale

Secure Connectivity for AI, IoT & Multi-Cloud

The connectivity platform for devs, IT, and security teams. Zero Trust identity-based access that deploys in minutes and scales to every resource.

SecurityNetworkingZero TrustIdentity-based accessMulti-Cloud
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