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Salary: CAD 250,580 - 313,560 / annual
Tailscale is a secure networking platform built on WireGuard that helps teams of all sizes securely interconnect people and devices. The company is fully distributed, founded in 2019, and backed by top-tier VCs including Accel, CRV, and Insight.
You will serve as Commercial Legal Counsel, reporting to the Head of Legal, and lead day-to-day commercial legal support as the company scales. This is a hands-on role with significant ownership—you will partner closely with Sales, Partnerships, Finance, Security, Product, and Operations to help close business, manage risk, and build contracting practices that scale.
Key responsibilities include:
- Owning and negotiating a broad range of commercial agreements: enterprise customer contracts, vendor agreements, partner deals, marketplace terms, technology agreements, data protection, and confidentiality agreements
- Advising Sales and go-to-market teams on deal structure, contracting strategy, risk assessment, and escalation paths
- Translating legal issues into clear options and recommendations to enable timely business decisions
- Building and improving templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources
- Partnering with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, AI, and emerging technologies
- Working with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, and insurance
- Supporting international transactions and coordinating with outside counsel for specialized expertise
- Identifying negotiation patterns and using data to improve cycle time, consistency, and stakeholder experience
- Contributing to broader legal priorities as the company and function evolve
The strongest candidates may be experienced commercial counsel ready for broader ownership, senior counsel who has led complex transactions and programs, or commercial legal leaders who can shape the function while remaining hands-on.
Requirements:
- 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 (in-house or equivalent experience with technology clients)
- Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment
- Strong judgment 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
- Comfort working independently, prioritizing competing demands, and making progress with incomplete information
- Collaborative approach that creates appropriate ownership and avoids making Legal an unnecessary bottleneck
Nice to have:
- Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, SaaS, or open-source products
- Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or APIs
- Familiarity with privacy, data protection, security, AI, IP, or product counseling in technology transactions
- Experience supporting global customers or coordinating advice across multiple jurisdictions
- Experience selecting or implementing contract lifecycle management tools, workflow automation, or commercial legal metrics
- Experience mentoring colleagues or defining the structure and priorities of a growing commercial legal capability
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
