Tailscale
Commercial Legal Counsel
Remote (Canada) +2 · Remote · Full-time · Posted Sep 18, 2026
- Location
- Remote (Canada)
Canada
United States - Experience
- Meaningful commercial transaction experience; no specific number of years stated.
- Education
- Law degree.
About the job
Leads day-to-day commercial legal support, negotiating agreements and helping teams close business, manage risk, and scale contracting practices.
What you'll do
- Negotiate commercial agreements and advise go-to-market teams on deal structure, contracting strategy, and risk.
- Develop scalable contracting resources and processes, including templates, playbooks, intake, and self-service tools.
- Partner with Security, Privacy, Product, Engineering, Finance, and Operations on commercial issues, including customer commitments involving AI and emerging technologies.
What they ask for
- 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 working closely with technology clients.
- Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment.
- Record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.
Nice to have
- Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, SaaS, or open-source products.
- Experience with enterprise sales, partnerships, marketplaces, integrations, contract lifecycle management, workflow automation, or commercial legal metrics.
Pay
$250,580 — $313,560 CAD (base salary)
AI focus
Partner on customer commitments involving artificial intelligence and emerging technologies; the hiring process also uses AI-assisted tools to screen and assess candidates, with decisions made by people.
Model-written summary · the original posting is authoritative