Commercial Legal Counsel

Remote (Canada)RemoteFull-time$187k2026-09-30 → 2026-11-10

Core

Lead day-to-day commercial legal support for a growing technology company, partnering with Sales, Partnerships, Finance, and Security to close business, manage risk, and build scalable contracting practices.

Role type

Senior Commercial Legal Counsel (In-house)

Builds

Enterprise customer, vendor, partner, marketplace, and technology agreements; scalable contracting playbooks and templates.

Domain

Technology (SaaS, cloud infrastructure, networking, cybersecurity, AI)

Required skills

Commercial contract negotiation, deal structuring, risk assessment, legal strategy, template development, cross-functional collaboration, data-driven process improvement, international transaction support, stakeholder management

Preferred skills

Developer tools experience, enterprise sales support, privacy and data protection expertise, global customer support, contract lifecycle management tools, mentoring

Technologies

Contract lifecycle management tools, workflow automation platforms

Responsibilities

Negotiate broad range of commercial agreements; advise go-to-market teams on deal structure and risk; build and improve legal templates and processes; partner with Security and Product on data and security commitments; support international transactions; identify negotiation patterns to improve cycle time.

Seniority

Senior, hands-on IC with potential for broader ownership

About Tailscale

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.