Commercial Legal Counsel

Tailscale

. Lead day-to-day commercial legal support as Tailscale grows .

Posted 9/18/2026full-timeRemote • Canada, United StatesMid-LevelSenior💰 CA$250,580 - CA$313,560 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in commercial legal support, negotiation of complex agreements, and collaboration with cross-functional teams in a high-growth technology environment. Proficient in advising on data protection, security, and product functionality while ensuring compliance across multiple jurisdictions.

Highest-signal resume keywords

Law DegreeActive Bar MembershipExperience Advising Technology CompaniesNegotiation SkillsCommercial Legal Support

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Contract NegotiationData ProtectionRisk AssessmentLegal AdvisoryCommercial Transactions

Soft Skills

Clear CommunicationCollaborationJudgmentIndependenceTrust Building

Tools & Technologies

Contract Lifecycle Management ToolsWorkflow AutomationCommercial Legal Metrics

Certifications & Qualifications

Active Membership in Bar

Industry Keywords

Enterprise SalesCloud InfrastructureCybersecuritySoftware as a ServiceArtificial Intelligence

Tech Stack

Tools & technologies

CloudCyber Security

About the role

Key responsibilities & impact

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

What you’ll need

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
Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, software as a service, or open-source products is nice to have
Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or application programming interfaces is nice to have
Familiarity with privacy, data protection, security, artificial intelligence, intellectual property, or product counseling issues is nice to have
Experience supporting global customers or coordinating advice across multiple jurisdictions is nice to have
Experience selecting or implementing contract lifecycle management tools, workflow automation, or commercial legal metrics is nice to have
Experience mentoring colleagues or helping define a growing commercial legal capability is nice to have

Benefits

Comp & perks

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including a base salary and an equity incentive plan
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Remote-first work environment
Virtual and in-person social events
Corporate co-working program to visit WeWork or similar spaces
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
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 choice of Mac or PC
Monthly home internet reimbursement
$500 USD workstation customization allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents