Commercial Legal Counsel

The role

You will lead day-to-day commercial legal support by partnering with Sales, Partnerships, Finance, Security, Product, and Operations. You will own and negotiate commercial agreements and build contracting practices to help the company scale.

What you will do

• Own and negotiate a broad range of commercial 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
• 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
• Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, and insurance
• Support international transactions and coordinate with outside counsel
• Identify patterns in negotiations to improve cycle time and consistency
• Contribute to other legal priorities as the company and legal function evolve

Required qualifications

• A law degree
• Active membership in at least one applicable bar or equivalent authorization to practice law
• Meaningful experience advising technology companies on commercial transactions
• 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 addressed through practical guardrails
• A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties
• Clear, concise communication
• 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

Nice to have

• Commercial work involving developer tools, cloud infrastructure, networking, cybersecurity, software as a service, or open-source products
• Experience with enterprise sales, product-led growth, channel or technology partnerships, marketplaces, integrations, or application programming interfaces
• Familiarity with privacy, data protection, security, artificial intelligence, intellectual property, or product counseling issues
• 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 helping define the structure and priorities of a growing commercial legal capability

Benefits

• Base salary
• Equity incentive plan
• Comprehensive group benefits with no waiting period
• Health, vision, dental, and more
• Employer-funded retirement contributions (up to 0.75% of eligible compensation)
• Annual company retreat and team off-sites
• Professional development ($1500 USD annually)
• Mentorship, coaching, and internal promotion opportunities
• Flexible, paid time off
• Company-owned laptop (Mac or PC)
• Monthly home internet reimbursement
• $500 USD to customize workstation

Before you apply

• Hiring process uses AI-assisted tools to help screen and assess candidates

About the company

Tailscale delivers software that makes it easy to securely interconnect people and their devices. Founded in 2019, the company is fully distributed and backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.