Commercial Legal Counsel - Tailscale

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

We are hiring a Commercial Legal Counsel to lead day-to-day commercial legal support as Tailscale continues to grow. You will partner closely with Sales, Partnerships, Finance, Security, Product, and Operations to help the company close business, manage risk, and build contracting practices that scale.

This role reports to the Head of Legal. The strongest candidate may be an experienced commercial counsel ready for broader ownership, a senior counsel who has led complex transactions and programs, or a commercial legal leader who can shape the function while remaining hands-on.

Key Responsibilities

• Agreement Ownership: Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements.
• Strategic Advising: Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths.
• Decision Support: Translate legal issues into clear options and recommendations that help teams make timely decisions.
• Process Scaling: Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources.
• Cross-Functional Partnership: Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies.
• Financial Collaboration: Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters.
• International Support: Support international transactions and coordinate with outside counsel when local or specialized expertise is needed.
• Data-Driven Improvement: Identify patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams.
• General Support: Contribute to other legal priorities as the company and legal function evolve.

What We Are Looking For

• 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 the ability to distinguish material business risk from issues that can be addressed through practical guardrails.
• A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.
• Clear, concise communication and the 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 that creates appropriate ownership and avoids making Legal an unnecessary bottleneck.

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 that arise 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 helping define the structure and priorities of a growing commercial legal capability.

What We Offer

• Inclusive, Flexible Environment: An environment where you can be your authentic self, with flexibility in how and when you work.
• Compensation & Equity: Competitive base salary, equity incentive plan, and comprehensive group benefits with no waiting period.
• Remote-First Work: Work fully remotely with a corporate co-working program (WeWork) and home office setup support ($500 USD customization stipend, company-owned laptop, and monthly internet reimbursement).
• Retirement Matching: Dollar-for-dollar match up to 0.75% of eligible compensation.
• In-Person Connections: Annual company retreats and team off-sites.
• Professional Development: $1,500 USD annually for professional development, plus mentorship and coaching.
• Paid Time Off: Flexible paid time off program.
• Parental Leave: Up to 20 weeks for birthing parents and 16 weeks for non-birthing parents.