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

• Contract Negotiation: Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality agreements.
• Deal Strategy: Advise Sales and other go-to-market teams on deal structure, contracting strategy, risk, and escalation paths.
• Cross-Functional Collaboration: Partner with Security, Privacy, Product, and Engineering on customer commitments involving data, security, product functionality, integrations, artificial intelligence, and emerging technologies.
• Financial Alignment: Work with Finance and Revenue Operations on pricing terms, revenue considerations, procurement, insurance, and other commercial matters.
• Process Scaling: Build and improve templates, playbooks, fallback positions, approval thresholds, intake processes, and self-service resources.
• 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.

What We Are Looking For

• Credentials: A law degree and active membership in at least one applicable bar or equivalent authorization to practice law.
• Experience: Meaningful experience advising technology companies on commercial transactions, including in-house experience or equivalent experience working closely with technology clients.
• Scaling Track Record: Experience helping a legal function, contracting program, or business process scale in a startup or high-growth environment.
• Commercial Judgment: Strong judgment and the ability to distinguish material business risk from issues that can be addressed through practical guardrails.
• Negotiation Skills: A record of leading negotiations with sophisticated customers, partners, vendors, or counterparties.
• Communication: Clear, concise communication and the ability to build trust across Legal, Sales, Finance, Security, Product, and executive teams.
• Autonomy: Comfort working independently, prioritizing competing demands, and making progress with incomplete information.

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.
• Competitive Compensation: Base salary, equity incentive plan, and comprehensive group benefits with no waiting period.
• Remote-First Culture: Work from anywhere with wifi, participate in virtual and in-person social events, and access our corporate co-working program (WeWork).
• Retirement Match: Employer-funded retirement contributions matching dollar-for-dollar up to 0.75% of eligible compensation.
• In-Person Connections: Annual company retreats and team off-sites across Canada, the US, the UK, and Singapore.
• Professional Development: $1,500 USD annually for professional development, plus mentorship and coaching.
• Home Office Setup: Company-owned laptop, monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid Parental Leave: Parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).