Commercial Legal Counsel

• Own and negotiate a broad range of commercial agreements, including enterprise customer, vendor, partner, marketplace, technology, data protection, and confidentiality 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 that help teams make 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 patterns in negotiations and use data to improve cycle time, consistency, and the experience of customers and internal teams.

• Contribute to other legal priorities as the company and legal function evolve.

• 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.

• 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.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale 's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range

$250,580 - $313,560 CAD