Commercial Legal Counsel

$250.58k - $313.56k per year

Coinscapture

Ottawa, ON

Commercial Legal CounselTailscaleRemoteCanadaLegal & CompliancePosted Oct 13, 2026Thank you for considering Tailscale. If this job description resonates with you, please apply. Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! 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 • 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. 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. 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 What We Offer • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! • Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. • Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation. • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration. • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. • Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! • A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. • Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents). Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter. Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit
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