Head of Commercial Legal

As Head of Commercial Legal at TRM Labs, you'll lead the legal team-recently named one of the "Most Innovative In-House Legal Teams in North America" by The Financial Times-and partner closely with Go-To-Market, Product, Engineering, Operations, and leadership. You'll own complex commercial negotiations, guide product development including AI-driven features and data usage, and design scalable, AI-assisted legal workflows that let the team focus on the hardest problems instead of repetitive tasks. Success means a Legal function that is fast, trusted, and deeply embedded in the business: deals close on time, product teams ship with clear guardrails, and routine work runs through well-designed, measurable processes.

What you'll do

• Manage and develop a team of commercial attorneys and legal professionals, including hiring, mentoring, setting priorities, and creating a culture of high performance and continuous improvement. Build and scale the commercial legal team in line with company growth and develop team members at all levels.
• Draft, review, and negotiate complex commercial agreements with a primary focus on Go-To-Market and partnership deals across enterprise and government customers, including master subscription agreements, data and content licenses, strategic partnerships, and public sector contracts. Oversee counterparty and vendor due diligence as part of the commercial intake and contracting process.
• Navigate cross-border commercial complexity, including GDPR, UK data protection law, EU regulatory frameworks, and APAC-specific requirements, in support of a globally distributed deal pipeline across the Americas, EMEA, and Asia.
• Partner closely with Sales, Partnerships, Product, and Engineering leadership to support deal velocity and provide practical, business-oriented legal guidance. Operate as a key decision-maker on commercial legal risk, with direct escalation path to the General Counsel on high-stakes matters.
• Support team members' professional growth through regular feedback, stretch assignments, and opportunities to take ownership of meaningful work.
• With legal team colleagues, navigate global regulatory complexity across privacy, AI regulation, law enforcement data access, sanctions/AML, and public procurement. Translate developments into clear requirements for cross-functional teams.
• Build and maintain commercial legal infrastructure, including contract templates, fallback playbooks, and CLM workflows, and ensure they are actively used.
• Lead AI-enabled legal operations by designing and iterating AI-assisted workflows that improve efficiency and free attorneys to focus on judgment-intensive work.
• Identify, frame, and escalate legal and business risks clearly, helping stakeholders make informed decisions in ambiguous situations.
• Stay current on legal developments affecting AI technologies, data products, and the financial crime compliance space.

What you bring

• 10+ years of legal experience with a strong mix of top-tier law firm and in-house work, ideally in SaaS, fintech, cybersecurity, or crypto/Web3.
• Significant experience negotiating complex B2B technology agreements in data and analytics-heavy product environments.
• Comfort advising on AI and data issues, including data sources and permissions, privacy and security obligations, AI regulatory frameworks, and content and IP questions, with the ability to quickly get smart on new regimes.
• Demonstrated fluency using AI tools for drafting, summarization, research, and workflow design, as well as sound judgment about when a matter should bypass AI and go straight to a human.
• Excellent drafting and negotiation skills, with the ability to explain complex issues clearly to non-lawyers and to calibrate advice for executives, Go-To-Market leaders, and technical teams.
• A builder mindset: you think in systems, workflows, and SLAs, and you enjoy turning ad hoc processes into scalable, documented ones, often with the help of CLM, Salesforce, and generative AI tools.
• The ability to manage a high volume of matters, balance competing priorities, and move quickly while maintaining high standards, all while being a collaborative, humble teammate.
• J.D. (or international equivalent) and active bar membership in good standing in at least one U.S. jurisdiction (or ability to register in-house where required).

Nice to have

• Familiarity with public sector procurement, bank/vendor risk processes, or working with law enforcement or financial institutions.

About TRM Labs

TRM Labs provides AI-powered intelligence solutions that help public and private sector agencies investigate and disrupt crime. The platform enables investigators to trace illicit activity, build cases, and construct operating pictures of threat networks. TRM is a Series C company with $220M in total funding, backed by Goldman Sachs, Bessemer, Y Combinator, Thoma Bravo, and others. Headquartered in San Francisco, TRM operates as a distributed-first company with hubs in Los Angeles, San Francisco, New York, Washington D.C., London, and Singapore.