Head of Commercial Legal

Build a Safer World.

TRM Labs provides AI-powered intelligence solutions that help public and private sector agencies investigate and disrupt crime. TRM's platforms enable investigators to trace illicit activity, build cases, and construct operating pictures of threat networks. Leading agencies and businesses worldwide rely on TRM to make the world safer and more secure.

As Head of Commercial Legal, you’ll be a key leader of TRM’s Legal team, which The Financial Times recently named one of the “Most Innovative In-House Legal Teams in North America.” You’ll partner closely with Go‑To‑Market, Product, Engineering, Operations, and leadership. And you will 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 in this role looks like 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 rather than one‑off fire drills.

AI Fluency is a Core Requirement at TRM-Legal

This role operates in an AI-native legal function. You are expected to actively use generative AI tools (e.g., Claude, ChatGPT, contract CLM/AI platforms) in your daily workflow—for drafting, contract analysis, legal research, and process design. “Willingness to learn” is not enough: we look for demonstrated fluency, sound judgment about when to deploy AI vs. when to escalate to a human, and a track record of building or improving AI-assisted workflows.

The impact you’ll have here

• 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, including hiring, structuring coverage, and developing team members at all levels

• Draft, review, and negotiate complex commercial agreements, with a primary focus on GTM 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 GC/CLO 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 — translating 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 actually used.

• Lead AI-enabled legal operations — 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 we’re looking for

• Experience. 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.

• Commercial & product depth. Significant experience negotiating complex B2B technology agreements in data and analytics‑heavy product environments.

• AI, data, and privacy literacy. Comfort advising on AI and data issues (e.g., data sources and permissions, privacy and security obligations, AI regulatory frameworks, content and IP questions), with the ability to quickly get smart on new regimes.

• Government and institutional customers (plus). Familiarity with public sector procurement, bank/vendor risk processes, or working with law enforcement or financial institutions is a strong plus.

• 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.

• AI‑native working style. Demonstrated comfort using AI tools for drafting, summarization, research, and workflow design, as well as good judgment about when a matter should bypass AI and go straight to a human.

• Communication and judgment. Excellent drafting and negotiation skills, with the ability to explain complex issues clearly to non‑lawyers and to calibrate advice for executives, GTM leaders, and technical teams.

• High ownership, low ego. 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.

• Qualifications. 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).

Application Instructions

If you’re interested in joining TRM, we encourage you to apply directly. Every application is reviewed by our Talent team.

Before applying, review the job description carefully and highlight the experience and impact that best demonstrate the required qualifications. Please also provide thoughtful and accurate answers to the application questions, as these will be used to evaluate your skills and qualifications for the role.

If you send your resume directly to someone at TRM, we can’t guarantee it will reach the appropriate hiring team. Applying directly is the best way to ensure your application will be considered.

Interviewing with TRM

Our process is designed to understand how you think, solve problems, and deliver impact, while allowing you to evaluate TRM. Most interview processes include a case study, an AI skills assessment, and a Leadership Principles interview.

• Recruiter Intro: Qualifications, motivations, and alignment with the role.

• Hiring Manager: Deep dive into your relevant experience, skills, and impact.

• First Round: 1–2 interviews focused on the skills most critical to the role.

• Final Round: Hands-on case study. This is usually a panel-style session where we go deeper into your craft, problem-solving, and alignment with TRM.

• References: Former colleagues who can provide insight into your work and impact.

• Offer: Congrats! Your recruiter will present the offer and compensation details.

• Welcome to TRM: We're excited to build a safer world with you!

Your recruiter will share your specific interview plan and preparation guidance along the way.

AI Fluency at TRM

AI fluency is a baseline expectation at TRM.

We believe AI meaningfully changes how top performers operate. We expect every team member to use AI to accelerate and reimagine their craft, not just automate surface tasks.

At TRM, AI fluency means you are among the top 10 percent of operators in your function in how you apply AI to:

• Accelerate repeatable workflows

• Structure and solve problems

• Improve output quality

• Increase speed and leverage

You will be evaluated on applied AI fluency during the interview process.

Life at TRM

We are building a safer world. That promise shows up in how we work every day.

TRM moves FAST. We are a high-velocity, high-ownership team that expects clarity, follow-through, and impact. People who thrive here are energized by hard problems, experimentation, and continuous feedback. If something takes months elsewhere, it will ship here in days.

Our work sits at the intersection of AI, national security, and fighting crime. The problems are complex, the stakes are real, and the environment evolves quickly. The pace and intensity of the work reflect the importance of the mission. As a result, the way we operate requires a high level of ownership, adaptability, collaboration, and creative problem-solving.

At TRM, you should expect:

• Priorities and targets to change quickly

• Operating with a high degree of ambiguity

• A high level of personal ownership and accountability

• Close collaboration across teams and functions

• Frequent, high-touch communication

• Creative problem-solving and out-of-the-box thinking

• A pace that rewards urgency, adaptability, and outcomes

This environment is energizing for people who enjoy building, solving hard problems, and making progress in situations that are not always fully defined. It also requires thriving in ambiguity, adjusting course as new information emerges, and maintaining focus and positivity in a fast-moving and intense environment.

We also recognize that this style of operating is not for everyone. If you are primarily optimizing for predictability or a consistently balanced workload, we encourage you to use the interview process to pressure-test whether this environment is truly the right fit. We want teammates who thrive here, not just survive here.

If you are excited by meaningful problems, motivated by ambitious goals, and energized by working alongside mission-driven colleagues, there is a good chance you will find TRM to be an exceptional place to grow and contribute.

Leadership Principles

We hire and grow against three leadership principles. They’re the standards for how we operate, treat each other, and make decisions.

• Impact-Oriented Trailblazer: We put customers first and move with speed, focus, and adaptability. We treat every plan like an experiment – test, ship, measure, and iterate quickly.

• Master Craftsperson: We care deeply about our craft. We balance speed with high standards, own outcomes end‑to‑end, and invest in getting better everyday.

• Inspiring Colleague: We add clarity and energy, not noise. We bring humility, candor, and a one‑team mindset — giving and receiving feedback to make the team stronger.

Join our Mission

At TRM, we care deeply about our craft. We are looking for individuals who want their work to matter, who experiment with speed and rigor, and who take pride in building a safer world for billions of people. If you’re excited by TRM’s mission but don’t check every box, we encourage you to apply — we hire for slope, judgment, and the will to learn fast.

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.

Privacy Policy and Additional Information

By submitting your application, you agree to allow TRM Labs to process your personal information in accordance with our Privacy Policy.

We collect the information you provide (such as your resume, work history, and contact details) solely for the purpose of evaluating your candidacy for current and future roles at TRM.

Because our hiring cycles for certain positions may span 24 to 36 months, we retain your personal information for up to 36 months from the date of your application. After that period, your data is deleted unless a different retention period is required or permitted by law.

If you are located in the European Economic Area, the United Kingdom, or another jurisdiction with applicable data protection laws, you have the right to access, correct, or request deletion of your personal data at any time before that period ends. To exercise any of these rights, contact us at [email protected].

To notify TRM Labs that you believe this job posting is non-compliant, please submit a report through this form (opens in a new tab). No response will be provided to inquiries unrelated to job posting compliance.

The use of AI tools of any kind (including but not limited to notetakers, interview assistants, and real-time coaching tools such as Otter.ai, Fireflies, Fathom, Cluey, or similar) during TRM interviews is not permitted without prior approval from TRM. TRM uses its own internal tools for note-taking to ensure a consistent and confidential experience for all candidates.

We are committed to providing reasonable accommodations to applicants with disabilities, and requests can be made via this form (opens in a new tab).

Recruitment agencies

TRM Labs does not accept unsolicited agency resumes. Please do not forward resumes to TRM employees. TRM Labs is not responsible for any fees related to unsolicited resumes and will not pay fees to any third-party agency or company without a signed agreement.