Lead Commercial Counsel

Who this role is best for

Derived from job-description analysis by Serendipath's career intelligence engine.

Skills & requirements

About the role

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 Lead Commercial Counsel - GTM & Partnerships, you’ll be a key member 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

• Own complex commercial work. Lead negotiation and execution of high‑value commercial GTM and Partnership agreements, including master subscription/service agreements, statements of work, data and content licenses, strategic partnerships, and public sector contracts.

• Be a trusted legal partner to GTM. Support our global sales and partnerships teams on end‑to‑end deal strategy, contract counseling and contract escalations across government and enterprise customers.

• Navigate global regulatory complexity. Monitor and synthesize developments in areas such as privacy, AI regulation, law enforcement data access, sanctions/AML, public procurement, and platform/content rules, and translate them into clear requirements for Product, Engineering, GTM, and Operations.

• Build and maintain playbooks and templates. Own and continuously improve contract templates, fallback positions, and playbooks for commercial, data, and AI‑related matters; ensure they are implemented in CLM and are actually used by the team.

• Lead AI‑enabled legal operations. Design and iterate AI‑assisted workflows for improving legal efficiency and centralizing knowledge management—so that attorneys spend more time on judgment calls and less time on mechanical work.

• Drive cross‑functional alignment on risk. Help business stakeholders make informed decisions in ambiguous situations by clearly framing risk, impact, and options, and by escalating strategically to leadership when needed.

WHAT WE’RE LOOKING FOR

• Experience. 8+ 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 and providing hands‑on product counseling (ideally in data‑ and analytics‑heavy products).

• 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).

LIFE AT TRM

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

TRM moves quickly. 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 as we experiment and iterate

• Work that often requires 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 comfort navigating 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.

At the same time, many people find this work deeply rewarding. 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. Learn more: Interviewing at TRM: How We Hire and What Success Looks Like https://www.trmlabs.com/resources/blog/interviewing-at-trm-how-we-hire-and-what-success-looks-like

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.

LEADERSHIP PRINCIPLES

We hire and grow against three leadership principles. They’re the standa

Source: Trm Labs careers (Ashby)