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.

At TRM Labs, our Deployment Strategy team sits on the front lines of customer success, turning blockchain intelligence into measurable outcomes for the crypto businesses, financial institutions, and fintechs that rely on TRM. As a Senior Deployment Strategist for the North America private sector, you will own a portfolio of strategic commercial accounts, validate what success means for each customer, and drive adoption, retention, and expansion as their trusted advisor. What makes this role unique at TRM is the blend of senior IC autonomy, direct access to the economic buyers shaping crypto compliance programs, and the mandate to build the private‑sector playbooks the rest of the team will run.

Own the success of TRM's most strategic North America private-sector accounts, using AI (e.g., Claude) to turn customer calls and account data into 30/60/90-day success plans you validate against a named OSM and Economic Buyer. Protect and grow private-sector revenue: defend GRR by getting ahead of churn, and surface and validate expansion opportunities as CSQLs with Account Directors to grow NRR. Cut QBR and executive‑briefing prep from days to hours by using AI to draft briefs, decks, and follow‑ups that you refine with your own judgment.

Catch risk and prospect early by using AI to triage customer‑health and usage signals across your book daily. Make the whole team faster by building reusable AI prompts, templates, and workflows that other Deployment Strategists adopt.



Serve as the Voice of the Customer, using AI to synthesize feedback from calls and tickets into structured input that shapes the Product and Engineering roadmap. 5+ years in crypto businesses, financial institutions, or fintechs (compliance, investigative, or customer‑facing functions), with a habit of using AI tools to work faster.

A track record of owning senior stakeholder relationships and driving retention and expansion, supported by AI‑assisted account planning and reporting. Claude) to accelerate research, drafting, and analysis, with sound judgment on when to trust vs verify output. Clear communication that distills complex technical and investigative concepts for audiences from analysts to senior executives.

TRM's Customer Success org is globally distributed and works async‑first, thriving on Slack and thorough documentation, with weekly customer syncs, bi‑weekly health syncs, and regular pod calls.

The North America Deployment

Strategy pod owns the private‑sector book (crypto businesses, financial institutions, and fintechs) and operates as trusted advisors, not a ticket queue. Weekly customer syncs and bi‑weekly customer‑health syncs. Regular pod calls and customer QBRs.

Required online and collaboration hours: Occasional off‑hours monitoring for P0/P1 customer issues (not a formal on‑call rotation).

Travel Requirements: Frequency: For in‑person customer meetings, trainings, QBRs,



or events across North America; this role is remote and distributed. Within your first week with an existing customer, you capture their internal success metrics (OSMs) and draft a 30/60/90‑day success plan to achieve them, using AI to turn the call into a first draft. Within the same day a customer reports a bug, you coordinate across Product and Engineering to get answers and a fix, and close the loop with the customer.

Within the same day you spot an expansion signal on a call, you validate it against CSQL criteria and log the CSQL with the Account Director. Additionally, this role may be eligible to participate in TRM’s equity plan. We are building a safer world.

If something takes months elsewhere, it will ship here in days. Our work sits at the intersection of AI, national security, and fighting crime. As a result, the way we operate requires a high level of ownership, adaptability, collaboration, and creative problem‑solving.

A high level of personal ownership and accountability Creative problem solving and out‑of‑the‑box thinking This environment is energizing for people who enjoy building, solving hard problems, and making progress in situations that are not always fully defined. Improve output quality We put customers first and move with speed, focus, and adaptability. We treat every plan like an experiment – test, ship, measure, and iterate quickly.

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. Headquartered in San Francisco, TRM operates as a distributed‑first company with hubs in Los Angeles, San Francisco, New York, Washington D.

📌 Senior Deployment Strategist, Private Sector (Winnipeg)
🏢 TRM Labs
📍 Winnipeg