Compliance Innovation Senior Strategist

ABOUT RAMP Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. We automate how over $200B in annualized spend flows in and out of 70,000+ companies: authorizing payments, flagging risk, categorizing spend, and closing books. The problems are high-stakes, data-dense, and unforgiving. We hire people with high agency and high urgency. We look for slope over intercept. We care less about where you trained and more about what you’ve built. At Ramp, everyone is a builder who owns problems end to end and makes consequential decisions that shape the outcome. The median Ramp customer saves 5% and grows revenue 16% in their first year – far in excess of businesses operating without Ramp. We believe every ambitious company deserves the same. If you want to build systems that directly shape how companies move and manage billions, Ramp is the place to do it. ABOUT THE ROLE Ramp's Financial Crime Compliance (FCC) team is looking for a senior investigator ready to shift from running cases to scaling the systems that run cases. You've built real depth in TM Alerts, AML Investigations, Complex Fraud, and EDD Reviews; you know what a good escalation looks like, where analysts get stuck, and where automation actually holds up in production versus just looks good in a demo. In this role, you'll spend most of your time partnering with Engineering and the Head of FCC Tooling to turn that judgment into scaled AI systems: testing model outputs, labeling and calibrating results, and making sure every automated decision point is well-documented and properly governed. You'll stay close enough to FCC's day-to-day workflows and will partake in some of them, but this is fundamentally a builder role.   WHAT YOU'LL DO - Partner directly with Engineering and the Head of FCC Tooling on automation experimentation and AI initiatives across TM, sanctions, complex fraud, and EDD, moving prototypes from one-off calibration exercises to defined, repeatable evaluation processes. - Design and run labeling and tagging workflows for model outputs (e.g., TM alert dispositions, sanctions/PEP hit review) building a structured, documented pipeline in place of today's ad hoc process - Define and maintain test sets, scenario coverage, and evaluation frameworks for compliance AI/agent tools in partnership with the engineers building them - Own the documentation and governance layer for every automated or AI-assisted decision point - Work with the FCC team to understand current workflows to guide innovative solutions - Recommend automation and AI adoption decisions with evidence and escalate control-posture or model-risk trade-offs to compliance leadership   WHAT YOU NEED - 5+ years of financial services experience in compliance, AML, or related regulatory advisory roles, preferably in fintech - Demonstrated senior-investigator experience across TM Alerts, AML Investigations, Complex Fraud, and EDD Reviews - Direct experience testing, labeling, or evaluating AI/ML model outputs, or strong aptitude and demonstrated fast ramp-up if new to formal model evaluation - Strong AI fluency and data analytics skills - Comfort partnering with engineers day-to-day and ability to translate compliance judgment into build specs, test cases, and evaluation criteria engineers can act on - Strong project management and documentation rigor - Ability to scope an ambiguous automation problem, choose an approach, and deliver a durable outcome with minimal oversight   NICE-TO-HAVES - Data science background - Experience working with outsourced testing/QA partners on model tuning or signal collection BENEFITS AVAILABLE TO ALL FULL-TIME RAMP EMPLOYEES (GLOBAL) - Flexib