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) Flexible PTO Centralized home-office equipment ordering Health and wellness stipend Budget for intra-office travel Weekly coffee stipend United States 100% medical, dental & vision insurance coverage for you, with partial coverage for dependents One Medical annual membership 401(k), including employer match on contributions made while employed by Ramp Fertility HRA (up to $10,000 per year) Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay Pet insurance In-office perks: lunch, snacks, drinks, and more Relocation expense coverage to NYC or SF (if needed) Canada Group medical, dental, and vision coverage through Sun Life Life, AD&D, and disability coverage Fertility drug coverage (up to $4,000 lifetime) Group Retirement Plan with employer match (RRSP + DPSP) Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay, with additional time available at reduced pay Employee Assistance Program and virtual care through Lumino Health United Kingdom Private medical insurance through Freedom Elite Virtual GP and at-home care via eMed x Livi Workplace pension through Penfold, with salary sacrifice option Parental leave: up to 16 weeks (birthing + bonding) or 8 weeks (bonding only) at 100% pay with additional time availabl