Compliance Innovation Senior Strategist

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.

• 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
• 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
• Data science background
• Experience working with outsourced testing/QA partners on model tuning or signal collection
• Health and wellness stipend
• Budget for intra-office travel
• Weekly coffee stipend
• One Medical annual membership
• Life, AD&D, and disability coverage

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