Compliance Innovation Senior Strategist

Ramp•New York, NY

8d•$145,000 - $220,000

About The Position

Ramp's Financial Crime Compliance (FCC) team is seeking a senior investigator to help scale the systems used to handle compliance cases. The role applies deep experience in transaction monitoring (TM) alerts, AML investigations, complex fraud, and enhanced due diligence (EDD) reviews to develop and govern AI-enabled compliance systems. The strategist will partner closely with Engineering and the Head of FCC Tooling to test model outputs, label and calibrate results, and ensure automated decision points are documented and properly governed. The role remains connected to FCC's day-to-day workflows and participates in some of them, but is fundamentally focused on building repeatable systems and processes. The position works across TM, sanctions, complex fraud, and EDD automation initiatives. It involves developing structured workflows and evaluation processes, defining test coverage, documenting governance, and making evidence-based recommendations about automation and AI adoption. The role also translates compliance judgment into specifications and criteria that engineering teams can implement.

Requirements

At least 5 years of financial services experience in compliance, AML, or related regulatory advisory roles; fintech experience is preferred.
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 ability to ramp up quickly 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 specifications, test cases, and actionable evaluation criteria.
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.

Responsibilities

Partner with Engineering and the Head of FCC Tooling on automation experiments and AI initiatives across TM, sanctions, complex fraud, and EDD, turning prototype calibration into defined, repeatable evaluation processes.
Design and run labeling and tagging workflows for model outputs, such as TM alert dispositions and sanctions/PEP hit reviews, creating a structured and documented pipeline.
Define and maintain test sets, scenario coverage, and evaluation frameworks for compliance AI and agent tools in partnership with engineers.
Own documentation and governance for every automated or AI-assisted decision point.
Work with the FCC team to understand current workflows and guide innovative solutions.
Recommend automation and AI adoption decisions based on evidence, and escalate control-posture or model-risk trade-offs to compliance leadership.

Benefits

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