Compliance Innovation Senior Strategist
About this role
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 available at reduced pay
Referral Instructions
If you are being referred for the role, please contact that person to apply on your behalf.
Other notices
Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.
Beware of recruiting scams: Ramp will only contact you through official @Ramp.com email addresses and will never ask for payment or sensitive personal information during the hiring process.