Hillary Pressman
Risk Lead @Loop Financial
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WORK HISTORY
Risk Lead @Loop Financial
Toronto, ON, CA
Led the risk function at Loop Financial, a cross-border fintech offering bank accounts, credit products, payments, and foreign exchange. Served as the senior risk hire, providing risk advisory and oversight across credit risk, operational risk, fraud, and AML/ATF compliance- Supported EQ Bank (sponsor bank) through onboarding due diligence, ongoing audits, and monthly reporting; fielded diligence requests from two prospective US bank partners, supporting the LSBx partnership decision- Contributed to investor due diligence processes, preparing materials and responding to requests covering fraud controls, compliance program, credit policy, and portfolio performance- Led Loop\'s registration under Canada\'s Retail Payment Activities Act (RPAA), a new federal regulation, as one of the first cohorts of registered payment service providers- Served as primary coordinator for a FINTRAC compliance effectiveness review with a third-party auditor, preparing materials and responding to regulatory information requests end to end- Surfaced risk findings that changed outcomes: drove early identification and remediation through fraud investigation, compliance monitoring, and enhanced due diligence, with escalation to offboarding where necessary- Reduced overdue lending portfolio balance by 24% by migrating collections from manual spreadsheets to Salesforce and optimizing workflows- Produced written risk assessments, investigation findings, and advisory recommendations for leadership, translating complex risk findings into actionable guidance for decision makers- Developed risk-based deposit clearing framework balancing fraud exposure, customer experience, and revenue goals
EDUCATION
Université catholique de Louvain
Cours isolés en gestion
General Assembly
Data Analytics
McGill University
Bachelor of Commerce, International Management; Geography
University of Toronto
Certificate of Risk Management
SKILLS
ABOUT HILLARY PRESSMAN
Risk and compliance professional with 14+ years building and scaling operational risk programs across fintech, lending, payments, and financial services in both Canada and the US. Most of my career has been at growth-stage fintech lenders covering merchant and counterparty risk, KYC/KYB onboarding, fraud monitoring, AML compliance, and credit risk, at Loop Financial, Uplift (now Upgrade Flex Pay), FinanceIt, Tesla, and Ford Credit.Across these roles I\'ve experienced institutional due diligence from both sides of the table. I\'ve had my risk controls evaluated firsthand by lenders, investors, acquiring firms, and sponsor banks. I\'ve also conducted operational diligence as a practitioner, assessing merchants, borrowers, and counterparties at scale.Interested in risk advisory and due diligence, including evaluating fintech partnerships and investments, and advising on operational risk strategy and controls.
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