Senior Compliance Director – Payments & Digital Assets

OTT Pay Inc. is an established, fully funded fintech company focused on delivering streamlined financial payment solutions. With a strategic focus on both acquiring and issuing business, we are developing a mobile-first platform that offers a wide range of financial services, loyalty programs, and innovative products, including credit cards, payment solutions, e-commerce, gift cards, and more. We are a results-driven, forward-thinking organization that values goal orientation and continuous improvement.

At OTT Pay, you will find abundant opportunities for professional growth, working alongside a talented and diverse team from various industries. Our collaborative and innovative environment fosters learning and development, empowering you to excel and make a tangible impact. This is a unique chance to join a company dedicated to reshaping financial solutions for the future.

We are seeking a highly experienced Senior Compliance Director to lead our compliance strategy across the full payments spectrum: Card Issuing, Merchant Acquiring, Cross-Border Payments, and Digital Assets. This role is responsible for building and maintaining a robust compliance framework that covers current core business lines while preparing the organization for future innovation in digital assets and crypto-payments.

This is a key strategic role that directly impacts the scalability of our payment businesses, the company’s credibility with Tier 1 banks and card networks, and our readiness for investment banking due diligence and IPO.

What’s in it for you: 

Competitive Salary depending on experience, plus performance bonus.

Comprehensive Benefits: Extended Health, Dental, and Vision Benefits.

Security: Life and Disability Insurance.

Work-Life Balance: Generous Vacation Leave.

Wellness: Free use of onsite Gym and Sports Facilities, and regular Company Social Events.

Growth: Learning and Professional Development Support with tremendous opportunities for career advancement.

How you will contribute: 

Card Issuing & Acquiring Compliance

Issuing Governance: Lead compliance governance for credit, prepaid, and debit card programs. Interpret and implement Visa and Mastercard rules, BIN responsibilities, and issuer obligations.

Acquiring & Merchant Risk: Oversee Merchant Acquiring compliance, including KYB (Know Your Business) standards, prohibited merchant category (MCC) management, and underwriting policies.

Network & Dispute Management: Manage chargeback programs, fraud ratios, and dispute monitoring (VROL/Mastercom). Ensure network risk thresholds are monitored and maintained.

Settlement Compliance: Ensure compliance within settlement flows, including reserve management and the safeguarding of client funds in accordance with regulatory rules.

Cross-Border Payments & FX Compliance

International Frameworks: Design and manage compliance frameworks for cross-border payment flows, including regulatory compliance for FX, exchange rate mechanisms, and liquidity management.

Correspondent Banking: Manage due diligence requirements for correspondent banking relationships and ensure adherence to the FATF Travel Rule and local transfer regulations.

Sanctions & Screening: Oversee complex AML, CTF, and sanctions screening (OFAC, OSFI, UN, EU), including tuning logic for fuzzy matching and stripping warnings.

Digital Assets & Future-Ready Compliance

Crypto & Stablecoin Frameworks: Develop preliminary compliance frameworks for potential future entry into digital asset markets, including stablecoin issuance or crypto-payment gateways.

Blockchain Analytics: Advise on the integration of blockchain analytics tools (e.g., Chainalysis, TRM Labs) for on-chain transaction monitoring and wallet screening.

Regulatory Horizon Scanning: Monitor the evolving regulatory landscape for crypto-assets in Canada (OSC/CSA guidance) and globally (MiCA, VARA) to ensure future product

Regulatory & Authority Liaison ( Canada & Global)

Regulatory Strategy: Act as the primary liaison with regulators (FINTRAC), card networks, sponsor banks, and issuing partners.

RPAA Readiness: Lead the implementation and ongoing reporting for the Retail Payment Activities Act (RPAA) registration with the Bank of Canada.

Examination Management: Support government and regulatory examinations, audits, and remediation actions.

IPO & Investment Banking Support

Support IPO and pre-IPO compliance readiness.

Participate in investment banking and legal due diligence.

Clearly document entity obligations, responsibility boundaries, and risk disclosures.

What you bring to the table: 

Required Expertise

Minimum 10 years of experience in financial services compliance, with significant time spent in a leadership capacity.

Core Payments Expertise: Hands-on experience in both Card Issuing (Program Management, BIN Sponsorship) and Merchant Acquiring (KYB, Underwriting).

Digital Asset Knowledge: Demonstrated understanding of Cryptocurrency and Stablecoin regulations, including wallet infrastructure (custodial vs. non-custodial) and on-chain AML risks.

Regulatory Mastery: Expert knowledge of Canadian regulations (FINTRAC, PCMLTFA), with specific knowledge of the Retail Payment Activities Act (RPAA)

Cross-Border Mechanics: Deep understanding of SWIFT, SEPA, and local rail integrations, including correspondent banking due diligence.

Network Rules: Technical understanding of Visa/Mastercard Operating Regulations.

Build Capability: Proven ability to design compliance frameworks from the ground up, balancing regulatory requirements with business execution.

 Preferred Qualifications

Multi-jurisdiction compliance experience (North America plus Asia or Europe).

IPO or pre-IPO compliance experience.

Experience with BIN migration or sponsor-to-principal issuer transitions.

Office Location: 1123 Leslie Street, North York 

Schedule: Mon – Fri, 9:00am to 5:30pm 

OTT Financial Group is committed to fostering an inclusive and accessible environment where all employees feel valued and respected, and where every employee can realize their potential. We are committed to providing reasonable accommodation, if required, and will work with you to meet your needs. We appreciate all applicants for their interest; however, only those candidates selected for an interview will be contacted.