Regulatory Program Lead, Canada

About the role

You will serve as the primary regulatory program owner for Block's Canadian regulated entities, Square Canada and Afterpay Canada, driving the full lifecycle of the compliance program under the oversight of the Chief Compliance Officer. You will act as a critical designee in all governance forums, Board meetings, and direct regulatory engagements, translating complex regulatory landscapes into actionable strategies. This role requires ownership of end-to-end program execution, integrating traditional compliance domains with emerging AI-enabled solutions to maintain regulatory alignment. You will lead cross-functional collaboration across Legal, Risk, Product, Operations, and Engineering to embed compliance into business processes. The position demands executive presence and the ability to communicate risk and regulatory posture clearly to senior leadership and Boards. You will be responsible for building and sustaining scalable, technology-enabled compliance functions that meet Canadian expectations and global Block standards.

Key facts

What you'll do

Drive the annual Canada Compliance Plan from end to end, including regulatory change management, continuous monitoring, risk assessments, and policy reviews to meet key milestones.

Lead the governance and tracking of regulatory commitments, audit actions, and findings, driving remediation efforts to closure while maintaining the compliance risk assessment framework and policies.

Serve as the designated compliance leader for Block's Canadian entities in governance forums, Board meetings, and all regulatory engagements with Canadian authorities.

Run the full compliance programs for Canada across AML/ATF (Square Canada MSB), RPAA, the PCI Code of Conduct, and consumer protection and privacy obligations under PIPEDA, CASL, and FCAC requirements.

Prepare Board and governance committee materials, converting multi-domain regulatory complexity into clear, decision-ready narratives for executive consumption.

Coordinate compliance training and develop targeted regulatory awareness materials for senior leadership, Boards, and business stakeholders to ensure organizational readiness.

Lead cross-functional regulatory programs in collaboration with Legal, Risk, Product, Operations, and Engineering to improve processes, drive automation, and implement AI-enabled compliance solutions.

Oversee FINTRAC registration and provide full support for regulatory examinations and audits for Canadian regulated entities.

Maintain and evolve the compliance risk assessment framework, ensuring policies and governance documentation reflect current regulatory expectations and business operations.

Champion the adoption of AI tools for regulatory analysis, program management, and monitoring to enhance efficiency and effectiveness within Canadian compliance operations.

Ensure alignment with Canadian payment systems knowledge and money services business obligations, including specific financial crime typologies and control environments.

Manage the execution of the Retail Payment Activities Act (RPAA) obligations and related record-keeping and reporting requirements.

Oversee compliance with the Payment Card Industry Data Security Standard and related controls within the Canadian context.

Support the development and implementation of privacy and data protection programs in line with Canadian federal and provincial legislation.

Act as a strategic partner to the business, advising on regulatory obligations and their impact on product development and go-to-market strategies.

Requirements

10+ years of progressive experience in compliance, financial crime, or regulatory affairs, which must include payments compliance at a regulated payments entity such as an MSB, payment service provider, acquirer, or comparable fintech like Square Canada.

Must have served in, or directly supported, a senior compliance leadership role such as CCO, Deputy CCO, Head of Compliance, CAMLO, or Deputy CAMLO at a regulated entity.

Deep knowledge of Canadian Anti-Money Laundering and Anti-Terrorist Financing legislation, including the PCMLTFA and FINTRAC guidance, as well as familiarity with related regulatory frameworks.

Comprehensive understanding of the Retail Payment Activities Act (RPAA), the Code of Conduct for the Payment Card Industry in Canada, and consumer protection frameworks enforced by FCAC, PIPEDA, and CASL.

Expertise in Canadian sanctions regimes, including the Special Economic Measures Act (SEMA) and the implementation of UN sanctions within the Canadian financial landscape.

Demonstrated executive presence and experience preparing, presenting, and defending Board-level compliance reporting to senior leadership and regulators.

Proven end-to-end working knowledge of payment systems and money services businesses, including payments-specific financial crime typologies, risk indicators, and control frameworks.

Hands-on, day-to-day use of AI tools for regulatory analysis, program management, and monitoring to drive efficiency and insight in compliance processes.

Strong ability to interpret regulatory requirements and translate them into practical controls, policies, and procedures for cross-functional teams.

Exceptional written and verbal communication skills, with the capability to distill complex regulatory issues into clear recommendations for diverse audiences.

Experience managing regulatory examinations, audits, and investigations, including preparing evidence, responses, and remediation plans.

Demonstrated ability to operate autonomously in a fast-paced, matrixed environment while managing multiple priorities and competing deadlines.

Commitment to maintaining current knowledge of evolving regulatory landscapes in Canada and globally as they relate to payments and financial services.