Regulatory Program Lead, Canada

Block•Toronto, ON

2h•CA$125,900 - CA$188,900•Remote

About The Position

Block's Canada Compliance team is building a scalable, technology-enabled compliance function for our regulated Canadian entities - Square Canada and Afterpay Canada. Reporting to the Chief Compliance Officer, Canada, and serving as a designee of the CCO in governance forums, Board meetings, and regulatory engagements, you will be a “full-stack” compliance leader: driving the annual compliance plan end-to-end, overseeing frameworks across AML/ATF, sanctions, the Retail Payment Activities Act (RPAA), consumer protection, privacy, and payment card industry obligations, and co-building the AI-enabled programs and tools that keep both entities aligned with Canadian regulatory expectations and Block's global standards.

Requirements

10+ years of progressive experience in compliance, financial crime, or regulatory affairs, which must include payments compliance at a regulated payments entity - an MSB, payment service provider, acquirer, or comparable fintech such as Square Canada and serving in, or directly supporting, a senior compliance leadership role (CCO, Deputy CCO, Head of Compliance, CAMLO / Deputy CAMLO)
Deep knowledge of Canadian AML/ATF legislation (PCMLTFA, FINTRAC guidance), the RPAA, the Code of Conduct for the Payment Card Industry in Canada, consumer protection frameworks (FCAC, PIPEDA, CASL), and Canadian sanctions regimes (SEMA, UN sanctions)
Executive presence, with experience preparing and presenting Board-level compliance reporting and engaging directly with regulators through examinations and ongoing supervision
Direct end-to-end working knowledge of payment systems, money services businesses - including payments-specific financial crime typologies and controls
Hands-on, day-to-day use of AI tools for regulatory analysis, drafting, and process automation - with sound judgment about their limits
A builder mindset with proven leadership, people management, and stakeholder engagement capabilities in a fast-paced, growth-oriented environment; CAMS, ICA, or equivalent certification

Nice To Haves

knowledge of buy-now-pay-later compliance programs
Quebec regulatory regime
hands-on RPAA compliance
OSFI guidelines
the AUSTRAC / Australian AML/CTF regime
bilingual English/French

Responsibilities

Serve as the Regulatory Program Lead for Block's Canadian regulated entities, acting as a designee of the CCO in governance forums, Board meetings, and regulatory engagements
Lead end-to-end execution of the annual Canada Compliance Plan - regulatory change management, monitoring and testing, risk assessments, and policy reviews - delivering against key milestones and regulatory commitments
Run Canada's compliance programs across AML/ATF (Square Canada MSB), RPAA, the PCI Code of Conduct, and consumer protection and privacy obligations (PIPEDA, CASL, FCAC, provincial requirements), including FINTRAC registration and support for regulatory examinations and audits
Lead governance and tracking of regulatory commitments, audit actions, and findings - driving issue management and remediation through to closure - while maintaining the compliance risk assessment framework, policies, and governance documentation
Prepare Board and governance committee materials, translating multi-domain regulatory complexity into clear, decision-ready narratives for senior leadership
Lead cross-functional regulatory programs across Legal, Risk, Product, Operations, and Engineering, driving operational excellence through process improvement, automation, and AI-enabled compliance solutions
Coordinate compliance training and targeted regulatory awareness materials for senior leadership, Boards, and business stakeholders