Regulatory Program Lead, Canada

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

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.

You Will

• 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

You Have

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

Technologies We Use and Teach

• Protecht (GRC / issue and risk management)
• AI tools (e.g., ChatGPT / OpenAI Enterprise / GitHub) for regulatory analysis, drafting, and process automation
• JIRA and Confluence (program and documentation management)
• Looker / Tableau (reporting and dashboards)

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We also consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations throughout the recruitment process. If you require an accommodation, let your recruiter know.  Want to learn more about what we’re doing to build an inclusive workplace? Check out our Inclusion & Diversity page.