Director of Compliance - Product
Summary of Relevant Experience
Summary of Experience – Director of Compliance - Product @ Sezzle
- JD/MBA-credentialed compliance and benefits counsel who has built and led regulatory compliance programs across multiemployer funds and a Fortune 500 insurer, with direct accountability to C-suite executives.
- In-house legal strategist who has managed complex litigation, regulatory risk assessments, and compliance frameworks in heavily regulated environments, translating dense statutory requirements into operational controls.
- Cross-functional counsel who has partnered with product, operations, and HR teams on M&A due diligence and plan governance, embedding compliance requirements into design and execution workflows from the outset.
- Regulatory compliance advisor experienced with federal and state mandated frameworks including ERISA, HIPAA, and employment law, with demonstrated ability to manage outside counsel and deliver executive-ready compliance reporting.
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Why this is a fit
This role targets product compliance in fintech (BNPL/consumer lending regulations like TILA, FCRA, UDAAP) with 8+ years required, while your background centers on ERISA, employee benefits, and HIPAA — a different compliance domain — and your ~4 years of experience falls well short of the 8-year minimum for this director-level role.
About the role
About Sezzle: With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping! About the Role: We are seeking a talented and motivated Director of Compliance - Product who combines strong legal judgment with exceptional cross-functional leadership. This role sits at the intersection of compliance product development, ensuring that compliance is not a late-stage checkpoint but an integral part of how we design and deliver our products. You will work side-by-side with product managers, engineers, and data teams to build compliance into our processes from day one. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team, with abundant prospects for career advancement. The ideal candidate is a forward-thinking compliance leader who actively leverages AI tools to streamline and scale product compliance assessment, development, and monitoring to foster increased speed to market, and support a world-class compliance program. What You'll Do: Own and drive the product compliance function end-to-end, ensuring all new and existing product features comply with applicable federal and state laws and regulations governing Sezzle’s consumer lending, BNPL, and payment products. Serve as the embedded compliance partner exclusively supporting the Product team to advise on compliance requirements during product development cycles; serving as a compliance partner from ideation through launch and post-launch iteration. Champion the adoption of AI-powered compliance and RegTech tools – including automated regulatory change monitoring, AI-assisted product review workflows, and smart audit trail systems; to scale the product compliance function’s capacity and enable deeper analytical coverage across the product portfolio. Leverage AI research tools to maintain current awareness of regulatory developments affecting consumer-facing product features, including changes to FCRA, TILA/Reg Z, EFTA/Reg E, UDAAP, ECOA/Reg B, TCPA, state consumer protection laws, and emerging regulations governing BNPL products. Partner with the product leadership to discuss and anticipate regulatory change, sequencing compliance work alongside feature development, and ensure the organization is never caught flat-footed by new requirements. Conduct product-level regulatory compliance risk assessments for new features and product changes; identify control gaps, evaluate the compliance impact of product decisions, and develop risk mitigation strategies that allow the business to move quickly without cutting corners. Develop and maintain product compliance standards and control frameworks that define how regulatory requirements translate into product design decisions, feature specifications, and release criteria. Collaborate with product managers, engineers, and UX designers to translate compliance requirements into actionable acceptance criteria, user story guardrails, and practical implementation guidance that product teams can execute against. Lead product-level compliance review and sign-off for features touching consumer disclosures, adverse action, credit reporting, payment authorization, marketing claims, and dat