Director of Compliance - Product

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 data use — ensuring each release meets requirements.Establish and oversee post-launch product compliance monitoring protocols to assess whether deployed features operate as intended from a regulatory standpoint, and identify defects or drift requiring corrective action.Ensure product compliance issues are recorded, tracked, and escalated appropriately, with clear ownership and timelines for remediation across the product and engineering teams.Prepare and communicate product compliance reporting to senior leadership, and the Chief Compliance Officer, translating product-level compliance status and risk exposure into clear, executive-ready insights.Develop and deliver product compliance training and awareness programs to product managers, engineers, and designers, using AI-assisted tools and digital formats to build compliance fluency across product development teams.Champion a product culture where compliance is treated as a competitive advantage and quality standard — not a blocker — fostering a mindset across the Product