VP of Compliance - Product

Sezzle

4h • Remote

About The Position

We are seeking a talented and motivated VP of Compliance 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.

Requirements

• Bachelor’s or Master’s degree in Law, Business Administration, or a related field.
• At least 8 years of experience in a compliance leadership role within fintech, banking, or financial services.
• Demonstrated hands-on use of AI compliance and RegTech tools (e.g., AI-assisted product review workflows, compliance workflow automation) to streamline and scale a product compliance function.
• Strong working knowledge of consumer financial protection regulations relevant to product features, including TILA/Reg Z, FCRA, EFTA/Reg E, ECOA/Reg B, UDAAP, TCPA, and applicable state consumer protection laws.
• Experience participating in or supporting regulatory examinations, compliance audits, or supervisory reviews, with the ability to speak credibly about product design decisions and the compliance controls embedded within them.
• Proven ability to operate effectively within agile product development environments; experience translating regulatory requirements into product specifications, acceptance criteria, or technical control requirements that engineering teams can execute.
• Strong analytical and problem-solving skills, with the ability to assess compliance risk at both the feature level and portfolio level, including comfort working with product data, user flows, and technical documentation.
• Exceptional organizational skills with strong attention to detail; able to manage multiple concurrent product reviews, compliance workstreams, and stakeholder relationships without losing accuracy or momentum.
• Exceptional organizational skills with strong attention to detail and accuracy.
• Ability to thrive in a dynamic, fast-paced environment with competing priorities and evolving direction.
• Self-starter who takes ownership, drives initiatives to resolution, and raises awareness proactively when challenges arise.
• Excellent proficiency in Office, Google Workspace, and AI productivity tools.

Nice To Haves

• A J.D. or advanced degree is a plus.
• Familiarity with evolving BNPL regulatory guidance is a significant plus.
• Compliance certifications (e.g., CCEP, CRCM) preferred.

Responsibilities

• 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 organization that builds consumer trust through responsible design.

Benefits

• Unlimited PTO, volunteer hours and sabbatical
• Life, STD/LTD, medical, dental and vision insurance
• Highly discounted LifeTime gym membership
• 401k with match of 6%
• Collaborative fun co-workers
• The opportunity to join the fastest growing FinTech alongside a team of motivated and driven individuals

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 101-250 employees