Director of Compliance - Product

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.

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.

Requirements

• A J.D. degree is a must for this position.
• 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; familiarity with evolving BNPL regulatory guidance is a significant plus.
• 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.
• 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.
• Demonstrated experience working with Claude or equivalent large language model tools is required; candidates must be comfortable leveraging AI to enhance productivity, research, and communication.
• Compliance certifications (e.g., CCEP, CRCM) preferred.

Qualifications

• Must have a J.D. degree.
• At least 8 years of experience in a compliance leadership role within fintech, banking, or financial services.
• Hands-on experience with AI compliance and RegTech tools.
• Strong understanding of consumer financial protection regulations.
• Experience with regulatory examinations, audits, or supervisory reviews.
• Proven ability to work in agile environments.
• Strong analytical and problem-solving skills.
• Exceptional organizational and attention to detail skills.
• Comfortable working with product data, user flows, and technical documentation.
• Experience with AI tools like Claude.
• Preferred compliance certifications (CCEP, CRCM).

Skills

• Strong legal judgment and cross-functional leadership skills.
• Experience with AI compliance and RegTech tools.
• Knowledge of consumer financial protection regulations.
• Experience with regulatory examinations, audits, or supervisory reviews.
• Proven ability to work in agile environments.
• Strong analytical and problem-solving skills.
• Exceptional organizational and attention to detail skills.
• Experience with AI tools like Claude.

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

Pay

$175,000 - $220,000 USD
Specific compensation offered to a candidate may be dependent on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside of the posted ranges.

Equal Employment Opportunity

Sezzle Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, national origin, age, disability, genetic information, pregnancy, or any other legally protected status.

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