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 Legal who combines strong legal judgment with exceptional cross-functional leadership. This role sits at the intersection of Legal and Product Teams, reflecting our belief that legal strategy is deeply intertwined with how we build, ship, and scale our products.

You will partner directly with product, engineering, and design leadership to embed legal thinking into the core of our development process. The ideal candidate is not just a sharp legal mind, but a forward-thinking operator who leverages modern tools, including AI-powered solutions, to increase the team’s impact and velocity in a fast-moving environment.

What You'll Do:

• Serve as the embedded legal partner exclusively supporting the Product team to advise on legal requirements during product development cycles, feature launches, and platform decisions – acting as a true product partner, not just a downstream reviewer.
• Champion the adoption of AI-powered legal tools across the legal function – including contract review automation, regulatory monitoring platforms, AI legal research tools, and document drafting assistants – to dramatically increase team throughput and reduce external counsel spend.
• Build and continuously improve AI-enabled workflows for contract lifecycle management, NDAs, vendor agreements, and customer-facing terms.
• Use AI-assisted research tools to monitor regulatory changes in fintech, payments, BNPL, and consumer lending, and translate findings into actionable guidance for leadership.
• Draft, review, and negotiate a broad range of commercial agreements including partnership deals, vendor contracts, and financial institution agreements for the Product team..
• Manage and oversee outside counsel relationships, leveraging AI tools to reduce reliance on external resources and improve cost efficiency.
• Advise on intellectual property strategy, including patent filings, trademark management, and protection of proprietary technology.
• Partner with the Compliance and Finance teams to ensure legal alignment on regulatory matters, risk frameworks, and governance structures.
• Develop and deliver legal training to Product team members, using AI-enhanced materials and digital formats to maximize reach and retention.

What We Look For:

• J.D. from an accredited law school; active bar membership required.
• At least 8 years of legal experience, with significant in-house experience at a fintech, payments, or financial services company (or equivalent law firm advising such companies).
• Demonstrated enthusiasm for and hands-on experience with AI legal tools (e.g., Harvey, CoCounsel, Ironclad AI, Spellbook, or comparable platforms) – we are looking for someone who has already embraced AI in their practice.
• Proven ability to partner cross-functionally with product and engineering teams, translating complex legal concepts into clear, actionable guidance.
• Strong knowledge of laws and regulations governing consumer financial products, including FCRA, FDCPA, TCPA, EFTA, Reg E, Reg B, SCRA/MLA, and applicable state laws.
• Experience managing outside counsel and legal operations with a focus on efficiency and cost control.
• Strong analytical skills and comfort working with large datasets to support legal and regulatory analysis.
• Ability to thrive in a fast-paced, high-growth environment with competing priorities and evolving direction.
• Self-starter who takes ownership, drives initiatives to resolution, and communicates proactively with stakeholders.
• Excellent proficiency in Office, Google Workspace, and AI productivity tools.

About You:

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.
• You deliver results - you focus on the key inputs and deliver them with the right quality and in a timely fashion. Despite setbacks, you rise to the occasion and never settle.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

Compensation: The compensation range for the role is $175,000 - $250,000 including base and variable. Our ranges are very broad to accommodate all types of candidates and encourage growth. 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.

CCPA Disclosure: Sezzle Inc. is committed to protecting the privacy of our job applicants. In compliance with the California Consumer Privacy Act (CCPA), we inform California residents about the personal information we may collect, the purposes for its collection, and your rights under the CCPA. For details about the categories of personal information we collect and your rights under the CCPA, please visit the California Office of the Attorney General's CCPA page. By submitting your application, you acknowledge that you have read and understood this CCPA disclosure.

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. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.

#Li-remote

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 organization that builds consumer trust through responsible design.

What We Look For:

• Bachelor’s or Master’s degree in Law, Business Administration, or a related field; a J.D. or advanced degree is a plus.
• 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.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.
• Compliance certifications (e.g., CCEP, CRCM) preferred.

About You:

• You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
• You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust - you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit - you can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.
• You deliver results - you focus on the key inputs and deliver them with the right quality and in a timely fashion. Despite setbacks, you rise to the occasion and never settle.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

 Perks & 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

Compensation: The compensation range for the role is $175,000 - $250,000 including base and variable. Our ranges are very broad to accommodate all types of candidates and encourage growth. 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.

CCPA Disclosure: Sezzle Inc. is committed to protecting the privacy of our job applicants. In compliance with the California Consumer Privacy Act (CCPA), we inform California residents about the personal information we may collect, the purposes for its collection, and your rights under the CCPA. For details about the categories of personal information we collect and your rights under the CCPA, please visit the California Office of the Attorney General's CCPA page. By submitting your application, you acknowledge that you have read and understood this CCPA disclosure.

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. Sezzle recognizes and values the importance of diversity and inclusion in enriching the employment experience of its employees and in supporting our mission.

#Li-remote