Director of Legal - Product

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. 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. 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 Relentlessly high standards – you continually raise the bar and drive those around you to deliver great results. You’re not bound by convention – you develop new ways to do things. You need action – speed matters in business; many decisions and actions are reversible and do not need extensive study. 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, and once a decision is determined, you commit wholly. You deliver results – you focus on key inputs and deliver them with the right quality and on time. 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 set of perks but by the visible example of the people 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 may depend on factors such as education, experience, qualifications, and alignment with market data. Exceptional candidates may receive salaries outside 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. #J-18808-Ljbffr