Director of Litigation and Regulatory

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: 

Sezzle is a publicly traded consumer finance company (Nasdaq: SEZL) building purchase-now-pay-later products for consumers who are underserved by traditional credit, and we are pursuing a de novo national bank charter. That combination puts us in front of regulators, plaintiffs' counsel, and state enforcement authorities more often than a company our size would normally be, and we handle almost all of it in-house. 

This role is for a lawyer who wants to own that work rather than route it. You will run litigation and pre-litigation disputes, manage regulatory inquiries and investigations from federal and state authorities, and serve as the legal owner of our privacy and data protection framework. You will have real autonomy on day one, direct access to the executive team, and the budget discipline of a lean function that brings in outside counsel deliberately rather than reflexively.

What You'll Do:

• Litigation and disputes

  • Manage consumer litigation, class actions, arbitrations, and commercial disputes from intake through resolution, including case strategy, discovery, and settlement posture.
  • Direct outside counsel where we use it: scope, budget, staffing, and strategy. You set the plan; they execute it.
  • Own litigation holds, ESI protocols, custodian identification, and the discovery process end to end.
  • Manage the small-claims and arbitration pipeline, and build the process improvements that keep volume from becoming a drag.
  • Identify the patterns behind repeat disputes and take them back to product, operations, and collections so the underlying problem gets fixed.

  Regulatory inquiries and investigations

  • Manage civil investigative demands, examination requests, subpoenas, and informal inquiries from the CFPB, FTC, state attorneys general, and state financial regulators.
  • Run productions: scope negotiation, data collection, privilege review, and delivery, working with engineering, data, and compliance.
  • Draft response letters, white papers, and advocacy submissions, and participate directly in regulator meetings.
  • Track the enforcement and supervisory landscape across BNPL, UDAAP, credit reporting, debt collection, and consumer disclosure, and translate it into concrete guidance for the business.
  • Support supervisory readiness as we build toward bank charter approval and the examination posture that follows.

  Privacy and data protection

  • Serve as legal owner of the privacy framework: policies, notices, records of processing, data mapping, and retention.
  • Advise on state comprehensive privacy laws, GLBA, FCRA, CAN-SPAM, TCPA, and the pixel and session-replay wiretap theories that continue to generate demand letters and class actions.
  • Review vendor and partner data flows, negotiate data protection terms, and handle escalated consumer privacy rights requests.
  • Partner with the Chief Compliance and Privacy Officer on incident response and on the operational privacy program.

  AI and how the function scales

  • Use AI to multiply your own throughput across research, document review, discovery, production, drafting, and regulatory tracking, and keep pushing what that stack can do.
  • Build durable tooling, not one-off prompts: skills, workflows, templates, and automations that outlive the matter they were built for and that the rest of the team can run.
  • Champion responsible AI adoption across the company. Legal is a builder here, not a brake. You will help business teams find ways to use these tools well and help set the guardrails that make that possible.
  • Advise on AI governance as a legal matter: model use, vendor diligence, data handling, disclosure, and the emerging regulatory picture.

  Advisory and cross-functional

  • Counsel product, marketing, engineering, and collections on live questions with practical answers, not memos that end in “it depends.”
  • Build the playbooks, templates, and internal training that let the function scale without adding headcount.

What We Look For:

• Bachelor's degree from an accredited law school and active bar membership in good standing in at least one US jurisdiction. You will need to satisfy in-house counsel registration requirements in your home state where they apply.
• 5 to 7 years of combined law firm and in-house experience.
• Substantive consumer financial services experience. You know Reg Z, Reg B, FCRA, FDCPA, TCPA, and UDAAP as working tools, not as an outline you once memorized.
• Demonstrated ownership of litigation matters and regulatory inquiries, including at least some experience running them without a partner above you.
• Clear, direct writing. You lead with the answer.
• Fluent and enthusiastic use of AI as a core part of how you practice. You are not experimenting at the margins; you build workflows, prompts, and tooling that materially change your own output, and you want to keep doing that here.
• 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.

Preferred Qualifications

• BNPL, fintech, consumer lending, or bank or bank charter experience.
• Experience with a de novo charter application, bank supervisory examinations, or a bank partnership model.
• Privacy credential (CIPP/US) or substantial privacy practice.

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. 

How we work

We are a small legal team supporting a company that moves quickly. We are business partners first: the job is to find the path to yes and manage the risk on the way there, not to catalogue reasons something cannot be done. We expect judgment, directness, and comfort making calls with incomplete information. We do not expect you to know everything on arrival, and we do expect you to say so when you do not.

We are all in on AI. This legal function is built on the premise that a small team using these tools well outperforms a large team that does not, and that is not aspirational here, it is how we already operate. We want someone who finds that energizing rather than threatening, who builds rather than waits for tooling to arrive, and who will help the rest of the company use AI well instead of policing it from a distance.

This role is fully remote within the United States. Our team operates on Central time, and we expect meaningful overlap with that schedule. Occasional travel is required for team meetings, regulator meetings, mediations, hearings, and depositions.

 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

Sezzle's Employee Privacy Policy: At Sezzle, we care about protecting your personal information. When you apply for a position with us, any data you share as part of the application process is handled in accordance with our Employee Privacy Policy, which also covers applicants. We encourage you to review it to understand how your information is collected, used, and safeguarded. You can read the full policy here: https://legal.sezzle.com/state-employee-privacy-policy.

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 Sezzle's Employee Privacy Policy: https://legal.sezzle.com/state-employee-privacy-policy. 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.

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Pay Range

$165,000 - $210,000 USD