Director, Litigation and Regulatory

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.

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.

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.

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.

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.

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.

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.

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.

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.