Director of Legal - Product

Sezzle • United States, Remote, NH

17h • $175,000 - $250,000 • Remote

About The Position

Sezzle is 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.

Requirements

• 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.
• 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.
• Excellent proficiency in Office, Google Workspace, and AI productivity tools.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• Compensation range: $175,000 - $250,000 including base and variable.
• Sezzle Inc. is committed to protecting the privacy of our job applicants.
• Sezzle Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: Ph.D. or professional degree