VP of Legal - Product

Sezzle

4h • Remote

About The Position

We are seeking a talented and motivated VP 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.
• Excellent proficiency in Office, Google Workspace, and AI productivity tools.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: Ph.D. or professional degree
• Number of Employees: 101-250 employees