Vice President of Legal, Sezzle
Product
$175-250k
Buy now, pay later solution platform
Job no longer available
Buy now, pay later solution platform
201-500 employees
Job no longer available
$175-250k
201-500 employees
Company mission
To empower the next generation with interest-free instalment plans that enhance purchasing power online and in-store.
Role
Who you are
- 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
- 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
- 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 the job involves
- 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
- 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
Our take
More and more people are looking to "Buy Now Pay Later" (BNPL) solutions to increase their purchasing power. Sezzle is one of a raft of companies offering interest-free payments solutions.
Sezzle was launched with the intention of giving ordinary people more financial agency. The platform offers consumers rapid approval decisions, and loans do not affect their credit score. What's more, users can opt-in to an innovative credit building service. Sezzle has further consolidated its market position by partnering with other companies, including customer service platform Klaviyo.
The prevalence of BNPL solutions has increased hugely in recent years, and Sezzle's main challenge will be competing with rival providers, including Klarna and PayPal. Post IPO, Sezzle experienced a market contraction in 2025 after questions were raised over its business model's sustainability, so it'll be interesting to see how the company responds and continues its growth.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Company
Funding (last 2 of 4 rounds)
Apr 2019
$5.7m
EARLY VC
Nov 2018
$100m
LATE VC
Total funding: $116.7m
Company benefits
- Comprehensive Benefit Plans
- Generous Parental & Family Leave
- Competitive 401k Match
- Paid Time Off & Volunteer Time Off
- Ownership Through Equity
- 100% of Donations to Charity Matched
- Remote Friendly Company
- Highly Discounted Fitness Membership
Company HQ
Downtown West, Minneapolis, MN
Leadership
Charlie Youakim
(CEO)Prior to Sezzle, Charlie founded Passport where he served as the co-CEO for nearly 6 years.
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