General Counsel at Sezzle

United States

Job Description: Chief Financial Officer About the Role: Sezzle (NASDAQ: SEZL) seeks a transformational CFO to lead its next phase of growth. We envision this person being a strategic financial leader who can successfully scale our dynamic FinTech from a current run rate of $400M in revenue and $120m in net income to $5B+ in revenue and $1B+ in net income, while delivering exceptional shareholder value creation. The role requires a rare combination of capital markets expertise, public company leadership, and entrepreneurial execution. With $271M in 2024 revenue (up 70% YoY), proven profitability, and a $2.3B market cap, Sezzle offers an extraordinary opportunity to build upon a winning foundation and make an enduring impact on the future of fintech. The opportunity at Sezzle: Sezzle stands at an inflection point - ready to scale from a breakout fintech to a fintech leader for the next generation of U.S. consumers. In 2024, the Company achieved record profitability of $80.4M net income and delivered a 900%+ stock price return, demonstrating the powerful economics of our differentiated BNPL model. The incoming CFO will inherit a strong foundation: a profitable business model, a stable finance team and corporate structure, millions of loyal consumers, proven unit economics, and the ability to co-design the path to $1B+ revenue. This is a CEO partnership role requiring someone who operates as a true strategic co-pilot. The CFO will work directly with founder and CEO Charlie Youakim, who previously built Passport Parking into a national leader and has guided Sezzle from a startup to a scaled public company. The ideal candidate brings the intellectual firepower to navigate complex capital markets while possessing the emotional intelligence to lead teams, build relationships with their team, the company and its leadership, board members, strategic partners, and investors. Mission and culture context: The company culture emphasizes MEI; Merit, Excellence, and Intelligence, with a results-driven environment that rewards and values talent over tenure and values calculated risk-taking. Position Details: Title: Chief Financial Officer Reports To: Chief Executive Officer and Chairman, Charlie Youakim Board Interaction: Direct engagement with Board of Directors / Committees Location: Virtual Direct Reports: VP Finance, Controller, FP&A, Treasury, Investor Relations Core responsibilities Strategic financial leadership The CFO serves as the primary architect of Sezzle's financial strategy, translating business objectives into actionable financial plans. This includes developing long-range financial models supporting growth from $270M to $1B+ in revenue, optimizing capital allocation across organic growth, M&A opportunities, and shareholder returns, and establishing financial guardrails that balance aggressive growth with profitability discipline. The role requires building Sezzle's financial narrative for investors, articulating the path of achievement and sustainable competitive advantage. Capital markets and investor relations As the public face of Sezzle's financial story, the CFO leads all investor-facing activities including quarterly earnings calls, investor conferences, and one-on-one institutional meetings. Critical deliverables include crafting compelling equity narratives that communicate Sezzle's differentiated value proposition, managing sell-side analyst relationships and consensus expectations, evaluating and executing capital raising strategies across debt and equity markets, and overseeing the company's $50M share repurchase program with disciplined intrinsic value hurdles. Risk management and regulatory navigation The BNPL industry operates in an evolving regulatory environment requiring sophisticated risk management. The CFO oversees credit risk frameworks and loss provisioning models, increasingly powered by machine learning algorithms that assess creditworthiness and predict default probability. Critical responsibilities include evaluating AI/ML investments in underwriting and fraud detection, ensuring compliance with state-level BNPL regulations and potential federal requirements, managing enterprise risk including cybersecurity, operational, and reputational risks, and maintaining relationships with banking partners (including the exclusive WebBank partnership). The CFO must understand how AI/ML-driven decisioning impacts unit economics, regulatory risk, and competitive positioning. Operational excellence and infrastructure Scaling from $270M to $1B requires world-class financial infrastructure. The CFO builds and leads a high-performance finance organization, implements systems and processes supporting public company requirements (SOX compliance, SEC reporting), drives AI/ automation and efficiency across financial operations, and ensures accurate, timely financial reporting with robust internal controls. Board governance and stakeholder management The CFO serves as a trusted partner to the Board of Directors and Audit Committee, preparing board materials that provide strategic insight beyond basic financials, ensuring governance best practices and transparent communication, and building relationships with key institutional investors and research analysts. Required qualifications: Professional background The ideal candidate brings 15+ years of progressive finance leadership experience with a career trajectory that includes investment banking at a bulge bracket or leading middle-market firm, operational CFO or senior finance leadership at a high-growth FinTech or financial services company, and demonstrated success scaling revenue from $250M to $1B or beyond. Specific experience requirements: Public company mastery: Minimum 5 years as CFO or senior finance executive at a publicly traded company with full ownership of SEC reporting, investor relations, and SOX compliance Capital markets expertise: Led or co-led successful capital raises exceeding $500M across debt and equity instruments; IPO experience strongly preferred M&A transaction experience: Evaluated and executed strategic acquisitions; experience with deal structuring, due diligence, and integration FinTech or financial services depth: Understanding of lending economics, payment processing, credit risk management, and financial services regulatory environment AI/ML strategic fluency: Executive-level understanding of artificial intelligence and machine learning applications in credit decisioning, fraud detection, predictive analytics, and financial forecasting; ability to evaluate AI/ML investments and articulate their impact on unit economics and competitive positioning High-growth scaling: Track record building finance teams from 15 to 50+ professionals while implementing scalable systems and processes Educational credentials MBA from a top-tier program preferred CPA, CMA, or CFA certification valued Undergraduate degree in Finance, Accounting, Economics, or related field Demonstrable outstanding academic GPA (must top 5%, preferred top 2%) Competency profile Critical competencies (must-have) Strategic Financial Acumen: Ability to develop sophisticated financial models, evaluate complex business scenarios, and translate strategic vision into executable financial plans. Deep understanding of Sezzle’s unit economics and market economics such as LTV/CAC, take rates, contribution margins and how operational decisions impact shareholder value. Capital Markets Fluency: Expert navigating public equity and debt markets, including institutional investor psychology, analyst relationships, and optimal timing of capital transactions. Ability to craft compelling financial narratives that differentiate Sezzle's story in a competitive investor landscape. Risk Intelligence: Sophisticated approach to managing credit risk, regulatory risk, and operational risk in a rapidly evolving environment. Ability to balance growth ambitions with prudent risk management. AI/ML and Technology Acumen: Executive-level understanding of how artificial intelligence and machine learning drive competitive advantage in FinTech—from credit underwriting algorithms to fraud detection systems. Ability to evaluate technology investments, understand their P&L impact, and communicate AI/ML capabilities to investors as key value drivers. Comfortable partnering with technical leadership to leverage data science for financial optimization. Operational Discipline: Proven ability to build world-class finance organizations, implement robust internal controls, and drive operational efficiency at scale. Track record of successfully navigating audit processes and regulatory examinations. Leadership competencies (IQ + EQ balance) CEO Partnership: Ability to serve as a true thought partner to the CEO, bringing independent perspective while maintaining alignment on strategic direction. Comfortable providing candid counsel and respectful challenge. Board Effectiveness: Skilled at preparing and presenting board materials that drive strategic discussion. Ability to build trust with directors and navigate complex governance situations. Team Leadership: Track record of attracting, developing, and retaining top finance talent. Ability to build high-performance culture while demonstrating genuine care for team members. External Presence: Excellent communication skills with ability to represent Sezzle credibly to investors, analysts, banking partners, and media. Comfortable in high-stakes presentations and negotiations. Integrity and Ethics: Unquestionable integrity with commitment to transparency and ethical conduct. Ability to navigate complex situations where business pressures and ethical considerations may conflict. Success metrics First 90 days Complete comprehensive assessment of financial operations, systems, and team capabilities Build trusted working relationships with CEO, board members, and executive team Establish baseline understanding of unit economics and key value drivers Identify quick wins and develop prioritized improvement roadmap First 12 months Deliver accurate financial forecasts within 5% variance to actuals Execute on capital allocation strategy supporting growth and shareholder returns Strengthen investor relationships evidenced by improved analyst coverage and institutional ownership Complete critical systems or process improvements identified in initial assessment Build or upgrade finance team capabilities as needed Multi-year objectives Support revenue growth trajectory toward $1B milestone Achieve and maintain Rule of 40 performance (revenue growth % + EBITDA margin % ≥ 40%) Drive meaningful stock price appreciation through operational excellence and effective investor communication Position Sezzle as a best-in-class public company from a finance and governance perspective