The Director of Underwriting leads the underwriting team, assesses business creditworthiness, mentors team members, and develops underwriting policies aligned with company goals.
Flex is building the AI-native private bank for business owners.
We’re re-architecting the entire financial system for entrepreneurs—from the first dollar a business earns to how that value compounds, moves, and is ultimately spent in real life. Banking, credit, payments, personal finance, and financial operations—rebuilt from the ground up as a single, intelligent system. Flex is the full financial home for ambitious owners.
Since launching publicly in September 2023, Flex has scaled from zero to nine-figure annualized revenue, with a clear path to profitability by late 2026. We move fast, ship relentlessly, and operate with extreme ownership.
Our customers are affluent business owners ($3–$200M in revenue)—the backbone of the economy and one of the most underserved segments in finance. They’re stuck with outdated banks and fragmented tools. We’re replacing all of it. The opportunity is massive: a ~$1T+ revenue market hiding in plain sight. Our ambition is to build a $100B+ company by delivering a product that is fundamentally better—not incrementally improved.
Flex has raised $100M+ in equity and $300M+ in debt.
- Mission-critical problems: We build software that directly controls how money moves at scale.
- High bar, low ego: Small teams, exceptional people, real ownership.
- Speed over comfort: We prioritize execution, quality, clarity, and results.
- Enduring impact: What we’re building will define how a generation of owners runs their businesses.
Team & Locations
We hire exceptional people who want to build hard things and see their work matter immediately. Roles are available in: San Francisco, Miami, New York, and fully remote.
Flex Fuels Ambition.
The Director of Underwriting at Flex is a dynamic owner/operator role, where you will not only lead the underwriting team but also directly engage in underwriting activities. This position requires you to assess the creditworthiness of businesses using customer-supplied financial documents and third-party data, ensuring decisions align with Flex’s strategic objectives. You will also be active in reviewing and enhancing the work of other underwriters, providing guidance to foster their professional growth and improve overall team performance in terms of decision quality as well as process efficiency. Reports to the Chief Risk Officer.
Key Responsibilities
- Directly underwrite applications to assess business creditworthiness, employing both customer financial documents and third-party data such as commercial credit bureau reports.
- Actively review and validate underwriting decisions made by team members, supplying constructive feedback and coaching to enhance their skills and decision-making capabilities.
- Employ sophisticated methodologies to identify credit risks and prevent fraud, mitigating potential challenges within the underwriting process.
- Develop and refine underwriting policies that align with Flex’s strategic goals and maintain low default probabilities.
- Mentor and lead the underwriting team, fostering an environment of continuous learning, innovation, and accountability.
- Collaborate with cross-functional teams to streamline underwriting processes and contribute to achieving Flex’s business objectives.
- Collaborate with other parts of the Risk org (Portfolio Management, Analytics, Strategy development) to create an efficient lifecycle view of the Credit Portfolio that leads to maximization of customer lifetime value within and across products.
Requirements
- A minimum of 10 years of relevant experience, including 5+ years in a management role with hands-on underwriting responsibilities. Experience in the Fintech space a strong plus.
- Expertise in financial analysis and credit underwriting principles, with the ability to translate complex data into strategic decisions.
- Proven experience in actively underwriting and guiding underwriters through complex credit scenarios.
- Strong leadership skills with the ability to balance strategic oversight with direct operational involvement
Why Join Us
Build something generational — Capture the full lifecycle of money for ambitious business owners.
Work on real money, real risk — Payments, credit, and banking at serious scale.
Solve hard problems — AI, underwriting, compliance, and global finance from first principles.
True ownership — Small teams, high trust, real accountability.
Founder-level exposure — Direct access to leadership, customers, and investors.
High bar, high taste — Move fast without cutting corners.
Elite peers — People here are builders, not tourists.
Real upside — Meaningful equity if you help build something big.
Top Skills
Credit Underwriting
Financial Analysis
Risk Assessment
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