Head of Licensing & Exam Management

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?

About the role

Flex's ability to operate in every market we serve depends on maintaining a growing portfolio of state licenses, spanning consumer lending (servicing), loan brokering, and money transmission, and consistently demonstrating to regulators and bank partners that our oversight is precise, proactive, and scalable.

We are seeking a Director, Head of License & Exam Management to own this pillar end-to-end. This is not a maintenance role. Flex's LEM function is early in its maturity journey, and this leader will be responsible for architecting the frameworks, systems, and team operating model that take it from a largely manual, reactive posture to a mature, automated, and exam-ready program.

You will design and execute Flex's licensing strategy across all three entity types, build the infrastructure to manage a license portfolio that is growing in both volume and complexity, and ensure Flex is always prepared for state exams, audits, and bank partner reviews. You will partner closely with Legal, Product, Operations, Finance, and our bank partners to embed licensing and exam readiness into the way Flex operates, not bolt it on after the fact.

This role reports to the Chief Compliance Officer and is a critical leadership position within the Compliance organization.

What you’ll do

License Strategy & Operations

• Own Flex's multi-state licensing strategy across servicing, brokering, and money transmitter licenses, including acquisition, renewals, amendments, and surrenders.
• Design and maintain a comprehensive license matrix that maps licensing requirements to Flex's products, entities, and jurisdictions — ensuring the company always knows where it has the right to operate and where gaps exist.
• Build scalable workflows for license applications, renewals, and regulatory filings, leveraging licensing management platforms (e.g., Brico/NMLS integration) to automate deadline tracking, document management, and submission processes.
• Monitor regulatory changes at the state and federal level that affect licensing requirements, and translate those changes into actionable updates to internal policies, processes, and filings.
• Establish and own the escalation process for at-risk licenses, including remediation plans, stakeholder communication, and regulator engagement.
• Partner with Legal to evaluate licensing implications of new products, features, and market expansions — ensuring licensing readiness is embedded into product roadmaps and go-to-market planning.

Exam & Audit Management

• Architect Flex's exam readiness framework, ensuring the company is continuously prepared for state regulatory exams, bank partner audits, and ad hoc regulatory inquiries.
• Lead exam execution end-to-end: scoping, stakeholder preparation, evidence collection, regulator meeting facilitation, data request tracking, and real-time internal reporting.
• Build and maintain a centralized repository of exam artifacts, response libraries, and institutional knowledge that accelerates preparation and improves response quality over time.
• Own post-exam processes including root cause analysis of findings, corrective action tracking, lessons learned documentation, and procedure updates.
• Develop pre-exam preparation programs — including mock exams and stakeholder readiness sessions — that strengthen Flex's posture and reduce risk of surprise findings.

Regulatory Relationships & Cross-Functional Partnership

• Serve as a primary point of contact with state regulators on licensing and exam matters, building constructive relationships that support proactive issue resolution and reinforce Flex's credibility.
• Partner with Legal, Product, Operations, Finance, and Business Development to ensure licensing obligations and exam expectations are understood and embedded across the business.
• Represent the LEM function in internal governance forums, bank partner meetings, and senior leadership updates — translating licensing and exam posture into clear, decision-relevant insights.
• Generate compliance reporting on license health, exam readiness, and regulatory engagement — including dashboards, KPIs, and executive summaries that provide real-time visibility into the pillar's performance.

Leadership & Program Maturity

• Define and execute a maturity roadmap that moves Flex's LEM function from ad hoc to mature across license management, exam management, change management, and reporting.
• Implement AI-enabled workflows and automation to increase the speed, accuracy, and auditability of licensing and exam processes — with appropriate human-in-the-loop governance.
• Lead, mentor, and develop team members, establishing clear performance expectations, creating career development paths, and building a bench of future compliance leaders.
• Set the operating rhythm for the LEM team — including prioritization frameworks, SLA-based workflows, and reporting cadences that ensure disciplined execution without bottlenecks.

Who You Are

• 10+ years of experience in licensing, exam management, or compliance operations at a fintech, bank, or regulated financial services provider, with progressively expanding scope and ownership.
• Direct experience managing multi-state licensing portfolios, including consumer lending, loan brokering, and/or money transmitter licenses.
• Proven track record of leading regulatory exam cycles end-to-end — preparation, execution, and remediation — with state regulators and/or bank partners.
• Deep knowledge of state licensing frameworks, NMLS processes, and the regulatory landscape governing consumer lending, payments, and money transmission.
• Experience building or significantly maturing a licensing or exam management function — moving it from reactive and manual to proactive and scalable.
• Demonstrated ability to partner cross-functionally with Legal, Product, and Operations teams, translating regulatory obligations into operational guardrails that enable business velocity.
• Comfort with compliance technology and automation — experience implementing or governing licensing platforms, workflow automation, or AI-enabled compliance tools.
• Strong communicator who can represent Flex credibly with state regulators and translate complex licensing and exam dynamics into clear guidance for internal stakeholders.
• Organized, precise, and reliable — someone who instills confidence through the quality and consistency of their work.
• Experience with Brico, NMLS Consumer Access, or similar licensing management platforms.
• Familiarity with fintech–bank partnership models and the licensing implications of bank-sponsored lending or payments programs.
• Experience building exam response libraries, regulatory contact trackers, or evidence automation systems.
• Background in scaling compliance programs in a growth-stage or venture-backed environment.
• Bachelor's degree required; JD or advanced degree a plus.

Life at Flex

We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.

Offices

Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.

Benefits

For full-time U.S. employees we offer:

• Competitive medical, dental, and vision
• Company equity
• 401(k) plan with company match 
• Unlimited paid time off + 13 company paid holidays
• Parental leave 
• Free Flex subscription

 For full-time non-U.S. employees, we offer:

• Competitive compensation + company equity
• Unlimited PTO