Head of Licensing & Exam Management, Flex
$176.8-260k
+ Equity
Expert level
Remote from US
Flexible rent payment application
Be an early applicant
Flexible rent payment application
501-1000 employees
B2BPaymentsRentingFinancial ServicesMobile
Be an early applicant
$176.8-260k
+ Equity
Expert level
Remote from US
501-1000 employees
B2BPaymentsRentingFinancial ServicesMobile
Company mission
To help people pay for the things that matter most.
Role
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
What the job involves
- 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
- 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
Our take
Many people struggle to pay their rent every month, with a variety of bills hitting their bank accounts simultaneously. Whilst many of these people earn enough money to cover their bills, the inflexible nature of monthly bills can make the all-in-one payment a harder obstacle.
Flex provides a mobile application for the flexible payment of rent, allowing users to pay their landlords through flexible payment plans, reschedule payments when necessary, and protect their funds through Overdraft Protection. The company achieves this by partnering with estate agents and paying their resident's bills upfront, taking on the challenges that landlords would normally have due to late payments.
Flex has experienced extremely rapid growth since its founding which has caused some issues, as it struggled to keep up with the surge in new customers. Having made improvements to its product and scaled its customer service team, it is set to continue providing a service that has come to be highly valued by both tenants and landlords.
Freddie
Company Specialist at Welcome to the Jungle
Insights
Top investors
10% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2022
$160m
SERIES C
Apr 2021
$46.6m
SERIES B
Total funding: $225.1m
Company benefits
- Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
- Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
- NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
- 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
- Flex Giving: Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
- Employee Assistance Fund: Confidential financial support to teammates facing unexpected hardships or emergencies.
- Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter.
- Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
- Free Flex Subscription: As a Flex employee, you'll have full access to our services without charge.
- GrubHub Credit: Enjoy meal credits while in the office, so you’re fueled for the workday ahead.
Company HQ
Midtown Manhattan, New York, NY
Leadership
Shragie Lichtenstein
(Co-Founder & CEO)Prior to co-founding Flex in 2019, Shragie co-founded Boundless Reality. They graduated from Yeshiva University in 2015 with a Bachelor's Degree in Finance.
YeTong Shao
(Co-Founder)Prior to co-founding Flex in 2019, YeTong co-founded Boundless Reality alongside Shragie. They graduated from the University of Chicago with a Bachelor's Degree in Mathematic & Economics.
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