Associate Director, Compliance Issue 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?

The Role

We are looking for an Associate Director, Compliance Issue Management to own how Flex identifies, resolves, and reports on compliance issues across the business. This is not a back-office reporting role. It is a cross-functional leadership role: you are accountable for driving compliance issues from identification through resolution and reporting, partnering directly with senior leaders across Product, Engineering, Risk, and Legal, and with the C-suite, to ensure the right problems are resolved on time.

Internally, you will own Flex's compliance issues and problem-management program end to end. You will run the cross-functional working group that triages and prioritizes issues, set and enforce the standards for how issues are documented and remediated, and project-manage resolution across teams that do not report to you. Many issues span multiple functions and require multiple milestone owners; you will hold each of them accountable and escalate to executive sponsors, including the Chief Product Officer, Chief Risk Officer, and Chief Technology Officer, when timelines slip. Externally, you will own recurring reporting to Flex's bank partners. Across both, you will design AI-enabled workflows that scale the work without sacrificing accuracy, audit-ability, or regulatory defensibility.

This role is right for someone who has owned issues management or regulatory reporting at a mature, regulated institution and has also fixed or built something from an initial baseline at a high-growth fintech. Someone who can engage credibly with C-suite executives, drive accountability across functions through influence rather than authority, and is comfortable with ambiguity and confident in their judgment. Someone ready to be handed a program and mature it.

What You'll Do

• Own Flex's compliance issues and problem-management program end to end: identification, triage and risk-tiering, remediation, validation, and closure of compliance issues and findings across the business.
• Drive issues to resolution across functions, project-managing remediation across Product, Engineering, Risk, Legal, and Security teams that do not report to you, and holding multiple milestone owners accountable to committed dates.
• Engage and influence senior leaders, including executive sponsors at the C-suite level (Chief Product Officer, General Managers, Chief Technology Officer), to ensure timely identification, resolution, and reporting of issues across the product lifecycle.
• Run the cross-functional compliance issues working group: set the agenda, drive decisions on prioritization and escalation, and ensure follow-through.
• Set and enforce the standards for how issues are documented, prioritized, and resolved, including SLA discipline, escalation paths, and a clear standard for what qualifies as closed.
• Drive root-cause analysis and corrective action: partner with issue owners to define remediation plans, hold target dates, and verify that fixes hold over time.
• Own the reporting that gives leadership real-time, decision-relevant visibility into open issues, aging, ownership, and remediation status, rather than backward-looking status decks.
• Own the full partner bank reporting program: monthly, quarterly, annual, and exam-driven deliverables. Ensure every report is accurate, on time, and defensible.
• Serve as the primary point of contact for partner bank inquiries, including due diligence questionnaire, ad hoc data requests, and regulatory exam support. Own the response process from intake to delivery, including full scoping of the requests. 
• Design and own AI-enabled workflows for high-volume, repeatable reporting and issue-management tasks (data assembly, first-draft generation, aging and SLA monitoring), with clear auditability and human-in-the-loop checkpoints on consequential calls.
• Build signal-driven monitoring that surfaces overdue issues, SLA breaches, and reporting gaps in real time, rather than relying on manual review cycles.
• Serve as the authoritative voice on compliance issues and reporting in internal reviews, audits, and regulatory or bank partner examinations.
• Proactively identify gaps in reporting coverage, data quality, and issue-management controls, and close them before they become findings.

What We're Looking For

• 8+ years of experience in compliance, risk, audit, regulatory reporting, or a closely related discipline.
• Experience at both a large, regulated institution with a mature compliance function and a high-growth, venture-backed fintech or technology company.
• Demonstrated track record owning an issues-management or regulatory-reporting program: standing one up, fixing a broken one, or maturing it to the next level.
• Proven ability to drive outcomes across functions through influence rather than authority, including holding senior stakeholders accountable to their commitments.
• Executive presence: able to engage, challenge, and align C-suite leaders, and to translate complex detail into clear recommendations for executive and bank partner audiences.
• Strong project management instincts: comfortable owning many moving parts across multiple teams and driving them to closure against a deadline.
• Demonstrated ability to make and defend judgment calls under ambiguity, including explicit speed-versus-rigor tradeoffs.
• Experience designing AI-enabled workflows for compliance, risk, or reporting use cases, with a clear point of view on where automation helps and where human oversight is non-negotiable.
• Comfort with data; SQL experience, or the ability to query and analyze data independently, is a strong plus.
• Experience supporting regulatory exams, audits, or bank partner oversight in a financial services or fintech environment.

Nice to Have

• Experience building or rebuilding a compliance issues-management or reporting program from a weak baseline.
• Familiarity with GRC platforms and common compliance or reporting tooling.
• A track record of producing recurring reporting for bank partners or regulators.
• Working knowledge of consumer lending or payments regulatory frameworks.

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