Director, Financial Systems & Transformation

About this role

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

We are seeking a strategic leader who pairs deep systems expertise with strong process design instincts to build and own Flex's Financial Systems & Transformation function from the ground up. This is a rare opportunity to define a new pillar within the Finance organization at a fast-scaling fintech — one where the scope extends well beyond traditional ERP administration into agentic AI infrastructure, process automation, and the controls architecture that will underpin Flex’s next phase of growth.

As Director, Financial Systems & Transformation, you will own the internal financial systems that power Flex’s accounting and financial reporting function — including our core ERP, procure-to-pay (P2P), T&E systems, and additional financial reporting tooling as the function matures. You will also design, build, and maintain the AI-powered workflows that are central to Flex’s vision for a modern, scalable Finance function, and you will lead the build-out of ITGC and financial systems controls that keep pace with the business as it scales.

This role sits at the intersection of finance, systems, and AI — and requires a leader who can operate with fluency across all three. You will partner closely with the VP Controller, the broader Finance leadership team, and Flex’s Engineering and AI Central teams to make the vision real. This position will be based in our New York headquarters on a hybrid basis and will report to the VP Controller.

What You'll Do

Financial Systems Ownership & Administration

• Own our ERP (Campfire) as Flex’s financial system of record — including configuration, close module setup, chart of accounts and dimension/segment governance, and ongoing system health

• Own our procure-to-pay (P2P) systems for AP and T&E — evaluating near-term enhancements and long-term tooling strategy as we scale

• Manage integrations between core financial systems and the upstream/downstream data sources that feed them — including the payroll (Rippling) integration in partnership with the People/HRIS systems team — ensuring accurate, timely, and auditable data flows across the Finance stack

• Serve as the internal product owner for financial systems enhancements — translating Finance team requirements into system configuration and working with vendors and technical teams where needed

• Partner with the Strategic Finance team on the evaluation, implementation, and ongoing administration of FP&A tooling, supporting both the Finance and business planning functions

• Evaluate, implement, and administer additional tooling across Finance as the function scales — including financial reporting, SOX, and account reconciliations

Agentic AI Infrastructure

• Design, build, and maintain AI-powered workflows that eliminate manual, high-volume processes across the Finance function — with a particular focus on transaction coding, close automation, and financial reporting

• Own the technical architecture for agent-as-preparer workflows: defining confidence thresholds and exception routing, and building the audit trail infrastructure required in a controls-conscious environment

• Partner with Flex’s AI Central team to extend our internal AI platform into Finance use cases — including inquiry triage, routing, and other templatable workflows

• Proactively identify and prioritize new automation opportunities across the Accounting & Finance function; own the agentic build roadmap in partnership with Finance leadership

• Establish and maintain operational health monitoring for all automated workflows — exception rates, throughput metrics, and escalation paths

ITGC, Access Controls & Controls Readiness

• Own IT General Controls (ITGCs) across all financial systems — user access provisioning and deprovisioning, segregation of duties (SOD) enforcement, change management controls, and periodic access reviews

• Design and maintain the control framework and access architecture for automated/agentic workflows — including permissioning, auditability, and documentation standards for a future SOX-ready environment

• Build out Flex’s broader controls readiness over time — ITGC documentation, control testing support, and GRC tool implementation as the company scales

• Serve as the primary liaison between the Finance function and external auditors on technology-related matters, including audit trail standards and controls evidence for automated workflows

Close Automation & Process Optimization

• Build and maintain real-time close monitoring: dashboards and alerts that give Finance leadership live visibility into close status, open items, and risk flags

• Partner with the VP Controller to systematically accelerate the month-end close cycle — identifying and removing structural bottlenecks through better tooling, automation, and process design

• Support the build-out of automated financial reporting infrastructure — enabling reliable, timely reporting across P&L, balance sheet, cash flow, and operational metrics with minimal manual intervention

• Drive P2P process optimization and efficiency — implementing system-based workflows, reducing processing and cycle time, and continuously improving the AP and T&E experience across Finance and the broader company

Team & Stakeholder Leadership

• Build out and shape t

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