Director, Financial Systems & Transformation

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 the Financial Systems & Transformation function over time — defining scope, identifying capability gaps, and bringing in talent as the function evolves • Serve as the Finance function’s primary technical voice in cross-functional forums — partnering with Engineering, Product, Data, and AI Central on decisions that affect financial data, systems, and processes • Champion AI and systems adoption across the Finance team — providing training, tooling guidance, and hands-on support to help Finance professionals get the most out of available tools What We're Looking For Required • 10+ years of experience in financial systems, accounting technology, or a closely related field — with meaningful time spent in a high-growth or scaling environment • Deep ERP expertise — ideally including implementation experience (go-live, integration design, configuration, and post-live optimization) with platforms such as NetSuite, Campfire, Sage Intacct, or equivalent • Strong finance and accounting foundation — sufficient understanding of US GAAP, month-end close processes, and financial reporting to both translate business requirements into systems design and identify where process redesign itself is the better answer, without losing fidelity • Demonstrated experience building or owning IT General Controls and access control frameworks — SOD enforcement, user provisioning, change management, and audit-trail documentation • Strong grasp of financial master data design and governance — chart of accounts structure, dimension/segment design, and the data architecture decisions that determine downstream reporting flexibility • Demonstrated ability to design or re-engineer core accounting processes (close, AP, payroll, or similar) around best practices — not just automate existing process but rethink it • Experience working directly with external auditors (Big 4 preferred) on IT controls testing and audit evidence standards • Hands-on experience with API integrations and data pipeline design — comfort working with Engineering teams to scope and spec integration work • Genuine enthusiasm for AI and automation — you think naturally about where agent-based workflows can replace manual processes, and you’re excited to build them • Exceptional communication skills — ability to translate between finance, engineering, and executive audiences without oversimplifying or losing technical precision • Comfort building and scaling in a fast-paced, resource-constrained environment — this is very much a “build the plane while flying it” role, and success will depend on strong prioritization instincts and the ability to move quickly as priorities shift Strongly Preferred • Experience with Campfire or another AI-native ERP platform — distinct from legacy systems, these environments call for a different way of thinking about configuration and workflow design • Experience designing or operating AI-automated workflows in a finance or accounting context — intelligent document processing, transaction coding automation, or similar • SOX compliance experience, including ITGC documentation, RCM design, and internal or external audit support — ideally in a pre-IPO or newly public company • Experience with close management platforms (FloQast, BlackLine, or equivalent) and financial reporting automation tooling • Prior experience at a fintech, payments company, or similarly regulated financial services environment • CPA or equivalent credential is a plus, not a requirement • Formal project management experience or training — this role requires running complex, cross-functional projects to completion, not just providing technical and functional expertise • Experience leading close process optimization or standardization initiatives, ideally reducing close timelines or manual touch-points • Familiarity with payroll and AP operational best practices — vendor management, payment controls, exception handling — beyond the systems that support them Compensation Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) and Tier 3 (Salt Lake City) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location. Tier 1 (NYC/Bay Area) $180,000—$225,000 USD Tier 3 (Salt Lake City) $150,000—$190,000 USD 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