Director, Financial Systems & Transformation

Flex•San Francisco, NY

1d•Hybrid

About The Position

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. 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 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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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
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