Director Ledger Reconciliation Systems

ImagineX is a tech company that deploys AI-assisted teams to build and secure mission-critical enterprise solutions with our clients – spanning software, data, and AI. Structured like a software company, not a traditional consultancy, we blend deep technical expertise with authentic values, achieving world-class satisfaction (NPS 91). Our dedicated teams specialize in software, data, and AI across the U.S. and LATAM, bridging the gap between boutique agility and enterprise scale.

We are seeking a Director of Ledger Reconciliation & Money Movement to take ownership of a complex, business‑critical financial system that sits at the intersection of accounting, payments, and engineering. This is not a traditional finance role — it requires someone who understands how money actually moves through a technical system, where it breaks, and how to architect a long‑term fix.

The core challenge: payouts are currently calculated post‑capture instead of post‑settlement. While customer‑favorable, this creates significant internal reconciliation complexity. The system is heavily dependent on tribal knowledge, lacks documentation, and needs a leader who can bring clarity, structure, and a sustainable architectural path forward.

This director will serve as the connective tissue between Finance and Engineering — translating requirements, defining the product direction for reconciliation systems, and driving toward a durable, well‑engineered solution.  This is a 100% remote full-time opportunity. 

Key Responsibilities

• Own the end‑to‑end reconciliation and money movement domain, including ledgering logic, payout flows, and exception handling.
• Deeply understand how funds move through the current system — where data originates, how it transforms, where it breaks, and why.
• Document an existing, tribal‑knowledge‑heavy system and turn it into a clear, maintainable, auditable operational model.
• Lead the architectural direction for a long‑term fix to the post‑capture payout calculation issue, ensuring alignment with both Finance and Engineering.
• Partner with engineering teams to design and implement scalable, accurate, and resilient reconciliation and ledgering systems.
• Serve as the primary translator between Finance and Engineering — ensuring both sides understand requirements, constraints, and impacts.
• Define product requirements, roadmap, and success metrics for reconciliation and money movement systems.
• Identify root causes of reconciliation discrepancies and drive cross‑functional resolution.
• Build processes, controls, and reporting frameworks that improve accuracy, transparency, and audit readiness.
• Provide leadership, clarity, and direction in a domain where ambiguity and complexity are currently high.

Required Experience & Skills

• Director‑level experience in financial systems, payments technology, or a related domain.
• Strong accounting and financial background — able to understand ledgers, settlement flows, and reconciliation logic.
• Deep understanding of how money moves through technical systems (capture → settlement → payout → ledgering).
• Experience designing or owning financial or payment system architecture.
• Ability to diagnose system-level issues, identify failure points, and guide engineering toward sustainable fixes.
• Exceptional communication skills — able to speak credibly with both Finance and Engineering and translate between them.
• Experience leading cross‑functional initiatives with high ambiguity and high business impact.
• Strong documentation discipline and the ability to turn tribal knowledge into structured, repeatable processes.

Nice-to-Have Skills

• Experience with payout systems, settlement engines, or payment processors.
• Background in building or modernizing ledgering systems.
• Familiarity with financial compliance, audit requirements, or SOX‑related controls.
• Product management experience in financial or payments platforms.

Who Thrives Here

• Leaders who can bring order to complexity and build clarity where none exists.
• Systems thinkers who understand both the financial logic and the technical architecture behind money movement.
• Communicators who can bridge Finance and Engineering without losing nuance.
• Builders who want to own a critical domain and drive it toward a long‑term, well‑engineered solution.