Director, Assistant Controller

Summary

Join Flywire as a Director, Assistant Controller and play a pivotal role in enhancing cash reconciliation processes, implementing automation solutions, and strengthening our control environment. You will oversee global cash reconciliation across 200+ bank accounts, drive improvements in accuracy and speed, and maintain sub-ledgers. Lead the evaluation and implementation of automation tools, partner with Product and Engineering teams, and ensure accurate regulatory reporting. Develop a high-performing team, fostering a culture of innovation and continuous improvement. This is not a pure accounting role; it requires strong operational accounting understanding, systems knowledge, and the ability to translate operational needs into scalable technology solutions. The ideal candidate will have deep expertise in high-volume, multi-currency cash operations and proven hands-on experience with reconciliation and automation tools.

Requirements

• Bachelor’s degree in Finance, Accounting, or related field; ACCA, CPA, or equivalent preferred
• 7+ years in high-volume cash operations, reconciliation, or treasury environments, ideally in fintech, payments, or financial services
• Proven hands-on experience with reconciliation automation tools (e.g. BlackLine, WorkDay, Oracle/NetSuite or other tools)
• Demonstrated success partnering with Product/Engineering teams to identify operational improvements
• Deep understanding of global cash reconciliation, payment flows, and multi-currency operations
• Strong analytical and problem-solving skills with a data-driven approach
• Excellent communication skills with the ability to bridge operational and technical stakeholders

Responsibilities

• Oversee daily, weekly, and monthly global cash reconciliation across 200+ bank accounts and multiple products/solutions
• Drive improvements in accuracy, speed, and scalability of reconciliation processes, leveraging automation and AI where possible
• Maintain and reconcile sub-ledgers to clearly identify client vs. corporate cash
• Lead the evaluation, selection, and implementation of cash reconciliation automation tools and other technology solutions
• Partner with Product and Engineering to improve data integrity in core platforms, ensuring reconciliation needs are embedded into system design
• Act as the operational “translator” between reconciliation teams and technical teams, ensuring requirements are clearly understood and delivered
• Ensure accurate and timely reporting of cash balances and liabilities to regulators (FCA, MTL, MAS, BOL, etc)
• Oversee segregation, reconciliation, and reporting of client and corporate funds
• Support quarterly call reports, regulatory examinations, and global/local audits
• Lead and develop a high-performing reconciliation and reporting team, fostering a culture of accountability, innovation, and continuous improvement
• Coach the team to adopt automation and process optimisation best practices

Benefits

• Competitive compensation, including Restricted Stock Units
• Employee Stock Purchase Plan (ESPP)
• Flying Start - Our immersive Global Induction Program
• Wellbeing Programs (Mental Health, Wellness) with Global FlyMates
• Competitive time off including FlyBetter Days to volunteer in a cause you believe in and Digital Disconnect Days!
• Great Talent & Development Programs