Senior Director, Billing and Client Invoicing

We are seeking an experienced and highly disciplined Senior Director of Billing & Client Invoicing to lead a critical function within our fleet leasing and services business. This role is responsible for the accurate, timely, and client-tailored billing of a complex, multi-service offering across a large and diverse customer base.

Our business supports approximately 2,000 clients and manages 800,000 leased vehicles, delivering a range of services including maintenance, glass, fuel, telematics, and rental solutions. Billing is a strategic touchpoint with our clients and requires precision, flexibility, and strong operational leadership.

• Lead, coach and develop a multi-layered billing and invoicing organization spanning billing operations, client invoice configuration, dispute resolution and billing enablement functions.
• Establish clear performance expectations, KPIs, and accountability standards
• Foster a culture of accuracy, responsiveness, and continuous improvement

• Oversee the end-to-end billing process, ensuring accuracy, completeness, and timeliness
• Manage high-volume, multi-line invoicing across leasing and ancillary service offerings
• Ensure proper revenue capture and alignment with contractual terms

• Design and deliver customized invoice formats, including EDI and bespoke client-specific layouts, while maintaining standardization, accuracy, and scalability
• Own the end-to-end intake, prioritization, sequencing, and delivery of invoice customization requests, aligning implementation timelines with contractual scope, client readiness, and financial objectives
• Establish and enforce clear standards for invoice scope control, post-implementation enhancements, and change management to prevent uncontrolled complexity, billing delays, and downstream AR impact
• Provide functional leadership and governance over billing technology, including EDI, invoice integrations, and billing-related data processes, ensuring priorities, design decisions, and delivery timelines support enterprise financial goals
• Partner with Sales, Client Management, Client Services, and Client Onboarding to onboard new clients with complex invoicing needs while setting clear expectations around scope, sequencing, and go-live requirements
• Establish enterprise billing standards and controls across upstream operational and product teams whose transactions ultimately flow to client invoices.
• Partner with cross-functional leaders to identify, remediate, and prevent transaction quality issues that drive billing errors, rework, client disputes, and AR delays, even where teams do not formally report into Billing.
• Leverage systems, automation, and data controls reduce manual effort, improve billing accuracy, and support scalable growth without compromising control or client experience.
• Serve as the enterprise decision authority for billing standards, invoice design, ensuring products and services are billing-ready before being scaled.

• Establish and maintain strong internal controls over billing accuracy, revenue recognition and invoice completeness.
• Ensure billing practices, invoice design decisions, and process changes do not negatively impact accounts receivable performance, dispute rates, or cash application, and proactively identify risks to timely cash collection.
• Support audit requirements and maintain documentation standards
• Monitor and resolve billing discrepancies and client inquiries

• Work closely with Finance, Operations, Sales, and Client Services
• Act as a key liaison for billing-related client escalations
• Supporting broader finance transformation and process improvement initiatives
• Motivate a high-performing billing team with strong ownership and accountability

• 10+ years of progressive experience in accounting, finance, billing, revenue operations, or order-to-cash environments
• Proven leadership experience managing teams in high-volume, complex billing environments
• Experience with contract-based, multi-service invoicing (leasing, usage-based, or subscription models preferred)
• Strong understanding of billing systems, ERP platforms, and data structures
• Demonstrated ability to design and implement scalable processes
• High attention to detail with strong analytical and problem-solving skills
• Excellent communication skills, with the ability to interface directly with clients and senior leadership

At Wheels, we believe in fostering a culture that is built on our Core Values and Guiding Principles. We cultivate a culture of excellence and innovation by upholding these values, driving our collective success and growth.

• Integrity – Always act with integrity and honesty.
• One Team – Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference.
• Innovation – Drive continuous improvement, spark…