Job Overview

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.

Key Responsibilities - Essential Functions

Leadership & Team Management

• 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.

Billing Operations

• 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.

Invoice Design, Technology & Governance

• 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.

Controls & Compliance

• 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.

Cross-Functional Collaboration

• Work closely with Finance, Operations, Sales, and Client Services.
• Act as a key liaison for billing-related client escalations.

Education and Experience

• 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).

Job Specifications, Physical Demands and Work Environment

This position is in Schaumburg, Ill or Alpharetta, GA and operates in a professional office environment. This is a full-time position, Monday through Friday, works onsite 3 days a week. Travel is expected for this position as needed.