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Job Description

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, supporting approximately 2,000 clients and managing 800,000 leased vehicles. Billing is a strategic touchpoint with our clients and requires precision, flexibility, and strong operational leadership.

• 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.
  • Establish and enforce clear standards for invoice scope control, post‑implementation enhancements and change management.
  • Provide functional leadership and governance over billing technology, including EDI, invoice integrations and billing‑related data processes.
• Controls & Compliance
  • Establish and maintain strong internal controls over billing accuracy, revenue recognition and invoice completeness.
  • Ensure billing practices do not negatively impact accounts receivable performance, dispute rates or cash application.
  • Support audit requirements and maintain documentation standards.
  • Monitor and resolve billing discrepancies and client inquiries.
• Cross‑Functional Collaboration
  • Work closely with Finance, Operations, Sales and Client Services.
  • Act as a key liaison for billing‑related client escalations.
  • Support broader finance transformation and process improvement initiatives.

• 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.

• Location: Schaumburg, IL or Alpharetta, GA.
• Full‑time, Monday through Friday, onsite 3 days a week.
• Travel: 20‑25% to either location.
• Physical Demands: Standard office environment; occasional lifting, walking and standing.

• Pay range: $157,100–$219,900 (base salary).
• Eligible for annual incentive plan based on company and individual performance.
• Competitive benefits package (health, dental, vision, 401(k), PTO, etc.).

Wheels is an equal opportunity affirmative action employer and administers all personnel practices without regard to race, color, religion, sex, age, national origin, sexual orientation, gender identity or expression, marital status or domestic partnership status, disability, protected veteran status or military status, genetic information or any other category protected under applicable law. Wheels is a Drug‑Free Workplace. All employment is contingent on successful completion of drug and background screening.

Wheels provides a robust benefits package that is market‑leading and competitive, including health, dental, vision, 401(k) matching, paid time off, wellness programs and more.