Senior Director, Billing & Client Invoicing

Senior Director, Billing & Client Invoicing

We are seeking an experienced and highly disciplined Senior Director to lead the Billing & Client Invoicing function within our fleet leasing and services business.

• 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 intake, prioritization, sequencing, and delivery of invoice customization requests, aligning implementation timelines with contractual scope, client readiness, and financial objectives.
• Establish and enforce 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.
• Partner with Sales, Client Management, Client Services, and Client Onboarding to onboard new clients with complex invoicing needs.
• 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.
• Leverage systems, automation, and data controls to reduce manual effort, improve billing accuracy, and support scalable growth.
• Serve as the enterprise decision authority for billing standards and 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 as a key liaison for billing‑related client escalations.
• Support broader finance transformation and process improvement initiatives.
• Motivate a high‑performing billing team with strong ownership and accountability.

• Excellent communication skills.
• Strong team management abilities.
• Leadership experience in high‑volume, complex billing environments.
• Knowledge of contract‑based, multi‑service invoicing (leasing, usage‑based, or subscription models).
• Understanding of billing systems, ERP platforms, and data structures.
• Ability to design and implement scalable processes.
• High attention to detail with strong analytical and problem‑solving skills.

• 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.
• Strong understanding of billing systems, ERP platforms, and data structures.
• Demonstrated ability to design and implement scalable processes.

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.

$157,100–$219,900 (base salary). Eligible for annual incentive plan based on company and individual performance.