Senior Director, Billing & Client Invoicing

Wheels, Inc.•Schaumburg, IL

8d•$157,100 - $219,900•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

Excellent communication skills
Team Management skills

Responsibilities

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 to 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
Support broader finance transformation and process improvement initiatives
Motivate a high-performing billing team with strong ownership and accountability