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Senior Director, Billing & Client Invoicing

Job in Schaumburg, Cook County, Illinois, 60159, USA
Listing for: Wheels, LLC
Full Time position
Listed on 2026-09-13
Job specializations:
  • Accounting
    Accounts Receivable/ Collections, Accounting & Finance, Financial Compliance, Accounting Manager
Salary/Wage Range or Industry Benchmark: 157000 - 220000 USD Yearly USD 157000.00 220000.00 YEAR
Job Description & How to Apply Below

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.

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
    • 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.
  • 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.
    • 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
    • Supporting broader finance transformation…
Position Requirements
10+ Years work experience
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