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Senior Director, Billing & Client Invoicing

Wheels

Schaumburg, Illinois

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JOB DETAILS
SKILLS
Accounting, Accounts Receivable, Automation, Automotive Repair and Maintenance, Billing, Business Support, Cash Applications, Change Management, Coaching, Communication Skills, Continuous Improvement, Cross-Functional, Customer Escalations, Customer Experience, Customer Support/Service, Documentation Standards, Electronic Data Interchange (EDI), Establish Priorities, Finance, Financial Operations, Leadership, Onboarding, Order to Cash, Partner Sales, Performance Metrics, Process Improvement, Product Design, Reconciliation, Rentals, Revenue Recognition, Risk Analysis, Sales, Sales Management, Team Lead/Manager, Time Management
LOCATION
Schaumburg, Illinois
POSTED
24 days ago
Job Description:

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
    • 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.
  • 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
    • Support broader finance transformation and process improvement initiatives

Leadership Responsibilities Strategy
  • Motivate a high-performing billing team with strong ownership and accountability

COMPETENCIES - SKILLS
  • Excellent communication skills
  • Team Management skills

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)
  • Stron

About the Company

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Wheels

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