Senior Director, Billing & Client Invoicing

Wheels, LLC; Schaumburg (IL); On-site; USD 120,000 - 160,000; Full time

Job summary

Wheels, LLC is seeking a Senior Director of Billing & Client Invoicing located in Schaumburg, Illinois. The role requires an experienced leader to manage billing operations for a large fleet leasing business supporting 2,000 clients. Candidates should have over 10 years of experience in finance or billing, with a focus on multi-service invoicing and leadership in complex environments.

This full-time position operates onsite 3 days a week, with some travel expected. A focus on detail, problem-solving, and strong communication skills is essential.

Qualifications

• Proven leadership experience managing billing teams.
• Experience with contract-based and multi-service invoicing.
• Strong understanding of billing systems and data structures.

Responsibilities

• Lead and develop a billing and invoicing organization.
• Oversee the end-to-end billing process for accuracy and timeliness.
• Design customized invoice formats and manage change control.
• Ensure compliance and maintain internal controls over billing.

Skills

Leadership

Communication Skills

Analytical Skills

Problem-Solving

Attention to Detail

Education

10+ years in accounting, finance, or billing

Tools

ERP Platforms

Billing Systems

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 and process improvement initiatives
• Motivate a high-performing billing team with strong ownership and accountability

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)
• 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

Job Specifications, Physical Demands and Work Environment

• Work Environment: This position can be situated in either Schaumburg, Ill or Alpharetta, GA and operates in a professional office environment
• Positions Type/Standard Schedule: This is a full-time position, Monday through Friday, works onsite 3 days a week
• Travel: Travel is expected for this position as needed; 20-25% (to Alpharetta, GA or Schaumburg, Ill)
• Physical Demands: The level and duration of physical exertion generally required to perform critical tasks in support of critical job functions, for example - sitting, standing, walking, lifting, carrying, reaching, pushing, and pulling.