Executive Director, Enterprise Billing & Invoicing

Wheels, LLC; Schaumburg (IL); On-site; USD 157,000 - 220,000; Full time

Job summary

Wheels, LLC in Schaumburg, IL seeks a Senior Director of Billing & Client Invoicing to lead a critical function across fleet leasing and services. You will oversee complex invoicing for 2,000 clients and 800,000 leased vehicles, ensuring accurate, timely, and client-tailored billing.

The role requires strategic leadership of a multi-layer billing organization, design of customized invoices (EDI and client layouts), strong controls, and collaboration with Sales, Client Management and Operations

Qualifications

• 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.

Responsibilities

• Lead, coach and develop a multi-layered billing and invoicing organization across billing ops, invoice configuration, dispute resolution and enablement.
• Oversee end-to-end billing process ensuring accuracy, timeliness and completeness.
• Design and deliver customized invoice formats, including EDI and client-specific layouts.
• Govern billing technology including EDI, invoice integrations and data processes.
• Partner with Sales, Client Management, Client Services and Onboarding on complex invoicing needs.
• Establish billing standards, controls and change management to prevent delays and AR impact.
• Collaborate with cross-functional leaders to drive revenue recognition and cash collection objectives.

Skills

Leadership

Billing operations

Contract invoicing

Communication

Tools

ERP systems

EDI

Billing software

Job description

Wheels, LLC in Schaumburg, IL seeks a Senior Director of Billing & Client Invoicing to lead a critical function across fleet leasing and services. You will oversee complex invoicing for 2,000 clients and 800,000 leased vehicles, ensuring accurate, timely, and client-tailored billing.

The role requires strategic leadership of a multi-layer billing organization, design of customized invoices (EDI and client layouts), strong controls, and collaboration with Sales, Client Management and Operations