Senior Director, Billing & Client Invoicing

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.

• →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

• Excellent communication skills
• Team Management skills

• 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

At Wheels, we believe in fostering a culture that is built on our Core Values and Guiding Principles. We cultivate a culture of excellence and innovation by upholding these values, driving our collective success and growth.

• Integrity – Always act with integrity and honesty.
• One Team – Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference.
• Innovation – Drive continuous improvement, spark creativity and embrace next generation thinking.
• Customer Success – Ensure that customer and driver success is at the heart of everything we do.

At Wheels, leaders are expected to model and champion our cultural attributes through their actions:

• Discipline Drives Quality – Plan the Trip: Think proactively, hold a high bar, follow through by leveraging experience and systems. To produce quality outcomes, we must be intentional and deliberate in everything we do, from big bets to daily execution.
• Intellectually Curious – Fuel Your Minds: Be bold, challenge assumptions, think differently, look outside the box. Strive to unlock your own thinking and create new possibilities.
• Commit and Deliver – Own It: Take responsibility for your work, from start to finish, and be accountable for the results. Think and act like an owner of the business.
• Relationships Matter – Share the Ride: Trust is central, both with key internal and external stakeholders. Relationships are not a side effect of work but a driver of success.

• 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.

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.