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
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Leadership & Team Management
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Lead, coach and develop a multi-layered billing and invoicing organization spanning billing operations, client invoice configuration, dispute resolution and billing enablement functions.
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Establish clear performance expectations, KPIs, and accountability standards
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Foster a culture of accuracy, responsiveness, and continuous improvement
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Billing Operations
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Oversee the end-to-end billing process, ensuring accuracy, completeness, and timeliness
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Manage high-volume, multi-line invoicing across leasing and ancillary service offerings
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Ensure proper revenue capture and alignment with contractual terms
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Invoice Design, Technology & Governance
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Design and deliver customized invoice formats, including EDI and bespoke client-specific layouts, while maintaining standardization, accuracy, and scalability
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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
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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
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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
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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
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Establish enterprise billing standards and controls across upstream operational and product teams whose transactions ultimately flow to client invoices.
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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.
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Leverage systems, automation, and data controls reduce manual effort, improve billing accuracy, and support scalable growth without compromising control or client experience.
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Serve as the enterprise decision authority for billing standards, invoice design, ensuring products and services are billing‑ready before being scaled.
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Controls & Compliance
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Establish and maintain strong internal controls over billing accuracy, revenue recognition and invoice completeness.
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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.
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Support audit requirements and maintain documentation standards
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Monitor and resolve billing discrepancies and client inquiries
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Cross-Functional Collaboration
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Work closely with Finance, Operations, Sales, and Client Services
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Act as a key liaison for billing-related client escalations
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Supporting broader finance transformation and process improvement initiatives
Leadership Responsibilities Strategy
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Motivate a high-performing billing team with strong ownership and accountability
COMPETENCIES - SKILLS
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Excellent communication skills
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Team Management skills
EDUCATION AND EXPERIENCE
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10+ years of progressive experience in accounting, finance, billing, revenue operations, or order-to-cash environments
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Proven leadership experience managing teams in high-volume, complex billing environments
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Experience with contract-based, multi-service invoicing (leasing, usage-based, or subscription models preferred)
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Strong understanding of billing systems, ERP platforms, and data structures
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Demonstrated ability to design and implement scalable processes
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High attention to detail with strong analytical and problem-solving skills
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Excellent communication skills, with the ability to interface directly with clients and senior leadership
CORE VALUES
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.
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Integrity – Always act with integrity and honesty.
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One Team – Treat others with dignity and respect; act as a cohesive, inclusive and accountable team that is making a difference.
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Innovation – Drive continuous improvement, spark creativity and embrace next generation thinking.
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Customer Success – Ensure that customer and driver success is at the heart of everything we do.
CULTURAL ATTRIBUTES
At Wheels, leaders are expected to model and champion our cultural attributes through their actions:
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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.
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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.
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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.
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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.
JOB SPECIFICATIONS, PHYSICAL DEMANDS and WORK ENVIRONMENT
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Work Environment: This position can be situated in either Schaumburg, Ill or Alpharetta, GA and operates in a professional office environment
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Positions Type/Standard Schedule: This is a full-time position, Monday through Friday, works onsite 3 days a week
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Travel: Travel is expected for this position as needed; 20-25% (to Alpharetta, GA or Schaumburg, Ill)
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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.
DISCLAIMER
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.
Wheels recognizes benefits are a significant part of your employee experience, and we've created a robust benefits package that is market-leading, competitive offerings so you and your family can receive outstanding care. Please click here for an overview of the benefits available to you and your family.
Pay Range:
$157,100-$219,900
The base salary range for this position is listed above. This position is eligible to participate in the annual incentive plan which is based on company performance and individual performance. Compensation ranges are based on several factors including job function, level, and geographic location. Final offer amounts are determined by multiple factors including candidate experience, education, certifications, skill level and expertise, and may vary from the amounts listed here.
