Senior Director, Billing & Client Invoicing in Schaumburg, Illinois at Wheels, Inc.

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)

• 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

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.

• 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.

CULTURAL ATTRIBUTES

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.

JOB SPECIFICATIONS, PHYSICAL DEMANDS AND WORK ENVIRONMENT

Work Environment: This position is in 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

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:

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.

As one of the largest fleet management companies in North America, Wheels features a portfolio of 900,000+ vehicles under management across the continent, a global alliance in 61 countries, and a client base that consists of some of the best-known businesses in the world. No matter the industry type or business size, we’re proud to work across sales and service fleets, trucks and equipment, and last mile delivery to ensure we power your potential.

The culture at Wheels is the secret to our 80+ years of success. And the reason people choose to join — and stay with — our team.

When you join the team, you'll work with professionals who are passionate, friendly and smart. We foster a welcoming and inclusive environment for all, combined with the encouragement to continuously learn and grow. From day one, we invest in your long-term development through annual performance goals and reviews, educational and wellness programs, awards and celebrations, and more.

Ready to experience the Wheels culture for yourself?

• 10 years average employee tenure

• 10 times recognized as one of Chicago's Best and Brightest Companies to Work For

• 50+ health, wellness and engagement benefits

• 2,500+ online learning programs

Diversity: Wheels deeply values the strength of diversity both in the communities we serve and our own employee base. This includes treating everyone as equal, respecting and valuing diversity, providing equal opportunity and fostering a safe space to work.

Community: We are heavily involved in the communities where we operate. We offer opportunities for employees to make a positive impact through mentorship and tutoring elementary school students, participating in blood drives, donating to United Way and other charitable organizations in the greater Chicagoland and Toronto areas.

Sustainability: Wheels is actively committed to becoming a cleaner fleet management company through recycling programs, public transportation support and more.

We Are Dedicated to the Safety and Health of our Employees

Our employees are critical to delivering on our commitment to client success, which is why we offer a variety of programs focused on the health and wellness of our people.

We hire people who have a customer-focused mindset and a strong collaborative nature. Because at Wheels, customer service and teamwork don't just happen in the office. It is during the informal moments when employee trust is strengthened and friendships are made. We value these moments, which is why we host departmental contests, summer gatherings, family events, holiday celebrations and more.

At Wheels, your well-being is our priority. As part of our commitment to your health and well-being, we’re proud to offer access to the Advocate Health Care Wellness Portal—a personalized platform designed to help you take charge of your health journey.

The 2026 Wellness Program is designed to support you in achieving your personal health goals. Best of all, it’s flexible and fits into your busy lifestyle.

This program is designed to support your overall well-being—physically, emotionally, and financially—by providing tools and incentives that encourage healthy living.