Senior Director, Billing & Client Invoicing
Wheels, LLC · Schaumburg, IL · 3 wk ago
HybridAccountingFull-time
Key Responsibilities
- 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.
- 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.
- 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.
- 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.
- Maintain documentation standards and monitor and resolve billing discrepancies and client inquiries.
Competencies
- 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
Cultural Attributes
- Discipline Drives Quality – Plan the Trip: Think proactively, hold a high bar, follow through by leveraging experience and systems.
- 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.