Senior Billing Specialist

Location: In Office to begin with option to go hybrid after training period.

The Senior Billing Specialist is a high-ownership role on the Finance team, responsible for leading the full billing and accounts receivable cycle across the company's leasing and asset resale portfolio. This position goes beyond day-to-day transaction processing: the Senior Specialist owns complex and high-volume accounts, leads the onboarding of new clients into the billing workflow, and serves as a stabilizing resource for troubled accounts requiring elevated attention. The role also carries a team development component — this person is expected to mentor junior billing staff, help build and refine internal processes, and be a dependable escalation point for billing-related issues across the organization.

The ideal candidate is a seasoned AR professional who combines technical fluency across billing systems with strong client communication skills and the confidence to operate independently in a fast-paced environment.

Essential Duties:

Billing & Accounts Receivable

• Manage the end-to-end billing cycle for a high-volume portfolio of leasing and asset resale accounts, ensuring accurate and timely invoice generation, distribution, and posting.

• Process and apply incoming payments with precision; investigate and resolve payment discrepancies, misapplications, and short pays.

• Monitor AR aging across the full portfolio; proactively escalate and work to resolve delinquent and at-risk accounts.

• Validate debit account data and ensure the integrity of all financial transactions entering the AR system.

• Maintain and update the AR database, including new account setup, balance adjustments, and missed payment records.

• Prepare accurate, data-driven AR status reports and billing activity summaries for Finance leadership.

• Support month-end and quarter-end close activities, including reconciliations and reporting deliverables.

• Calculate late fees and finance charges in accordance with contract terms; ensure accuracy and maintain thorough documentation prior to any client communication.

• Negotiate outstanding balances, late fee assessments, and payment arrangements directly with clients following established guidelines; document all agreed terms and escalate cases as appropriate.

Account Management & Onboarding

• Lead the billing onboarding process for new clients — coordinate with Sales, Operations, and the client to establish billing structures, validate account setup, and ensure a smooth first-invoice experience.

• Take ownership of troubled or complex accounts, identifying root causes of billing discrepancies, payment delays, or disputes and driving resolution with a sense of urgency.

• Serve as the primary billing contact for assigned key accounts; build trusted relationships and provide a high level of service and communication around invoicing, payment status, and account health.

• Partner with Sales and Account Management on billing-related client escalations, providing context, documentation, and resolution support.

• Identify patterns in account issues (disputed charges, setup errors, terms mismatches) and surface systemic fixes to Finance leadership.

Team Leadership & Process Improvement

• Mentor and provide day-to-day guidance to junior Billing and AR staff; serve as an escalation point for questions, edge cases, and system issues.

• Assist in onboarding and training new team members on billing systems, workflows, and our specific processes.

• Contribute to the development and documentation of standard operating procedures for the billing function.

• Identify inefficiencies in current billing processes and proactively recommend improvements to increase accuracy, speed, and scalability.

• Assist Finance management with workload distribution and coverage planning during high-volume periods.

• Perform other duties and responsibilities as assigned.

Education and Experience:

• Minimum 4-5 years of progressive experience in billing, accounts receivable, or a related financial operations role.

• Demonstrated ability to manage high-volume, complex account portfolios independently.

• Experience onboarding new accounts into a billing system and resolving disputed or delinquent accounts.

• Proficiency in Microsoft Office with advanced Excel skills (pivot tables, VLOOKUP, complex formulas).

• Solid understanding of AR best practices, billing controls, and applicable customer data regulations.

• High degree of numerical aptitude, accuracy, and trustworthiness when handling sensitive financial data.

• Strong client-facing communication skills — written and verbal — with the ability to handle difficult conversations professionally.

Preferred Experience & Skills:

• Experience with Salesforce, QuickBooks, NetSuite, and/or Ariba.

• Prior experience mentoring or training billing/AR team members.

• Exposure to equipment leasing, asset finance, or a related B2B financial services environment.

• Bachelor's degree in Finance, Accounting, or a related field.