Senior Billing Specialist

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.