Senior Billing Specialist

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.
  • Aid in onboarding and training new team members on billing systems, workflows, and company-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.

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.