Senior Billing/ Accounts Receivable Specialist

About the role

Hybrid role based in NYC or Chicago (3 days per week in office). Local candidates only.

Responsibilities

• Billing & Payment Processing: Process direct bill premium payments received via check, ACH, credit card, and online payment portals; own cash application and post payments accurately to policyholder accounts; apply credits, endorsements, and policy changes; reconcile daily payment batches; make decisions on payment exceptions and refund workflows, escalating only where policy requires.
• Accounts Receivable Management: Monitor accounts receivable ageing reports and follow up on past-due balances; contact policyholders, agents, and brokers regarding outstanding premium balances; process reinstatements and returned payments (NSF) and update account records; write off uncollectable balances per company policy.
• Reconciliation & Reporting: Own multi-system reconciliation across billing and accounting platforms; support month-end and quarter-end account reconciliations; identify and resolve billing discrepancies or unusual account activity; prepare and distribute AR aging summaries, collection activity, cash application reports, and other financial data using Excel; support internal and external audits by providing documentation and account detail.
• Collaboration: Respond promptly and professionally to billing inquiries from policyholders and agents; collaborate with internal departments to resolve billing issues; research and resolve payment disputes, duplicate payments, and misapplied funds; maintain accurate records of all customer interactions and account notes.
• Documentation & Training: Participate in training on regulatory updates, system enhancements, and departmental procedures.

Requirements

• 3+ years in billing, accounts receivable, or cash application.
• Proficient in Microsoft Excel (pivot tables, VLOOKUPs, formulas).
• Strong attention to detail and ability to interpret complex billing structures.
• Excellent verbal and written communication skills for interacting with clients and internal teams.
• Ability to investigate and resolve discrepancies efficiently.
• Ability to make sound decisions on exceptions and drive resolution independently.
• Strong time management skills to prioritize and handle multiple tasks effectively.

Preferred Qualifications

• Insurance industry experience.
• Accounts Receivable and/or Cash Application experience.

Benefits

• Base Salary: $75,000 – $85,000.
• Bonus.
• Health Benefits.
• Employee options grant.
• 401K with employer match.
• Flexible paid time off.
• Paid national holidays.