Senior Billing Specialist

Location: NYC or Chicago hybrid (3 days/week in office). Local candidates only.

What You'll Do

The Senior Billing Specialist is responsible for managing and processing direct bill premium payments within our insurance billing systems. This position owns cash application, multi-system reconciliation, and decision making around payment exceptions and refund workflows, and plays a key role in ensuring accurate, timely posting of policyholder payments, resolving billing discrepancies, and maintaining clear communication internally and externally with agents, brokers, and insureds. The ideal candidate has the ability to navigate multiple systems, manage complex billing processes, and exercise judgment and autonomy in resolving exceptions. This role sits on the professional accounting track and requires experience in insurance or billing. This role demands accuracy, analytical thinking, problem solving and excellent communication skills.

Key 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 in the billing management systems
• Apply credits, endorsements, and policy changes to accounts
• Reconcile daily payment batches and ensure all transactions balance at end of day
• 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 by phone and email regarding outstanding premium balances
• Process reinstatements and returned payments (NSF) and update account records accordingly
• 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, escalating to the Billing Manager where appropriate
• 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 as requested

Collaboration

• Respond promptly and professionally to billing inquiries from policyholders and agents
• Collaborate with internal departments, including finance, customer service, and underwriting, to resolve billing issues
• Research and resolve payment disputes, duplicate payments, and misapplied funds
• Maintain accurate records of all customer interactions and account notes in the billing system

Documentation & Training

• Participate in training on regulatory updates, system enhancements, and departmental procedures

Basic Requirements

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

Preferred Qualifications:

• Insurance industry experience a plus
• Accounts Receivable and or Cash Application experience a plus

Benefits

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