Senior Billing/ Accounts Receivable Specialist

Honeycomb Insurance•Chicago, IL

8d•$75,000 - $85,000•Hybrid

About The Position

Honeycomb Insurance is a rapidly growing global startup that is reinventing the commercial real estate insurance industry. They are looking for a Senior Billing Specialist to manage and process direct bill premium payments within their insurance billing systems. This position owns cash application, multi-system reconciliation, and decision making around payment exceptions and refund workflows. The role plays a key part 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.

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

Nice To Haves

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

Responsibilities

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