Senior Billing​/Accounts Receivable Specialist

Senior Billing/ Accounts Receivable Specialist

Chicago, IL;
New York City, NY

Honeycomb Insurance

At Honeycomb, we're not just building technology; we're reshaping the future of insurance.

In 2025, Honeycomb was recognized by Dun & Bradstreet as "Top 10 Best Start Up Companies to Work For" in Israel, named by Linked In as "Top 10 Startups in Chicago", and Newsweek's "Greatest Startup Workplaces in America, 2025". Through the first half of 2026 we've been recognized on Inc. Magazine's "Best Workplaces" List and Forbes "Fintech 50".

How did we earn these honors?

Honeycomb is a rapidly growing global startup, generously backed by top-tier investors and powered by an exceptional team of thinkers, builders, and problem-solvers. Dual-headquartered in Chicago and Tel Aviv (R&D center), and with 6 offices across the U.S., we are reinventing the commercial real estate insurance industry, an industry long overdue for disruption. Just as importantly, we ensure every employee feels deeply connected to our mission and one another.

With over $100B in insured assets, Honeycomb operates across 23 states, covering more than 65% of the U.S. population and increasing its coverage.

If you're looking for a place where innovation is celebrated, culture actually means something, and smart people challenge you to be better every day - Honeycomb might be exactly what you've been looking for.

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,…