Senior Billing/ Accounts Receivable Specialist

Honeycomb; Chicago, New York (IL, NY); Hybrid; USD 65,000 - 90,000; Full time

Benefits offered by this job

Bonus

Employee options grant

401K with employer match

Flexible paid time off

Paid national holidays

Job summary

Honeycomb Insurance is seeking a Senior Billing/Accounts Receivable Specialist to manage direct bill payments and cash applications. The role focuses on accurate posting, reconciliation, and resolving billing issues with agents, brokers, and insureds.

The ideal candidate has 3+ years in billing/AR, strong Excel skills, and excellent communication. This position offers a hybrid work arrangement with offices in Chicago and NYC and opportunities to contribute to a growing fintech-insurance platform.

Qualifications

• 3+ years in billing, accounts receivable, or cash application.
• Proficient in Microsoft Excel (pivot tables, VLOOKUPs, formulas).
• Excellent communication skills for interactions with clients and internal teams.

Responsibilities

• Process direct bill premium payments via check, ACH, credit card, and online portals.
• Own cash application and post payments to policyholder accounts in billing systems.
• Apply credits, endorsements, and policy changes to accounts.
• Reconcile daily payment batches and ensure transactions balance.
• Decide on payment exceptions and refund workflows; escalate when needed.
• Monitor AR aging and follow up on past-due balances.
• Prepare AR aging summaries and cash application reports.

Skills

Billing

Accounts Receivable

Cash Application

Excel

Communication

Problem Solving

Education

Bachelor's in Accounting or Finance

Job description

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.

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.

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:

• 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


• 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

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


• Bonus


• Employee options grant


• 401K with employer match


• Flexible paid time off


• Paid national holidays