Billing Specialist

We’re a fast-growing, purpose-driven B2B financial services company built on integrity, accountability, and continuous growth. We have developed our own proprietary insurance product for employers which is scaling rapidly. Our leadership team brings proven expertise from multiple sectors of finance, and every team member plays a direct role in expanding both our clients’ success and our company’s vision. We unlock capital to empower teams!

Location: Remote (U.S.)

Compensation: $55,000 - $60,000 Base + Performance Bonus

Employment Type: Full-time 1099 Contractor with potential conversion

We’re looking for a proactive, detail-oriented Billing Specialist who thrives in a fast-paced, compliance-driven environment. You’ll own the full AR/AP billing cycle for a high value transaction portfolio, managing premium collections, carrier remittances, employer invoicing, and reconciliation across our health and life insurance book of business.

This is not a back-office clerical role. You’ll serve as part of the financial arm of our client operations, the person who ensures every dollar in and out is tracked, accurate, and resolved with urgency. You’ll work closely with Account Executives, Customer Success, and leadership to keep billing frictionless for clients and compliant for the business.

• Manage the full AR/AP billing cycle for health and life insurance accounts
• Generate, issue, and track monthly employer invoices for group health and life premiums
• Process inbound premium payments and apply accurately to client accounts within carrier and compliance deadlines
• Reconcile carrier remittance reports against employer contributions and employee payroll deductions
• Investigate and resolve billing discrepancies, short payments, and return items with speed and precision
• Coordinate with carriers on enrollment changes, retroactive adjustments, and termination billing
• Monitor aging AR and execute structured follow-up protocols to minimize past-due balances
• Process AP disbursements to carriers, vendors, and partners on schedule
• Maintain accurate records in billing systems and CRM; ensure audit-ready documentation at all times
• Support month-end close with reconciliations, reporting, and variance analysis
• Collaborate cross-functionally with Customer Success, Account Executives, and Operations on client billing escalations

• Run daily AR aging reports and prioritize outreach on outstanding balances
• Process and post premium payments from employers via ACH, check, and wire transfer
• Reconcile carrier bills against internal enrollment data and flag discrepancies for resolution
• Communicate with clients via phone and email to resolve billing questions and collect past-due amounts professionally
• Coordinate retroactive adjustments, adds, terms, and COBRA billing with carriers and internal teams
• Prepare weekly AP disbursement runs and obtain appropriate approvals
• Maintain organized billing files and support audit requests from carriers, partners, or compliance teams
• Track KPIs including days sales outstanding (DSO), collection rates, and reconciliation accuracy

• Full ownership of the AR/AP billing cycle with minimal supervision
• All carrier reconciliations completed on time with