Billing Specialist in Washington, District of Columbia at First Gen Financial

About First Gen Financial

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!

Title: Billing Specialist

Location: Remote (U.S.)

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

Employment Type: Full-time 1099 Contractor with potential conversion

The Role

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.

Key Responsibilities

• 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

What You’ll Do Day-to-Day

• 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

What Success Looks Like

Within 2 Month:

• Full ownership of the AR/AP billing cycle with minimal supervision
• All carrier reconciliations completed on time with <2% error rate
• Aging AR under 30 days for 90%+ of the book

Within 3 Months:

• Documented and optimized billing workflows and escalation procedures
• DSO at or below industry benchmark for the health insurance space
• Identified and recovered retroactive billing errors exceeding prior quarter baseline

Within 6 Months:

• Supporting transaction volume growth beyond with no proportional increase in error rate or aging
• Recognized as the operational anchor for billing integrity across the client portfolio
• Contributing to system improvements, automation initiatives, or billing policy development

Requirements

• 2+ years of billing, AR/AP, or accounting experience in health insurance, employee benefits, TPA, or related financial services
• Working knowledge of group health and/or life insurance premium billing structures (fully-insured, level-funded, or MEC preferred)
• Experience reconciling carrier invoices and processing employer group remittances
• Proficiency with billing systems, accounting software (QuickBooks, NetSuite, or similar), and Excel/Google Sheets
• Strong attention to detail with the ability to manage high transaction volumes accurately under deadline pressure
• Excellent written and verbal communication skills for client-facing billing conversations
• Self-directed, organized, and comfortable operating in a fast-moving startup environment
• Bonus: experience with ADP, Viventium, or similar payroll platforms for deduction reconciliation

Who You Are

You’re precise by nature and relentless by habit. You don’t let a billing discrepancy sit, you chase it down, document it, and fix it. You understand that in the insurance space, accuracy isn’t just good practice; it’s a compliance obligation and a client trust issue.

You embody First Gen’s core values:

• Ironclad Integrity: You do the right thing, even when no one is watching, especially with other people’s money.
• 24-Carat Accountability: You own your numbers, your errors, and your outcomes without deflection.
• Catalyst: You look for smarter ways to reconcile, collect, and process, and you bring those ideas to the table.
• Wholehearted: You treat clients like partners, not account numbers, and your communication reflects that.

You’re not just looking for a billing job. You’re looking for a place where your precision and work ethic directly impact business owners, their teams, and the financial stability of the people we serve.