Group Health and Benefits Billing and Payments Specialist

Location: Remote (U.S.-based) or Seattle, WA (Hybrid/In-Office Option) Reports To: Director of Operations Employment Type: Full-Time Salary Range: $65,000 – $95,000, depending on experience and qualifications About TailorWell TailorWell Holdings, Inc. is an enrollment, benefits billing and premium remittance technology company and licensed insurance agency. Our proprietary platform calculates precise premium obligations from real-time eligibility data, generates consolidated employer invoices, collects premiums, and remits payments directly to health plans and other insurance carriers with member-level detail. We serve employers and their brokers across the small group health insurance market and are expanding into the Individual Coverage Health Reimbursement Arrangement (ICHRA) market, where our precision billing and direct carrier payment capabilities address a critical infrastructure gap. Our platform processes millions of dollars in monthly premium transactions, maintaining eligibility records, generating invoices, and executing carrier payments with accuracy that our clients and carrier partners rely on. Position Summary We are hiring a Billing Specialist to support the financial operations of our health insurance billing and premium remittance programs. This individual will manage a range of payment processing, reconciliation, and carrier remittance activities, working daily with TailorWell’s proprietary billing platform and external banking systems. The role involves direct interaction with employers, insurance carriers, brokers, and service providers. You will be responsible for ensuring that premiums are collected accurately from employers and remitted correctly to carriers — on time, every month. Because our billing drives coverage, accuracy and timeliness in this role directly affect whether employees and their families have active health insurance. This is a hands-on operational role with significant responsibility and visibility. You will develop deep expertise in how health insurance billing and premium remittance works end-to-end, gaining exposure to employer-sponsored benefits, carrier operations, broker relationships, and the emerging ICHRA market. Key Responsibilities Premium Collection and Employer Payments • Use TailorWell’s proprietary billing platform and multiple bank portals to initiate and process EFT/ACH collections from employers on their monthly billing cycle. • Process and apply check payments and wire transfers received from employers, matching payments to outstanding invoices with member-level accuracy. • Monitor employer payment status and proactively follow up on late or missing payments before they affect carrier remittance deadlines. • Reconcile employer billing discrepancies — investigating differences between invoiced amounts and payments received, identifying root causes (eligibility changes, retroactive adjustments, payment timing), and resolving issues in coordination with employers and brokers. • Communicate payment status, discrepancies, and resolution timelines to employers and brokers professionally and promptly. Carrier Premium Remittance • Prepare and process premium remittance payments to health insurance carriers and other benefit providers (dental, vision, life, disability), ensuring each payment is accompanied by accurate member-level remittance detail. • Verify that remittance amounts reconcile to collected employer premiums and current eligibility data before payments are released. • Monitor carrier payment confirmations and resolve any carrier-reported payment discrepancies, including misapplied payments, missing members, or premium amount disagreements. • Coordinate with carriers on payment timing requirements, grace periods, and any special remittance instructions to prevent coverage disruptions. • Support the weekly EDI eligibility file transmission process to carriers, ensuring that enrollment data supporting premium remittances is current and accurate. Broker Commission and Vendor Payments • Process commission payments to brokers based on earned commission schedules and carrier commission receipts. • Process fee payments to service vendors and third-party administrators. • Reconcile commission and fee accounts, ensuring payments align with contractual terms. Reconciliation and Record-Keeping • Maintain accurate ledgers and transaction records across all payment types — employer collections, carrier remittances, broker commissions, and vendor payments. • Perform daily and monthly reconciliation of bank accounts, billing system records, and carrier payment confirmations. • Identify and escalate systemic billing or payment issues that indicate process improvements are needed. • Prepare reports on payment activity, outstanding balances, collection rates, and remittance status for management review. • Support month-end and year-end close processes related to premium receivables and payables. Communication and Collaboration • Serve as a primary point of contact for employer and broker inquiries related to billing, payment, and account status. • Communicate professionally with internal teams and external partners via email, phone, and video meetings. • Collaborate with the eligibility and enrollment team to ensure that billing records reflect current enrollment data, and that eligibility changes are properly reflected in invoices and remittances. • Participate in process improvement initiatives as TailorWell scales its billing operations, including support for ICHRA billing workflows as the company expands into this market. Qualifications and Experience Required • 5+ years of experience in accounts receivable, cash management, payment processing, or financial operations. • Experience working with bank systems, ACH/EFT processing, and online payment portals. • Strong understanding of accounting principles, particularly as applied to receivables, payables, and reconciliation. • Demonstrated ability to manage high-volume transaction processing with consistent accuracy and attention to detail. • Experience investigating and resolving billing discrepancies, with the ability to trace issues across multiple systems and stakeholders. • Familiarity with ledgers, billing systems, and financial record-keeping. • Strong communication skills, both written and verbal, with the ability to explain billing issues clearly to non-financial stakeholders including employers, brokers, and carrier contacts. • Highly organized, responsive, and able to manage multiple priorities within recurring monthly billing cycles and payment deadlines. • Proficiency with Microsoft Excel and comfort working with data exports, pivot tables, and lookup functions for reconciliation and analysis. • Ability to work independently in a remote environment with minimal supervision, while maintaining consistent communication with the team. Preferred • Prior experience in group health insurance billing, employee benefits administration, or insurance premium processing. • Knowledge of how employer-sponsored health insurance billing works: eligibility, enrollment, premium calculation, carrier remittance, and the roles of brokers and TPAs. • Experience with EDI (Electronic Data Interchange) transactions in a health insurance context, particularly 834 enrollment files. • Familiarity with Individual Coverage Health Reimbursement Arrangements (ICHRA) or individual health insurance billing and payment. • Experience with association health plans or multiple employer welfare arrangements (MEWAs). • Prior experience at an insurance agency, TPA, general agency, or carrier billing department. • College degree preferred but not required — relevant work experience is valued equally. What Success Looks Like In this role, you are succeeding when: • Employer payments are collected on time and applied accurately, with discrepancies identified and resolved before they affect carrier remittance. • Carrier premium remittances are processed on schedule with accurate member-level detail, and carriers confirm payments without discrepancies. • Employers and brokers describe their billing experience with TailorWell as responsive, transparent, and easy to work with. • Reconciliation is current — bank balances, billing system records, and carrier confirmations align without unexplained variances. • You are proactively identifying issues and patterns rather than reacting to problems after they escalate. • You are building institutional knowledge about how our clients, carriers, and billing cycles work, becoming a trusted resource for the team. Compensation and Benefits • Salary range: $65,000 – $95,000, depending on experience and qualifications. • Annual performance bonus opportunity. • Health insurance benefits. • Flexible remote work arrangement (U.S.-based); hybrid/in-office option available in Seattle, WA. • Opportunity to grow with the company as TailorWell expands and scales its billing operations. Why TailorWell TailorWell is at the intersection of two powerful trends: the shift from group health insurance to defined contribution, and the growing demand for precise, technology-driven billing and payment infrastructure in the benefits industry. Our platform solves a real problem — getting the right amount of money to the right carrier at the right time — and the person in this role is essential to making that happen every day. You will join a small team where your work is visible, your contribution is recognized, and your growth is supported. If you care about accuracy, take pride in getting the details right, and want to be part of a company that is building something meaningful in healthcare, we want to hear from you. TailorWell Holdings, Inc. is an equal opportunity employer.