Senior Benefits Analyst (Remote)

Specific Roles & Responsibilities:

• Leads monthly benefits reconciliations across all benefit plans (medical, dental, vision, FSA/HSA, 401(k), etc.) 
• Partners with Payroll and Finance to ensure accurate deductions, employer contributions, and vendor billing 
• Investigates and resolves discrepancies, ensuring timely and accurate corrections 
• Develops and maintains reconciliation processes, controls, and documentation to support audit readiness 
• Provides monthly reporting and insights on benefits spend, trends, and variances 

• Provides support in managing the financial and operational oversight of the company’s self-insured medical plan 
• Reviews and analyzes claims data, stop-loss coverage, and funding levels 
• Partners with brokers, TPAs (Third-Party Administrators), and carriers to monitor plan performance and cost drivers 
• Tracks and reconciles claims funding, administrative fees, and stop-loss reimbursements 
• Identifies trends and recommends strategies to manage costs and improve plan efficiency 

• Analyzes benefits utilization, enrollment trends, and cost drivers to inform strategy 
• Works with the Director of People Operations to build dashboards and reports to provide visibility into benefits performance 
• Supports forecasting and budgeting processes related to benefits spend 
• Provides insights and recommendations to People Ops and leadership

• Partner with Finance during the monthly and quarterly close process to ensure accurate accounting of benefits-related expenses and liabilities 
• Prepare and validate journal entries related to benefits costs, including claims funding, stop-loss premiums, and administrative fees 
• Reconcile benefits-related general ledger accounts and support variance analysis

• Monitor and manage claims funding requirements, ensuring appropriate cash flow for self-insured plan obligations 
• Partner with Finance to track timing of large claims, stop-loss reimbursements, and vendor payments 
• Provide visibility into short- and long-term funding needs

• Serves as a key point of contact for benefits vendors, brokers, and administrators 
• Ensures vendor invoices align with contractual terms and enrollment data 
• Supports vendor performance reviews and issue resolution 
• Assists in annual open enrollment planning and execution
• Owns carrier file processes, including testing, data reconciliation, and diagnosing data file issues to drive timely resolution.
• Assists in annual open enrollment planning and execution, including carrier implementation, ensuring system readiness, data accuracy, and smooth execution of enrollment processes

• Ensures compliance with all applicable regulations (ERISA, ACA, HIPAA, COBRA, etc.) 
• Supports audits, filings (e.g., Form 5500), and documentation requirements 
• Maintains accurate plan documentation, controls, and reporting processes 

• Bachelor’s degree in Finance, Accounting, HR, or related field 
• 5–8+ years of experience in benefits administration, with strong emphasis on financial analysis and reconciliation
• CEBS or other relevant certification is a plus, but not required
• Experience managing or supporting self-insured health plans required
• IBNR experience is a plus
• Strong understanding of benefits compliance and regulatory requirements 
• Advanced Excel skills (pivot tables, VLOOKUP/XLOOKUP, data analysis)
• Experience working with HRIS and payroll systems (e.g., Rippling, Dayforce, ADP) 
• High attention to detail with strong problem-solving skills
• Ability to manage multiple priorities and work cross-functionally
• Experience in a high-growth/fast-paced environment
• Experience with stop-loss insurance and claims analytics
• Experience building reporting dashboards (e.g., Excel or similar tools)