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Senior Benefits Analyst (Remote)

Teaching StrategiesRemoteMay 13th, 2026
Senior Benefits Analyst (Remote) Department:People OperationsEmployment Type:Full TimeLocation:Denton, TexasDescription The Senior Benefits Analyst plays a key role in ensuring the accuracy, financial integrity, and operational effectiveness of the company's benefits programs. This role is responsible for leading monthly benefits reconciliations, managing financial oversight of the self‐insured medical plan, and driving data‐informed decisions to optimize cost, compliance, and employee experience. This is a highly analytical and detail‐oriented role that partners closely with Finance, Payroll, external vendors, and People Ops to ensure our benefits programs run efficiently and scale with the organization.Specific Roles & Responsibilities: Benefits Financial Management & ReconciliationLeads 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 billingInvestigates and resolves discrepancies, ensuring timely and accurate correctionsDevelops and maintains reconciliation processes, controls, and documentation to support audit readinessProvides monthly reporting and insights on benefits spend, trends, and variancesSelf-Insured Plan ManagementProvides support in managing the financial and operational oversight of the company's self‐insured medical planReviews and analyzes claims data, stop‐loss coverage, and funding levelsPartners with brokers, TPAs, and carriers to monitor plan performance and cost driversTracks and reconciles claims funding, administrative fees, and stop‐loss reimbursementsIdentifies trends and recommends strategies to manage costs and improve plan efficiencyData Analysis & ReportingAnalyzes benefits utilization, enrollment trends, and cost drivers to inform strategyWorks with the Director of People Operations to build dashboards and reports to provide visibility into benefits performanceSupports forecasting and budgeting processes related to benefits spendProvides insights and recommendations to People Ops and leadershipFinancial Reporting & Close SupportPartner with Finance during the monthly and quarterly close process to ensure accurate accounting of benefits-related expenses and liabilitiesPrepare and validate journal entries related to benefits costs, including claims funding, stop‐loss premiums, and administrative feesReconcile benefits-related general ledger accounts and support variance analysis Cash Flow & Funding ManagementMonitor and manage claims funding requirements, ensuring appropriate cash flow for self‐insured plan obligationsPartner with Finance to track timing of large claims, stop‐loss reimbursements, and vendor paymentsProvide visibility into short‐ and long‐term funding needsVendor Management & OperationsServes as a key point of contact for benefits vendors, brokers, and administratorsEnsures vendor invoices align with contractual terms and enrollment dataSupports vendor performance reviews and issue resolutionAssists in annual open enrollment planning and executionOwns carrier file processes, including testing, data reconciliation, and diagnosing data file issues to drive timely resolutionAssists in annual open enrollment planning and execution, including carrier implementation, ensuring system readiness, data accuracy, and smooth execution of enrollment processesCompliance & Risk ManagementEnsures compliance with all applicable regulations (ERISA, ACA, HIPAA, COBRA, etc.)Supports audits, filings (e.g., Form 5500), and documentation requirementsMaintains accurate plan documentation, controls, and reporting processesQualificationsBachelor's degree in Finance, Accounting, HR, or related field5–8+ years of experience in benefits administration, with strong emphasis on financial analysis and reconciliationCEBS or other relevant certification is a plus, but not requiredExperience managing or supporting self‐insured health plans requiredIBNR experience is a plusStrong understanding of benefits compliance and regulatory requirementsAdvanced 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 skillsAbility to manage multiple priorities and work cross‐functionallyExperience in a high‐growth/fast‐paced environmentExperience with stop‐loss insurance and claims analyticsExperience building reporting dashboards (e.g., Excel or similar tools)#J-18808-Ljbffr