Senior Benefits Analyst

Teaching Strategies, LLC

Senior Benefits Analyst responsible for benefits reconciliation and compliance in a fast-paced edtech organization. Leading analysis and managing the financial oversight of self-insured medical plans.

Posted 5/5/2026full-timeRemote • Texas • 🇺🇸 United StatesSeniorWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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)

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

benefits administrationfinancial analysisreconciliationclaims analyticsdata analysisreporting dashboardsstop-loss insurancecompliancejournal entriesvariance analysis

Soft Skills

attention to detailproblem-solvingability to manage multiple prioritiescross-functional collaborationcommunicationstrategic thinkinginsight generationvendor managementaudit readinesstrend analysis

Certifications

Bachelor’s degree in FinanceBachelor’s degree in AccountingBachelor’s degree in HRCEBS