Teaching Strategies

Senior Benefits Analyst (Remote)

Teaching Strategies$75K — $95K *
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Finance, Accounting, HR, or related field
  • 5-8+ years of experience in benefits administration
  • Experience managing or supporting self-insured health plans
  • Strong understanding of benefits compliance and regulatory requirements
  • Advanced Excel skills including data analysis and pivot tables
  • Experience with HRIS and payroll systems (e.g., Rippling, Dayforce, ADP)
  • High attention to detail and strong problem-solving skills

Responsibilities

  • Lead monthly benefits reconciliations across all benefit plans
  • Partner with Payroll and Finance to ensure accurate financial processes
  • Investigate and resolve discrepancies in benefits administration
  • Provide insights on benefits spend, trends, and performance
  • Manage and analyze the company's self-insured medical plan
  • Prepare financial reports related to benefits expenses during close processes
  • Serve as a primary point of contact for benefits vendors and brokers

Benefits

  • Remote work flexibility
  • Opportunities for professional development and certifications
  • Collaborative work environment with cross-departmental partnerships
  • Health, dental, and vision insurance options
  • Employee assistance programs and wellness initiatives
  • Generous paid time off and holiday policies
  • 401(k) plan with employer contributions and matching
Full Job Description
Senior Benefits Analyst (Remote)

Department: People Operations

Employment Type: Full Time

Location: Denton, Texas

Description

Position Overview

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 our 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 & Reconciliation
  • 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

Self-Insured Plan Management
  • 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

Data Analysis & Reporting
  • 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

Financial Reporting & Close Support
  • 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

Cash Flow & Funding Management
  • 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

Vendor Management & Operations
  • 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

Compliance & Risk Management
  • 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

Qualifications:
  • 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)

About Teaching Strategies

Teaching Strategies is a leading provider of early childhood education resources, including curriculum, assessment, professional development, and family engagement tools. The company's flagship product, The Creative Curriculum, is widely used in preschools and other early childhood education settings across the United States. Teaching Strategies was founded in 1988 and is headquartered in Bethesda, Maryland.
Learn more about Teaching Strategies
Size
500 employees
Industry
Founded
1988

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