Senior Benefits Analyst (Remote)

Teaching Strategies, LLC•Denton, TX

4d•Remote

About The Position

Join a working team that is dedicated to the mission of the work we do! Teaching Strategies is an innovative edtech organization focused on connecting teachers, children, and families. As front runners in the early childhood education market, we build dynamic, top-quality digital products that integrate all of the essential elements of a high-quality solution: curriculum, assessment, professional development, and family engagement. We are building a team of results-oriented individuals who will thrive in a collaborative, work-hard/play-hard culture. We pride ourselves on the impact we have on the early childhood field through supporting teachers who are doing the most important work there is, teaching children to become creative, confident thinkers. 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.

Requirements

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
Experience managing or supporting self-insured health plans required
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)

Nice To Haves

CEBS or other relevant certification is a plus, but not required
IBNR experience is a plus

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