Lead financial management and reconciliation of employee benefits, manage self-insured medical plan finances and claims analytics, partner with Payroll and Finance, build reporting and dashboards, ensure compliance and audit readiness, support vendor management and open enrollment, and provide insights to optimize benefits cost and operations.
Be a Part of our Team!
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.
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 is the leading provider of curriculum, assessment, professional development, and family connection resources in the early childhood field. Offering ground-breaking solutions, including The Creative Curriculum®, GOLD®, tadpoles®, ReadyRosie™, ParentPal™, Al's Pals™, and professional development, Teaching Strategies believes that a child’s first 8 years form a critical foundation for school success. Teaching Strategies has been an advocate for the early childhood education community for more than 40 years.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
