Senior Benefits Analyst (Remote)

🇺🇸 Remote - US 🕑 Full-Time 💰 TBD 💻 Human Resources 🗓️ May 7th, 2026

Rive

Edtech.com's Summary

Teaching Strategies, LLC is hiring a Senior Benefits Analyst. The role requires leading monthly benefits reconciliations, managing financial oversight of the company's self-insured medical plan, and driving data-informed decisions to optimize cost, compliance, and employee experience. The analyst will collaborate closely with Finance, Payroll, external vendors, and People Operations to ensure efficient benefits program operations that scale with the organization.

Highlights

Lead monthly benefits reconciliations across medical, dental, vision, FSA/HSA, 401(k), and other plans

Manage financial oversight of self-insured medical plan including claims data analysis and stop-loss coverage

Analyze benefits utilization, enrollment trends, and cost drivers to inform strategic decisions

Partner with Finance on monthly and quarterly close processes, journal entries, and general ledger reconciliation

Monitor and manage cash flow for claims funding and vendor payments

Serve as primary contact for benefits vendors, brokers, and administrators; manage vendor invoicing and issue resolution

Ensure compliance with ERISA, ACA, HIPAA, COBRA, and maintain audit readiness

Bachelor’s degree in Finance, Accounting, HR, or related field with 5-8+ years in benefits administration and financial analysis

Proficiency with advanced Excel functions and experience with HRIS/payroll systems such as Rippling, Dayforce, ADP

Experience managing self-insured health plans, stop-loss insurance, claims analytics, and building reporting dashboards

Senior Benefits Analyst (Remote) Full Description

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.