Jeannine Chiappini

Jeannine Chiappini joins edHEALTH in January 2026 as our new Chief Strategy & Membership Officer. She has over 25 years of experience in employee benefits consulting and human resources, with deep expertise in group captives, self-funded health plans, and pharmacy benefit management.

Throughout Jeannine’s career, she has partnered closely with independent schools across the country, developing a nuanced understanding of faculty and staff needs, school culture, budgeting cycles, governance models, and decision-making processes. She has led large consulting teams, crafted multi-year benefits strategies, and served as a trusted advisor to CFOs, CHROs, and school leadership.

Before joining edHEALTH, Jeannine worked on the executive leadership team at Borislow Insurance, which included being part of their captive program. Prior to that, she held management positions at OneDigital and NFP. She’s known for her ability to strengthen member relationships, drive retention, support growth, and create high-impact strategies that align financial stewardship with long-term organizational health.

Jeannine and her family reside on the South Shore of Massachusetts, along with their two rescue dogs, and are avid fans of New England sports, especially the Celtics and Patriots. Lately, she spends a great deal of time cheering on her son’s basketball team!