Chapter

Chapter is a Medicare advisory company headquartered in New York City that helps older Americans navigate the notoriously complex process of choosing a Medicare plan. It compares options from every insurance carrier and uses AI to assess factors such as whether a beneficiary's doctors are likely to be in-network or whether they are likely to pass an insurer's underwriting process, with a stated goal of putting seniors' interests ahead of insurer or broker compensation.

The company was founded in 2020 by Cobi Blumenfeld-Gantz, who has continued on as CEO, alongside fellow Wharton alumnus Corey Metzman and Vivek Ramaswamy; Ramaswamy left Chapter's operations at some point after co-founding it and before later pursuing political office, including a 2024 U.S. presidential campaign. Chapter has since drawn an unusually cross-partisan investor and board roster: JD Vance's venture firm Narya Capital led its 2021 Series A and Vance briefly held a board seat before leaving to run for the U.S. Senate, Peter Thiel then took a board seat as an early investor before resigning by 2025, and former Democratic U.S. Health and Human Services Secretary Donna Shalala has since filled that board seat.

Chapter's valuation rose quickly alongside its fundraising: a $75 million Series D led by Stripes in April 2025 valued the company at $1.5 billion, and about a year later a $100 million Series E led by Al Gore's Generation Investment Management roughly doubled that valuation to $3 billion in April 2026.

Since 2025 the company has also expanded beyond plan selection into helping Medicare beneficiaries identify and use unused over-the-counter benefits packaged into their plans, and has been reported to be growing a second office location in the Kansas City area alongside its New York headquarters.