Chapter is a Medicare navigation company that helps older Americans choose health coverage and manage healthcare and retirement decisions. Founded in 2020 by Cobi Blumenfeld-Gantz, the company combines licensed human advisors with an AI-native platform to simplify what is widely regarded as a confusing decision space, with thousands of Medicare plans available nationwide. Chapter's stated mission is to build a trusted layer between seniors and increasingly complex technology.
The platform uses proprietary algorithms to analyze the full landscape of Medicare plans available across the United States and to identify options that fit an individual's health needs and budget. Chapter emphasizes personalized, unbiased recommendations delivered by licensed advisors who are supported by AI, positioning it as an alternative to brokers who may be steered by commission incentives toward particular plans.
Chapter has reported strong commercial momentum, including tripling revenue in 2025 and surpassing $100 million in annual recurring revenue while keeping headcount relatively stable, which the company and investors have cited as a sign of AI-driven operating leverage. The company is also expanding beyond Medicare into broader financial products for retirees.
In April 2026, Chapter raised a $100 million Series E round at a roughly $3 billion valuation, led by Generation Investment Management with participation from new investors Fifth Down Capital and 8VC alongside existing backers including Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures. The valuation more than doubled from the prior round less than a year earlier.
Prospective users should understand that Chapter is a U.S.-focused service for Medicare-eligible individuals and their families, and that plan recommendations depend on accurate personal health and budget information. As with any insurance navigation service, individuals should review recommended plans carefully and confirm coverage details before enrolling.