Chapter, a NYC-based provider of a Medicare navigation platform, has raised $100 million in a Series E funding round led by Generation Investment Management.
The round also saw participation from Fifth Down Capital, 8VC, Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures.
The company plans to use the funds to grow faster and introduce new financial products.
2025 was an important year for the Chapter. The company tripled its revenue and passed $100 million in annual recurring revenue, becoming one of the fastest-growing companies in the country. At the same time, it kept its strong mission-driven culture and high hiring standards, with no increase in corporate staff.
Chapter also launched major new products, including a highly accurate provider directory and a prescription cost calculator for Medicare. With its platform, the company is now helping members save money on more than just Medicare—it’s expanding to cover all their spending.
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“Cobi and his team have earned the trust of American seniors by building a data and AI platform that gives clear, accurate information and unbiased advice—something rare in this industry,” said Anthony Woolf, Partner at Generation Investment Management. “They’ve quickly become a top choice for choosing and using Medicare plans. As AI continues to shape our world, Chapter is well placed to make sure seniors benefit from these advances.”
“Most tech companies overlook retirees. Our mission is to help every senior protect their health, money, and sense of purpose by creating the kind of products we’d want for our own parents,” said Cobi Blumenfeld-Gantz, CEO and Co-Founder of Chapter. “We’re the only company that reviews every Medicare plan in the country and gives unbiased guidance. We’re also building new products to help seniors take control of the next stage of their lives.”
About Chapter
Founded in 2020 by Cobi B., Chapter is a leading Medicare navigation platform in the United States that helps older Americans choose the right healthcare coverage with confidence. Its AI-powered platform supports licensed advisors in giving personalized and unbiased recommendations, while also helping seniors make the most of their benefits. Chapter works with leading organizations across the country to support seniors in making one of the most important decisions of their retirement.
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