Chapter raises $100 million

Medicare broker Chapter Medicare announced a $100 million Series E round led by Generation Investment Management, with participation from new investors Fifth Down Capital, 8VC, as well as the company’s existing investors: Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures. The company more than doubled its valuation since the prior funding round less than one year ago.

Founded in 2020, the NY-based startup has raised ~$284 million to date. In 2025, the company grew revenue 3x and surpassed $100 million in ARR.

Proceeds from the raise will enable Chapter to accelerate growth and launch additional financial products for seniors.

“Cobi and his team have earned the trust of American seniors by building a data and AI platform that provides accurate information and impartial advice in an industry largely devoid of either. They have rapidly become the premier option for Medicare plan selection and utilization. As our society is gradually transformed by artificial intelligence, Chapter is uniquely positioned to ensure that advances in technology serve the needs of seniors.” – Anthony Woolf, Partner at Generation Investment Management.

“Most technology companies ignore retirees. Our mission is to ensure every senior is able to preserve their health, wealth, and purpose by building products that we wish our own parents had at the outset of retirement. We are the only company that reviews every single Medicare plan nationwide and offers unbiased guidance, and we are rapidly building additional products that will empower seniors to author the next chapter of their lives.” – Cobi Blumenfeld-Gantz, CEO and Co-Founder of Chapter.