NEW YORK — Chapter, an AI company focused on retirement, has raised $100 million in Series E funding.
The round was 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 has more than doubled in valuation since its prior funding round less than one year ago.
“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,” said Anthony Woolf, Partner at Generation Investment Management. “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.”
“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,” said Cobi Blumenfeld-Gantz, CEO and Co-Founder of Chapter. “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.”
2025 was a strong year for Chapter. The company said it grew revenue 3x and surpassed $100 million in annual recurring revenue (ARR), making it one of the fastest-growing companies in the country. The company has 100 employees and says corporate headcount remained flat year over year.
