Chapter, an AI company focused on retirement services, has raised $100 mn in a Series E round led by Generation Investment Management. The company has more than doubled its valuation since its previous funding less than a year ago.
The round included new investors Fifth Down Capital and 8VC. Existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures also participated.
Investor demand reflects continued interest in platforms built for the US ageing population.
Anthony Woolf, partner at Generation Investment Management, said Chapter has built trust with seniors through a data-driven platform that delivers accurate information and impartial advice.
He said the company has quickly become a leading option for Medicare plan selection and usage, and is well placed to apply AI systems to support retirees as technology adoption increases.
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
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,” said Anthony Woolf.
Chief executive and co-founder Cobi Blumenfeld-Gantz said most technology companies overlook retirees. He said Chapter is building products aimed at helping seniors manage health, finances, and long-term planning.
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
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,” said Cobi Blumenfeld-Gantz.
He added the platform reviews every Medicare plan nationwide and provides unbiased recommendations, while new products are being developed to support broader financial decisions in retirement.
Chapter reported strong growth through 2025. Revenue increased threefold and the company exceeded $100 mn in annual recurring revenue.
Headcount remained flat over the same period, pointing to operational efficiency as the business scaled.
The company has also expanded its product set. It launched a provider directory and a prescription cost calculator for Medicare users, both aimed at improving cost visibility and decision-making. Chapter is extending its platform to help members manage spending beyond healthcare coverage.
Chapter operates a Medicare navigation platform in the US, where licensed advisors use its AI system to deliver personalised recommendations.
The platform is designed to help seniors select coverage and manage benefits more effectively. The company also works with organisations across the country to support retirees in making healthcare and financial decisions.
