Chapter, an AI-driven Medicare navigation platform focused on retirement, announced it has raised $100 million in a Series E funding round at a $3 bill valuation led by Generation Investment Management, with participation from Fifth Down Capital, 8VC, and existing investors including Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures.
Chapter Chief Evangelist Paul Davis told me that in 2025, the company reported significant growth, tripling revenue and surpassing $100 million in annual recurring revenue, while maintaining a disciplined hiring approach with flat headcount year over year. It is also worth noting that Al Gore – whose fund led the round – is the second VP to invest in Chapter, following JD Vance, who was an early investor.
The company has more than doubled its valuation since its previous funding round less than a year ago, underscoring strong investor confidence in its approach to improving how seniors navigate healthcare and financial decisions.
Chapter has rapidly emerged as a leading platform for Medicare guidance in the U.S., leveraging an AI-native system to provide unbiased recommendations and personalized support. The company reviews every Medicare plan nationwide and pairs its technology with licensed advisors to help seniors make informed decisions about their coverage.
The new funding will be used to accelerate growth and expand into additional financial products aimed at improving the health, wealth, and overall well-being of retirees, a demographic the company believes is underserved by most technology providers.
The company also launched new tools, including an advanced provider directory and a prescription cost calculator, and is expanding its platform to help members save across broader categories beyond Medicare.
Chapter continues to partner with organizations nationwide to support seniors in making critical retirement decisions, positioning itself as a key player at the intersection of artificial intelligence, healthcare, and personal finance.
KEY QUOTES:
“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
