Chapter, an AI-driven Medicare navigation platform, has raised $100 million in a Series E funding round led by Generation Investment Management, with participation from new investors Fifth Down Capital and 8VC, alongside existing backers including Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures. The company said its valuation has more than doubled since its previous round less than a year ago, reflecting strong investor confidence in its approach to simplifying Medicare decisions.
Chapter focuses on a complex and often confusing problem for older Americans: navigating Medicare. Rather than acting as a traditional marketplace or promoting specific plans, the platform reviews all available options nationwide and provides guidance that is not tied to insurers or commission structures. This approach aims to help retirees avoid costly mistakes and maintain access to preferred providers in a system that changes annually and can be difficult to understand.
The company combines AI with licensed advisors, giving them access to a comprehensive data layer to deliver personalised recommendations at scale. Users can also interact directly with the platform to compare plans, analyse prescription costs and understand their coverage. Chapter has also developed tools such as a detailed provider directory and prescription cost calculator to support more informed decision-making.
With the new funding, Chapter plans to expand beyond Medicare into broader financial services for retirees, positioning itself as a central platform for managing both healthcare and financial decisions in retirement. The strategy reflects the growing overlap between health and financial planning as people age, with the company aiming to become a long-term resource for reducing overall costs and improving outcomes.
Founded by Cobi Blumenfeld-Gantz, Chapter has seen rapid growth, tripling revenue in 2025 and surpassing $100 million in annual recurring revenue while maintaining stable headcount. The company also partners with organisations that serve older populations, acting as a concierge-style resource to guide seniors through critical decisions during retirement.
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