Chapter, a Medicare-navigation platform, raised a $100 million Series E led by Generation Investment Management, with new investors Fifth Down Capital and 8VC joining alongside existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures. The company says it has more than doubled its valuation since its last round, which closed less than a year earlier.
Chapter's model is built around trust: rather than acting as a marketplace pushing specific plans, it reviews all available Medicare options nationwide and gives guidance not tied to insurer commissions. The company says it tripled revenue in 2025 and crossed $100 million in annual recurring revenue while keeping headcount flat -- an efficiency profile investors increasingly prize.
“The raise underscores appetite for vertical AI aimed at trust-heavy, underserved consumer markets.”
The raise underscores appetite for vertical AI aimed at trust-heavy, underserved consumer markets. Seniors navigating Medicare face a genuinely confusing decision with major financial consequences, and a platform that combines AI with conflict-free advice is positioned in a large, durable market that mainstream tech has largely overlooked.