• Chapter has rapidly become the leading Medicare navigation platform nationwide
• Its AI-native system powers unbiased guidance and white-glove support for one of the most consequential decisions in retirement
• Proceeds from the raise will enable Chapter to accelerate growth and launch additional financial products that improve the lives of seniors, the demographic most underserved by technology companies today

NEW YORK–(BUSINESS WIRE)–Chapter, the leading AI company focused on retirement, announced today that it has raised $100 million in Series E funding.

“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.”Share

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 significant year for Chapter. The company grew revenue 3x and surpassed $100 million in ARR, making it one of the fastest-growing companies in the country. More importantly, the company maintained its mission-focused culture and commitment to excellence in hiring, with corporate headcount remaining flat year over year.

Chapter also deployed significant new products including the most accurate provider directory and prescription cost calculator for Medicare in the country. Through its platform, Chapter is expanding to help its members save money on all their spend, not just Medicare.

About Chapter

Chapter offers the leading Medicare navigation platform in the United States, helping older Americans choose the right healthcare coverage with confidence. Its AI-native platform enables its licensed advisors to deliver personalized, unbiased recommendations. Its platform also enables seniors to get the most out of their benefits.

Chapter partners with leading organizations nationwide to assist the seniors they serve with one of the most important decisions in retirement. Learn more at askchapte r.org.

About Generation Investment Management

Generation Investment Management LLP is an independent, private, owner-managed partnership headquartered in London, with a US presence in San Francisco. Since its founding in 2004, Generation has played a pioneering role in the development of sustainable investing. Its vision is a sustainable world in which prosperity is shared broadly, in a society that achieves wellbeing for all, protects nature and preserves a habitable climate. Generation pursues its vision with urgency by seeking to deliver long-term, attractive, risk-adjusted investment returns and positive impact, and by advocating for the adoption of sustainable investing across the wider market.

Contacts

For media inquiries, contact:
Paul Davis
press@askchapter.org

(c)2026 Business Wire, Inc., All rights reserved.