Chapter Secures US$100m to Scale AI Medicare Platform

Chapter, a leading AI-native retirement platform, has announced a US$100m Series E funding round as it seeks to redefine how American seniors navigate the complexities of Medicare. 

The capital injection was led by Generation Investment Management, with contributions from new backers Fifth Down Capital and 8VC. Existing investors including Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa

Ventures and Maverick Ventures also participating in the round.

The funding comes at a time of rapid expansion for the company, which has seen its valuation more than double since its previous investment round less than 12 months ago.  

Cobi Blumenfeld-Gantz, CEO and Co-Founder of Chapter, says: “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.”

By focusing on data integrity and unbiased advice, Chapter is positioning itself as a critical intermediary in a Medicare market often criticised for its lack of transparency.

Challenging the status quo in Medicare

The Medicare landscape can be difficult to navigate, with thousands of plan variations and fluctuating costs.

Chapter’s platform distinguishes itself by reviewing every Medicare plan available across the US. 

This comprehensive approach allows its licensed advisors to provide tailored recommendations that are not skewed by the commission structures that often influence traditional brokers.

“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,” says Anthony Woolf, Partner at Generation Investment Management.

“They have rapidly become the premier option for Medicare plan selection and utilisation.

“As our society is gradually transformed by AI, Chapter is uniquely positioned to ensure that advances in technology serve the needs of seniors.”

The firm's ability to harness AI to serve an often-overlooked demographic is a primary driver of its recent success.

The platform’s proprietary technology aims to remove the guesswork from healthcare coverage, ensuring that retirees do not overpay for plans that fail to meet their medical requirements.

Rapid growth and operational efficiency

The financial results for 2025 underscore the speed at which Chapter is capturing market share.

The company reported a threefold increase in revenue over the last year, surpassing US$100m in annual recurring revenue (ARR).

Despite this aggressive financial trajectory, the firm has maintained a flat corporate headcount, highlighting the scalability of its AI-driven model.

Beyond simple plan selection, Chapter has introduced tools designed to solve specific pain points for retirees. 

These include a highly accurate provider directory and a prescription cost calculator, both of which are integrated into the core platform to help members manage their total healthcare spend.