Chapter, a US-based Medicare navigation platform, has closed a $75m Series D funding round to bolster its mission of transforming retirement healthcare experiences.
The round was led by Stripes, with continued backing from existing investors including XYZ Venture Capital, Susa Ventures, Addition, Narya Capital, and Maverick Ventures. The latest investment arrives less than a year after Chapter’s Series C round, according to InsurTech Insights.
Chapter helps Americans navigate the complexities of Medicare by offering transparent, personalised guidance through a combination of advanced technology and licensed human advisors.
The platform eliminates traditional conflicts of interest that often arise in Medicare plan recommendations, ensuring that retirees receive the best options based on their actual needs.
With the fresh capital, the firm plans to deepen its enterprise partnerships, ramp up product development, and invest in cutting-edge data and infrastructure to scale its services.
The company aims to better support retirees at a critical life stage where navigating health coverage can be overwhelming and often misleading.
In recent months, Chapter has seen rapid growth, having quadrupled its Medicare enrolments and expanded partnerships across health systems, financial institutions, and digital content platforms.
It has also broadened its offerings to include a mobile app for Over-the-Counter (OTC) benefits, helping Medicare users redeem unused benefits—a market worth an estimated $5bn. The OTC app has grown its user base twentyfold and now includes partnerships with major national retailers.
Stripes partner Ron Shah, who will join Chapter’s board, said, “Chapter is reshaping one of the most consequential — and confusing — decisions in someone’s life as they enter retirement: their health coverage. They’ve built a platform that combines powerful technology with a human touch, fundamentally improving how seniors make these life-altering decisions.”
Chapter CEO and co-founder Cobi Blumenfeld-Gantz added, “Navigating Medicare is needlessly complex. Too many people end up with plans that cost more and cover less than they should. We’re committed to restoring transparency and trust in a system that desperately needs it — especially now, as scams and misinformation are on the rise.”
The company has also made a mark beyond consumer services, pushing for policy reforms aimed at transparency and better alignment of incentives in the Medicare system. These efforts, along with high user satisfaction and retention, reinforce Chapter’s role as a trusted partner in the retirement journey.
Chapter’s previous Series C funding round was completed less than a year ago, underscoring the momentum behind the firm’s vision and its growing influence in the FinTech space.
Copyright © 2025 InsurTech Analyst
