The new capital comes less than a year after its Series C and will support Chapter’s ongoing mission to deliver smarter, more personalised Medicare and retirement guidance to millions of Americans.
The funding will be used to expand Chapter’s enterprise partnerships, accelerate product development, and invest in next-generation data and technology infrastructure. The goal: to empower retirees with more proactive, trustworthy support at a time when navigating health coverage has never been more critical.
“Chapter is reshaping one of the most consequential — and confusing — decisions in someone’s life as they enter retirement: their health coverage,” said Ron Shah, Partner at Stripes, who will join Chapter’s Board of Directors. “They’ve built a platform that combines powerful technology with a human touch, fundamentally improving how seniors make these life-altering decisions.”
Chapter’s growth trajectory has been steep. Over the past year, the company has quadrupled its Medicare enrollments and expanded its network of partnerships with leading health systems, financial institutions, and content creators. These collaborations have cemented Chapter’s reputation as a trusted retirement partner for organisations and individuals alike.
“Navigating Medicare is needlessly complex,” said Cobi Blumenfeld-Gantz, Co-founder and CEO of Chapter. “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.”
Chapter distinguishes itself by offering unbiased Medicare guidance, eliminating conflicts of interest between advisors and consumers. Its proprietary technology enables licensed advisors to deliver personalised recommendations at scale, ensuring retirees receive optimal support every time.
The company’s efforts are also driving systemic change. Chapter has advocated for consumer-focused policy reform in Medicare, working to realign incentives and increase transparency throughout the industry. These initiatives, combined with Chapter’s high user satisfaction scores and strong retention rates, highlight its growing influence.
In addition to Medicare enrollment, Chapter has broadened its services. Last year, the company launched an Over-the-Counter (OTC) app that allows Medicare beneficiaries to easily redeem OTC benefits included in their plans — a market where an estimated $5 billion in benefits go unused annually. Chapter has scaled the app’s user base by 20x and secured partnerships with major national retailers to improve access for seniors.
With its latest funding, Chapter is poised to continue reshaping the Medicare and retirement experience for America’s aging population. As Blumenfeld-Gantz emphasised, “This isn’t just about helping people choose a health plan. It’s about ensuring they get the care, support, and peace of mind they deserve in retirement.”
