Chapter has raised $75 million in Series D funding, marking another milestone in its mission to improve Medicare and retirement planning for seniors across the U.S. The round was led by Stripes, with ongoing support from XYZ Venture Capital, Susa Ventures, Addition, Narya Capital, and Maverick Ventures.
The raise follows Chapter’s Series C less than a year ago and reinforces growing investor confidence in its platform. Stripes partner Ron Shah will join Chapter’s board as part of the investment.
Chapter operates in a healthcare space that often overwhelms retirees with confusing policies, deceptive marketing, and limited transparency. Medicare, in particular, is a system many struggle to navigate, and Chapter aims to change that.
“Navigating Medicare is needlessly complex. Too many people end up with plans that cost more and cover less than they should,” said Cobi Blumenfeld-Gantz, Chapter’s Co-founder and CEO. “We remain committed to bringing transparency and trust to a system that desperately needs it.”
As retirees face an evolving regulatory environment and increasing financial scams, Chapter’s role as a trusted partner for healthcare systems, financial advisors, and influencers has become more critical. The company’s unbiased approach and strong satisfaction ratings set it apart.
With the new capital, Chapter plans to deepen its partnerships with healthcare providers and financial institutions, expand its product offering, and scale its technology infrastructure. These investments will power more proactive and personalized support for Medicare-eligible individuals.
Chapter also plans to build on its recent success with the Over-the-Counter (OTC) app, which helps retirees redeem unused benefits. The app saw 20x growth last year, addressing a $5 billion gap in unclaimed OTC benefits.
Over the past year, Chapter experienced a fourfold increase in enrollments and forged new partnerships with national health systems, financial firms, and content creators. These collaborations have helped tens of thousands more Americans make informed decisions about their healthcare.
Beyond its core services, Chapter has advocated for consumer-first policy changes, promoting better alignment of agent incentives with retiree needs. The company sees this as essential to creating lasting improvements in the Medicare system.
Founded to eliminate conflicts of interest in Medicare advising, Chapter has developed proprietary technology to support advisors in offering consistent, high-quality recommendations. Its end-to-end platform analyzes every plan in every zip code to ensure optimal choices for users.
The team continues to focus on delivering a high-touch, high-trust experience that scales, while staying true to its mission of improving outcomes for America’s aging population.
The Series D round saw participation from all of Chapter’s major existing investors, including:
“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 of Stripes. “We are thrilled to support their vision as they expand a platform that’s already made a meaningful difference for so many.”
