Chapter Raises $75 Million Led by Stripes to Build the Future of Medicare and Retirement Guidance.
NEW YORK – Chapter, the industry-leading Medicare navigation platform, announced today that it raised $75 million in Series D funding led by Stripes, with participation from all major investors: XYZ Venture Capital, Susa Ventures, Addition, Narya Capital, and Maverick Ventures. This raise comes less than one year after Chapter’s Series C and allows the company to run even faster at its mission to deliver better, more personalized Medicare and retirement experiences to Americans. The capital will fuel Chapter’s continued product expansion — all built to ensure seniors have access to the best data and technology for their most consequential decisions. Over the past year, Chapter experienced 4x enrollment growth and continues to build on that momentum through 2025.
“Chapter is reshaping one of the most consequential — and confusing — decisions in someone’s life as they enter retirement: their health coverage.”
Stripes, a firm known for backing consumer, enterprise, and healthcare brands with amazing products, is leading the financing.
“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 be joining Chapter’s Board of Directors. “The Chapter team has taken a fundamentally innovative approach to this complex problem by reimagining the technology and data stack from the ground up in order to deliver far superior guidance to America’s seniors. We are thrilled to support their vision as they expand a platform that’s already made a meaningful difference for so many.”
This fundraise follows a year of accelerated impact, driven by the company’s dedication to high-quality user experiences. Chapter continues to lead the industry with user satisfaction, NPS, and retention of both beneficiaries and enterprise partners.
“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, Co-founder and CEO of Chapter. “At a time when the regulatory environment and Medicare ecosystem is rapidly changing, we remain committed to bringing transparency and trust to a system that desperately needs it.”
In the current economic climate and with increasingly sophisticated scams, retirees seek support and security. Healthcare systems, financial advisors, and content creators are looking for trusted resources to support better health and financial outcomes for their patients, clients, and audiences.
Choosing a Medicare plan is one of the most important decisions retirees face, yet the decision is clouded by deceptive marketing, exploitative agents, and an overall lack of transparency. Chapter has made significant strides in improving the Medicare landscape. By eliminating conflicts of interest between consumers and advisors, Chapter offers the only unbiased Medicare guidance in the country. Through its proprietary technology, Chapter empowers its advisors to deliver high-quality guidance at scale, ensuring retirees receive the best possible support every time.
In the last year, Chapter has rapidly grown its platform and forged key partnerships with the country’s top health systems, financial firms, and content creators—cementing its role as the default Medicare and retirement partner. These moves have powered Chapter’s ability to help tens of thousands more Americans navigate complex decisions with the same high-touch, high-trust experience it’s known for.
Chapter’s influence extends beyond individual enrollments. The company has driven consumer-centric policy changes in Medicare, advocating for greater transparency and alignment of agent incentives with the needs of retirees. These efforts, which include several ongoing initiatives, are creating lasting improvements in the Medicare system and working toward a future in which retirees have the support they deserve.
Chapter continues to serve an increasing number of retirees and has expanded its impact beyond Medicare enrollment. Last year, Chapter launched its Over-the-Counter (OTC) app, which enables Medicare beneficiaries to easily redeem over-the-counter (“OTC”) benefits available through their plans. Many Medicare plans include a host of benefits, but these benefits are often difficult to access. Each year, approximately $5 billion of OTC benefits go unused. Chapter has scaled the user base by 20x and signed partnership agreements with large, national retailers to propel growth and support more seniors.
As Chapter continues to grow, its commitment to retirees remains steadfast. The company is excited to expand its resources and develop new solutions to meet retirees’ most pressing needs, ensuring our aging population receives the care, support, and security they deserve in retirement.
About Chapter
Chapter is the most comprehensive Medicare navigation platform in the United States. Built to empower older Americans with unbiased, personalized guidance, Chapter helps seniors find the best-fitting Medicare coverage by evaluating every plan in every zip code. Learn more at askchapter.org.
About Stripes
Stripes is a New York-based growth equity firm that invests globally in companies with amazing products for consumers and businesses and helps them scale. Since 2008, Stripes has partnered with market-defining companies, providing value-added support to help accelerate growth and build long-term, durable businesses. With an experienced team and trusted network of industry operators and experts, Stripes’ mission is to provide resources and strategic advice that support entrepreneurs at every inflection point across go-to-market, brand building, talent, operations, and more. For more information about Stripes, please visit www.stripes.co.
