Chapter launched six years ago as a Medicare navigation and advisory company and has since expanded rapidly, growing to support more than 500,000 enrollees.
But from the beginning, Chapter’s vision was to build a broader platform to help seniors navigate consequential retirement decisions “across health, wealth and purpose,” CEO and co-founder Cobi Blumenfeld-Gantz told Fierce Healthcare.
To support this expansion, Chapter acquired startup Hively, a personalized retirement navigation and membership platform designed to help active older adults transition into and manage their post-career lives. Chapter shared the acquisition news exclusively with Fierce Healthcare.
With Hively's co-founders Angela Gu and Jenn Kim on board, Chapter plans to launch community programming, called Chapter Community, as a space for retirees, offering in-person experiences and online conversations about retirement and aging.
"What they've been working on is very aligned with what we've wanted to build for a long time," Blumenfeld-Gantz said. "From the outset, we've wanted to build this broader platform that helps seniors navigate their health, their wealth and their purpose. Hively, and now Chapter Community, is very much in that purpose bucket, and it just seems like a natural fit."
Hively and Chapter are aligned around a broader goal of helping people navigate retirement, Gu said, but the companies started in different verticals. "It's such an amazing opportunity to join forces. On top of that, for us at Hively, we had figured out an engagement model that was really working, but to be able to join the Chapter team and be able to scale at a much faster pace with the resources that Chapter has was really exciting."
Gu and Kim met as graduate students at Harvard and connected over a shared frustration around their parents' retirement transitions. About 4 million adults reach the traditional retirement age of 65 each year as the U.S. hits the peak of the Baby Boomer generation retirement wave. Each day, approximately 11,400 people turn 65. But many retirees can feel sudden isolation and loss of direction during this transition.
"You go from having this packed calendar, and there's a huge identity and meaning tied to your career, to having an empty calendar, sitting at home every day, and really struggling with this question of 'What's next?' We spent, together, a lot of our two years at grad school talking to hundreds and hundreds of retirees and realizing, 'Wow, our parents are really not alone in this experience,' and there's this massive life transition where people are left to navigate this on their own. And while there's such a focus on the financial readiness of retirement, people really underestimate the emotional, mental parts of this transition," Gu said.
One in three older adults experience loneliness, while one study found that nearly one in three retirees experience depression.
Gu and Kim built Hively to be the "go-to destination" for modern retirement with a focus on fostering relationships and connection. The co-founders say they want to "rewrite the current narrative around retirement," Kim said. "The word itself has negative connotations. We actually don't like calling it retirement. We say 'next chapter'," she said.
Hively was built to be a comprehensive support system for the retirement transition, starting with community. "We built out a group retirement transition curriculum, and had a group experience for people engaged in peer support discussions about this topic, as well as other aging-related topics," Gu said.
Now at Chapter, Gu and Kim will continue building a platform that offers tools, experts, and a peer community to help seniors discover what’s next in this new chapter of their lives.
Tracye Warfield, a founding facilitator with Hively, and now a facilitator at Chapter Community, said, "What I’ve always appreciated about Hively is its understanding that retirement isn’t one-size-fits-all, and that connection and meaningful conversations are essential to exploring what comes next. With Chapter expanding that vision, there’s an exciting opportunity to reach and bring more people together."
Chapter claims it is now the leading Medicare navigation company, and it has quickly built out tools and financial products that support seniors. Chapter's platform helps Medicare enrollees find the right plans for their needs, and the company leans on AI to back its licensed advisers in making recommendations to users. Chapter's backend AI workflows have enabled the company to scale by several multiples every year while keeping corporate headcount nearly flat, according to executives.
Seniors who use Chapter's platforms can also tap into a tool that makes it easier for them to get the most out of over-the-counter benefits offered by their plans. In the past year, the company has also rolled out new tools such as a provider directory and prescription cost calculator, with rising health costs as a backdrop.
The company continues to grow nearly 3x every year for the past four years and is on pace to do so again this year, Blumenfeld-Gantz said.
Across 2025, the company's revenue tripled, and it surpassed $100 million in annual recurring revenue, or ARR, according to executives. In April, Chapter raised a $100 million series E funding round, hitting a $3 billion valuation, according to media reports. Chapter picked up $75 million in series D funding in 2025. The company has raised about an estimated $284 million to date.
U.S. Vice President JD Vance's venture capital firm, Narya Capital, was an early investor in the company, and the company's series E round was led by Generation Investment Management, a sustainable investment firm co-founded by former U.S. Vice President Al Gore.
The company has a unique go-to-market strategy with very little direct-to-consumer advertising, which is the standard default in the Medicare business. The company partners with health systems, financial institutions and content creators to support their patients, clients and audiences as they're navigating Medicare, Blumenfeld-Gantz said.
“We've been able to create a really big and strong network of these partners, which is quite defensible as we think about potential competition in the future,” he said.
About a third of the company’s enrollment volume comes from user referrals, he claimed. “Going through the trusted channel matters so much, and it keeps our cost of acquisition down,” he noted.
With the acquisition of Hively, Chapter is now moving beyond Medicare navigation.
"Our vision with Chapter Community, and the north star that we put out there, is we want to help people make the most of their retirement chapter and we want to become the default community for all retiring Americans where people find meaningful ways to spend their time, but also find other people to spend their time with, so think about in-person experiences as well as online conversations and discussions that focus on the specific transition into retirement, but also other topics around aging at large," Kim said.
Blumenfeld-Gantz expects Chapter to be the largest Medicare navigator in three years, and the company will continue to build out services for seniors. The goal is to evolve Chapter into a one-stop resource for seniors navigating major retirement decisions, from Medicare and Social Security to finances, community and how they spend their time, he said.
The acquisition of Hively also aligns with Chapter's "acquihire" strategy to bring talented executives and startup builders into the company.
As AI advances and software becomes cheaper to build, the barrier to entry for good operators to start companies is lower, Blumenfeld-Gantz noted. "Our talent philosophy has evolved and crystallized a lot. Many of the best people are starting companies as opposed to joining companies. As someone who wants people to join this company, we have to change our strategy. We're focused on finding the best people via acquisitions," he said.
Last week, the company announced it acquired Ridgeway, an applied AI startup. Founder Hamza Mostafa and members of Ridgeway’s engineering team will join Chapter as the company plans to build out additional AI products that serve the needs of retirees.
Chapters invests in building AI tools and automation to improve the user experience for seniors, Blumenfeld-Gantz said. Older Americans are poorly served by the tech industry today, he noted, and seniors are the most skeptical demographic when it comes to AI.
"Seniors likely have the most to gain from this advanced technology, but they're the most distrustful of it today. We are trying to bridge that trust gap," he said.
In a statement, Ridgeway's Mostafa said Chapter has built enormous trust through its accurate and ethical Medicare guidance.