Chapter provides free expert advice and a proprietary search engine to compare all Medicare options in the U.S. including Medicare Advantage, Medigap, and Part D. It uses data integration and algorithms to filter plan choices, then pairs automated recommendations with licensed human support and a digital dashboard for tracking benefits and open enrollment alerts. The company earns commissions from carriers when a user enrolls through the platform, but aligns advisor incentives with customer satisfaction to maintain independence. Its goal is to simplify Medicare decisions for retirees by reducing choice overload and preventing enrollment mistakes.
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Industries
Company Size
201-500
Company Stage
Series E
Total Funding
$301M
Headquarters
New York City, New York
Founded
2020
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Total Funding
$301M
Meets
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Funded Over
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Fed Holds Rates; Chapter Acquires Hively; AI Stocks slip. The Fed holds rates with little guidance, AI earnings disappoint, and Medicare nav startup Chapter acquires retirement platform Hively. Full roundup. October 29, 2026 Healthcare practice & business deals. One notable acquisition surfaced this week in the healthcare services space, while the broader candidate pool leaned heavily toward policy, pharma, and digital-health commentary with no qualifying practice sales. Chapter Acquires Hively. Medicare navigation startup Chapter is expanding beyond insurance guidance with the acquisition of Hively, a personalized retirement navigation and membership platform. Chapter is positioning the combined company as a one-stop shop for older Americans managing retirement. Neither the deal value nor the closing date was disclosed in available reporting. Beyond that transaction, this week's healthcare news centered on policy disputes and earnings rather than practice-level M&A. Eli Lilly's 340B data-sharing policy drew a cease-and-desist letter from Missouri's attorney general and new lawsuits from hospitals. CVS sued to prevent what it characterized as a $2 billion Medicare Advantage star-ratings penalty. Meanwhile, HCA reported roughly $950 million in pretax earnings losses this year, attributed to ACA coverage attrition driving up uncompensated care costs. None of these items involve the sale or acquisition of a small or medium healthcare practice. Global markets & macro. Several major macro forces converged this week, led by a Federal Reserve decision, a wave of disappointing tech earnings, and renewed fiscal debate in the United Kingdom. Fed Holds Rates, Offers Little Guidance. The Federal Reserve kept borrowing costs steady and provided few clues on its next move. Markets reacted cautiously, with gold dipping near $4,000. The decision left open the possibility of a rate hike before year-end, adding uncertainty for interest-rate-sensitive assets and borrowers alike. AI Earnings Disappoint; Tech Stocks Fall. Nasdaq futures slid after weak results from two major technology companies revived questions about AI spending returns. Google parent Alphabet saw its shares tumble roughly 10% after a $51 billion AI capital outlay deepened cash burn. The company acknowledged its "AI mode" has hurt traditional search revenue, and both sales and profits fell short of expectations. Microsoft also reported capital expenditure below analyst forecasts. The Nasdaq 100 was set to open about 1% lower. Meanwhile, global bond sales hit an all-time high, fueled in part by heavy borrowing from large technology companies investing in AI infrastructure. Amazon in Focus. With more than half of its post-earnings gains from the prior quarter erased, Amazon faces pressure to deliver strong cloud growth in its upcoming results. Investors are watching AWS revenue closely as the bellwether for whether AI infrastructure spending is translating into real demand. UK Budget: Time Bought, Hard Choices Deferred. UK Chancellor Healey defended the government's budget package amid growing economic warnings. The Institute for Fiscal Studies said Healey will face significant pressure to find additional funding next year. Commentators broadly characterized the budget as buying time without resolving long-term fiscal and growth challenges. ECB Leadership Change. Christine Lagarde announced she will step down as European Central Bank president in February, roughly eight months before her term was scheduled to end in October 2027. The early departure adds a leadership transition to an already complex macro environment in the eurozone. Geopolitics: US-Iran Diplomacy. Vice President Vance sent a letter to a senior Iranian national security official stressing that any renewed negotiations must address Iran's nuclear program. The outreach is the most senior US-to-Iran contact in several months and comes as President Trump considers resuming military operations after the midterm elections. Iran has conditioned talks on the US lifting its naval blockade and releasing frozen funds. The standoff continues to carry implications for oil markets and regional stability. What to watch. Amazon's earnings report is the immediate test for AI optimism - strong cloud numbers could stabilize tech sentiment, while another disappointment may extend the Nasdaq selloff. The Fed's rate-hold-with-no-guidance posture keeps the path of borrowing costs murky, a direct concern for practice buyers and sellers relying on debt financing. On the deal front, Chapter's acquisition of Hively signals that retirement-adjacent healthcare services remain an active area for platform building. Watch for more Medicare navigation and senior-care consolidation as private capital continues to seek recurring-revenue healthcare models heading into year-end. Explore Tenet M&A. Tenet M&A helps physicians and practice owners navigate healthcare M&A. Start here: Editorial note, image use & corrections. This report is compiled and summarized from publicly available news sources; figures and details should be independently verified. Accompanying images are used under Creative Commons or public-domain licenses (sourced via Openverse) and credited where required. If you believe any content - written or image - has been used in error, is inaccurate, or infringes your rights, or you wish to request a correction or removal, please contact Tenetma Report at [email protected] and Tenetma Report will address it promptly. What do these market moves mean for your practice value? Get a confidential read on what your practice is worth in today's market. About Tenet Mergers & Acquisitions Tenet Mergers & Acquisitions is a sell-side advisory firm for healthcare practice owners exploring a sale, partnership or transition. Thinking about selling your medical practice? Get a confidential practice valuation. If you're considering selling your practice - or exploring your options - a confidential valuation is a helpful first step. Understanding market conditions and potential value provides clarity and supports better decisions around timing and strategy.
Chapter, a Medicare navigation company, has acquired Hively, a retirement navigation and membership startup. Chapter wants to become a one-stop resource for seniors facing major retirement decisions, from Medicare and Social Security to finances and community. Hively co-founders Angela Gu and Jenn Kim will join Chapter to launch Chapter Community. It will offer in-person events and online conversations about retirement and aging. Chapter supports more than 500,000 enrollees. Its revenue tripled in 2025, and it passed $100 million in annual recurring revenue. In April, it raised a $100 million series E round at a reported $3 billion valuation. Last week, Chapter also acquired AI startup Ridgeway. Chief executive officer Cobi Blumenfeld-Gantz said acquisitions are now the company's main way to find top talent.
Chapter acquires Ridgeway to expand leadership position in AI and transform retirement for american seniors. 6:00 am, PT, October 22, 2026 * Chapter is the leading provider of unbiased Medicare guidance nationwide * This acquisition will enable Chapter to continue providing the most accurate Medicare guidance and will assist in building other applied AI products to support consequential decisions in retirement NEW YORK-(BUSINESS WIRE)-October 22, 2026- Chapter, the leading provider of unbiased Medicare guidance for seniors, announced today that it has acquired Ridgeway, an applied AI startup founded by Hamza Mostafa. Mr. Mostafa and members of Ridgeway's engineering team will join Chapter to build AI products that serve the needs of retirees. Hamza Mostafa "Hamza and his team are exceptional, and we need the very best engineers to keep building the very best products for seniors," said Cobi Blumenfeld-Gantz, CEO and Co-Founder of Chapter. "Older Americans are poorly served by the tech industry today, but we're committed to changing that." Chapter currently uses AI to ensure that its advisors ask the right questions and surface the right answers for seniors seeking Medicare guidance. Its backend AI workflows have enabled the company to scale by several multiples every year while keeping corporate headcount nearly flat. "Seniors are the most skeptical demographic when it comes to AI, but they also have the most to gain from advances in technology," said Mostafa. "Chapter has built enormous trust through its accurate and ethical Medicare guidance and I'm excited to build additional product offerings that serve the needs of our elders." Prior to founding Ridgeway, Mostafa built and evaluated frontier agent systems, including ChatGPT Agent and ChatGPT Deep Research, at OpenAI. Ridgeway previously raised $2.8 million in venture funding from Emergence Capital and Susa Ventures. About Chapter Chapter offers the leading Medicare navigation platform in the United States, helping older Americans choose the right healthcare coverage with confidence. Its AI-native platform enables its licensed advisors to deliver personalized, unbiased recommendations. Chapter partners with leading organizations nationwide to assist the seniors they serve with one of the most important decisions in retirement. Learn more at chapter.com.
Leading Resource for Medicare, Chapter Announces $17 Million Series A Round, led by Narya Capital and Peter Thiel
Big Bend Regional Medical Center collaborates with Chapter to provide free support during Medicare Enrollment. Medicare Guidance Available for Local Seniors Alpine, TX (August 31, 2026) - As more local residents become eligible for Medicare this year, Big Bend Regional Medical Center is committed to helping patients have the resources needed to transition smoothly from their current health plans. "Navigating Medicare can be challenging," said Wendy Barnett, CEO of Big Bend Regional Medical Center. "There are many factors to consider when selecting a healthcare plan. We're committed to helping you continue to receive the quality care you expect from Big Bend Regional Medical Center, regardless of which Medicare plan you choose." To support patients during this important transition, Big Bend Regional Medical Center has partnered with Chapter, a team of licensed independent Medicare advisors, to provide free, personalized guidance. * Discover Savings - Advisors compare plans to help patients find affordable options that cover prescriptions and doctor visits. * Access the Care You Deserve - Advisors help select coverage that allows patients to continue receiving compassionate, quality care from Big Bend Regional Medical Center. * Your Medicare Questions, Answered - From plan options to coverage details, Chapter's advisors take the time to answer your questions and help you get the care you need in-network. Local residents can contact Chapter by calling 740-570-4095 or visiting MedicareBigBend.com for assistance. Key Medicare Dates * Medicare Open Enrollment: October 15 - December 7 * Change coverage for the following year, with new coverage beginning January 1. * Medicare Advantage Open Enrollment: January 1 - March 31 * Switch Medicare Advantage plans or return to Original Medicare (prescription drug plan changes not included).
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Industries
Company Size
201-500
Company Stage
Series E
Total Funding
$301M
Headquarters
New York City, New York
Founded
2020
Find jobs on Simplify and start your career today
We update Chapter's jobs every few hours, so check again soon!Browse all jobs