Chapter provides an independent Medicare enrollment advisory service that uses a proprietary search to compare all US Medicare options, including Medicare Advantage, Medigap, and Part D. It combines data integration and algorithmic matching to filter thousands of plan options and align coverage with a user’s doctors, prescriptions, and budget, supported by a digital dashboard and automated alerts plus licensed human support. The company earns commissions when a user enrolls through its platform, but its incentives are tied to customer satisfaction rather than the specific plan chosen. Its goal is to simplify retirement health coverage decisions and reduce enrollment errors by delivering clear recommendations and ongoing support.
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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
6 Rounds
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Flexibility to work remotely
Competitive compensation package
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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).
Chapter raises $100M Series E for Medicare AI. Key Points * Chapter raised $100M in Series E funding led by Generation Investment Management, with Fifth Down Capital, 8VC, and existing investors Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, and Maverick Ventures participating. * The company tripled revenue in 2025 and crossed $100M in ARR, making it one of the fastest-growing platforms in the US retirement technology sector. * Chapter plans to expand from Medicare navigation into broader financial products for seniors, using AI and licensed advisors to serve one of the most underserved demographics in tech. April 10, 2026 Credit: BUSINESS WIRE
Chapter, the leading AI company focused on retirement, announced today that it has raised $100 million in Series E funding. This press release features multi...
Chapter, an AI-driven Medicare navigation platform, has raised $100 million in a Series E round led by Generation Investment Management, valuing the company at $3 billion. Fifth Down Capital, 8VC and existing investors including Stripes and XYZ Venture Capital participated. The company has more than doubled its valuation since its previous funding round less than a year ago. Chapter achieved $100 million in annual recurring revenue in 2.5 years whilst tripling revenue in 2025 and maintaining flat headcount. Chapter reviews every Medicare plan nationwide, combining AI technology with licensed advisors to provide unbiased recommendations for seniors. The funding will support expansion into additional financial products aimed at retirees' health, wealth and wellbeing. The company recently launched tools including a provider directory and prescription cost calculator.
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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