C

Chapter

Independent advisory for Medicare options enrollment

Overview

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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About Chapter

Simplify's Rating
Why Chapter is rated
B
Rated B on Competitive Edge
Rated A on Growth Potential
Rated C on Differentiation

Industries

Data & AnalyticsConsumer SoftwareAI & Machine LearningHealthcare

Company Size

201-500

Company Stage

Series E

Total Funding

$301M

Headquarters

New York City, New York

Founded

2020

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Simplify's Take

What believers are saying

  • Chapter raised $100 million in April 2026 at a $3 billion valuation.
  • Revenue tripled in 2025, and ARR crossed $100 million while headcount stayed flat.
  • GoodRx partnership and hospital affiliates like Big Bend expanded Chapter's patient acquisition funnel.

What critics are saying

  • CMS capped 2026 MA initial commissions at $694, compressing Chapter's economics.
  • Medicare marketing rules tightened in 2026; every enrollment script now faces compliance scrutiny.
  • Humana and UnitedHealthcare dominate MA distribution; a carrier-led direct model can bypass Chapter entirely.

What makes Chapter unique

  • Chapter scans every Medicare plan nationwide, not just carrier-sponsored options.
  • Its advisors are independent, with recommendations tied to satisfaction, not plan economics.
  • Chapter added provider directories and prescription calculators in 2026, tightening plan-to-care matching.

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Funding

Total Funding

$301M

Meets

Industry Average

Funded Over

6 Rounds

Series E funding typically includes additional rounds after Series D if the company needs more capital. The business is usually stable, and these rounds are typically used for further expansion or to address market challenges.
Series E Funding Comparison
Meet Average

Industry standards

$100M
$245M
$250M
$1.3B
$1.5B

Benefits

Flexibility to work remotely

Competitive compensation package

Unlimited PTO

Breakfast, snacks, & coffee/tea on us.

Growth & Insights and Company News

Headcount

6 month growth

↑ 1%

1 year growth

↑ 0%

2 year growth

↓ -2%
Business Wire
Sep 17th, 2026
Chapter Announces $17 Million Series A Round, led by Narya Capital and Peter Thiel with participation from existing investors Maverick Ventures, Susa Ventures, and XYZ Venture Capital

Leading Resource for Medicare, Chapter Announces $17 Million Series A Round, led by Narya Capital and Peter Thiel

Big Bend Healthcare
Aug 31st, 2026
Big Bend Regional Medical Center collaborates with Chapter to provide free support during Medicare Enrollment.

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).

Genaro Palma Consulting EOOD
Apr 10th, 2026
Chapter raises $100M Series E for Medicare AI.

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

Business Wire
Apr 10th, 2026
Chapter Raises $100 Million Series E to Continue Building the Trust Layer Between Seniors and Technology in the Age of AI

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...

Pulse 2.0
Apr 9th, 2026
Chapter raises $100M at $3B valuation to expand AI-driven Medicare navigation platform

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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