Chapter

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.

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 & Analytics

Consumer Software

AI & Machine Learning

Healthcare

Company Size

201-500

Company Stage

Series E

Total Funding

$301M

Headquarters

New York City, New York

Founded

2020

Simplify Jobs

Simplify's Take

What believers are saying

  • Tripled revenue in 2025, hit $100M ARR with flat headcount.
  • Raised $100M Series E at $3B valuation in April 2026.
  • Expanded partnerships with Mesa View, Three Rivers hospitals in October 2025.

What critics are saying

  • CMS revokes licenses within 12 months over commission conflicts.
  • UnitedHealth cuts commissions 30% in 12 months, erasing profitability.
  • Hospital partners like Barstow terminate ties in 12 months from steering complaints.

What makes Chapter unique

  • Proprietary AI scans every Medicare Advantage, Medigap, and Part D plan nationwide.
  • Incentivizes advisors on customer satisfaction, not plan commissions.
  • Combines algorithmic matching with licensed human advisors for unbiased recommendations.

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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
Stripe
$250M
Reddit
$1.3B
Epic Games
$1.5B
Airbnb

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

-4%

1 year growth

0%

2 year growth

1%
Just AI News
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.

Mesa View Regional Hospital
Oct 10th, 2025
Mesa View Regional Hospital Collaborates with Chapter to Provide Free Support During Medicare Enrollment

Mesa View Regional Hospital collaborates with Chapter to provide free support during Medicare Enrollment. Medicare Guidance Available for Local Seniors Mesquite, NV (October 10, 2025) - As more local residents become eligible for Medicare this year, Mesa View Regional Hospital is committed to helping patients have the resources needed to transition smoothly from their current health plans. "Navigating Medicare can be challenging," said Kelly Adams, CEO of Mesa View Regional Hospital. "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 Mesa View Regional Hospital, regardless of which Medicare plan you choose." To support patients during this important transition, Mesa View Regional Hospital 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 Mesa View Regional Hospital. * 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 833-202-4941 or visiting MedicareMesa.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). Additional information is available at Medicare.gov or by calling 800-MEDICARE. If you are a current Mesa View Regional Hospital patient and your Medicare health plan is not listed as in-network, it is especially important to review alternate options as soon as possible. About Mesa View Regional Hospital Mesa View Regional Hospital is a 25-bed facility located in Mesquite, Nevada with skilled professional staff that offers award-winning quality and patient - focused healthcare. Mesa View provides a full range of inpatient and outpatient hospital services including an Intensive Care Unit, Medical, Surgical, Infusion Therapy, Orthopedics - Total Joint and Sports Medicine Program, Women's Health, Laboratory, Cardiopulmonary Testing, Imaging and Emergency Medicine Services. For more information, visit www.MesaViewHospital.com

Three Rivers Medical Center
Oct 10th, 2025
Three Rivers Medical Center Collaborates with Chapter to Provide Free Support During Medicare Enrollment

Three Rivers Medical Center collaborates with Chapter to provide free support during Medicare Enrollment. Medicare Guidance Available for Local Seniors Louisa, KY (October 10, 2025) - As more local residents become eligible for Medicare this year, Three Rivers 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 Greg Kiser, CEO of Three Rivers 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 Three Rivers Medical Center, regardless of which Medicare plan you choose." To support patients during this important transition, Three Rivers 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 Three Rivers 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 833-202-4941 or visiting MedicareThreeRivers.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). Additional information is available at Medicare.gov or by calling 800-MEDICARE. If you are a current Three Rivers Medical Center patient and your Medicare health plan is not listed as in-network, it is especially important to review alternate options as soon as possible.

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