Chapter
12 known investors
Chapter provides Medicare plan comparison and advisory services to help seniors choose the best health insurance coverage. The platform connects retirees with advisors who evaluate nationwide Medicare plans and recommend personalized options based on individual needs.
Also known as Chapter Medicare
Founders & leadership
Investors · 12
Also in the syndicate · 2
Funding
SEC filings, press & company announcements$100M disclosed across 1 of 3 rounds · 2022–2026
- Undisclosed amountSeries EJun 2026 · 2 sources
Generation Investment Management (lead), 8VC, Addition, Fifth Down Capital, Maverick Ventures, Narya Capital, Stripes, Susa Ventures, XYZ Venture Capital
Source ↗ - $100MSeries EApr 2026 · 3 sources
Generation Investment Management (lead), 8VC, Addition, Fifth Down Capital, Maverick Ventures, Narya Capital, Stripes, Susa Ventures, XYZ Venture Capital
Source ↗
Source: company announcements and press reports — follow each round's link for the claim.
Company profile
researched Aug 2026Chapter operates a Medicare navigation and advisory platform for people approaching or already enrolled in Medicare. Licensed advisors, who are licensed in every state, compare plan options nationwide against a member's doctors, prescriptions, preferred pharmacy and coverage preferences, and then recommend a plan and assist with enrollment. The company says it reviews every Medicare plan nationwide and makes recommendations regardless of whether it contracts with the plan in question.
After enrollment, Chapter Advocates provide ongoing support, including answering coverage questions, finding prescription savings and appealing prior authorization denials. The company also offers a free over-the-counter benefits app with home delivery to help members use plan OTC allowances, and in the year prior to April 2026 rolled out a provider directory and a prescription cost calculator. The platform uses AI to support its licensed advisors in making recommendations, and Chapter has partnered with Palantir on the technology platform that integrates data on all Medicare plans.
Advisor availability is published as Monday through Saturday, 9am to 9pm ET. Users can either book a call with an advisor or explore options themselves through the website.
Founding story
Chapter was founded to help Americans preserve their health, wealth and purpose in retirement, starting with Medicare. The founders cite seeing their own parents and grandparents exploited amid Medicare's complexity as the reason for building a platform intended to put seniors first.
Business model
Chapter provides Medicare advice and enrollment support to consumers at no cost to the member. The company states that advisor compensation does not depend on which specific plan a client selects, and that it recommends plans even when it does not contract with the carrier.
Advisory and enrollment services are free to seniors; the company describes a compensation model in which advisor pay is not tied to specific plan recommendations. In 2025 revenue tripled and the company surpassed $100 million in annual recurring revenue.
Traction
The company reports supporting more than 500,000 Medicare enrollees, a 4.9 rating across 7,318 reviews, a 5-star rating on Reviews.io and an A+ rating from the Better Business Bureau. Revenue tripled across 2025 and passed $100 million in ARR, while corporate headcount remained flat year over year.
Latest developments
In April 2026 Chapter announced a $100 million Series E led by Generation Investment Management, with Fifth Down Capital and 8VC joining as new investors and existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures participating. The company said it would use the funds to accelerate growth and develop additional financial products for seniors.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
Positioned as a Medicare navigation and advisory platform serving the Medicare Advantage and broader Medicare market; the company describes its platform as the country's leading Medicare navigation platform and reports having supported more than 500,000 Medicare enrollees.
Chapter states that it is the only company reviewing every Medicare plan nationwide and offering unbiased guidance, with advisor compensation decoupled from which plan a member chooses, in contrast to traditional commission-driven brokers and to public resources such as Medicare.gov.
Technology
A Medicare navigation platform that integrates data on all Medicare plans, built in partnership with Palantir, and uses AI to support licensed advisors' recommendations. Additional member-facing tools include an over-the-counter benefits app with home delivery, a provider directory and a prescription cost calculator.
Go-to-market
Direct-to-consumer through its website, where prospects book a time with a licensed Medicare advisor or self-serve through guided exploration tools; the company also pursues health system partnerships.
Medicare-eligible Americans, including retirees and seniors selecting, switching or managing Medicare coverage, along with their families.
Geography
United States nationwide; advisors are licensed in every state. The company opened a second office in Phoenix in October 2021 and is included in coverage of New York City startup funding rounds.
History
In September 2021 investor Peter Thiel joined the company's board. Chapter opened a second office in Phoenix in October 2021, adding 50 jobs, and by January 2022 its advisors were licensed in every state. That month the company raised a $42 million Series B led by Addition, bringing total raised to more than $61 million, with plans to fill 70 new roles. A later round of $75 million supported expansion of health system partnerships. In April 2026 the company announced a $100 million Series E led by Generation Investment Management, reporting that it had more than doubled its valuation since its previous round, which had closed less than a year earlier.
Risks & controversies
Chapter operates in the Medicare Advantage brokerage and advisory market, which is subject to Centers for Medicare & Medicaid Services rules and state licensing requirements, and where commission-driven broker incentives are a recurring concern that the company positions its compensation model against.
Compiled by commissioned research from 8 cited public sources — announcements, filings, and press listed under research sources below.
Key figures
latest reportedCompany-reported or press-reported figures, each dated to when it was claimed — not independently audited.
Competitors · 4
by search overlap
Companies competing with Chapter for the same Google search keywords, organic and paid, via search-intersection analysis.
Timeline · 7
launches, deals, and filingsChapter announced a $100 million Series E round led by Generation Investment Management, with Fifth Down Capital and 8VC as new investors and participation from existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures. The company said it had more than doubled its valuation since its prior round and would use proceeds to accelerate growth and build financial products for seniors.
$100M source ↗
In the year prior to April 2026, Chapter rolled out new tools including a provider directory and a prescription cost calculator.
Chapter raised $75 million to expand health system partnerships, per Fierce Healthcare's related coverage referenced alongside the Series E announcement.
$75M source ↗
Chapter announced a $42 million Series B led by Addition with participation from Narya Capital, Susa Ventures, Maverick Ventures, XYZ Venture Capital, Core Innovation Capital and Health2047 Capital Partners, planning to fill 70 new roles and improve the customer experience.
$42M source ↗
Chapter partners with Palantir on its technology platform, which integrates data on all Medicare plans so advisors can make recommendations.
Chapter opened a second office in Phoenix, creating 50 new jobs. Its Medicare advisors are licensed in every state.
Chapter's prior round closed in September 2021, when entrepreneur Peter Thiel joined the company's board of directors.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
Street Bikers United Maui Chapter raises $3,700 for Pacific Cancer Foundation’s Children’s Fund | Maui Nowmauinow.com · Jul 2026▸Research sources · 8
primary sources listed
- Chaptergetchapter.com · web
8 public sources were cited for this profile; the first-party ones are listed here.
Frequently asked questions
- What does Chapter do?
- Chapter is a Medicare navigation platform whose licensed advisors compare every U.S. plan and guide seniors through enrollment.
- Who founded Chapter?
- Chapter was founded by Noah Wilson.
- Who are Chapter's investors?
- Chapter's investors include Core Venture Capital, Maverick Ventures, Stripes, XYZ Venture Capital, 8VC, Addition, Fifth Down Capital, Generation Investment Management and 2 more.
- How much funding has Chapter raised?
- Chapter has disclosed $100M raised across 1 of its 3 known rounds.