Chapter
Founded 2020 · 270 employees on LinkedIn · 13 known investors
Chapter helps American seniors navigate and select Medicare plans by comparing options nationwide and recommending personalized coverage. The company serves retirees seeking clarity in health insurance enrollment to protect their health and financial security.
Also known as askchapter.org · Chapter Medicare
Founders & leadership
Investors · 13
Also in the syndicate · 1
Funding
SEC filings, press & company announcements$100M disclosed across 1 of 4 rounds · 2021–2026
- 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 sourcesSource ↗
- Undisclosed amountSeries ASep 2021
Narya Capital (lead), Core Innovation Capital, Health2047 Capital Partners, Maverick Ventures, 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 platform that pairs licensed Medicare advisors with software to help older Americans select coverage across Original Medicare, Medicare Supplement, Medicare Advantage and Part D prescription drug plans. The company states it reviews every Medicare plan available nationwide, including plans offered by carriers that do not compensate Chapter, and that advisors are paid the same regardless of which plan a member selects. Advisors can enter a member's prescriptions and preferred physicians to narrow plan options, and the company says its data team normalizes tens of thousands of plan variables to support recommendations.
Beyond enrollment, Chapter provides ongoing member support through an advocacy team that helps with post-enrollment issues such as prior authorization disputes and incorrect medical bills. Consumer-facing tools include a free app for using over-the-counter plan benefits with home delivery, a provider directory and a prescription cost calculator, the latter two rolled out in the year preceding April 2026. The company describes its mission as helping seniors preserve health, wealth and purpose in retirement, and says it is developing additional financial products for that population. Advisor phone coverage is offered Monday through Saturday, 9am-9pm ET.
Founding story
Founder and CEO Cobi Blumenfeld-Gantz started Chapter after watching his own parents, following extensive research, be steered into ill-fitting Medicare plans by a Medicare agent. The company frames its origin around systemic problems in the Medicare market that lead seniors into plans that do not fit their needs, at a cost of thousands of dollars a year and worse health outcomes.
Business model
Chapter offers its guidance to consumers at no cost, positioning the service as free with no fees or obligations. Coverage indicates the company is compensated by insurance carriers for enrollments, but structures advisor pay so that compensation does not vary with the plan recommended, including recommending plans from carriers that do not compensate Chapter.
Commission-based compensation from Medicare plan enrollments, with a flat internal advisor compensation model; the service is free to the consumer. The company reported surpassing $100 million in annual recurring revenue with revenue tripling across 2025.
Traction
The company's site cites more than 500,000 Medicare enrollees supported, a 4.9 rating across 7,318 reviews, five-star Reviews.io standing and an A+ Better Business Bureau rating; one landing page cites 250,000+ Americans helped and average savings of $1,100 on health costs. Across 2025 revenue tripled to more than $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 as new investors and existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures participating. The company said it more than doubled its valuation versus its prior round, which closed less than a year earlier, and would use the capital to accelerate growth and build financial products for seniors.
▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies
Market position
Chapter describes itself as the leading national Medicare navigation platform and the only national advisor that evaluates every Medicare plan option nationwide, including plans from non-compensating carriers, differentiating itself from traditional Medicare agents and brokers whose recommendations may follow commission incentives. The company cites that roughly 30-50% of people use a Medicare agent to enroll.
Nationwide review of every Medicare plan including those that do not pay Chapter; advisor compensation that does not vary by plan recommended; standardized internal advisor training; post-enrollment member advocacy for billing and prior authorization issues; and proprietary plan-data tooling.
Technology
A Medicare comparison platform that aggregates plan data nationwide and surfaces plan details, provider networks and drug coverage to advisors; the company says it uses AI to support its licensed advisors' recommendations. Consumer tools include an over-the-counter benefits app with home delivery, a provider directory and a prescription cost calculator. As of 2022 the company partnered with Palantir on its technology platform.
Go-to-market
Direct-to-consumer via its website, scheduled phone consultations with licensed advisors and a self-service option to explore plans online. The company states that referrals from existing members were its single largest source of new members in 2025, and prior coverage references expansion of health system partnerships.
Medicare-eligible Americans and retirees selecting or switching health coverage, including those choosing among Medicare Advantage, Medicare Supplement and Part D plans.
Geography
United States nationwide, with advisors licensed in every state; offices include a second location opened in Phoenix in October 2021, and the company is covered as a New York City-area startup.
History
Chapter raised a $42 million Series B in January 2022 led by Addition, following a September 2021 round after which Peter Thiel joined the company's board; at that point the company had raised more than $61 million. In October 2021 it opened a second office in Phoenix, adding 50 jobs, and its advisors became licensed in every state. The company later raised $75 million to expand health system partnerships, and in April 2026 announced a $100 million Series E led by Generation Investment Management.
Risks & controversies
The company's revenue depends on Medicare plan commissions and on the Medicare Advantage and Part D distribution environment, an area subject to CMS regulation. Chapter's public materials describe an industry in which many agents and brokers are said to lack the knowledge, data or incentives to give suitable advice, and note that bad actors profit from Medicare complexity.
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.
Timeline · 8
launches, deals, and filingsChapter announced a $100 million Series E round led by Generation Investment Management, with new investors Fifth Down Capital and 8VC and existing backers Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures and Maverick Ventures. The company said it more than doubled its valuation versus its prior round and would use the funds to accelerate growth and develop financial products for seniors.
$100M source ↗
In the year preceding April 2026, Chapter rolled out new consumer tools including a provider directory and a prescription cost calculator.
Chapter states that founder Cobi Blumenfeld-Gantz testified as part of the company's stated commitment to changing industry practices in Medicare plan distribution.
Prior to its Series E, Chapter raised $75 million to expand health system partnerships.
$75M source ↗
Chapter raised $42 million in a Series B led by Addition to expand its team by about 70 roles and improve the customer experience.
$42M source ↗
Chapter works with Palantir on the tech platform that integrates data on all Medicare plans for use by its advisers.
Chapter opened a second office in Phoenix, creating 50 new jobs; its Medicare advisers became licensed in every state.
In connection with a funding round in September 2021, entrepreneur Peter Thiel joined Chapter's board of directors.
Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.
In the news
▸Research sources · 8
primary sources listed
- Chapteraskchapter.org · 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 US Medicare navigation platform whose licensed advisors compare every Medicare plan nationwide for enrollees.
- Who are Chapter's investors?
- Chapter's investors include Fifth Down Capital, Health2047 Capital Partners LLC, Maverick Ventures, Morrison Seger Venture Capital Partners, Narya Capital, XYZ Venture Capital, 8VC, Addition and 4 more.
- How much funding has Chapter raised?
- Chapter has disclosed $100M raised across 1 of its 4 known rounds.