Chapter
Chapter (Memoir, Inc.) is an AI-powered Medicare navigation platform that helps U.S. seniors compare and enroll in Medicare plans across all 50 states plus DC, generating revenue via carrier commissions and increasingly distributing through wealth advisors and health system partnerships.
- Company typePrivate
- Founded2020
- HeadquartersNew York, United States
- Headcount101–250
- GTM typeB2C
- OfferingServices
What Chapter does
Chapter (legal entity Memoir, Inc.) is an AI-powered Medicare navigation platform that helps U.S. seniors compare, select, and enroll in Medicare Advantage, Medicare Supplement, and Part D prescription drug plans. The company operates through a multi-entity structure: Chapter Advisory, LLC functions as a licensed insurance brokerage; Chapter Medicare, LLC and Quentin Cares Insurance Services Inc. hold additional insurance licensure; and Chapter Technologies, LLC operates the consumer-facing OTC benefit application. The platform maintains active licensure across all 50 states plus the District of Columbia and surfaces a catalog of roughly 18,160 plans from 50 carrier organizations including Humana, Cigna, United Healthcare, CVS Health, Aetna, BCBS, and Kaiser. Its recommendation engine and knowledge retrieval layer sit on top of this plan universe, paired with licensed advisor support led publicly by Lead Medicare Advisor Ari Parker.
The company's go-to-market combines direct-to-consumer acquisition with an increasingly important B2B2C referral channel. Distribution partnerships include flagship agreements with Mercer Advisors (wealth management), Zoa Life (health system), MultiCare, and Sun River Health, along with content integrations through NerdWallet and Dr. Ed. The advisory service is offered free to consumers, with revenue generated via standard Medicare insurance carrier commissions on enrolled plans. The OTC benefits app extends the relationship into post-enrollment engagement by helping members redeem over-the-counter allowances bundled with Medicare Advantage plans.
Chapter was founded in 2020 by Vivek Ramaswamy, Cobi Blumenfeld-Gantz (CEO), and Corey Metzman (COO). It has raised approximately $285M across five venture rounds (Series A through E) between 2021 and April 2026, with the most recent Series E of $100M led by Generation Investment Management at a $3B valuation. The company reported $100M+ ARR in 2025, with revenue tripling year-over-year against a roughly flat corporate headcount, indicating substantial AI-driven operating leverage. The company reports supporting 500,000+ Medicare enrollees and holds an A+ BBB rating with a 4.9/5 average across 6,385 reviews.
Chapter firmographics
Firmographics- Name
- Chapter
- Legal name
- Memoir, Inc.
- Website
- https://askchapter.org
- Company type
- Private
- Founded year
- 2020
- Operating status
- Operating
- Headcount range
- 101–250 employees
- Short description
- Chapter (Memoir, Inc.) is an AI-powered Medicare navigation platform that helps U.S. seniors compare and enroll in Medicare plans across all 50 states plus DC, generating revenue via carrier commissions and increasingly distributing through wealth advisors and health system partnerships.
- Ownership category
- akta.pro rank
Chapter industry classification
Industry- Product category
- Medicare Insurance Advisory
- NAICS
- Insurance Agencies and Brokerages (52421)
- SIC
- Insurance Agents, Brokers & Service (6411)
- akta.pro primary industry
- Medicare Plan Distribution & Brokerage (Captive, Independent, FMOs) (FSAIAGAH)
Keywords
Where Chapter is headquartered
LocationHeadquarters
- HQ city
- New York
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
Chapter business model
Business model- GTM type
- B2C
- Offering type
- Services
- Cost components
- Personnel, Marketing or Sales, Technology or R&D, Operations, Others
Revenue model
- Insurance Carrier Commissions on Medicare Plan Enrollment: Chapter Advisory, LLC is a licensed insurance agency that represents Medicare Advantage HMO/PPO/PFFS organizations and standalone Part D prescription drug plans with a Medicare contract. Revenue is generated through commissions paid by carriers when a Chapter advisor enrolls a consumer in a plan. Currently represents 50 organizations offering 18,160 products nationwide.
- Partnership and Referral Revenue (Financial Advisors, Health Systems, Content Publishers): Monetizes partnerships with financial advisors, wealth managers, health systems, banks, and content publishers who route clients/patients to Chapter's Medicare advisory services, with commission or referral economics tied to resulting enrollments.
- OTC Product Fulfillment Revenue (Chapter Technologies, LLC): Chapter Technologies, LLC operates the myotc.com app where users can browse, research, and place orders for over-the-counter health and wellness products using their plan OTC benefits; transaction-based revenue from product orders processed via the platform.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Freemium | — | Free Medicare Guidance Service for Consumers |
| Unit Pricing | — | OTC Benefit Fulfillment via myotc.com (Chapter Technologies) |
Go-to-market motion1 record
Distribution channels4 records
Marketing channels9 records
Chapter product offering
Product offeringCore offering
Chapter (Memoir, Inc.) operates an AI-powered Medicare navigation platform that pairs a proprietary questionnaire and recommendation engine with licensed human advisors to help seniors compare Medicare Advantage, Medicare Supplement, and Part D plans from every carrier nationwide. Insurance brokerage is delivered through a dedicated licensed agency subsidiary (Chapter Advisory, LLC), and the company extends the platform with a free OTC benefits app (myotc.com) for home delivery of eligible health products.
Product overview
Chapter operates a platform-plus-modules architecture under parent Memoir, Inc. to serve seniors navigating Medicare and retirement. The core is the AI-powered Chapter Medicare Navigation Platform at askchapter.org, which uses a proprietary questionnaire and recommendation engine to match seniors to Medicare Advantage, Supplement, and Part D plans from every carrier nationwide and pairs them with licensed advisors. Insurance brokerage is delivered through a dedicated sub-brand, Chapter Advisory Services (Chapter Advisory, LLC / Chapter Insurance Services in California), a licensed health insurance agency that enrolls members into plans. The platform extends with the Chapter OTC App (Chapter Technologies, LLC at myotc.com), a free OTC benefits redemption and home-delivery module that helps members use plan benefits. Education and thought leadership are delivered via the Chapter Magazine / Resources Hub, featuring Medicare explainers, retirement tips, and senior health content. Together these products form an integrated Medicare navigation, brokerage, OTC fulfillment, and retirement education ecosystem for older Americans.
Differentiator
Problem solved
Functional benefit
Brands
- Chapter Advisory: Licensed insurance agency that offers Medicare Supplement, Medicare Advantage, and Part D prescription drug plans; wholly owned subsidiary of Memoir, Inc.
- Chapter Insurance Services
- Chapter OTC
- AskChapter.org
Products and services
- Chapter Medicare Navigation Platform AI-powered Medicare advisory and navigation platform at askchapter.org that guides seniors through Medicare plan selection using a proprietary questionnaire and recommendation engine, with free, unbiased consultations from licensed Medicare advisors; supports Medicare Advantage, Medicare Supplement, and Part D plan comparison across all U.S. carriers.
- Chapter OTC App Free over-the-counter (OTC) benefits redemption and home-delivery app operated by Chapter Technologies, LLC at myotc.com, enabling Medicare Advantage members to use their plan OTC benefits (e.g., UnitedHealthcare OTC card) to order eligible health and wellness products with home delivery.
- Chapter Advisory Services Licensed health insurance agency services provided by Chapter Advisory, LLC (d/b/a Chapter Insurance Services in California, Lic. No. 6003691), a wholly owned subsidiary of Memoir, Inc., representing 50 organizations offering 18,160 Medicare Advantage, Medicare Supplement, and Part D products nationwide under National Producer Number 19631148.
Quantifiable outcome
- $1,100 average savings per enrollee
- +5 more outcomes
Companies that use Chapter
Customer profileNamed customers2 records
Ideal customer profiles3 records
Chapter technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration1 record
AI capability4 records
Feature5 records
Chapter partnerships and signals
Strategic signalPartnerships
23 partnerships are on record, tiered minor, core and flagship.
- Mike Lindell Media / LindellTVminorChapter (operated by Memoir Inc. as AskChapter.org) was added as an advertiser on the LindellTV platform run by Mike Lindell Media Corp. CEO Mike Lindell highlighted Chapter's free, unbiased Medicare advisory services and its high customer rating. The LindellTV network serves over 7 million monthly viewers, providing Chapter with conservative-media audience reach for Medicare advisory leads.
- Palantir TechnologiescorePalantir Technologies was disclosed as a strategic partner supporting Chapter's proprietary technology platform at the time of its Series A funding in September 2021, providing data infrastructure underpinning Chapter's Medicare plan recommendation capabilities.
- National Council on AgingcoreThe National Council on Aging (NCOA) was disclosed as a partner at the time of Chapter's Series A funding in September 2021, supporting Chapter's mission of improving Medicare plan selection for older Americans and aligning with NCOA's senior advocacy work.
- WealthspireminorWealthspire is a wealth management firm featured as a partner on Chapter's Partnerships page. The partnership supports routing Wealthspire's retiree clients to Chapter's Medicare advisory service as part of their retirement planning offering.
- Ohio Chamber of CommerceminorOhio Chamber listed as a Chapter partner organization, enabling member-facing distribution of Medicare advisory resources to Ohio-based employers and their employees approaching retirement.
- GoodRxminorGoodRx featured on Chapter's Partnerships page, indicating a co-marketing or referral relationship to help consumers find prescription drug savings via GoodRx in conjunction with Chapter's Medicare plan guidance.
- Cadence BankminorCadence Bank listed as a Chapter partner; the relationship enables routing bank customers approaching retirement to Chapter's Medicare advisory service through Cadence's financial offerings.
- MultiCare Health SystemcoreMultiCare Health System is featured as a Chapter partner on the Partnerships page, representing the health system channel segment that helps patients navigate Medicare coverage when transitioning from commercial coverage or impacted by carrier disruptions.
- MPGminorMPG listed as a Chapter partner on the Partnerships page, supporting co-marketing or referral distribution to MPG's audience.
- Sun River HealthcoreSun River Health featured on Chapter's Partnerships page as a health system partner for patient Medicare navigation support, helping patients maintain in-network provider access during payer disruptions.
- NerdwalletminorNerdwallet featured on Chapter's Partnerships page, indicating a content publisher partnership for distribution of Chapter's Medicare advisory resources to Nerdwallet's audience of personal finance readers.
- Mercer AdvisorsflagshipMercer Advisors introduced its clients to Chapter to handle Medicare complexity, leveraging Chapter's customer satisfaction, informed advisors, and nationwide coverage. Today well over 50% of Mercer's clients have signed on with Chapter. Featured as a flagship wealth-management partner on the Partnerships page.
- Dr. Ed (YouTube retirement benefits expert)coreDr. Ed, a popular retirement benefits expert with over 600,000 YouTube followers, partnered with Chapter for advertising and promotional support. Chapter provides unbiased access to all healthcare networks and measurable Medicare outcomes to Dr. Ed's audience of retirees.
- Zoa Life (leading health system)flagshipZoa Life, a leading health system that experienced a payor exit from select markets in 2024, partnered with Chapter to provide compliant Medicare guidance to thousands of impacted customers. As a result, 99% of Zoa's patients enrolled in coverage keeping them in-network, and Zoa retained 4.5x more patients than in past outreach campaigns. Featured as a flagship case study on the Partnerships page.
- HumanacoreHumana is one of the Medicare Advantage/Part D insurance carriers represented by Chapter Advisory, LLC; Chapter compares and recommends Humana plans alongside other carriers. Chapter represents 50 organizations offering 18,160 products nationwide.
- CignacoreCigna is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares Cigna plans alongside other carriers on its platform.
- United HealthcarecoreUnited Healthcare is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares United Healthcare plans and integrates its OTC card benefits via the Chapter OTC app.
- CVS HealthcoreCVS Health (Aetna parent) is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares CVS Health / Aetna Medicare plans on its platform.
- AetnacoreAetna is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares Aetna Medicare plans alongside other carriers.
- BlueCross BlueShieldcoreBlueCross BlueShield is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares BCBS Medicare plans alongside other carriers on its platform.
- Kaiser PermanentecoreKaiser Permanente is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares Kaiser Medicare plans alongside other carriers.
- Devoted HealthminorDevoted Health is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares Devoted Health plans alongside other carriers on its platform.
- WellCareminorWellCare is one of the Medicare insurance carriers represented by Chapter Advisory, LLC; Chapter compares WellCare plans alongside other carriers.
Scale indicators11 records
Recent moves6 records
Expansion highlights5 records
Chapter competitors and assessment
Company assessmentDirect peers
- eHealth: eHealth is a publicly traded Medicare Advantage and ACA health insurance marketplace that operates a similar advisor-driven, carrier-commission-revenue model to Chapter, but with a much broader individual and family plan portfolio. It is the most directly comparable large Medicare broker competitor.
- Connie Health: Connie Health is a licensed Medicare advisory that pairs local agents with digital tools to help seniors compare Medicare Advantage, Supplement, and Part D plans. Its advisor-led, multi-carrier model and senior-only focus make it one of the closest direct competitors to Chapter.
- GoHealth: GoHealth is a leading Medicare-focused health insurance marketplace and licensed broker that sells Medicare Advantage, Supplement, and Part D plans nationwide via a phone-and-digital advisor model. It directly competes with Chapter in the senior demographic with comparable commission-based economics.
- SelectQuote: SelectQuote operates a senior-focused insurance distribution platform (Senior, Life, Auto & Home divisions) with the Senior division centered on Medicare Advantage and Supplement plans. It is a direct, large-scale competitor to Chapter in the licensed Medicare broker space.
Others
- Wellvana: Wellvana is a senior-focused healthcare company that partners with primary care providers to deliver value-based care for Medicare beneficiaries. It is adjacent rather than directly competitive with Chapter, but serves the same Medicare demographic via health system channels, creating overlap on the B2B2C partner side.
- Devoted Health: Devoted Health is a Medicare Advantage health plan that offers its own plans and care services directly to seniors. It is represented by Chapter's platform as one of the 50 carrier partners, but as a payer it is also an adjacent ecosystem participant whose direct-to-consumer tools compete loosely with Chapter's advisory value proposition.
Broad incumbents
- Medicare.gov (CMS): Medicare.gov is the federal government's official plan finder and enrollment portal, providing baseline plan comparison for all Medicare beneficiaries. It is the structural incumbent that any digital Medicare broker must position around, and a free alternative that compresses Chapter's value proposition at the low end.
Emerging players
- Hella Health: Hella Health is an emerging digital Medicare brokerage that targets younger seniors and multicultural markets with an online-first enrollment experience. It competes with Chapter for digital-native Medicare shoppers and represents a growing direct competitor cohort.
- Healthpilot: Healthpilot is an AI-driven Medicare plan recommendation platform that helps seniors compare and enroll in Medicare Advantage and Part D plans online with an automated, advisor-light model. It competes with Chapter's recommendation engine directly and pressures the advisor-led hybrid economics.
- Medicareful (eHealth subsidiary): Medicareful is an eHealth-owned AI-assisted Medicare plan comparison tool that provides free, automated plan recommendations. It overlaps with Chapter's recommendation engine functionality and is part of eHealth's broader push into digital Medicare.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat6 records
Key risks6 records
Key highlights7 records
Customer concentration
Chapter social profiles
Digital presenceChapter compliance and trust
Trust signalCompliance3 records
Chapter financial estimates
Financial estimateRevenue estimate
Valuation estimate
Chapter leadership team
Management profileNumber of profiles
Profiles6 records
Chapter subsidiaries and ownership
Company hierarchySubsidiaries4 records
Chapter funding detail
Funding detailFunding overview
Funding rounds7 records
Investors13 records
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Chapter M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Chapter
What does Chapter do?
Chapter (Memoir, Inc.) operates an AI-powered Medicare navigation platform that pairs a proprietary questionnaire and recommendation engine with licensed human advisors to help seniors compare Medicare Advantage, Medicare Supplement, and Part D plans from every carrier nationwide. Insurance brokerage is delivered through a dedicated licensed agency subsidiary (Chapter Advisory, LLC), and the company extends the platform with a free OTC benefits app (myotc.com) for home delivery of eligible health products.
Is Chapter a public or private company?
Chapter is a private company. It is classified as venture growth investor backed and is currently operating.
When was Chapter founded?
Chapter was founded in 2020. It employs 101 to 250 people.
Where is Chapter based?
Chapter is headquartered in New York, United States, in the North America region.
How does Chapter make money?
Three revenue lines are on record. Insurance Carrier Commissions on Medicare Plan Enrollment is the primary driver. The others are partnership and Referral Revenue (Financial Advisors, Health Systems, Content Publishers) and OTC Product Fulfillment Revenue (Chapter Technologies, LLC).
Who are Chapter's main competitors?
Direct peers on record are eHealth, Connie Health, GoHealth and SelectQuote. Others are Wellvana and Devoted Health. Medicare.gov (CMS) is listed as a broad incumbent. Emerging players are Hella Health, Healthpilot and Medicareful (eHealth subsidiary).
Does Chapter have an API?
No public API is recorded for Chapter.
What industry is Chapter in?
Chapter's product category is Medicare Insurance Advisory. Its primary akta.pro industry code is FSAIAGAH, Medicare Plan Distribution & Brokerage (Captive, Independent, FMOs). Its NAICS code is 52421 and its SIC code is 6411.