Chapter
Category: AI in Healthcare
AI-powered Medicare navigation platform that helps seniors compare and enroll in Medicare health plans nationwide. Chapter was founded in 2020. The company is led by Cobi Blumenfeld-Gantz. Based in New York, New York. Team size: 101-500. Total funding raised: $285M. Latest round: Series E. Key investors include Generation Investment Management, Stripes, XYZ Venture Capital, Addition, Narya Capital, Susa Ventures, Maverick Ventures, 8VC, Fifth Down Capital, Core Innovation Capital, Health2047 Capital Partners.
- Founded
- 2020
- Headquarters
- New York, New York
- Team size
- 101-500
- Total funding
- $285M
Value proposition
Chapter reviews every single Medicare plan nationwide and provides unbiased, AI-powered recommendations — advisors are not incentivized by commissions, ensuring seniors get the best plan for their needs rather than the one that pays the highest commission.
Products and solutions
AI-powered Medicare plan comparison platform, personalized Medicare advisor service (licensed human advisors + AI), provider directory, prescription cost calculator, free OTC benefits app
Unique value
Only Medicare broker that reviews every plan nationwide with commission-free advisor recommendations; AI-native platform covering all major carriers (Humana, UnitedHealthcare, Cigna, etc.); trusted by 500,000+ Medicare enrollees.
Target customer
American seniors (age 65+) eligible for Medicare; financial institutions, healthcare providers, and content publishers that serve older Americans (B2B partnerships).
Industries served
Medicare navigation, health insurance, retirement planning, senior healthcare
Technology advantage
AI-native data platform that analyzes every Medicare plan nationwide against individual needs; unbiased recommendation engine (advisor incentives decoupled from commissions); proprietary provider directory and cost calculation tools; Palantir software foundation.
How they differentiate
Unlike traditional brokers (GoHealth, eHealth) who limit recommendations to plans that pay commissions, Chapter reviews ALL plans nationwide and its advisors are paid the same regardless of which plan a senior chooses. Backed by prominent political figures across the aisle (JD Vance, Peter Thiel, Al Gore, Donna Shalala), signaling trust and bipartisan support.
Main competitors
GoHealth, eHealth, SelectQuote, HealthPlanOne (ClearMatch Medicare)
Key partnerships
Ramsey Solutions (Dave Ramsey - RamseyTrusted partner), AARP, HSHS (Hospital Sisters Health System), partnerships with financial institutions, healthcare providers, and content publishers serving older Americans
Notable customers
500,000+ Medicare enrollees served, partnerships with financial institutions, healthcare providers, and content publishers nationwide
Major milestones
2020: Founded, 2021: $17M Series A led by Narya Capital (JD Vance's firm), 2022: $42M Series B led by Addition, 2024: $50M Series C led by XYZ Venture Capital (~$110M total), 2025: $75M Series D at $1.5B valuation led by Stripes, surpassed 500,000 enrollees, 2026: $100M Series E at $3B valuation led by Generation Investment Management (Al Gore), tripled revenue to exceed $100M ARR
Growth metrics
Tripled revenue in 2025; surpassed $100M ARR in 2025; 500,000+ Medicare enrollees served; over 2 million conversations with American seniors; flat headcount year-over-year while tripling revenue
Market positioning
Industry-leading AI Medicare navigation platform valued at $3B; tripled revenue in 2025 surpassing $100M ARR; positioned as the "trust layer" between seniors and technology in retirement
Geographic focus
United States
About Cobi Blumenfeld-Gantz
Ex-Palantir Technologies Forward Deployed Engineer (led US government teams); University of Cambridge education.
Official website: https://askchapter.org