Chapter

Chapter provides a technology-enabled advisory platform that helps older Americans navigate Medicare and retirement-related healthcare decisions.

Insurance Health and bio

Latest funding

$100M Series B+ · April 9, 2026

Led by Generation Investment Management · Source: fundraisingfox.com

Total raised: $209M across 4 sourced rounds

All 5 rounds ↓

Website: askchapter.org.

X: @askchapter · 305 followers.

LinkedIn: joinchapter.

Categories: Insurance Health and bio.

Stage: Series B+.

Based in: New York, United States.

Founded: 2020.

Total raised: $209M in 4 sourced rounds.

Last round: Apr 9, 2026 · 220 days ago.

Headcount: 51–100 employees.

On Recent Funding since: Sep 29, 2026.

Signals

X account@askchapter · created Mar 4, 2021 (5 years old) · 305 followers

Website registeredJan 15, 2020 (6 years old)

About Chapter

It offers access to licensed advisors who guide users through plan selection, enrollment timing, and coverage evaluation. Chapter Advisory, LLC, a licensed health insurance agency, provides insurance agency services. The company also offers a free OTC app for tracking healthcare benefits and accessing over-the-counter allowances.

TIMELINE · MONEY RAISED

Chapter | 615 days from website to first raise on record

@askchapter·Raised $209M in 4 sourced rounds·2 signals before the first raise

Money raised, round by round (amounts linked to their source). Pins are dated signals; hover the icons for dates.

Funding rounds

Date	Round	Amount	Lead	Source
Apr 9, 2026	Series B+	$100M	GGeneration Investment Management	fundraisingfox.com
Apr 21, 2025	Series B+	undisclosed	SStripes	pulse2.com
May 14, 2024	Series B+	$50M	XXYZ Venture Capital	coverager.com
Jan 11, 2022	Series B+	$42M	AAddition	finsmes.com
Sep 21, 2021	Series A	$17M	NNarya Capital	fundraisingfox.com

Timeline

March 4, 2021
X account created
January 15, 2020
Website created

Founders and team

CB
Cobi Blumenfeld-Gantz Founder

LinkedIn
CM
Corey Metzman Founder

LinkedIn
VR
Vivek Ramaswamy Founder

LinkedIn
ML
Megan Leinenbach Partnerships

Acquisitions

Acquired company	Price	Announced
HHively	Not disclosed	Oct 28, 2026 · Fierce Healthcare
RRidgeway	Not disclosed	Oct 22, 2026 · citybiz

Investors

Companies like Chapter

AAngle HealthSeries B+ · Sep 2026
CConnie Health$40M Series B+ · Jun 2026
DDevoted Health$366M Series B+ · Mar 2026
HHealthcarePre Seed · Aug 2026
TTalkiatry$210M Series B+ · Feb 2026
SSeen Health$22M Series A · Nov 2024

Other companies backed by Generation Investment Management

VVoltus$225M Series B+ · Oct 2026
GGridware$55M Series B+ · Nov 2025
FFNZ$650M Series B+ · Nov 2025
WWEKA$140M Series B+ · May 2024
GGloatSeries B+ · May 2023
IInnovaccerSeries B+

Generation Investment Management portfolio →

Sources and API

Every amount links to the page it came from. * Estimated from an accelerator's published standard deal, not a company-specific disclosure. How Recent Funding sources and verifies funding data. The same data as JSON: /api/v1/companies/chapter-2 (get a free API key).