Chapter
Chapter is a Medicare advisory platform that compares plans nationwide to recommend the best option for seniors. The New York-based company has raised $284M and employs 268 people.
The growth story
Chapter grew from 26 to 268 employees between 2021 and 2026, raising $284M along the way, most recently a Series E in April 2026.
About
Chapter provides Medicare plan comparison services through advisors who recommend options based on individual needs, regardless of whether the company earns a commission. The platform aims to simplify Medicare decisions and prevent exploitation of seniors.
The company has raised $284M through a Series E round in 2026, though its headcount growth rate is unclear. Chapter employs 268 people, with a median tenure of 2 years, suggesting moderate turnover.
Founders and leadership
Chapter's largest function is sales, accounting for 5% of its workforce. The company is led by a team with backgrounds in insurance and technology, though specific leadership details are not provided.
The Chapter org chart
Cobi B. (CEO & Co-Founder) leads 20 mapped leaders with 11 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Healthcare Services 90 (+84% YoY), Sales 33 (+22% YoY), Finance 27 (+50% YoY), Operations 21 (+24% YoY), Customer Success and Support 13 (+30% YoY), Business Development 11 (+10% YoY).
Talent flow
Chapter recruits heavily from insurance companies like SelectQuote, Humana, and eHealth, with 6 hires from SelectQuote alone. Alumni frequently move to healthcare startups like CoverRight and Adaptive Innovations, as well as tech firms like Palantir and Squarespace.
Most common previous employers of Chapter staff: SelectQuote Insurance Services (6), Humana (3), eHealth (3), Spring Venture (3), Palantir Technologies (2), Bain & Company (2). Former Chapter employees most often moved to CoverRight (3), Adaptive Innovations (2), Palantir Technologies (2), Squarespace (2), DoorDash (2), Valinor (2).
Alumni worth knowing
The Chapter mafia
Chapter alumni have founded 5 companies, including Percepta (83 staff) and Cardinal40 (8 staff). These startups focus on healthcare and talent management, indicating Chapter's influence in these sectors.
5Michael Rochlin, was Product / Software until 2023Jake Leffew, was Editorial Marketing until 2020Josh Paul, was Head of Recruiting until 2022Shivang V., was Founding product until 2023Justin Curry, was Inside Sales Specialist | Medicare Advisor until 2025Web traffic
Traffic mix: 23% direct, 34% search, 16% social, 20% paid.
What this company is made of
Most common skills at Chapter: Sales (115), Customer Service (98), Leadership (92), Communication (78), Microsoft Office (65), Management (58), Microsoft Excel (55), Marketing (52).
Where the team actually sits
Chapter people are concentrated in New York, United States (20), United States (6), New York City Metropolitan Area (5), California, United States (3).
Search footprint
Chapter attracts about 25,190 organic search visits a month, traffic worth roughly $1M a month if bought through ads. It gained 11,101 ranking keywords and lost 16,672 in the last period.
What employees say
- Compensation
- 3.80 / 5
- Career opportunities
- 3.30 / 5
- Senior management
- 3.20 / 5
- Work-life balance
- 2.80 / 5
Frequently asked
Chapter has 268 employees as of September 2026.
Chapter has raised $284M in total, most recently a Series E round in April 2026.
Chapter was founded in 2020 by Cobi B., Corey Metzman, Ari Parker.
Cobi B. (CEO & Co-Founder) sits at the top of Chapter's reporting structure, with 11 direct reports.
The most common previous employers of current Chapter staff are SelectQuote Insurance Services (6 people), Humana (3 people), eHealth (3 people).
Former Chapter employees most often move to CoverRight (3), Adaptive Innovations (2), Palantir Technologies (2).
At least 5 companies have a founder who previously worked at Chapter, including Percepta, Cardinal40, Mosaic Talent.
Chapter attracts about 25,190 organic search visits a month, worth roughly $1M a month in equivalent ad spend.
The most common skills among Chapter staff are Sales, Customer Service, Leadership, Communication, Microsoft Office.
Chapter staff are concentrated in New York, United States (20), United States (6), New York City Metropolitan Area (5).
Chapter has about 90 people in Healthcare Services, up 84% over the past year, as of September 2026.
Chapter has about 33 people in Sales, up 22% over the past year, as of September 2026.
Computed from 56 current and 90 former Chapter profiles, as of September 2026. Source: Crustdata.
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