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Company

Fair Square Medicare

Rocket Ship RatingBased on the data VC Catalog holds.

Rocket Ship Rating: 89 out of 100

Your Medicare advisor for life

Also known as Help Button Inc

  • Insurance
  • Sales & marketing tech
  • AI native
Business model
B2B
Customers
Individuals shopping for Medicare plans
Legal name
Help Button Inc
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Record updated 28 September 2026

About

Fair Square Medicare is an AI-enabled platform for Medicare sales teams to achieve 90% annual client retention, 60% close rate, and 100% CMS compliance.

Funding snapshot

Total raised
$15MSum of rounds, as of 2026-09-18Source (opens in a new tab)
Latest round
Series A, $15M2022-08-25

Funding rounds

Series A
$15M2022-08-25, Company stated

Products

Web
Fair Square Medicare
Web
Shop Plans
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