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Fair Square Medicare
Data-driven personalized Medicare plan recommendations in 60 seconds
About Fair Square Medicare
Fair Square Medicare operates as an independent health insurance brokerage specializing in Medicare plans. The company provides comprehensive guidance on Medicare Parts A and B, Medicare Advantage, and Medigap plans, ensuring clients receive unbiased recommendations tailored to their needs. Fair Square Medicare serves individuals approaching or over the age of 65, helping them navigate the often complex Medicare landscape. The company operates in the U.S. healthcare market, focusing on transparency and customer-centric service. Its business model is commission-based, earning revenue when clients enroll in a plan through their service. Unlike other brokerages, Fair Square Medicare's recommendations are not influenced by commission structures, ensuring clients receive the best possible advice even if it means recommending a plan that pays no commission. The company also offers annual re-evaluations of clients' coverage to ensure they continue to receive the best value.
Source: Dealroom company dataAt a glance
- Status
- Acquired
- Founded
- 2019
- Headquarters
- San Francisco, United States
- Employees
- 18
- Open positions
- None listed
- Dealroom signal
- 71.1/100
- Industry
- Health
- Sub-industry
- Health Platform
- Sector
- Health Tech & Medtech, Hard Tech, YC W20
- Business model
- Marketplace & ecommerce
- Client focus
- b2c
Knowledge graph
More headlines
Funding history
Company financing events and reported valuations.
| Deal type | Date | Amount | Valuation | Investors | Source |
|---|---|---|---|---|---|
| ACQUISITION✓Exit | Jan 2026 | $0 | — | Senior Market Sales | ↗ |
| SERIES A✓Equity / VC | Aug 2022 | $15M | $60M | Define Ventures · Y Combinator · Slow Ventures | ↗ |
Financials
Revenue, earnings and other financial measures where available. Years marked “E” are estimates.
Growth signals
Latest recorded traffic for Fair Square Medicare is 7.9K monthly website visits, down 14.1% over the last three months. Fair Square Medicare's team declined 5.3% over the past year.
Similar companies
Company identity and context are open; selected comparison metrics preview what is available on the platform.
Investments and acquisitions
Recent portfolio relationships for companies that also act as investors or acquirers.
Investors
From Dealroom's funding and investor records, grouped by the round each investor first entered.
Seed1 investor entered at this stage
Series A2 investors entered at this stage
Define Ventures
Slow Ventures
Other known investors2 additional known investors
Senior Market Sales
Amplo
Source: Dealroom Talent Intelligence.
Global footprint
team presence
Market sentiment
An AI-synthesised read of the highest-engagement posts about Fair Square Medicare on X, ranked by likes and reposts, corporate channels excluded.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
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