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Fair Square Medicare
Health Tech & Medtech · San Francisco, United States · Founded 2019
Data-driven personalized Medicare plan recommendations in 60 seconds MoreLess
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. Keywords: Medicare, health insurance, unbiased advice, Medigap, Medicare Advantage, senior healthcare, commission-based, annual review, customer-centric, U.S. market.
Company overview
Fair Square Medicare company information
The essential company record, classifications and operating signals in one place.
- Status
- Acquired
- Founded
- 2019
- Headquarters
- San Francisco, United States
- Employees
- 18
- Open positions
- None listed
- Dealroom signal
- 71.1
Valuation & funding
Fair Square Medicare 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 | ↗ |
| SEED✓Equity / VC | Mar 2020 | $125K | $500K | Y Combinator | — |
Financials
Revenue and workforce over time
Available revenue and workforce history. Fields without reported data are omitted.
| Year | Revenue | Growth | Employees |
|---|---|---|---|
| 2026 | $3.1M | 0% | 18 |
| 2025 | $3.1M | 0% | 19 |
| 2024 | $3.1M | 0% | 26 |
| 2023 | $3.1M | — | 26 |
| 2022 | — | — | 35 |
Growth signals
Fair Square Medicare website traffic
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.
Comparisons
Fair Square Medicare compared with similar companies
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Talent graph
Fair Square Medicare's talent
Source: Dealroom Talent Intelligence.
Global footprint
Where Fair Square Medicare has talent and traffic
team presence
In the news
Latest news about Fair Square Medicare
Recent press, funding announcements, and product moves mentioning Fair Square Medicare — open to read from the original sources.
Market sentiment
What the market is saying about Fair Square Medicare
An AI-synthesized read of the highest-engagement posts about Fair Square Medicare on X over the past 7 days. We rank by likes & retweets, ignore corporate channels, and surface the themes that broke out from real people.
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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