About Fair Square Medicare
Fair Square Medicare is a Financial Services company based in Oakland (United States) founded in 2020 by Daniel Petkevich, and was acquired by Senior Market Sales in January 2026. Medicare insurance brokerage services are provided by Fair Square Medicare. Fair Square Medicare has raised $15.15 million across 2 funding rounds from investors including Senior Market Sales, Define Ventures and Slow Ventures. The company has 55 employees. Its chief executive, as recorded, is Daniel Petkevich. Fair Square Medicare offers products and services including Medicare Plans and Consulting Services. Its focus areas include Insurance Distribution and Diversified. Its legal entity is Fair Square Medicare Inc.
Company details
Fair Square Medicare was established in 2020 in Oakland, United States, by Daniel Petkevich as its founder and CEO. Operations center on insurance brokerage within the health sector, where Medicare plans are facilitated for clients. Guidance is offered on plan selection, enrollment, and coverage options through an online platform at fairsquaremedicare.com. Services extend to individuals across the United States seeking Medicare-related support.
- Headquarters Oakland, United States
- Employees 55
- Founders Daniel Petkevich
- Stage Acquired
- SectorsFinancial Services
- Website category Finance · Insurance
- Email••••••••
- Phone•••• ••••
- Website fairsquaremedicare.com
- Acquired by Senior Market Sales (Jan 2026)
- Legal Name Fair Square Medicare Inc.
- Total Equity Funding$15.15M (USD)
in 2 rounds
- Latest Funding Round$15M (USD), Series A
Aug 2022
- InvestorsSenior Market Sales
& 3 more
- Employee Count55
- Acquired bySenior Market Sales
(Jan 2026)
Products & Services of Fair Square Medicare
Fair Square Medicare offers a comprehensive portfolio of products and services, including Medicare Plans and Consulting Services.
Medicare plans are managed for health coverage of seniors
Consulting services are provided for healthcare options and compliance
Funding Insights of Fair Square Medicare
Fair Square Medicare has successfully raised a total of $15.15M across 2 strategic funding rounds. The most recent funding activity was a Series A round of $15 million completed in August 2022. This substantial capital infusion reflects strong investor confidence in the company's business model, growth potential, and market opportunities. The funding enables strategic expansion, product development, market penetration, and operational scaling to drive long-term value creation and competitive advantage.
- Total Funding $15.15M
- Total Rounds 2
- Last Round Series A — $15M
- First Round $150,000
(Jun 2020)
- Investors Count 3
All 2 funding rounds of Fair Square Medicare with amounts and investors; the two latest post-money valuations are shown, the rest are part of the premium plan.
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Aug 2022 | $15M | Series A | – | Define Ventures | |
| Jun 2020 | $150,000 | Seed | – | Y Combinator | – |
4 investors in total: 4 institutional.
Investors in Fair Square Medicare
Fair Square Medicare has secured backing from 4 investors, including venture fund investors. Prominent investors backing the company include Senior Market Sales, Define Ventures and Slow Ventures.
| Investor | Description | Founded Year | Domain | Location |
|---|---|---|---|---|
Define Ventures is focused on early-stage health tech investments. | definevc.com | |||
Early-stage tech investments are made primarily in US companies. | slow.co | New York, United States | ||
Early-stage startups are accelerated via funding and educational programs. | ycombinator.com | Mountain View, United States | ||
Lead generation and marketing services for senior markets are provided. | 1982 | seniormarketsales.com | Omaha, United States |
Investor details for Fair Square Medicare
The complete investor list, round-by-round participation and investor portfolios require an active premium plan.
- Complete investor list
- Round participation
- Investor portfolios
- Co-investor network
Verified entity values are shown only after access is granted.
People of Fair Square Medicare
4 people are tracked at Fair Square Medicare (2 in leadership, 2 in team); the tracked headcount is 55.
| Name | Role | Group |
|---|---|---|
Daniel Petkevich | Founder & CEO | Leadership |
Dan Petkevich | Founder & CEO | Leadership |
Joseph Casamassima | Medicare Advisor | Team |
Peter Austin | Brokerage Team Lead | Team |
Complete people profiles for Fair Square Medicare
Full employee and board profiles, team structure, tenure and professional contact details require an active premium plan.
- Full employee list
- Team structure
- Board tenure
- Professional contacts
Verified entity values are shown only after access is granted.
Timeline of Fair Square Medicare
4 dated milestones of Fair Square Medicare across 6 years, from founding to its latest funding, stage changes and deals.
- Founded Fair Square Medicare is founded.
- Funding First funding round of $150K.
- Funding Latest funding round, Series A, of $15.0M.
- Exit Acquired by Senior Market Sales.
Web traffic of Fair Square Medicare
The website of Fair Square Medicare (fairsquaremedicare.com) receives about 5.9K visits a month and ranks #1,191,558 among all websites worldwide, #4,737 in Insurance.
- Monthly visits5.9K
▼ 59% vs previous month
- Unique visitors5.4K
per month
- Global rank#1,191,558
among all websites
- Category rank#4,737
Finance · Insurance
- Bounce rate46%
- Pages per visit6.4
- Average visit7 min 57 sec
- DevicesDesktop 37% · Mobile 63%
Websites whose visitors overlap most with Fair Square Medicare. Affinity shows how closely the audiences match.
| Website | Domain | Audience affinity | Monthly visits | Global rank | Profile |
|---|---|---|---|---|---|
| ametros.com | 100% | 11.1K | #2,522,474 | View details | |
| resolvemedicalbills.com | 99% | 13.9K | #982,751 | View details | |
hbinsurance.com | hbinsurance.com | 97% | #11,693,504 | – | |
| valuepenguin.com | 84% | 121.8K | #278,856 | View details | |
| trustedchoice.com | 67% | 93.6K | #370,538 | View details | |
| •••••••••• | ••••••.com | ••% | •.•M | #••••• | – |
All 6 similar websites and full traffic analytics for Fair Square Medicare
The complete similar-websites list, audience overlap and engagement analytics require an active premium plan.
- 6 similar websites
- Audience overlap
- Engagement analytics
- Traffic by brand
Verified entity values are shown only after access is granted.
Top companies in Insurance & Risk Management
3 companies that operate in the same segment as Fair Square Medicare (Insurance & Risk Management) in United States, ranked by their profile score on The Company Check.
| Company | Description | Founded | Location | Total funding | Revenue | Employees |
|---|---|---|---|---|---|---|
Investment advisory, insurance distribution, and risk management services are provided. | 1998 | Chicago, Illinois, United States | USD 1.6 B | |||
Financial institution offering insurance & transaction services | 1847 | Jacksonville, United States | USD 500 M | USD 14.51 B | 23,530 | |
Integrated healthcare services and coverage are provided nationwide. | 1945 | United States |
Unlock complete access to The Company Check
Get unrestricted viewing across everything we track — from companies and brands to investors, funding rounds, acquisitions, financials, and more.
- Unlimited viewing on all profiles Companies, investors, financials, funding, acquisitions & directors
- Full access to every database India & global coverage, advanced filters and rich profile details
- Always-on access from your team account Single premium plan for everything you see on the portal
Frequently Asked Questions about Fair Square Medicare
Fair Square Medicare was founded in 2020.
Fair Square Medicare is headquartered in Oakland, United States. It is registered at Oakland, California, United States.
Daniel Petkevich is the CEO of Fair Square Medicare, as recorded in our data. They have also founded this company.
Fair Square Medicare is a funded company, having raised a total of $15.15M across 2 funding rounds to date. The company's 1st funding round was a Seed of $150K, raised on Jun 2020.
Fair Square Medicare has 55 employees.
Fair Square Medicare was established in 2020 in Oakland, United States, by Daniel Petkevich as its founder and CEO. Operations center on insurance brokerage within the health sector, where Medicare plans are facilitated for clients. Guidance is offered on plan selection, enrollment, and coverage options through an online platform at fairsquaremedicare.com. Services extend to individuals across the United States seeking Medicare-related support.
Fair Square Medicare offers Medicare Plans and Consulting Services.
Fair Square Medicare has 4 investors. Key investors include Senior Market Sales, Define Ventures, Slow Ventures, and Y Combinator.
Fair Square Medicare operates through Fair Square Medicare Inc..
Yes. Fair Square Medicare was acquired by Senior Market Sales in January 2026.