Fair Square Logo
Advising seniors on Medicare coverage options.

About Fair Square

We are an insurance company founded in 2019, dedicated to helping seniors understand their Medicare coverage options. We guide clients through the complexities of Medicare to find the best fit for their needs.

Our clients consistently recommend us, with 97% saying they would refer a friend. 90% of our clients stay with us year after year. More than half of our clients (53%) choose low-commission Medicare Supplements.

Mission & Values

Our mission is to empower seniors to make informed decisions about their healthcare by providing clear, unbiased advice on Medicare plans. We value transparency, client advocacy, and long-term relationships built on trust.

Team & Culture

We are a growing team of 11 to 50 employees, united by a commitment to helping seniors. Our culture is collaborative and client-focused, valuing clear communication and supportive teamwork.

Benefits & Perks

We offer competitive salaries, comprehensive health benefits, and opportunities for professional development. We also promote a healthy work-life balance with flexible scheduling options and paid time off.

Frequently Asked Questions

What products or services does Fair Square Medicare offer?

Fair Square Medicare helps seniors find appropriate Medicare coverage and acts as a Medicare advisor. They assist clients with navigating Medicare options.

What is Fair Square Medicare's client satisfaction and retention?

Fair Square Medicare reports that 97% of their clients would recommend them to a friend, and 90% of their clients remain with them annually.

What type of Medicare coverage does Fair Square Medicare focus on?

Fair Square Medicare helps seniors find various Medicare coverage options, with 53% of their clients utilizing low-commission Medicare Supplements.

When was Fair Square founded?

Fair Square was founded in 2019.

How many people work at Fair Square?

Fair Square has 11-50 employees.

Where does Fair Square hire?

Fair Square hires globally with a remote-first approach, allowing employees to work from anywhere.

Is Fair Square hiring?

Fair Square is not actively hiring at the moment. Check back later for new opportunities.

Does Fair Square hire for remote and work from home roles?

Yes, Fair Square is a remote-first company.

What is Fair Square's website?

Fair Square's website is www.fairsquaremedicare.com .

Where to find Fair Square on social media?

You can find Fair Square on LinkedIn .

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