Digital Senior Care Navigator Fair Square Medicare Raises $15M 

What You Should Know:

– Digital senior care navigator Fair Square Medicare raises 15M in series A funding led by Define Ventures. The company, which is a YCombinator alum, has raised $19M to date.

– With 10,000 people turning 65 every day, Fair Square Medicare helps seniors find the right Medicare coverage regardless of commission, and is building a full-service digital healthcare assistance platform for seniors.

Care Navigator for Seniors

Launched in 2020 out of YC, Fair Square Medicare is a digital health platform company that’s revolutionizing how seniors navigate their healthcare. The commission-agnostic company provides tech-enabled services that help seniors find the best health insurance options while also providing concierge support to maximize their benefits.

Focus on Senior Education

A Kaiser Family Foundation study found that nearly 60 percent of Medicare enrollees don’t review or compare their coverage options annually because of overwhelming choices – figures that get worse for older beneficiaries and those with poorer health.

“The average person has 50 health insurance plans to choose from when they turn 65. They turn to a broker for help, who then almost always recommends the plan that pays them the most to sell,” said Daniel Petkevich, Founder and CEO of Fair Square Medicare. “I saw my parents have this experience, so I decided to build the brokerage I wish they had.” Fair Square Medicare focuses on educating instead of selling seniors and uses algorithmic intelligence to sort and present the most-relevant Medicare plans based on their budget and preferences, regardless of commission. The platform also includes a web portal that allows them to take full advantage of their available benefits.

More than 54 million people in the U.S. are 65 or older, and an estimated 10,000 more turn 65 every single day – numbers that are expected to increase as Baby Boomers continue to age. Many struggle to evaluate which Medicare plan is right for them, often turning to traditional insurance brokerage firms that are incentivized to recommend plans with the highest commissions. As a result, they’ll enroll in the wrong plan and end up switching in a year, which is one reason why some large public brokerage firms experience customer churn rates above 40 percent

By contrast, Fair Square Medicare retains more than 90 percent of its customers and has a net promoter score (NPS) of 95. The average NPS for insurance brokers in the U.S. was 34 in 2021 and has ranged as low as 9 over the last decade. Even though Fair Square Medicare could steer customers to enroll in higher-commission plans, many of its customers are enrolled in lower-commission Medicare Supplement plans.

Medicare One-Stop-Shop Features

Because of the trust, it’s built with customers, Fair Square Medicare is now positioned to become a comprehensive digital care navigation platform for seniors. The company plans to use the new investment to launch new services that can assist seniors with more parts of their healthcare journey, including:

– Finding and scheduling appointments with preferred providers; 

– Setting up annual preventive health and dental services; 

– Finding the lowest-available price on their prescriptions; 

– Providing access to digital health services that help them manage chronic conditions; 

– Enabling instant access to all health insurance benefits; and 

– Accessing on-demand consultations with a clinician to answer impromptu health questions.


Fair Square Medicare currently operates in 49 states and Washington D.C.