Fair Square Medicare raises $15 mn in Series A funding led by Define Ventures

Fair Square Medicare, a tech-enabled concierge healthcare platform for seniors navigate Medicare Parts A & B, Medicare Advantage, and Medigap, has raised $15 million in Series A funding led by Define Ventures, with additional participation from Slow Ventures, Y Combinator, and angel investors. The company has raised $19 million to date.

Launched in 2020, Fair Square Medicare is led by Daniel Petkevich, the technical co-founder of fintech startup Trim.

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. The platform also includes a web portal that allows them to take full advantage of their available benefits.

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

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. I saw my parents have this experience, so I decided to build the brokerage I wish they had.

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. I saw my parents have this experience, so I decided to build the brokerage I wish they had.

Daniel Petkevich, founder and CEO of Fair Square Medicare

Fair Square Medicare is revolutionizing the way seniors engage with the U.S. healthcare system. Launched in 2020 out of YC, the company helps thousands of seniors navigate the complex maze of available Medicare coverage options and now plans to scale its platform to be a full-service care navigator for seniors.

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.

Seniors deserve a trusted healthcare partner that’s always acting in their best interest. Fair Square Medicare’s model builds trust with seniors, because it treats them like family. When you prioritize the long-term relationship with the customer over potential short-term financial gains, they’ll trust you with more of their health. That’s the recipe for sustainable growth, which is why we’re investing in Fair Square Medicare’s future.

Chirag Shah, partner at Define Ventures

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.

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. A 2020 Y-combinator (YC) graduate, Fair Square Medicare is headquartered in San Diego and is backed by Define Ventures, Slow Ventures, Amplo, and YC. For more information

by Peter Sonner