Fair Square Medicare is a tech-enabled senior concierge healthcare platform. Today, they announced $15 million...

Fair Square Medicare is a tech-enabled senior concierge healthcare platform. Today, they announced $15 million in Series B funding. Define Ventures led the round with participation from Slow Ventures and YCombinator (YC), as well as angel investors. To date, the company has raised $19 Million.


Fair Square Medicare is changing the way seniors interact with the U.S. health care system. The company was founded in 2020 by YC and helps seniors navigate the maze of Medicare coverage options. It plans to expand its platform to provide full-service assistance for seniors.


A Kaiser Family Foundation study revealed that almost 60% of Medicare beneficiaries don’t compare their coverage options each year due to overwhelming options. This is a problem that gets worse for those who are older and have poorer health.


“The average person will have 50 options for health insurance when they reach 65.” Fair Square Medicare CEO Daniel Petkevich said that most people turn to a broker to help them choose the best plan. “I watched my parents go through this, so I decided that I would build the brokerage that I wished they had.”


Fair Square Medicare is focused on seniors education and not selling them. It uses algorithmic intelligence and a combination of budget and preference to find the best-suited Medicare plans for them. A web portal allows seniors to access all of their benefits.


Over 54 million Americans are 65 years old or older in the United States. An estimated 10,000 people turn 65 each day. These numbers are expected to rise as Baby Boomers age. Many people struggle to determine which Medicare plan is best for them. They often turn to traditional insurance brokerage firms, who are paid high commissions to recommend plans. They’ll end up enrolling in the wrong plan, and then switch within a year. This is why large public brokerage firms have customer turnover rates exceeding 40 percent.


Fair Square Medicare, on the other hand, retains over 90 percent of its customers. It also has a net promoter score of 95. In the U.S., the average NPS was 34 in 2021. It has fluctuated as low as 9 in the past decade. Fair Square Medicare can steer customers to higher-commission plans but many customers are enrolled with lower-commission Medicare Supplement plans.


Fair Square Medicare has built trust with its customers and is poised to be a digital-care-navigation platform that provides comprehensive senior care. The company plans to make use of the investment to launch new services to assist seniors in more aspects of their healthcare journey.


— Schedule appointments with preferred providers by scheduling an appointment

— Establishing annual preventive and dental services.

— Finding the lowest price for their prescriptions

— Access to digital health services for chronic conditions management.

— Instant access to all benefits of health insurance

— You can access on-demand consultations with a physician to answer any impromptu questions.


Chirag Shah, partner at Define Ventures, stated that seniors deserve a trusted partner in healthcare who will always act in their best interests. Fair Square Medicare builds trust with seniors because it treats them as family. If you value the long-term relationship you have with your customer more than short-term financial gain, customers will trust you with their health more. This is the key to sustainable growth. Fair Square Medicare’s future is proof of this.


Fair Square Medicare operates in 49 states, Washington D.C. and Chirag Shah will be joining the Fair Square Medicare Board.


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