Exclusive: Fair Square earns $15M to help seniors navigate Medicare
- Erin Brodwin, author of Axios Pro: Health Tech Deals

Illustration: Gabriella Turrisi/Axios
Senior insurance navigator Fair Square Medicare garnered $15 million in Series A funding, CEO Daniel Petkevich tells Axios exclusively.
Why it matters: Like other forms of public and private health insurance, Medicare is exceedingly complex and opaque β or as Petkevich describes it, "heinous" β making selecting a plan difficult.
Deal details: Define Ventures led the round and was joined by Slow Ventures and YCombinator.
- The new capital brings the San Diego company's total funding to $19 million.
Context: Fair Square's clearest rivals include traditional Medicare brokers and Quil, the senior care navigation company created in 2018 as a joint venture between Comcast and Independence Health Care.
Separately, a handful of other elder care-focused startups have raised funds of late including:
- Sage, which debuted in July with $9 million in seed funding to replace outdated senior living facility tech.
- Companionship startup Papa, which last year raised $150 million in Series D funds.
How it works: Fair Square's website helps seniors shop for Medicare, Medigap and Medicare Advantage using an algorithm that ingests information about their needs and budget.
- The company makes money via commissions from payers.
By the numbers: A recent Kaiser Family Foundation analysis concluded that every year, 57% of Medicare enrollees donβt assess their coverage options, in part due to comprehension difficulties.
- That percentage is higher among those aged 85+, those with lower incomes, people with lower education levels and people in fair or poor health, the report found.
What they're saying: Define Ventures partner Chirag Shah sees long term potential for Fair Square to be a trusted brand for seniors looking for assistance.
- The company presents an "opportunity to create a long-term relationship and affect the entirety of the care experience," Shah says. "This journey starts with the plan you pick and ends a very long time after that."
What's next: Petkevich plans to use the new capital to hire and to expand Fair Square's services to include:
- Appointment scheduling.
- Help finding low-cost prescriptions.
- Clinical consults for every day health questions.
- Access to virtual chronic care services.
π Our thought bubble: Given the above, we could see Fair Square eventually scooping up a virtual chronic care startup such as Welldoc, or a senior-focused digital pharmacy like PharmScript.
- "Right now our expertise is in software," says Petkevich. "In the future, could there be a world where we spin up our own services? Maybe."