Making Medicare Simpler for Seniors with Fair Square Medicare

We are excited to announce our partnership with Fair Square Medicare, a tech-enabled concierge to help seniors find, pick, and stay on the best Medicare plan for them. Thousands of seniors have utilized Fair Square to date, ensuring that they receive unbiased advice from a trusted expert who can guide them through the Medicare maze. Define Ventures is leading Fair Square Medicare’s $15m Series A and is joined by insiders Slow and YCombinator.

Nearly 62 million people in the U.S. are enrolled in Medicare with 10,000 more becoming eligible daily, making it one of the largest and fastest growing segments of the healthcare industry. Upon turning 65, those same people are forced to pick a Medicare plan in a broken and confusing process completely apathetic toward their needs, serving only the interests of legacy brokers. This results in seniors who are unhappy and dissatisfied, evidenced by 40% annual churn and 9–34% NPS for those models. Define Ventures strongly believes there is a better way to support seniors along his journey, which enompassess not only a commission-agnostic approach to plan selection, but also includes benefits education, annual appointment scheduling, prescriptions, and more. The entirety of this experience is wrapped in a consumer-centric interface that encourages seniors to utilize the plan’s benefits offerings, and promotes long-term plan engagement and retention. Serving our nation’s seniors in a way that supports their needs rather than the needs of existing solutions is precisely what Fair Square Medicare is built to address.

We first met Dan in March of 2020 and even then in the early days, his vision was direct: make Medicare simpler for seniors. When we reconnected almost two years later, we were floored by his momentum, product direction, and team efficiency; as an engineering-led organization, Fair Square’s unique ability to infuse technology into a historically stale industry was abundantly clear. They achieved this all while remaining true to their core values and proving that with superior customer service you can make a true difference in seniors’ lives: to date they have retained over 90% of their clients year-over-year with an NPS of 95+. By first doing what’s right for the consumer, starting with choosing the right plan, we believe that Fair Square can achieve long-term sustainable success in all facets of the insurance industry. Fair Square is led by Daniel Petkevich (Founder & CEO), a repeat founder with deep experience in consumer centric technology.

Define Ventures and Fair Square Medicare have already embarked on a close relationship spanning commercial partnerships, recruiting top tier talent, and establishing key connections across the healthcare ecosystem:

We’re thrilled to partner with Define. In our short time together, they’ve connected us to key executives at payors and providers, offered valuable strategic insight, and introduced us to experienced operators who’ve helped us answer key questions. They are among a special set of investors I’ve worked with that add unique value. — Daniel Petkevich, Founder & CEO

Fair Square Medicare currently operates in 49 states and this new round of funding will continue to help develop products and services to ease seniors’ journeys into and through Medicare, as well as expand its commercial footprint. We couldn’t be more excited to partner with Dan and the Fair Square team as they execute on their mission of making healthcare easier to use for millions of seniors across the country.

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