MEET KRIS COWLES

Co-Managing Director of Medigap Plans of America, LLC:

Kris Cowles is the Owner and Managing Director of Medigap Plans of America, where he helps seniors navigate Medicare and design comprehensive healthcare strategies that provide long-term security and peace of mind. With nearly three decades of experience in financial services and insurance, Kris brings a unique combination of corporate leadership and entrepreneurial expertise to every client relationship.

In addition to leading Medigap Plans of America, Kris is the Owner and Managing Partner of Global Health Benefits, where he helps individuals, families, and business owners design smart, sustainable health insurance and employee benefits strategies. He is also the owner of GreatFlorida Insurance of Juno Beach, providing comprehensive property and casualty insurance solutions throughout Florida.

Kris is also the Founder of Cowles Retirement Income Solutions, a firm dedicated to helping retirees and pre-retirees build reliable, tax-efficient income strategies. Through this platform, he specializes in addressing key retirement risks-including longevity, market volatility, and withdrawal strategies-and has trained hundreds of financial advisors and insurance professionals on effective retirement income planning.

He began his career in the late 1990s, opening an Edward Jones investment office in Oswego, New York, while attending the State University of New York at Oswego. He graduated with degrees in Economics and Business, building the foundation for a long and successful career in financial services and risk management.

Kris went on to advance his career with INVESCO Funds, working in both the Atlanta and Denver offices, before serving as Regional Vice President for ING and Allianz in Seattle. In these leadership roles, he partnered with financial advisors and institutions to develop growth strategies and deliver sophisticated retirement and investment solutions.

After years in corporate leadership, Kris relocated to South Florida to build his own firms, with a strong emphasis on independence, client advocacy, and relationship-driven service. Today, his companies serve clients nationwide, focusing on clarity, education, and personalized planning.

Beyond his professional work, Kris serves as Chairman of the Board of the Village of Tequesta Public Safety Pension Board, overseeing governance for the community's police and fire pension system. He and his wife, Jamie, live in Tequesta with their four children-Henry, Jonah, Emerson, and Bodie.