Gary Raeckers

Sr. Advisor

Gary Raeckers brings over 40 years of senior management experience to his new role at Skyway as a Senior Advisor, working directly with senior leadership on enhancing the operational functions of the firm, maintaining compliance oversight and overseeing the implementation of company strategies.

Gary is a seasoned professional holding a variety of leadership positions over decades.  Most recently from 2010 – 2021, he held multiple roles at Benefytt Technologies, a health insurance innovation company including Chief Operating Officer and Sales Team lead.

Gary also served as the President and CEO of Plan Services, a third-party administrator for health insurance plans.

Mr. Raeckers resides in Tampa, Florida and attended the University of South Florida.