Before becoming CEO of Beaches Habitat for Humanity, Cuddihee spent more than 20 years in leadership roles across several staffing firms, including CSI Companies. He joined CSI as Director of Business Development in 2013.

Over the years, Cuddihee established a large philanthropic footprint across the First Coast as a leader and board member of organizations such as JAXUSA, North Florida School of Special Education, San Marco Rotary, Big Brothers Big Sisters, and Beaches Habitat for Humanity.