Caldwell Trust CEO wins statewide industry award

Sarasota financial services entrepreneur Kelly Caldwell, who is president and CEO of Caldwell Trust Co., has been named the Florida Bankers Association 2025 Trust Banker of the Year.  

The announcement was made during the FBA’s 66th Annual Trust & Wealth Management Conference in Fort Lauderdale, according to a statement. The award, the FBA says, is presented to “to an individual who has distinguished themselves during the previous year with dedicated service to the FBA, and to the Florida trust and wealth management industry. 

Caldwell’s father, the late Roland Caldwell, founded the firm, which received its charter from the State of Florida in 1993. “When Roland retired in 2007, Kelly succeeded as CEO, continuing his father’s dream. Through his dedication to excellence and hard work, the company has continued to grow and thrive,” Trust Division Chair Carlos Batlle says in the statement. 

The company manages around $2 billion in assets and has some 50 employees. It also recently opened an office in Vero Beach. 

“While Kelly’s business success is undeniable, his dedication to his community and his industry truly set him apart,” FBA President and CEO Kathy Kraninger says in the release. “He consistently makes time to serve his local community and support others in the trust industry. The FBA, and the Florida trust industry, have benefited from Kelly’s service on our Trust Executive Committee Board, where he generously shared his time and knowledge.” 

Caldwell was one of five people to win an award from the FBA’s Trust Division, the release states. 

Established in 1888, the Florida Bankers Association represents more than 150 banks of all sizes, covering more 134,000 employees.