Mr. Caldwell serves as the Executive Vice President for Midlands. He has been very active in Midlands’ boat program and is responsible for underwriting and marketing both yacht and small watercraft insurance in all states in which the company is licensed. Prior to joining the company in August of 2001, Mr. Caldwell interned in various departments of Midlands and was also employed at a large boat dealership in the Dallas, Texas area.  During the summer of 2007 he interned in various departments at the offices of Arthur J. Gallagher (UK) Ltd., London. Mr. Caldwell attended Southern Nazarene University in Oklahoma City, OK and Collin County Community College in Dallas, Texas.

Mr. Caldwell travels regularly to London as Midlands’ liaison to the world’s foremost insurance marketplace. Mr. Caldwell has attended the annual Ft. Lauderdale Mariners Club conference for the past five years. He is a frequent attendee of the AAMGA and NAPSLO annual meetings, attends various events sponsored by the Independent Insurance Agents and other insurance industry related conferences and agent events.