Mr. Caldwell was born and raised in San Antonio, Texas (USA). He attended the University of Texas at Austin. In 2001, he graduated with a degree in History. His teaching career began in August of 2001 working at a charter school servicing at-risk students in Austin, Texas. After two years in Austin Mr. Caldwell taught for three years in the Houston Independent School District before he and his wife took their first international posting at Almaty International School in Almaty, Kazakhstan.
They spent three years in Almaty before moving to the American International School of Chennai where they taught for three years. He received his M.ED in Educational Leadership in August 2011. Mr. Caldwell joined ISG in 2012 working at Yanbu International School. He taught high school social sciences during the 2012-2013 school years. In August of 2013, Mr. Caldwell became Assistant Principal of YIS. Mr. Caldwell joined DHS in 2015.