A native of Trinidad and Tobago, Sheldon has been coaching men and women of all ages for the last 16 years. As a player, He represented Trinidad and Tobago in a Caribbean tournament in 1985. He then played first division soccer for four years with Alcons Football Club and Maple Football Club. In 1990, Sheldon was awarded a full soccer scholarship to attend Coker College in Hartsville, South Carolina.

Sheldon has coached college and high school players at elite soccer academies in Virginia, North Carolina, South Carolina, and Georgia. He has coached premier teams at the club level in North Carolina, Virginia and Florida. He is an Olympic Development Program staff coach for the state of Florida. He currently holds a USSF A license and a FIFA certificate.