Tommy is a Washington, D.C.-based international affairs executive with nearly two decades of professional experience as a nonprofit leader, strategic business consultant, attorney, and schoolteacher. He has traveled to Cuba over 25 times to facilitate people-to-people engagement and support the Cuban people as well as to advise companies exploring business opportunities. 

Most recently, he served as Executive Director of the Caribbean Educational and Baseball Foundation, a 501(c)(3) that used baseball to support youth development and build cultural bridges between the U.S., Cuba, and other parts of the Caribbean. Previously he worked as an Associate Vice President at The Cohen Group; an attorney at Wilson Sonsini Goodrich & Rosati and within the U.S. federal government; and as a teacher at the Lincoln School in Costa Rica.

Tommy received both a J.D. and B.A. from the University of Virginia. He also earned a Sports Philanthropy Executive Certificate from The George Washington School of Business.