Prior to Navy, Whitehead spent nearly three years at Southern Miss as an assistant director of media relations. In addition, he worked at the University of North Florida (2009-13), where he was promoted to publications coordinator in 2011.
Whitehead served as a graduate assistant at the University of Louisiana at Lafayette from 2005 to 2009 after interning with Georgia Tech (2003-05). He worked for a year as an intern for the Greensboro Bats Minor League Baseball Team (2003) in Greensboro, N.C. and operated as a student assistant in the sports information department for four years while at Georgia Tech (1999-02).
Whitehead received his undergraduate degree in management in 2002 from Georgia Tech and attended graduate school at Louisiana-Lafayette majoring in public relations. He is a member of the College Sports Information Directors of America (CoSIDA), the National Collegiate Baseball Writers of America (NCBWA), and a former member of the Louisiana Sports Writers Association (LSWA). In addition, he is a member of Phi Kappa Sigma fraternity. Whitehead is married to Ginny Puddister and the couple resides in Baltimore.