Prior to college, Dennard served as the chairman of the Arizona Teenage Republicans and spoke at the 2000 Republican National Convention in Philadelphia. He was featured with Sean Combs for a TV special and interview at the 2004 Republican National Convention. Between 2005 and 2009, Dennard worked for U. S. President George W. Bush, including at the Office of Legislative Affairs, the Office of Political Affairs, and the Office of Public Liaison. During that time, he served as White House Director of Black Outreach; coordinated the meetings and travels of the President, First Lady Laura Bush, and the House of Representatives; and planned various events in the White House. Between 2009 and 2011, Dennard worked at the Republican National Committee as an Associate Director for Coalitions.