In 2005, Hildebrand joined with Paul Tewes to form Hildebrand Tewes Consulting, a campaign consulting firm with offices in Washington, D.C. and Sioux Falls. In 2004 he was the campaign manager for U.S. Senator Tom Daschle's (D-SD) losing re-election effort against U.S. Representative John Thune (R-SD). He was also campaign manager in U.S. Senator Tim Johnson's (D-SD) winning re-election campaign in 2002 and Al Gore's 2000 Iowa Caucus victory. He has served as Executive Director of the South Dakota and Minnesota Democratic Parties and Political Director of Democratic Senatorial Campaign Committee. He returned to his private consulting firm following Obama's victory in the 2008 presidential election. After the election Hildebrand defended Obama against left-wing criticism of his centrist cabinet picks in a controversial commentary for the Huffington Post.