Hildebrand grew up in Mitchell, South Dakota.
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.
Hildebrand worked briefly for Kendrick Meek in his 2010 candidacy for U.S. Senate from Florida, after a triumphant effort overseeing Obama's Florida campaign in the closing days of the 2008 election. Abe Dyk has since taken over as campaign manager.
Hildebrand had indicated that he might challenge Representative Stephanie Herseth Sandlin in the 2010 Democratic primary, if her vote scuttled health care reform. Hildebrand advised Rapid City physician Kevin Weiland's 11th-hour campaign for South Dakota's Democratic U.S. House nomination in 2010.
Hildebrand is currently the owner/operator of Josiah's Coffee House and Café in Sioux Falls, S.D.
Hildebrand is gay.
- "Obama's inner circle". Chicago Sun-Times. 2008-03-09. Archived from the original on March 12, 2008. Retrieved 2008-03-10.
- Washington Post (2008). The Fix - Hildebrand Returns to the Private Sector. Retrieved December 16, 2008.
- The Washington Post http://voices.washingtonpost.com/thefix/2008/12/hildebrand_returns_to_the_priv.html?nav=rss_blog. Missing or empty
- "Obama campaign guru eyes House seat". CNN. 2010-03-16. Retrieved 2010-05-24.
- Rapid City Journal: Kevin Weiland says it's not about political payback; 'I can win'
- Melloy, Kilian (19 November 2008). "Obama’s Transition Team Includes Seven Openly Gay Advisors". Edge Boston. Retrieved 2008-11-25.