Weiland graduated from the University of South Dakota. While in college, he worked on Tom Daschle’s first Congressional campaign in 1978 and continued working for him until 1996 when Daschle ran for Congress. He has served as FEMA regional director, the state director for the AARP and COO and CEO for the International Code Council, which is the nation’s leading advocate for uniform building codes and building safety. He and his wife also operate a restaurant in downtown Sioux Falls.
Weiland is running in the 2014 election for the U.S. Senate, representing South Dakota. Weiland ran unopposed in the Democratic primary on June 3, 2014. The general election takes place November 4, 2014.
Weiland has yet to win the support of Harry Reid and the Democratic Senatorial Campaign Committee, despite being the only registered Democratic in the race as of December 2013. Weiland met with Reid's Chief of Staff David Krone, leading Weiland to believe Reid was warming up to him, "I think he’s got a job to do at this point, which is his job as majority leader, and he is not dictating to the Senate campaign committee. That’s Michael Bennet’s purview, obviously. They don’t want to get their signals crossed, and they want to be able to coordinate their efforts." However, Reid's staff denied this saying, "Not much to see here. David took the meeting as a favor, but Senator Reid’s stance hasn’t changed."