Stuart got his start in politics in his home state of Mississippi, where he worked for the future governor, Ray Mabus. Stuart joined Winning Connections in the 2004. Prior to returning to politics, Stuart, who received an MBA from the University of Pittsburgh, managed major car dealerships in the Pittsburgh area. He has a BA in Finance from the University of Mississippi.

At Winning Connections, Stuart has worked on behalf of clients in hotly contested elections, including Senators Jon Tester and Al Franken. Stuart has also managed programs for several top-targeted congressional campaigns, including the races of Representatives Mark Schauer, Martin Heinrich and Mary Jo Kilroy. In addition, Stuart works with advocacy groups on ballot initiatives and elected officials on constituent outreach.