Bennett is the daughter of former University of Wisconsin–Green Bay Phoenix, Wisconsin Badgers and Washington State Cougars head coach Dick Bennett. Her brother is former NBA player and now Virginia Cavaliers head coach Tony Bennett. She graduated from Stevens Point Area Senior High School in Stevens Point, Wisconsin and attended the University of Wisconsin–Stevens Point and the University of Wisconsin–Green Bay, where she played on the women's basketball teams at both schools.
Bennett served as a head coach at Marycrest College during the 1988–89 season before taking the same position at the University of Wisconsin–Oshkosh. During her time there she led the team to the 1996 National Championship and was named Coach of the Year that season. From there she was assigned the head coaching position with the Evansville Purple Aces and the Indiana Hoosiers. After spending a period of time away from coaching, she became an assistant coach with the Wisconsin Badgers before being hired to the head coaching position with the NIU Huskies.