The Federated Challenge^® two-day gala and golf event is hosted by Nick and Jessica Lower of Federated Insurance. 

The Federated Challenge was founded in 2005 by then-Federated Insurance Chairman Al Annexstad and his wife Cathy with the goal of bringing together outstanding corporate citizens and private individuals to support the life-changing work of the Big Brother Big Sisters organization. Upon the Annexstads' retirement in 2012, Federated Chairman Jeff Fetters and his wife Marty began hosting the event. Under their leadership, the Federated Challenge grew into the largest private charity event in the state of Minnesota, and total funds raised since 2005 exceeded $57 million. When Jeff Fetters retired in 2024, Federated Chairman Nick Lower and his wife Jessica assumed leadership for this incredible 20+ year fundraising tradition.

Federated Insurance offsets expenses so 100 percent of the money raised through the Federated Challenge goes directly to Big Brothers Big Sisters. A portion of the proceeds goes to the Federated Challenge Scholarship Program.