Caldwell has more than 30 years of experience in the group and individual life, health and disability insurance and self-funded industry. She also has extensive operational and management experience in claims and regulatory compliance.
Caldwell holds a J.D. from the University of Wisconsin Law School and a B.A. in History from the University of Wisconsin-Madison. She frequently participates as a mock trial judge for the annual State of Wisconsin High School Mock Trial Tournament; and as a judge for the Business and Ethics segment of the annual state DECA competition. Caldwell resides in Merrimac, Wisconsin.