The current leadership team at WinningWise has a wide range of experience in human resources, development, marketing, and consulting. The team is composed of individuals who have worked for companies such as Expedia Group, Mondelēz International, Taproot Foundation, ITC Limited, and Northern Illinois University. They have also held positions at SuccessWise Consulting, Inc., IRI, People with Panache, and BPI group. The team's education histories include degrees from Northwestern University, Illinois State University, Drake University, and Western Michigan University.