Dean was a Partner at the Center for Workforce Effectiveness and a Consultant at Sibson & Company and at Hewitt Associates. Before that, he was the Director of Marketing Research and Strategy for the Mason Shoe Company.

Dean holds an MBA from Northwestern University's J. L. Kellogg Graduate School of Management and a BA degree in Economics from Lawrence University. He is on the faculty of the University of Illinois at Chicago's Certificate in Business Administration Program, ranked by Fortune as "best in class" in executive education. He has written numerous articles and white papers on a wide range of workforce productivity topics.

Dean serves as Chairman of the Board of the Lattof YMCA located in Chicago's Northwest suburbs. He is also a strategic advisor to the Alliance for Character in Education, a non-profit organization supporting Northridge Prep and The Willows Academy, two of the Chicago area's finest schools for grades 6-12.