Bill Gerstein

“My favorite work experiences are when I’m part of a team that is focused and committed to getting useful work accomplished. No matter what my role, I always hope my work will make neighborhoods better places to live and work.”


Bill is a committed and thoughtful advisor with a unique perspective stemming from his work in the pre-college education and community development sectors, and as an entrepreneur. Bill began his career as a Chicago Public Schools high school social studies teacher and track coach before taking over a small chain of supermarkets as an owner and operator. He then completed a master’s in school administration, and worked within CPS and as a high school principal. Bill’s work as an entrepreneur on the south side inspired him to become actively involved in community development, which led to positions as director of community relations for the Hyde Park Cooperative and executive director for Partners in Development in Bronzeville. Working with the community and a group of teachers, Bill organized high schools in the South Shore and Austin neighborhoods, serving as co-founder and principal of these two neighborhood schools. Before joining Conlon Public Strategies, Bill led a major effort within Chicago Public Schools to create comprehensive engagement strategies in the South Side and West Side communities.


  • Board member of City Year Chicago, Firehouse Community Arts Center, and Woodlawn Children’s Promise Community
  • Leadership Greater Chicago fellow and senior advisor
  • Crain’s Chicago Business Forty under Forty
  • Prior board president of Seminary Co-op bookstores


Bill received his bachelor’s degree in history from the University of Wisconsin and his master’s degree in school administration from the University of Illinois Chicago.