Simon joined Gulliver Prep in 2024, his tenure as the President of Crossroads, a recognized leader in Boston’s youth development sector. Prior to this, he was Chief Program Officer at Boston Plan for Excellence and CEO at ChicagoRise and Civitas Schools in Chicago, as well as Principal at Gordon Tech High School, also in Chicago. Simon earned an MBA from the Kellogg School of Management, Northwestern University, his M. Ed. from Harvard University Graduate School of Education, and a Bachelor of Arts from the College of the Holy Cross. He and his wife Julie have enormously enjoyed their transition to Gulliver's vibrant and warm community. They have two daughters who are thrilled to regularly visit Miami. Caroline is a graduate of Williams College and a consultant with Bain & Co., while Isabella recently graduated from the University of Southern California and works at SoLa Impact in Los Angeles.
