Our President

Simon Hess


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On November 27, 2023, Simon Hess was appointed president of Gulliver Preparatory School. His tenure as Gulliver’s second president began on January 29, 2024.

Simon joins Gulliver Prep from his most recent position as 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 Kellogg School of Management, Northwestern University; a master’s in administration, planning, and social policy from Harvard University Graduate School of Education; and a Bachelor of Arts from College of the Holy Cross.

He and his wife, Julie, are eager to join our vibrant and warm community. They have two daughters who are very excited to regularly visit them in Miami. Caroline is a recent graduate of Williams College and is now a consultant with Bain & Co. in Dubai, while Isabella is a junior at the University of Southern California.

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