Gulliver Preparatory School Selects New President and CEO

Home > Gulliver Preparatory School Selects New President and CEO


Simon HessGulliver Preparatory School is proud to announce the selection of Simon Hess as its new President and Chief Executive Officer. His leadership will chart a course to strengthen, support, and refine Gulliver Prep as it continues along its path of being a preeminent, thought leading institution while maintaining its devotion to the individual outcomes of its students, ensuring a legacy that began almost 100 years ago at the school’s founding.

“Gulliver Prep will welcome a proven leader and educator whose lifelong pursuit of excellence has taken him to a variety of institutions across the country,” said Board Chair Scott Davidson. “Not only does Simon have the professional experience leading as a president, CEO, and principal, he also comes to Gulliver with a philosophy that focuses on the individual learner – a principle we have held dear at Gulliver Prep since the remarkable Marian C. Krutulis instilled her vision to create an academic community devoted to educational excellence, with a personal touch, that fulfills each student’s potential.”

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.

“I am thrilled and honored to join the Gulliver family,” said Simon. “In getting to know the school community over the past several months, I have been inspired by the vibrance of its culture, the depth of its attention to the aspirations of each young person, and the power of its commitment to providing an unparalleled educational experience. At Gulliver, it is clear to me that each student is seen, valued, and challenged to step boldly into their learning, act with great heart, and learn to lead wisely. I look forward with great energy and enthusiasm to guiding our community to write the next great chapter in the story of this amazing institution.” 

Simon’s leadership will be crucial as Gulliver Prep continues to fulfill the promise of their capital campaign, Transformation. Together. 2026., and begin preparations to celebrate their centennial in 2026. He will begin his tenure on January 29, 2024, replacing Cliff Kling who has served as Gulliver’s president, the first in school history, since 2018.


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