Welcome Simon Hess
The Crossroads Board of Trustees is extremely pleased to announce that Simon Hess has been appointed President of Crossroads.

As a lifelong youth and education advocate, Simon has spent his career working to ensure youth from all communities have equal access to the resources, opportunities, and relationships that help them reach their full potential.

“We are incredibly fortunate to have Simon join us as the next leader of Crossroads,” said Kevin Phelan, board chair. “Simon’s combination of thought leadership, hands-on experience, and tireless advocacy will help Crossroads build upon our past successes as we strive to increase our impact for the youth we serve.”

Simon joins Crossroads from his most recent position as Executive Director at Summits Education. Prior to this, Simon was Chief Program Officer at Boston Plan for Excellence and CEO at ChicagoRise and Civitas Schools in Chicago. Earlier in his career, he held leadership positions at Boston Public Schools/Madison Park Technical Vocational High School and worked for the Boston Private Industry Council.

Simon earned a Bachelor of Arts in Religious Studies from College of the Holy Cross; a Master’s in Administration, Planning and Social Policy at Harvard University Graduate School of Education; and an MBA from Kellogg School of Management, Northwestern University.

“I am honored to be joining Crossroads and truly inspired by the transformative impact of Crossroads’ long-term empowerment programs on the lives of young people,” said Simon Hess. “I look forward to working side-by-side with our talented staff in service of the Crossroads mission and am grateful to Deb Samuels for her leadership in building Crossroads into the thriving organization it is today.”

Deb Samuels, outgoing president, is leaving Crossroads in February after 17 years of dedicated service and devotion. Deb and her husband are moving to her native Australia. During her years with Crossroads, including 11 years as president, Deb has been instrumental in leading the organization through a time of unprecedented growth. A recent Boston Globe article on her tenure at Crossroads can be found here.