James Jessup is New Head of Middle School

Head of The Seven Hills School Matt Bolton has announced that James Jessup has been selected as the next Head of Middle School after a nationwide search.

Jessup comes from The Westminster Schools in Atlanta, where he was most recently the dean of students and the director of the summer program. Jessup will be taking over for Bill Waskowitz, who, after leading the Seven Hills Middle School for 15 years, is going to the Jackson Hole Community School in Wyoming to establish their middle school division.

Jessup will start as the Head of Middle School in the 2025-26 school year. In addition to his current roles at The Westminster Schools, Jessup has also served as a social studies teacher, grade chair for sixth grade boys, and a basketball coach.

“As a basketball coach and history teacher, James understands and values the interplay between academics, athletics, and the arts,” Bolton said. “He has transformed his middle school’s approach to discipline and student behavior by adopting a restorative approach, created programming to build community and student leadership.”

Jessup has a B.A. in middle grades education and history from University of North Carolina at Greensboro, an M.A. in curriculum and instruction from UNC at Charlotte, and is working on a doctorate in organizational leadership and learning from UNC at Chapel Hill.

Before joining Westminster Schools, Jessup worked for the Children’s Home Society of North Carolina, founded and directed Camp Clutch, was assistant director and African American outreach specialist for the Crosby Scholars Community Partnership, and taught sixth through eighth grades.

“I look forward to working alongside a dedicated team of educators who understand the unique journey of middle school and are committed to meeting students where they are. Together, I’m confident we will continue nurturing a culture that celebrates growth, connection, and the limitless potential of every student,” Jessup said.

The Seven Hills Search Advisory Committee was co-chaired by Middle School teacher Mandy Hayes and Director of Admission, Grades 6-12 Nancy Clark. During his visit to Seven Hills, Jessup met with parents, teachers, students, and administrators, with many remarking on his passion for middle school education and community.

“From my very first visit, I felt an unmistakable energy from the students — a spirit of curiosity, joy, and authenticity that made a lasting impression. It’s clear that Seven Hills is a community where students, families, and educators partner with the intention to create an environment where young people can truly flourish — academically, socially, and emotionally,” Jessup said.