StC News

Announcing the Next Head of Upper School

We are thrilled to announce that Jake Westermann will become the next Head of the Upper School at St. Christopher’s.
December 1, 2022

Dear Saints Families,
It is with great excitement that I announce that Jake Westermann will become the next Head of the Upper School at St. Christopher’s. Jake currently serves as the Director of Student Life at the Potomac School (K-12, 1066 students) in McLean, VA, and will assume his duties in July 2023.

We were blessed with an abundance of talented and experienced candidates for this important leadership role. Throughout the interview process, which began in September, Jake distinguished himself with his relevant experience at three excellent independent schools, his commitment to student and faculty growth and wellness, and his extensive teaching and coaching experience at the Upper School level. 

In speaking with present and former colleagues and supervisors of Jake, it is clear that St. Christopher’s is gaining an exceptional educator and leader, and I am excited for Jake and his family (wife, Susie, and two young sons and a daughter) to make a positive impact on the St. Christopher’s community for years to come. Jake’s direct work with young men, as a dorm parent, teacher, coach, and administrator, emerged as a particular strength throughout the interview process.
“I could not be more excited about joining St. Christopher's as the next Head of Upper School,” Jake said. “During my time on campus, I could immediately discern the strength of the relationships between the adults and the students, the excellent teaching, and the character of the boys. 
"Many institutions tout their sense of community, and in every conversation I had about St. Christopher’s, it became abundantly clear how genuine and enviable yours is. I am eager for my family to arrive in Richmond and to work alongside the gifted teachers, the strong administrative team, and the talented young men.”
Jake currently oversees all aspects of student life in the Upper School and also supports the growth and development of one-third of the Upper School faculty. Before moving to Potomac, Jake was on the faculty for five years at St. George’s School in Middletown, RI (9-12, day and boarding, 370 students), teaching English and history. He served as the Director of the St. George’s School Teaching Fellows Program and the Director of Global Studies. In these programs, Jake developed curriculum, managed program budgets, authored the St. George’s School Professional Teaching Standards, coached lacrosse and basketball, and served as a dorm parent. 

Jake began his career as a Middle School teacher at Shore Country Day School in MA. Jake received his Bachelor of Arts in modern American history from Brown University, where he also served as captain of the lacrosse team and earned Academic All-American distinction. Jake holds a Master of Arts in Liberal Studies from Dartmouth College.

Jake said, “Kim Hudson and Tony Szymendera have led an exceptional Upper School and leave massive shoes to fill; I look forward to continuing their excellent work. I can't wait to hit the ground running this summer and begin my tenure as a Saint.”

I will close with words of thanks to Dr. Kim Hudson, who has done–and will continue to do–exceptional work this year as our Interim Head of the Upper School. In the weeks to come, Dr. Hudson and I will be finalizing a new role for her at St. Christopher’s, one that maximizes her impact on our boys, faculty, and families. We are truly blessed to count such an exemplary educator as one of our own.

I also wish to thank our outstanding Upper School Head Search Advisory Committee (listed below) and Carney, Sandoe, and Associates for their support and good counsel throughout this search process.
Jake and his family will be on campus several times this winter and spring as part of the transition process. We will create opportunities for Jake to connect directly with students, faculty, and parents and will keep you informed of those events as they are finalized.

Thank you for your continued support of St. Christopher’s. 

Mason Lecky
Upper School Head Search Advisory Committee
Emmett Carlson, Upper School Math Teacher, Upper School Academic Scheduler 
Ed Cowell, Assistant Head of School for Community Engagement 
Jim Jump, Director of College Counseling and Upper School Academic Dean 
Sarah Mansfield, Assistant Head of School 
Billy McGuire '85, Upper School Science Dept. Chair and Biology Teacher 
Alex Nicoll '97, Upper School Spanish Teacher 
Ann Vanichkachorn, Director of Health and Wellness 
Jay Wood, Upper School English Dept. Chair, English Teacher  
Elsa Woodaman, Upper School French and Spanish Teacher and Dir. of X-Term 
Karen Wray, Upper School Dean of Faculty, French and Religion Teacher
711 St. Christopher’s Road Richmond, Virginia 23226