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Headmaster Chris Post announces Amy Wesloski as our next head of upper school

Headmaster Chris Post announces Amy Wesloski as our next head of upper school

Dear Boys’ Latin Families, 

I am pleased to announce the appointment of Amy Wesloski as our next head of upper school, effective July 1, 2023.  Amy is a distinguished school administrator with more than 20 years of leadership experience.  She previously served as principal of Chesapeake High School, responsible for the day-to-day management of more than 1,000 students and supervising more than 100 faculty and staff members. During her tenure, she led the school through the pandemic, ensuring continuity of learning for students while building strong connections with families.  Amy joined our faculty this fall, teaching science in the upper school, serving as an advisor, and as a member of our residential life faculty team in the boarding program. While only in her first year as a member of our faculty, Amy quickly established herself as a dedicated and hard-working professional, embodying our mission in her daily interactions with students and colleagues alike. It was her return to the classroom – and her direct experience with our boys – that compelled Amy to seek the opportunity to lead the upper school.

Reflecting on her appointment as head of upper school, Amy shared the following comments. “First stepping onto campus over five years ago as a parent and most recently, this fall, as an upper school faculty member, I continue to marvel at what a special place Boys’ Latin is for our boys.  I am grateful for the opportunity to lead the BL upper school and will continue the good work occurring on Lake Avenue, honoring Boys' Latin's rich history, and creating new experiences that will empower our boys to reach their full potential.”

Beginning in November, we launched our search, working in conjunction with our partners, The Finney Search Group.  We reviewed the materials of more than 40 applicants and interviewed a dozen candidates prior to winter break.  Heads of school, division heads and principals – all talented school leaders locally and nationally – spoke passionately about the opportunity to lead our upper school.  They reflected on the character of your sons, the dedication of our outstanding faculty, the tremendous support of our families, and the distinctive culture of Boys’ Latin that prides itself on forging enduring personal relationships.  Three finalists visited campus late in January, meeting with trustees and parents, faculty and administration, and most especially, our boys.   

Amy emerged as the leading candidate, as constituents commented on her focus on process and systems, her warmth and directness, and her purposeful leadership.  Her experience as a faculty member gives her a first-hand view of the challenges and, especially, the opportunities that lie ahead.  Amy spoke passionately about creating connections across the curriculum that promote academic excellence, providing ample opportunities for our boys to build leadership skills and to further foster character development.  Her references commented that she is an inspirational leader who models the best in teaching and learning for staff and students alike.  

Others commented on her uncanny ability to build lasting relationships across the entire community – understanding the delicate balance between being student and faculty centered while holding all to equally high standards.

I am so very grateful for the many members of our community who participated in this comprehensive process.  I appreciate the efforts of our students, our faculty, staff and administration, our parents and our trustees who have given so generously of their time and energy, meeting with candidates and providing their insights and perspectives.  This active involvement in the process is a wonderful testament to the engagement of our community and the strength of our School.  I am especially grateful for the extraordinary leadership of Brandon Mollett ’94, who has tirelessly led the upper school as interim head this year, ensuring that our boys and our entire community continue to be well served. Through the transition and as head of upper school, Amy will work closely with me and with Brandon, who will return to his position as academic dean at the conclusion of this academic year.  

Amy earned her undergraduate degree from King’s College (PA) and her graduate degree from Notre Dame University (MD).  No stranger to our community, Amy, and her husband Neal, are parents of Brady, class of 2025.  

Amy brings a wealth of experience, an unmatched enthusiasm for our School and a lived experience of our mission.  We will be scheduling a parent session to meet Amy following Spring Break.  In the meantime, please join me in congratulating her on her appointment, and, as always, please let me know if you have any questions.


Christopher J. Post