New Executive Director Joins Chesterton Academy

Christopher Olley Brings Extensive Experience in Teaching, Leadership,
and Administration in Public and Catholic Schools


Chesterton Academy is pleased to announce that Christopher Olley has joined the administration as Executive Director. He joins the Academy as it begins its 11th year of operations.

Mr. Olley has extensive experience in public and private Catholic school teaching and leadership. Most recently, he served for 10 years as the President of Saint Catherine’s High School in Racine, Wisconsin, an urban Catholic school serving 690 students from grades 6-12. While at St. Catherine's, Mr. Olley increased enrollment and strengthened faculty and staff. He also oversaw the opening and successful growth of Saint Catherine’s new middle school, establishing a wait list after its first year. 

Mr. Olley started his career as a teacher, coach, and administrator in the Saint Paul Public Schools. During that time he served as the Varsity Boys’ Basketball coach for seven years. He holds a Master of Arts in Education from Viterbo College and a Bachelor of Arts from the University of Wisconsin-Eau Claire. He and his Jane have four children. They live in Woodbury and attend the parish of St. Ambrose.

In his role of Executive Director, Mr. Olley will be part of the Academy's leadership team and oversee all fundraising, public relations, and community outreach for the school. In addition to his duties as Executive Director, Mr. Olley will also serve as the Boys' Basketball coach.

Mr. Olley replaces Mrs. Emily de Rotstein, who has served as Executive Director of Chesterton Academy for the past nine years.  Mrs. de Rotstein is taking on new duties as the Executive Director of the growing Chesterton Schools Network. A partnership between the American Chesterton Society and Chesterton Academy, the Chesterton Schools Network inspires and encourages parent-led Catholic schools across the nation.