Chesterton Academy Announces the Hiring of Christopher Olley, Current Executive Director, as New Headmaster

Hopkins, MN (May 5, 2022) – Chesterton Academy of the Twin Cities announced today the hiring of Christopher Olley as the school’s new headmaster. Olley has been serving as Chesterton Academy’s Executive Director for the past four years, and he will succeed Dr. Dale Ahlquist, who has served as interim headmaster this past year. Ahlquist is also the President of the Society of G.K. Chesterton and is the co-founder of the school. 

As Chesterton Academy’s Executive Director, Olley worked closely with the headmaster to provide oversight of the entire school budget, fundraising, and community outreach. He also implemented donor management and wealth assessment software while transitioning the school from an events-focused to a relationship-centered fundraising model. In addition to his current role, Olley has volunteered as the girls’ basketball coach.

From teaching, coaching, and serving in a variety of administrative capacities, Christopher Olley has seen nearly every facet of what makes Catholic education tick. Before joining Chesterton Academy in 2018, he served for ten years as the President of his alma mater, Saint Catherine’s High School in Racine, Wisconsin. In his time at Saint Catherine’s, he led efforts to successfully expand enrollment year after year, added a middle school program, and established a proactive fundraising effort that increased the school’s endowment from $2.3 million to $5.2 million, in addition to numerous other academic and developmental accomplishments. Before entering into administration, Olley spent 26 years as a teacher and coach for many different Twin Cities and Wisconsin schools.

A committee made up of parents, teachers, and the school’s advisory board conducted a national search for the new headmaster. “After prayer and careful discernment, in collaboration with the extensive work of the search committee, we have full confidence in Mr. Olley’s ability as an educator and committed Catholic servant-leader for Chesterton Academy,” said Jay Ward, chair of the school’s board of directors. “We’re very happy to have Mr. Olley accept this new position. He has displayed tremendous leadership and engagement with the students, faculty, staff, and parents.” Olley will be the fourth full-time headmaster in the school’s history.

Olley is looking forward to serving as headmaster. “I am eager to get started working closely with our teachers, students, and parents to make our school even better,” he remarked. “I see some growth opportunities for the school that I think we can take over the next couple of years that will take us to new heights.”

Olley will work with Ahlquist, who has been serving as the interim headmaster, to ensure a smooth transition. His tenure as headmaster will begin on July 1. “We’re thrilled to have Mr. Olley as our new headmaster,” said Ahlquist. “He is a proven leader and has a huge devotion to the school and to our families.”

“The board also wants to recognize the outstanding role that Dr. Ahlquist has played in this transition,” said Ward. “We are thankful for his dedication and hard work while serving as interim headmaster, doing so in addition to his leadership of the Society of G.K. Chesterton and his commitments to the Chesterton Schools Network.”

Olley earned his bachelor’s degree from the University of Wisconsin-Eau Claire and his master’s in education from Viterbo College in Lacrosse, Wisconsin.

“I would like to thank Dr. Dale Ahlquist, Jay Ward, and the entire Chesterton Academy board for this opportunity. I am appreciative for the chance to lead such a special Catholic community. The teachers and students make this new role a challenge I just couldn’t pass up. Jane and I feel lucky to be part of the Chesterton family.”

Olley and his wife Jane have four adult children and live in Woodbury. 

More about Chesterton Academy

The mission of Chesterton Academy is to help parents raise up a new generation of joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. Their rigorous, integrated curriculum unlocks students’ potential and prepares them to succeed in college and professional life, and to excel in service of family, of country, and of Christ our Lord. Chesterton Academy serves grades 9 through 12. 
For more information or to schedule a tour of the school, please visit

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