Oct 14, 2021


  • Trinity Executive Partnership
  • Hopkins, MN, USA
Full time Education: Middle/High School

Job Description

Trinity Executive Partnership is assisting Chesterton Academy of the Twin Cities in the recruitment of a new Headmaster.

Chesterton Academy of the Twin Cities is a private, co-ed, Catholic secondary school in Hopkins, Minnesota. It is located in the Roman Catholic Archdiocese of Saint Paul and Minneapolis. Launched in 2008, the Academy is centered on G. K. Chesterton's (the great English writer and Catholic convert) ideas of integrated learning. The founding school is part of the Chesterton Network of Schools; currently there are 27 schools in the U.S. and Canada, with several additional schools slated to open in 2021.

Chesterton Academy's classical curriculum combines a broad, liberal arts education with a strong emphasis on the development of Christian virtues and an appreciation of beauty. All students at Chesterton Academy enjoy a cohesive, content-rich education through studies in Humanities, Math & Science, and the Fine Arts including four years of Theology.


The Headmaster's primary focus is Vision/Mission and Academics; however, the Headmaster is responsible and accountable (to the Board of Directors) for every critical aspect of the School's operation and development, including: Finance, Administration, Recruiting, Public Relations, and Development.

The Headmaster will also manage the school's faculty and staff, and have a strong sense for which matters require direct attention and which can be appropriately delegated.

Vision & Mission:

-Live, lead, and enhance our central mission: the formation of each student's character, intellect and spiritual life
-Develop students that will love and courageously defend the Catholic faith and act as a counter-cultural force for faith, truth, and beauty
-Recruit, manage, develop, and retain excellent faculty and staff


-Ensure ongoing quality and delivery of our unique Chesterton Classical Curriculum
-Partner with faculty to develop best practices to achieve our goals for academic excellence
-Perform documented observations of faculty, updating the faculty evaluation and review process, and ensuring faculty professionalism and accountability

Administration & Finance:

-Oversee all administrative and financial staff and functions
-Provide ongoing staff development
-Drive and oversee development of annual school calendar and all related activities
-Create and manage an annual budget in partnership with key staff and faculty

Recruiting & Public Relations:

-Drive strong positive Chesterton public relations and advance the Chesterton "brand"
-Develop and deliver annual recruiting objectives
-Work closely with the Director of Admissions & Recruitment to actively manage enrollment process to ensure growth while maintaining admission standard consistent with the rigor of our curriculum


-Develop and deliver key annual fundraising objectives
-Cultivate strong relationships with key donors
-Ensure continuing excellence and execution of Annual Chesterton Gala


-Faithful Catholic dedicated to living and teaching the beliefs of the Catholic Church
-Undergraduate degree required; advanced degree in relevant field preferred
-Strong leadership and management experience, preferably in an academic setting
-Demonstrated success in driving growth
-Demonstrated excellence in communication
-Demonstrated ability to recruit and retain a strong team
-Experience and success building strong relationships with parents, families, clergy, diocesan partners, etc.


-Experience with classical education and curriculum
-Clear understanding and strong commitment to the continued actualization of the Chesterton Academy Vision and Mission
-Teaching experience
-Demonstrated success in benefactor development
-Demonstrated achievement in driving enrollment
-Business management experience

For inquiries or to submit a cover letter and resume, please contact: m.kane@trinityexecutivepartnership.com.

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