Website The Chesterton Academy of St. John the Evangelist Charlottesville, Virginia


The Chesterton Academy of St. John the Evangelist in Charlottesville, VA, is looking for a dynamic individual to join our efforts to launch our school in Fall of 2024. Applicants must uphold and advance the school’s Catholic, classical mission and philosophy. This position is responsible for overall administration and leadership of the school including, but not limited to, managing, hiring, and developing exceptional faculty members; overseeing instructional strategies and curriculum unique to the Chesterton Academy; effectively communicating with parents; overseeing all aspects of student life, including discipline; managing the policies, regulations, and procedures to ensure that all students are supervised in a safe learning environment that adheres to our Catholic identity; promoting the school within the community; overseeing student admissions; facilitating growth and management of new families, and working closely with the Board of Directors to identify goals and fulfill their strategic plans; and teaching classes as needed.

All applicants must be practicing Roman Catholics and must inspire and exemplify Catholic doctrine and morality in a manner consistent with the teachings of the Magisterium of the Catholic Church. We are looking for a joyful, prayerful servant leader who is not only a capable administrator, but also one who loves young people and has a passion for the formation of the whole human person. The applicant must know how to hire and develop faculty who can effectively teach, love, and inspire their students. As the head of the school, he or she should work to create a culture for students, faculty, and staff that facilitates a genuine encounter with Jesus Christ.

The ideal candidate would have a Master’s degree in education or related field, as well as significant teaching experience in a classical school environment, previous experience in secondary school administration, and familiarity with the mission of Chesterton Academy and the teachings of the Catholic Church.

Salary is competitive and commensurate with experience.

Primary Responsibilities and Duties

Curriculum and Academic Excellence

  • Oversee adherence to Chesterton Schools Network (CSN) curriculum
  • Oversee implementation of CSN-directed changes to curriculum
  • Use assessment data to monitor the effectiveness of the academic program on student learning,
  • Oversee school accreditation process and renewal per Network guidelines


  • Oversee faculty hiring, training, evaluation, rehires, and terminations
  • Conduct classroom observations for faculty members as part of evaluation process
  • Oversee the ongoing development of teachers in accordance with a distinct vision for excellence in their professional craft

Student Life and Discipline

  • Shape the student culture to strive for virtue, character, and encounter with Christ
  • Ensure discipline policies are communicated and enforced
  • Oversee parent-led sports and extracurricular activities
  • Ensure effectiveness of the house system and faculty mentor programs

Parent Communications

  • Maintain effective communication and partnership with parents
  • Meet with parents regarding academic issues and student discipline


  • Oversee admissions process for new students
  • Review placement tests and contact parents with remedial needs
  • Deliver presentations to prospective parents and students at selected school events


  • Coordinate standardized testing, college applications and transcript preparation
  • Communicate with colleges, universities and other post-high school programs
  • Promote various vocational opportunities

Other School Operations

  • Supervise business manager and administrative staff
  • Oversee selection and evaluation of vendors (software, textbooks,
    other services)

Teaching Responsibilities (as needed)

About Chesterton Academy

Founded in 2008 as a result of a grassroots movement of parents, Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. Focusing on the classics, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more about Chesterton Academy and the growing national Chesterton Schools Network, as well as Chesterton Academy of St. John the Evangelist. 

If interested in applying, please send your resume and cover letter to Victoria Lannon, Vice Chair, at

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