Job Description

The Dean of Student Life will be a member of the school's Leadership Team, working closely with the Headmaster to plan and implement student life initiatives. This includes planning retreats, field trips and in-school special events; assisting in the Formation program, including the Virtue curriculum; and coordinating clubs. It also includes communicating with students and families about student life events and initiatives. The Dean of Student Life will also be a teacher, and be tasked with delivering excellent instruction in a way that communicates Chesterton's mission and vision. Essential skills for this role include expertise in the subject matter, thoughtful lesson planning, effective organization, clear communication, practical wisdom, and the ability to create a classroom atmosphere that fosters joy, respect, order, wonder, and active participation. Strong applicants must be animated by a spirit of wonder and the desire to grow intellectually, professionally, in character, and in faith. Having taught or previously been educated in classical schools is desirable. Chesterton is committed to supporting the ongoing intellectual, professional, and spiritual formation of teachers, and provides teacher coaching, an intentional culture of growth, a robust school culture that goes beyond the classroom, and opportunities for fellowship and community outside the regular school day. Teachers and school leaders take an Oath of Fidelity to the Magisterium of the Catholic Church. As part of our modeling for students, part-time teachers are encouraged to attend daily Mass at the school when possible. Interested individuals should familiarize themselves with our school and our mission via our website: and then apply by sending materials (see below) to: [REMOVED - SEE ORIGINAL LISTING] Our Lady of Hope's mission is to form young men and women who know and love the truth, and magnify Jesus Christ, Truth himself, with their lives. Through study of the enduring works of the great tradition, a study guided and fulfilled by the light of the Catholic faith, we educate the whole person -imagination, intellect, and will - in wisdom and virtue. We partner with parents to foster a community of learning, prayer, and friendship, centered in the Eucharist, so that our students become joyful leaders and saints. Application Please send the following materials to [REMOVED - SEE ORIGINAL LISTING] Applications are reviewed on a rolling basis. For full consideration please submit as soon as possible May 8, 2025.

• Resume/curriculum vitae
• Cover letter. Your cover letter should answer the following questions:

• 1) What relevant experience do you have with teaching and forming children and young adults? Have you worked with large groups of children and young adults?
• 2) Describe your vision for the way student life initiatives (e.g. field trips, events, clubs, house activities, Formation curriculum etc.) form student culture.
• 3) What are you interested in teaching and able to teach? Note that full-time teachers must teach multiple different subjects.
• 4) Why are you interested in applying to CAOLH?
• 5) What relevant experience do you have with classical education? (Did you go to a classical school? Have you taught at one? Are you self-taught in reading from the Great Tradition, e.g., from Homer and Plato through Flannery O'Connor?
• 6) What are the characteristics of excellent teaching?

• References. Please share the names of 3 people we may contact as references. At least one of your references should be able to comment on each of the following areas: (1) your character and faith, including your leadership ability; (2) your intellectual and academic interests and capabilities; (3) your personal organization, competency, and professionalism.

Job Tags

Full time, Part time,

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