Dean of Student Life

Dean of Student Life Overview

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. Responsibilities include planning and overseeing mission‑aligned student events (clubs, retreats, dances, field trips, Frassati Fridays), ensuring the strong functioning of the house system, coaching and overseeing the prefects, generating and overseeing spiritual formation initiatives, assisting in the Formation program including the Virtue curriculum, serving as the first point of contact for students, faculty, and parents after teachers for discipline, maintaining disciplinary records, communicating with parents about student discipline, and teaching a reduced load as needed.

The Dean will also be a classroom teacher, tasked with delivering excellent instruction that communicates Chesterton's mission and vision. Essential skills for this role include subject‑matter expertise, 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.

• Animated by a spirit of wonder and a desire to grow intellectually, professionally, in character, and in faith.
• Experience teaching or prior education in classical schools is desirable.
• Strong applicants will demonstrate leadership, professional organization, and a commitment to the Catholic faith.

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. We educate the whole person— imagination, intellect, and will— in wisdom and virtue, partnering with parents to foster a community of learning, prayer, and friendship centered in the Eucharist so that students become joyful leaders and saints.

Interested individuals should familiarize themselves with the school and its mission via the website: (Use the "Apply for this Job" box below). Apply by sending the following materials to rduffy. Applications are reviewed on a rolling basis; for full consideration please submit as soon as possible, preferably before May 8, 2025.

• Resume/Curriculum Vitae
• Cover Letter addressing:
  • Relevant experience with teaching and forming children and young adults; experience working with large groups.
  • Vision for student life initiatives and how they form student culture.
  • Subjects you are interested in teaching and can teach (full‑time teachers must cover multiple subjects).
  • Reasons for applying to CAOLH.
  • Experience with classical education (attendance or teaching at a classical school, or self‑taught in classics).
  • Characteristics of excellent teaching.
• References (names of three contacts, at least one for each: character and faith, intellectual and academic interests, and personal organization/competency/professionalism)

Chesterton is committed to supporting teachers’ ongoing intellectual, professional, and spiritual formation, providing coaching, an intentional culture of growth, a robust school culture 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. Part‑time teachers are encouraged to attend daily Mass at the school when possible.