Dean of Students

About Monte Cassino School:

Embarking on its centennial year, Monte Cassino School, a Catholic, Benedictine, independent, co-educational school in Tulsa, Oklahoma, serves students from Grades PK3-8. Our Early Childhood Learning Center (PK3–K), Elementary School (Grades 1–4), and Middle School (Grades 5–8) together educate over 780 students. Rooted in Benedictine values, Monte Cassino inspires students to lead and serve through lives of purpose that integrate faith, academics, community, and personal growth. Guided by our school motto, “Every day at Monte Cassino School, we do our best so that in all things God may be Glorified,” we cultivate a nurturing, vibrant environment where students are challenged to grow, respected as individuals, and encouraged to discover and develop their unique gifts.

Position Overview:

Monte Cassino School seeks a highly organized, detail-oriented, collaborative, and student-centered Middle School Dean of Students to begin work in July 2026. The Dean of Students will oversee all aspects of student life in the middle school, modeling professionalism, clear expectations, and positive engagement with students, families, and faculty. This role promotes student voice, agency, and leadership, ensures that every student feels seen, valued, and empowered, and models and promotes our JRP (Justice, Respect, and Peace) culture through restorative practices when appropriate.

Key Responsibilities:

• Serve as a hands-on advocate for the school motto and community norms as outlined in the Parent-Student Handbook.
• Encourage student voice and promote student agency, empowering students to take ownership of their learning and school community.
• Collaborate with the Middle School Principal on all matters related to student life and programming.
• Lead, guide, and supervise all aspects of student life, including culture-building, leadership opportunities, and innovative practices in student engagement.
• Organize, lead, and steward the school’s annual traditions, community celebrations, and student life programming that shape the culture and spirit of the middle school.
• Develop mentoring programs and relationship-building initiatives with ECLC and elementary students.
• Lead the middle school advisory program and weekly assemblies, ensuring they are student-centered and provide leadership opportunities.
• Build and sustain a positive school culture through consistent, clear expectations and engagement with students.
• Actively participate in the life of the middle school, supporting events and student initiatives.
• Support the welcome and onboarding of new students and families.
• Maintain the middle school student life calendar and manage the budget.
• Address student comportment and discipline using restorative justice approaches when appropriate, including meetings and communications with faculty and parents.
• Foster an environment where all students feel seen, valued, and a sense of belonging.
• Liaise with admissions to coordinate student panels, shadow days, and open houses.
• Lead student transition activities from elementary to middle school (Grades 4–5).
• Stay organized, manage multiple priorities, and communicate proactively and in a timely manner with all constituents.

Qualifications:

• Extensive middle school teaching experience.
• Bachelor’s Degree with Master’s (MA) or Doctorate (PhD) preferred.
• Knowledge of and commitment to JRP (Justice, Respect, and Peace) principles.
• Familiarity with restorative practices and student-centered leadership.
• Experience leading student programming, events, or advisory structures.

Professional Qualities:

• Highly organized and detailed oriented with the ability to multitask effectively.
• Excellent written and verbal communication skills.
• Positive, approachable, and engaging with middle school students and adult colleagues.
• Consistent and clear in establishing and enforcing expectations.
• Strategic, professional, and values-driven leadership aligned with Benedictine education.
• Ability to collaborate across departments and contribute to the overall middle-school community.
• Creativity, flexibility, and ability to handle multiple priorities.