Headmaster- St. Elizabeth Ann Seton, A Cabrini Catholic Classical High School

Position Summary

The headmaster serves as the chief administrator and spiritual leader of the Cabrini Classical High School, ensuring the mission of Catholic education is fully alive in every aspect of school life. This role is not only about academic leadership but also about shaping young men and women into faith-filled, responsible adults who are grounded in their Catholic identity, prepared to contribute meaningfully to the Church, their families, and society. The headmaster is entrusted with guiding students to grow in wisdom, virtue, and service while fostering a culture of excellence, faith, and integrity.

Essential Duties

Mission & Catholic Identity

· Uphold and articulate the school’s Catholic mission, ensuring that faith permeates academics, athletics, the arts, and daily life.

· Lead by example as a visible witness to the Catholic faith, nurturing a Christ-centered environment.

· Partner with clergy, faculty, and parents to strengthen the spiritual formation of students, preparing them to live their faith confidently in today’s world.

· Encourage a culture where students embrace responsibility, service, and leadership rooted in Gospel values.

· Lead a robust effort to evangelize parents

Academic & Formational Leadership

· Oversee the development of a rigorous classical Catholic liberal arts curriculum that challenges students intellectually while integrating Catholic social teaching and moral formation.

· Support and mentor faculty to inspire both academic excellence and personal character in students.

· Promote opportunities for students to develop in a strong Catholic environment as independent thinkers, compassionate leaders, and serious learners.

Faculty & Staff Leadership

· Recruit, develop, and support a team of strong Catholic educators committed to the Catholic mission and excellence in teaching.

· Foster a collaborative professional culture based on respect, accountability, and mission-driven service.

· Provide resources and growth opportunities for faculty in both academic and spiritual formation.

Student Life & Personal Growth

· Create an environment of communion that nurtures the whole person—mind, body, and spirit.

· Encourage programs and activities that help students grow into confident, responsible young adults with strong Catholic values.

· Ensure high standards of discipline and respect, guiding students toward personal responsibility, resilience, and moral decision-making.

· Ensure discipline policies are communicated and enforced.

· Promote student opportunities such as vocational, leadership, spiritual and educational.

· Oversee any extracurricular activities.

Internal Financial Stewardship

· Oversee day-to-day financial operations to ensure fiscal responsibility and alignment with school priorities

· Develop and manage the annual budget in collaboration with administrative staff

· Make determinations regarding tuition assistance in accordance with school policies and family needs

· Implement financial policies and procedures that support operational efficiency and transparency

· Coordinate with internal teams on financial matters without direct involvement in Board or Finance Council governance decisions

Teaching and Instructional Leadership

· Model excellence in teaching through occasional classroom instruction and active engagement with faculty

· Support and evaluate faculty to ensure high-quality, mission-aligned instruction across all grade levels

· Promote professional development opportunities that enhance pedagogical skills and subject mastery

· Foster a culture of academic curiosity, intellectual rigor, and student-centered learning

· Ensure curriculum coherence and alignment with school values, standards, and long-term goals

· Encourage interdisciplinary collaboration and innovative teaching practices

Operations & Stewardship

· Work with the Board/Finance Council to oversee financial sustainability, enrollment, and advancement efforts.

· Support admissions and marketing efforts that communicate the distinctive Catholic identity of the school.

· Oversee supervision and evaluation of all staff, while hiring new staff as needed. This includes conducting regular classroom observations and evaluations.

· Communicate with colleges, universities and other post high school programs.

· Ensure compliance with diocesan policies, State and Federal laws, and accreditation standards.

Community & Parent Partnership

· Serve as the primary representative of the school, strengthening trust and collaboration with parents, alumni, parish, and community partners.

· Communicate openly and regularly with families, affirming the shared mission of forming faith-filled, responsible young men and women.

· Build relationships that inspire confidence in the school’s Catholic mission, academic strength, and commitment to developing young, faith-filled Catholics, the next generation of our Church, and civic leaders.

· Provide opportunities for spiritual growth for parents.

Qualifications

· Practicing Catholic in full communion with the Church, with a deep personal commitment to Catholic faith and values.

· Graduate degree, preferably in educational leadership

· Proven leadership in Catholic or independent school settings.

· Strong pastoral presence, with excellent communication and interpersonal skills.

· Demonstrated ability to inspire students, parents, and faculty in pursuit of excellence rooted in Catholic identity.

· Visionary leader capable of balancing mission, academics, operations, and community relationships.

Physical Requirements

· Ability to communicate with staff, parents, and students.

· Ability to stand or sit for 3-4 hours per day with reasonable breaks.

· Ability to keystroke for 3-4 hours per day with reasonable breaks.

· Ability to visit classrooms regularly.

· Ability to bend, stoop, and kneel occasionally.

To Apply:

Please submit a cover letter, curriculum vitae, and pastor recommendation letter to hr@portlanddiocese.org

Job Type: Full-time

Pay: $65,872.73 - $68,448.88 per year

Benefits:

• Relocation assistance

Work Location: In person

Salary : $65,873 - $68,449