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Holy Family Classical School Job Description - Headmaster Reports to: Pastor About Holy Family Holy Family Classical Catholic School is a rapidly growing Pre-K-12 school located in downtown Tulsa, Oklahoma, serving families drawn to a serious, joyful recovery of the Catholic intellectual tradition. Founded anew within the past decade, the school has quickly become a focal point for Catholic cultural renewal in the country, attracting families who desire a deeply Catholic education ordered toward truth, beauty, and goodness, and who see education as inseparable from the formation of the whole person. Weekly Mass, frequent confession and adoration, daily observation of the Daily Office, and a robust liberal arts curriculum shape a community marked by intellectual seriousness and spiritual hunger. The school is situated within a remarkable and expanding set of buildings adjacent to an historic cathedral, stewarding land and property with an eye toward permanence, beauty, and long-term mission. As part of a broader Catholic renewal and land movement, Holy Family draws families seeking home in the truest sense, stability, and an education capable of passing on the torch of Christian civilization to their children. Tulsa offers an exceptionally affordable cost of living, strong family life, and a growing Catholic ecosystem, making Holy Family one of the most premier positions ever offered by Arcadia. Why the Role Exists The Headmaster exists to provide unified, seasoned leadership to a school experiencing rapid growth and increasing cultural influence, ensuring long-term stability while drawing the community into deeper communion through Christ by renewed engagement with the riches of the Catholic intellectual tradition. After a period of leadership turnover, Holy Family seeks a steady, trusted leader who can articulate and embody a coherent educational vision across Montessori, liberal arts, and Great Books programs; form and mentor a young, highly capable faculty; strengthen trust with families through clarity and follow-through; and steward the schools people, programs, and physical campus with prudence, confidence, and pastoral care. Key Outcomes & Measures Stable, Trusted School Leadership The Headmaster is recognized as the clear missional and tactical leader of the school. Day-to-day operations run smoothly without ambiguity or reactive decision-making. Conflict among faculty, parents, or programs is handled promptly, decisively, and charitably. Coherent Classical Catholic Identity (Pre-K-12) A clear, shared framework articulates how Montessori formation, the liberal arts, and Great Books education form a unified classical Catholic vision. Faculty and parents can confidently explain the schools educational approach and distinctives. Early steps toward stabilizing and strengthening the high school program inspire growing parent confidence. Faculty Formation & Professional Maturity The Headmaster is experienced as a mentor and guide, not merely an administrator who is leans on an already robust internal faculty leadership team. Faculty receive intellectual, pedagogical, and spiritual formation appropriate to a classical Catholic school. Young teachers grow in clarity and confidence; enthusiasm is refined into shared standards and practice. Unified, Confident Parent Community Parents experience the Headmaster as a credible guardian of the schools mission. Communication is proactive, clear, and consistent, even in moments of tension. Trust increases as families see decisions aligned with the schools stated vision and values. Stewardship of Growth & Future Capacity Enrollment growth, campus expansion, and program development are stewarded wisely. Staffing decisions strengthen long-term mission alignment and sustainability. The Headmaster collaborates effectively with the Pastor, Superintendent, and diocesan leadership. Character Traits & Competencies The ideal candidate will demonstrate: A practicing Catholic faith, rooted in the sacramental life of the Church and comfortable leading prayer and worship in community. Deep conviction about, and fluency in, classical Catholic education, broadly understood across Montessori, liberal arts, and Great Books traditions. At least 5 years school leadership experience strongly preferred (Headmaster, Principal, Assistant Head, or similar), with proven ability to lead adults and manage complexity, and implement administrative programs with efficacy. The capacity to form and mentor faculty, including classroom coaching, feedback, and intellectual leadership. A confident, warm, and articulate communication style with parents-especially highly engaged families who care deeply about mission and curriculum. Strong operational judgment: able to clarify systems, roles, and procedures so that mission is supported by order. Emotional maturity, steadiness, and resilience in the face of growth, pressure, and high expectations. Desire for long-term leadership and rootedness in Tulsa, rather than a short-term or transitional role. Masters in a relevant field per Diocesan requirements. Competitive salary offered, flexible depending on education, years of experience and quality of fit. Health insurance, family tuition assistance, retirement options available. To Apply please submit a cover letter and resume outlining your alignment with the mission of Holy Family Classical School to Edi Denton, ********************* .