Headmaster

Job Description – Headmaster Kairos Montessori Location: Quinta da Marinha, Cascais, Portugal Reports to: Kairos Board About Kairos Montessori Founded in 2017, Kairos has quickly earned a reputation as one of the most serious and distinctive Catholic Montessori institutions in Europe, attracting families and educators intentionally seeking depth, coherence, and excellence. Kairos Montessori is a PK-12 Catholic Montessori school located on the Atlantic coast near Quinta da Marinha, Cascais, minutes from the medieval city and UNESCO Heritage site of Sintra. It is, without exaggeration, one of the most staggeringly beautiful settings of any school across the world. Set within a marine pine forest, the campus includes renovated stone buildings and a working farm where animals are cared for by students and faculty as part of daily life. The school is a total immersion into a kind of monastic life: an education of ora et labora that naturally lends itself to the contemplation of Christ made manifest in and through all of creation. The agricultural cycle, the Catholic liturgical calendar, and the integration of Catechesis of the Good Shepherd with rigorous Montessori pedagogy shape the annual rhythms of the school. Academically and spiritually, Kairos is committed to the formation of the whole person through a demanding encounter with reality and a robust philosophical equipment to see all of life a coherent overflow of the Logos. STEM, the arts, faith, and the humanities are integrated within a culture shaped by beauty, responsibility, and intellectual seriousness. Prayer, weekly Mass, sacramental life, and opportunities for Eucharistic adoration are central to daily school life. As the school expands toward a fully articulated liberal-arts secondary program, Kairos aims to serve as a model for schools seeking to reclaim rigorous education grounded in truth: an unapologetic alternative to technocratic and utilitarian approaches to schooling. What the Kairos leadership team has built in such a short time is extraordinary. Their vision is bold and attainable: to become a premier model of Catholic, liberal arts Montessori education and a global training hub for school leaders. Arcadia is convinced this vision is not aspirational; it is inevitable, giventhe right leadership. Why the Role Exists The Headmaster exists to guard and deepen Kairos's Catholic Montessori identity while leading the whole school, especially the adolescent and upper school (12–18), into mature academic, spiritual, and communal excellence. Part of this vision includes partnering with the Kairos leadership team to imagine and implement a Catholic Liberal Arts education in the high school that seamlessly integrates and serves as a capstone to the elementary and adolescent Montessori curriculum. This leader becomes the unifying educational head across the 3–18 journey, clarifies and strengthens the adolescent program toward strong A-level outcomes and Christian maturity, and takes on the operational responsibilities necessary to free the founders to serve in more strategic, board-level, and evangelizing roles. While a Kairos is a Montessori school, a Montessori background is not required- proper training and certification will be provided as necessary. Key Outcomes & Measures 1. Stable, Clear School Leadership A simple, trusted leadership structure is in place; deputies and the Academic Director look first to the Headmaster. The school runs smoothly without the founders' daily involvement; staff and parents know who decides what. 2. Coherent Adolescent & Upper School (12–18) A clear written framework integrates Montessori adolescent principles, British qualifications, and an emerging classical liberal-arts identity. Roles and responsibilities for the upper school are shared sustainably beyond the founders. Families express growing confidence in the path to IGCSEs/A-levels and in the overall formation of their teenagers. 3. Deepened Catholic & Montessori Identity The Headmaster is recognized as a praying, faithful Catholic leader who articulates a Catholic, Montessori vision of the child. Staff formation, discipline, inclusion decisions, and parent communication consistently reflect that vision. First steps are taken to form parents as partners in both faith and Montessori education. 4. A More Unified, Joyful Community The Headmaster is a visible, approachable presence with students, staff, and parents across cultural subgroups. Hard conversations are handled promptly with clarity and charity. Parent feedback and everyday experience reflect increasing trust, unity, and shared mission. 5. Strengthened Talent & Future Capacity A realistic staffing plan is in place, especially for the adolescent years. At least one key hire or retention strengthens the upper school and embodies the Kairos vision. Early connections are made with formation and recruitment partners aligned to Kairos's Catholic + Montessori + English-speaking profile. Character Traits & Competencies Practicing Catholic in good standing, rooted in the sacramental life of the Church and comfortable praying with the community. Deep respect for the Montessori vision of the child, instinctively acting as a guide rather than a controller. Missionary-hearted and courageous, able to lead in a secular European context with cultural, legal, and linguistic complexity. Significant school leadership experience (Head, Principal, Deputy, or similar), ideally in Catholic, Montessori, classical, or closely related settings. Proven ability to build, lead, and evaluate staff teams, giving clear feedback with charity and truth. Warm, steady, and articulate communicator with parents, staff, and students, especially in moments of tension or change. Familiarity with Montessori education (AMI or similar preferred) and eagerness to deepen in Montessori adolescent pedagogy. Genuine appreciation for the classical liberal-arts tradition and desire to integrate rich humanities and thoughtful discussion into the 12–18 program. Experience with rigorous academics and, ideally, knowledge of British qualifications (IGCSEs / A-levels or comparable systems). Cross-culturally savvy; able to build trust in a multilingual, international community. Organized and reliable, with enough operational sense to support timetabling, enrollment stability, and basic financial and compliance realities in partnership with board and operations staff. Humble collaborator with the founders, deputies, and Academic Director—teachable, honest, and willing to share leadership. Competitive compensation offered. Flexible depending on experience and quality of fit. To Apply Please submit a cover letter and resume outlining your alignment with the mission of Kairos Montessori and your vision for a classical, Catholic Montessori school to: Edi Denton, .