Headmaster

Description

Headmaster
Kairos Montessori School,

Cascais, Portugal

About Kairos Montessori
Founded in 2017 in Cascais, Portugal, Kairos Montessori was born from the conviction that this is a providential moment to form lifelong learners-young people who delight in learning and are equipped to adapt and thrive in an ever-changing and complex world. Serving children ages 3-18 in a diverse community of Portuguese, British, and international families, Kairos invites students to become active, joyful learners who think critically, develop strong organizational and academic skills, and are supported in reaching their full God-given potential.

Within a rich Montessori environment, students spend generous time outdoors, learning to cherish and steward the gift of their bodies and the natural world. Their spiritual lives are nurtured through the Catechesis of the Good Shepherd and a vibrant Catholic culture that encourages a personal relationship with God. In community, children learn self-discipline and social responsibility, growing in courtesy, respect, and cooperation so that they may serve others with maturity and Christian charity.

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. 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 frees the founders to serve in more strategic, board-level, and evangelizing roles.

Key Outcomes & Measures

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.

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.

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.

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.

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 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.

To Apply: Send resume and cover letter outlining your alignment with Kairos Montessori to Edi Denton, edenton@arcadiaed.com.