NOW HIRING!!! Assistant Head of School (Future School Leader Program)

Assistant Head of School (Leadership Development Opportunity)

Cabrillo Montessori School | Santa Clara, CA

Ready to Turn Your Grit, Drive, and Passion into a Career?

Cabrillo Montessori School is looking for an Assistant Head of School who brings more hunger, heart, and hustle than fancy degrees or a long resume. If you’re the kind of person who feels stuck in an entry-level or junior role, knows you’re capable of so much more, and is ready to roll up your sleeves, grow into a true leader and advance your career— this is your opportunity.

We value hungry, humble, and emotionally intelligent people who love working with children, thrive in dynamic environments, and are excited to build something meaningful. No perfect background required — just a strong work ethic, genuine enthusiasm, and the ability to solve problems.

What You’ll Do

• Support the daily heartbeat of the school — keeping operations smooth and classrooms thriving


• Build strong, positive relationships with children, families, and the classroom staff


• Help with enrollment, operations, and family communications


• Coordinate schedules, provide classroom coverage, and jump in wherever needed


• Grow your skills in school administration, licensing, compliance, and leadership


• Receive direct mentorship from experienced leaders who are invested in your success

This is a hands-on role designed for real growth — not just another job.

Who We’re Looking For

• Someone with a positive attitude and unstoppable work ethic


• Excellent communicator who stays organized even when things get busy


• Experience working with children is a big plus (but not mandatory)


• ECE units preferred – we will support your effort to earn credits if you don’t already have them


• A genuine interest in leadership, professional development, and long-term career growth


• Montessori background is helpful but not required — we’ll train you


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If you’re ambitious, reliable, quick to learn, and ready to prove yourself, we want to meet you. Over 80% of our current staff leadership started in entry-level positions and advanced through dedication, mentorship, and on-the-job growth.  This is your opportunity to do the same.

Why Join Cabrillo Montessori School?

• Real leadership development and personalized mentorship


• Clear pathways for advancement — we promote from within


• Competitive benefits: Medical, dental, and vision coverage


• 401(k) with 4% employer match


• Tuition assistance and ECE reimbursement


• A supportive, collaborative team that feels like family

If you’re tired of feeling underutilized and you’re ready for a career where your grit and enthusiasm are truly valued, we’d love to talk.

Apply today and take the next step in your career. Send your resume and a short note telling us why you’re excited about growing with Cabrillo Montessori School.

We can’t wait to meet our next rising leader.