NOW HIRING: School Administrator / Assistant Head of School

NOW HIRING: School Administrative / Assistant Head of School

Cabrillo Montessori School | Santa Clara, CA

Help Lead a Thriving Montessori Community

Are you a passionate educator and natural leader who enjoys supporting teachers, building meaningful relationships with families, and creating exceptional experiences for children? Are you looking for a role where you can make an impact today while growing into greater leadership opportunities tomorrow?

Cabrillo Montessori School is seeking an Assistant Head of School to join our dedicated team in Santa Clara. This is an exciting opportunity for someone who is organized, collaborative, and eager to grow within a company that is committed to developing future leaders in early childhood education.

Located in the heart of Silicon Valley near NVIDIA, Cabrillo Montessori School is part of the Montessori School of Silicon Valley (MSOSV), a network of high-quality Montessori schools serving children from toddlerhood through kindergarten.

About the Role:

As Assistant Head of School, you will partner closely with the Head of School to support daily operations, strengthen family relationships, and ensure our classrooms and staff have everything they need to thrive.

This role is ideal for someone who enjoys both leadership and hands-on involvement. No task is too small when it comes to supporting children, families, and teachers. Whether you're assisting with enrollment, supporting classroom transitions, helping families feel welcome, or ensuring operations run smoothly behind the scenes, you'll play a key role in the success of our school community.

Most importantly, we're looking for someone who is interested in building a long-term career with our organization. We believe in promoting from within and providing opportunities for talented team members to advance into school leadership positions.

What You'll Do

• Partner with the Head of School to ensure smooth daily school operations.
• Support and mentor teaching staff while fostering a positive team culture.
• Build strong, trusting relationships with families and serve as a resource throughout their Montessori journey.
• Assist with enrollment, family onboarding, scheduling, billing, and administrative processes.
• Help coordinate staffing and classroom coverage as needed.
• Ensure classrooms are fully equipped with the materials and resources necessary for success.
• Support licensing compliance, safety procedures, and school policies.
• Step in wherever needed—from classroom support and family communication to operational tasks that keep the school running efficiently.
• Contribute to a culture of collaboration, professionalism, and continuous improvement.
  

What We're Looking For:

Skills & Qualities

• Strong leadership potential and a collaborative, team-first mindset.
• Exceptional organizational and multitasking skills.
• Excellent communication and relationship-building abilities.
• A proactive, solutions-oriented approach to challenges.
• Warm, professional, and approachable demeanor.
• Passion for early childhood education and child development.
• Desire to grow professionally and take on increasing leadership responsibilities.
  
  

Qualifications

• Experience working in a preschool, childcare, or educational setting ideal.
• Leadership or administrative experience preferred.
• Montessori experience is a plus but not required.
• Strong computer and administrative skills.
• Familiarity with school management software is a plus.
• Minimum of 12 ECE units completed or willingness to obtain them (we help to support obtaining your ECE units through tuition support and reimbursement).
• Ability to meet California licensing requirements.
  

About Cabrillo Montessori & MSOSV

Cabrillo Montessori School is part of the Montessori School of Silicon Valley (MSOSV), a growing organization dedicated to providing authentic Montessori education in nurturing, child-centered environments. Our schools offer fully implemented Montessori programs alongside enriching experiences including Art, Gardening, Cooking, and Science Studio programs. We are deeply committed to creating environments where children feel safe, respected, and inspired to learn.

Just as importantly, we are committed to investing in our employees. We believe great schools are built by great people, and we actively support career advancement, professional development, and leadership growth throughout our organization.

Why Join Us?

• Competitive salary based on experience.
• Medical, dental, and vision benefits.
• 401(k) with 4% employer match.
• Paid professional development opportunities.
• Leadership training and career advancement pathways.
• Supportive and collaborative work environment.
• Opportunity to make a meaningful impact on children, families, and educators every day.
  

If you're ready to join a warm, dynamic Montessori community and build a rewarding career in school leadership, we'd love to hear from you.

Apply Today!