Assistant Head of School

Location: Santa Rosa Beach, Florida

School Type: Montessori Preschool and Kindergarten

Job Summary:

We are seeking a warm, self-aware, dedicated, and highly organized Assistant Head of School to support the daily operations and long-term vision of our Montessori preschool and kindergarten. This role requires a compassionate leader with strong interpersonal skills, administrative strengths, and a deep respect for Montessori principles. The ideal candidate thrives in a collaborative environment, enjoys detailed work, and excels at promoting and maintaining harmony within teams.

Key Responsibilities:

• Support the Head of School in managing daily operations, staff coordination, and communication with parents.
• Uphold and model the core values of the Montessori philosophy, especially the respectful treatment of children, staff, and parents.
• Assist in hiring and training faculty and staff.
• Assist, when necessary, in resolving conflicts among staff, parents, or students with a calm and diplomatic approach.
• Organize school records, compliance documentation, scheduling, and other administrative tasks.
• Participate in planning and executing school events, professional development sessions, and parent education workshops.
• Help in classrooms as needed when staff members need extra support or there is an unexpected absence.
• Foster a supportive, respectful, and collaborative school culture.

Required Qualifications:

• Bachelor’s degree in Education, Early Childhood, Administration, or related field or 4 years equivalent experience, with an emphasis on leadership.
• Strong alignment with Montessori values, especially respect for the dignity and independence of the child.
• Proven administrative and organizational abilities, with a detail-oriented mindset and an emphasis on best practices and confidentiality.
• Excellent interpersonal and written/verbal communication skills.
• Demonstrated success in conflict resolution and team collaboration.
• Ability to multitask and complete tasks in a timely and efficient manner.

Preferred Qualifications:

• Strongly preferred: Episcopal faith background and church membership
• DISC personality profile of S/C (Steady/Conscientious), or a temperament that values and fosters reliability, consistency, and structure.
• Montessori training or certification (AMI, AMS, or MACTE-accredited).
• Experience working in a Montessori school environment.
• Prior experience in school leadership or administration.
• Familiarity with state childcare regulations and licensing requirements.
• Technological proficiency with school management software or digital tools.

Compensation & Schedule:

• Full-time position, Mon-Thursday 9-5; Friday 7:30-3:30
• Salary and benefits (DOE); benefits include a 403(b) retirement program with employer match, health insurance, vision, dental and life insurance, free teladoc health services, and more.
• Professional development opportunities, including attending AMS events
• Supportive, mission-driven work environment

Pay: From $60,000.00 per year

Benefits:

• 401(k) matching
• Dental insurance
• Employee discount
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Tuition reimbursement
• Vision insurance

Application Question(s):

• Are you willing to take an 8 week training in Montessori principles and practices at the beginning of your tenure with us?

Experience:

• Early childhood education: 4 years (Required)

Ability to Commute:

• Santa Rosa Beach, FL 32459 (Required)

Work Location: In person