Head of School

Head of School / School Director

Location: Chicago, IL Area

Job Type: Full-Time

Work Setting: In Person

About the Opportunity

A growing private Montessori early childhood education organization is seeking an experienced and passionate Head of School / School Director to lead one of its Chicago-area campuses.

This is an opportunity for an education leader who is passionate about Montessori pedagogy and creating an environment where children can develop independence, confidence, and a lifelong love of learning. The Head of School will oversee the campus team, drive enrollment growth, develop staff, foster strong relationships with families, and ensure a consistently high-quality educational experience.

Key Responsibilities

• Develop and execute a strategic plan for the campus, with a focus on growth and operational excellence.
• Build and maintain a strong campus culture aligned with the organization's educational mission.
• Foster a welcoming and collaborative community among staff, parents, and students.
• Ensure the highest standards of educational programming and classroom experience.
• Oversee campus operations and budget while meeting profitability and financial objectives.
• Partner with the Assistant Head of School to achieve enrollment goals.
• Recruit, hire, develop, support, and manage teaching and administrative staff.
• Provide leadership, coaching, and mentorship to the campus team.
• Maintain strong communication with families and create a positive parent community.
• Ensure compliance with applicable state licensing and educational requirements.

Qualifications

The ideal candidate will have:

• Relevant state qualifications for early childhood education leadership.
• Experience leading within an early childhood education environment.
• Strong organizational skills and attention to detail.
• A results-oriented approach with the ability to manage multiple priorities.
• Excellent written and verbal communication skills.
• A demonstrated ability to build a warm, supportive, and collaborative team culture.
• Strong leadership and decision-making skills, including the ability to make sound decisions in ambiguous situations.
• A genuine passion for early childhood education and the Montessori approach.
• A Bachelor's degree is preferred.

Preferred Experience

Candidates with the following experience are especially encouraged to apply:

• Prior classroom teaching experience in an early childhood setting.
• Experience as a School Director, Program Director, Administrative Director, or Admissions Director within a preschool or early childhood education organization.
• Familiarity with Montessori education and/or Montessori certification.

Compensation & Benefits

• Health, dental, and vision insurance
• 401(k) and retirement benefits
• Health savings account
• Life insurance
• Paid time off and paid holidays
• Ongoing professional development
• Career growth and advancement opportunities
• Tuition discount for up to two children enrolled in the school's programs
• Supportive network of education leaders and mentors
• Opportunity to lead a high-quality program focused on the individual needs of each child

Additional Information

This is a leadership opportunity within a private, for-profit educational organization, so the role does not involve fundraising or managing a Board of Directors.

The organization is committed to providing equal employment opportunities and maintaining an inclusive workplace.