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Associate Head of School

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Near North Montessori School
Full Time position
Listed on 2026-01-12
Job specializations:
  • Education / Teaching
    Education Administration
  • Management
    Education Administration
Salary/Wage Range or Industry Benchmark: 160000 - 190000 USD Yearly USD 160000.00 190000.00 YEAR
Job Description & How to Apply Below

Overview

Founded in 1963, Near North Montessori School (NNM) serves more than 560 students from toddlers through 8th grade, supported by a team of 140 dedicated employees. Located near Wicker Park in Chicago, NNM is one of the largest Montessori schools in the nation. Highly regarded for its Montessori pedagogy and innovative approach to education, NNM features an innovation studio, a swimming pool, a playground, a rooftop urban farm, and a student-managed Sandwich Shoppe.

NNM seeks a trained Montessori professional (AMS or AIMS certified) with significant classroom and administrative experience to serve as Associate Head of School.

The Associate Head of School reports to the Head of School and serves as a key member of the senior leadership team, working closely with other administrators and the Board of Directors. The qualified candidate will oversee the Academic Directors, STEAM Coordinator, Spanish Coordinator, School Librarian, Director of Learning Support, and Athletic Director.

Key Responsibilities
  • Oversee the 0-14 academic program and curriculum
  • Support teachers and Academic Directors in their professional practice
  • Plan and facilitate faculty meetings and professional development
  • Serve as a thought partner to the Head of School in implementing strategic goals for the academic program
  • Set the annual academic calendar and finalize the master schedule in collaboration with the Master Scheduler
  • Review and update the scope and sequence of the 0-14 academic program
  • Manage student assessments and analyze instructional focus areas
  • Track and analyze student assessments to inform instructional priorities
  • Foster and support a strong professional culture among faculty and staff
  • Represent the school at regional, state, and national associations
  • Handle disciplinary matters and conduct investigations as needed
  • Partner with the Director of Human Resources to create job announcements, screen, and identify candidates for employment
  • Organize and facilitate a year-long orientation and onboarding program for new faculty and staff members
  • Oversee the evaluation process for lead teachers and assistant teachers
Qualifications
  • Bachelor's degree required; advanced degree preferred
  • Montessori certification (AMS or AIMS) with 5+ years of classroom experience
  • Senior administrative experience at a Montessori school
  • Proven experience supervising personnel and managing multiple projects and programs
  • Demonstrated commitment to equity and inclusion, with training or professional development in these areas
  • High emotional intelligence and openness to diverse perspectives and experiences
  • Collaborative work style with a positive outlook and sense of humor
  • Strong integrity and exemplary work ethic
  • Ability to handle confidential and sensitive matters with discretion and sound judgment
  • Proficiency with Google applications and current educational technology
Additional Information

Pay Information:
The salary range for this position is $160,000 - $190,000 annually based on skills and experience.

Near North Montessori offers a variety of benefits which include:

  • Medical, Dental, and Vision options
  • Short Term & Long Term Disability
  • EAP Program & Pet Insurance
  • Flexible Paid Time off
  • Professional Development Opportunities
To Apply

Submit the following materials to Angela Garcia, Head of School, at agarcia:

  • Resume
  • Cover letter
  • Brief educational philosophy statement
  • Names of three professional references

Near North Montessori believes that each individual is entitled to equal employment opportunity without regard to race, color, religion, gender, national origin, age, disability, genetic information, sexual orientation, ancestry, veteran status, or any other characteristic protected under federal, state, or local anti-discrimination laws. The School’s equal employment opportunity practices extend to recruitment, hiring, selection, compensation, benefits, transfer, conditions, and privileges of employment.

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Position Requirements
10+ Years work experience
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