Montessori Assistant Head of School: Enrollment & Community

Posted 18 days ago

guidepost montessoriBrooklyn (NY)

SENIORITY

Mid

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About the role

Guidepost Montessori is hiring an experienced leader for the Assistant Head of School role in the Chicago, Illinois area. The position partners with the Head of School to provide a high-quality learning experience for children, excellent service to families, and a supportive work environment for staff. The ideal candidate will enjoy building community, engaging with parents, and leading outreach initiatives. Leadership in early childhood education and Montessori familiarity are highly valued.

Before you apply

Applying takes about a minute. These four things decide how fast it moves after that.

Your profile is current

It's what we read first. Occupations, seniority and locations matter more than a long history.

Two examples you can talk through

Not a portfolio — just two pieces of work where you can explain the decisions and what you'd change.

A number in mind

What you're on now and what would make you move. We negotiate better when we know both.

Your notice period

Employers plan around it, and it's the question that stalls offers most often.

Once you apply, someone reads it and calls you before anything reaches the employer — usually within two working days.

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