School Leadership
Guidepost Montessori · Chicago, Illinois
Posted about a month ago · $50,000 - $60,000
or apply directly on Guidepost Montessori's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 30 days Guidepost Montessori's roles stay open a median of 36 days
- Reposted
- No
- Salary listed
- Yes 34% of Guidepost Montessori's roles list one
- Ghost-job risk at Guidepost Montessori
- low 0 stale, 2 reposted of 234 open
- Hiring momentum
- 466 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from Guidepost Montessori's own greenhouse board since 2026-08-03. Full hiring picture for Guidepost Montessori.
About this role
The School Leadership position involves connecting with experienced leaders to fill future roles within the Guidepost Montessori network in Chicago. Responsibilities include leading campus teams, managing enrollment processes, fostering family relationships, and overseeing daily school operations to ensure a high-quality educational experience.
- benefits
- 4/5
- freshness
- 4/5
- career value
- 3/5
- role clarity
- 4/5
- pay transparency
- 5/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Guidepost Montessori as an employer.
What you need
- Experience in early childhood education, school operations, admissions, or leadership roles
- Meet Illinois DCFS director requirements
- Highly organized and able to manage multiple priorities effectively
- Enjoy working with families and building strong relationships
- Clear and professional communication skills, both verbally and in writing
- Strong attention to detail and follow-through
Nice to have
- Experience in roles such as school leadership, admissions, program management, or operations
- Familiarity with the Montessori method of education or Montessori certification
- Experience using CRM systems and billing platforms
- Knowledge of the local community to support outreach and enrollment efforts
What you get
- Ongoing professional development
- A network of supportive peers and mentors who regularly share best practices
- Career growth and promotion opportunities
- A competitive salary of $50,000 - $60,000
- Health, dental, and vision insurance
- Paid time off and paid holidays
Worth weighing
- No specific details on the exact nature of future leadership opportunities
- Salary range may be considered low for some candidates in leadership roles
Summarised from Guidepost Montessori's posting. Read the full original.
Listed by Guidepost Montessori on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
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