School Leadership

Guidepost Montessori
Chicago
Workplace: OnsiteFull timeUSD 50,000 - 60,000 annuallyFunction: Administration & Executive AssistanceSkills: ["Organization","Communication","Customer focus","Attention to detail","Follow-through"]

Connect with experienced school leaders across Downtown Chicago who want future leadership opportunities within a Montessori education network. You may lead campus teams, support enrollment health, foster family relationships, and ensure operational and program excellence—covering culture building, tours and admissions, CRM lead tracking, and day-to-day operations like billing, supplies, and facilities coordination. Enjoy ongoing development within a network of mentors and peers.

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Guidepost Montessori
Guidepost Montessori
4 days ago

School Leadership

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Last checked: 11 hours agoStatus: Live
Reposted: similar role first listed 6 months ago

Job Summary

Connect with experienced school leaders across Downtown Chicago who want future leadership opportunities within a Montessori education network. You may lead campus teams, support enrollment health, foster family relationships, and ensure operational and program excellence—covering culture building, tours and admissions, CRM lead tracking, and day-to-day operations like billing, supplies, and facilities coordination. Enjoy ongoing development within a network of mentors and peers.
Location: Chicago
Workplace: Onsite
Employment Type: Full time
Job Function: Administration & Executive Assistance
Seniority: Manager level

Key Responsibilities

  • •Support a strong, mission-aligned campus culture reflecting Guidepost values.
  • •Build relationships with families and create a welcoming, high-quality school experience.
  • •Lead tours for prospective families and guide them through the enrollment journey.
  • •Manage enrollment processes, including lead tracking and follow-up through CRM systems.
  • •Oversee day-to-day school operations, including billing, supply ordering, and facilities coordination.

Pay and Benefits

Salary: USD 50,000 - 60,000 annually
Perks:Health InsuranceDentalVisionPaid LeavePaid HolidaysTuition Discount

Key Requirements

  • •Meet Illinois DCFS director requirements.
  • •Have experience in early childhood education, school operations, admissions, or leadership roles.
  • •Be highly organized and able to manage multiple priorities effectively.
  • •Communicate clearly and professionally, both verbally and in writing, and respond to family questions with professionalism and care.
  • •Be comfortable using systems and learning new tools (including CRM systems and billing platforms).
Experience:Early childhood educationMontessoriEducationCRM
Skills:OrganizationCommunicationCustomer focusAttention to detailFollow-through
Languages:English
Tech Stack:CRM systemsBilling platforms

Company Brief

Guidepost Montessori
Guidepost Montessori operates a network of Montessori schools offering early childhood and elementary education grounded in Montessori pedagogy, focusing on individualized learning, hands-on materials, and development of independence, curiosity, and academic readiness.
Industry: Education
Growth: Established Company
Headquarters: United States
Website