Assistant Director

Guidepost Montessori; Chicago (IL); On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Mentor network

Career growth

Health/dental/vision insurance

Paid time off

75% tuition discount for two children

Meaningful education program

Job summary

Guidepost Montessori in Chicago seeks an experienced leader to join as Assistant Head of School. You will work closely with the Head of School to ensure a high‑quality learning experience for children, outstanding parent service, and a supportive, collaborative team culture across the campus.

The role emphasizes community outreach, tours for prospective families, and driving enrollment through a CRM. You will oversee day‑to‑day operations—billing, supplies, scheduling—and engage with parents to

Qualifications

• DCFS requirements
• Early childhood education leadership experience
• Affinity for connecting with people
• Strong organizational skills
• Exceptional written and verbal communication skills
• Strong attention to detail with a focus on results
• Facility with computer systems
• High degree of personal initiative

Responsibilities

• Support the creation of a strong campus culture aligned with the mission.
• Plan and host community outreach events.
• Give tours to prospective families and convert leads to enrolled families.
• Drive enrollment using a CRM system.
• Manage day-to-day operations: billing, supplies, scheduling maintenance.
• Interface with parents to build community and address concerns.

Skills

Leadership experience

Communication skills

Organizational skills

Attention to detail

Initiative

Computer literacy

CRM familiarity

Education

Montessori certification

Tools

Salesforce

Billing software

Job description

We're now hiring an experienced leader to join our growing team as Assistant Director (Assistant Head of School) in the Chicago, Illinois area!

Guidepost Montessori is a community ofeducators who are driven by a deep desire to bring about widespread change in education today. We believe that the traditional method of education used in most schools is antiquated, outdated, and broken. To meet the needs of today's students and to bring about true progress in the world around us, we need an education model that fosters independence and develops competent, capable, action-oriented thinkers and change agents.To that end, we are committed to dramatically increasing the amount of high-fidelity, authentic Montessori programs, not only in the U.S., but around the globe!

The Assistant Head of School Position:

The Assistant Head of School works closely with the Head of School to ensure that the school provides a high-quality learning experience for children, exceptional customer service to parents, and a supportive, collaborative work environment for staff.The ideal Assistant Head of School willlove building community, working with parents, and leadingcommunity outreach initiatives.Key responsibilities include, but are not limited to:

• Supporting the creation of a strong culture on campus that embodies the mission of our organization
• Planning and hosting community outreach events
• Giving tours to prospective families, and converting leads to enrolled families
• Driving the enrollment process (managing leads utilizing a CRM system)
• Managing general, day-to-day operations for the school: billing, supply ordering, scheduling maintenance
• Interfacing with parents to build community, answer questions, and resolve any concerns that may arise

What we offer:

• A network of supportive peers and mentors who regularly share best practices
• Career growth and promotion opportunities
• Health, dental, and vision insurance
• Paid time off and paid holidays
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• 75% tuition discount for two children at any school within our network (we serve children 3 months through 6 years old)
• The opportunity to contribute to a high-quality educational program that serves the individual needs of each child

We'd love to talk to you if you possess:

• DCFS Requirements
• Early childhood education leadership experience
• An affinity for connecting with people
• Strong organizational skills
• Exceptional written and verbal communication skills
• Strong attention to detail with a focus on results
• Facility with computer systems
• A high degree of personal initiative

We'd prefer you over other candidates if you have:

• Experience as an Admissions, Administrative, Program or School Director for a preschool
• Familiarity with the Montessori method of education or a Montessori certification
• Experience working with Salesforce/CRM and billing software
• Knowledge of the local community that will inform marketing effort

Guidepost Global Education and Guidepost Montessori are committed to a policy of Equal Employment Opportunity (EEO). We will not discriminate on the basis of age, sex, race, color, creed, religion, ethnicity, sexual orientation, gender identity, gender expression, national origin, alienage or citizenship, disability, marital status, military or veteran status, or any other legally recognized protected basis under applicable federal, state or local laws, regulations or ordinances. Our leadership is dedicated to ensuring the fulfillment of this policy. When requested, we are committed to reasonably accommodate employees and applicants with disabilities or special needs that may require an accommodation.