Montessori Early Childhood Head Teacher

The Ancona School
Chicago, IL
To Apply: Email resume and cover letter to [email protected]
About the Ancona School

The Ancona School (Ancona) is an independent school located in Chicago's historic Hyde Park Kenwood community, educating students 3 years old through 8th grade. Since our founding in 1962, Ancona has been dedicated to diversity in both our community and our curriculum, which draws upon the Montessori and Progressive Education models. Social justice education is the cornerstone of Ancona’s mission as a school; it informs what we teach and how we teach it. At every grade level, Ancona students learn to identify inequality and are empowered to address injustice in the world.
At Ancona, we seek diversity in our faculty and staff to broaden students’ academic experiences and to enrich our school community. Ancona is looking for individuals who will contribute to our social justice mission and embrace the rich diversity of our school and city as we prepare our students for an increasingly complex world. Candidates must be sensitive to the needs of, and possess an interest in, working in a school community that is diverse with regard to gender, race, ethnicity, religion, nationality, sexual orientation, gender identity and expression, and disability status.

Summary/Objective
The Ancona School seeks a full-time Head Teacher for its accredited Montessori Early Childhood program. Head teachers at Ancona provide support for the overall development and learning of our students, including the care of the children and maintenance of the Montessori environment. Specific Duties Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
Essential Functions
  • Develop lesson and unit plans; manage the learning experience for students to ensure the needs of the group and individual students are met
  • Assist students toward self-directed learning and normalization.
  • Maintain a neat, well-organized, and attractively-prepared environment consistent with Montessori pedagogy
  • Supervise and mentor the classroom’s Assistant Teacher, providing guidance on Montessori philosophy and classroom management
  • Participate in professional activities designated by the Head of School and Instructional Leadership Team, which may include workshops, curriculum retreats, meetings, grade reporting, planning, and other professional pursuits
  • Attend all planned meetings, including staff, level, committee, and evening parent education events
  • Develop effective relationships with parents by: providing opportunities to discuss and understand their child’s individual progress; encouraging them to bond with both the class and the larger school community; and providing individualized tracking of student progress
  • Participate in the admissions process, speaking from time to time with prospective families at the request of the Admissions Director, members of the Instructional Leadership Team, and/or Head of School
  • Prepare the classroom each day in collaboration with the Assistant Teacher: outline routines and any special activities, ready materials / identify groups of children who might be shown certain materials that day, and manage administrative duties (attendance, lunch orders, and student records)
Daily Expectations During Class and After Dismissal
  • Provide a nurturing and stimulating environment to facilitate children’s growth, exploration, and participation
  • Assist children who need individual help to choose work, protect working children from interference (including adults), and unobtrusively monitor the work of individual children
  • Prepare small group and individual presentations involving a new material or progressive step; withdraw at regular intervals to observe
  • Uphold and reinforce positive behavior by modeling or drawing attention to ground rules
  • Observe the class’s overall feeling and tone, and sense changing mood or activity; monitor group activities to maximize healthy socialization, fostering of community, and healthy recreation
  • Treat children with unconditional positive regard and provide individualized care for their needs
  • Work to maintain health and safety standards with snack, lunch, hand washing, and toileting
  • Refresh the environment after school, assembling materials for the following day
  • Complete daily notes and reflect on individual children and group interactions in collaboration with Assistant Teacher: compare observations, discuss relevant points in Montessori theory, review learning materials, and group activities
Additional Expectations
  • Collaborate with fellow Early Childhood teachers, Instructional Leadership, and Head of School to share ideas, plan, and problem-solve
  • Prepare for and participate in: parent-teacher conferences, evening parent education events, and community gatherings (e.g., Montessori Night, open houses, etc.
Reporting Relationships Reports to Head of School and a member of the Instructional Leadership Team; provides lead direction to assigned assistants.
Required Qualifications

Education and Experience
  • Montessori trained and certified required; Bachelor’s degree in a related field
    Previous experience teaching in a Montessori setting
  • Spanish Fluency (preferred)
Additional Requirements
  • CPR/First Aid certification (preferred)
  • Ability to pass a background check
  • Have the physical capacity to work with preschool-aged students
  • Keep up with professional development (15 hours per school year)
Expected Hours of Work Monday-Friday, 7:50 am - 3:30 pm Wednesdays, 7:50 am - 4:45 pm (Reserved for Staff Meetings) Occasional evenings and/or weekends may be required for school events
Other Duties
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice.
EEO Statement
It is the policy of Ancona School not to discriminate against any employee or any applicant for employment because of age, race, religion, color, handicap, sex, physical condition, developmental disability, sexual orientation, or national origin. This policy shall include, but not be limited to, the following: recruitment and employment, promotion, demotion, transfer, compensation, selection for training, including apprenticeship, layoff, and termination.

Posted 2026-03-19

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