Job Title: Assistant Principal

Reports To: Principal/Head of School

Salary Range: $63,835 – $85,189


Founded in 2016, Cypress Junction is a free public charter school located in downtown Winter Haven that follows the Montessori Method. The school has 24 staff members with students ages three through eighth grade. Students are admitted utilizing a random lottery process, including preschool. Scholarships are offered on an income-needs basis to ensure the preschool is accessible. Grades kindergarten through eighth grade are free as part of the public charter. 

Cypress Junction Montessori Mission

Cypress Junction Montessori encourages the development of the whole child by providing a comprehensive Montessori education.

We do this through:

  • Cultivating independent thought, foundational skills, awareness of their environment, empathy for others, social ease, and high self-esteem in every student.
  • Establishing within each child the intellectual, emotional, and physical rigor needed to become a self directed learner, flexible thinker, and creative problem solver.
  • Supporting each student’s ever-increasing curiosity about the world in which they live.
  • Instilling the values and skills necessary to help our students to grow up to be successful global citizens.
  • Bringing academic standards and student passions together to fuel a desire to learn.

Cypress Junction Montessori sets children on a path that embraces creativity, builds self awareness and helps them develop the academic skills, physical tools and personal confidence necessary for lifelong success.

Read more of our Mission and Guiding Principles here: 


CJM’s Assistant Principal will have a profound impact on the development, management, and ultimate success of the school. Reporting to the school’s Principal/Head of School, this is a full-time leadership position starting in August 2022 for the 2022-23 school year.

The Assistant Principal will assist CJM’s Principal in providing the vision and leadership necessary to develop and administer educational programs that optimize the human and material resources available. These programs will ensure implementation of authentic Montessori learning experiences for all students leading to enhanced student achievement within the context of providing a safe and successful school for students, staff, parents, and community in support of enhanced student learning.


  • Coordinating all testing required by state and other regulations.
  • Coordinating ongoing progress monitoring across all classrooms and guiding staff to utilize the data to inform instruction.
  • Serving as the on-site preschool director including coordinating all compliance requirements with DCF.
  • Coordinating all attendance requirements, contracts, paperwork and other preschool administrative duties with teachers, parents/guardians, and agencies.
  • Build strong relationships with the parents and guardians and coordinate all volunteer activities.
  • Recruit and mentor strong substitute teachers and coordinate all required coverage.
  • Manage the LEA, ESE, and ELL programs including mentoring LEA and ESE staff, overseeing 504, IEP, and ELL requirements, and providing professional development to teachers and staff.
  • Serve as the health department contact and manage health lessons and screenings for all students.
  • Demonstrating that student learning is their top priority through effective leadership actions that build and support a learning organization focused on student success.
  • Working collaboratively to develop and implement an instructional framework that aligns Montessori curriculum with state standards, effective instructional practices, student learning needs, and data from assessments.
  • Actively participating in the Parent Involvement Group to build relationships with CJM families and ensure open communication.
  • Serving as an envoy for Montessori education to the Winter Haven community.
  • Supporting the Principal as he/she executes his/her responsibilities.
  • Interact and work well with students of various age and educational levels in and out of the classroom.
  • Must possess strong verbal and written communication skills, listen well, get clarification, and respond positively to questions and directions.
  • Other duties as assigned.

Minimum Position Requirements:

  • A bachelor’s degree from an accredited college or university.
  • A Florida professional or temporary teaching certificate or a willingness and ability to obtain it prior to starting work.
  • Minimum 5 years teaching experience.
  • A strong working knowledge of and belief in the Montessori Method and a dedication to achieve a full certification within 2 years from AMI (Association Montessori Internationale), AMS (American Montessori Society), Montessori Accreditation Council for Teacher Education, or other widely recognized Montessori program.
  • Dedication to attend a Montessori Leadership Program within 2 years of achieving the above certification.

Preferred Position Requirements:

  • A master’s degree or higher from an accredited college or university, preferably in the field of Education.
  • Supervisory experience in a school or business.
  • Teaching, Supervisory and administrative experience in a Montessori educational setting.
  • Experience working at a public charter school.
  • Certification from AMI (Association Montessori Internationale), AMS (American Montessori Society), Montessori
  • Accreditation Council for Teacher Education, or other widely recognized Montessori program.
  • Certification from a Montessori Leadership Program.


Email cover letter / educational philosophy and your resume / CV to


ADA Statement:

In addition to the duties enumerated above, this position also has physical components as listed below.  The list is intended to give an overview of the position as performed by a person without disabilities.  In conformation with the American with Disabilities Act and UACDC’s policy on Equal Employment Opportunity, UACDC will make reasonable adjustments to enable an otherwise qualified individual with a disability to perform the essential functions of the position with or without accommodation where necessary.


1.  Occasional reaching 2.  Occasional bending 3.  Occasional stooping
4.  Occasional kneeling 5.  Occasional crouching 6.  Occasional stair climbing
7.  Frequent standing 8.  Frequent walking 9.  Frequent sitting
10.  Frequent turning 11. Occasional carrying, pushing and/or pulling up to 10 lbs.


The Duties and Responsibilities, Skills and Abilities listed above are not intended to be an exhaustive list for this position.  They are intended to be exemplary of the level and complexity of work generally performed by a person in this job.  The duties and responsibilities may be changed due to evolution of the position or to reflect the special abilities or disabilities of the person in the position.