Job Title: Principal / Head of School

Reports To: Board of Directors

Salary Range: $82,589 – $110,213


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 Principal will lead the development, management, and ultimate success of the school. Reporting to the school’s Board of Directors, this is a full-time leadership position who will be taking the helm of the school for the 2022-23 school year.

The Principal of Cypress Junction Montessori must be a dynamic and competent leader. They will provide leadership for and management of programs and processes related to instruction, personnel management, student support services and student/family activities. The Principal will implement and uphold the school’s mission and guiding principles and maintain professionalism in all following areas including: curriculum, personnel, enrollment, program and service support, organization, planning and analysis, fiscal management, and relationships with the Board of Directors and community.


The Principal provides leadership for and management of programs and processes related to instruction, school operations, personnel management, business management, student support services, student activities and community involvement. This includes but is not limited to the following: 

  • 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.
  • Leading teachers and staff in passionately following the authentic method created by Dr. Maria Montessori in order to provide a genuine, quality Montessori Education to every student.
  • Recruiting, retaining, and developing an effective and diverse faculty and staff; focusing on evidence research, and classroom realities faced by teachers.
  • Demonstrating that student learning is their top priority through effective leadership actions that build and support a learning organization focused on student success.
  • Demonstrating the strong and focused work ethic necessary to lead a successful Montessori school. This includes the ability to work 40-50 hours a week on campus during the school year. It will also require being available during the majority of Extended Care hours.
  • Planning the school calendar and carrying out programs and services.
  • Overseeing the assessment and evaluation of student progress and assisting teachers in developing standards for student achievement.
  • Analyzing student assessments, verifying Montessori curriculum is being effectively implemented, and maintaining data-informed instruction.
  • Maintaining responsibility for the safety and discipline of teachers and staff and, when needed, students.
  • Facilitating professional development and working with teachers and staff including ensuring  completion of Montessori certification within two years of hire and implementing the training in their classrooms.
  • Securing and providing timely feedback to teachers so that feedback can be used to increase teacher professional practice.
  • Providing structure for and monitoring of a school learning environment that improves learning for all of the school’s diverse student population; 
  • Employing and monitoring a decision-making process that is based on CJM’s vision, mission, and improvement priorities using facts and data. 
  • Managing the decision making process, but not all decisions, using the process to empower others and distribute leadership when appropriate.
  • 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.
  • Actively cultivating, supporting, and developing other leaders within the school, modeling trust, competency, and integrity in ways that positively impact and inspire growth in other potential leaders.
  • Managing the organization, operations, and facilities in ways that maximize the use of resources to promote a safe, efficient, legal, and effective learning environment.
  • Interact and work well with students of various age and educational levels in and out of the classroom.
  • Managing a process of regular communications to staff and community keeping all stakeholders engaged in the work of the school.
  • 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 master’s degree from an accredited college or university, preferably in the field of Education.
  • A Florida professional or temporary teaching certificate or a willingness and ability to obtain it prior to starting work.
  • Minimum 5 years teaching experience. 
  • Minimum 3 years supervisory or administrative experience in a school.
  • 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:

  • Teaching, Supervisory and administrative experience in a Montessori educational setting, preferably including  Montessori 
  • 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.