What are the responsibilities and job description for the Private Middle School Director position at The Pioneer School, Inc.?
We are seeking an experienced, energetic, and mission-driven School Director to lead a small, independent middle school on a beautiful wooded campus in St. Augustine, Florida, just minutes from historic downtown and the beaches.
This role requires a rare blend of skills:
We are looking for someone who can lead a school and actively help bring its program to life each day. This is not a traditional desk-bound administrative role. It is for someone who wants to be in the middle of a vibrant school community—working with students, supporting teachers, partnering with parents, solving problems, and helping shape the daily experience of adolescent learners.
About Our School
The school was founded in 2016 and our pedagogy is inspired by Waldorf, Montessori, and project-based learning philosophies. We serve adolescents during a pivotal stage of development and intentionally cultivate a school culture that is warm, challenging, and deeply human. Our community includes dedicated, loving teachers and highly engaged, intentional parents. The school is financially stable and well supported.
We emphasize:
- Social and emotional learning
- Kindness, inclusion, and character
- High school preparation
- Outdoor time and experiential learning
- Leadership development
- Human and life skills
- Performance, confidence-building, and public speaking
- Encouraging students to expand their comfort zone
The Role
The Director will provide overall leadership for the school while remaining meaningfully involved in student life and programming.
Responsibilities include:
- Leading day-to-day school operations
- Supporting, mentoring, and supervising faculty
- Building strong relationships with families
- Upholding and evolving the school’s mission and culture
- Addressing behavioral concerns through restorative conversations and mediation
- Communicating with parents regarding discipline, expectations, and support plans as needed
- Upholding the code of conduct with fairness, growth-mindset, and consistency
- Strategic planning and long-term sustainability
- Developing and partnering with a Board of Trustees
- Teaching or co-teaching select enrichment classes in leadership and life skills, especially during the transition period
- Being a visible, engaged presence on campus
This is a full-responsibility leadership position whose demands extend beyond a standard 40-hour workweek. The rhythm of school leadership includes occasional evening events, family communication, planning, jumping in wherever needed, and responsiveness outside regular school hours.
Ideal Candidate
The ideal candidate will have:
- Experience in school administration (Director, Principal, or similar leadership role)
- ESE experience and understanding of how to serve diverse learners
- Strong teaching instincts and comfort working directly with middle school students
- Excellent communication and organizational skills
- A warm, steady presence with clear leadership instincts
- Alignment with progressive, child-centered education
- A sense of humor, humility, and flexibility
Compensation
- Salary: $55,000-$65,000 with opportunity for growth as enrollment increases
This opportunity is best suited for someone motivated by purpose, autonomy, meaningful relationships, and the chance to lead a truly special school community.
Founder’s Transition Note
This leadership transition is intentional and rooted in care for the long-term health of the school. After building and stewarding this community, we are seeking the right person to honor its values while bringing fresh energy, ideas, and leadership to its next chapter. We will support a thoughtful transition and want the next director to be set up for success.
Location
St. Augustine offers a rare quality of life with historic charm, natural beauty, and proximity to the beach.
If you are excited by the idea of leading a mission-driven school while staying connected to students, teachers, and the real daily work of education, we would love to hear from you.
Pay: $55,000.00 - $65,000.00 per year
Application Question(s):
- Please include a short letter of interest introducing yourself, sharing why this role interests you, and what strengths you would bring.
Work Location: In person
Salary : $55,000 - $65,000