IMMEDIATE INTERIM OPPORTUNITY
Interim Head of School
Reports to : Board Chair
Duration : 9 Months
Location : Cottage Country
Start 17th August 2026
This is a fantastic opportunity for a seasoned professional to utilize their talents to support a critical independent school who serves a small, tightly connected community and is entering a period of transition and organizational reset. For the next 9 months they require an experienced leader to provide strong administrative direction, process redesign, community confidence‑building, drive engagement with parents, and conduct significant work in enrollment stabilization and organizational clarity.
This is a role requiring someone who can “fly the plane” day‑to‑day while also assessing and improving the underlying structures, processes, community engagement and team performance.
Key Mandates & Priorities
First 90 Days
- Conduct a full administrative assessment of people, processes, workload, and role clarity.
- Identify whether issues are personnel‑based, skill‑based, or process‑based .
- Streamline or redesign key workflows, ensuring consistency, accountability, and follow‑through.
- Build trust and psychological safety with faculty.
- Understand enrollment dynamics and begin engaging parents in a transparent, supportive way.
- Strengthen communication channels across faculty, admin staff, the Board, and parents.
Months 4–9
Lead the school’s full operational cycle including PD week, opening‑day readiness, reporting cycles, community events, conflict resolution, and parent relations.Implement a set of administrative standards , policies, and procedures that strengthen clarity and reduce organizational friction.Develop an enrollment stabilization plan , leveraging messaging, community presence, and parent engagement.Support the Board in preparing for the permanent Head of School search, including documenting processes, capabilities, gaps, and recommended future structure.Coach and mentor the Vice Principal and admin support staff.Expected Challenges
Parent anxiety and high expectations , especially given pandemic‑era dynamics and increased tendencies toward intervention in classroom matters.Faculty fatigue and apprehension toward another leadership transition.Enrollment pressure , as declining numbers threaten long‑term financial sustainability.A small community environment , where confidentiality, professionalism, and diplomacy are critical.Limited administrative resources , requiring hands‑on leadership and a roll‑up‑your‑sleeves approach.Deliverables
Administrative review and reorganization plan , including staffing, processes, and role clarity.Stabilized operational environment , ensuring reliable administrative execution.Community engagement and communication plan to rebuild trust and improve parent relationships.Enrollment plan , with clear short‑term strategies and long‑term recommendations.Faculty‑trust rebuilding framework , including feedback loops, predictable communication rhythms, and leadership presence.Board reporting and advisory support , including monthly updates and documentation to support future recruitment.Transition package to support onboarding of the permanent Head of School.Ideal Candidate Background
Experience in independent schools is preferred.Post‑secondary leaders or Principals from the public school system would also be interesting candidates.Must demonstrate :Strong administrative leadershipExceptional communication and community engagement skillsAbility to manage parent behavior and expectations with confidence and calmHigh EQ, diplomacy, and relationship‑buildingAbility to stabilize and reassure facultyExperience diagnosing organizational health and designing operational improvementsLeadership Attributes
Supportive, visible, and present with teachers, parents, and students.A strong communicator , able to calm anxious parents and manage conflict constructively.Confident but humble , with a collaborative and relational leadership style.Able to lead change without triggering defensiveness , maintaining trust and stability.Comfortable working in a small, tightly knit environment with high visibility.Skilled at listening deeply before acting.PLEASE SEND YOUR CV (AS A WORD DOC) TO :
Interim.Applications@LHHknightsbridge.com (Subject : Job Title)
Lee Hecht Harrison Knightsbridge Corp. is committed to providing equitable treatment and accommodation to ensure a barrier‑free recruitment process. In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act and our AODA policy, a request for accommodation will be accepted as part of the hiring process. If you require accommodation to apply or if selected to participate in an assessment process, please provide your accommodation needs in advance to the Recruitment Lead for this opportunity.
We thank all interested candidates in advance; however, only individuals selected for interviews will be contacted.
February 2026
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