Full TimeSchool Leadership Apply by July 9, 2026

Dean of Secondary School

Estimated Salary
USD 83,000 per year
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Description

Position Summary
Are you a visionary educator who thrives at the intersection of student support and instructional excellence? Pilgrim School is seeking a Dean of Secondary School to serve as a dynamic leadership partner in driving our ambitious, future-focused vision for learning. This isn't a traditional enforcement role; it is a high-visibility, relational leadership position designed for someone who believes that a thriving school culture is the foundation for academic innovation. As an on-the-ground leader of our division, you will bridge the gap between big-picture strategy and daily classroom reality, ensuring that every student is seen, supported, and challenged to reach their full potential.


Major Areas of Responsibility
• Act as a primary point of contact for families regarding student conduct and well-being, building trusting partnerships that align the home and school experience.
• Provide holistic student support by triangulating academic, behavioral, and social-emotional information to design and monitor effective student interventions.
• Lead the daily implementation of the school’s discipline philosophy, ensuring a safe, respectful, and consistent environment through a high-visibility presence in all communal and transitional spaces.
• Conduct daily classroom walkthroughs and partner with the Director to provide faculty with real-time feedback, ensuring pedagogical standards and student-centered design are executed with consistency.
• Direct the daily operations of school life in the Secondary School, including announcements, assemblies, attendance, and front-office logistics to maintain a predictable and rigorous divisional rhythm.
• Serve as a core member of the Secondary Leadership Team, acting as a proxy for the Director and providing critical updates on instructional trends, faculty needs, and divisional health.
• Teach one class in the Secondary School, modeling the school’s pedagogical standards and fostering a love of learning in students.

Requirements

  • Act as a primary point of contact for families regarding student conduct and well-being.
  • Provide holistic student support.
  • Lead the daily implementation of the school’s discipline philosophy.
  • Conduct daily classroom walkthroughs and provide faculty feedback.
  • Direct daily operations of school life in the Secondary School.
  • Serve as a core member of the Secondary Leadership Team.
  • Teach one class in the Secondary School.
Interested in this position? Submit your application to Pilgrim School before the deadline.
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DEADLINE: July 9, 2026

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