San Diego Jewish Academy - Head of Upper School

Maimonides Upper School

The Maimonides Upper School (MUS) plays a defining role in the SDJA experience. Serving students in grades 6–12, MUS offers a rigorous academic program within a close-knit, relationship-centered community where students are known deeply and supported wholeheartedly. Small classes and individualized attention support a broad range of Advanced Placement courses, experiential learning that connects coursework to real-world application, and rich opportunities in athletics, the visual and performing arts, and student leadership.

Opportunities and Challenges

The Head of Upper School role offers a compelling leadership opportunity at an important moment for the division. The Upper School is grounded in a strong legacy, an excellent academic program, and a dedicated, talented faculty, while also navigating a period of transition that calls for clarity, steadiness, and thoughtful leadership. This moment offers the opportunity to reinforce confidence, alignment, and momentum across the division.

·        Serve as the chief academic and cultural leader of the Upper School, ensuring excellence in teaching, learning, student experience, and outcomes.

·        Partner with the Head of School and Senior Leadership Team to advance strategic priorities and articulate a clear, compelling Upper School program that is understood and valued by students and families.

·        Lead ongoing curriculum review, innovation, and vertical alignment to ensure rigor, relevance, and continuity across divisions.

·        Promote and model best practices in teaching, assessment, differentiation, and inclusive pedagogy.

·        Recruit, hire, develop, and retain exceptional faculty and staff.

·        Foster a culture of professional growth through coaching, feedback, evaluation, and differentiated professional development.

·        Build trust, collaboration, accountability, and shared purpose among faculty.

·        Lead regular faculty meetings that address operational needs while engaging faculty in thoughtful conversation around pedagogy, student development and school culture.

·        Oversee all aspects of Upper School student life, including academics, advising, discipline, attendance, and social-emotional health.

·        Cultivate a positive, inclusive, mission-aligned and values-driven school culture grounded in SDJA’s core values and Jewish identity.

·        Ensure clear, fair, and consistent student policies and practices.

·        Partner closely with counselors, learning specialists, and student support teams to address academic, social, emotional, and developmental needs of students.

·        Oversee day-to-day Upper School operations, including scheduling, staffing, supervision, and academic programming.

·        Develop and manage the Upper School budget in collaboration with the Business Office, ensuring responsible and strategic stewardship of resources.

·        Ensure compliance with accreditation standards, school policies, and regulatory requirements.

·        Use data and metrics to inform decision-making, evaluate program effectiveness, and drive continuous improvement.

·        Serve as a visible, accessible, and engaged leader for students, families, and faculty.

·        Build strong collaborative relationships with parents and guardians through communication that is consistent, clear, proactive, and transparent.

·        Partner with Admissions, Advancement, and College Counseling to support recruitment, retention, and long-term success of students.

·        Strengthen community connection and engagement within the Upper School and across the broader SDJA community.

·        Serve as a trusted advisor to the Head of School on matters related to Upper School programs, personnel, culture, and community.

·        Work closely with ECC and Lower School division heads to ensure curricular and cultural alignment across the ECC–12 experience.

·        Model professionalism, integrity, empathy, and values-aligned leadership in all interactions.

Core Competencies & Leadership Attributes

The ideal candidate will demonstrate:

·        Deep commitment to adolescent development and student-centered learning.

·        A forward-thinking vision for the future of independent and Jewish day school education – balancing tradition, innovation, and market realities.

·        A highly relational, service-oriented leadership style; someone who is personable, empathetic, and responsive to students, families, and colleagues.

·        Demonstrated success leading faculty and staff through periods of growth, challenge, or change.

·        Strong communication skills and the ability to build trust, clarity, and confidence within a school community.

·        Sound judgment, emotional intelligence, and comfort navigating complex situations with care and transparency.

·        Proven ability to inspire, mentor, and mobilize faculty, students, and families.

·        Ability to lead effectively in a dynamic, fast-paced school environment

Desired Qualifications

·        Advanced degree in Education or a related field (doctorate preferred).

·        7–10+ years of educational leadership experience, including senior-level administrative responsibility.

·        Significant teaching experience at the middle and/or high school level.

·        Demonstrated success leading an Upper School or comparable division in an independent, public, or Jewish day school setting.

·        Strong expertise in curriculum design, assessment, instructional leadership, and faculty evaluation.

·        High digital fluency and ability to leverage technology to enhance teaching, learning, and school operations.

·        Exceptional interpersonal skills and a collaborative leadership orientation.

Benefits and Compensation

San Diego Jewish Academy offers a thoughtful and competitive compensation and benefits package designed to support the well-being of employees and their families. Benefits include:

• Medical, dental, vision, and life insurance
• Short- and long-term disability coverage
• Flexible Spending Accounts (FSA) for healthcare and dependent care expenses
• A 401(k)-retirement plan with a generous employer match
• Additional benefits and resources

$160,000–$190,000, commensurate with experience and qualifications.

Application Requirements

DRG is conducting this search on behalf of San Diego Jewish Academy. Interested candidates should submit, as soon as possible, materials including the following:

·        A cover letter indicating why they are particularly interested in and qualified for the position

·        A current resume

·        A statement of leadership philosophy

Application materials should be uploaded directly on the DRG website (www.drgtalent.com) by visiting the San Diego Jewish Academy listing.

Application Status: Accepting Applications                                              

Start date: July 2026

This position description is based upon material provided by San Diego Jewish Academy, an equal-opportunity employer.

To apply for this position, please click HERE.

Tani Weissman, Partner,  tweissman@drgtalent.com

Shanna Jadwin, Talent Consultant, sjadwin@drgtalent.com