San Diego Jewish Academy
Head of Upper School
San Diego, CA
Background
San Diego Jewish Academy (SDJA) is a pluralistic, independent Jewish day school serving students from early childhood through grade 12 on a single, expansive campus in San Diego. SDJA’s mission is to empower each student to learn for life, guided by Jewish values and rooted in strength of community. SDJA is shaping the foundation of future thinkers, creators, and community leaders by blending modern education with greater purpose and meaning.
The school serves families from across the Jewish spectrum and is a deeply multigenerational community, with alumni who remain closely connected to the school and often return as parents, educators, and community leaders.
SDJA offers a rigorous and personalized academic program designed to challenge and support students at every stage of their development. Small class sizes, close faculty student relationships, and innovative instructional practices foster intellectual curiosity, critical thinking, and resilience. Jewish studies, Hebrew language, and experiential learning are integrated throughout the curriculum, ensuring that students graduate with both strong academic preparation and a confident, thoughtful Jewish identity.
Jewish life is woven seamlessly into daily school life through celebrations, t’fillah (prayer) options, Israel education, and service learning, all within an inclusive environment that honors pluralism and belonging. The school’s vibrant culture extends beyond the classroom through athletics, arts, and hands-on learning experiences that support the growth of the whole child.
SDJA’s 56-acre campus, bordered by open space and overlooking the Pacific Ocean, provides a striking and inspiring setting for learning and community life. State of the art academic facilities, athletic fields, performance spaces, and outdoor learning environments reinforce the school’s commitment to innovation, creativity, and connection. Graduates of SDJA emerge as engaged learners and principled leaders, prepared to contribute meaningfully to their communities and the world.
SDJA at a Glance
Facts and Figures
Year Founded: 1979
School-Wide Enrollment: 582
§ Preschool (18-months-5 years): 101
§ Elementary School (Kindergarten-5th): 251
§ Middle & High School (6th-12th): 230
Employees: 137
§ Upper School Faculty: 27
Operating Budget: $19.6M
Annual Fundraising: $2M
Endowment: 8.7M
Accreditation: Western Association of Schools and Colleges (WASC) and California Association of Independent Schools (CAIS)
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.
A hallmark of MUS is its distinctive experiential learning program, which spans hands-on learning in the school garden to annual grade-level trips across national parks and major U.S. cities, culminating in the transformative senior journey to Poland and Israel. These experiences deepen student-teacher relationships, strengthen grade-level communities, and expand students’ understanding of heritage, culture, and global citizenship.
MUS is also known for its warm and inclusive culture—one where students thank teachers at the end of each class, greet one another with genuine affection, and experience an atmosphere that feels like home. Teachers communicate closely about student wellbeing, celebrate student milestones, and work collaboratively to support each learner on their path to success. This relational environment is paired with high academic expectations, strong college preparation, and a commitment to helping students discover their passions both inside and beyond the classroom. Graduates go on to attend selective colleges and universities across the United States, including some of the most highly regarded and competitive institutions in the nation.
More information about SDJA is available at: https://www.sdja.com/
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.
A central opportunity lies in strengthening how the Upper School’s value and distinctive identity are understood by parents and by current and prospective families. As San Diego’s only pluralistic Jewish day school, SDJA offers a uniquely compelling educational experience. The next Head of Upper School will play a key role in articulating that experience with clarity and consistency, partnering with school leadership to communicate it effectively, and serving as a visible ambassador of the Upper School.
Another important opportunity is supporting faculty through a period of change and reaffirming a strong, positive professional culture. By listening carefully, setting clear expectations, and fostering collaboration and shared purpose, the incoming Head of Upper School can help ensure that faculty feel supported, valued, and energized in their work with students.
Operationally, the role offers the opportunity to strengthen systems, communication, and day-to-day practices within the Upper School. Clear, timely communication and well-aligned processes will reinforce trust and reliability, supporting students, families, and faculty and enabling the division to function at a consistently high level.
Finally, the Head of Upper School will have the opportunity to be an inspirational and highly visible presence in a school that is already excellent. By building strong relationships with students and parents, modeling the school’s values, and leading with optimism and integrity, the next Head of Upper School can shepherd a moment of renewal and help set a positive, forward-looking tone for the entire SDJA community.
The Position
San Diego Jewish Academy (SDJA), a leading independent ECC–12 college-preparatory school, seeks an accomplished, highly relational Head of Upper School to lead grades 6–12. Reporting to the Head of School and serving as a key member of the Senior Leadership Team, the Head of Upper School provides academic, cultural, and operational leadership for the division and plays a central role in advancing SDJA’s mission, values, and long-term strategic priorities.
The Head of Upper School is the chief academic and community leader for grades 6–12, responsible for shaping a compelling and cohesive Upper School experience in which students are known, challenged, supported, and inspired. This leader will work closely with faculty, students, and families to strengthen clarity, confidence, and shared understanding of the Upper School program and its value.
This role requires a leader with deep classroom experience, exceptional people skills, strong operational judgment, and a genuine commitment to student well-being, as well as a nuanced understanding of the evolving landscape of independent and Jewish day school education. The ideal candidate will be visible, approachable, and energized by relationship-building — someone who brings warmth, clarity, and purpose to the work of leading a school community.
Key Responsibilities
Strategic & Instructional Leadership
· 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.
Faculty Leadership & Talent Development
· 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.
Student Life, Well-Being & 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.
Operations & Systems Leadership
· 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.
Family & Community Engagement
· 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.
Collaboration & Leadership Presence
· 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
Salary Range
$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