Background

La Jolla Country Day School is pleased to work with DRG to conduct this search. Read the full Opportunity Statement.

Founded in 1926, La Jolla Country Day School (LJCDS) is San Diego's only independent, coeducational school serving students from age three through grade twelve on a single campus. This PreK-12 continuum is a defining strength, allowing students to grow together in a community where leadership, empathy, and self-awareness are learned alongside rigorous academics. LJCDS is guided by a mission to prepare individuals for a lifetime of intellectual exploration, personal growth, and social responsibility and by a core commitment to dignity: the belief that every person has inherent worth and value.

Today, LJCDS serves an engaged and high-achieving student body drawn from across the region. The school enrolls approximately 1,169 students, including up to 500 in the Upper School, and is supported by a deeply committed faculty with an average tenure of ten years. With strong resources and an ambitious program that integrates academics, athletics, arts, service, and global engagement, LJCDS offers students an education that is both demanding and deeply human.

A signature initiative shaping the school's future is The Hub for Human Impact, a new 20,000 square-foot human-centered learning commons opening in fall 2026. Designed to bring students together across disciplines and age groups, The Hub will support design thinking, innovation, entrepreneurship, global collaboration, and experiential learning. It reflects LJCDS's commitment to preparing students not simply for college, but for leadership and impact in an increasingly complex world.

Opportunities and Challenges

The Head of Upper School role presents a compelling leadership opportunity that blends continuity with change. The division is grounded in a strong academic culture, committed faculty, and capable, engaged students while also navigating strategic, cultural, and structural shifts that call for clarity, steadiness, and thoughtful execution.

A central opportunity lies in advancing the Upper School's evolving academic vision. The advanced studies framework reflects a commitment to deeper learning and long-term student success. The next Head of Upper School will steward this work and articulate its value clearly to students, families, and faculty.

Another significant opportunity is strengthening leadership structures and accountability. With an administrative team in transition and department chairs assuming greater responsibility, the incoming Head will have the ability to clarify roles, build a healthy leadership model, and establish consistent expectations that support both growth and excellence.

Culturally, the role offers the opportunity to center decision-making on students while building trust among adults. Balancing empathy with clarity and warmth with accountability will be essential.

The role also includes close partnership with a highly engaged parent community. College counseling in particular is a visible and important area of focus, requiring thoughtful communication and alignment between academic pathways and postsecondary outcomes. Strengthening confidence in the Upper School experience, especially in collaboration with Middle School leadership, will be key to retention and enrollment stability.

Finally, the Head of Upper School will play a central role in integrating The Hub for Human Impact into the academic and co-curricular life of the Upper School, ensuring that its promise translates into meaningful student learning and community engagement.

The Position

The Head of Upper School is the senior leader responsible for the academic, cultural, and operational vitality of grades 9 through 12. Reporting to the Head of School and working closely with the Associate Head of School and fellow division leaders, the Head provides vision, leadership, and daily oversight for a complex and engaged Upper School community.

Responsibilities

• Leading the overall Upper School student experience; setting the tone for a culture rooted in dignity, belonging, and high expectations; and ensuring that students feel known, supported, challenged, and valued.
• Partnering closely with student life and wellness leadership to foster a healthy, inclusive, and developmentally appropriate environment while upholding consistent standards for behavior, engagement, and community life.
• Serving as the division's primary academic leader; stewarding curricular coherence and the continued evolution of the advanced studies framework; and supporting instructional excellence, innovation, and interdisciplinary learning.
• Communicating the academic program clearly and confidently to students, families, faculty, and trustees, ensuring shared understanding of academic pathways, expectations, and outcomes.
• Recruiting, evaluating, coaching, and retaining Upper School faculty and staff, with a strong commitment to professional growth, reflective practice, and continuous improvement.
• Building and leading a healthy administrative team, clarifying roles and responsibilities, strengthening collaboration, and establishing consistent structures for accountability and decision-making.
• Supporting and developing department chairs as instructional and managerial leaders and strengthening systems for faculty feedback, supervision, and evaluation.
• Partnering closely with the college counseling team to align academic pathways with postsecondary planning, strengthen communication with families, and reinforce a student-centered philosophy of college preparation.
• Serving as a visible and steady presence for families, particularly during moments of celebration, challenge, or uncertainty, and fostering strong, trust-based partnerships.
• Supporting admissions and enrollment management for the Upper School in collaboration with school leadership and contributing to retention strategies and long-term enrollment stability.
• Ensuring effective coordination of schedules, programs, staffing, and resources, balancing day-to-day operational excellence with long-range strategic priorities.
• Playing a central role in integrating The Hub for Human Impact into the Upper School academic and co-curricular experience, helping translate its vision into meaningful student learning and interdisciplinary collaboration.
• Participating actively in the life of the school, including attendance at athletic events, performances, experiential programs, and community gatherings.
• Collaborating closely with Middle School and Lower School leadership to ensure continuity, alignment, and smooth transitions across divisions.
• Modeling the school's mission and values and helping shape a compelling, forward-looking vision for the future of the Upper School.

Education, Experience, and Skills

• Significant leadership experience in an Upper School setting, preferably within an independent school
• Academic credibility and the ability to engage meaningfully with faculty around curriculum, pedagogy, and instructional quality
• Experience leading or supporting curricular evolution or strategic academic initiatives
• Proven ability to hire, evaluate, and coach faculty and staff
• Experience building and managing leadership teams, including department chairs and deans
• Experience partnering with a highly engaged parent community around academic pathways and student outcomes
• Strong understanding of adolescent development and student wellness
• A clear, confident communicator with strong organizational and operational skills

Key Personal Characteristics

• Deeply student-centered, with decisions grounded in what best serves students
• Warm, visible, and relational, with the ability to hold adults accountable
• Academically confident and intellectually curious
• Emotionally intelligent and self-aware, able to navigate complexity with steadiness
• Comfortable leading through change and ambiguity
• Thoughtful, fair, and direct in addressing challenges
• Inclusive and values-driven, committed to dignity and belonging
• Optimistic and forward-looking, with a practical, grounded approach
• Strong work ethic for both task completion and complex problem solving
• Energetic and present, with a genuine enjoyment of and engagement in school life

Benefits and Compensation

The Head of Upper School position offers a salary range of $200,000-$230,000. LJCDS offers a comprehensive benefits package that includes medical, dental, vision, and life insurance and a matching 403b retirement plan.

Application Requirements and Search Process

DRG is conducting this search on behalf of LJCDS. 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 one- to two-page PDF writing sample of your choice (newsletter, parent or faculty communication, talk, etc.)
• The names, email addresses, and telephone numbers of five references, as well as the relationship of each reference to the candidate (references will be contacted only at the finalist stage and with the candidate's permission)

Application Status: Presenting candidates as soon as possible

Start Date: July 1, 2026

This position description is based upon material provided by La Jolla Country Day School, an equal-opportunity employer.