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Head of Middle School

Job in Santa Monica, Los Angeles County, California, 90403, USA
Listing for: Crossroads-School-For-Arts-
Full Time position
Listed on 2026-10-18
Job specializations:
  • Education / Teaching
    Middle School, Education Administration
Salary/Wage Range or Industry Benchmark: 120000 - 180000 USD Yearly USD 120000.00 180000.00 YEAR
Job Description & How to Apply Below
The new Head of Middle School will bring deep middle school experience, analytical thinking and planning, high emotional intelligence and excellent communication skills to the role. They will add structure, frameworks and systems where needed, while recognizing and giving consideration to the structures already in place. The Head must build trust within the Crossroads community and provide consistent and transparent communication to faculty, students and families.

The Middle School has been described as “the magical nucleus” of the school, but there is also a need for better definition and articulation of the division’s place between Elementary School and Upper School. The new Head will provide a clear and confident vision for the Middle School and will execute on that vision in collaboration with all key constituencies.

Strategic Priorities The Head of Middle School will be a strategic partner and thought leader who will help strengthen and advance Crossroads’ vision and strategic plan for the Middle School. By working collaboratively with both decisiveness and flexibility, the Head of Middle School will prioritize the following:

Assess curriculum and program, and finalize a published scope and sequence

Evaluate and implement new systems and frameworks as needed.

Consistently build bridges of trust, community, and connection.

Provide mission-aligned vision and direction to the Middle School division.

Help to attract, recruit, and retain a talented and diverse faculty.

Essential Functions Support the Grade-Level Deans who oversee the Student Life Program; serve as counsel for higher-level disciplinary issues

Ensure articulation of diversity, equity, inclusion, and justice principles as they relate at Crossroads, and continue to bring them into the everyday life of the Middle School with the whole child and progressive principles in mind Bring bold and innovative ideas to the table while respecting and honoring Crossroads’ traditions

Build community, culture, and trust

Work with the Assistant Head of Middle School to plan events and programs

Work with Elementary School and Upper School Heads to examine and improve all transitions from Elementary to Middle and Middle to Upper School — such as social emotional learning and curriculum

Work with Elementary School and Upper School Heads to clearly understand, define and articulate each division’s place within the Crossroads ecosystem

Develop strong relationship with the faculty; supervise, mentor, guide, and support them in their everyday activities and in their professional development

Be a visible and available leader to faculty, students, and families

Meet regularly with the Parent Association to share updates and answer questions ATTRIBUTES AND COMPETENCIES Sympathetic and empathetic; high emotional intelligence

Calm, unflappable, and strong in crisis situations

Relationship builder

Invested, excited, and willing to lead

Approachable

Ability to manage ambiguity

Multitasker

Decisive and direct

Ability to make others feel seen, heard, validated, and valued

High emotional intelligence

Warm, community-minded, with a good sense of humor

Philosophy and Core Commitments The School was built upon five basic commitments: to academic excellence; to the arts; to the greater community; to the development of a student population of social, economic, and racial diversity; and to the development of each student’s physical well-being and full human potential.

It is the goal of Crossroads School to provide a strong college preparatory program from which each student will develop a personal commitment to learning, a respect for independent thinking, and an expanding curiosity about the world and its people. We consider certain skills to be essential for all graduates: to read…
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