Head of Middle School

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 well, to write clearly and coherently, to study effectively, to reason soundly, and to question thoughtfully.

Through the educational process, we assist students in gaining self-esteem, self-knowledge, and respect for the knowledge and opinions of others. We believe that education must not be a race for the accumulation of facts, but should be an enriching end in itself. We also believe that education is a joint venture among students, parents and teachers. To be effective with young people, teachers and parents must themselves continue to learn, so that they may perceive the young accurately and treat them wisely.

We believe that the arts are an essential part of the curriculum and that it is important for students to express themselves creatively and to use their imaginations freely. Therefore, music, drama, visual arts, film, writing and dance are significant parts of student life at Crossroads.

Through our academic and extra-curricular programs, we seek to promote social, political and moral understanding, and to instill a respect for the humanity and ecology of the earth.

We understand that there are many kinds of intelligence, and the traditional academic, cognitive area is one. Other important areas of intelligence are intuition, imagination, artistic creativity, physical expression and performance, sensitivity to others and self-understanding. To neglect any of these areas is to limit students in the development of their full human potential.

We believe that the uniqueness of children is revealed in their very existence and that it is the School’s responsibility to foster their innate sense of the mystery and joy of life.

Equity and Inclusion  

Crossroads is a welcoming, inclusive community that seeks to reflect the diversity of the greater Los Angeles area and encourages the exchange of multiple viewpoints and experiences. The diversity of Crossroads’ families, faculty, and staff is apparent in their varied social, economic, and racial backgrounds; belief systems; ethnicities and religions; sexual orientations, gender expressions and identities; family structures; and much more. Crossroads’ diversity enriches the learning experience, exposing students to people of differing backgrounds and perspectives and helping them develop empathy and cultural competency. It also builds their awareness of systematic social inequities and empowers them to advocate for a more just world.

THE SCHOOL

Crossroads School for Arts and Sciences is a leading progressive school offering an educational environment as nurturing as it is inspiring. Founded in 1971, the community of 1,210 kindergarten through 12th graders connect and challenge one another in deep and meaningful ways. The extraordinary faculty and staff serve as academic and personal mentors as Crossroads students grow from 5-year-olds into young adults who are poised to effect positive change in the world.

Campus and Geography

Crossroads School has two campuses located a few blocks apart in a distinctly urban area of Santa Monica, California and easily reached by multiple forms of transportation. Santa Monica is located in Los Angeles County, enviably situated alongside the Pacific Ocean. A vibrant and diverse city, Santa Monica has something for everyone, from world-class restaurants to a vibrant art scene to street performers at the Third Street Promenade. 

The Norton Campus is home to:

• The Elementary School (grades K-5)
• The Joanie Martin Community Room, a multi-purpose space for events
• The K-12 Sports Center, which features a gymnasium, pool, and athletics field

The 21st Street Campus is home to:

• The Middle and Upper Schools (grades 6-12)
• The Alley, a vibrant centerpiece of campus life
• The School’s administrative offices
• Bezdek Center for Performing Arts (New 2026)

THE PROGRAM

Crossroads strives to prepare students to think critically, express themselves openly and respectfully, and commit themselves to lives that value community engagement and leadership. Crossroads aims to deliver a transformational educational experience that helps students find their passions, broaden their horizons, and develop the leadership skills they will use to make meaningful differences in the world around them.

Middle School

Middle School offers students opportunities for new experiences, increased freedom, and greater personal responsibility. Students discover new ideas through literature, experimentation, problem-solving, and discussion. Crossroads’ unique Core program integrates English, geography, social studies, and history to provide an interdisciplinary look at social movements and world events, while their Options program allows students to explore a wide variety of subjects outside of the curriculum. Supportive feedback from adults is a hallmark of the Middle School, where the educational environment honors process as well as product, and students flourish in a cooperative and collaborative learning environment.

The Middle School experience is defined by a harmonious balance of guidance and exploration. Crossroads students receive tailored instruction that channels their curiosity into unfamiliar curricular terrain and helps them make informed choices about their own educational pursuits. Surrounded by adults who understand and value this crucial developmental stage, students enter meaningful conversations with teachers, coaches, deans, and administrators. The Crossroads faculty members are mentors who create an environment for students to work collaboratively while fostering strong relationships.

The Middle School is characterized by exposure to new ideas and the freedom to explore developing interests. Self-advocacy and self-expression flourish as numerous Options classes and rotations in P.E. and the arts introduce new subject matter and inspire students to make educated decisions about their academic and extracurricular pursuits. Crossroads students joyfully tackle new material while sharpening their critical thinking and problem-solving skills. As they begin appreciating uncertainty, they also start seeking out intellectual complexities on their own by asking thoughtful questions and making connections across disciplines.

Fast Facts 

Enrollment: 1210 (Middle School 335)

Students who identify as people of color: 56%

Full Time Faculty: 132

Faculty who identify as people of color: 46%

Campus size: ~70 acres

Affordability Program Budget: $11 million

Qualifications

• Bachelor’s degree required; advanced degree preferred
• 7-10  years of experience in a K12 school environment; independent school experience preferred
• 2-4  years of supervisory/management experience  
• Experience in progressive education and as a teacher and administrator in grades 6-8
• Deep knowledge of and passion for students in this age range and what it means educationally and socially
• Experience with DEIJ and strong value placed on the principles
• Experience in navigating challenging conversations about sensitive issues
• Excellent written and verbal communication skills
• Ability to evaluate people and systems and provide feedback and guidance

Interested candidates are invited to submitthe following materials confidentially as a single PDF file: ​​​​

• A cover letter indicating the candidate’s particular interest in and qualifications for the position

• A current résumé/CV

• A statement of educational philosophy

• The names, addresses, and telephone numbers of three references, including at least one recent supervisor. References should speak to the applicant’s ability to be an effective educator and administrator, to work successfully with children, and to work collaboratively and collegially with adults (references will be contacted only with the candidate’s permission).

Search Calendar

Applications due:December 11, 2026    

Semifinalists interviews:Mid-January 2027

Finalists interviews:Early to Mid-February 2027

Hiring announcement:March 2027