Employment

Westside School is looking for both teachers and instructional assistants with experience working with children in grades preschool to eighth grade to add to our substitute roster. We also need substitutes for music and performing arts, Spanish, Mandarin Chinese, and physical education.

The ideal candidate will be accessible for early morning calls. Candidates with partial availability during the week are also encouraged to apply. Please submit a resume and references to employment@westsideschool.org.

Compensation

$35.00/hour

To Apply

Please submit a resume and three professional references, to employment@westsideschool.org. Applications missing any portion will be considered incomplete.

Westside School, an independent preschool–8th grade school in West Seattle, is seeking a highly relational, student-centered leader to serve as its next Middle School Division Head. Guided by its mission to help students learn to think critically and act with compassion in a joyful, supportive community, Westside is a place where intellect and heart thrive side by side. Since its founding in 1981, the school has empowered students to meet challenges with imagination and resilience. Families describe Westside as “the school we didn’t know we needed,” a warm and welcoming environment defined by respect, belonging, and genuine partnership among teachers, students, and families.

Reporting to the new Head of School, Dr. Daryl Wright, the Middle School Division Head oversees all aspects of the program for grades 5–8, collaborating with faculty and staff to guide approximately 150 students through a formative stage of growth. The Division Head joins a collegial Educational Leadership Team to deepen alignment across divisions and champion the continued evolution of teaching and learning. This leader will bring steadiness and perspective to a dedicated faculty, strengthening team culture and supporting Westside’s commitment to the whole child.

The next Middle School Division Head will enter a community ready for stability and shared direction after a period of transition. With optimism and vision, the new leader will nurture confidence among faculty and families, communicate transparently, and celebrate the spirit that makes Westside distinct. They will uphold the school’s promise to serve a wide range of learners with creativity, empathy, and high expectations, striking a thoughtful balance between support and stretch for every student. This person will help articulate the Middle School’s identity and collaborate across the institution to share the impact of a Westside education with clarity and pride.

The ideal candidate will lead with energy, humility, and high emotional intelligence— someone who finds meaning in guiding early adolescents and the educators who inspire them. A clear-sighted communicator and trusted partner, this leader will cultivate consistency, enthusiasm, and shared purpose across the division. This is an exciting opportunity for the Middle School Division Head to help shape the school’s next chapter, uniting a vibrant community around scholastic curiosity and authentic connection. 

Salary Range: $135,000-$145,000

TIMELINE

• Application deadline: December 12, 2025
• Semifinalist interviews: Week of January 5, 2026
• Finalist interviews: Week of January 26, 2026
• Announcement: February 2026
• Start date: July 1, 2026

STRATEGIC PRIORITIES

In partnership with the Head of School and divisional colleagues, the Middle School Division Head will be expected to advance the following priorities:

• Rebuild trust and stability within the Middle School. Strengthen consistency, communication, and follow-through after multiple leadership transitions. 
• Clarify and champion the Middle School identity. Articulate a compelling vision that celebrates the distinctiveness of Westside’s Middle School experience while ensuring alignment with the Lower School and the school’s overall mission.
• Cultivate a culture of professional learning and development. Support and celebrate a talented faculty through meaningful opportunities for professional development, reflection, and collaboration. Establish consistent systems for feedback and evaluation that encourage ongoing professional excellence while maintaining trust and autonomy.
• Advance programs and practices that center student well-being and growth. Advocate for the school’s commitment to social-emotional learning, restorative practices, and differentiation that meets the full range of learners. Elevate student voice and agency, ensuring that every learner feels known, challenged, and supported.
• Partner with colleagues in admissions, advancement, and communications to tell the Westside story. Highlight the impact and outcomes of a Westside education, sharing stories that connect current families, alumni, and the broader community.

ESSENTIAL FUNCTIONS

• Maintain and help focus the school’s mission, vision, and values
• Foster a highly engaged student and faculty culture in the middle school, characterized by high expectations, joyful learning, and a strong sense of community
• Build strong relationships with students, parents, and educators
• Coach, mentor, and evaluate middle school teaching staff, with particular attention to early career teachers
• Support teaching teams in achieving a high quality of collaboration and instructional practice
• Champion and facilitate curricular planning for the middle school, with a focus on inquiry-based, project-based, and experiential learning
• Provide positive support for students in achieving academic and personal success, including oversight of student support structures and the MS Dean role
• Oversee middle school communications, including the curricular and program sections of teachers’ newsletters
• Organize and facilitate middle school faculty meetings
• Attend ‘special circumstances’ parent/teacher conferences and be available for check-ins and portfolio conferences
• Serve as the point person for student behavior plans, partnering closely with the Middle School Dean
• Develop strong systems for positive parent involvement and communication
• Collaborate with the Heads of Lower School, Early Learning, and the Head of School to strengthen cross-divisional connections
• Work with the Head of School and Educational Leadership Team to plan professional development, retreats, and faculty growth initiatives
• Lead hiring committees for middle school faculty and staff
• Serve as the main point of contact for parent questions, concerns, or feedback related to the middle school program
• Build the middle school schedule in conjunction with other division heads
• Participate in recess, dismissal, and other duties weekly
• Meet weekly with the Head of School
• Other duties as assigned

QUALITIES AND ATTRIBUTES

The next Middle School Division Head will be an inspiring leader who cultivates trust through clarity and follow-through, strengthening the confidence and cohesion of the division. Rooted in a love for middle school-aged children and a belief in centering the whole child, this leader will model empathy, visibility, and authenticity in every interaction. As an instructional leader, they will nurture professional growth and proactive support for both students and teachers while preserving the creativity and autonomy that define Westside’s faculty culture. With humility, humor, and high EQ, the Division Head will unite students, faculty, and families around a shared sense of purpose, fostering an environment that honors every student’s capacity to grow and lead.

Additionally:

• Skilled and transparent communicator - both a thoughtful listener and an articulate messenger
• Culturally responsive practitioner with a deep commitment to diversity, equity, inclusion, and social justice
• Proactive problem-solver who supports students, families, and faculty with empathy and consistency
• Experienced middle school educator and leader who understands adolescent development and differentiation
• Ability to balance vision with day-to-day pragmatism
• Reflective, forward-thinking, and grounded in the realities of teaching and learning
• Brings sincerity, humor, and high energy to leadership and community life

QUALIFICATIONS AND REQUIREMENTS

Westside School is most interested in finding the best candidate for this opportunity and encourages people to apply if they feel they meet most of the following qualifications:

• Advanced degree in teaching, educational leadership, curriculum and assessment, or a related discipline
• Proven success in a position of faculty leadership
• Prior classroom teaching experience, preferably in middle school
• Experience recruiting, hiring, supporting, and retaining talented, diverse, and mission-aligned faculty
• Demonstrated success leading mission-aligned change
• Strategic and detail-oriented approach to leadership
• A passion for curriculum development and teacher growth

How to Apply

Westside School does not discriminate on the basis of sex, race, creed, color, national origin, age, veteran or military status, sexual orientation, gender expression or identity, or disability.

Westside School fosters a vibrant culture of belonging, recognized by the Northwest Association of Independent Schools as a defining strength. Rooted in joyful learning, meaningful relationships, and mutual respect, we inspire creativity, innovation, and community. Our expert educators thrive in an inclusive environment that values diverse perspectives, integrated curriculum, and project-based learning. Supported by beautiful, mission-driven facilities, we celebrate different backgrounds and prioritize inclusion. We welcome applicants from all cultures and communities to apply.

Interested candidates should submit the following materials confidentially in one single PDF file via https://bit.ly/Westside_MSHead_AppForm: 

• A cover letter indicating your particular interest in and qualifications for the position
• A current resume
• A statement of educational philosophy
• The names, email addresses, and telephone numbers of five references, including at least two recent supervisors. References should speak to your 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). Please indicate your relationship with each reference (i.e. supervisor, colleague, or direct report).

Please address any questions by email to maryrose@strategenius.org.