Windward School, a grade 7-12 college-preparatory, independent day school in vibrant West Los Angeles, is currently seeking an experienced educator to join our Administrative Team as a long-term parental leave Dean of Students (100% FTE) overseeing Grades 11 &12 for the 2026-27 school year (mid-August - mid-February).

A nationwide leader in educational models and practices that excite students about learning, Windward is committed to building a nurturing, inclusive culture. We welcome teachers and staff members who bring skills, qualities, and experiences that demonstrate an understanding of and ability to support our work fostering a diverse school community. 

At Windward, we are dedicated to cultivating an environment that encourages and supports growth and belonging amongst all community members. Windward teachers, parents, and administrators work together to inspire our students to be responsible, caring, well-informed, ethical, prepared, and well-balanced young adults. 

For more information on what Windward has to offer, please visit windwardschool.org/about/careers.

Working as a member of the Collegiate Division team, the Interim Dean of Students is responsible for supporting students in their successful participation in all aspects of school life, both curricular and extracurricular. The Dean plays a hands-on role in daily operations, monitoring student attendance, behavior, and engagement, and responding in real time to student needs. A particular focus of the role is guiding the Senior class in their leadership of the community as well as upholding expectations around attendance, privileges, conduct, and graduation requirements while maintaining strong rapport and accountability.

The Dean of Students partners closely with faculty to address classroom concerns, including behavior management, academic integrity, and student well-being, ensuring consistent follow-through and alignment with school policies. The Dean, in partnership with the Collegiate Division team, communicates regularly and proactively with parents and guardians, addressing concerns with clarity, empathy, and professionalism, and navigating complex or sensitive situations with sound judgment. In addition, the Dean supports student programming, including advisory or seminar structures, student leadership initiatives, and key grade-level events, helping to foster a positive, inclusive, and well-managed school culture. 

Reports to: Division Director

Essential Duties and Responsibilities

The Dean of Students will:

• Know every student as a person and a learner.
• Work with the Associate Division Director and Director of Counseling Services to develop and manage academic and social policies, protocols, and practices that support student development, learning, health, and safety.
• Promote high standards and expectations for academic performance, student leadership, personal integrity, and community responsibility. Support faculty in efforts to create and maintain a productive learning environment.
• Communicate and implement school policies and rules regarding student behavior. Oversee student conduct and maintain appropriate student discipline records. Follow up with faculty, administration, parents/guardians and students regarding consequences of behavioral or academic challenges.
• Participate in the planning and implementation of educational meetings. Coordinate new student orientation and student activities within the division. Assist with student leadership and service learning programs. Oversee special programs and events for attendance by the student body, such as assemblies.
• Collaborate with other Division team members in support of the social, emotional and behavioral needs of the students. Assist in the development of education/prevention programming in such topics as stress and anxiety management; issues related to social and family relationships; concerns in use of social media; transition and coping skills; conflict resolution and mediation; social skills in problem solving; healthy behaviors and relationships.
• Collaborate with the Collegiate Division team and faculty to identify and prioritize needs of students of concern. Provide strategies, advice, support, and guidance to those students and their families as appropriate to the Divisional grade levels, including but not limited to bi-weekly reports and credit reconciliation worksheets. 
• Meet with students, parents/guardians, and faculty regarding student academic needs as well as interpersonal conflicts. Establish consequences for student behavioral infractions. Support positive relationships between faculty and students following student behavioral and academic lapses. Support educational leadership with a developmental focus.
• Maintain close relationships with parents/guardians, educational therapists, and psychological support personnel. Working closely with the divisional counselor, coordinate support based on educational testing and other special circumstances.
• With the Director of Counseling Services, coordinate academic programs for students who need to be out of school and work as a liaison for parents/guardians, outside experts, other school departments as necessary.
• Cultivate mutually beneficial working relationships with colleagues and other professionals; attend conferences and professional meetings as well as school-sponsored events appropriate to position. 
• As an active member of the broader school community, join faculty activities such as faculty meetings, teach students in a classroom setting, and proctor standardized exams. The Dean might participate in the admission process as requested, through prospective student and parent/guardian events and presentations.
• Attend, as assigned, off campus overnight retreats and day-long events off campus to support Collegiate Team programming.
• Maintain regular communication with the Dean of Students for Middle School and the Dean of Students for the Prep Division, ensuring smooth transitions for students as well as symmetry and age-appropriateness of school policies and expectation across divisions.  
• Assume responsibility for other projects as assigned by the Division Director or Head of School.

This is a great chance to be part of a dynamic, close-knit, independent school culture and community. 

We offer competitive compensation and benefits, including:

• Medical, dental, vision insurance
• Paid Holidays and Wellness days
• Retirement Plan, including up to 6% employer match
• School-paid Life and Disability Insurance
• Flexible Spending Account Plans
• FlexCheck (Prorated)
• Lunch Allowance (Prorated)
• MetLife Group Home & Auto Group Discount
• Access to Peak Performance Center to promote physical and mental health
• Wellness Initiatives, including Chair Massages, free Wellness Coaching, Self-Care Reimbursement, and much more!
• Employee Assistance Program
• Upon acceptance to Windward School by the Admissions Committee, employees may apply for tuition remission for their children
• Nurturing, supportive and inclusive community
• And much more!

Salary Range: $115-125k (annual; prorated based on length of assignment), depending on experience.

To Apply: All interested candidates should send a resume and a cover letter via the Application link.

EOE

Requirements

The ideal candidate will possess strong interpersonal and communication skills and proven ability to collaborate with students, families and faculty in a warm, compassionate and nurturing manner.

• A bachelor’s degree; master's degree preferred
• At least 3 to 5 years’ prior experience in education
• Experience working in student life or student support services preferred
• Successful track record working with students and families.
• Excellent organizational and time management skills; detail-oriente
• Strong work ethic and high level of integrity

About Windward School

Windward School is a dynamic grade 7-12 college-preparatory school in vibrant West Los Angeles. Windward’s mission is to challenges each student to achieve excellence in a nurturing, inclusive community. Windward teachers, parents, and administrators work together to inspire our students to be responsible, caring, well informed, ethical, prepared, and well balanced young adults. Windward School offers a competitive salary and an excellent benefits package. For more information, please visit www.windwardschool.org.

Connections working at Windward School