Dean of Students Collegiate Division (Parental Leave 2026-2027)

Windward School • Los Angeles, CA

14h • Onsite

About The Position

Windward School, a grade 7-12 college-preparatory, independent day school in West Los Angeles, is seeking an experienced educator for a long-term parental leave position as Dean of Students (100% FTE) overseeing Grades 11 &12 for the 2026-27 school year (mid-August - mid-February). Windward is a leader in educational models and practices, committed to fostering a nurturing, inclusive, and diverse school community. The school aims to inspire students to be responsible, caring, well-informed, ethical, prepared, and well-balanced young adults through collaboration between teachers, parents, and administrators.

Requirements

• Strong interpersonal and communication skills
• Proven ability to collaborate with students, families and faculty in a warm, compassionate and nurturing manner.
• A bachelor’s degree
• At least 3 to 5 years’ prior experience in education
• Successful track record working with students and families.
• Excellent organizational and time management skills; detail-oriented
• Strong work ethic and high level of integrity

Nice To Haves

• Master's degree preferred
• Experience working in student life or student support services preferred

Responsibilities

• Support students in their successful participation in all aspects of school life, both curricular and extracurricular.
• Play a hands-on role in daily operations, monitoring student attendance, behavior, and engagement, and responding in real time to student needs.
• Guide the Senior class in their leadership of the community and uphold expectations around attendance, privileges, conduct, and graduation requirements.
• Partner 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.
• Communicate regularly and proactively with parents and guardians, addressing concerns with clarity, empathy, and professionalism, and navigating complex or sensitive situations with sound judgment.
• Support 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.
• 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 topics such 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 students and their families as appropriate.
• 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.
• 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.
• Join faculty activities such as faculty meetings, teach students in a classroom setting, and proctor standardized exams.
• 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.

Benefits

• 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
• Tuition remission for their children (Upon acceptance to Windward School by the Admissions Committee)
• Nurturing, supportive and inclusive community

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level