Middle School Dean of Students and Culture

The inaugural Middle School Dean of Students and Culture is a dynamic and visible educational leader who fosters a joyful equitable and inclusive student experience for grades 58. The Dean is responsible for shaping student culture and supporting a vibrant and engaged community aligned with Overlakes mission and values.

This role oversees student programs discipline leadership initiatives wellness programming and co-curricular activities while building meaningful partnerships with students families faculty and staff. The Middle School Dean collaborates closely with the Upper School Dean and Division Heads to ensure continuity of experience and values across grades 512.

Who You Are

• A joyful and visible presence on campusbuilding a community where students feel seen known and inspired to belong and contribute.
• A practitioner of restorative non-coercive discipline who leads with empathy fairness and accountability guiding students toward integrity and self-awareness.
• An exceptional decision-maker who balances compassion with clarity leading with both wisdom and courage in moments of challenge.
• A cultivator of culture and connection fostering relationships that strengthen trust among students faculty families and staff.
• A strategic and steady leader who upholds high standards for student conduct leadership and community responsibility while nurturing emotional well-being.
• A creative problem-solver who approaches complex situations with perspective humor and grace.
• A clear communicator who can connect with students families faculty and staff both verbally and in writing.
• A champion of student voice and leadership empowering students to grow through meaningful engagement and reflection.
• A collaborative partner who works intentionally across departments to align student life wellness and academics in support of the schools mission.
• A mentor and modelgrounded authentic and compassionatewho brings out the best in both students and adults.
• An eager learner and culture sustainer curious and reflective committed to evolving alongside the community they serve.

What Youll Do

Program Development

• Advisory Program: In collaboration with the Division Heads and the Upper School Dean of Students and Culture design implement and evaluate a mission-aligned Advisory Curriculum grounded in Overlakes values and mission. Provide structure resources and training for advisors.
• Traditions & Events: Oversee and preserve key middle school traditions and events (e.g. Spirit Weeks service days socials) while fostering new opportunities for joyful community connection.
• Wellness Integration: Collaborate with the Assistant Head for Inclusive Excellence Director of Experiential Education Director of Health and Wellness Learning Specialists and Personal Counselors to embed wellness social-emotional learning and DEI into student life including flex programming.
• Affinity Program: Lead affinity group programming for both student leaders and affinity advisors (orientations and mid-year touch points). Support affinity group programming including chaperoning excursions and conferences.
• Vision and Oversight for Cocurricular Programs:

- Clubs and student organizations

- Academic teams

- ASB activities and leadership initiatives

- Affinity groups

• Lead and guide student leadership: ASB Affinity leaders captains etc. through their respective programming and community engagement.

Manage Student Culture Discipline & Expectations

• Empower student voice and foster shared ownership of school culture.
• Lead restorative developmentally appropriate systems for student accountability.
• Establish clear expectations for attendance behavior and community responsibility.
• Coordinate with teachers to administer fair consistent and educational discipline.
• Effectively communicate with students and parents balancing empathy mutual respect and fairness while upholding school expectations.
• Partner with Division Heads to ensure fairness consistency and alignment with school values and policies.
• Review and update middle school sections of the Student Handbook annually.

Curate Family & Community Engagement

• Partner with parent volunteers and grade-level representatives to strengthen community connections.
• Collaborate with the Communications team to highlight student experiences and authentic leadership stories.

Who Youll Supervise

• Middle School Advisory Team Leaders
• Middle School Advisors
• Middle School Academic Team Coaches
• Middle School Student Government Faculty Sponsors
• Middle School Club Leaders
• Middle School Affinity Leaders

• Previous experience in student life leadership or educational administration.
• Masters degree in education counseling or educational leadership or equivalent experience.
• Experience with middle school students in independent or secondary schools.

Essential Attributes for Success:

• A deep care for students and nurturing their growth.
• Exceptional communication skillsclear empathetic and inspiring.
• Strong organizational and program management abilities with balance between strategic vision and daily operations.
• Demonstrated leadership in student culture restorative discipline and community building.
• Deep commitment to diversity equity inclusion and belonging.
• Enthusiastic visible presence in daily student life.
• A blend of humility and humor

Physical Requirements:

• Ability to lift up to 10 lbs.
• Ability to sit/stand for extended periods.
• Works in office/outdoor environment.

Equal Employment Opportunity

At The Overlake School we strive to ensure that every employee feels welcomed and valued for their unique perspectives and contributions. From our hiring practices performance reviews raise decisions and opportunities for promotions The Overlake School follows consistent and fair practices to ensure all employees and potential employees have an equal opportunity for employment and advancement based on merit and are not discriminated against because of race color religion national origin age sex veteran status pregnancy childbirth pregnancy-related conditions disability gender gender identity sexual orientation or on any other legally protected basis in the administration of its educational policies financial aid employment and other school-administered programs. Our Human Resources department works with employees to make reasonable accommodations for those that require assistance in being able to participate in the interview process or meet the requirements of their position.

Background Check Policy

The Overlake School conducts background checks for employees after the conditional offer of employment is accepted in compliance with applicable federal state and local laws. Candidates will be asked to authorize these screenings and results will be reviewed by a designated HR representative. The Overlake School reserves the right to modify this policy at any time without notice.

The HR & Payroll Specialist will play a vital role in ensuring smooth and efficient HR processes including payroll administration HRIS management benefits coordination and compliance. This position supports the overall employee experience by maintaining updated records processing accurate payroll assisting with onboarding and offboarding and supporting key HR initiatives aligned with the schools strategic goals.