Upper School Dean of Students and Culture

Description : Why Overlake?

Picture yourself working on 75 acres of nature, minutes from Downtown Redmond, among a community united by a shared sense of purpose, love of learning, and an unwavering belief in the power of people.  At The Overlake School, we value tradition and forward-thinking in equal measure. We laugh together, learn together, and lead with compassion. As part of Overlake’s Academic Leadership team, you’ll help ensure that every employee can thrive—now and for generations to come.

The Details :

Wage : $110,000 - 130,000 annual salary, exempt status. The wage offered will depend on relevant education and / or years of experience.

Work Hours and Location : This position is M - F with occasional evenings and weekends.

The Process : This post will remain open to applications until January 31st. At that time it will be determined, based on the applicant pool, if the posting will remain up for longer. The interview process will be ongoing as the position is posted.

Benefits :

• $5 employee premium for all medical plans
• 100% employee coverage for dental and vision plans
• 35% medical, dental and vision coverage for dependents
• 10 days of paid time off per year
• 5-10% employer match based on years of service
• On-site health and wellness
• Professional development allowance
• Meal allowance for breakfast, lunch, and snacks daily
• Employee Assistance Program
• Long term and short term disability as well as life insurance
• Use of School Library
• New Employee Mentorship Program
• Sabbatical eligibility after 7 years

Why This Role?

The inaugural Upper School Dean of Students and Culture is a visible and inspiring educational leader who cultivates a culture of integrity, inclusion, and engagement for students in grades 9–12. The Dean is responsible for supporting student growth, accountability, leadership, and wellness while building a spirited and connected community aligned with Overlake’s mission and values.

This role oversees student programs, culture, discipline, leadership initiatives, and co-curricular activities while collaborating with students, families, faculty, and staff to ensure a cohesive and mission-driven student experience.

Who You Are

What You’ll Do

Demonstrate Leadership and Cultivate Culture

Program Development

Manage Student Culture, Discipline, & Expectations

Curate Family & Community Engagement

Who You’ll Supervise

Requirements :

Essential Attributes for Success :

Physical Requirements :

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.

Compensation details : 110000-130000 Yearly Salary

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