Sarasota, Florida
Cambridge, Massachusetts
Washington, D.C.
Posted: 27-Nov-25
Location: Redmond, Washington
Type: Full Time
Salary: $110,000 - 130,000
Categories:
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 position starts July 1st, 2026 and is a 12-month position.
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
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. Please click here to apply.
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
- A joyful and visible presence on campus—building 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 school’s mission.
- A mentor and model—grounded, authentic, and compassionate—who 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 You’ll Do
Demonstrate Leadership and Cultivate Culture
- Develop and articulate a leadership philosophy that guides athletics, ASB, clubs, and co-curricular life.
- Build and sustain programs that reflect Overlake’s values of integrity, compassion, and inclusion.
- Partner with the Middle School Dean of Students & Culture to ensure continuity and coherence of culture across grades 5–12.
Program Development
- Advisory Program: In collaboration with the Division Heads and the Middle School Dean of Students and Culture, design, implement, and evaluate a mission-aligned Advisory Curriculum grounded in Overlake’s values and mission. Provide structure, resources, and training for advisors.
- Leadership Curriculum/Pathway: Design and guide a developmental leadership framework through which students can progress across roles such as club leader, ASB officer, and team captain.
- Traditions & Events: Oversee major upper school traditions and events (e.g., Green & Gold, Senior Celebrations, Winter banquet, Dances, Carnival) while empowering student-led initiatives.
- 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, belonging, and leadership education 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, presentation of annual events, organization of affinity fundraisers, etc.
- Cocurricular Programs: Provide vision and oversight for:
- Clubs and student organizations
- Academic teams (Speech and Debate, Robotics, DECA, etc.)
- 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 and support meaningful student voice contributions and foster shared ownership of school culture.
- Lead restorative, developmentally appropriate, and equitable discipline systems for student accountability and integrity.
- Establish clear expectations for attendance, behavior, and community responsibility.
- Coordinate and advise the Student Review Board (SRB), ensuring fairness and mission alignment.
- Coordinate with teachers to administer fair, consistent, and educational discipline.
- Partner with Division Head and Advisors to effectively communicate with students and parents balancing empathy, mutual respect, and fairness while upholding school expectations to ensure fairness, consistency, and alignment with school values and policies.
- Oversee student attendance, parking, and community conduct expectations.
- Review and update upper school sections of the Student Handbook annually.
Curate Family & Community Engagement
- Partner with parent volunteers and grade-level representatives to foster an inclusive and connected community.
- Collaborate with the Communications team to highlight student experiences and authentic leadership stories.
Who You’ll Supervise
- Upper School Advisory Team Leaders
- Upper School Advisors
- Upper School Academic Team Coaches (DECA, Speech and Debate, Robotics, Model UN, Quiz Bowl)
- Student Review Board Faculty Representatives
- Upper School Associated Student Body (ASB) Faculty Sponsor (Student Government)
- Upper School Affinity Leaders
- Upper School Club Leaders
Requirements
- Previous experience in student life, leadership, or educational administration.
- Master’s degree in education, counseling, or educational leadership or equivalent experience.
- Experience with upper school students in independent or secondary schools.
Essential Attributes for Success:
- A deep care for students and nurturing their growth.
- Exceptional communication skills—clear, 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.