Executive Assistant to the Head’s Office

Why Overlake?

Picture yourself working on 75 acres of nature, just minutes from Downtown Redmond. Our community is united by a shared sense of purpose, a love of learning, and an unwavering belief in the power of people. 

We value tradition and forward-thinking in equal measure. We laugh together, learn together, and lead with compassion. As part of Overlake’s Administrative Support team, you’ll help ensure that every employee can thrive—now and for generations to come. 

The Details:

Wage: $100,000-$110,000. The wage offered will depend on relevant education and/or years of experience.

Work Hours and Location: Full-time, Exempt, M-F, occasional evenings and weekends (1-2 times/mo. during the school year for events and/or board meetings)

The Process: Please include a cover letter. This position will remain open until filled. 

Benefits: 

• $5 employee premium for all medical plans
• 100% employee coverage for dental and vision plans
• 35% medical, dental and vision coverage for dependents
• 20 to 30 days of paid time off based on tenure for full-time 12-month staff 
• Paid Holidays when school is fully closed
• 5-10% employer match based on years of service and employee contribution
• On-site health and wellness
• Professional development allowance
• Up to $1,850 meal allowance for breakfast, lunch, and snacks through on-campus dining.
• Employee Assistance Program
• Long term and short term disability as well as life insurance
• Use of School Library
• New Employee Cross-Department Mentorship Program

A Role at the Center of It All

This is not a traditional executive assistant role.

At Overlake, the Executive Assistant is a trusted, high-impact partner who sits at the center of the institution’s leadership, operations, and community life. This role ensures that the Head of School’s Office runs with clarity, precision, and foresight and that leadership is able to operate at its highest level.

You will be the person who brings order to complexity, anticipates what is needed before it is asked, and ensures that the most important work of the school moves forward with purpose and care.

For the right person, this is deeply meaningful work. You will have visibility into the full life of the school, from strategic initiatives to daily decision-making, and you will play a key role in shaping how leadership shows up to the community.

Partner Closely with the Head of School

You will serve as a proactive partner, ensuring the Head is fully prepared, focused, and able to lead effectively each day.

• Manage a complex, high-volume calendar with warmth, diplomacy, precision, and sound judgment.
• Prepare briefing materials, background context, and follow-up actions for key meetings.
• Ensure the Head’s Office operates smoothly and reflects the professionalism and warmth of the school.
• Anticipate needs, identify efficiencies, and solve problems before they surface.
• At times, manage communications on behalf of the Head. 

Support Strategic and Institutional Work: 

You will help move critical initiatives forward across the school.

• Coordinate timelines and track progress for major initiatives such as strategic planning, accreditation progress, and leadership searches.
• Synthesize information from across teams to support decision-making.
• Keep complex, multi-stakeholder projects organized and on track.

Partner with the Assistant Head of School for Inclusive Excellence: 

You will provide essential coordination and support for work that strengthens the school’s community.

• Manage scheduling, logistics, and documentation for the programs and initiatives as well as the assistant head’s calendar with precision and sound judgment.
• Support communication and coordination for work related to equity, inclusion, and community engagement.

Serve as Liaison to the Board of Trustees: 

You will play a key role in supporting effective governance.

• Coordinate all logistics for Board and committee meetings.
• Prepare agendas, materials, minutes, and records with accuracy and discretion.
• Maintain confidential governance documents and support Trustee onboarding.
• Manage the Board portal (Boardable), ensuring materials are accessible and well organized.

Strengthen Systems, Technology, and Data Use: 

You will help the Head’s Office model operational excellence.

• Design and maintain digital systems that improve visibility and workflow.
• Use Microsoft 365 tools and others to create efficient processes, dashboards, and reports.
• Leverage emerging tools, including AI, to streamline work and improve communication.
• Provide clear summaries, trends, and insights to support leadership decisions.

Represent the Head’s Office to the Community 

You will often be the first point of contact and a key ambassador for the school.

• Engage with students, families, faculty, staff, trustees, and external partners with warmth and professionalism
• Coordinate and staff major institutional events, including Board meetings, graduation, and community gatherings.
• Help ensure a consistent, high-quality experience across school events and interactions.

Who Thrives in This Role

This role is for someone who finds joy in being the person behind the scenes who makes everything work.

• You are consistently two steps ahead. You anticipate what is needed before it is asked and take pride in making complex days run smoothly.
• You enjoy working closely with leadership and know how to support planning so important meetings and events run smoothly.
• You can hold both the big picture and the smallest details at the same time—and nothing slips through the cracks.
• You exercise strong judgment. You know when to act, when to ask, and when to handle something quietly and with discretion.
• You are energized by a fast-paced environment where priorities shift and no two days are the same.
• You build trust quickly with a wide range of people and represent leadership with professionalism, warmth, and steadiness.
• You appreciate institutions with history and values, and you are equally motivated by helping them evolve and improve.
• You are comfortable with technology and curious about using new tools, including AI, to work more effectively.
• You bring a sense of calm, perspective, and even humor when things get complicated.

This is not a role for someone who prefers narrowly defined tasks or a predictable routine. It is for someone who wants to be deeply embedded in the life and leadership of a school and take real ownership of making it run well.

• Bachelor’s degree required
• Minimum of 5 years of executive-level administrative experience, ideally in a mission-driven organization
• Commitment to fostering a respectful, inclusive, and welcoming community
• Exceptional organizational, problem-solving, and project management skills
• Outstanding written and verbal communication skills
• High level of discretion, professionalism, and sound judgment
• Strong proficiency with Microsoft 365 and digital tools; experience with databases such as Veracross is a plus
• Demonstrated ability to use data and technology to improve workflows and decision-making
• Comfort adopting new tools, including AI-enabled platforms

The Environment

The Head’s Office is a place of high expectations, steady pace, and deep purpose. The work is relational, dynamic, and often complex. In return, it offers the opportunity to be part of something meaningful and to contribute in a way that is both visible and lasting.

Physical Requirements

• Ability to lift up to 10 pounds
• Ability to sit or stand for extended periods
• Ability to work in an office and school 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.

Work Authorization Policy

This role is contingent upon the Employee’s ability to lawfully work in the United States in a manner compatible with the structure, schedule, and duration of the position. Any employment authorization that requires institutional agreements, academic-credit participation, or third-party oversight is subject to the School’s review and written approval.