Executive Assistant to Head’s Office

Executive Assistant

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.

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

• 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:

• 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:

• 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:

• 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:

• 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:

• 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:

• 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.

Requirements:

• 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…