Executive Assistant to the Head’s Office

The Overlake School•Redmond, WA

23h•Onsite

About The Position

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.

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 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
Ability to lift up to 10 pounds
Ability to sit or stand for extended periods
Ability to work in an office and school environment
Ability to lawfully work in the United States

Nice To Haves

experience with databases such as Veracross is a plus

Responsibilities

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.
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.
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.
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.
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.
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.

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