Executive Assistant to Head of School

Role Title: Executive Assistant to Head of School

FLSA Status: Full-Time Non-Exempt

Reports to: Head of School; Dotted Line to Manager Front Office Operations

Direct Reports: N/A

Main Purpose of the Role

The Executive Assistant to the Head of School is a highly skilled administrative and operational partner who ensures the effectiveness of the Head of School and the Board of Trustees. This role requires exceptional organizational judgment, technical fluency, and the ability to manage multiple priorities and projects simultaneously with discretion and independence.

In addition to serving as the primary liaison to the Board and steward of the Head’s office, this role also provides operational support to the Front Office as needed, contributing to the smooth daily functioning of the School.

Executive Support to Head of School:

• Own and strategically manage the Head of School’s complex calendar, including long-range planning and daily prioritization; evaluate and triage meeting requests, aligning scheduling decisions with institutional priorities.
• Anticipate needs, resolve conflicts proactively, and ensure the Head is fully prepared for all engagements.
• Coordinate logistics for internal and external meetings, including agendas, materials, and follow-up.
• Event planning and support, e.g., graduation, faculty and staff events, board meetings, dinners, parties, and retreats as needed.
• Other projects and tasks as directed by the Head of School.

Board Relations & Governance:

• Lead all operational aspects of the Board of Trustees, including coordinating schedules, booking travel arrangements, building presentations, reserving meeting spaces, etc.
• Prepare, compile, and distribute board materials using digital platforms (e.g., board portals such as Blackbaud or similar systems).
• Maintain and manage Board and committee portals, ensuring accuracy, organization, and accessibility of materials.
• Prepare, and maintain official meeting minutes and governance documentation.
• Manage trustee communications, onboarding, and orientation processes.
• Ensure alignment with governance best practices, timelines, and documentation standards.

Project & Workflow Management:

• Independently manage multiple concurrent projects on behalf of the Head of School, from planning through execution.
• Build and maintain systems to track workflows, deadlines, and cross-functional coordination.
• Identify opportunities to improve operational efficiency and implement streamlined processes.
• Take initiative to move work forward with minimal direction.

Technology & Systems Management:

• Demonstrate advanced proficiency in Google Workspace (Calendar, Gmail, Docs, Sheets, Slides, Drive), including shared drives, permissions, and workflow optimization.
• Manage and optimize use of Blackbaud systems (including Board portal and student information systems).
• Utilize project management tools (e.g., Asana, Trello, Monday.com, or similar) as required.
• Leverage scheduling and communication tools (e.g., Calendly, Slack) to improve efficiency.
• Maintain organized digital filing systems; ensure accessibility and version control of key documents.
• Troubleshoot and improve workflows across platforms.

Operations Support Responsibilities:

• Serve as backup support for the Front Office Operations Manager as needed.
• Provide front-facing support, including greeting visitors, answering phones, and assisting students and families.
• Maintain operational systems, including attendance tracking and student records within Blackbaud.
• Coordinate vendors and logistics for school operations (e.g., lunch program, photographers, facilities use).
• Support Leadership Team, Admissions, and Development with events and administrative needs.

Diversity, Equity, Inclusion, Justice, and Belonging Commitments:

• Engage in conversations with empathy and curiosity.
• Listen to recognize the presence, ideas, and beliefs of all individuals within the Cathedral School community.
• Practice courage and act with integrity to speak up and speak out to stand up for what is right even when it is challenging or unpopular.
• Uphold the process of reflection, healing, and repair, holding ourselves accountable and accepting responsibility for our actions.

Skills and Competencies:

• Exceptional interpersonal skills with a desire to serve others.
• Strong oral and written communication skills; ability to communicate in a …