Executive Assistant to the Head of School and Board Liaison

St. Andrew's School develops the independence, character, mind, and spirit of its students to prepare them for lives of citizenship, service, and purpose. Be at the center of this mission by joining the school as our executive assistant to the head of school and board liaison, a key member of the office of the head of school.  

Position Summary:  

The Head of School’s Office at St. Andrew’s sets all institutional priorities. Every part of the school runs through it — academics, student life, advancement, admissions, finance, facilities, the Board of Trustees, alumni, and families. The executive assistant works at that intersection, facilitating decision-making and leadership priorities that shape the experience of every student, employee, and stakeholder.

The role has two primary portfolios. The first is running the office: directing the Head of School's time toward priorities, making sure she is prepared for travel, meetings, and engagements, and owning the board cycle end to end — board correspondence, event logistics, governance material prep, and day-of execution are principal responsibilities of the executive assistant.

The second half is operational excellence. The executive assistant has the latitude to shape the office’s processes, tools, and workflows and the judgment to improve them, continuously developing a stronger foundation of operational best practices. Building on early AI work, the executive assistant will also explore and identify promising new applications and use cases that will benefit the Office and the school’s broader administrative support teams. 

St. Andrew’s seeks an experienced, fast, and precise teammate who meets volume with steadiness and optimism, who is authentic and equally at ease with trustees, faculty, families, and students, and who is curious about how a complex institution works from the inside out. A strong candidate for this role seeks out feedback, brings potential solutions along with problems, and builds each lesson learned into how the work gets done.

The executive assistant reports to the director of head of school’s office, who holds decision-making authority for the operations of the office and reports to the Head of School. The executive assistant works with the Head of School and the director of head of school’s office daily and is expected to learn the office’s priorities and operating rhythm well enough to act on them independently. This individual will also have a keen instinct to communicate with stakeholders proactively to advance the Office’s priorities. The executive assistant and the director of head of school’s office will also cross-train with administrative staff across the school to ensure continuous coverage in the case of absences.

Essential Duties and Responsibilities:

Office of the Head of School

• Manages the Head of School's calendar, prioritizing her time against the school’s institutional priorities.

• Prepares the Head of School for meetings, engagements, and public events, providing briefing materials, background, and context in advance.

• Monitors correspondence for the Head of School—all inbound requests for her time and attention—to ensure all items are triaged appropriately and items requiring her attention are prioritized.

• Drafts, copy-edits, and proofreads correspondence and communications on behalf of the Head of School for internal and external audiences.

• Reception: serves as the first point of contact to the Office of the Head of School for faculty, staff, students, families, trustees, alumni, and visitors, and receives the Head of School’s guests so that each is expected, welcomed, and prepared for the meeting; this extends to pre-arrival preparations for overnight guests at the Head of School’s home (House 1) as well.

• Plans the Head of School’s travel and builds itineraries in coordination with the Advancement team, including all accommodations and logistics.

• Supports the Head of School’s spouse in School engagements that call for both, coordinating calendars, correspondence, and expense reimbursement.

• Supports planning for the Head of School's presence in the life of the school: visits to classes, meals, and games, and meetings with student, faculty, and parent groups.

• Plans and manages events hosted by the Head of School, including those at House 1, from invitations and guest lists through catering, facilities work orders, and day-of execution.

• Works with the Communications Office on the drafting, timing, and distribution of communications from the Office of the Head of School.

• Manages the School's relationships with external educational and membership associations, including scheduling, correspondence, dues, and payments.

• Arranges meals for the Head of School and her school guests when the dining hall is closed, including during breaks and other times when students are away from campus.

• Keeps the office stocked, equipped, and ready for visitors, managing supplies and purchasing within the office budget.

• Manages monthly reconciliation of the Head of School’s Office expense reports and reimbursements.

Board Operations

• Manages the operating cycle of the board year, including meeting and committee scheduling, deliverable tracking, and the production calendar.

• Produces board and committee materials, from intake through proofing, assembly, and publication with “zero-defect” work habits and expectations.

• Serves as lead administrator of the school’s board portal: publishes materials, maintains the directory, archives board documents, and orients trustees to the platform and resolves their issues with it.

• Drafts minutes for meetings of the full Board and select committee meetings as required.

• Manages logistics for Trustee Weekends and off-cycle committee meetings, including scheduling, invitations and responses, room reservations, facilities work orders, travel, hospitality, and trustee gifts.

• Administers the annual end-of-year board survey for the Chair of the Trusteeship Committee.

• Maintains mastery of the bylaws and board compliance, and keeps the Board's policies and permanent records of its proceedings.

• Prepares onboarding schedules for incoming trustees, and maintains trustee records, including terms of service, committee assignments, biographies, and contact information, in Raiser's Edge.

• Serves as the single point of contact for the Board and Trustees Emeritus on materials, scheduling, logistics, and requests to the office.

Institutional Priorities and Cross-Functional Coordination

• Tracks commitments made in the Head of School's meetings and follows them through to completion across departments.

• Supports the Core Team's operating rhythm, including: preparation and follow-through for weekly meetings and the monthly initiative review; coordination of work that crosses departmental lines, breaking bottlenecks and ensuring milestones and deliverable deadlines are met.

• Represents the Office of the Head of School in working groups and project teams as the school’s priorities require.

• Coordinates searches for the Head of School's direct reports with Human Resources, search committees, and search firms.

• Coordinates annual 360-degree feedback for the Head of School's direct reports.

• Coordinates the faculty contract cycle with Human Resources and the Dean of Faculty if needed.

Systems, Tools, and Continuous Improvement

• Owns the tools and workflows of the office and improves them continuously.

• Applies the School's automation and AI tooling to raise the quality, speed, and consistency of the office's work, and proposes new tools as needs and use cases emerge.

• Documents systems and processes so that they can be maintained, transferred, and built on.

• Sets standards for administrative practice across the school, including correspondence conventions, document standards, and scheduling norms, and brings what works in this office to colleagues elsewhere.

• Over time, serves as an informal lead for administrative assistants across the school, building a shared culture and a consistent approach to executive support.

• Develops and maintains cross-training with administrative colleagues, in collaboration with the director of head of school’s office, so that coverage during absences is planned in advance.

• Attends professional development workshops and conferences like SAIS and ADVIS to learn and incorporate best practices from other administrative support professionals and experts.

• Manages the daily operations and budget of the Office of the Head of School.

Community, Discretion, and Professionalism

• Represents the Office of the Head of School professionally to every constituency in the school and beyond it.

• Handles confidential information about students, families, personnel, and trustees with discretion and sound judgment.

• Participates in the life of a residential school, including major school events and Trustee Weekends.

• Adheres to the school’s established dress code while classes are in session.

Job Requirements:

• High school diploma required; bachelor’s degree preferred.

• Minimum of four years of experience with at least two in executive operations, board or governance support, or a comparable role supporting senior leadership.

• A record of managing high volume across competing deadlines accurately, and of setting clear priorities when demands compete.

• A record of steadily improving how their work gets done.

• The judgment to know when to ask, when to push back, and when to decide, and the willingness to do each when necessary.

• Demonstrated judgment in handling confidential information.

• Sound judgment during the Head of School's absences: resolving what can be resolved and referring what should be referred.

• Strong writing, with exceptional proofreading and copy-editing skills.

• Excellent problem-solving skills, confidence when navigating ambiguity, and a growth mindset.

• Proficiency with Google Workspace and Microsoft Office, and the ability to learn new systems quickly.

• Genuine interest in new tools, including AI-enabled tools, and initiative in applying them to real problems.

• Availability for the schedule of a residential school, including some evenings, weekends, major school events, and Trustee Weekends during the school year.

• Excellent references regarding effectiveness, professionalism, and discretion.

• Genuine interest or passion for learning, institutions of learning, and the process of human formation, and a desire to do purposeful work in service of young people.

Preferred Qualifications:

• Experience in one or more of the following professional environments: independent school, higher education, government, mission-driven organization with a governing board, corporate C-suite support, management consulting.

• Experience supporting a board of trustees or directors.

• Experience building a process, tool, or system that outlasted their involvement in it.

• Experience coaching administrative colleagues or setting shared standards of practice.

• Familiarity with board management platforms, project management tools, or workflow automation.

• Facility with database management, reporting, and analysis, including Raiser's Edge or a comparable CRM. 

• Intermediate to advanced level skill with agentic tools (e.g., Claude, ChatGPT, Gemini) and their application in administrative workflows and operations.

Conditions of Hire: 

A thorough background check—inclusive of fingerprinting, a Child Protection Registry Check, a motor vehicle record check, and a background check is required as a condition of employment. 

Applicants must complete satisfactory reference checks, confirmation of compliance with federal and state employment laws, and any other required conditions of employment.

Benefits of Employment at St. Andrew’s School:

• Benefits are subject to eligibility requirements and plan guidelines; additional details can be found in our employee handbook, which is furnished upon request.

• Medical, Dental, and Vision Insurance: Two health plan options to ensure you and your family have access to quality care.

• Retirement Plan: Secure your financial future with our 403(b) and Roth retirement plans. 2-for-1 employer match up to 5% of salary (up to 10% from the School). All contributions are subject to annual IRS limits. Immediate eligibility for employees working half-time or more.

• Paid Time Off: Generous paid time off and holidays to help you maintain a healthy work-life balance.

• Employee Assistance Program: Access to resources and programs promoting physical and mental well-being.

• Health Savings Account, which includes a St. Andrew’s School match.

• Life and AD&D Insurance at no cost to you.