Executive Assistant to Head of School

SUMMARY

Gann Academy seeks an experienced, highly professional, and mission-aligned Executive Assistant to the Head of School to provide high-level administrative support and help ensure the smooth, effective functioning of the Head of School Office.

This individual will play a critical role in supporting the school’s leadership and governance and will work closely with senior administrators, the Board of Trustees, and key partners across the community. A high degree of collaboration, discretion, responsiveness, and care for relationships is essential in an ideal candidate.

ESSENTIAL FUNCTIONS

• Represent the Office of the Head of School with professional, high-quality, verbal and written communications with faculty, staff, parents, students, and external organizations.
• Proactively manage the Head of School’s calendar, appointments, purchasing, expense reporting, and travel arrangements, including prioritizing requests, flagging conflicts, and ensuring appropriate prep time.
• Manage all appointment scheduling and travel arrangements for the Head of School and other Senior Leadership Team members.
• Support the Senior Leadership Team by scheduling meetings, retreats, and other events. Assist in collecting agendas for key 1:1 meetings for the Head of School and track key action items from meetings to support timely follow-through.
• Prepare and/or edit correspondence, reports, presentations, and other documents for the Head of School, including briefing materials and talking points for key meetings and events.
• Organize and coordinate guest visits.
• Handle incoming communications, including phone calls and emails, and prioritize responses.
• Serve as the liaison to the Board of Trustees, supporting the Board Chair; coordinate meetings; disseminate agendas and materials (internally and via the school portal); prepare and distribute minutes; and maintain Board records and documentation.
• Support Board committees as needed.
• Provide support for school events, including logistics, planning, and day-of-event coverage
• Perform additional administrative tasks as needed, including occasional front desk coverage.
• Attend weekend and evening events as needed, including Board of Trustees meetings, Back to School Night, and graduation, in support of the Head of School.

EMPLOYEE BENEFITS

• Competitive salaries
• Professional development
• Comprehensive benefits package featuring generous paid time off policies -including sick time, paid vacation, personal days, and U.S. holidays, Gann employees get up to an additional 15 days off for Jewish Holidays, depending on the Jewish Calendar of the year
• Short Fridays
• Comprehensive Health Insurance
• Retirement Plan Match (403B) starting immediately!
• Hungry? Gann has a full-service kosher dairy dining hall, complete with a fresh salad bar and multiple hot meal options
• Free parking!
• Fitness facilities for our faculty and staff
• Life Insurance
• Long-term Disability (LTD)
• MA PFML

WORKING CONDITIONS/PHYSICAL DEMANDS

Physical demands include dexterity for office machine/supply operations, including but not limited to computers, telephones, electronic calculators, copy machines, and printers. Stooping, bending, reaching for files or supplies, and sitting or standing for extended periods are common.

EQUAL EMPLOYMENT OPPORTUNITY

Gann Academy is an equal opportunity employer. It is the policy of the school to prohibit discrimination and harassment of any type and to afford equal employment opportunities to employees and applicants, without regard to race, creed, color, religion, national origin, sex (including sexual orientation, gender identity or expression), pregnancy, age, physical or mental disability, genetic information, or veteran status.

ACCOMMODATION

External and internal applicants, as well as position incumbents who become disabled as defined under the Americans with Disabilities Act, must be able to perform the essential job functions (as listed) either unaided or with a reasonable accommodation, as determined on a case-by-case basis by management.

E-VERIFY

This employer participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. If E-Verify cannot confirm that you are authorized to work, this employer is required to give you written instructions and an opportunity to contact Department of Homeland Security (DHS) or Social Security Administration (SSA) so you can begin to resolve the issue before the employer can take any action against you, including terminating your employment. Employers can only use E-Verify once you have accepted a job offer and completed Form I-9.

• A Bachelors degree is preferred
• Minimum of 3 to 5 years of experience in an executive assistant or similar administrative role
• Prior experience in an educational or nonprofit setting is preferred
• Strong organizational and time management skills with exceptional attention to detail
• Excellent verbal and written communication skills
• Proficiency in Microsoft Office Suite, Google Workspace, and other administrative tools
• Emerging understanding of the role of Artificial Intelligence in the workplace and willingness to be trained in its use
• Ability to handle sensitive and confidential matters with discretion and professionalism
• Flexibility and adaptability to handle a dynamic work environment
• Strong interpersonal skills with the ability to build positive relationships across all school constituencies