Executive Assistant to the Head of School

Job Title: Executive Assistant to the Head of School

Position Overview: The Executive Assistant to the Head of School plays a critical role in ensuring the smooth and efficient operation of the Head of School's office. This highly collaborative position requires an individual who is trustworthy, organized, and adaptable to meet the dynamic needs of a busy educational environment. The Executive Assistant to the Head of School will work closely with the Head, administrators, faculty, staff, and the Board of Trustees to support the mission and daily operations of the school while maintaining a high level of confidentiality, professionalism, and attention to detail.

Key Responsibilities:

• Administrative Support: Provide high-level administrative support to the Head of School, including calendar management, scheduling meetings, answering phone calls professionally with appropriate, timely follow-up. Manage correspondence, coordinate all travel arrangements, and reconcile credit card statements with receipts. 
• Communication Management: Serve as a primary point of contact for internal and external stakeholders, including staff, faculty, parents, alumni, and Board members. Draft and manage correspondence, communications, and reports on behalf of the Head of School. Keep in close contact with Advancement to be able to prepare and print personal thank you letters from the Head of School in a timely manner to acknowledge meaningful gifts to Canterbury.  
• Collaboration with Administrators: Work closely with the school leadership team, assisting with special projects, meetings, and initiatives that support the overall objectives of the school.
• Board of Trustees Coordination: Assist with scheduling Board meetings, preparing materials for meetings, and ensuring smooth communication between the Head of School and Board members. Transcribe and prepare Board Meeting minutes. Ensure that all documentation and materials are organized and delivered in a timely manner.
• Collaboration with Resident Chaplain: prepare and mail Mass cards to members of the community when requested. Order supplies for the chapel, assist with office work and communication required for Confirmation and Baptisms with students, parents, our local parish and the Archdiocese.   
• Collaboration with Departments: work closely with a wide range of employees at the school. In particular, work closely with Maintenance, Dining, Advancement, Housekeeping and Grounds to ensure successful execution of campus needs, events and activities.
• Event Coordination: Assist in organizing events such as Trustee Weekend - three times per school year- (Board meetings and dinners) Administrative Retreat(s), school gatherings and celebrations for faculty and staff during the year. Ensure seamless execution and smooth communication among all participants.
• Update Databases: for NEASC, CAIS, TABS, NAIS etc. 
• Commencement responsibilities: Work closely with the Admin Assistant in Academics who runs Commencement. Ordering custom Commencement Medals (communicate with parents and vendor), Correspondence to International families to help assist with VISA application for travel. Work with College(s) (Book Awards) throughout the school year for the delivery of awards for the underform Awards Ceremony in the spring.
• Confidentiality & Discretion: Maintain the highest level of confidentiality when handling sensitive information, leadership team discussions, printing and distributing of faculty contracts.  Above all, respecting the privacy of students, families, faculty, staff and Board members. 
• Student, Parent, and Alumni Engagement: Foster positive relationships with the school community by engaging with students, parents, and alumni in a professional and welcoming manner. Demonstrate a keen interest in the school's values and objectives, creating an environment of trust and respect.
• Problem Solving & Support: Anticipate needs and be proactive in addressing issues or tasks before they arise. Adapt quickly to changing circumstances and take initiative when necessary.
• General Office Support: Ensure that the office of the Head of School is organized and well-maintained, facilitating a productive and positive work environment. Communicate effectively with other offices and administrative assistants at the school during periods of busy administrative activity and offer help when needed. Provide input on improving efficiencies and policies on an ongoing basis.  

Qualifications:

• Experience: Minimum of 3-5 years of experience as an Executive Assistant, Administrative Assistant, or in a similar support role, preferably in an educational or nonprofit environment.
• Skills: Strong organizational, communication, and interpersonal skills. Proficiency in Microsoft Office Suite (Word, Excel, PowerPoint), Google Suite, and familiarity with school management systems (Veracross) and (Raiser’s Edge) Excellent proofreading and writing skills. 
• Trustworthiness & Integrity: Must exhibit high levels of discretion, professionalism, and confidentiality. A commitment to maintaining the trust of the Head of School, Board members, faculty, staff, students, and families is essential.
• Interpersonal Skills: Ability to build and maintain positive relationships with diverse groups, including students, parents, alumni, faculty, and Trustees.
• Sense of Humor & Empathy: A positive attitude, sense of humor, and ability to manage stressful situations with grace. Must be able to maintain calm under pressure and demonstrate empathy and care in all interactions.
• Interest in Education: A deep interest in the mission and values of the school, as well as a genuine commitment to the welfare and success of students, parents, and the broader school community.
• Education: Four year bachelor’s degree preferred.

Personal Attributes:

• Efficient & Detail-Oriented: Ability to juggle multiple tasks and deadlines with attention to detail and accuracy.
• Self-Motivated & Independent: A proactive self-starter who is capable of working with minimal supervision, yet thrives in a collaborative environment.
• Confidential & Professional: Discretion and the ability to handle sensitive information with the utmost care and professionalism.
• Positive Attitude & Adaptability: A flexible and can-do attitude, willing to take on new challenges as they arise.

Compensation and Benefits:

This is a full-time, benefits eligible position. Compensation commensurate with experience.  

To Apply: 

Please submit your resume and a cover letter detailing your experience and interest in the position to Allyson McFerren Mard, Director of Human Resources, at [email protected] . We look forward to learning more about how your skills and experience align with the values of our school community.