Executive Assistant to the Associate Head of School and CFOO

Westover School - Middlebury, CT

Full-time - Mid Level

Middlebury, CT

Educational Services

About the position

Westover School is seeking a responsible, dependable, and detail-oriented Executive Assistant to support the Associate Head of School and the Chief Financial & Operations Officer (CFOO). This full-time position is integral to the smooth operation of the school, which is dedicated to empowering young women through a college preparatory education in a supportive community. The Executive Assistant will play a crucial role in managing schedules, organizing events, and facilitating communication between various departments and stakeholders. The ideal candidate will possess superior organizational and time-management skills, along with a strong commitment to confidentiality and professionalism. In this role, the Executive Assistant will dedicate approximately 50% of their time to assisting the Associate Head of School, 40% to coordinating maintenance tasks, and 10% to supporting the CFOO. Responsibilities include managing the schedules of both the Associate Head of School and CFOO, acting as a liaison between the maintenance department and the Mojo Facilities Request system, and maintaining professionalism in all communications. The Executive Assistant will also assist in the hiring and onboarding processes for junior-level staff, compose and disseminate correspondence, and collaborate with other administrative staff to organize significant school events such as Convocation, Award Ceremonies, and Graduation. The position requires active participation in the school community, including attending professional development days and training programs. The Executive Assistant will be expected to engage in ongoing professional development and demonstrate a willingness to learn and adapt. Critical thinking, problem-solving skills, and a customer-service driven work ethic are essential for success in this role. The Executive Assistant will also need to navigate a variety of personalities and foster community support for initiatives led by the Associate Head of School and CFOO.

Responsibilities

• Manage the schedules of the Associate Head of School and CFOO, including daily meetings and conferences.
• Act as a central liaison between the Mojo Facilities Request system and the Maintenance Department.
• Maintain professionalism and confidentiality when dealing with all school constituencies.
• Support the Associate Head of School in building awareness and education in developing equity at systemic levels.
• Assist with the hiring and onboarding process for junior-level administrators, faculty, and staff positions.
• Compose, edit, and disseminate organizational correspondence from the Associate Head of School.
• Collaborate with the Executive Assistant to the Head of School and Registrar to organize significant events.
• Track budget spending, generate monthly expense reports, and assist in budget management for the Associate Head and CFOO.
• Support strategic partnerships to implement findings and productive change to Westover's mission.
• Participate in community engagement activities and professional development opportunities.

Requirements

• Bachelor's Degree or equivalent experience.
• 3-5 years prior experience in a responsible Administrative position.
• Proficient in Microsoft Office Suite and Google Applications.
• Experience or interest in diversity, equity, and inclusion initiatives.
• Ability to handle highly sensitive information with discretion and maintain confidentiality.
• Experience in a non-profit or education setting preferred.
• Comfortable in a tech-heavy environment.

Nice-to-haves

• Experience in event planning and management.
• Strong communication skills, both verbal and written.
• Ability to foresee issues before they arise and understand the needs of the Associate Head of School.