Assistant to the Head of School

Choate is currently hiring for the dynamic role of The Assistant to the Head of School. The Assistant to the Head of School is a trusted, high-impact professional working directly with the Head of School at the center of Choate's daily operations and leadership activity. The Assistant manages organizational, logistical, and communication responsibilities while exercising significant judgment and discretion in a fast-paced environment that requires intellectual agility and an ability to navigate institutional dynamics. The role offers close exposure to senior leadership, school priorities, and the realities of leading a large educational organization.

The Assistant works where information, people, and priorities converge, helping ensure that the Head of School is well prepared, well informed, and able to focus on the most consequential aspects of leadership. The position requires clarity, care, initiative, and the ability to manage competing demands effectively.

This role goes beyond routine administrative duties. It is an intellectually demanding, fast-paced position for someone who learns quickly, anticipates needs, and takes responsibility for executing work at a very high standard. The role is well suited to either an outstanding early-career candidate with a strong academic background and demonstrated maturity, or a more experienced professional who is excellent at this kind of work and intentionally seeks close proximity to senior leadership.

The School is committed to professional development, and this position offers unusually strong preparation for future work in areas such as admission, advancement, communications, academic administration, teaching, or other leadership pathways within independent schools.

This is a full-time, exempt position. Because the role provides direct executive support, regular in-office presence concurrent with the Executive's schedule, which can extend beyond the typical hours above is essential. Compensation is competitive and includes excellent benefits.

While this position reports to the Chief of Staff, the majority of the day-to-day direction comes from the Head of School.

Key Responsibilities include:

• Manage the Head of School's time, information flow, and daily priorities with judgment, discretion, and attention to detail, including calendar management and scheduling.

• Ensure the Head of School is well prepared for meetings, events, and engagements by organizing materials, briefing documents, and follow-up actions.

• Provide administrative and logistical support for meetings, school events, and leadership engagements, including coordination, preparation of materials, scheduling, and follow-up support.

• Arrange complex travel and prepare detailed itineraries that anticipate needs and minimize friction.

• Draft, edit, and manage correspondence on behalf of the Head of School, including sensitive and high-level communications.

• Serve as a primary point of contact between the Head of School and internal and external constituencies, ensuring communication is timely, thoughtful, and appropriately handled.

• Support personal and household logistics for the Head of School with efficiency, discretion, and strong attention to detail.

• Maintain an organized, forward-looking office environment by anticipating needs and proactively resolving issues before they arise.

• Handle confidential and sensitive information with the highest level of professionalism at all times.

• Strong academic background with evidence of intellectual rigor, clear thinking, and sound judgment.

• Exceptional organizational, writing, and interpersonal skills.

• Demonstrated ability to manage multiple priorities accurately and calmly in a dynamic environment.

• High level of discretion, professionalism, and maturity.

• Ability to learn quickly, take initiative, and work effectively with limited direction.

• Comfort working closely with senior leadership and interacting thoughtfully and professionally with a wide range of constituencies.

• Prior administrative or related professional experience is welcome but not required; demonstrated capability and readiness for responsibility matter more than tenure.

• High level of comfort with Apple hardware and software ecosystems, Microsoft Office products, and other common professional technology platforms.

• Ability to use AI tools such as ChatGPT and related technologies in a discerning, informed, and ethical manner consistent with Choate's Stance on AI.

• Valid driver's license and willingness to drive an electric vehicle as needed.