Executive Assistant to the Office of Head of School

Administrator / Full-Time

Walnut Hill School for the Arts, Natick, MA

$65,000.00 To 70,000.00 Annually

Walnut Hill School for the Arts seeks an accomplished Executive Assistant to the Office of the Head of School  to coordinate the affairs of the Head of School’s office and Board of Trustees for this global leader in arts education, one of only three independent arts high schools in the U.S. As a key member of the Head of School’s team, the Executive Assistant serves as a key link in ensuring seamless school operations and supporting the Head of School’s vision and activities.

The Walnut Hill School for the Arts Executive Assistant to the Office of the Head of School is an experienced office administrator with superior organizational and time-management skills. This position handles extensive event and travel planning and management for School events, and serves both as the primary administrative support for the Head of School, Board of Trustees, and the Senior Leadership Team.

This is a full-time, 12-month, position reporting directly to the Head of School. Certain events and meetings require availability during evenings and weekends.

All Walnut Hill faculty/staff are active and engaged members of the school community who are committed to collaborating and growing in their field, participating in school events and supporting students in their arts, supporting other faculty/staff members, and have the ability to self-reflect on their own practice.

Duties & Responsibilities

Head’s Office Responsibilities 

  • Manage the Head of School’s schedule, daily meetings, and conferences;
  • Provide extensive travel planning and management for Head of School and other administrators as needed; manage complex itineraries and support Head of School throughout travel;
  • Serve as the lead with the Head of School on monitoring Strategic Plan progress goals, managing task forces, and liaising with school personnel and Trustees assigned to Strategic Plan initiatives;
  • Act as a central liaison between Head of School and faculty, staff, parents, alumni, donors, and students;
  • Maintain professionalism and confidentiality befitting the office of the Head of School when dealing with all school constituencies, both internal and external;
  • Compose, edit, and disseminate all correspondence from the Office of the Head of School;
  • Provide support to the Head of School’s fundraising responsibilities by collaborating with the Development Office Plan and assist in organizing all major events including Awards Ceremony, Graduation, and employee appreciation events;
  • Track budget spending, generate monthly expense reports, assist in the Head’s Office budget management, and authorize expenditures for major events;
  • Draft and edit letters, Head’s Updates, thank-you notes, and other correspondence/communications on behalf of the Head of School;
  • Take and distribute minutes regularly for Leadership Team meetings and other meetings as requested;
  • Plan, execute, and attend Leadership Team retreats as requested; and
  • Other duties as assigned.

Secretary to the Board of Trustees

  • Schedule, plan, and coordinate all full Board meetings, Executive Committee meetings, and other Trustee committee meetings as requested;
  • Create agendas, compile and distribute materials; take Board minutes;
  • Assist with onboarding of newly elected Board members as directed by President of the Board of Trustees and Governance Committee Chair;
  • Cultivate and steward relationships with trustees on behalf of the Head of School’s office and the School;
  • Manage the online Trustee portal by updating documents, uploading meeting minutes, as well as serve as the primary troubleshooter for site issues;
  • Update all relevant Trustee membership documents such as annual conflict of interest forms, Board Handbook, and Trustee Contact Sheet; and
  • Steward and manage relationship with the President of the Board of Trustees and assist in their duties as needed.

Community Engagement

  • As a representative of the Head’s office, it is expected that the Executive Assistant to the Head of School will actively participate in the community by supporting the Student Life program. This may include chaperoning school events or other opportunities for community involvement that arise throughout the school year;
  • Collaborate, attend, and participate in all Professional Development days, training programs, orientation programs, benefit meetings, mandatory seminars, team-building exercises, and safety training/drills; and
  • Pursue professional development opportunities in and out of school; display willingness and ability to grow, learn, explore new approaches, and practice self-reflection.

Essential Skill Sets and Competencies:

  • Critical thinking skills and the ability to problem solve with poise;
  • Flexible work style with the ability to multi-task and respond to sudden needs as they arise;
  • Customer-Service driven work ethic;
  • Must be able to adhere to the highest standards of confidentiality;
  • Ability to make decisions independently and work collaboratively with a team;
  • Strong cultural sensitivity and the ability to have successful interactions within a highly diverse community;
  • Excellent communication skills, both verbal and written;
  • Superior organizational and time-management skills;
  • Strong writing and editing skills as well as ability to adapt Head of School’s writing-style;
  • Ability to foresee issues before they arise as well as have an innate sense of Head of School’s needs;
  • Unwavering patience under duress in a variety of working environments; and
  • Capacity to manage and navigate a wide array of personalities, while cultivating community support for Head’s initiatives.


  • Bachelor’s Degree or equivalent experience;
  • 3-5 years prior experience in a responsible Administrative position;
  • Proficient in the use of Microsoft Office Suite and Google Applications, and online portal management;
  • Ability to handle highly sensitive information with discretion and maintain confidentiality;
  • Experience in a non-profit or education setting preferred; interest in the arts a plus; and
  • Comfortable in a tech-heavy environment.

Physical Demands

Physical demands include dexterity for office machine and supply operation including but not limited to writing, typing, using electronic devices, computer, phone, calculator, copy machine, fax machine, and printers. Stooping, bending, traveling to/from locations on campus, ascending/descending stairs, reaching and sitting or standing for extended periods of time are common.

About us:

Walnut Hill School for the Arts, located in Natick, Massachusetts and 20 minutes from Boston, is an independent boarding and day high school offering a transformational educational experience designed for student artists in grades 9–post graduate. Walnut Hill combines a comprehensive college-preparatory academic curriculum with intensive, pre-professional artistic training in theatre, dance, music, visual art, and writing, film & media arts. Walnut Hill is committed to creating and enhancing an inclusive environment, and welcoming and celebrating a wide range of cultural, artistic, and educational backgrounds that compliments and supports our diverse community.

Commitment to the school’s Core Values, of Community, Growth, Excellence, Creativity, and Respect are imperative to the success of all Walnut Hill faculty, staff, and administration members. All Walnut Hill faculty/staff are active and engaged members of the school community who are committed to collaborating and growing in their field, participating in school events, supporting students in their arts, supporting other faculty/staff members, and who have the ability to self-reflect on their own practice. Adults at Walnut Hill participate in school events, support students in their arts, embrace the immersive, residential mission of the school, and support other employees in a warm and caring community of high expectations.

To Apply: Submit resume and cover letter through the Walnut Hill School for the Arts online Career Center.

Note: All offers of employment are contingent upon the successful completion of state and federal background checks. Walnut Hill does not provide visa sponsorship.

Walnut Hill School for the Arts

Natick, MA
High School, Post Graduate
Day, Boarding
All Gender