Executive Assistant to the Head of School

The Kiski School has engaged DovetailED to lead a search for a Executive Assistant to the Head of School to start immediately. Interested candidates should review the Opportunity Statement and submit a cover letter, resume, and list of references as a consolidated PDF to Ashlyn Chillemi, Senior Recruiter at DovetailED Talent Sourcing, at ashlyn@dovetailedsourcing.com.

Founded in 1888, The Kiski School is an independent, college-preparatory, co-educational, boarding and day school serving students in grades 9-12 and post-graduate year, located on a 300-acre campus in Saltsburg, Pennsylvania, 30 miles east of Pittsburgh. Kiski is home to a close-knit community of roughly 200 students and is known for its rigorous academics and strong record of college placement. The school offers a warm, collaborative work environment grounded in tradition and a shared commitment to the growth of every student. All Kiski employees are committed to living out the school's mission of preparing students for success in college and life.

Position Summary The Executive Assistant to the Head of School provides high-level administrative and organizational support to the Head of School and plays a central role in the daily operations of the Heads Office. This individual serves as a trusted partner to the Head, manages complex scheduling and logistics, coordinates events, and provides support across the senior leadership team. The ideal candidate is highly organized, discreet, an excellent communicator who is comfortable operating in a fast-paced environment where priorities shift and confidentiality is paramount.

Key Responsibilities

Calendar & Schedule Management

Manage and maintain the Head of Schools calendar, proactively resolving scheduling conflicts and prioritizing competing demands Coordinate appointments, meetings, and commitments involving trustees, senior staff, parents, alumni, and external partners Anticipate the Heads scheduling needs and prepare materials in advance of meetings

Event Management & Logistics

Plan and coordinate logistics for events hosted by or involving the Head of School, including on-campus gatherings, meetings, and school functions Coordinate travel arrangements, itineraries, and related logistics Manage vendor and venue coordination as needed for events tied to the Heads Office

Communications & Correspondence

Draft, proofread, and manage correspondence on behalf of the Head of School with a high level of accuracy and professionalism Serve as a point of contact for the Heads Office, exercising sound judgment in triaging inquiries and requests Prepare briefing materials, agendas, and follow-up documentation for meetings

Senior Staff Support

Provide administrative and logistical support to members of the senior leadership team as needed Assist with coordination across departments to ensure alignment with the Heads priorities and school-wide initiatives

Confidentiality & Discretion

Handle sensitive information regarding students, families, faculty, and school operations with the utmost discretion Exercise sound judgment in matters involving confidential school, personnel, or board-related information

Qualifications

Bachelors degree required Prior experience as an executive assistant or office manager strongly preferred Superior attention to detail and strong organizational skills Ability to read, write, and communicate at a high level Demonstrated ability to handle confidential and sensitive matters with extreme discretion Strong interpersonal skills, with the ability to build trust and rapport across a diverse school community Ability to manage multiple priorities in a dynamic, deadline-driven environment Proficiency with standard office and scheduling software

Work Environment This is a full-time, year-round, on-campus position based at The Kiski School in Saltsburg, PA. The role may occasionally require flexibility outside standard business hours to support school events or the Head of Schools schedule.