The Country School is an independent, coeducational, PK-8 school founded in 1934 with approximately 300 students. Located on Maryland’s Eastern Shore, a few blocks from downtown historic Easton, we offer a challenging academic program in a nurturing environment focused on educating the whole child.

The Country School seeks a passionate, dedicated Executive Assistant & Office Manager for the 2026-2027 school year. This position works closely with the Head of School and Administrative Team to communicate effectively with parents, faculty and staff, the Board of Trustees, and all community constituents and facilitate the professional and positive environment of our school. Start Date is July 1, 2026.

Key Responsibilities

Administrative & Leadership Support

• Support the Head of School in all aspects of school operations and strategic initiatives
• Manage the Head of School’s calendar and scheduling, coordinating meetings and communications with parents, community leaders, Board of Trustees and committee members, donors, school administrators, faculty, and staff
• Provide organizational and operational support to Administrators and Division Heads
• Supervise the School Nurse and Receptionist

• Facilitate communication for the Board of Trustees
• Organize meetings, prepare materials, and record accurate meeting minutes

Calendar & Communications Management

• Manage and maintain internal & external school calendars (website, TCS app, Google, Veracross)
• Create, curate, and distribute the school-wide weekly newsletter by gathering updates and content
• Communicate schedules, updates, and events to faculty and staff
• Communicate weather and emergency alerts
• Update weekly digital signage across school platforms

Operations & Student Support

• Assist RN with medication administration by completing and maintaining Certified Med Tech training
• Supervise limited student duties (e.g., lunch, recess, carpool) as needed
• Provide front desk coverage when the Receptionist is absent

Athletics & Field Trip Coordination

• Coordinate transportation logistics for field trips and athletic events
• Organize permission slips and ensure compliance with school policies
• Support parent communication for athletics programs

The Country School Diversity Statement

The Country School believes that seeking and valuing diversity of ideas, experiences, and identities, developing meaningful connections, and fostering a sense of belonging are vital to each student’s education and growth. A diverse, inclusive, and equitable school community is critical for preparing students for a role in a complex, pluralistic, and interconnected society. We actively see and value the differences of our school community, among them ability/disability, age, ethnicity, faith traditions, family composition, gender identity and expression, learning styles, race, sexuality, and socio-economic status.

Equal Opportunity Employer

The Country School is an equal opportunity employer that does not discriminate on the basis of race, color, religion, age, sexual orientation, gender, nationality, or ethnic origin.

Education & Qualifications 

• Bachelor’s degree or commensurate work experience required
• 3+ years of experience working in an organizational, team-focused setting with specialty in communication skills and platforms.
  Experience with non-profits or schools is a plus
• Strong organizational and multitasking skills
• Excellent written and verbal communication abilities
• Proficiency with scheduling tools and systems (e.g., Google Workspace, Veracross preferred)
• Ability to collaborate across teams and maintain confidentiality
• Experience in administrative, operations, or school environments preferred

Qualified applicants should submit a cover letter and resume to:

Jay Parker, Head of School

resumes@countryschool.org