Office Manager and Executive Assistant - High School

Chesterton Academy of the Divine Family; Hagerstown (MD); On-site; Full time

Benefits offered by this job

401(k) matching

Paid time off

Daily Mass and spiritual enrichment

Joyful and mission-centered school culture

Professional development opportunities

Job summary

A Catholic classical high school is seeking an Office Manager & Executive Assistant to oversee daily operations and support school leadership. The ideal candidate should have strong organizational skills, attention to detail, and a welcoming presence. Key responsibilities include managing front office operations, coordinating events, and maintaining the school calendar. The position offers competitive compensation, opportunities for advancement, and a collaborative, faith-centered work environment.

Qualifications

• Previous experience in office management or school administration preferred.
• Ability to manage multiple priorities in a fast-paced environment.
• Professional, welcoming demeanor in line with the school’s mission.

Responsibilities

• Manage day-to-day front office operations efficiently.
• Coordinate logistics for major school events such as Open Houses.
• Develop and maintain the official school calendar and academic schedules.
• Provide administrative support for fundraising initiatives.
• Serve as the primary liaison with facility partners.

Skills

Organizational skills

Multitasking

Problem-solving skills

Interpersonal skills

Written communication

Verbal communication

Education

Bachelor’s degree preferred

Associate’s degree or relevant experience

Tools

Microsoft Office

Google Workspace

Job description

Benefits:

• 401(k) matching
• Competitive salary
• Dental insurance
• Health insurance
• Opportunity for advancement
• Paid time off
• Training & development
• Vision insurance

Benefits/Perks

• Daily Mass and spiritual enrichment as part of a faithful school community
• Joyful and mission-centered school culture
• Competitive compensation
• Professional development opportunities through the Chesterton Schools Network
• A unique opportunity to shape a growing school’s arts and drama program from the ground up

Overview

Chesterton Academy of The Divine Family, a joyfully Catholic, classical high school in the Chesterton Schools Network, is seeking a highly organized, proactive, and mission-driven Office Manager & Executive Assistant to oversee daily operations and support school leadership.

This role is essential to the smooth functioning of the school and serves as the primary point of contact for families, students, and visitors. The ideal candidate brings strong administrative skills, attention to detail, and a warm, welcoming presence that reflects the mission and culture of the school.

Primary Responsibilities

Daily Office Administration

• Manage day-to-day front office operations, ensuring efficiency and organization
• Serve as the first point of contact for all school inquiries and maintain positive parent and student relations
• Oversee student attendance, parking permits, carpools, and sick‑bay coordination
• Ensure school safety procedures are followed, including emergency drills and protocols
• Maintain and organize student records and school files (current and archived)
• Oversee front desk receptionists and coordinate volunteer support
• Manage office supplies, inventory, and classroom setup needs

Event Planning & School Activities

• Coordinate and oversee logistics for all major school events, including:
  • Open Houses
  • Parent-Teacher Conferences
  • Lenten Service Projects
  • Field trips and student activities
  • Standardized and placement testing (PSAT, CLT, Stanford, etc.)
  • Special events such as vocation talks, chaplain visits, and community gatherings
• Ensure volunteers are recruited, trained, and scheduled appropriately for events

Calendar & Scheduling

• Develop and maintain the official school calendar, including academic schedules and events
• Coordinate daily schedules and room usage
• Assign substitute coverage for faculty absences
• Track faculty PTO, sick time, and attendance
• Ensure smooth coordination of all school activities and scheduling needs

Fundraising & Administrative Support

• Provide administrative support for fundraising and marketing initiatives, especially the annual Gala
• Assist with communications, donor coordination, and event logistics as needed

Facilities & External Coordination

• Serve as the primary liaison between the school and facility partners
• Coordinate space usage, scheduling, and operational needs with external partners
• Collaborate with district nurse and external service providers as needed

Qualifications

• Bachelor’s degree preferred; Associate’s degree or relevant administrative experience required
• Previous experience in office management, executive assistance, or school administration preferred
• Strong organizational, multitasking, and problem‑solving skills
• Excellent written and verbal communication skills
• Proficiency in Microsoft Office and Google Workspace
• Ability to manage multiple priorities in a fast‑paced environment
• Professional, welcoming demeanor with strong interpersonal skills
• Commitment to supporting a mission‑driven Catholic school environment

Benefits / Perks

• Competitive compensation
• Paid time off and holidays
• Career growth opportunities within a growing school
• Daily Mass and spiritual enrichment
• Joyful, faith‑filled, and collaborative work environment

About Chesterton Academy of The Divine Family

Opening in Fall 2025, Chesterton Academy of The Divine Family is part of the Chesterton Schools Network. We offer a rigorous, integrated classical high school education rooted in the Incarnation of Jesus Christ. Our mission is to form joyful leaders and saints through faith, reason, and virtue in partnership with families.