Office Manager and Executive Assistant - High School
Full Time • Hagerstown
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.
Compensation: $37,440.00 - $41,600.00 per year
Chesterton Academy of The Divine Family offers a classical, integrated high school education rooted in the Catholic intellectual and spiritual tradition. As part of the Chesterton Schools Network, our mission is to form a new generation of joyful leaders and saints through a curriculum centered on truth, beauty, and goodness. With daily Mass, strong academics, and a vibrant community life, we help students discover their vocation and grow in virtue. Our affordable tuition model ensures that families of all backgrounds can access this transformative education.
(if you already have a resume on Indeed)