Office Manager and Executive Assistant - High School

Chesterton Academy of the Divine Family

Hagerstown, MD

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JOB DETAILS

SALARY

$37,440–$41,600 Per Year

SKILLS

Administrative Skills, Calendar Management, Communication Skills, Conferences, Dental Insurance, Detail Oriented, Educational Administration, Event Management, Executive Assistant Skills , Facilities Management, Fundraising, Health Insurance, Interpersonal Skills, Leadership, Logistics, Marketing, Microsoft Office, Multitasking, Nursing, Office Management, Operational Support, Operations, Operations Management, Organizational Skills, Presentation/Verbal Skills, Problem Solving Skills, Safety Process, School Attendance, Secondary School, Team Player, Training/Teaching, Training/Teaching Curriculum, Tuition Fees, Vision Plan, Volunteer Management, Writing Skills

LOCATION

Hagerstown, MD

POSTED

3 days ago

Responsive recruiter

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.

Office Manager and Executive Assistant - High School

Chesterton Academy of the Divine Family

Hagerstown, MD

About the Company

Chesterton Academy of the Divine Family

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