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Office Administrator

The Chesterton Schools Network

The Chesterton Schools Network

Administration
Annapolis, MD, USA
Posted on Aug 30, 2025

Job Description

Chesterton Academy of Annapolis, a classical high school in the Catholic tradition, founded in 2018, seeks a highly motivated individual who can joyfully and energetically take on the varied administrative duties of a growing school. The role of Office Administrator includes the following duties:

Daily Office Administration
• Manage day-to-day front office operations including:
o Answering the phone and doorbell
o Student attendance
o Parking permits and carpools
o Nursing and sick bay/administering meds and recording health events
o Safety, including emergency drills and procedures
• Manage school, student, and faculty files (current year and archives)
• Assist with faculty onboarding documentation
• Maintain office supplies and curriculum inventories
• Be the primary point of contact for all parent communication
• Send out a weekly parent email Newsletter
• Create and send out a bi-annual Donor Newsletter
• Support the recruiting and admissions team by scheduling and overseeing Shadow Days and tours
• Assist with planning and logistics for various school activities including: Open Houses, Parent-Teacher Conferences (first and second semesters), field days, field trips, testing (placement exams, PSAT, CLT), and other events such as vocation talks, retreats, chaplain visits, etc.
• Point of contact for Anne Arundel County and City of Annapolis compliance/reporting (for water quality, student vaccination report)
Fundraising Support
• Record donations, send to bookkeeper, and write thank you notes
• Provide administrative support for all aspects of annual fundraising and marketing plans, with emphasis on annual Gala
Physical Plant
• Coordinate weekly and special cleaning with Whitfill Cleaning service
• Serve as liaison between school and landlord St. Paul's Church for scheduling all activities

Calendar and Scheduling
• Develop and oversee all school schedules
• Assign substitute responsibilities in event of faculty absences
• Create official school calendar (instruction days, events, etc.)
• Oversee school events and volunteer assignments

Qualifications
1. Ability to adapt to changing work priorities and working with frequent interruptions.
2. Effectively communicate with diverse groups, maintaining utmost confidentiality.
3. Establish cooperative relations in a calm and tactful manner.
4. Proficient computer usage and knowledge of modern office practices.
5. Effective communication techniques and procedures. Communicate effectively in oral and written form.
6. Effectively carry out oral and written directions.
7. Certain aspects of the job are seasonal, so the overall workload can change from time to time.
It is expected that candidates be practicing Roman Catholics and possess a willingness to adhere to the Magisterium of the Catholic Church and the mission of Chesterton Academy of Annapolis as set forth by the Board of Directors .

About the Employer

Chesterton Academy of Annapolis is a classical high school and a member of the Chesterton Schools Network. The network schools are part of an educational movement reintroducing the classical, Catholic liberal arts tradition. At Chesterton Academy, faith is understood not as one subject among many, but as the essential truth from which all academic disciplines flow and drive their meaning. Chesterton Academy of Annapolis opened in 2018. Come join our mission!