Executive Administrative Assistant (Onsite) – Annapolis

The Squires Group, Inc.; Edgewater (MD); On-site; USD 43,000 - 58,000; Full time

Job summary

The Squires Group, Inc. is seeking an Executive Administrative Assistant for a full-time, onsite role in the Annapolis, Maryland area.

In this highly visible position, you will provide confidential support to executive leadership, coordinate board activities, handle facilities, purchasing, financial administration, events, and daily operations. The ideal candidate anticipates needs, manages competing priorities with confidence, and creates an organized, professional, welcoming environment while

Qualifications

• 2–4 years of executive-level administrative support experience in an educational, nonprofit, or mission-driven environment.
• High school diploma or equivalent is required; bachelor’s degree preferred.
• Strong proficiency in Google Workspace and Microsoft Office; experience with QuickBooks or similar financial software is a plus.
• Proven ability to manage complex calendars, coordinate projects and events, prepare professional documents, and maintain organized records.
• Excellent communication, organizational, and multitasking skills, with strong attention to detail.
• Sound judgment, discretion, and professionalism when handling confidential information.
• A proactive, collaborative, and service-oriented approach, with the ability to remain composed as priorities change.
• Ability to successfully complete required background screening.

Responsibilities

• Manage executive calendars, correspondence, travel, meetings, and confidential information.
• Coordinate board meetings, materials, minutes, records, hospitality, and follow-up.
• Support strategic planning, accreditation, compliance reporting, and organizational deadlines.
• Coordinate facilities, maintenance vendors, rentals, purchasing, inventory, and supplies.
• Assist with expense tracking, reimbursements, deposits, transfers, and budget documentation.
• Plan major events, leadership meetings, family programs, and school-wide activities.
• Provide professional front-office support, including greeting visitors and managing calls and mail.
• Maintain organized records and collaborate across departments to support smooth daily operations.

Skills

Executive support

Calendar management

Communication skills

Organizational skills

Discretion & professionalism

Google Workspace

Microsoft Office

QuickBooks

Background screening compliance

Education

High school diploma

Bachelor's degree (preferred)

Tools

Google Workspace

Microsoft Office

QuickBooks

Job description

The Squires Group, Inc. is seeking an Executive Administrative Assistant for a full-time, onsite role in the Annapolis, Maryland area.

In this highly visible position, you will provide confidential support to executive leadership, coordinate board activities, handle facilities, purchasing, financial administration, events, and daily operations. The ideal candidate anticipates needs, manages competing priorities with confidence, and creates an organized, professional, welcoming environment while