Executive Assistant & Office Manager

Job Details

Job Location: Main Address - Grasonville, MD 21638

Position Type: Full Time

Education Level: 2 Year Degree

Salary Range: $48,000.00 - $52,000.00 Salary/year

Travel Percentage: None

Job Shift: Day

Job Title: Executive Assistant & Office Manager

Employer: Chesterwye Center, Inc.

Department: Admin

Reports to: Chief Executive Officer

FLSA Status: Exempt

Hours: Full-Time

Salary: $48,000 - $52,000

Effective Date: 01/13/2026

Position Summary: The Executive Assistant & Office Manager is responsible for providing high-level administrative support to the Chief Executive Officer and the Chief Financial Officer while overseeing the daily operations of the office. This role ensures executive priorities are managed efficiently, office systems run smoothly, and administrative processes support organizational goals. The position requires strong organizational skills, discretion, and the ability to manage multiple priorities in a fast-paced environment.

• Serve as primary administrative support to the executive team.
• Assist in organizing the CEO’s workload, calling attention to items of high priority.
• Support all incoming calls.
• Arrange appointment calendar, including scheduling all regular meetings with staff, board of directors, and committees.
• Maintain an accurate filing system (digital and physical).
• Assume responsibility for establishing pleasant, cooperative relationships with staff, helping when needed.
• Assist during the Day Program and residential-based events.
• Responsible for keeping all common spaces, assigned spaces, and equipment clean, safe, and attractive.
• Understand and work toward agency goals/objectives.
• Maintain appropriate confidential records.
• Responsible for typing documents/ meeting minutes.
• Responsible for reviewing work order submissions/ follow-up in iCare Manager.
• Manage incoming calls, emails, and office communications
• Prepare reports, presentations, and internal documents

• Oversee daily office operations and administrative systems
• Maintain office supplies, equipment, and vendor relationships
• Support with coordinating building maintenance, utilities, and service contracts
• Develop and improve office procedures and workflows
• Ensure the office environment is professional, organized, and efficient
• Support HR processes: onboarding, orientation, files, and tracking

• Support the finance department by depositing checks into operations accounts, tasks such as invoice routing, expense tracking, and filing.
• Support the development department with mailing, event organizing, and data entry.
• Maintain organized digital and paper filing systems

Skills & Competencies

• Attention to detail
• Problem-solving and initiative
• Confidentiality and trustworthiness
• Strong interpersonal skills
• Project coordination
• Adaptability and flexibility

• Education: Associate or Bachelor’s degree preferred
• 3–5 years of executive or administrative experience
• Strong organizational and time-management skills
• Excellent written and verbal communication
• High level of professionalism and discretion
• Proficiency in Microsoft Office and Google Workspace
• Ability to manage multiple priorities in a fast-paced environment

Experience:

• Must have access to personal use of a vehicle to conduct agency business.
• Must have a valid driver’s license and an acceptable driving record as determined by criteria established by Chesterwye’s insurance carrier and Chesterwye policy.

Working Conditions:

• 8 hour shift
• Monday to Friday
• Some weekends is required.
• Some lifting up to 50 lbs.

Employee Benefits:

• Health (Vision included)
• Prescription Drug
• Dental
• Short and Long Term Disabilities
• Accidental Death and Dismemberment
• Term Life Insurance
• Group Basic Life and AD&D (100% employer paid)
• Traditional & Roth 401(k) Plans & Employer match
• Vacation
• Sick Leave
• Holidays
• Military Service Leave
• MD Sick and Safe Leave
• Voting leave
• Employee Referral Bonus
• Club One Gym Membership Discount
• Supplemental Insurance Plans (AFLAC)