Executive Assistant Jobs in Chester, MD (NOW HIRING)

Chief Engagement Officer and Chief Growth Officer

Dwyer Workforce Development's (DWD) mission is to provide comprehensive support to individuals who lack opportunity and aspire to pursue a career in the healthcare industry, alleviating a severe healthcare workforce shortage, and improving the lives of seniors and the community.

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At Dwyer Workforce Development, how we work matters as much as what we achieve. Every team member is expected to operate in alignment with our core values.

• Integrity Doing the right thing even if no one is looking.
• Empathy Actionruled compassion.
• Ingenuity Big ideas and solutions.
• Accountability Ownership in every action.
• Collaboration The power of we over me.

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Position Summary

The Executive Assistant provides high-level administrative, operational, and project coordination support to the Chief Engagement Officer and Chief Growth Officer.

This position serves as a trusted partner who ensures executive priorities remain organized, communications are professional and timely, projects continue moving forward, and day-to-day operational details are proactively managed.

The Executive Assistant anticipates executive needs, exercises excellent judgment, and maintains the highest level of professionalism and confidentiality while interacting with internal staff, community leaders, healthcare partners, government agencies, donors, and executive leadership.

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Responsibilities

Executive Calendar and Schedule Management

• Manage complex executive calendars across multiple priorities.
• Coordinate meetings with internal and external stakeholders.
• Anticipate scheduling conflicts and proactively recommend solutions.
• Prepare daily and weekly executive agendas.
• Ensure executives have necessary materials prior to meetings.
• Coordinate meeting logistics including technology, locations, and materials.
Executive Communications
• Draft professional correspondence, presentations, and meeting summaries.
• Monitor assigned executive email accounts and prioritize communications.
• Respond to routine inquiries on behalf of executives when appropriate.
• Prepare followup communications after meetings.
• Coordinate communication between executives and internal departments.
• Maintain professional communication with executive leaders from partner organizations.

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Travel and Event Coordination
• Arrange executive travel, lodging, transportation, and itineraries.
• Prepare detailed travel packets and schedules.
• Coordinate conference registrations and event logistics.
• Manage expense documentation and reimbursement preparation.
• Support executive participation in community events and speaking engagements.

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Project Coordination -Primarily supporting the Chief Engagement Officer:
• Track strategic initiatives and implementation timelines.
• Coordinate meetings for crossfunctional projects.
• Document action items and monitor completion.
• Follow up with departments regarding assigned deliverables.
• Maintain project plans and implementation schedules.
• Assist with preparing executive reports and presentations.
• Coordinate and prepare comprehensive meeting materials and executive briefing documents for highlevel meetings with donors, strategic partners, and corporate, foundation, and government stakeholders.

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Executive Office Operations - Primarily supporting the Chief Growth Officer:

• Anticipate daily operational and administrative needs.
• Prepare meeting materials and briefing documents.
• Coordinate office visitors and executive hospitality.
• Organize files, electronic records, and confidential documents.
• Ensure executive workspaces remain prepared for meetings and visitors.
• Manage recurring administrative processes.
Relationship Coordination
• Serve as a professional point of contact for community partners and executive stakeholders.
• Build positive working relationships across DWD departments.
• Coordinate executive meetings with healthcare organizations, educational institutions, employers, and community partners.
• Maintain confidentiality while representing executive leadership.
• Demonstrate diplomacy, discretion, and exceptional customer service.

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Administrative Excellence
• Prepare reports, spreadsheets, presentations, and executive dashboards.
• Maintain accurate records and documentation.
• Coordinate document routing for approvals and signatures.
• Assist with board meeting preparation as assigned.
• Support special projects and organizational initiatives.
• Identify opportunities to improve executive workflow and administrative efficiency.

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Qualifications

Education

Associate's degree required. Bachelor's degree preferred.

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Experience
• Five or more years supporting senior executives.
• Experience managing multiple executive calendars.
• Experience coordinating projects with multiple stakeholders.
• Experience preparing executive correspondence and presentations.
• Experience working with confidential information.
• Nonprofit, healthcare, higher education, or workforce development experience preferred.

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Technical Skills
• Microsoft Office Suite (including Outlook, Teams, PowerPoint, Excel and Word)
• SharePoint
• Calendar management software
• Virtual meeting platforms
• Ability to learn Salesforce and other organizational systems
Professional Competencies
• Exceptional organizational skills
• Outstanding written and verbal communication
• Strong project coordination abilities
• Executive presence and professionalism
• Ability to anticipate needs before being asked
• Sound judgment and discretion
• High attention to detail
• Ability to manage competing priorities
• Strong followthrough
• Adaptability in a fastpaced environment
• Ability to work independently
• Relationshipbuilding skills
• Problemsolving mindset

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Success in This Role

Success in this position means the Chief Engagement Officer and Chief Growth Officer can focus their time on strategic leadership because the Executive Assistant has created reliable systems, anticipated operational needs, coordinated communications, and ensured projects continue progressing without requiring constant oversight.

The successful Executive Assistant becomes a trusted extension of executive leadership—bringing organization, professionalism, responsiveness, and consistency to every interaction while strengthening the effectiveness of the executive team and supporting DWD's mission.

What We Offer
• Health, dental, and vision insurance
• Disability and life insurance
• 403(b) retirement plan with employer match
• Generous PTO and holiday pay
• A team that values flexibility, inclusivity, and collaboration

Equal Employment Opportunity: Dwyer Workforce Development is an Equal Opportunity (EEO) employer. It is the policy of the Company to provide equal employment opportunities to all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

Sponsorship in US: Must be eligible to work in the U.S. without Sponsorship.