Executive Assistant

About Gladstone Psychiatry & Wellness

Gladstone Psychiatry & Wellness is a physician-owned outpatient psychiatric practice serving patients throughout Maryland. With locations in Baltimore/Mt. Washington, Columbia, Bethesda, Frederick, and Hunt Valley, as well as statewide telehealth services, we are committed to delivering thoughtful, high-quality behavioral healthcare.

Our organization includes approximately 140 employees with 70 clinicians, and we are proud to celebrate our 10th anniversary this year.

In addition to the clinical practice, we are developing Gladstone Wellness, an emerging coaching and burnout-recovery venture designed to support clinicians and healthcare professionals.

As we continue to grow, we are seeking an exceptional Executive Assistant who can help our CEO remain focused, organized, and positioned to lead effectively across multiple priorities and business initiatives.

About the Role

The Executive Assistant to the CEO is a highly trusted, high-autonomy position supporting the CEO and President, who also maintains a part-time clinical practice.

This role is ideal for someone who thrives in a fast-paced and evolving environment and is comfortable managing complexity across executive leadership, clinical operations, organizational initiatives, business development, and strategic projects.

You will serve as a critical extension of the CEO, helping protect their time, organize competing priorities, anticipate needs, and ensure important commitments and follow-ups do not fall through the cracks.

This is more than a traditional administrative role. We are looking for someone who brings exceptional judgment, organization, initiative, discretion, and the confidence to manage priorities independently.

What You'll Do

Executive & Calendar Management

• Manage a complex and frequently changing calendar that includes clinical responsibilities, executive leadership meetings, board matters, strategic initiatives, travel, and personal commitments.
• Proactively protect the CEO's time by evaluating priorities, identifying conflicts, and creating appropriate space for high-value work.
• Coordinate meetings across multiple locations, leaders, and external stakeholders.
• Manage meeting logistics, travel arrangements, and scheduling changes with professionalism and flexibility.

Communication & Correspondence

• Triage incoming requests, correspondence, and meeting invitations, determining what requires immediate CEO attention, what can be delegated, and what can be addressed later.
• Draft, edit, and prepare executive correspondence, announcements, emails, and internal communications on behalf of the CEO.
• Learn and consistently reflect the CEO's communication style and voice.
• Serve as a professional first point of contact for the CEO's office when interacting with employees, business partners, vendors, clinicians, and outside stakeholders.

Project & Priority Coordination

• Help organize and track multiple executive-level workstreams, which may include corporate structuring initiatives, payer negotiations, leadership programming, business development, marketing, and other strategic priorities.
• Track deadlines, commitments, documents, and follow-up items without necessarily owning the substantive work.
• Follow up with internal and external stakeholders to help ensure commitments and deadlines remain on track.
• Build and maintain trackers, checklists, workflows, and written procedures that improve executive-office efficiency.

Board & Leadership Support

• Coordinate board and executive leadership meetings from preparation through follow-up.
• Prepare agendas, briefing materials, presentations, meeting notes, and supporting documentation.
• Track decisions, action items, and follow-up responsibilities.
• Maintain organized and confidential corporate and board records.
• Assist with preparation of materials for audits, governance matters, or other organizational requirements.

Administrative & Operational Support

• Prepare presentations, reports, and executive-level documents for internal and external audiences.
• Manage executive expenses, invoices, reimbursements, and related documentation.
• Coordinate special meetings, leadership events, and larger organizational gatherings.
• Anticipate needs and proactively address potential issues before they become urgent.

Confidentiality & Judgment

• Handle sensitive clinical, employee, financial, legal, and corporate information with exceptional discretion.
• Exercise sound judgment regarding what information can be shared, with whom, and at what time.
• Represent the CEO and the organization professionally in all interactions.

What We're Looking For

Required Qualifications

• 5+ years of progressive experience supporting senior executives, founders, physicians, or other high-level leaders.
• Experience managing complex calendars involving multiple priorities, locations, and stakeholders.
• Experience in healthcare administration or another highly confidential environment such as human resources, legal, finance, or professional services.
• Exceptional written and verbal communication skills.
• Ability to draft professional emails, executive correspondence, meeting summaries, presentations, and company-wide communications.
• Strong organizational skills with the ability to manage multiple priorities simultaneously.
• Strong judgment, professionalism, and discretion when handling confidential information.
• Advanced proficiency with Microsoft Office and Google Workspace.
• Experience using project or task-management platforms such as Asana or similar systems.
• Comfort working with expense management, travel, meeting, and scheduling platforms.

The Person Who Will Thrive in This Role

Proactive

You notice what needs attention and take action without waiting for detailed instructions.

Solution-Oriented

You bring possible solutions, not simply problems. You take an issue as far as you reasonably can before escalating it.

Highly Organized

You can keep multiple workstreams, deadlines, follow-ups, and commitments moving without losing important details.

Calm Under Pressure

You remain professional, patient, and steady when priorities shift, schedules change, or others are under stress.

Confident Communicator

You communicate clearly and respectfully and are comfortable setting boundaries or saying no on behalf of the CEO when appropriate.

Creative

You look for more efficient ways to approach recurring tasks and improve existing processes.

Technology & AI Comfortable

You are comfortable using technology to improve productivity and are interested in tools such as ChatGPT, Claude, or similar AI platforms to streamline administrative work while maintaining appropriate confidentiality and data-security practices.

Discreet

You understand that trust is foundational to the role and consistently exercise good judgment with sensitive information.

Nice to Have

• Experience working in a physician-owned medical or behavioral healthcare practice.
• Experience supporting a founder, CEO, or executive who balances operational and clinical responsibilities.
• Experience supporting more than one executive or multiple affiliated business entities.
• Experience coordinating large meetings, retreats, or organizational events.
• Experience preparing and distributing board minutes.
• Experience organizing governance, compliance, or audit-related records.
• Familiarity with healthcare terminology, payer relationships, or physician practice operations.

What We Offer

• A unique opportunity to work closely with the executive leadership of a growing, physician-led healthcare organization.
• A collaborative, mission-driven work environment.
• Competitive compensation.
• Comprehensive medical and health benefits.
• Retirement benefits.
• Paid time off and Company holidays.
• Opportunities to contribute to meaningful organizational growth and strategic initiatives.
  

How to Apply

Interested candidates should submit a resume and brief cover letter describing their executive support experience and why they are interested in joining Gladstone Psychiatry & Wellness to https://www.gladstonepsych.com/careers/.

Candidates selected to move forward in the interview process will be asked to complete a brief personality assessment as one component of our overall selection process.

Gladstone Psychiatry & Wellness is committed to creating a professional, inclusive, and respectful workplace. Employment decisions are based on qualifications, experience, organizational needs, and other job-related factors.

One change I would strongly recommend is using 5+ years rather than “3+/5+ years.” Given the complexity, CEO exposure, confidentiality, board support, and multiple-business responsibilities, this reads more like a seasoned Executive Assistant role than an entry-to-midlevel EA position.