Chief of Staff / Special Assistant to the CEO
Organization: Montgomery County Pride Family (Live In Your Truth and MoCo Pride Center, Inc.,)
Location: Montgomery County, MD
Position Type: Full-Time
Salary: $72,000 Annually
Start Date: Immediate
About the Role
The Chief of Staff & Executive Assistant to the CEO is the strategic right hand to Phillip Alexander Downie (he/him), CEO of MoCo Pride Center Inc., and the Montgomery County Pride Family, Executive Director of Live In Your Truth, Co-Chair for The Coalition For Inclusive Schools & Communities. This is a role for a high-capacity leader who is ready to both build and execute — someone who thrives in a fast-paced environment, holds a deep commitment to justice, and knows how to anticipate needs, manage complexity, and move things forward with excellence.
You will be responsible for managing the CEO’s schedule, priorities, and projects, but more than that — you will serve as a core member of the executive team, a trusted proxy, and a thought partner with the ability to lead, organize, and communicate on behalf of the CEO with integrity and grace.
This position requires discretion, initiative, warmth, clarity, and a deep understanding of what it means to support a visionary leader with big ideas and bigger responsibilities.
Key Responsibilities
Executive Support
Manage the CEO’s dynamic calendar, including prioritization, scheduling, and daily coordination across multiple teams and external partners.
Anticipate needs before they arise, proactively preparing materials, talking points, and follow-ups.
Draft and respond to emails, communications, and documents on behalf of the CEO with clarity and professionalism.
Coordinate logistics and details for speaking engagements, media appearances, travel, and special projects.
Chief of Staff Duties
Operate as a key member of the leadership team — translating vision into execution across programs, partners, and staff.
Lead communication with staff and contractors to ensure alignment, follow-through, and accountability.
Provide behind-the-scenes support for major events, productions, campaigns, and launches.
Represent the CEO in meetings and public spaces as needed, maintaining high-level discretion and diplomacy.
Identify problems, build systems, and remove obstacles so the CEO can focus on impact and leadership.
Team & Relationship Management
Ensure that team members, collaborators, and external stakeholders receive timely updates, direction, and responses.
Help manage the CEO’s internal and external relationships — from County officials to creative teams to grassroots partners.
Serve as a connector between the CEO and all arms of the Montgomery County Pride Family ecosystem.
Life Logistics
Coordinate conflicting personal appointments, travel logistics, and life management support with professionalism and care.
Provide high-level support that ensures the CEO’s time, energy, and capacity are used most effectively and intentionally.
Who You Are
Strategic and Operational: You can think like an executive and execute like a chief of staff. You do not just support the work — you move it forward.
Self-Directed: You do not need to be told what to do. You take initiative, find solutions, and make it happen.
A Master Communicator: You write clearly, speak with confidence, and know how to navigate conversations with everyone from elected officials to youth leaders. ● A Systems Thinker: You build new processes when needed, streamline chaos into clarity, and thrive on making things work better.
Warm, Professional, and Mission-Aligned: You care deeply about equity, LGBTQIA+ rights, racial justice, and community liberation — and you
To Apply
Please submit the following materials to employment@mocopridecenter.org:
A cover letter detailing your interest in the role and how your experience aligns with the responsibilities outlined above.
Your resume, including relevant work experience and education.
Applications will be reviewed on a rolling basis until the position is filled.