Chief of Staff / Special Assistant to the CEO

Job Description

Job Description

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 CEOs 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 CEOs 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 CEOs 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 CEOs 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

Application Requirements

Only applicants who submit all of the following will be considered :

1. Cover Letter tailored to this position.

2. Resume detailing relevant work history and skills.

3. Questions please answer the following in a separate document and submit as a PDF :

1. You have access to my calendar and see that I have back-to-back meetings from 9 AM to 8 : 30 PM. At 10 AM, you receive an urgent email from a community partner requesting a last-minute meeting today to discuss a time-sensitive issue. At the same time, you remember I told you I have a date with my husband directly after my last meeting. How would you handle this situation?

2. A team member submits a draft press release for my review, but it contains several errors and doesnt meet the standard of quality I expect. Ive asked you to address this with the team member. How would you communicate this feedback to them?

3. Youre reviewing my emails and notice a message from a donor who is upset. The donor expresses frustration but does not provide a specific reason. How would you handle this situation?

4. During a major community event, a drag performer who is part of the cast of a TV series cancels last minute. The performers gig with us is tied to their role in the TV series, meaning the entire productionincluding the cast and show formatis predetermined. This makes finding a replacement far more complex than simply booking another performer. How would you address this situation?

5. I have a busy day of meetings with multiple stakeholders and events, and you are in charge of travel, transportation, and providing executive support. How would you organize and manage all the pertinent details to ensure the day runs smoothly while also serving as an ambassador for the organization?

6. You overhear a conversation between two team members or volunteers making dismissive comments about the LGBTQ+ community. How would you handle this situation?

7. Ive asked you to help me prepare for a major grant application deadline. The application requires detailed financial data, program metrics, and a narrative proposal. How would you approach this task?

8. How do you define cultural competence, and how does it apply to working with LGBTQIA+ communities?

9. What steps do you take to ensure that programs, services, or communications are culturally relevant and affirming for LGBTQIA+ individuals from diverse backgrounds?

To Apply

Please submit the above materials to employment@mocopridecenter.org :

Applications will be reviewed on a rolling basis until the position is filled.

Flexible work from home options available.