Executive Director Opportunity

APPLICATION PERIOD is CLOSED as of TUESDAY, 7/15/25

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Executive Director Job Description

PlayAnnapolis is seeking a strategic, community-driven, and enthusiastic Executive Director to lead a powerful collective effort to ensure ALL youth in Annapolis have access to recreation and sports year-round. This is a unique opportunity to work alongside a broad and diverse network of partners who are united by a shared vision and commitment to a more diverse and inclusive community that improves the quality of life for ALL youth through recreation and sports. With support from our Board and Coalition Crew, the Executive Director will ensure effective communication, authentic engagement, and strong collaboration among partners, community members, schools, government agencies, donors and other key stakeholders, driving the successful implementation of our shared strategic plan—the Playbook. This is a unique opportunity to advance lasting change in the City of Annapolis through collective action and impact.

Position Information:

• Contractual position

• Salary: $50,000 - 70,000 (commensurate with experience) 

• Hours: Part-time, up to 30 hours a week 

• Hybrid: Remote with in-person work in Annapolis, MD

• Start Date: Late Summer - Fall 2025

Key Skills & Responsibilities:

Organizational Leadership & Strategic Implementation

• Collaborate with the Board of Directors and Coalition Crew to develop an action-oriented strategic plan - Playbook - and lead implementation in alignment with the priorities, strategies, and performance measures

• Support and attend quarterly Board meetings

• Ensure compliance with all legal and regulatory requirements

• Cultivate a culture of transparency, inclusion, and collaboration within the organization and all its stakeholders

• Assess risks and opportunities for sustainable growth and success

Coalition Crew Engagement & Volunteer Management

• Recruit, retain, and manage the PlayAnnapolis Coalition Crew - a broad and diverse group of volunteer members representing local nonprofit organizations and other partners, advocates and supporters

• Organize quarterly in-person meetings with curated agendas and guest speakers

• Support and participate in bi-monthly virtual meetings of the three Action Teams: Fundraising, Marketing, and Advocacy

• Ensure all team actions are coordinated and aligned with Playbook strategies to support collective action and impact

Partnership Development 

• Build and maintain strong relationships with key partners, including leaders in sports and recreation and representatives from city, county, and state entities

• Actively identify and cultivate new partnership opportunities to support a robust Coalition Crew as well as PlayAnnapolis’programs, marketing, advocacy and fundraising

Advocacy 

• Research and analyze local, county, and state policies or budget proposals that could affect PlayAnnapolis’s work

• Work with partners to identify key policy and fiscal issues and advocate at the state, county and local levels to advance the mission of PlayAnnapolis

• Ensure advocacy is informed by collective knowledge and community needs

Marketing & Communications

• Develop and execute a robust social media strategy to enhance visibility and engagement

• Maintain and optimize the PlayAnnapolis website for SEO, updating regularly with fresh content and resources

• Draft and distribute engaging monthly newsletters to subscribers

• Lead planning and promotion of the Annual Sports Fair

• Facilitate stakeholder research for the development of a central registration system to launch in 2026

Fundraising & Development

• Engage donors and cultivate long-term philanthropic relationships

• Research, write, and submit grant proposals aligned with organizational priorities.

• Oversee grant agreements and ensure compliance with reporting requirements

• Plan and execute two annual fundraising events:

  • Trailblazer Tribute (Winter)

  • Annapolis Blues Tailgate (Early Summer)

Scholarship & Interscholastic Programming

• Develop and manage interscholastic sports opportunities in collaboration with Community School Managers

• Maintain strong relationships with partner organizations to expand access

• Oversee the scholarship application and award process, ensuring smooth integration into partner programs

Community Research & Evaluation

• Design and distribute community surveys for sports nonprofits, partners, and participants every three years

• Prepare, market. analyze and present results of the next comprehensive survey in 2026

Public Representation & Leadership

• Represent PlayAnnapolis at local events, meetings, and functions.

• Champion the organization’s mission and vision in the public eye and across sectors

Qualifications: 

• A minimum of 3 years of relevant experience, preferably including experience working with the nonprofit or the public sector 

• Experience working directly with, or in organizations that serve, communities of color, economically disadvantaged communities, and populations with limited access to recreational opportunities

• Proficiency in Microsoft Office platforms (Word, Excel, PowerPoint), commonly used social media platforms, web-based communications platforms, and a willingness to learn our web management/hosting platform (WIX)

• Excellent written and verbal communication skills with the ability to support partner and advocacy relationships

• Enthusiastic, self-starter – anticipates what’s needed and enlists help in a timely fashion

• Great collaborator who is eager and willing to work with a diversity of partners and other stakeholders  

• Excellent organizational, administrative, analytical, and creative problem-solving skills

• Keen attention to detail and ability to prioritize while handling multiple projects

• Ability to meet deadlines while juggling multiple assignments

 

Equal Opportunity Employer

 

PlayAnnapolis is an equal opportunity employer.  Applicants are considered for all roles without regard to race, color, religious creed, sex, national origin or citizenship status, age, physical or mental disability, sexual orientation, marital, parental, veteran or military status, unfavorable military discharge, or any other status protected by applicable federal, state or local law.

 

Interested applicants should send a brief (max 2 pages) resume or professional bio and cover letter to Jrortlieb@gmail.com and davissrjamal@gmail.com. 

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APPLICATION PERIOD is CLOSED as of TUESDAY, 7/15/25