Downtown Sykesville Connection - Executive Director

About the Organization

The Downtown Sykesville Connection (DSC) is an accredited Maryland Main Street and Arts & Entertainment District organization dedicated to strengthening Downtown Sykesville as a vibrant place to live, work, visit, invest, and do business.

About the Role

The Executive Director serves as DSC’s organizational and community leader, overseeing strategic planning, economic development initiatives, fundraising and grant management, marketing and promotions, community partnerships, events, staff and volunteers, financial and organizational operations, and advocacy.

The position works closely with downtown businesses, property owners, municipal and state partners, residents, sponsors, community organizations, and the DSC Board of Directors.

We are looking for a collaborative leader who can balance big-picture strategy with hands-on implementation; cultivate strong relationships across diverse stakeholder groups; identify opportunities and resources; and translate ideas into measurable community and economic impact.

The ideal candidate understands that successful downtown revitalization is about building a resilient local economy, strengthening community connections, supporting small businesses, and creating a downtown where people feel welcomed and invested.

Responsibilities

• Lead strategic planning and implementation of economic development initiatives
• Oversee fundraising, grant management, and financial operations
• Manage marketing, promotions, and community events
• Develop and maintain partnerships with businesses, property owners, municipal/state agencies, residents, sponsors, and community organizations
• Supervise staff and volunteers
• Advocate for downtown revitalization and the Main Street Approach®

Requirements

• Experience in nonprofit management, economic development, community development, or Main Street programs
• Proven leadership in strategic planning and hands-on implementation
• Strong relationship-building skills across diverse stakeholder groups
• Passion for place-based economic development and the Main Street Approach®
• Highly organized, resourceful, and comfortable working independently
• Creative problem-solving and ability to drive measurable community impact

Location: Sykesville, Maryland
Target Start Date: October 2026