Sykesville Connection - Executive Director

Executive Director | Downtown Sykesville Connection | Sykesville, Maryland

The Downtown Sykesville Connection (DSC) is seeking a dynamic, strategic, and community-minded Executive Director to lead our accredited Maryland Main Street and Arts & Entertainment District organization.

This is a unique opportunity for an experienced nonprofit, economic development, community development, or Main Street professional to lead a well-established organization dedicated to strengthening Downtown Sykesville as a vibrant place to live, work, visit, invest, and do business.

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 is creative, resourceful, highly organized, comfortable working independently, and passionate about place-based economic development and the Main Street Approach®. This position requires someone who understands that successful downtown revitalization is about more than events or promotion—it is about building a resilient local economy, strengthening community connections, supporting small businesses, and creating a downtown where people feel welcomed and invested.

Location:

Sykesville, Maryland
Final date to receive applications:
September 18, 2026
Target

Start Date:

October 2026