Main Street Chestertown – Executive Director

• Executive Director
• Main Street Chestertown
• Salary: $85,000 annually; flexible schedule, paid time off
• Location: In-person, 122 N. Cross Street, Chestertown, MD 21620
• Filing Deadline: February 20, 2026

Main Street Historic Chestertown (MSC) is a 501(c)(3) non-profit corporation and a designated Main Street Maryland program, with a mission to foster an inviting, diverse, and prosperous downtown Chestertown. The MSC Board of Directors is seeking a highly organized, detail-oriented, self-starting individual for its full-time Executive Director position.

The Executive Director (ED) of MSC is responsible for the management, coordination, administration, documentation, and implementation of MSC’s revitalization program, following the National Main Street Center’s Four-Point approach:

• Organization – Managing the operational aspects of a non-profit organization, extensive fundraising efforts, and building consensus and cooperation among the volunteers, businesses, residents, and organizations that all play roles in the MSC District
• Design – Enhancing and improving the appearance of the MSC District in accordance with the Master Plan, utilizing urban design and historic preservation initiatives
• Promotion – Marketing the MSC District to investors, new businesses, residents, local employees, shoppers, and visitors
• Economic Vitality – Strengthening, building, and diversifying the economic base of the MSC District

Summary of Duties and Responsibilities

The MSC ED is directly accountable to the MSC Board of Directors for the efficient operation of all MSC activities and the MSC office. The Executive Director will be responsible for:

• Providing efficient administrative direction for the organization, including close cooperation with the MSC Board of Directors and adherence to the guidelines and requirements of Maryland Main Street to maintain good standing
• Financial management and planning of the organization, including budgeting, reporting, and monitoring expenditures and revenue
• Management of all paid staff, interns, consultants, and volunteers to achieve the goals and objectives of MSC
• Coordinating the activity of all MSC committees, volunteers, and work teams, and providing oversight to ensure that all projects and programs are executed in a professional, timely, and cost-effective manner
• Working closely with key MSC partners and stakeholders, including downtown property and business owners, all levels of government and their agencies, the network of Maryland Main Street programs, and other local non-profit organizations
• Representing and advocating for MSC by regular attendance at public forums, including Chestertown Mayor & Town Council meetings, regional economic development meetings, meetings of local partner organizations, and public events
• Evaluating and measuring the effectiveness of MSC initiatives, including collecting, analyzing, and reporting on data, and making strategic recommendations to the MSC Board

The Executive Director, with the assistance of support staff and/or non-employee contractors, will also be responsible for the following:

• Management and oversight of MSC’s grant and fundraising program, including researching, writing, and submitting grant applications; performing all administrative work necessary during the lifetime of a grant; and organizing and overseeing community donation campaigns
• Handling or supervising the design and production of all external communication and marketing tools, including but not limited to, website, social media, press releases, signage, newsletters, and print, radio, and/or digital marketing campaigns
• Planning and coordinating community and fundraising events, including MSC signature events, and assisting other community stakeholders with collaborative events

Qualifications

The ideal candidate is a proven leader experienced in program and project management, with excellent written, verbal, and interpersonal communication skills. Candidates should also have education and/or experience in one or more of the following areas: fundraising/development, commercial district management, non-profit administration, economic development, finance, public relations, public administration, historic preservation, and/or small business development.

In addition:

• The ability to work well with others in a fast-paced environment is essential
• Excellent technology skills, including proficiency in G Suite and/or Microsoft Suite, are required
• Experience with digital marketing and social media platform management preferred
• Experience using a CRM database preferred

To apply, please send a single PDF containing your cover letter, resume, and references to employment@mainstreetchestertown.org no later than February 20, 2026.

Main Street Historic Chestertown is an Equal Opportunity Employer.