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 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
  • 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
  • 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
  • Evaluating and measuring the effectiveness of MSC initiatives; including collecting, analyzing, and reporting on data; and making strategic recommendations to the MSC Board


The ideal candidate is a proven leader experienced in business development. 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. Preference will be given to Kent County residents and those willing to relocate to Chestertown.

In addition:

  • Ability to work well with others in a fast-paced environment is essential
  • Excellent written, verbal and interpersonal communication skills are 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 April 15, 2021.

Main Street Historic Chestertown is an Equal Opportunity Employer.