Executive Director, Cape Charles Main Street

Executive Director, Main Street Program
Position Overview

The Executive Director serves as the strategic leader, chief advocate, and public representative for the Main Street program. This position coordinates, facilitates, and advances the revitalization of the downtown district through implementation of the National Main Street Four-Point Approach: Design, Economic Vitality, Organization, and Promotion.

The Executive Director works collaboratively with downtown business owners, residents, civic organizations, local government agencies, and community stakeholders to foster sustainable economic growth, strengthen community identity, and enhance the vitality of the downtown district.
In addition, the Executive Director of the Cape Charles Main Street organization is responsible for overseeing the marketing and promotion of the Town of Cape Charles.

The position also supports tourism development, community engagement, special events, business recruitment and retention efforts, and initiatives that enhance the overall visitor and resident experience in Cape Charles.

Core Responsibilities

Strategic Organization & Fundraising

Manage all administrative aspects, including record-keeping, the preparation of reports for state certification and the Main Street America “Data Bonanza”.
Lead the financial planning effort including the development of the annual budget in collaboration with staff, Board Directors, and the Treasurer
Supervising and mentoring staff, provide regular feedback, and opportunities for growth.
Lead comprehensive fundraising efforts, including managing large-scale corporate sponsorships (exceeding $65,000 annually) and residential donor mailings.
Develop and execute tiered sponsorship schedule/timelines to maximize revenue and resource allocation across signature events.
Recruit, organize, and manage an active volunteer force, utilizing post-event surveys to ensure organizational efficiency and volunteer satisfaction.

Data-Driven Promotion & Marketing

Oversee the town’s tourism and brand identity, managing both Main Street and Town Tourism digital platforms.
Execute sophisticated digital marketing campaigns, tracking key performance indicators (KPIs) such as impressions, reach, and Cost Per Click (CPC) across regional markets.
Act as a proactive Public Relations agent, hosting travel writers and securing placements in national and regional lifestyle and travel publications.
Coordinate major events and perform strategic post-event analysis via business surveys and visitation data (e.g., Placer.ai) to drive future growth and ensure alignment with Main Street’s mission, community needs, and strategic goals.
Develop, execute, and manage the marketing for the Town of Cape Charles including print and digital advertising campaigns, social media platforms including Facebook and Instagram, and the organization’s tourism and community website, CapeCharlesVirginiasCape.com.

Economic Vitality & Advocacy

Identify, write, and manage complex grant portfolios, including VTC marketing grants, local government grants, and private corporate grants (e.g., T-Mobile, Arrivalist).
Serve as a liaison to Town Council and public works, attending regular Council meetings, coordinating infrastructure organization/coordination for events, and advocating for downtown business needs.
Attend weekly Town Staff meetings held by the Town Manager to ensure alignment with Town events and other initiatives that affect CCMS activities.

Design & Historic Preservation

Collaborate with town officials on infrastructure projects, such as bike racks, welcome centers, and public space enhancements.
Document physical changes to the downtown district and maintain knowledge of Town ordinances affecting the Main Street overlay area. The ED should know the Town ordinances, but the town documents change.

Board of Directors

Works collaboratively with the Board of Directors to set priorities, manage resources and ensure mission alignment.
Support board development and engagement by preparing clear reports, advising on best governance practices, helping recruit and train board members.

Job Requirements

Education: Bachelor’s degree in community development, business economics, marketing, public administration, or a related field, or equivalent work experience.
Experience: Proven experience in non-profit management, economic development, or high-level marketing/promotion.
Technical Skills: Proficiency in word processing, Excel, donor management systems, and QuickBooks; advanced skills in social media management and digital advertising analytics.
Communication: Exceptional oral and written communication skills, with the ability to function effectively in independent and public-facing situations.
Attributes: Dynamic, entrepreneurial self-starter with strong leadership, communication, and relationship-building skills, capable of managing multiple projects and engaging diverse community stakeholders. Demonstrates a thoughtful approach to historic preservation and community design while advancing innovative strategies that support downtown revitalization, economic vitality, and a vibrant, welcoming community in Cape Charles.

Physical Demands & Travel

Work is performed in both an office setting and the downtown district, requiring significant walking and the ability to access buildings via stairs.
Ability to lift or move a minimum of twenty-five pounds or more, set up at events with tents, tables, and chairs etc.
Must possess a valid driver’s license.
Ability to work a flexible schedule, including evenings and weekends for meetings and special events.
Required attendance at state-level retreats and professional development training courses for Main Street certification.

Position Announcement: Executive Director
Organization: Cape Charles Main Street
Location: Cape Charles Virgina
Position Type: Full-Time
Salary Range: $55,000-$60,000
Application Deadline: July 17, 2026

Overview

Cape Charles Main Street is seeking a dynamic, visionary, and results-driven Executive Director to lead our organization. The Executive Director will provide strategic leadership, oversee daily operations, and advance our mission, programs, and community impact.

Key Responsibilities

• Provide overall leadership, vision, and strategic direction for the organization
• Oversee operations, programs, and financial management
• Build and maintain strong relationships with stakeholders, partners, and the community
• Support and collaborate with Board of Directors
• Lead fundraising, resource development, and grant initiatives
• Ensure compliance with all applicable laws, policies, and regulations

Qualifications

• Proven leadership experience in a nonprofit, governmental, or organizational setting
• Strong financial management and strategic planning skills
• Excellent communication, interpersonal, and organizational abilities
• Experience working with or reporting to a governing board
• Bachelor’s degree in marketing, communications, business or public administration, non-profit management or related field required. Master’s degree preferred.

Application Process

Interested candidates should submit the following:
• Resume
• Cover letter (required) outlining qualifications and interest in the position

Applications will be accepted through July 17, 2026.
Submit applications to: applications@capecharlesmainstreet.com