Executive Director, Cape Charles Main Street

Position Overview

Cape Charles Main Street is seeking an Executive Director to lead our 501(c)(3) organization into its next chapter of balanced community stewardship. The ideal candidate drives high-level strategic impact by securing major grants, fostering alignment among diverse stakeholders, and actively collaborating with community partners to evaluate and enhance the quality of our signature events.

A central priority for this role is driving creative, year-round marketing and promotional outreach—particularly during the non-summer offseason. The Executive Director will leverage innovative digital campaigns, storytelling, and targeted marketing strategies to keep Cape Charles top-of-mind for residents, regional neighbors, and off-peak visitors alike. We expect that this candidate has proven experience in non-profit management, board leadership and development, strong technical and marketing management skills, and brings a self-starting, positive attitude. Existing familiarity with the Eastern Shore is highly preferred.

Compensation: $70,000 – $80,000 salary range
Employment Type: Full-Time, Exempt
Reports To: Board of Directors
Direct Reports: Marketing Assistant, Event & Logistics Coordinator (Part-Time, Hourly), book-keeper

Core Responsibilities

Strategic Marketing & Offseason Promotion

Develop and execute innovative, data-driven, marketing strategies and creative outreach campaigns designed to promote Cape Charles during the shoulder and winter non-summer seasons.

Keep Cape Charles top-of-mind for both local residents and off-peak tourists through compelling digital content, storytelling, targeted regional advertising, and collaborative promotions.
Oversee brand positioning, digital campaigns, media relations, and promotional partnerships that support downtown merchant vitality year-round.

Public Diplomacy & Stakeholder Alignment

Serve as the primary, high-level liaison between Cape Charles Main Street, the Town Council, municipal staff, merchant associations, residential partners, and regional stakeholders such as the Eastern Shore of Virginia Tourism Commission and the Eastern Shore of Virginia Chamber of Commerce among others.
Proactively frame Main Street’s mission of commercial promotion juxtaposed with sustainable economic resilience and quality-of-life preservation.
Actively engage with local merchants, residents, town/county officials, and sponsors at all levels to foster open communication and cultivate strong community relationships.

Capital Generation & Non-Profit Financial Management

Identify projects that correspond to the Town’s strategic plan, and research, write, and secure federal, state, and private funding streams (including DHCD, Virginia Main Street grants, historic preservation funds, and rural infrastructure awards, among others).
Secure and diversify the organization’s funding model by combining grant income with corporate partnerships, annual fund campaigns, earned income strategies, and event-driven revenue.
Maintain sound financial management and budget oversight across all organizational funds, accounts, and grant awards in coordination with the Board of Directors.

Technology Integration & Operations

Direct and maintain the organization’s administrative pipeline and digital tools (including Bloomerang, Placer.ai, QuickBooks, Canva, Google Suite, social media aggregators, and Meta platforms).
Supervise part time staff to ensure operations are goal-directed and remain on track, introducing them to technology to streamline workflows where appropriate, so the Marketing Assistant and Event Coordinator can focus on higher value tasks.
Report clear marketing performance metrics directly to the Board of Directors, merchants and Town Council.

Qualifications & Requirements

Experience & Skills

Leadership & Governance: Minimum 7–10 years of experience navigating complex local government structures, public-private partnerships, marketing strategy, or non-profit stakeholder management. Proven track record in board leadership, development, and team management. Familiarity with the workings of Main Street America is a plus.
Marketing & Creative Outreach: Demonstrated expertise in multi-channel marketing, digital storytelling, content strategy, and creative campaigns aimed at driving tourism and resident engagement.
Grant Writing: Documented track record of successfully researching, writing, and administering institutional or municipal grants ranging from $5,000 to $50,000+.
Technical Proficiency: Demonstrated strength in modern operational automation tools and software. Eagerness to innovate with AI and software tools for CRM optimization, content scheduling, and analytics reporting.
Communication: Excellent oral and written communication skills with an eagerness to actively interact and build relationships with a wide variety of community stakeholders.

Education

Bachelor’s Degree in Marketing, Business Administration, Non-Profit Management, Public Administration, Communications, or a related field (or equivalent combination of education and 7–10+ years of senior management experience).

Physical Demands & Work Environment

Ability to work in a standard office environment, operate office/computer equipment, and sit or stand for extended periods.
Ability to move about during outdoor community events and stakeholder meetings across the historic district.
Occasional lifting and moving of light promotional materials or media equipment (up to 25–30 lbs).
Requires a flexible, output-driven schedule with occasional evening meetings (Town Council, Board) and weekend event attendance.

How to Apply

This position is open until filled. Interested candidates should submit a resume and a cover letter outlining their qualifications and interest in the position to applications@capecharlesmainstreet.com.