Executive director

Cape Charles Main Street is seeking an Executive Director to lead our 501(c)(3) organization into its next chapter of balanced, sustainable community stewardship. The ideal candidate will drive high-level strategic impact by securing grants, building consensus with diverse stakeholders, and collaborating with community partners to evaluate and elevate our signature events—ultimately fostering a thriving downtown that honors our historic heritage, fosters sustainable economic development, champions small businesses, and enriches the experience for the entire community.

A central priority for this role is executing creative, year-round marketing and promotional outreach, with a primary focus on the non-summer offseason. The Executive Director will leverage innovative digital campaigns, compelling storytelling, and targeted regional marketing to sustain peak-season momentum, strengthen the shoulder-season economy, and preserve the town's quality-of-life balance.

We expect that this candidate will have proven experience in non-profit management, board leadership and development, strong technical and marketing management skills, and bring a self-starting, positive attitude. Existing familiarity with Virginia’s 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

• 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.
• 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 nonsummer 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.
• Technology Integration & Operations
  • Direct and maintain the organization’s administrative pipeline and digital tools (including Bloomerang, Placer.ai, Quick Books, 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…