Cape Charles Main Street Seeking New 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.

Job Description: Executive Director

Position Overview

The Executive Director drives 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

Core Responsibilities

Public Diplomacy & Stakeholder Alignment

Serve as the primary, high-level liaison between Cape Charles Main Street, 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 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.

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 5-7 years of experience navigating 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.
Grant Writing: Documented track record of successfully researching, writing, and administering institutional or municipal grants.
Marketing & Creative Outreach: Demonstrated expertise in multi-channel marketing, digital storytelling, content strategy, and creative campaigns aimed at driving tourism and resident engagement.
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 5-7+ 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.

Please send a resume and cover letter detailing your qualifications to applications@capecharlesmainstreet.com before Wednesday August 5.

Pay: $70,000.00 – $80,000.00 per year

Benefits

Paid time off

Work Location: In person