Executive Director Administrator

Job Description: Executive Director

Position Overview

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

Core Responsibilities

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 eventdriven

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, 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.

 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.

 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.