Executive Director

The Opportunity

Some Executive Director opportunities ask you to maintain what already exists. This one asks you to build what comes next.

Legacy Greenscapes has become one of Winchester and Clark County's most beloved community assets. From the beautiful trails and gathering spaces of Legacy Grove to educational programming and community events, the organization has earned tremendous goodwill and established itself as a catalyst for recreation, conservation, and community connection.

Now, Legacy Greenscapes is entering an exciting new chapter.

As Executive Director, you'll have the opportunity to strengthen fundraising, build organizational infrastructure, cultivate meaningful partnerships, and help shape the long-term vision for an organization poised for continued growth. Working closely with an engaged Board of Directors, dedicated staff, volunteers, community leaders, and funders, you'll help transform a strong foundation into a sustainable organization that will serve Winchester for generations to come.

If you're energized by building organizations, cultivating relationships, and creating lasting community impact, we'd love to meet you.

Legacy Greenscapes is a nonprofit organization dedicated to creating and sustaining vibrant public spaces that strengthen the quality of life for the people of Winchester, Clark County, and the greater Kentucky region. Founded in 2017, the organization was created to ensure that every member of the community has access to fun, safe, beautiful, and welcoming parks and green spaces.

Its signature achievement, Legacy Grove, is a privately owned, publicly accessible park that was born from an extraordinary community visioning process involving hundreds of local residents, civic leaders, educators, designers, and youth. Today, Legacy Grove serves as a place where families gather, children play, neighbors connect, and the community comes together through recreation, education, and shared experiences.

As Legacy Greenscapes enters its next chapter, the organization is building upon a strong foundation of community support, an engaged Board of Directors, and a close partnership with local philanthropy. Stakeholders consistently describe this as an exciting moment in the organization's evolution, one that calls for a collaborative leader who can strengthen fundraising, deepen community partnerships, build organizational capacity, and help ensure Legacy Greenscapes remains a vibrant community resource for generations to come.

Reporting to the Board of Directors, the Executive Director serves as the chief executive and strategic leader of Legacy Greenscapes. Working in partnership with the Board, staff, volunteers, donors, community leaders, and funders, the Executive Director will lead the organization's next chapter of growth while ensuring Legacy Greenscapes remains a vibrant, welcoming, and sustainable community resource.

The Executive Director is responsible for advancing the organization's mission through strategic leadership, fundraising and revenue diversification, community partnerships, organizational development, Board engagement, staff leadership, and stewardship of Legacy Grove and its programming.

This role calls for an entrepreneurial leader who is equally comfortable building relationships, developing sustainable funding, guiding organizational growth, and serving as the public face of the organization throughout Winchester and Clark County.

• Strategic Leadership & Organizational Growth
• Lead the organization's strategic direction and long-term sustainability.
• Build systems, policies, and organizational infrastructure.
• Foster a collaborative, mission-driven culture.
• Partner with the Board to establish priorities and measure organizational success.
• Lead organizational planning and help position Legacy Greenscapes for its next phase of growth.

• Lead all fundraising and revenue diversification efforts, including major gifts, grants, sponsor ships, annual giving, and emerging revenue opportunities.
• Develop and execute a comprehensive fundraising strategy aligned with the organization's strategic priorities.
• Cultivate and steward donors.
• Expand existing partnerships.

• Serve as Legacy Greenscapes' chief ambassador.
• Champion Legacy Greenscapes' mission and tell the organization's story throughout the community.
• Build relationships with community leaders, elected officials, schools, businesses, nonprofits, and volunteers.
• Increase community awareness, engagement, and support for Legacy Greenscapes' mission and impact.

• Partner closely with the Board Chair and Board of Directors.
• Support governance best practices.
• Prepare Board materials and support the board at its meetings.
• Help strengthen board engagement and long-term organizational capacity.

• Ensure Legacy Grove remains safe, welcoming, and beautifully maintained.
• Oversee…