Executive Director

Shape the future of one of Winchester’s most treasured public spaces in an exciting period of organizational growth.

Legacy Greenscapes is seeking an Executive Director to lead the organization into an exciting new chapter of growth. Reporting to an engaged Board of Directors, this leader will strengthen fundraising, build organizational infrastructure, cultivate meaningful community partnerships, and help shape the long-term vision for an organization poised for continued impact.

Founded in 2017, 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.

Its signature achievement, Legacy Grove , is a privately owned, publicly accessible park created through an extraordinary community visioning process involving hundreds of local residents, civic leaders, educators, designers, and youth. Today, Legacy Grove provides a place for families to gather, children to play, neighbors to connect, and the community to come together through recreation, education, and shared experiences.

As Legacy Greenscapes enters its next chapter, the organization is building on a strong foundation of community support, an engaged Board, and close partnerships with local philanthropy.

The Opportunity

The Executive Director serves as the chief executive and strategic leader of Legacy Greenscapes, working closely with the Board, staff, volunteers, donors, community leaders, and funders to lead the organization's next phase of growth.

This role advances 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 is an opportunity for an entrepreneurial, relationship-driven leader who is equally comfortable building relationships, developing sustainable funding, strengthening organizational systems, and serving as the public face of the organization throughout Winchester and Clark County.

Key Responsibilities

• Lead the organization's strategic direction and long-term sustainability.
• Build systems, policies, and organizational infrastructure while fostering a collaborative, mission-driven culture.
• Partner with the Board to establish priorities, measure success, and strengthen governance.
• Lead fundraising and revenue diversification efforts, including major gifts, grants, sponsorships, annual giving, and emerging opportunities.
• Develop and execute a comprehensive fundraising strategy aligned with organizational priorities.
• Cultivate and steward donors and expand existing partnerships.
• Serve as Legacy Greenscapes' chief ambassador and champion its mission throughout the community.
• Build relationships with community leaders, elected officials, schools, businesses, nonprofits, volunteers, and other stakeholders.
• Increase community awareness, engagement, and support for Legacy Greenscapes.
• Oversee staff, contractors, programming, and the safe, welcoming, and beautiful stewardship of Legacy Grove.
• Balance strategic leadership with operational excellence while managing risk, contracts, and organizational resources responsibly.
• Support and engage the Board of Directors and help build long-term organizational capacity.

What Success Looks Like

During the first year, the Executive Director will:

• Establish trusted relationships with local philanthropy, staff, volunteers, and community partners.
• Develop and begin implementing a clear strategic vision for the organization's future.
• Strengthen fundraising and diversify revenue sources.
• Continue building organizational systems and governance practices.
• Maintain an exceptional experience for visitors, volunteers, and community members.
• Position Legacy Greenscapes for long-term sustainability and continued growth.

Qualifications

Required:

• Demonstrated fundraising success, including major gifts and institutional giving.
• 5+ years of experience leading or helping build a nonprofit organization.
• 3+ years of supervisory experience.
• Exceptional relationship-building skills.
• Experience partnering with nonprofit Boards.
• Strategic thinking balanced with operational execution.
• Outstanding communication and public speaking skills.
• Entrepreneurial energy and a collaborative leadership style.

Preferred:

• Experience in parks, conservation, recreation, education, or placemaking.
• Marketing and storytelling communications experience.
• Experience working with volunteers.
• Familiarity with Kentucky or similar communities.

Why You'll Love This Opportunity

Few Executive Director opportunities offer the chance to combine community impact, entrepreneurship, placemaking, conservation, and nonprofit leadership in one role. At Legacy Greenscapes, you'll have the opportunity to build an organization while helping shape a community.

• Build an organization at an exciting point in its evolution.
• Lead one of Winchester's most treasured community assets.
• Partner with an engaged Board and local philanthropy.
• Make a visible, lasting impact on the community.
• Enjoy broad autonomy and the opportunity to shape the organization's future.
• Help create a legacy that will benefit future generations.

Salary: $90,000–$105,000 , commensurate with experience, plus a competitive benefits package.