Careers
Be a part of the Legacy Grove Community
Legacy Greenscapes was founded as a nonprofit organization in 2017 to ensure the people of Clark County have access to fun, clean, safe, and beautiful public spaces. Legacy Greenscapes manages and maintains Legacy Grove.
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.
The Position
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.
Key Responsibilities
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.
Fundraising & Revenue Development
Lead all fundraising and revenue diversification efforts, including major gifts, grants, sponsorships, 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.
Community Leadership & 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.
Board Partnership & Governance
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
Operations & Park Stewardship
Ensure Legacy Grove remains safe, welcoming, and beautifully maintained.
Oversee staff, contractors, and programming.
Balance strategic leadership with operational excellence.
Manage risk, contracts, and organizational resources responsibly.
What Success Looks Like
During your first year, you 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.
The Ideal Candidate
Key Responsibilities
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:
Parks, conservation, recreation, education, or placemaking experience.
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.
Compensation & Benefits
Salary: $90,000–$105,000, commensurate with experience, plus a competitive benefits package.
Join Our Team
The Legacy Greenscapes has retained ThinkingAhead Executive Search to lead this search.
Please submit your resume and expression of interest to:
Dan Kuhar
Partner | ThinkingAhead Executive Search
https://thinkingahead.com/opportunities/job/4eaf59f3-1706-4330-9915-f2de0804219c/
The Greater Clark Foundation hired Learning Landscapes Design, a firm nationally known for creating inclusive, outdoor spaces for learning and play using youth civic engagement, to design the two-acre Adventure Play Area with the help of local elementary-aged youth. Regional firms CARMAN and Dean Builds joined the team to design and construct park amenities outside the play area – a welcoming entry plaza, ADA-accessible walking paths, dog parks, open lawns, neighborhood entrances, green infrastructure and native landscaping. The American Ginseng-inspired shade sculpture in the center of the play area was designed and constructed by Prometheus Art. Park construction began in spring 2018 and concluded in June 2020. The park was named Legacy Grove and formally dedicated by The Greater Clark Foundation in June 2021 as a legacy gift to the community.
With the park build complete, Legacy Greenscapes — a new nonprofit dedicated to improving access to parks and greenspace — took on the important role of operating and maintaining Legacy Grove. This privately-owned, public park is open to the public every day of the year and operates solely on donations from park guests and others.
From Concept to Reality
Great Communities have Great Public Parks
When we say, “great communities have great public parks,” we mean it. Public parks enhance our community’s quality of life and well-being. Research backs that up. Public spaces provide spaces for social interaction, foster a sense of belonging and pride in the area, encourage a more outdoor lifestyle, provide opportunities for physical activity and play, and reduce stress.* Other studies show green spaces lower blood pressure, improve attention, and reduce feelings of fear and anger or aggression.
In addition to health and social benefits, great public spaces also have the ability to attract businesses and create jobs. Easy access to parks and open space has become a new measure of community wealth nationwide. It’s an important way to attract businesses and residents by guaranteeing both quality of life and economic health. Corporate CEO’s say quality of life for employees is the third-most important factor in locating a business, behind access to domestic markets and availability of skilled labor.**
*Study by Commission for Architecture and the Built Environment (CABE)
**“How Cities Use Parks for Economic Development,” American Planning Association
ADA Accessibility
Legacy Greenscapes wants Legacy Grove to enrich people’s lives, promote physical and emotional well-being, and provide outlets for fitness and relaxation for the widest possible audience. Legacy Grove was designed with accessibility in mind.
Walking Path
The walking path meets ADA guidelines for accessibility. It is a 1 mile paved loop around the park.
Adventure Play Area
The Adventure Play Area has features for children of all ages and abilities. It is fully fenced and the main path through the playground is ADA compliant. Side paths may contain uneven terrain and steep gradient.
Restrooms
Restrooms have a 5 ft. turning radius, as well as grab bars. All amenities are placed at a height appropriate to people in wheelchairs. In addition, an adult changing table is available.