Description

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.

About Legacy Greenscapes

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 greenspaces.

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.

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.
 

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.

Requirements

The Ideal Candidate

Required Experience:

- 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.