President/CEO

Ashley Rountree

$125K — $150K *
Education, Government & Non-Profit
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree required; master's preferred in relevant fields.
  • Minimum 5 years leading a nonprofit or mission-driven organization.
  • Proven success in diverse fundraising and revenue strategies.
  • Strong financial management skills, including budgeting and forecasting.
  • Experience managing small, high-performing teams.
  • Exceptional skills in building relationships across various sectors.
  • In-depth understanding of Kentucky's business environment.

Responsibilities

  • Lead daily operations, ensuring strategic alignment and clarity.
  • Build and manage a high-performance team culture.
  • Champion operational consistency across different programs.
  • Own all revenue streams and drive fundraising efforts actively.
  • Serve as the primary public representative for Canopy.
  • Execute the strategic plan and develop long-term vision.
  • Manage financial health, budgeting, and compliance.

Benefits

  • Eligibility for performance-based bonus tied to organizational goals.
  • Comprehensive benefits package to be discussed with candidates.
Full Job Description
The Opportunity

Canopy is entering a pivotal growth chapter. The organization has completed deep identity work and now needs a leader who can focus, scale, and strengthen what already exists. The next President & CEO will build an institution capable of carrying Canopy's mission across Kentucky by sharpening strategy, expanding revenue, strengthening member value, and serving as a compelling statewide ambassador for Good Business.

The President & CEO will report directly to the Board of Directors and will be responsible for leading the organization through a critical growth phase, executing the [redacted] strategic plan and developing longer-term vision, building and managing a high-performing team, driving revenue and fundraising, serving as Canopy's primary public representative, and cultivating relationships with the Canopy Board of Directors, members, funders, community partners, policymakers, and the broader Kentucky business community.

This role is ideal for an entrepreneurial minded executive who believes in Canopy's mission and has the drive and passion to build a sustainable institution that will be impactful across the Commonwealth. The President & CEO must be able to sit comfortably with business leaders, educators, policymakers, donors, and entrepreneurs, listening well, thinking quickly, speaking clearly, and making people feel both welcomed and challenged. At the same time, the ideal candidate should show integrity, humility, fairness, and commitment to the work more than their personal advancement.

This is a rare opportunity to lead a values-driven organization with statewide influence, a strong foundation, and significant room to grow.

Candidate Responsibilities

Operational Leadership
  • Lead daily operations with clarity and discipline, ensuring alignment between strategic priorities and execution.
  • Build and manage a high performing team.
  • Create a culture of trust, autonomy, and performance accountability where gifted people can do excellent work together.
  • Ensure operational consistency across programs, events, and member services.
  • Maintain transparent communication with staff and board.
  • Champion professional development and continuous improvement across all levels of the organization.

Revenue & Fundraising
  • Own all revenue streams , including membership, sponsorships, individual giving, grants, event revenue, and capital campaign progress.
  • Build diversified pipelines, set targets, make direct asks, close commitments, and hold staff and board accountable for revenue work.
  • Ensure sponsorship renewals are completed on schedule, and new prospects are identified.
  • Conduct corporate stewardship meetings and cultivate donor relationships.
  • Coordinate donor cultivation events and ensure successful implementation of Event Day Giving strategies.
  • Ensure Canopy membership delivers measurable business value.

Relationship Building
  • Serve as Canopy's primary public representative and a credible, compelling, nonpartisan voice for Good Business across Kentucky.
  • Build durable relationships across business, civic, education, philanthropic, and government sectors.
  • Represent Canopy at community events, business forums, and statewide convenings.
  • Strengthen Canopy's visibility as the hub of the Good Business Movement in Kentucky.

Strategy & Growth
  • Execute the [redacted] strategic plan and help shape long- term vision, developing opportunities for statewide strategic growth.
  • Strengthen statewide education partnerships and expand Canopy's reach.
  • Advance the Canopy Certification program as a scalable model for business impact and membership growth.
  • Collaborate with the board to refine organizational priorities and ensure alignment with mission and resources.

Financial Stewardship
  • Manage the organization's financial health, including budgeting, forecasting, and scenario planning.
  • Maintain cash-flow visibility and internal controls that protect Canopy's sustainability.
  • Present clear financial reports and dashboards to the board and leadership team.
  • Balance disciplined cost management with strategic investment in growth and innovation.
  • Ensure compliance with nonprofit financial standards and ethical stewardship of all funds.

Board Partnership
  • Provide clear reporting, strategic and tactical updates, financial transparency, and leadership that fosters effective Board governance.
  • Partner with Board on developmental strategy, effectively leveraging the group to meet fundraising goals.

Candidate Qualifications
  • Bachelor's degree required. Master's degree or higher in Business, Education, Nonprofit Management, or Organizational Leadership, preferred.
  • At least 5 years proven experience leading in a nonprofit, mission-driven organization, business association, or values-aligned enterprise.
  • Demonstrated success in fundraising and revenue diversification, including membership, sponsorships, grants, and campaigns.
  • Strong financial acumen with the ability to manage budgets, forecasting, and cash-flow visibility.
  • Experience building and managing small, high-performing teams.
  • Exceptional relationship building skills across business, civic, education, philanthropic, and government sectors.
  • Deep understanding of Kentucky's business and community landscape, with the ability to build authentic statewide trust.
  • Compelling public communication skills to represent Canopy as a credible, nonpartisan voice for Good Business.

COMPENSATION & BENEFITS

Canopy is prepared to offer a competitive base salary in the range of $125,000-$150,000, commensurate with experience. The position also includes eligibility for a performance-based bonus of 15-20%, tied to the achievement of agreed-upon organizational goals and responsibilities. A benefits package accompanies this opportunity and will be discussed with candidates during the search process.

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