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Executive Director

Winners Travel Foundation

This is a Contract position in Cayce, SC posted September 24, 2021.

Winners Travel Foundation, a 501c(3) nonprofit organization, aims to serve those who serve others. Since 2019, Winners Travel has given caretakers the tools, resources, and experiences to continue their service while simultaneously caring for themselves – through the gift of travel.


Provide life-changing trips to deserving heroes that open the eyes, expand the mind, and heal the soul.


To be a catalyst of hope and a network of inspiration.


We see a world where every person has the opportunity to improve their life through the gift of travel.


Winners Travel is seeking an energetic and entrepreneurial Executive Director (ED) to lead the organization into an exciting future. Reporting to the Winners Travel founding chair, the ED will demonstrate imagination, leadership, and a deep-rooted passion for helping those who care for others. The ideal ED’s strengths also include fundraising skills and a bold and creative strategic vision to enhance Winners Travel’s image as a critical need in the lives of those they serve. With exceptional business acumen, s/he will have overall strategic and operational responsibility for Winners Travel’s programs and the expansion and execution of its mission.


Strategic Leadership

  • Spearhead Winners Travel’s goals and objectives, ensuring they align and remain consistent with overall mission and vision.
  • Ensure ongoing local programmatic excellence, program evaluation, and consistent quality of finance and administration, fundraising, communications, and systems; recommend timelines and resources needed to achieve the strategic goals.
  • Enlist other service leaders to the mission while relating well to all stakeholders. Actively engage and energize volunteers, board members, and funders.
  • Work with the Board of Directors to establish short and long-range action plans, timelines, and strategies to ensure Winners Travel meets established goals and objectives.
  • Demonstrate a proven record of considerable success working through a network of relationships and strategic partners to achieve a specific goal.
  • Set vision, build credibility, and take calculated risks in implementing strategies that will facilitate growth and organizational awareness.
  • Demonstrate a pervasive commitment to data-driven decision-making and a results-oriented leadership style.

Fundraising and Resource Development

  • Expand local revenue generating and fundraising activities to support existing program operations and expansion.
  • Leverage personal contacts and Board relationships to identify potential donors or partners. Effectively communicate Winners Travel’s mission and vision to potential funders.
  • Diversify and increase funding sources (individual and corporate donors), while also identifying and pursuing grants and other funding opportunities.
  • Encourage new stakeholders to align their work around Winners Travel’s goals and encourage funders to align human capital and financial investments in support of organizational strategies.

Public Relations and Outreach

  • Serve as the face of the organization and as an engaging voice for the mission and vision of Winners Travel.
  • Enhance image and create a stronger brand by refining all aspects of communications including development of key messages to be shared on social platforms.
  • Develop and implement a solid and multi-layered communication strategy that includes opportunities to promote small wins and disseminate important publicly available data.
  • Consistently interact with healthcare organizations, the community at large, donors, stakeholders, etc. to garner support and funding for Winners Travel’s initiatives.

Board Development

  • Develop, maintain, and support a strong Board of Directors; Seek and build board involvement with strategic direction for ongoing operations, growth, and development.
  • Work directly with the Board of Directors to develop and cultivate relationships and to lead cross-sector collaborations in using data and metrics as elements of a highly disciplined approach to inform decision-making.
  • Establish accountability by setting defined responsibilities and expectations for all board members.
  • Prioritize intentional interactions with individual board members to build relationships, gather honest feedback, gain support, and promote board stability.
  • Consistently communicate activities, accurate and timely financial information, plans and needs with the officers and Board of Directors during and between board meetings.

Operational Oversight

  • Maintain responsibility for the financial integrity and fiscal management of Winners Travel.
  • Ensure safeguards are in place to audit, measure, and verify business and financial performance and practices.
  • Develop the annual budget and ensure the organization operates within the approved budgets. Submit timely financial statements which accurately reflect the financial condition and performance of the organization.
  • Provide maximum resource utilization and maintain the organization in a positive financial position.
  • Hire, motivate, develop, and retain qualified staff who have a commitment to high-quality programs, problem solving, and collaboration.
  • Establish and support organizational policies, comprehensive processes, paperwork systems, and up-to-date technology systems.
  • Diligently monitor organizational goals and hold him/herself and future team members accountable for reasonable growth and change.

Minimum Qualifications

The ED will be thoroughly committed to Winners Travel’s mission. Candidates should have 3+ years’ demonstrated leadership, organizational, financial, fundraising, and relationship management experience. Preferred qualifications and other experience may include but are not limited to:

  • Bachelor’s Degree or commensurate experience in business management with preferable senior management/non-profit experience.
  • At least 3 years successful experience in creating and implementing fund development plans.
  • Excellence in organizational management with the ability to hire and coach staff, manage and develop high-performing teams, set and achieve strategic objectives, and manage a budget.
  • Past success working with a Board of Directors with the ability to cultivate existing board member relationships.
  • Strong financial background and experience, including budgeting and reporting.
  • Strong marketing, public relations, and fundraising experience with the ability to engage a wide range of stakeholders and cultures.
  • Strong written and verbal communication skills; a persuasive and passionate communicator with excellent interpersonal and multidisciplinary project skills.
  • Action-oriented, entrepreneurial, adaptable, and innovative approach to business planning.
  • Ability to work effectively in collaboration with diverse groups of people.
  • Passion, idealism, integrity, positive attitude, mission-driven, and self-directed.