About Eileen S. Winterble
Healthcare Expertise



Eileen S. Winterble has spent her professional life transforming businesses and careers.

She is a strategist, catalyst and coach with exceptional expertise in leading major change efforts and building cohesive teams in complex business environments. She has served as a top executive in the private and public sectors.

As interim executive director at the Jewish Federation of Greater Orlando, Eileen:

  • Led efforts to set priorities and develop programs to serve the needs of the community.
  • Strengthened governance by streamlining Board composition and committee structure under the new by-laws.
  • Focused the nominating process on recruiting individuals with the skills and commitment needed to carry out Federation priorities.
  • Redesigned fundraising to reflect 21st century philanthropic trends and connect with the next generation of leaders and donors.
  • Improved financial reporting and transparency.
  • Increased operating efficiency.

These actions set the stage for recruitment of an executive director with the qualities needed to lead the Federation forward.

Eileen was the Chief Financial Officer of Harvard Pilgrim Health Care during the turnaround that restored financial stability to one of New England’s largest health care companies. She helped shape Harvard Pilgrim’s turnaround strategy, recruited a highly effective financial team and collaborated with government and industry stakeholders to execute the successful plan.

As CFO of HIP Health Plan of New York, Eileen guided a company-wide strategic planning effort. In addition, she set the foundation for a new model for reimbursing providers and more cost-effective operations.

She also served as Senior Vice President/Strategic Planning at GHI — Group Health Incorporated — where she led planning and M&A activities and company-wide compliance initiatives. Other positions included Executive Director/New York State Medical Care Facilities Finance Agency, investment banker with A.G. Becker and Drexel Burnham Lambert, senior manager in the District of Columbia Office of Management & Budget and member of the Washington, DC office of McKinsey & Company.

Eileen graduated Summa Cum Laude with Honors in Psychology and Phi Beta Kappa from Penn State University.