Ms. Winston McGregor

Ms. Winston McGregor

Chief Operations Officer

Winston McGregor is a community leader with more than 25 years of experience leading nonprofits and public private partnerships with a focus on leveraging resources creatively to help people build better lives.

She served as Executive Director and then President of the Guilford Education Alliance (GEA) from 2013 – 2023. She was also appointed and then elected to serve as the at-large member of the Guilford County Board of Education from 2018 – 2022. She served as Chair of the Policy Committee, on the Joint Facilities and Capital Planning Committee, and as Vice Chair of the Board during a dynamic time of change and transition. She played a key role in galvanizing the community behind two successful bond initiatives, the second $1.7B bond effort was, at the time, the largest school bond initiative passed in NC history and the 3rd largest in the country.

Prior to her work in public education, McGregor served a decade as Development Director and then President of one of the largest Habitat for Humanity affiliates in the country, managing $15M in construction, real estate, and mortgage assets. She was awarded the prestigious Kavanaugh Cup for her contributions to expand affordable housing.

She has been honored as an Outstanding Woman in Business by the Triad Business Journal, a 2019 Woman of Distinction by Empowered Girls of NC, and with the 2019 Public Education Champion and Humanitarian Award by the Motivational Foundation. With her leadership, GEA was named the 2015 Non-Profit of the Year by the Guilford Nonprofit Consortium and the 2020 Outstanding Philanthropic Organization by the Triad Chapter of NC Association of Fundraising Professionals. For her service on the Board of Education, McGregor was honored by the Greensboro Regional Realtors Association with their 2023 Outstanding Public Service award.

A graduate of American University in Washington, DC, McGregor launched her career working in the national political arena in various fundraising and project management roles with, first, U.S. Senator, and then, Vice President Al Gore, as director of development for the Democratic Leadership Council and the Progressive Policy Institute and as executive director of the American Council of Young Political Leaders, a U.S. State Department funded nonprofit facilitating international exchanges for U.S. and global political leaders.

Winston grew up in Madison and Greensboro, NC, as well as Corpus, Christi, TX. She now lives in Rockingham County, NC. She and her two young adult sons were prepared for the world by excellent public schools. Her sons are proud graduates of N.C. State and Appalachian State University.

PO Box 99109 | Raleigh, NC 27624
984.664.5411 | Email:

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