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February 17, 2023

Guilford Dialogues 2023: Winston McGregor


A community leader with a focus on non-profits and public private partnerships, Winston McGregor joined the Guilford Education Alliance in 2013 as executive director and was named president in 2020.

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In July of 2018, McGregor was appointed to fill an open seat as the at-large member of the Guilford County Board of Education and was elected in November to serve a 4-year term. In her capacity as a member of the Board of Education, McGregor served as Chair of the Policy Committee before being elected Vice Chair of the Board in December 2020.  She also served as a member of the Joint Capital/Facilities Planning Committee. Her term on the Board of Education expired in December of 2022.  McGregor also serves as member of the NCCJ Board of Directors.
Winston has been an engaged advocate on education, equity, housing, and community issues for three decades. 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 Non-Profit Consortium and the 2020 Outstanding Philanthropic Organization by the NC Association of Fundraising Professionals.   McGregor was also honored by the Greensboro Regional Relators Association with their 2023 Outstanding Public Service award.
Previously, McGregor spent a decade with Habitat for Humanity of Greater Greensboro including six years as president and executive director.  In 2011, the Greensboro Builders Association awarded her the prestigious Kavanaugh Cup for her contributions to expand affordable housing.  
A graduate of American University in Washington, DC, McGregor launched her career working in the national political arena in various 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 non profit facilitating international exchanges for U.S. and global political leaders.  
A Greensboro native, Winston’s two sons attended Lindley Elementary School, Kiser Middle School and Grimsley High School. One is a proud NC State graduate and the other attends Appalachian State University.

Return to the Guilford Dialogues webpage.