Recognized for her professional achievement, community leadership, and dedication to mentoring
Baltimore, Maryland – The Daily Record has named Diedre Windsor, Founder and CEO of Windsor Group LLC , as one of the Top 100 Women in Maryland for the second time. This distinguished award celebrates women leaders who excel in their industries and communities. With over 350 nominations and two competitive rounds of judging, Windsor emerged as a standout leader known for her impact in business and service.
In 2025, The Daily Record is celebrating 30 Years of recognizing 100 high-achieving Maryland women who have made an impact on their community through leadership, service, and mentoring. Since 1995 1,866 women have been named to this list. These individuals have broken the glass ceiling and continue to elevate others and lead by example paving the way for the next generation.
“It is an extraordinary honor to be recognized once again among Maryland’s Top 100 Women, especially as we celebrate 30 years of this distinguished legacy,” said Windsor. “I am deeply grateful to The Daily Record, the esteemed selection committee, and the past honorees whose leadership, mentorship, and service have paved the way for so many.”
As a retired US Armyofficer and former member of the federal Senior Executive Service (SES), Windsor has demonstrated exceptional leadership throughout her career. Under her guidance, Windsor Group LLC has become an award-winning professional services firm providing staffing, project management, IT support, and training solutions.
The company has achieved national recognition, including being ranked among America’s fastest-growing private companies and top corporate philanthropists. These awards include the Women Presidents Organization (WPO) 50 Fastest, the Institute for Veterans and Military Families – IVMF Vet100, and the Inc. Magazine Inc. 5000. Windsor has also been lauded in her own right, including being previously named as one of Maryland’s Top 100 Women in 2023.
The Top 100 Women Honoree program celebrates individuals making extraordinary contributions to their fields and communities. By recognizing Windsor, this award underscores her role as business leader and a champion for mentorship and diversity.
“This recognition is not just a personal milestone — it is a reflection of the collective strength and brilliance of Maryland’s women leaders who continue to break barriers, elevate communities, and create pathways for the next generation,” Windsor added. “I am humbled to stand alongside such remarkable women and inspired to continue paying it forward.”
A celebration honoring the awardees will be held at Towson University Arena on May 5, 2025.
For more information on Diedre Windsor and Windsor Group LLC, visit https://www.windsorgroup-llc.com/.
For more information about The Top 100 Women In Maryland and a Full List of the Honorees, visit https://thedailyrecord.com/event/top-100-women/
