Recording live from the WPO Entrepreneurial Excellence Forum, Money Movers hear from Diedre Windsor, President and CEO of Windsor Group, LLC, one of the 50 fastest-growing women-led companies at WPO. Based in Maryland, Windsor Group is an award-winning professional services company that provides services to public and private-sector clients. Talking points include what a career in the Army taught her about entrepreneurship, supporting her community and uplifting other women of color, and how to find success with public sector and government contracts.

Key Insights & Timestamps:

[00:00]: Podcast begins
[02:39]: Inspiration for Army enlistment & early career motivations from a single mom
[04:57]: Leaving a government job & embracing discomfort with entrepreneurship
[10;49]: Keeping the Windsor Group path when struggling with revenue
[12:20]: Struggles & successes of working with government contracts with your company
[19:51]: Philanthropic business honors & the importance of giving back to Detroit
[23:12]: BOW of the Year & why supporting women entrepreneurs of color matters to Diedre
[30:02]: Dreaming bigger & building something tangible for the future

Guest Spotlight:

Diedre Windsor, President and CEO of Windsor Group LLC

Diedre L. Windsor is the founder of Windsor Group LLC. Ms. Windsor, a native of Detroit, enlisted in the US Army in October 1986. As a military officer, Diedre’s assignments spanned from Kunsan, South Korea to Riyadh, Saudi Arabia and back to Fort Bragg, North Carolina where she served in a myriad of leadership roles until she retired from active service in September 2009 as a Major.

Upon retiring from the Military, Diedre continued along her public service path by joining the federal government. She assumed roles at the U.S. Department of Education first as Chief of Staff to the Federal Student Aid Chief Information Officer and Technology Office and later as Executive Officer and Director of Resources for the Officer for Civil Rights. After five years at Education, Diedre joined the career Senior Executive Service (SES) with the Department of Justice (DOJ).

Diedre left the federal government in late 2016 to pursue entrepreneurship full time. Her company, Windsor Group, LLC, provides a host of professional services and business solutions to public and private sectors. The company’s core services include, Staffing, Training, IT Support and Project Management.

Key Takeaways:

Leaving a comfortably paying government job for the world of entrepreneurship wasn’t an easy decision, especially when revenue and success were a hard fight for Windsor Group in its infancy. “I did jobs most people wouldn’t do,” Diedre says when explaining Windor’s first government contracts. “To make sure all the bills are paid, that was good enough for me.”
Honored as one of the top philanthropic businesses for the Detroit metro area, Diedre says that Windsor Group prioritizes philanthropy and community support as much as companies twice or three times their size. Being able to give back is one of the biggest highlights of Windsor Group for Diedre, who believes in supporting the work of organizations and individuals deeply involved in communities across the US. “There are people with boots on the ground doing the real work. Why not help those people, those organizations?”

Resources Mentioned:

Windsor Group LLC | windsorgroup-llc.com, The BOW Collective | thebowcollective.org, WPO | women-presidents.com

Connect with Diedre:

For More Information:

Produced by Speakerbox Media. Visit youtube.com/@StaciLaToison for more episodes, detailed show notes, and access to additional resources.

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Winning Private & Public Contracts with One of WPO’s 50 Fastest