Diedre L. Windsor

Daily Record Staff//May 9, 2023

Diedre L. Windsor

By Daily Record Staff

//May 9, 2023

Diedre L. Windsor

Founder and Chief Executive Officer
Windsor Group LLC

Your career has been divided into two very distinct halves – a public sector segment and a private sector path, culminating with your current successful entrepreneurial endeavor. How did it all begin?

I enlisted in the US Army Finance Corps in October 1986. My early assignments as a finance soldier include Neu Ulm, Germany and Fort Bragg, North Carolina where I served as a paratrooper with the elite 82nd Airborne Division. In 1992 I was awarded an Army Green to Gold Scholarship resulting in my transition from the enlisted to officer ranks. I was commissioned a Regular Army Air Defense Artillery (PATRIOT Missile) Officer and later transitioned to the Adjutant General Corps (Personnel). As a military officer, my assignments spanned from Kunsan, South Korea to Riyadh, Saudi Arabia and back to Fort Bragg, North Carolina where I served in a myriad of leadership roles until I retired from active service in September 2009 as a Major.

Describe your achievement as head of Windsor Group that makes you particularly proud

There was a five-year time span where we just grew exponentially. In 2021, with over 2,225% growth, Windsor debuted at #191 on Inc. Magazine’s Inc. 5000 list of America’s Fastest-Growing Private Companies and just recently was named to the fifth annual Vet100 list which celebrates the top 100 Veteran Owned and Operated businesses from the annual Inc. 5000 rankings.


This is an honoree profile from The Daily Record's Top 100 Women awards. Information for this profile was sourced from the honoree's application for the award.


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