by Roz A. Gee
October 2, 2025
Diedre Windsor displays on her firm’s speedy income development and her legacy.
Diedre Windsor, founder and CEO of Windsor Group LLC, has led her firm to a fifth consecutive 12 months on the Inc. 5000 listing of America’s fastest-growing non-public firms.
Windsor Group is an award-winning skilled providers firm primarily based in Bethesda, Maryland. Windsor supplies best-in-class options to each private and non-private sector purchasers, figuring out areas of weak spot and serving to resolve difficult points to make sure optimum success and development.
Windsor helps its purchasers within the areas of program and challenge administration, skilled and technical staffing options, IT assist, coaching, and administration consulting. Windsor is a woman-, minority-, and service-disabled veteran-owned small enterprise, in addition to an SBA 8(a) Enterprise Improvement program participant and GSA A number of Award Schedules (MAS) contract holder.
BLACK ENTERPRISE caught up with Windsor to speak about her firm’s income development and Inc. 5000 listings.
Windsor Group simply landed on the Inc. 5000 listing of America’s Quickest-Rising Non-public Firms for the fifth consecutive 12 months—a milestone achieved by fewer than 1% of firms in Inc. 5000 historical past. How do you’re feeling about attaining this milestone?
Windsor: It means endurance. It means we’re doing one thing proper, hiring the suitable folks for the suitable initiatives, and paying the suitable wage to make sure a excessive retention charge. It’s actually about being constant and proving {that a} Black woman- and veteran-owned agency cannot solely survive however thrive in enterprise.
Stroll us via the size of Windsor’s development. What stands out most to you concerning the journey from $100,000 in 2017 to thousands and thousands immediately?
In our first 12 months, Windsor Group secured a contract for an government assistant place—basically a secretary function. Though I had simply left my place as a senior government within the federal authorities, I stepped in and fulfilled the function myself. For me, it was a primary contract that will give Windsor a previous efficiency document to construct on. That 12 months, 2017, we introduced in $103,000 in income. From that modest begin, Windsor grew to $37 million in 2023 and $25 million in 2024. Thus far, we’ve generated greater than $90 million in income on $95 million in prime contracts throughout 15-plus federal businesses. That development has allowed us to make use of over 260 professionals, interact 100-plus consultants, and 40-plus subcontractors, serving to them increase within the course of.
As a enterprise chief, what would you say is Windsor Group’s number-one precedence?
We’re a for-profit enterprise, so income—and, extra importantly, profitability—is essential. It permits us to maintain development, put money into our folks, and create alternatives for others. Each worthwhile contract creates a ripple impact that contributes on to the economic system: extra revenue circulating in households, better stability in communities, and long-term development for different entrepreneurs.
What’s your message to those that wish to construct a enterprise of actual worth however don’t see themselves as innovators, creators, or celebrities?
My message is straightforward: you don’t should be identified, widespread, or invent the subsequent large factor to construct one thing significant. Service-based companies are the spine of the economic system. Windsor Group doesn’t create content material or promote merchandise, and we’re not nationally identified. We offer a full suite {of professional} providers, together with staffing, IT providers, and advertising, that organizations depend on each day. In doing so, we’ve created lots of of jobs, supported dozens of small companies via consulting and subcontracting alternatives, and contributed hundreds of {dollars} to charitable causes.
Windsor has managed a number of the authorities’s most high-profile applications, together with USDA’s Discrimination Monetary Help Program. What did this challenge train you about working at scale?
DFAP was a turning level for Windsor. It was a $2.2 billion program offering reduction to farmers and ranchers who had confronted discrimination in USDA lending. Accountable for the whole East Coast, we opened 21 places of work throughout 27 states, Puerto Rico, and the U.S. Virgin Islands—all inside 45 days. That meant including greater than 70 Windsor workers, managing over 300-plus workers on the program’s peak, and coordinating quite a few subcontractors. The expertise taught us the worth of sturdy infrastructure—executing agreements on time, guaranteeing well timed invoicing, confirming insurance coverage, and totally vetting hires. DFAP pushed us to a scale we had by no means tried, proving that success requires not simply agility and logistics, however disciplined programs and unwavering belief in your staff.
You talked about subcontracting work to greater than 40 small companies. Why is that this vital?
I usually say, if you wish to assist one other small enterprise, put income into their enterprise. We associate when it is smart for the challenge and to display to purchasers our means to construct capability and ship at scale. Additional, I’m a agency believer in lifting others as we climb. Subcontracting strengthens the ecosystem, not simply our personal firm. After we work collectively, we ship higher outcomes, create alternatives, and strengthen the general market.
Windsor is well-known for its philanthropy within the better Washington, D.C. space, having been acknowledged on Washington Enterprise Journal’s “Prime Company Philanthropist” listing three years in a row. Why is giving a precedence for you?
Philanthropy provides my work a better sense of function…and it’s my ardour. There are such a lot of nonprofits doing the arduous work of bridging the hole between what the federal government supplies and what communities really want. Thus far, Windsor has donated greater than $600,000 to charitable organizations supporting veterans, ladies, and underserved communities through teams just like the Code of Help Basis, Ladies Veterans Interactive Basis, and the Williams Franklin Basis.
You’ve spoken usually about legacy. What sort of legacy are you constructing—not only for your self, however to your workers and group?
I need Windsor Group LLC to be often known as an organization that takes care of our workers, delivers affect to our purchasers, creates jobs, empowers fellow small companies, and offers again generously. When my workers can purchase properties, when our subcontractors develop stronger, when nonprofits increase their attain due to our assist—that’s legacy.
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