Graphic with text: Meet Windsor Group LLC CEO Diedre Windsor: from Mission to Millions

Meet Windsor Group LLC CEO Diedre Windsor:

from Mission to Millions


Diedre Windsor’s diverse professional journey from military service to entrepreneurship exemplifies the transformative power of collaboration, resilience, and leadership. Starting with just an idea and an EIN in 2010, followed by a six-year detour, Diedre is now President and CEO of Windsor Group LLC, which ended 2023 with over 50 active contracts across 12 clients and $34.4 million in revenue. Providing government agencies with professional services and business solutions, Windsor Group LLC has grown from Diedre’s passion for supporting others into a company of over 100+ employees, all working towards the common goal of understanding the mission and challenges facing federal organizations and providing tailored support.

We spoke with Diedre to hear more about this journey and to understand the firsthand experience of watching an idea grow into success. Her unique story provides insight and inspiration for how anybody can pursue their ambitions through perseverance, integrity, and connecting with others through invaluable support networks like WBEC Metro NY & Greater DMV, Women President’s Organization, C200, Veterans Institute for Procurement and The BOW Collective.

The winding road to entrepreneurship

“Sometimes it's not a dream denied — it’s a dream deferred.”

In 2010, Diedre knew she wanted to start her own business and registered for an EIN. But being freshly out of the military and working to transition back into everyday civilian life, she acknowledged that she wasn’t yet in the headspace for entrepreneurship and instead began work in the federal government. This marked the beginning of a significant chapter.

From 2010 to 2016, she served in various roles within the federal government, including a senior executive service position at the U.S. Department of Justice. During this period, Diedre honed her leadership skills, cultivated valuable relationships, and gained insights into the intricacies of government operations and contracting.

It set the foundations for what is now Windsor Group LLC.

Drawing from her tenure in the military and government, Diedre recognizes the importance of a collaborative team, fostering inclusivity, and upholding values of integrity and loyalty. She embraced the role of an entrepreneur with a clear vision and purpose. She says, “I think that it’s important for people to know that sometimes it is not a dream denied; it’s a dream deferred. I truly believe things happen when they’re supposed to happen.”

Windsor Group LLC provides professional services primarily to federal government agencies, focusing on understanding and addressing organizational challenges. They leverage Diedre’s extensive federal government experience and emphasize building strong relationships with clients, cost-effectiveness, flexibility, and a comprehensive vetting process for human resources. Their client roster includes the U.S. Department of Veterans Affairs, Health and Human Services, National Science Foundation and the US Department of Agriculture. Windsor prides itself on being 98% prime to the federal government.

Leading with integrity and building influence

Integrity is truly at the heart of everything Diedre and Windsor Group LLC do. It serves as the cornerstone of their ethos, infusing teamwork, client service, and every decision made. Diedre believes everyone leads from where they are, and therefore, at Windsor, leadership emanates from all levels of the organization, emphasizing collective responsibility for upholding ethical standards. This inclusive approach fosters a culture where integrity isn't just preached but practiced daily. Clients trust Windsor Group because integrity is woven into every service, recommendation, and solution provided.

Transitioning from the structured hierarchy of the military to the professional world, Diedre emphasizes that leadership revolves around empowering others to reach their objectives. As a Black woman, she acknowledges the absence of instant authority based on rank. She explains “We don’t walk in the door with the instant credibility/clout, regardless of our rank. We have to prove ourselves – we have to build influence to get people to do what we need them to do, which, ultimately is more sustainable over time.”

Overcoming challenges and staying motivated

“I want to be a person that inspires others.”

Of course, Diedre’s entrepreneurial journey was not without its difficulties. Navigating the entrepreneurial landscape as a Black woman meant facing biases and dismissiveness while also confronting the complexities of business development in male-dominated environments. Despite her impressive credentials and undeniable expertise, Diedre has found herself underestimated or her authority questioned because of her gender and race. Yet, in these instances, she says she doesn’t get angry; instead, she focuses on showing up in excellence. In her own words, “My mantra is — understand who you are and what that means when you walk into a room and operate with that knowledge. You can’t control people’s preconceived notions. You can only control how you show up in the world.”

Diedre also hasn’t faced these challenges alone. Her journey has been deeply intertwined with other women business owners as well as her involvement in support networks like WBEC Metro NY and Greater DMV, Women Presidents Organization and The BOW Collective, which played a pivotal role in her entrepreneurial journey, providing valuable resources, mentorship, and networking opportunities.

In explaining the importance of these networks, Diedre recalls how, for years, she was inspired by the story of Kathryn Freeland, CEO of A-TEK, and had bookmarked her story to stay motivated. Years later, after Diedre stood to ask a question during a women’s conference, to her surprise, at the end of the session, Kathryn walked up and gave Diedre her business card. This story brought Diedre full circle and remains with her as an example of the impact someone can have on motivating another and the importance of sharing one’s story.

“I want to be what Kathy Freeland is to me, to somebody else,” Diedre shares. “I want to be that person that inspires somebody else or shows them that you can do this. You can do these things, and it’s not about the money. It’s about being able to impact lives.”

Driving success through collaboration

Diedre’s journey exemplifies the transformative power of collaboration and partnership. By leveraging her military background, government experience, and entrepreneurial spirit, she cultivated a thriving business that serves both the public and private sectors. Through Windsor Group LLC, Diedre remains committed to making a positive impact, solving complex challenges, and empowering others to achieve their goals. She urges, “We must broaden our perspective on collaboration. Support can be as simple as sharing knowledge and skills or even just lending a listening ear.”

Studies show that female business owners often reinvest more into their communities compared to their male counterparts, contributing to the elevation not only of their ventures but of the entire ecosystem around them. Diedre is a perfect example of this. As Windsor Group LLC continues to grow and evolve, Diedre expands her scope, too. Last year, her company gave $280,000 to charities such as the Women Veterans Interactive Foundation, Military Women’s Memorial, Institute for Entrepreneurial Leadership, Black Art Today Foundation, and Code of Support Foundation, among others. Diedre is proud that this culture of giving will only grow as the company does and envisions a future where the company serves as a catalyst for positive change, driving innovation and empowering women-owned businesses. With her unwavering determination and commitment to excellence, Diedre is poised to amplify success and inspire others to pursue their entrepreneurial dreams.