VBE Spotlight: Windsor Group, LLC

Windsor Group LLC, founded in 2017 and based in Bethesda, Maryland, is a dynamic, woman-owned, minority-owned, and service-disabled veteran-owned small business that delivers exceptional professional services and business solutions to the public and private sectors. Specializing in staff augmentation, program and project management, IT support, marketing, outreach, technical assistance, and case management, Windsor Group consistently provides top-tier solutions to a diverse range of clients, including federal agencies and private enterprises. The company proudly holds various certifications, including WBE, MBE, DBE, SBE, 8(a), SDVOSB, and EDWOSB. Windsor Group holds a GSA Multiple Award Schedule and the OASIS + contract vehicles. 

Federal Government (Across 10 agencies)

GDIT

Analytic Acquisitions

Diedre conceived the idea for Windsor Group in 2010, shortly after retiring from the military. While she secured an EIN at that time, she wasn’t mentally prepared to fully commit to entrepreneurship. Instead, she took a government job, seeking the stability she needed. It wasn’t until January 2014 that she officially registered the business in Maryland, though she still wasn’t ready to make the leap. After years of working in a structured environment, the idea of leaving a steady job was daunting. However, in November 2016, Diedre made the bold decision to leave the workforce and dedicate herself 100% to building Windsor Group. She saw a significant opportunity to address the challenges organizations face in human resources, staffing, and organizational development, believing that innovative solutions in these areas could make a meaningful impact.

Some of the key challenges Diedre faced in getting Windsor Group started included finding contracts that didn't require extensive experience, which can be a major barrier for new businesses. Additionally, securing the necessary capital to fund contracts posed another significant challenge. With limited financial resources, it was difficult to ensure the company could meet the demands of larger projects. Another obstacle was overcoming the perception that success in government contracting was only achievable for large businesses. Diedre had to prove that a smaller, more agile company could provide high-quality services and bring innovative solutions to the table, despite the common assumption that size equated to success.

"The key to Windsor Group LLC’s success lies in Diedre's commitment to building a company rooted in strong values, agility, and adaptability. Early on, Diedre recognized the importance of partnering with other businesses, which fostered valuable collaborations and opened doors for new opportunities. She also made the strategic decision to never overlook smaller contracts, understanding that even modest projects could lead to long-term growth. One of the most pivotal moves was investing in a skilled proposal manager, even when the company couldn’t afford it. This decision, made through sacrifice, proved invaluable in securing key contracts and setting the stage for Windsor Group’s success.

While many small businesses are advised to build relationships and seek subcontractor opportunities, Windsor Group chose to prioritize bidding on contracts directly and often. They didn’t shy away from taking on the role of prime contractor, confidently stepping into larger opportunities. By staying agile, adaptable, and committed to doing what they say they will do, Windsor Group has been able to consistently deliver on their promises, build trust, and achieve steady growth."

- Revenue is your best source of capital. One of the most important lessons I’ve learned is that your revenue is the best form of capital. It’s crucial to save as you grow so that when you need funds for things like payroll or unexpected expenses, you’re prepared. Financial discipline has been key in ensuring the business can weather any storm.

- Small contracts matter – Early on, I realized that many businesses overlook smaller contracts, but I’ve always believed that revenue is revenue. Small contracts can lead to long-term relationships, new clients, and valuable learning experiences. I never underestimate the value of these opportunities.

- Know your financials – Understanding your numbers is critical to the health of your business. I keep a close eye on my margins because they directly impact profitability. Knowing where the money is coming from and where it’s going helps me make informed decisions and stay ahead of potential financial challenges.

- Do what you say you’re going to do – Reputation is everything. I make it a point to always follow through on my commitments. If I’m not equipped for a particular job, I don’t take it on. It’s always better to be transparent about my capabilities than to overpromise and underdeliver, which can hurt the business in the long run.

- Hire slow, fire fast – Building a strong team is essential. I take my time when hiring, making sure the individuals I bring on align with the company’s values and needs. However, if someone isn’t the right fit, I’ve learned not to hesitate to part ways quickly. Holding onto the wrong person can slow progress and negatively affect the company culture.

- Trying to do everything yourself – You can’t do it all. Build a strong team, delegate, and trust others. Doing everything yourself limits growth potential.

- Chasing after every opportunity – Not all opportunities are a good fit. Focus on contracts that align with your strengths to avoid spreading your resources too thin.

- Relying too heavily on set-asides – Don’t rely solely on set-asides. Build a strong proposal team to compete effectively for competitive contracts.

- Neglecting cash flow – Cash flow is crucial. Even with strong revenue, poor cash flow management can put your business in a tough spot.

- Underestimating relationships – Build and nurture strong relationships with clients, partners, and your team. They are key to long-term success.

- Failing to diversify – Diversify within your sector, such as across different government agencies, but also across sectors. While Windsor Group is 100% focused on government, we’ve recognized the need to expand into the commercial and state/local markets for greater resilience and growth.

- Failing to adapt – The business world changes constantly. Stay flexible and willing to adapt to new challenges to keep your business relevant.

As a proud U.S. Army veteran and former Senior Executive Service member, my journey from public service to entrepreneurship has been guided by a deep commitment to purpose, performance, and impact. Windsor Group LLC has grown into a nationally recognized, award-winning firm. Over the past three years, we’ve achieved an average revenue growth of over 100%, earned four consecutive appearances on both the Inc. 5000 and Vet100 lists, and led the successful execution of USDA’s $2.2 billion Discrimination Financial Assistance Program.

Equally important to me is Windsor’s role in empowering others. We’ve strategically subcontracted with over 30 small businesses—many veteran- and women-owned—helping them build capacity, grow their revenue, and break into new markets. I also prioritize philanthropy, having contributed over $20,000 annually for the past two years to nonprofits that serve veterans, women, and underserved communities.

To the NaVOBA community: I’m proud to stand with you. Our collective success not only strengthens our businesses, but also builds lasting economic power for veterans, families, and future generations.