Windsor Group LLC's meteoric rise from startup to multimillion-dollar business has fueled not only economic growth but also generosity—driving major contributions to nonprofits supporting veterans, military families, and underserved communities.
WASHINGTON, Nov. 12, 2025 /PRNewswire-PRWeb/ -- Windsor Group LLC, a woman and service-disabled veteran-owned professional services firm based in Bethesda, Maryland, has earned its fifth consecutive placement on the Inc. 5000 list of America's Fastest-Growing Private Companies. The Maryland-based government contracting firm ranked No. 1487 with 292% three-year growth, building on four prior top-500 appearances—No. 191 (2021), No. 368 (2022), No. 343 (2023), and No. 318 (2024). This recognition underscores Windsor's reputation as a dynamic, purpose-driven leader in the federal sector.
Since officially launching in 2017, Windsor Group LLC—founded by Detroit native and retired U.S. Army Major Diedre Windsor—has soared from $100,000 in its first year to $37 million in 2023, with total revenue surpassing $90 million year-to-date. The company has employed more than 260 professionals, engaged over 100 consultants, and subcontracted work to 40+ small businesses—pouring revenue back into their operations and fostering growth across the industry. Windsor's core services include program and project management, staff augmentation, IT services, and marketing and outreach—capabilities that have positioned it as a trusted partner to more than 16 federal agencies.
Each year, the Inc. 5000 list highlights independent businesses demonstrating exceptional growth amid challenging market conditions. Among the top 500 companies, the median three-year revenue growth reached 1,552%, collectively creating more than 48,000 U.S. jobs. For the full list and searchable company profiles, visit www.inc.com/inc5000.
"Making the Inc. 5000 is always a remarkable achievement, but earning a spot this year speaks volumes about a company's tenacity and clarity of vision," said Mike Hofman, editor-in-chief of Inc. "These businesses didn't just weather the storm—they grew through it. Their stories remind us that entrepreneurship remains the engine of the U.S. economy."
Among its most notable achievements, Windsor managed the U.S. Department of Agriculture's $2.2 billion Discrimination Financial Assistance Program (DFAP), which provided relief to farmers and ranchers who faced discrimination in USDA lending programs. The firm's leadership and execution during DFAP solidified its reputation for managing large-scale, high-impact programs efficiently and ethically.
"For me, this recognition is as much about people as it is about performance," said Diedre Windsor. "Our motto has always been 'Mission First, People Always.' Earning a place on the Inc. 5000 for five consecutive years reflects not just our business success, but the impact we've made on our employees, partners, and communities."
That community impact runs deep. Under Windsor's leadership, the firm has donated more than $600,000 to nonprofits supporting veterans, women, and underserved communities—including the Code of Support Foundation, Military Women's Memorial, Women Veterans Interactive Foundation, Institute for Entrepreneurial Leadership, Women Elevating Women, Sallie Eaton Benevolence Foundation, and the Williams Franklin Foundation. Windsor's sustained giving has earned the company a spot on the Washington Business Journal's Corporate Philanthropy list for three consecutive years (2023–2025).
In addition to the Inc. 5000, Windsor Group has been named to the Vet100 list of fastest-growing veteran-owned businesses (four consecutive years) and recognized by the Washington Business Journal as one of the Fastest Growing Companies in Greater Washington (2023 and 2024). The Women Presidents Organization has twice honored Windsor among the 50 Fastest-Growing Women-Owned and -Led Companies (2024 and 2025).
The story of Windsor Group is one of perseverance, purpose, and people. Under Windsor's leadership, the company has grown from a one-woman operation into a high-performing enterprise grounded in discipline, integrity, and service—values shaped by her military career and refined through years in federal leadership.
Windsor credits much of the company's success to its exceptional employees, whose work at client sites consistently demonstrates Windsor's value, and to the leadership team—including Vice President, retired Army Colonel Edna Cummings—whose guidance and partnership have been invaluable. Together, their shared veteran background fosters a "mission-first, people-always" mindset, a culture of excellence, and the accountability that drives Windsor's performance.
Today, Ms. Windsor is recognized as both a business leader and philanthropist, driven by impact and guided by purpose. As Windsor Group celebrates its fifth consecutive year on the Inc. 5000, the firm stands as proof that sustained growth and social responsibility can go hand in hand.
"We are building something larger than ourselves," Windsor said. "Our success is measured not just in dollars or rankings, but in the lives we touch and the opportunities we create."
Methodology
Companies on the 2025 Inc. 5000 are ranked according to percentage revenue growth from 2021 to 2024. To qualify, companies must have been founded and generating revenue by March 31, 2021. They must be U.S.-based, privately held, for-profit, and independent—not subsidiaries or divisions of other companies—as of December 31, 2024. The minimum revenue required for 2021 is $100,000; the minimum for 2024 is $2 million.
About Windsor Group LLC
Windsor Group LLC, founded in 2017 and based in Bethesda, Maryland, delivers professional services and business solutions to both 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, primarily federal agencies and including private enterprises.
About Inc.
Inc. is the leading media brand and playbook for entrepreneurs and business leaders shaping our future. Through its journalism, Inc. aims to inform, educate, and elevate the profile of its community: the risk-takers, innovators, and ultra-driven go-getters who are creating the future of business. Inc. is published by Mansueto Ventures LLC, along with fellow leading business publication Fast Company. For more Inc., please visit www.inc.com.
Media Contact
Edna Cummings, Vice President, Windsor Group LLC, 1 (240) 600-0149, [email protected], https://www.windsorgroup-llc.com/
SOURCE Windsor Group LLC
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