Windsor Group Achieves Fifth Consecutive Year on Inc. 5000 List
Diedre Windsor, founder and CEO of Windsor Group LLC, has led her company to remarkable success. The Bethesda-based professional services firm earned a spot on the Inc. 5000 list for the fifth consecutive year. This milestone places Windsor Group among fewer than 1% of companies in Inc. 5000 history.
Windsor said, “It means staying power. We’re doing something right, hiring the right people, and paying fair wages to ensure high retention. It shows a Black woman- and veteran-owned firm can not only survive but thrive.”
The recognition highlights Windsor Group’s consistency and long-term growth in professional services.
From $100,000 to $90 Million in Revenue
Windsor Group started in 2017 with $103,000 in revenue from a single executive assistant contract. Diedre Windsor personally fulfilled the role while building the company’s first performance record.
Since then, the firm’s growth has been exponential. Revenue reached $37 million in 2023 and $25 million in 2024. To date, Windsor Group has generated over $90 million from $95 million in prime contracts across more than 15 federal agencies. The company now employs more than 260 professionals, 100 consultants, and over 40 subcontractors.
Windsor emphasized, “Every profitable contract creates a ripple effect—more income for households, stability in communities, and long-term growth for other entrepreneurs.”
Focus on People, Profitability, and Purpose
Windsor Group prioritizes profitability and growth while creating opportunities for others. The company provides program and project management, IT support, staffing, and management consulting for public and private clients.
Diedre Windsor said, “Service-based businesses are the backbone of the economy. You don’t need to be famous or invent the next big thing to build something meaningful.” Windsor Group has created hundreds of jobs, supported small businesses, and donated thousands of dollars to charitable causes.
Managing High-Profile Government Programs
A turning point for the firm was managing USDA’s Discrimination Financial Assistance Program. The $2.2 billion program assisted farmers and ranchers facing discrimination. Windsor Group opened 21 offices across 27 states, Puerto Rico, and the U.S. Virgin Islands within 45 days.
The project added over 70 employees and coordinated 300-plus staff and subcontractors. Windsor said, “Success requires agility, logistics, disciplined systems, and unwavering trust in your team.” This experience prepared the firm to deliver at scale.
Supporting Small Businesses Through Subcontracting
Windsor Group works with more than 40 small businesses on contracts. Windsor explained, “If you want to help another small business, put revenue into their business. Partnering strengthens the ecosystem, creates opportunities, and delivers better outcomes.”
Subcontracting allows Windsor Group to expand capacity while empowering other companies to grow and succeed.
Commitment to Philanthropy and Legacy
Windsor Group has been recognized three times on Washington Business Journal’s “Top Corporate Philanthropist” list. The firm has donated over $600,000 to nonprofits supporting veterans, women, and underserved communities.
Windsor shared, “When employees buy homes, subcontractors grow stronger, and nonprofits expand their reach, that’s legacy. I want Windsor Group to be known for impact, empowerment, and generosity.”
