Small Business Spotlight: How Diversity Connected Helps Companies Turn Chaos into Clarity

For more than two decades, Sara Gregory has been the head of Diversity Connected, a boutique consulting firm that specializes in operational excellence, project management, event execution, and data analytics.

Over that time, the company has grown into a trusted partner for Fortune 500 companies, startups, and government agencies alike. And while it’s seen tremendous success, the idea started with a simple inconvenience.

While working as a junior analyst at IRI, a leading data and analytics company, Gergory noticed that many client requests for short-term engagements were routinely dismissed by her firm and its competitors.

“Sometimes clients would call with short-term projects – too short for firms to take seriously,” said Gregory. “But I loved those types of engagements. I liked that things changed quickly. I didn’t enjoy corporate America’s predictability and doing the same thing every day.”

Encouraged by two mentors at IRI – and with a list of clients whose contracts weren’t being renewed – she made the leap.

Sara Gregory

“I quit on a Wednesday and had my first client by Monday. By the end of that week, I had 15 clients,” she said. “At the time, I thought that was normal. It wasn’t.”

“Saying yes to everything at the beginning forced me to learn fast,” she added. “I knew how to work in a business, but not how to work on the business. That part I had to learn through trial by fire.”

Diversity Connected first made its mark by helping major retailers and smaller suppliers understand and adapt to each other.

“Back when large retailers began working with small suppliers, many didn’t know how to do business with each other,” she explained. “We created checklists, documented onboarding protocols, and helped them meet expectations that were previously out of reach.”

The firm’s reach soon expanded. From helping businesses understand consumer loyalty gaps to executing brand activations at Historically Black Colleges and Universities, Gregory and her team have worked to translate data into action and strategy into results.

“It doesn’t stop with the data,” she said. “Sometimes the problem is something the data solves, sometimes it’s an event or communications issue. Clients hire us to be firefighters – we help put the problem out.”

Yet, despite her success, Gregory hit unexpected roadblocks in recent years—not because of performance, but because of perception.

“With our name alone — Diversity Connected — we are getting flagged. Clients are making assumptions and playing it ‘safe,’” she said.

“But we’re not a DEI company – we’ve been successful because of our results. We’ve always just done the work,” she said. “Now, people see us through the lens of ethnicity and gender instead of the value we bring.”

Rather than retreat, Gregory doubled down on purpose.

She recently formalized a mentorship program she had long offered informally to women in her community.

“I launched the ‘Auntie Series’—a four-year program for women who’ve had businesses for five years or less,” she said. “I help them sustain through political and funding shifts. A lot of young women want to start businesses, but they need someone to show them how to navigate the system.”

That clarity of purpose is what brought Gregory to the Polsky Exchange and the Polsky Center’s Small Business Development Center (SBDC). Over the past 18 months, she’s worked closely with the team to revamp her website, sharpen her marketing materials, and prepare her business for a move into government contracting.

“I came in with a vision, and they helped me bring it into focus,” said Gregory. “SBDC Director Vince Beachum looked at every part of the business and helped me see what needed to change.”

Diversity Connected is now also part of the Polsky Exchange’s Small Business Growth Program, which helps startups grow by providing a team of highly-skilled University of Chicago graduate students to provide hands-on consulting, helping them address key business challenges and determine new strategies for business growth.

“From where we were to where we are now – it’s night and day,” she said. “The Polsky Center has been phenomenal. And what I tell my clients is the same thing Polsky told me: Tell me where you want to go, and I’ll help get you there.”

Gregory now has a capability statement, knows how to optimize her online presence for agency procurement, and is better equipped to pursue state and local government contracts — her next major goal.

“We’re targeting the state and county level. That’s where I see us thriving,” she said.

Follow Diversity Connected on Instagram @DiversityConnected and Facebook @DiversityConnected.

The Small Business Spotlight series highlights South and West side business that have taken part in the Polsky Exchange’s Small Business Growth Program. Learn more about these exceptional businesses.