Taking Over For Her Dad and Shaping the Family Business

Kelly Webb Roberts

What Drives Her: Kelly Webb Roberts, President of Webb Auto Group.

Growing up, Kelly Webb Roberts always had nice cars.

When you grow up with your dad owning a dealership, you tend to drive new cars. But Kelly drove “REALLY nice cars in college: the Ford Thunderbird, a Chevy Blazer in winter, and a number of Corvettes. “When I was in college I made good grades and was awarded some scholarships,” Kelly said. While she was worrying about her grades, Dad took care of transportation by making sure she drove great cars. “In hindsight, it was kind of ridiculous,” she said.

But after she graduated,  Kelly decided not to follow her dad into the family business at the Webb group of auto dealerships, and the flow of new cars stopped.

Was her dad disappointed? Well, he “quit supplying me with nice cars while I was working with accounting firms,” and she had to buy her own car, not nearly as nice as the fully loaded models she was used to. “He never pressured me to join the family business, but he sent a pretty clear message,” she laughs.

As it turns out, not going to work for her dad was a good thing. Kelly graduated Cum Laude with a bachelors of business administration in accounting and finance from St. Mary’s College in Notre Dame. She went on to earn her Master’s degree in accounting from Loyola University Chicago before working for accounting firms specializing in auto dealerships, where she did a lot of work with publicly traded companies. “I’m grateful that I got to work with publicly traded groups. It helped me see their processes and businesses,” says Kelly.

Kelly Webb Roberts

Creating balance in the dealerships includes giving back to the community. Webb Chevrolet helped the Plainfield girls baseball team get off on the right foot. Photo: Webb Chevrolet

The Perfect Time to Join the Family Business: Right Before the Recession

Ultimately, Kelly decided to join the family business as the third generation of management; she joined in 2006 – right before the Great Recession.

“I came into the business at a time when it was challenging, but I think that made me more disciplined,” she recalls. “I took over a store that needed attention. It was a store where no family member was working. And when it’s your own store, you care a little more.”

Kelly was charged with getting the store on the right path just as the economy was backsliding. “It was a scary time and we didn’t know if we would succeed.” But she was armed with the right stuff: a dedication to the family business and insight into other auto dealerships as well.

But more help was needed; her sister and brother joined the business, and Kelly also asked her husband, whom she had met in her public accounting days, to join the company, too. “I told him I needed his help, I needed someone I could trust.”

Under Kelly’s leadership, the company has experienced fueled growth and today it’s thriving, with several new acquisitions in the last few years.

Kelly Webb Roberts

Kelly with the new Chevrolet Equinox. Photo: Scotty Reiss

Changing the Automotive Business From the Inside Out

A native of Northwest Indiana, Kelly is the president of the Webb Auto Group and co-owner of Webb Chevrolet Plainfield and Oak Lawn, Webb Hyundai in Highland, Indiana, and Webb Hyundai Mitsubishi in Merrillville, Indiana. She was elected to the Chicago Automobile Trade Association (CATA) board of directors last year.

Growing the family business means constantly seeking to improve it—especially as it pertains to women, both her customers and her employees. Kelly is continually seeking ways to help Webb employees obtain the life and work balance we all need.

Looking at the business from a woman’s perspective and from a mom’s perspective, Kelly often sees things and thinks, “well, this has to be done differently.” As a result, she has implemented changes over the years to streamline operations and improve the customer experience. “I’m looking more at what makes our employees happy—what makes things easier for them.” Because if they are happy, they’ll make customers happy, too.

“For my first 5 to 7 years we were in growth mode and I was just trying to get my arms around everything,” says Kelly. “Now one big initiative is the focus on changing the traditional structure of sales. The traditional sales structure requires sales people to work from bell to bell and every Saturday. That’s a difficult schedule for mothers,” says Kelly. “I’m looking at ways to make this better, not just for women but for all sales people.”

What’s it Like Working For Dad?

Kelly’s dad still works at Webb Ford in Highland, Indiana. His dad and uncle were also in the business and mentored him when he was starting out. So “I thought I would have a lot more oversight, but Dad doesn’t micro-manage,” says Kelly. “He allows me to make my own mistakes which is the best way for me to learn.”

But she seeks out his advice and coaching; they have daily phone calls at 10:00am to keep up with what’s going on. She feels very lucky to be able to work independently within the company, too.

“People often ask how I can work with so many family members,” she says. “But it’s not like we’re sitting next to each other in cubicles all day. We all have our responsibilities and we make it work.”

Shaping the Fourth Generation of Webb Auto Group?

Kelly’s first car was a 1998 Mustang Convertible, and as it turned out, a great thing: the Mustang and the cars that followed helped her develop a love for cars and the family business. It’s a love that she hopes to pass on to her two daughters, ages 7 and 4, who help her to see the true needs of the dealership and its employees. 

Helping her daughters find a sense of balance–and appreciation for their accomplishments– is important to Kelly, but she knows they have to discover it on their own. “When my two daughters are old enough to drive, they’ll be driving something more reasonable [than she did] and pay for their own leases.”

Spoken like a sensible mom, and a sensible leader.

Journalist, entrepreneur and mom. Expertise includes new cars, family cars, 3-row SUVs, child passenger car seats and automotive careers... More about Scotty Reiss