The Heel: A good fit for Ashwaubenon

Kat Halfman

Past Contributor

January 27, 2023

ASHWAUBENON – Troy Dempsey, owner of The Heel Shoe Fitters, said he got his start in the shoe business in 1999 while looking for a summer job to support his ongoing degree in aviation maintenance.

Dempsey said he got a job at Trade Home Shoes, a national chain, where he worked for the next 10 years, climbing the company ladder.

“I found myself at a crossroads – continue there, or leave and do my own thing,” he said. “I made the decision to either start my own store or take over something that already existed.”

Dempsey found The Heel Shoe Fitters in downtown Green Bay and said it appealed to him immediately.

“Green Bay is close to where I’m from in the Upper Peninsula of Michigan, so it gave me a good spot,” he said.

At that time, The Heel was owned by Bob Sanderson, who Dempsey said he approached with a proposal to become business partners.

“He was a bit reluctant to partner…,” he said. “But I was persistent over the course of a year, and eventually he called me and said, ‘Okay, what do you have in mind?’”

Dempsey said he and Sanderson became partners in 2009, with the intention of eventually transitioning Dempsey as sole owner.

He said they worked together until 2012 when Sanderson retired, and Dempsey fully took over.

Troy Dempsey

A decade later, Dempsey’s efforts to set himself and the store apart were recognized – being named 2022 Retailer of the Year by the National Shoe Retailers Association.

The award highlighted Dempsey’s years of work climbing the industry ladder and fostering manageable growth for his business – growth he said came with many ups and downs, including a global pandemic.

Changing Industry
Dempsey said internet sales turned the retail industry on its head.

“The reality is the internet has changed everything, and in our case, the biggest impact on us was when we started competing with our own vendors,” he said. “The brands we buy from now have their own direct-to-consumer websites, so we had to set our store apart.”

Which Dempsey said the store did with a slant on foot health.

When The Heel first opened in 1970, Dempsey said it specialized in leather goods, and slowly transitioned toward more mainstream footwear.

“Before I came in, Sanderson had started to focus on foot health and comfort, because he knew that was a niche,” he said.
Dempsey said he took that one step further.

“I went to Northwestern University in Chicago to become a board-certified pedorthist, and now we specialize in foot, knee and back-related issues,” he said. “When you’re looking for orthopedic shoes, you don’t want to order a bunch online and end up sending them all back. You’d much rather go somewhere with well-trained staff.”

Dempsey said though The Heel found its niche in foot health and comfort, it isn’t all it offers.

“We do have to be careful because if we advertise ourselves that way too much, people might think we’re only an orthopedic shoe store,” he said. “We also sell fashionable shoes.”

Unique experience
Since its beginning, Dempsey said customer service has also been an essential aspect of The Heel’s success.

“It’s easy for people to say customer service, but ours is about offering a full experience,” he said. “Whether that be walking in the store and seeing how spacious it is, what a wide selection we have or how our staff treats customers.”

Dempsey said the store has a floor coordinator, who they internally refer to as “our quarterback,” who manages the flow of customers with an iPad.

“(The quarterback) identifies which salesperson would best connect with each customer,” he said. “We curate an individual experience for each customer, as well as the foot health stuff.”

The Heel Shoe Fitters have five board-certified pedorthists on staff. Submitted Photo

Including Dempsey, there are five board-certified pedorthists on staff at The Heel – he said they never upcharge for their pedorthic services.

Between 2012 and 2016, Dempsey added 13 people to his staff, including a full-time shoe cobbler.

In addition to the store’s foot-health focus, Dempsey said there is more that sets it apart.

“The vastness of good quality product you can’t find anywhere else distinguishes (The Heel),” he said. “In fact, we travel to Europe – Italy and Germany – and we meet with companies there that don’t have distribution in the U.S.”

Since relocating from downtown Green Bay to its current location at 930 Waube Lane in Ashwaubenon in 2016, Dempsey said The Heel has also been able to expand parking and add an outlet store for more budget-friendly options.

“I love downtown, but we looked at different locations there and nothing was a good fit for our ability to have long-term growth, including having the kind of parking a business like ours needs, especially when a big part of our business is focused on more foot health,” he said. “You don’t want somebody to have to walk from a block away if they’re older and having foot health issues. Now… we have handicap spots right (by the door) – no curbs to walk over, and the entrance is wheelchair accessible.”

COVID-19 pandemic
The COVID-19 pandemic disrupted business worldwide, and though The Heel wasn’t immune to those disruptions, Dempsey said he is proud of how the store handled it.

“I think we managed to keep our employees safe and create an environment our customers felt comfortable coming into,” he said. “The first month was certainly a little rough because we weren’t sure what was going to happen, exactly. I kept everyone on staff and paid them out for the month while we were closed, and some people continued doing backend work like online and phone sales, and we tried to keep the wheels on a skeleton crew.”

Once in-store shopping returned, Dempsey said his team followed COVID-19 protocols conscientiously.

“We followed those deliberately, and that was important to us because we’re not the kind of business where you could open the doors with three or four employees,” he said. “It doesn’t function with the skeleton crew, so we needed to make sure everybody was safe – we probably erred on the side of safety.”

Owner Troy Dempsey said the store has an inventory of more than 40,000 pairs of footwear. Submitted Photo

Despite the uncertainty the pandemic brought, Dempsey said it provided a unique opportunity to reassess his management strategy.

“It did give us an opportunity to reevaluate a lot of different parts of our business,” he said. “When you’re in the moment, you don’t always get a chance to see, but when everything slows down… we had a better pulse on what we had.”

Proudest moments
Dempsey said that despite some inevitable loss of business due to the pandemic, business has remained relatively steady over the years.

In 2019, The Heel was recognized by the Greater Green Bay Chamber of Commerce with the Business Growth Award, something he said he is proud of.

“From when I first entered this business, we’ve grown by a multiplier of more than 50 times – we’re at around 48 employees now,” Dempsey said. “In the last couple of years, we’ve added health insurance, a 401K program for everyone and additional benefits, which is another one of the things I’m most proud of.”

More recently, he said being named 2022 Retailer of the Year was “the highlight of his career.”

Dempsey said he also does what he can to give back to the Greater Green Bay community.

“We have a good track record of donating to nonprofits, and our main focuses are poverty, mental health and homelessness, partly because my fiancée works with Habitat for Humanity,” he said. “We’ve also sponsored a lot of local music through events at the Meyer Theater or with On Broadway. And starting next summer, we’re going to sponsor a local kids’ soccer team, which I want to do more of.”

The future
As for The Heel’s future, Dempsey said he wants to continue to grow. 

“We grew 10% in 2022, and I hope to be able to continue to add and train some additional service-driven salespeople because if we can accomplish that, we can ramp up advertising,” he said. 

Dempsey said he is optimistic.

“There seems to be a renaissance of people wanting to shop locally,” he said. “Young people don’t always know how to shop in person, so we’re giving them an experience that can hopefully set the tone for what shopping can look like, instead of just clicking on something and getting whatever shows up.” 

Dempsey said The Heel also has a shoe repair shop where it handles fixing, modifying and cleaning, “which legitimizes that old-world experience because they can come back and be taken care of.”