HARLEY-DAVIDSON OF MADISON: THE DEALER WHO CARES

I visited Harley-Davidson® of Madison right in the middle of a Midwest winter. The rain mixed with the snow made riding in on a Harley-Davidson just about impossible. I mean… Not impossible, but y’all know what I mean.

It was cold enough that nobody would’ve blamed me even if I’d shown up in a snowcat. Wolf, Rebecca, if you’re reading this, I promise I’m comin’ on two next time!

Anyway, I was coming from Chicago, and the whole morning had that heavy, gray, winter feel that makes you grateful for heated seats and good coffee.

I left the Windy City early in my lovely little rented sedan and started the two-and-a-half hour schlep north. The fog was so thick in spots I could barely see 50 feet in front of me. The temperature was in the low 30s, and once I got out of the city, everything turned white.

Snow on the shoulders, snow in the fields, snow stacked up along the tree lines. I’m sure it’s a beautiful part of the country when the sun’s out and the roads are clear, but that morning it felt like I was driving through a blank canvas with headlights.

When I finally pulled into the parking lot, the first thing I noticed was how clean and sharp the building looked. From the outside, it felt like the dealership you’d picture if someone asked you to describe what a Harley-Davidson dealership should look like. Big, bright, modern. Then I looked up at the front windows and saw something that immediately made me smile.

Right there by the main entrance was a Knucklehead chopper, sitting in the window where you couldn’t miss it. Not tucked away in a corner or treated like some fragile museum artifact. Just posted up front and center right inside the window.

One year later, he started working at the Harley dealership in Sauk City, Wisconsin, and when he got the opportunity to buy it in 1979, he took it (It’s not a story for me to tell here, but if you ever get the chance to ask him about it, do it).

To make that deal happen, he sold that Knucklehead, with the agreement that he’d have the first chance to buy it back someday. Years later, he did, and now that bike is the primary thing welcoming folks like me to his family’s dealership.

Over the years, Wolf’s career as a dealer took him through a lot of different chapters. In 1984, he was sent up to Wisconsin Rapids to help clear out that dealership. In 1990, he was involved with Roadie’s Harley-Davidson in Portage, Wisconsin. Later on, he and his team bought and operated dealerships in Dubuque, Iowa and Galena, Illinois, and were often called in to help with transitions when other stores in the region were closing or changing hands.

But for decades, Sauk Prairie Harley-Davidson was the heart of it all, and at one point it was the number one Harley dealership in the country under the old Bar and Shield award system. He earned more Gold Bar and Shield awards than any other dealer in the country at the time, which is a pretty wild thing to pull off in a town of about 7,000 people. But again, this part of the country is Harley country.

Harley-Davidson of Madison opened in April of 2015, and Sauk Prairie stayed open until 2016, when it was folded into the Madison operation. But it wasn’t without its tough spots. Wolf told me, “The challenge is that we’re all connected.”

What he meant was that when you move a dealership, you also move riding groups, friendships, and routines. Sauk had its H.O.G.® chapter, Madison had its own, and bringing those communities together took some work.

Today, Harley-Davidson of Madison sponsors Madison H.O.G. Chapter #3793, and it’s a big part of the local riding culture. The chapter organizes rides, potlucks, gatherings, and has a regular social rhythm that keeps people connected.

Wolf told me about their involvement with the Muscular Dystrophy Association, and how at one point they had a charity ride that brought out 3,665 riders. No, that’s not a typo.

They’ve got about 75 active members and around 250 enrolled, and they meet every first Saturday. The Madison H.O.G. chapter keeps a steady calendar of group rides and gatherings, and it’s become a big part of how local riders stay connected through the season. Between that and the dealership’s event schedule, there’s always something on the horizon once the weather breaks.

While Wolf brings decades of Harley history and dealer experience to the table, he’s not the lone reason for the dealership’s success. Rebecca brings a very different and very important skill set.

Rebecca’s been working in the dealership since 2012, first during summers and then full-time after she graduated from the University of Wisconsin La Crosse. When the Madison store opened in 2015, she came straight into the business, starting with office and administrative work.

After a couple years, she went to grad school at the University of Wisconsin Madison and earned her MBA. She became an owner in 2019 and now focuses heavily on organizational development and human resources, which might not sound flashy, but it’s a huge part of why this place runs the way it does.

When I asked what it’s like running a dealership as a father and daughter, Rebecca laughed and said they’re more similar than either of them would like to admit. That brings advantages and challenges. They’re both analytical and numbers-driven, which helps when big decisions need to be made, and they both care deeply about people, which is where the dealership’s reputation as “The Dealer Who Cares” really comes from.

She was also honest about the hard parts. “We are both stubborn,” she told me. “When we disagree, it can be a bit challenging, but we typically go our own way and then come back together with reasons for or against something and have a discussion until we reach a decision.”

A lot of that, she said, comes down to how they each think about time. “The man thinks a mile a minute, always has to be busy, and is thinking five to ten plus years down the road, which is a great quality to have,” she said. “But with my job duties, I have to live more in the current day. I have to make sure things are done right today, this week, and this month.” That difference in focus can create some friction, but it also keeps the business balanced between long-term vision and day-to-day execution.

When I asked Rebecca what it feels like to continue something her dad’s spent most of his life building, she didn’t hesitate. “It’s an incredible honor to be able to work with my dad in the business that he built,” she said. “Family-owned dealerships aren’t as common as they once were, so it’s an honor to be a part of one that is still going strong.”

She said there’s pressure, sure, because his shoes are big ones to fill, but it isn’t something that weighs on her every day. “My dad’s shoes are obviously pretty big shoes to fill, but I don’t feel a lot of pressure because I know he built something great that is set up for success,” she said. “He also still works six days a week, open to close, and shows no signs of slowing down, so that also helps take the pressure off.”

Wolf, when I asked him how it feels to leave this to his daughter, kept it pretty simple. “I got bit by the Harley bug bad in 1975 and I’ve never looked back,” he told me. “That’s why one year after getting out of the U.S. Navy I started working for the Harley dealership in Sauk City, and why I purchased it the second I had the chance. I kept falling deeper in love with the brand the more that I was around it and knew that I was all in.”

In a state where winter can keep bikes parked for months at a time, that kind of setup is the difference between a motorcycle feeling like a seasonal toy and feeling like part of your everyday life, even when the snow’s piled up outside.

And that’s not including the banquet hall they have upstairs above the sales floor (complete with a full bar), where they host customer appreciation events and private parties. It’s a real slick setup.

The service department is another point of pride. Wolf told me their goal is for everyone in service to become a master technician, and they’ve got a ton of longevity on the team. One guy’s been there 22 years. Another employee has 35 years.

That kind of tenure is a huge signal that these folks run things the right way.