In May, Josie Kilgore, brand president at Neenah, Wis.-based Cobblestone Hotels, celebrated her 20th anniversary in hospitality. And while most industry professionals work for a number of properties and companies, Kilgore has remained with one team since the very beginning.
Coming of Age
Kilgore's career began when she was a teenager, working as a housekeeper in an Oshkosh, Wis., Hawthorn Suites owned by the late Brian Wogernese, who went on to found Cobblestone Hotels and lead it as president and CEO. She soon was promoted to the front desk, but needed to be supervised by an adult because she was only 16 years old at the time.
As Wogernese’s WHG Companies grew, Kilgore found new ways to support him. When city administrators came to discuss a hotel in Brillion, Wis., Kilgore came into the office to make the small team look a little bigger. “I filed the same piece of paper and played solitaire for eight hours pretending that … he had this assistant at the front,” she recalled. “It was wild—but then I never left.” Kilgore joined the WHG Companies office—for real, this time—and was working with the team when Wogernese founded Cobblestone Hotels in 2007. She was 18 years old at the time.
“It wasn't supposed to be this at all,” Kilgore said of Cobblestone’s early days, noting that the company started out with just three hotels alongside the management division. And initially, she added, that was what Wogernese had planned. “They only wanted to do a couple hotels for themselves. They weren't going to have investors, they weren’t going to have franchisees. He wanted to just build two to three a year for him and his partner [Mark Pomerenke] and [his wife] Kim.” But as Wogernese traveled around the midwest to open those first properties, interest grew. “When people started calling us, we were like, ‘Wow, this is pretty cool. We feel pretty cool. We feel pretty important.’” The brand took off, and Kilgore became VP of franchise services for Cobblestone Hotels in addition to her work for the management arm.
Instead of attending college, Kilgore learned by watching her colleagues and following their lead. From office administration to procurement to implementing technology, she took on a range of responsibilities to become proficient in the different facets of hospitality. WHG Companies became Slate Hospitality Group and Kilgore increasingly focused on growing the Cobblestone brand.
“We didn't have even quality assurance inspections at that time,” she recalled. “It just was me supporting the properties, trying to develop different things.” Building the brand from the ground up, Kilgore and her colleagues focused primarily on what they did not want Cobblestone to be. “We didn't want to do all these things that were going to cost an arm and a leg that didn't make sense for us,” she said. The team’s experiences as franchisees on the management side had taught them how frustrating it was “to be mandated to do just absolutely ridiculous things.” Now that they were on the other side of the table, they wanted to be a different kind of franchisor.
Comfort Zones
As a very young woman in a rapidly changing field, Kilgore felt both great pressure to make the brand work and great determination to make her team proud of her.
In 2018, Wogernese informed Kilgore that she would be the company’s brand president, formalizing her responsibilities with a title to match. “It just was kind of a surprise—something I honestly hadn't even thought of,” she said of the promotion. “I remember him saying, ‘You're already doing all of this, so let's make it official.’ … it was a surprise and very honoring that he would have that faith in me.”
With her new title in place, Wogernese pushed Kilgore to do more public speaking and become “the face” of Cobblestone. “I very much like to be behind the scenes,” she said. “I don't like being on stage … I like to be running the properties and doing that side of [the business].” But Wogernese was insistent, and encouraged Kilgore to do the things that made her uncomfortable. “My biggest uncomfortability was worrying people wouldn't respect me because I was young,” Kilgore said, acknowledging that some people were dismissive of a young woman in a position of power. But Wogernese emphasized his trust in her abilities and encouraged her to use her judgment.
Now that she has been working in hospitality for 20 years, is proud of having helped Cobblestone evolve into a significant presence in the industry—and of having evolved with it. “I'm certainly not the same person I was 20 years ago. [I don’t] even have the same aspirations,” she said. “Helping create a national brand and still being around and still loving it every day— that's crazy important.”