Lilly Corning Thompson, Erin Heringer and Katie Edwards are under a lot of local pressure.
Together, they purchased Caramel Cookie Waffles from founders Jan and Judy Boogman in 2023. They’re the new ownership trio of a favorite Billings staple established nearly half a century ago, and they know this brand has a special place in many Billings hearts.
Over the last few years, Corning Thompson, Heringer and Edwards have immersed themselves in caramel cookie culture, while enhancing efficiencies and standardizing cookie operations with a goal of expanding the brand through distribution, all while keeping true to tradition.
“Caramel Cookie Waffles has always just been part of the fabric of what it means to be part of this town, for me,” Corning Thompson said.
She carries fond memories of Caramel Cookie Waffles, from eating at the cafe with her mom, college care packages, and the 10-pound Caramel Cookie Waffles dessert trays, a Christmastime tradition of her grandmother’s.
“Even if caramel cookies aren’t everyone’s favorite dessert, people have a real affection for this place and this product,” she said, “And our job is to honor that history while making sure the cookies can reach a lot more people without ever losing that hometown soul.”
When the sale documents for Caramel Cookie Waffles came across Corning Thompson’s desk at her family’s commercial real estate firm Corning Companies, she was quickly drawn to the prospect of owning — and preserving — a piece of her childhood. She immediately knew who she wanted as a partner, her engineer-minded friend Heringer, who’d grown up in her family’s aviation business Billings Flying Service. Of the three owners, Heringer is the operational-savvy partner.
When the two approached local banker and friend Edwards about financing their endeavor, she surprised them by saying not only did the numbers add up, but she wanted in as a partner. They had their numbers gal, and two turned into three. Together, they’re a collaborative team.
There were multiple parties interested, the three explained.
“We interviewed with Jan and Judy multiple times. They had to vet us and make sure that what they wanted for the future was going to align with us,” Corning Thompson said.
“This place is successful because of Jan and Judy and the community,” Edwards added.
The Boogmans stayed on for a few months after the sale, to help ease the transition and familiarize the three with their grassroots family business.
“They were so integrated into the community in truly the most beautiful way,” Corning Thompson said. “We learned a lot about how they did their business, the food they make, the service, the quality, the uncompromising. We learned everything from them.”
“They’re the hardest working people I’ve ever met,” Edwards said. “I don’t know how they did that for that many years.”
Judy handed down her recipe book, a treasure trove of cafe specials and baked goods inside. Their cookie recipe though, it turned out, was never jotted down. They worked with Jan to put his sacred cookie recipe on paper.
“The recipe was in his head and in his hands, by feel,” Edwards said.
“He was used to it, you know, and we weren’t. He made the dough every day,” Corning Thompson said. “We just needed to control everything and get it much more replicable, so we could provide a consistently excellent product.”
They kept the entire Caramel Cookie crew on, and after listening and learning even more from longtime cafe manager Sarah Rehn, head baker Makiko Yamashita and cookie operations manager Sam Biesheuvel, they decided to make a couple adjustments to give everyone more room. They bought a new commercial oven for Yamashita to be placed in the cafe at 17th Street West and moved all cookie operations to a warehouse off Airport Road on AJ Way. There, they have plenty of room to expand their cookie production.
Though it’s under new ownership now, Heringer has been grateful to have her family's old company Billings Flying Service as neighbors to the new Caramel Cookie Waffles operations warehouse. They’ve been helpful in troubleshooting their new cookie oven, shipped all the way from the Netherlands, she said.
Boogman would make about 3,000 cookies per day using Sweet Pete — his nickname for the cafe’s original oven. It produced 1,200 cookies per hour. The new setup produces about 4,000 an hour. Their daily record so far is 11,000 cookies. They’ve slowly been ramping up production, and it’s been quite the learning process to get to this point.
Staying true to Boogman's roots, they worked closely with Stroopwafel carousel-oven specialist Marco Gertz in the Netherlands, who custom built the machine they now affectionately refer to as Sweet Billy, a play on Billings. After a year of development, Gertz traveled to help install Sweet Billy after it was delivered in December 2025.
The first half of 2026 was spent fine-tuning Sweet Billy operations and stabilizing production. There are a lot of factors to consider when bulk-baking a finely crafted cookie, like temperature and humidity control.
“We were really passionate about trying to stand this facility up and keep jobs in Billings, and to be able to control our quality of our product," Edwards said. "That was really important to all three of us.”
Corning Thompson agreed.
“There's such pride in being able to do something world class in your hometown,” she said.
No matter who they reached out to locally, once they heard it was for Caramel Cookie Waffles, they were onboard to help. Heringer said support has come in many forms, from Montana Manufacturing Extension Center, Montana Department of Agriculture, and numerous Billings-area tradespeople.
Now that regular production is stabilized, they can transfer their energy to expansion of distribution. They have a goal of producing 200,000 cookies monthly. They currently have about 300 wholesale accounts, regionally.
Caramel Cookie Waffles can now be found in Ace Hardware, Scheels, and many other stores throughout Montana, Wyoming, Washington, Idaho, Nevada, North Dakota, South Dakota, Minnesota, Wisconsin and Florida.
First, they experimented shipping cross-country by sending an insulated cooler-box to relatives in Florida. The family enjoyed their cookies, and the experiment was a success.
Then comes the challenge of shelf life.
“We don't have any preservatives, and we want to keep it that way. But that limits our shelf life,” Edwards said. “These don't go bad, but they might get stale after a while.”
Right now, she said optimal shelf life is up to three months.
“Everything comes back to the quality and consistency of the product that we're not willing to sacrifice for sales,” she continued.
A simple way they learned they could extend shelf life and better protect the cookies was to change the type of plastic used for packaging. And cold packs are added to the boxes to aid in cookie quality when shipping in hot weather.
“The plastic that they had previously been using would have little micro fissures, and so it didn't control temperature and airflow as much,” Corning Thompson said.
Next up in the Caramel Cookie Waffles test kitchen, they’re experimenting with introducing seasonal flavors. Fans have no fear though. The original caramel cookie will always remain an anchor to the Billings brand.
“From our perspective, it was a perfect product already. We weren’t gonna try to sacrifice that,” Corning Thompson said.
What started in Jan and Judy’s hands, these three Billings women strive to keep safe in theirs.