Denny LiPira didn’t leave Applebee’s because things were bad. In fact, after 26 years with the brand, things were going well. He had worked his way up from hourly employee to Director of Operations, overseeing 13 restaurants across Florida and Georgia.
But when the opportunity came to help build something new, to take everything he learned in corporate hospitality and apply it in a fast-growing, entrepreneurial environment, LiPira made the leap.
“I had a contract sitting in front of me for a year,” he says. “Eventually, I just looked in the mirror and said, if you’re gonna do it, do it today.”
Now Director of Operations for a Jacksonville-based restaurant group, LiPira oversees both Island Wing Company and The Toasted Yolk Café, with multiple locations open and more on the way. It’s a hands-on role with big growth ahead. But one of the first things that stood out to him when he joined?
Less Cash, More Control
Before Kickfin, nightly tip-outs were a pain. Managers had to count cash, do the math, and double-check everything before anyone could go home. If a tip share got missed or miscalculated, the fallout could last days. Eating into payroll, causing confusion, and damaging trust with the staff.
“With Kickfin, that all goes away,” says LiPira. “It’s integrated with Toast. It does the calculations. It pays people out digitally. And the managers get time back.”
Kickfin has become a crucial part of the team’s nightly close. Not only does it eliminate cash from the equation, it also ensures employees still get paid daily, a key part of the restaurant’s culture.
“Servers love it,” says LiPira. “They finish their shift and the money’s in their account the same day. That matters.”
When Tech Supports People, Culture Wins
LiPira believes strong systems create room for strong culture. With tools like Kickfin and Toast handling operational friction, his team can focus on what really matters: leadership, retention, and employee growth.
“Our turnover is incredibly low,” he says. “We put real trust in our hourly team members. We give them responsibilities, develop them, promote them and we pay them well. That’s the formula.”
The restaurant group has adopted a lean management model, using shift leads to handle much of the day-to-day. With clear tech and communication systems in place, those leads become the pipeline for salaried managers.
“Some people are with us for a short season,” says LiPira. “But some realize this can be a career. I want to give both types the tools to succeed while they’re here.”
Betting on Yourself Isn’t Easy—But It’s Worth It
Looking back, LiPira doesn’t sugarcoat how hard it was to leave corporate security. He wrestled with the decision for a full year. But the promise of freedom, flexibility, and impact eventually won out.
“I have more time for my family now. I have more influence over how we run things. I’m building something meaningful,” he says.
His advice to anyone on the fence? “Nothing in life is guaranteed. But if you’re thinking about taking the leap, just do it. The opportunity cost of waiting is too high.”
From eliminating cash tip-outs to supporting team culture, Kickfin has become an essential tool for Denny LiPira and his restaurants. But the bigger story is about growth, how the right systems let leaders focus on people, and how the right mindset opens doors that security never will.
“I never thought I’d be doing this,” LiPira says. “But now that I am, I can’t imagine doing anything else.”
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