While flying to Los Angeles in early January, The Habit Burger & Grill CEO Shannon Hennessy looked out the window and saw fires raging across the landscape, devastating the Palisades and surrounding areas.
Her heart sank. The Habit has deep roots in California, dating back to its first location in Santa Barbara in 1969. The brand operates throughout the state, often competing for the top spot alongside In-N-Out Burger.
Interwoven with the people of California, The Habit was in a position to help during the fires. And in that moment, Hennessy knew they had to act. The situation was far worse than the news had originally reported.
She quickly reached out to her daughter’s friends at the Los Angeles Fire Department to find out how The Habit could provide meals and donations. But when she told her team, “I want to feed L.A.,” she faced resistance. They believed their first priority should be assessing which stores were open, organizing the crisis team, and determining costs. But Hennessy refused to compromise.
“I feel my best as a leader when I’ve done something brave and unpopular that I knew in my gut was the right thing to do. I’m at my worst when I question that confidence and allow the voices in my head to water me down,” Hennessy says. “At that moment, I was unrelenting in my conviction. They wanted to talk about margins … I wanted to feed L.A. because this is our home. This is where we come from, and these are our people.”
Under her leadership, The Habit mobilized food trucks across the city, serving free Charburger meals to L.A. evacuees and first responders. More than 17,000 hot meals were delivered, providing comfort to those facing an unimaginable crisis. A small gesture created an immense impact.
As a leader in a fast-changing restaurant industry, Hennessy has learned to shift strategies under pressure. But adapting to unexpected challenges is nothing new for her.
A nonlinear career path
Hennessy began her career as a business analyst at McKinsey & Company, a global consulting firm known for helping businesses and organizations achieve performance goals. Over nearly two decades, she worked her way up to partner, thriving as a consultant until 2020.
One day, her longtime friend and mentor Chris Turner—then CFO of Yum! Brands—suggested she check out an open CFO role at KFC Global. He knew how heart-led Hennessy was and how much she valued people, and figured it would be a good fit. At the time, she had no expectations but quickly became intrigued.
“After spending just a few hours with the executive team, I called my husband and told him I wanted to try this. He didn’t think I was serious … but I had never seen a brand talk about people the way they did at Yum!, and it completely captured my imagination,” Hennessy recalls.
In what she jokingly describes as a “criminally insane” career pivot, Hennessy leaped into the restaurant industry at the height of a global pandemic. On top of that, she hadn’t used her finance degree since college, adding an extra layer of uncertainty to her new role as CFO of KFC Global. She was tasked with ensuring continued growth and profitability while overseeing global financial planning, supply chain management, and strategy.
She quickly immersed herself in the science of franchise partnerships and unit economics. But the biggest lesson she learned had nothing to do with finances—it reaffirmed why she had joined in the first place: restaurants are, above all, a people business.
“I think being a great CFO in restaurants is about finding a way to say ‘yes,’ finding a way to be able to test ideas or put resources where they belong,” Hennessy adds. “I was nervous going into it, but it’s not rocket science. I learned that finances are not the hardest part of being a CFO. It’s making sure you have the right people supporting and educating you.”
After two years, Hennessy was ready for a role that allowed her to work across more functions, including marketing and development. When the position of brand president for The Habit became available, she jumped at the opportunity. Everything she had loved about her work at KFC—shaping growth initiatives and driving digital transformation—would be key to The Habit’s success.
The biggest challenge? Transitioning from a large global franchise to a smaller but rapidly expanding brand. It was a test of leadership, requiring her to navigate major strategic pivots and rewrite the brand’s playbook in an unpredictable environment.
As president, she led franchising, development, marketing, and international expansion while strengthening company culture and cross-brand collaboration. By March 2023, she was named CEO, succeeding Russ Bendel and building on the brand’s strengths.
Becoming CEO of a legacy burger chain was never part of her plan, but Hennessy believes career growth isn’t about chasing titles—it’s about staying curious and open to opportunities. Looking back, she sees career ladders more as webs, and her own journey is a testament to that mindset.
“In my late 20s, I was struggling with this choice of doing something a little bit off of my ladder. I was curious about moving in a different direction even if it wasn’t the fastest path to the top. My mentor at the time told me to try it and see where it leads because it’s really what I wanted to do,” Hennessy says. “It’s been powerful to me because when I think about continual learning and growth, it’s more about skills, creating options, trusting your gut, and enjoying the ride. It’ll probably lead to an even better place, even if it’s not a straight line.”
Transforming a legacy brand for the future
Today, the 56-year-old burger chain operates over 385 locations across the U.S. and internationally—80 percent of which are company-owned—and is best known for its diverse, California-style menu featuring chargrilled burgers, onion rings, and tempura green beans.
Historically an in-restaurant business, with over 60 percent of transactions coming from the dining room, the brand recognized the need for change when over two-thirds of its sales shifted to off-premises. The demand for convenience had never been greater.
With Yum!’s backing, Hennessy has leveraged cutting-edge technology to rework key customer touchpoints without losing the brand’s true north. For example, when ordering curbside, customers can give The Habit a 10-minute notice through the app or website, ensuring the same high-quality cook-to-order experience. By pushing the boundaries of its technological capabilities, the brand recently surpassed 40 percent digital sales mix.
“We are experiencing major channel shifts in our business as we go from dine-in to off-premises, but we’re pivoting around a strong central point, and that comes from understanding what our superpowers are,” Hennessy says. “We’ve always stood for quality and convenience for our customers, who are busy families. But our way of delivering those two things is understandably evolving as we look to modernize our systems.”
Hennessy is also harnessing technology to navigate a major industry challenge: in April 2024, California imposed a $20 minimum wage for fast-food employees, set to increase annually with inflation. This change is expected to result in a $10 million operating loss. With over two-thirds of The Habit’s restaurants located in California, adapting quickly became critical.
Although the company anticipated the law, the speed of its implementation required immediate action. Hennessy assembled a comprehensive task force to revolutionize The Habit’s labor strategy at both the restaurant and corporate levels.
“We heavily leaned into kiosks, making them one of our top order input channels. While we had them all along, we needed to increase their usage by positioning them in customers’ sight lines and making them more user-friendly,” Hennessy says. “We are also playing around with voice AI tools, but we haven’t fully rolled that out yet.”
One of the biggest breakthroughs for The Habit was restructuring restaurant roles. The original labor guide was designed for high-volume California locations but hadn’t been adapted to reflect the brand’s broader restaurant profile. From a cross-training perspective, the guide was adjusted for greater flexibility, breaking down some of the barriers between roles.
“We feel passionately about people having a career path, joining us as a cashier or cook and then being able to work their way up to general manager and above,” Hennessy says. “So we wanted to preserve that employee journey, but we realized we had too many steps in the ladder. We realized we could streamline it while still protecting the path to success and having the kind of wage separation that we needed.”
Hennessy also challenges the notion that innovation requires sacrificing heritage. She sees the idea of giving up a brand’s core characteristics to scale as a false trade-off. Instead, she believes in pivoting and adjusting while staying committed to key strengths—an approach she has embraced at The Habit as it aims to become a category disruptor.
In August 2024, she launched a light rebranding campaign, changing the name from “The Habit Burger Grill” to “The Habit Burger & Grill” to highlight the brand’s evolving menu beyond just burgers. This shift serves to modernize the brand, communicate its variety, and reinforce Hennessy’s vision of “more magic and more margin.”
“It’s not one or the other for us. It’s about figuring out how to get both, and a part of that is investing in changing hearts even more than you change minds,” Hennessy shares. “The journey to achieving more magic and more margin [for The Habit] has been an exercise in understanding where the resistance to change is coming from, acknowledging the fear, recognizing the passion of our team, and communicating what things are possible to innovate and what we refuse to compromise on.”
With Hennessy at the helm, The Habit hopes to break the “craft ceiling,” solidifying itself as a leader in the better-burger category through its Better By Char philosophy—a radical commitment to cook-to-order food quality—and a culture of teamwork, because, as Hennessy believes, burgers are best served by an orchestrated symphony of both people and ingredients.
“On this journey to unlocking a better way to do business, I actually undersold what the team was going to be capable of accomplishing,” Hennessy says. “When you empower your team and unleash them to go look at the way we buy beef, think about packaging, or plan labor in the restaurants, they come back with an incredible answer every time.”
Embracing the power of the pivot
The reality is, there is no end in sight to industry changes; the restaurant space has always been and will continue to be in flux. This presents a unique opportunity for leaders to prepare for unpredictable change and lead with agility and resilience.
Similar to how Hennessy has evolved The Habit around its true north, she has also embraced the power of the pivot—understanding her leadership strengths, harnessing their range, and allowing for flexibility in an environment of intense change.
“If you engage the same way in every meeting, with every person and every team, you’re going to get the same result. If you’re getting frustrated, you might need to ask yourself how you can show up differently and be more flexible while staying true to yourself,” Hennessy adds.
She acknowledges that change can feel exhausting, especially when it’s constant. When she craves stability and routine, she finds strength through self-care, viewing it as a necessity rather than a luxury. This can mean an exercise regimen or simply surrounding herself with people who bring positivity and energy into her life.
“I still struggle with thinking it’s selfish to take time for myself, but I do think our energy as leaders is contagious. If you are feeling wobbly or down, your team is only going to amplify those emotions and become stressed,” Hennessy says. “And sometimes we’re so fixated on getting everything perfect, but we should be embracing imperfection and learning what does and doesn’t work. I know that’s uncomfortable for a lot of us former A-plus students.”
As a leader, Hennessy strives to empower her team in a relentlessly positive way, encouraging them to embrace the power of the pivot as well. She believes people are the secret ingredient to success and need to be coached based on their unique strengths and perspectives.
“Representation matters. The Habit’s team looks very different from a few years ago … It’s half women, half men. People who self-identify as immigrants and LGBTQIA+. Having a set of people with diverse experiences gives you different viewpoints,” Hennessy says. “It’s like a recipe in my mind, and having the right ingredients matters. I think you have to figure out how to put people together in a way where everyone feels comfortable expressing their point of view.”
Supporting and uplifting her team happens on both a micro and macro level, starting with paying attention to who contributes in meetings and actively listening to those who haven’t spoken yet. Hennessy also prioritizes empowerment at the policy level, implementing family leave policies, domestic partner benefits, ERGs, and restaurant campaigns that send a strong message about inclusivity—such as the Rainbow Shake LTO.
“When I think about teaching my team to be proactive instead of reactive to industry changes, we have to become a lot more comfortable with doing things faster and scrappier,” Hennessy says. “We have to shift our mindset to view change as an opportunity to unlock a different way of thinking. We don’t sit around and wait for the change to happen. We figure out how to get better during a crisis and leapfrog from those moments where we got handed something we didn’t ask for.”
Advice for taking the leap
When making big decisions, career pivots, or taking risks, Hennessy first listens to her gut and asks herself whether the change aligns with her true north.
“Trust your instincts. I love data and information, but I think there’s something in your gut that knows things your brain isn’t smart enough to figure out,” Hennessy says. “Listen to those feelings; if it’s telling you to lean forward or backward, don’t ignore it.”
Inspired by a TED Talk by Molly Graham, Hennessy encourages others to incorporate fearless leaps into their careers—even if they fall at first, they will ultimately soar. The key, she says, is learning not to give up during that initial descent and recognizing the difference between a learning curve and a true catastrophic fall.
“I learned how to listen to myself because I’m more often talked out of good ideas than I am otherwise, but it’s also important to have the right advisors and fresh eyes to help reinforce some of my gut feelings,” Hennessy says. “At the end of the day, it’s about finding the confidence to be able to contribute as your real self, viewing that as unique and advantageous. Don’t hold yourself back from taking risks … for every one person that oversteps, 100 people are just holding themselves back.”
If there is one thing Hennessy has leveraged most in her career, it’s her curiosity. She’s often asked by those early in their careers what classes they should take or what opportunities they should pursue, and her answer is to always take the nonlinear approach.
“The strongest leaders have pushed themselves in many different directions and asked smart questions along the way. They have taken risks, positions that went off of their resume, and roles that nobody wanted,” Hennessy says. “You have to follow your curiosity and explore various functions and concepts to build your understanding of what lights you up as a person as well as your aptitude for building a team and pointing them in the right direction.”
