After graduating from Saint Leo University in 1979, Kevin Hendrickson returned to his hometown in Kingston, Jamaica, to become the general manager of a 76-bed hotel at the age of 21. The former Courtleigh Manor Hotel was an investment property purchased by his family’s business. After receiving a bachelor’s degree in management and psychology, Hendrickson was given the opportunity to lead its operations.
Little did he know, that years later his first job would lead to him becoming the owner and managing director of one of Jamaica’s largest and most reputable hospitality companies—The Courtleigh Hospitality Group—home to five hotel properties in Jamaica.
“I was bit by the hospitality bug having worked there for 15 years,” Hendrickson said in reflecting back on his first job and his decision to pursue a career in the industry. “That’s where my love for hospitality grew because I did not have exposure to much else.”
Hendrickson said it was easy for him to cultivate a passion for the hospitality industry because of the challenges and opportunities it presents.
“It’s the instant feedback you get,” Hendrickson said. “If you’re doing a good job, the customer will let you know, and it is very rewarding. If you’re not doing a good job, you also get instant feedback that you’re not. The industry constantly pushes you toward excellence.”
During his time as general manager of Courtleigh Manor, Hendrickson also pursued an interest in the food service industry, purchasing Yummy Bakery (now Baking Enterprise) in 1988. After closing the Courtleigh Manor, he went on to purchase The Courtleigh Hotel & Suites in 1997.
From that point, he acquired additional hotels: The Ruins at the Falls (Ocho Rios) in 2001, The Knutsford Court Hotel in 2002, The Holiday Inn Resort Montego Bay in 2008, and The Jamaica Pegasus Hotel in 2011. His most recent purchase was the former Wyndham Kinston, a 300-bed hotel, which is under re-development.
Today the Courtleigh Hospitality Group holds the largest block of hotel accommodations in Kingston, offering more than 800 rooms. Prior to the COVID-19 pandemic, Hendrickson employed nearly 2,000 employees, who he credits for much of his success.
“My greatest achievement is the success of my team and all that they’ve been able to accomplish,” Hendrickson said. “It is really great to see so many team members who have been with the company for some time achieve great accomplishments and receive valuable awards for it.”
Hendrickson’s compassion and appreciation for others started early during his time as a student at University Campus. While most of his family members pursued degrees at larger institutions, Hendrickson opted for Saint Leo University, which he described as a smaller school where he would be able to focus more on his studies.
And that’s exactly what he was able to do. Hendrickson’s memories of Saint Leo include an appreciation for being able to engage in one-on-one conversations with his professors, like Associate Professor of economics and Saint Leo Athletics Hall of Fame Member Chuck Fisk. Hendrickson recalls how grateful he was for the opportunity to meet with Fisk over the years and ask questions when he wasn’t understanding what was taught in the classroom.
He also appreciated the close connections he made with classmates. Hendrickson has fond memories of spending evenings with up to eight of his peers, crammed into one room, engaging in conversations with one another.
“I loved just the simplicity of having a conversation,” Hendrickson said. “From these conversations, you learned a lot about how to listen and about others—how they think and what experiences they’ve had.”
Hendrickson came to Saint Leo University without knowing anyone at the university, but that changed over the years. He immediately connected with other students who had come to Saint Leo from Jamaica and from across the world.
“When I stood up and looked around at graduation, I realized that all the people who were once strangers had become friends,” Hendrickson said. “Saint Leo University taught me that you could live together as one.”
As Hendrickson’s business grew over the years, so did his list of accolades. His hotels and hotel food and beverage services have garnered significant recognition—from top AAA rankings to medals and trophies for competing in the Culinary Federation of Jamaica’s Taste of Jamaica competition.
The honor of serving noteworthy guests also tops Hendrickson’s list. The Jamaica Pegasus hotel and The Courtleigh Hotel & Suites has welcomed many dignitaries visiting Jamaica over the years, including former U.S. President Barack Obama, former British Prime Minister David Cameron, and Prince Edward, earl of Wessex, to name a few.
For all of his success, Hendrickson also has received personal recognition. In 2020, he was given the American Chamber of Commerce of Jamaica President’s Award for the impact he has had on Jamaica’s hospitality industry and also in 2015, the Lifetime Achievement Award by the Jamaica Hotel & Tourist Association. In 2017, he was honored with one of Jamaica’s highest civilian awards, The Order of Distinction in The Rank of Commander, as part of National Heroes Day celebrations held in Jamaica.
When asked what he thinks has led to his success, Hendrickson cites strong communication and teaching skills as foundational qualities for achieving success at anything. But ultimately, he believes that having a sense of pride in his work has been the driver behind his quest for excellence.
“Be proud of what you do,” Hendrickson said. “It will never let you fail.”