Chicago GM comes home to open dual-brand Hilton

The Hilton Garden Inn/Homewood Suites by Hilton Chicago Downtown South Loop soft-opened in May and will have its grand opening in November. Photo credit: Hilton

When the dual-branded Hilton Garden Inn/Homewood Suites by Hilton Chicago Downtown South Loop officially opens in November, the hotel will have a GM with 20 years of experience in hospitality. Jermaine Anderson has overseen a range of openings around Chicago in recent years—but this property presented a unique opportunity for the industry veteran.

Growing Up

Anderson “grew up” in the Chicago restaurant where his mother was the general manager. “I learned a lot from my mom during that time period and it really intrigued me into hospitality,” he said. When it was time to choose a college and a career path, he realized his personality was perfect for the industry. “I can meet somebody new and different every day, from a different walk of life or different career path,” he recalled thinking at the time. 

He studied hospitality management at Chicago State University while simultaneously working at the Hyatt Regency McCormick Place. On certain days of the week, he said, people could walk into the hotel and see what jobs were available on a large board. “I filled out this application and they said, ‘What position are you applying for?’ And I wrote down every position that was available,” he said. He started as a front-desk agent and rose through the ranks, gaining experience as a night auditor and a supervisor. By 20, he was working as the front-office manager at the Hyatt in Lisle, Ill. “It taught me so much, but I was still so young,” he said of his time at the hotel. “I remember being afraid to tell people how old I was.” 

After some time in New Jersey and Philadelphia, he returned to Chicago but decided to move on from Hyatt brands, joining the team at urban real estate developer Crescent Heights. “They were building a condo hotel in Chicago at the time,” he said. At the property, called the Raffaello, Anderson put what he had learned at Hyatt properties about standards and procedures to use, adding his own twist on the ideas. “How could things be better if you didn't have those strict guidelines or the cookie-cutter approach to things? That was my thought,” he said. “And that's how I think about this industry nowadays—how can we think out of the box and make the hospitality industry more acceptable for all?” 

At 27, Anderson was promoted to GM of the Raffaello, achieving a personal goal—Chuck Floyd, Hyatt Hotels Corp.’s global president of operations, had been a GM at that age and Anderson wanted to match the benchmark. Once in the position, however, he realized that he had to manage the property’s owners as much as he managed the employees. “That's the biggest thing—you have to listen to all parties and then actually find a medium where it just works,” he said. During his time at the Raffaello, the condo-hotel reached 100 percent occupancy both in sales and rentals. 

Opening Doors

Jermaine Anderson
Jermaine Anderson.
Photo credit: Nicole Casaletto

After several years at the Raffaello, Anderson had the opportunity to open a new hotel in the city. Being part of the opening team for the Godfrey Hotel Chicago presented another opportunity to create something from scratch. “There were no rules and there were no limits, there were no standards,” he said. “I was able to work with our team and actually, literally, build the brand standards for this hotel.” The Godfrey went on to become a chain with four hotels open nationwide, and Anderson went on to open the LondonHouse Chicago as the property’s first GM, collaborating with Juan Leyva (profiled earlier this year) as his director of operations.

Related: LondonHouse Chicago GM in the industry for the long haul

As with the Godfrey, Anderson again had a chance to develop a hotel’s standards and character as the property prepared for opening. “It's building a team, it's building a culture,” he said of the experience. “To walk away and know that you built something that will stand for 25, 50, 100 years is just amazing.” The project also gave Anderson his first connection to Hilton, which became useful when—after a year with Virgin Hotels—he was ready to open another property near his home neighborhood.

“The South Loop brings me back home,” Anderson said of the Hilton Garden Inn/Homewood Suites by Hilton Chicago Downtown South Loop, which soft-opened in May and is scheduled—as of press time—to open in early November. “When I saw that we were opening a hotel here, I said, ‘This is perfect. This has my name written all over it.’ I want to be close to home and back to the neighborhood that I grew up in and give back and see how we can turn this area into a booming area.” The idea of opening and operating a dual-brand property also was intriguing, if somewhat intimidating. “At first, I was a little concerned,” Anderson recalled of the opportunity. “I didn't know which way this would go.” During the interview, he acknowledged that two hotels would usually require two GMs. “But I'm competent in my skills and I know that I can manage both properties as one,” he told the developers. Instead of applying to one of the properties, he insisted on applying for both. “I want to make sure that both hotels are given the same level of service from one general manager.” He got the job, and since the soft opening has adjusted to the different demands of each property, finding the right elements that work for one or for both. “I prefer to view this as a combined effort,” he said. 

Jermaine Anderson's...

Biggest Challenge: “I was 20 as a front-office manager. I was 27 as a GM. That was my biggest professional challenge because there was a time when I was afraid to tell people my age because some of the leaders in the room were old enough to be my father.” 

Biggest Success: “No matter what someone's status is or title is, they still put their pants on the same way as you and I: right foot, left foot ... I just [had] to be confident in myself that I could do what I was meant to do, and that was to run a hotel.” 

Advice: “I go into [another] hotel and I'm looking at how their operations work and how can things be better? How can I make my operation better than this? What things are they doing that we're not doing? And it drives me crazy, but that's just the work in me and that's the enjoyment that I get out of it.” 

Secrets to Success 

Arrive early. “I always try to arrive early just to meet people and be prepared for when a meeting starts—or anything starts.”

Treat everyone like they're the CEO. “No matter if it's a manager, if it's a janitor or if it's a busboy, I believe everyone should be treated like the CEO because everyone has great ideas and thoughts that can ... help to make the organization better.” 

Maintain quality of life. “A lot of times in the industry we get caught up in trying to make it to the next level that we don't take time out to breathe and focus on our life, our health, our families and things of that nature. I started off when I was 20 years old in this industry and I remember working 16 hours a day, 18 hours a day just to impress my managers. And it was great for me and I think there are times when that should happen. But I look back and I think I lost some precious moments in my life, too, just because I worked so hard that I may have missed a birthday or one of my kid's soccer games.” 

Hilton Garden Inn/Homewood Suites by Hilton Chicago Downtown South Loop
Rooms: 342 | Owner/Manager: SB Yen Management Group | Opening: 2019