Hilton Head Island is a place of celebration. Visitors come here from all over the world to bask in the beauty of our island home, just as they have for decades, and toast to the adventures they had here and the people they enjoy it with. Locals get to raise a glass every day to another day in paradise.
Since 1960, odds are good that Rollers Wine & Spirits was the place where that toast began.
Jimmy and Blake Schmid of Rollers
That kind of longevity puts Rollers in a rare echelon of Lowcountry institutions, but their legacy is not just that they’ve been around a while – it’s how tightly they have woven themselves into our community fabric. Their presence goes beyond their products, because the company has long supported local causes like Hilton Head Humane, Memory Matters, Boys and Girls Club, St. Baldrick’s Foundation, Children’s Relief Fund and more.
Roller’s is an indelible part of our community, but they’re also a community unto themselves. You’ve more than likely seen these familiar faces, but what’s amazing is what they’re a part of. Every company, big or small, tries to create a culture. At Rollers, they’ve created something more.
“It’s not just that we’re coworkers. We really are a huge family. It feels like home,” said Carly DeSimone, store manager for the expansive Palmetto Bay Road location.
Carly DeSimone, Store Manager and liquor Buyer, Class B Account Liaison
A nine-year veteran of the company, DeSimone wears a few different hats besides store manager, procuring liquor and cigars for the store and visiting the many restaurants Roller’s stocks. “We just like to go around, check in to see if they need anything, and show them some love because we like to think of it as a partnership,” she said. “They’re our accounts, but more than that, they’re our partners so we want to make sure they’re supported.”
As she has grown with the company, DeSimone has experienced the professional development Rollers encourages in its employees. “It’s fun to see customers I’ve known for so long and build those relationships with our partners, and my own knowledge has grown over the years,” she said. “When I started, I barely knew what tequila was, but now I’m fortunate enough to get to pick them in beefing up our single barrel program.”
Will Hagins, Sales Associate; Nicky Geoffroy, Head Wine Buyer; Michael Robinson, Sales Associate
Wine buyer and store manager Nicky Geoffrey has had a similar experience growing her own knowledge with the company in her 10 years.
“I had just graduated with a degree in event management, and I helped run the big holiday tasting, the Mix and Mingle, as an intern. I never ended up leaving,” she said. “I was born and raised here, but I wasn’t sure if I wanted to come back after college – but I just love this team. They’re big on pursuing more education, so I was able to get my first level sommelier certification, then the next level after a few years.”
That certification, one that Rollers has allowed so many employees to reach, has helped Geoffrey refine her palate while pursuing the career she’s always wanted. “I really do like running the events, trying new and different wines, and meeting the amazing wine makers,” she said. “It’s really an amazing team of great people to work with.”
Andrew Kelly, Beer Buyer and Class B Account Liaison
Beer buyer Andrew Kelly echoes that sentiment. “The people I work with are super intelligent. They’re all experts in their field,” he said. “I’ve been doing this for 20 years, and I feel like I don’t have half the expertise of the people I work with.
A veteran of the island’s food and beverage circuit, and USCB Distinguished Alumni Award winner for 2026, Kelly has been with the company five years, getting his Ciccerone certification as he builds the craft beer program at Rollers.
“I try to stick with local products, because I want to make sure the people in our community get our support, but I also get stuff from all over the place,” Kelly said. “The only continent I don’t have a beer from is Africa – and I’m working on that.”
He brings a unique perspective to the company, having worked extensively on the island for so long. And for him, the team at Rollers is on another level. “The people who work here, everyone’s in tune with their community. Honestly, I don’t think you’ll find a more diverse team locally,” Kelly said. “And when Jimmy and Blake (Schmid) took over as owners last year, it was completely seamless. They are great people to work for, and there’s not a day where I feel like I don’t have their support.”
Stephanie Skager, Cheese and Provisions Buyer
That support can often make a massive difference in the lives of Rollers employees. Stephanie Skager, who brings in cheese and provisions and has been with the company since 2012, can attest to that.
“I started out as the wine buyer, and then about five years ago my son was diagnosed with cancer. Rollers supported me for a really long time, more than a year, even though I wasn’t able to do much for the business,” she said.
Skager left Rollers after her son passed, but not for long.
“When Jimmy took over, he called and said, ‘I need you back. We’re a family. We started in this together,’” she said. “It made me feel really good.”
Ultimately, what sets Rollers apart isn’t just the fact that it has been operating here for more than 60 years. It’s the culture the company has been able to create while fueling the island’s best celebrations.
“We really try and find everyone’s value and talents and help them be used best,” Skager said. “It’s a really empowering place to work.”
Jared Stolz and Randall Smalls, Delivery Drivers
Christopher Walkenadorns the walk-in cooler
Kathy Kellis, Sales Associate
Marla Morris, Bar manager and Wine Buyer
Mark Hann, Sales Associate
Jon Tice, Marketing Manager
David Lily, Sales Associate
Kevin Rocky Moultrie, Delivery Driver
Malachi Bowden, Delivery Driver
Jasmine Watkins, Administration
Ryan Christensen, Customer Service Assistant
Jim Schmid
Garrett Smith, Sales Associate
Dave Johnson, Warehouse Manager
