Wilson Oswald Interview: UP on the Roof and the Future of Restaurants in Metro Atlanta
In a city known for its dynamic dining scene, UP on the Roof remains one of the most sought-after restaurants in Alpharetta. The restaurant overlooks the heart of Downtown Alpharetta and offers a creative selection of dining and drink options.
The leader of this original concept is Wilson Oswald, the CEO of UP on the Roof. Wilson and his team opened the first UP on the Roof location in Greenville, South Carolina in 2017. Just 4 years later, UP on the Roof opened its second location in Alpharetta and quickly became a must-visit destination for locals. In addition to his work at UP on the Roof, Wilson is also the director of the beverage program for Sizzling Steak Concepts, one of the largest Ruth’s Chris franchise groups in the world.
The Alpharetta.com team had the opportunity to speak with Wilson Oswald to learn more about UP on the Roof and the future of dining in the Alpharetta area.
Your family has a strong background in the restaurant industry with Sizzling Steak Concepts, the largest Ruth’s Chris Steak House franchisee worldwide. How did that experience shape your vision for UP on the Roof?
“I grew up in this industry, so hospitality is really in my DNA. Working alongside my family at Ruth’s Chris taught me the importance of consistency, genuine service, and creating moments that keep guests coming back. With UP on the Roof, I wanted to build on that foundation but offer something a little different – something more modern, more playful, and deeply connected to the local energy of each city we call home. It’s still about great food, drinks, and hospitality, just with our own creative twist.”
Why did you choose Alpharetta for your second location? What was it about the city that felt like the right fit?
“Alpharetta has such a vibrant spirit and has become one of the most exciting dining destinations in the region. It’s a fast-growing city, but somehow still feels like a tight-knit community that values good food, good drinks, and good company. When we found the rooftop space at Liberty Hall, we knew it was the perfect fit. The views are incredible, the location is central to so much of Alpharetta’s activity, and there’s a real sense of excitement here. It all aligned perfectly with what UP on the Roof is about: gathering with friends, enjoying a drink above the city, and feeling like you’ve escaped the chaos of daily life without leaving town.”
How has the community in Alpharetta embraced UP on the Roof, and what are some of your favorite stories from guests?
“The response has been incredible. From the day we opened, the community welcomed us with open arms. People love that they can come up here for everything from brunch to sunset cocktails. One of my favorite things to see is how often guests bring out-of-towners here and say, ‘This is our spot; we had to show you.’ That kind of pride from our guests means everything to us. We’ve also hosted milestone birthdays, engagements, business parties, happy hours, social brunches, and even a few weddings. Those moments remind us why we do what we do.”
Are there any plans for another UP on the Roof location in the metro Atlanta area or beyond?
“We’re definitely in a growth phase and always exploring opportunities that make sense for the brand. That said, we’re not looking to grow just for the sake of expansion. Every UP on the Roof location has to feel authentic to its city and true to what makes us special. The space, the community, the energy – those pieces all have to align. When the right opportunity comes along, we’ll know it. In the meantime, our focus remains on continuing to deliver an exceptional experience in Alpharetta, as well as at our Anderson and Greenville, South Carolina restaurants, and our newest UP on the Roof in Charlottesville, Virginia.”
Looking ahead five years, what is your vision for the UP on the Roof brand?
“In the next five years, we see UP on the Roof continuing to grow thoughtfully and intentionally. We’re in a great position to expand, but we want to make sure every new location reflects the same spirit and sense of place that define our current rooftops. For us, growth isn’t just about adding pins to a map; it’s about creating spaces where people can connect, unwind, and make memories. That’s the kind of growth that lasts and is sustainable.”
The first UP on the Roof location was in Greenville, South Carolina. What was the biggest lesson you learned from that opening that you brought with you to Alpharetta?
“The biggest lesson was to truly listen to our guests and to our teams. Greenville taught us the power of being flexible and adapting to what the community wants, whether that’s through menu evolution, seasonal cocktails, or the kind of events we host. We learned that every rooftop has its own unique rhythm, and success comes from embracing that and making it an integral part of the experience.”
You have a fascinating position, leading a modern concept like UP on the Roof while also directing the beverage program for one of the largest Ruth's Chris franchisees. How do you balance the creative freedom of your own brand with the established traditions of a classic steakhouse?
“It’s a balance I really enjoy. Ruth’s Chris is all about tradition, refinement, and excellence, and I have immense respect for that. It keeps me grounded in the fundamentals of great hospitality. UP on the Roof, on the other hand, gives me space to push boundaries, experiment with new trends, and have some fun. The two brands complement each other really well. One reminds me where I came from, and the other lets me explore where the industry is going.”
How do you see the dining scene in Alpharetta and the broader metro Atlanta area evolving in the next few years?
“I think we’ll continue to see diners looking for experiences, not just meals. People want to feel connected: to the space, to the city, to the people they’re with. Alpharetta has done a fantastic job cultivating that sense of community through its restaurant scene. I think we’ll see even more focus on local ingredients, craft beverage programs, and concepts that blend atmosphere with authenticity. Atlanta’s dining scene as a whole is quickly becoming one of the most exciting in the Southeast, and we’re proud to be part of that evolution.”
Scenes from UP on the Roof
All photos courtesy of UP on the Roof.
Spencer Myers is a founder and editor of Alpharetta.com and a longtime Alpharetta resident who has observed the city’s transformation from a quiet suburban town into one of the Southeast’s fastest-growing tech hubs. Our team’s original interviews and unique content have been cited by Fox 5 Atlanta, MSN, Urbanize Atlanta, and other major local news outlets. Through Alpharetta.com, our team connects residents and newcomers with trusted local businesses, the latest local updates, and exclusive insights from the leaders shaping the community’s future.