As the divisional wine director for the Chicago-based restaurant titan Lettuce Entertain You Enterprises (LEYE), Ryan Arnold is responsible for vetting a selection of about 700 wines—selling anywhere from $9 a glass to $150 a bottle—across 25 different programs and 13 brand concepts in eight states, ranging from fast-casual eateries like Foodease to higher-end establishments like Ema.
Arnold was hired six years ago and charged with creating a culture of wine in the company—building wine programs that would not only draw in customers but help cultivate a deeper knowledge and appreciation of wine among employees through a focus on learning. “That was what hooked me,” he says, “and showed me that they were serious and committed to vino.”
He also manages the myriad logistics involved in overseeing multiple wine programs, including recruiting and training for wine-related positions, implementing POS systems for the wine section of the menu in new restaurants, supervising ongoing quarterly training for front-of-house and management, and organizing dozens of wine-centric events. He’s also part of the team that oversees the openings of new locations, such as LEYE’s recently announced Mediterranean-focused restaurant Aba, scheduled to open later this spring.
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In general, Arnold says, he prefers a management style that’s decidedly more collaborative than authoritative when it comes to the challenges of overseeing approximately 400 servers across two-dozen-plus restaurants. “I don’t want to sit on a throne,” he says. “How I roll is to be as informal and approachable as possible—while still being professional.”
To that end, Arnold is always open to input from his colleagues, from on-the-floor staff to managers, about new product ideas—say, a stunning, under-the-radar rosé to consider for the summer by-the-glass menu. Such exchanges ensure that LEYE’s wine programs are an authentic representation of the individual restaurants he oversees. Wine lists include some occasional overlap of selections, but by and large, each list is unique to its property.
“Each restaurant has its own DNA,” Arnold explains. “We listen to the servers, we listen to the customer, and we adjust accordingly. Everyone feels empowered that their input is at least considered, and that makes for a happy working environment.”
Arnold, who travels at least monthly to LEYE restaurants in other markets, outside Chicago, relies on technology to help him keep tabs on everything. He uses restaurant-management software to get a snapshot of sales and other metrics in individual restaurants. He also uses a cloud-based platform and a scheduling app to communicate with servers about menu changes, new wines, and other day-to-day essentials.
A typical day in the life of a wine director who oversees 25 restaurant programs looks something like this:
6:30 am: An avid snowboarder, cyclist, and overall outdoorsman, Arnold prefers to tackle his workout first thing—usually spinning, rock climbing, or yoga—followed by a meditation session. This inward focus is a critical component to starting his busy days on a tranquil note. “Doing this job,” he says, “being in and out of so many different restaurants in three different markets, I started experiencing anxiety—Did I forget to do this? What’s happening with that? That’s when I started focusing on how to mentally calm my mind.”
8 am: After his workout, Arnold sips a loose-leaf turmeric tea (he saves coffee for later in the day) before tackling emails and texts from restaurant managers, wine reps, and other business contacts. He may take a peek at his inbox earlier, but lately he’s tried to become more disciplined about not responding immediately unless it’s urgent—another strategy to help him maintain sanity given his packed schedule. “I’m in wine,” he says with a laugh. “I’m not saving lives.”
9:50 am: Arnold starts his morning commute—by bike (he’s also currently training for a grueling distance ride of 206 miles with an altitude gain of some 8,000 feet). It’s about a six-mile trip from his condo in Logan Square to River North, a vibrant neighborhood where LEYE has several restaurants. For shorter trips between restaurants, Arnold opts for a skateboard. “I typically bike or skateboard every day unless there’s torrential rain or snow,” he says. “That’s a highlight of my day.” He may also take a few calls via his Bluetooth earphones along the way.
LEYE has a satellite office in downtown Chicago, but Arnold is rarely there. “My desk has turned into a [rotating] managerial desk,” he says, adding that he usually pops in weekly for small administrative tasks, like printing out wine notes for servers. He divides the bulk of his time among LEYE’s Chicago-area properties. “You need to be in the restaurants to understand the culture,” he says. “That face time is critical. Plus, if you’re sitting in an office, how can you know which wine goes well with which food?”
Arnold generally follows the same visiting schedule from week to week. On Tuesdays, for example, he’s at Stella Barra Pizzeria in Lincoln Park. The consistency in his schedule enables regular communication with restaurant managers and staff, since they know they’ll see him face-to-face on a certain day.
10:30 am–noon: Today, Arnold is off to a seminar on Georgian wine—which he chose over another tempting offer, for a wine-pairing lunch. He says he’s learned to prioritize events that help him hone his expertise, with the added opportunity for networking. “In this day and age of buying wine, you have to be a master [of] your time because it can be taken away very quickly,” Arnold says. “There’s always a lunch, always a dinner, always an event. I chose the seminar because I think it’s important to keep educating yourself.”
No matter what kind of event it is, though, Arnold always thinks about the bigger picture: “At the end of the day, it’s like, Can you sell this? How can you talk about this in front of guests at the restaurant?”
12:15–12:45 pm: Even though Arnold arrives at Stella Barra later than usual because of the seminar, he adheres to his typical routine: He makes the rounds, saying hello to his team, checks the previous night’s sales and notes from managers in his restaurant-management tool, and runs through an informal front- and back-of-house checklist. On his task list today is to check the vintages on the menus and make sure they’re consistent with the ones being served on the floor, and to oversee quality control on wine storage, ensuring that servers are using the proper closures. “I’m looking,” he says, “for things like whether a bottle that wasn’t supposed to be by the glass was opened.”
Sometime during this period, he also sends servers tasting notes, through the scheduling app, and other helpful tips about new wines on the menu for the dinner shift. “A lot of times,” says Arnold, “what we do is pop open something from the bottle list and sell it by the glass so that servers can taste it and become more familiar with it.”
12:55 pm: Another important matter of business involves informal meetings with the restaurant’s chefs and the catering team to discuss strategy for upcoming events like wine dinners. At any given time, Arnold may be in various stages of planning for a dozen or so events simultaneously across LEYE’s restaurants. “The rollout of these is time-consuming,” he says. “You have to not only find the winery that’s the best fit for the restaurant [but] figure out the wines you’re going use, work with the chefs on the menu they want to create, and make sure everything is unique to the restaurant.”
Even so, Arnold says, such events are a critical component of a successful restaurant in today’s hyper-competitive hospitality industry. “This gives a restaurant something to put on social [media], and it draws attention,” he says. “You have to go above and beyond right now to give people who haven’t been there before a reason to come into the restaurant, and give a value-add to your regulars.”
3:30 pm: In the midafternoon, Arnold makes some time to taste with a rep. But he points out that if he wants to optimize efficiency, he has to do a significant amount of prep work before he even sits down with a rep for a tasting session. When he texts or emails with the rep beforehand, he tries to be as specific as possible about what he’s looking to add to his programs. “You have to give parameters”—for example, he says, “I’ll say I’m looking for a New World Chardonnay by the glass that’s between $14 and $19, as opposed to having five distributors come in and they put down their seven selections. That’s also being sensitive to the wine reps’ time.”
4:15 pm: Arnold takes a quick coffee break. “By this time, it’s been a while since I’ve had any caffeine,” he says. “I’m not as ritualistic with my coffee as I am with my morning tea. Usually I will have a drip coffee and that will lead into pre-shift.”
4:45 pm: At the pre-shift meeting with servers, Arnold passes around printouts of the notes he’s sent via his scheduling app—in case anyone hasn’t had the chance to read them. He then spends a few minutes offering talking points about whatever by-the-glass wine special the restaurant is running that night. “Not only does that give the servers something to talk about at the table,” he says, “[but] when it’s 86ed and goes back on the bottle list, it gives them the confidence to sell it.” It’s one of the ways he tries to put himself in the shoes of the servers: “I do expect people to read and study, but it’s my job to make sure they’re as best equipped as they can be.”
5 pm: The restaurant isn’t yet busy, but Arnold is. This is when he takes advantage of the chance to get one-on-one time with servers to discuss such issues as “how the wine program is going, what we can do better, if they have questions about service,” he says. He also makes sure the staff knows he can fill in as needed during the shift. In the LEYE fast-casual restaurants, which don’t have a dedicated somm, Arnold might lend a hand by recommending a bottle here and there; he may also bus tables or run food. “That’s one of my greatest challenges,” he says. “When you’re not in the restaurant for four to five shifts during the week, you’re not in the rhythm, not in the cadence. I’m still learning how to do that, but it’s about being an asset however I can.”
7:30 pm: Unless he’s running an event, Arnold usually heads home now, savoring the “decompression time” of his bike commute. “During my job I’m constantly talking—to managers, servers, and guests,” he says. “I don’t want to listen to music, and I’m probably not going to get on the phone. I just like to hop on my bike—and be in my own thoughts and take in the city.
Blane Bachelor is a lifestyle and travel writer based in San Francisco. Her work regularly appears in New York magazine, Marie Claire, the Washington Post, Hemispheres, and many other publications.