Upserve Restaurant Insider Roundtable Boston

Big restaurant groups and mom-and-pop operations may have more in common than they think. When the owner of a cozy chef-driven restaurant in a Rhode Island suburb and the CFO of a nine-restaurant group with upwards of 600 total seats came together at the Restaurant Insider Roundtable event series at Boston’s Strega Waterfront on Nov. 5, they realized that they had similar day-to-day challenges—and solutions.

Kate Dickson, who started waiting tables at 18 and now co-owns Bywater Restaurant in Rhode Island with her husband, and Malcolm Wooff, CFO of the Varano Group in Boston, both share the philosophy that going above and beyond for each guest should be standard.

“If I have to say ‘no’ to someone, believe me that I’ve had some sort of marital discord behind the scenes with my husband, who’s the chef,” Dickson said with a laugh. “If I can’t deliver on the atmosphere, the sense that everyone’s needs are being met, I lose sight of what it is that I’m doing to begin with.”

Wooff agreed. “We’re honored that people should come into our establishment, and we need to treat them with the courtesy that goes along with them coming in. If somebody’s in the North End and they want a dessert we don’t have, we will go and find it somewhere,” he said. “It’s no big deal. It’s just the way it has to be, and there is no alternative to that. If you want to succeed in this industry, you have to be beyond and above expectations.”

Technology plays a role in making sure that happens. Dickson noted that her business relies on Upserve’s Guestbook feature, which allows her to see not only which guests are repeat diners, but what they ordered and when, how they paid, and the friends and family they brought with them. “It’s so invaluable,” she said, adding that with razor-thin margins, she depends more on guest relations and word-of-mouth than traditional marketing to grow her business.

Kate Dickson and Malcom Wooff
Bywater co-owner Kate Dickson and Varano Group CFO Malcolm Wooff

For Wooff, Upserve’s menu item performance analytics have been the most impressive in terms of insights into revenue and guest behavior. Because Upserve knows each guest by name and credit card number, it is able to track not only the dishes ordered most often, but which of those dishes are more likely to be ordered by regulars than first-timers.

“A lot of people can come into your restaurant because they find something very appealing, but maybe that item is not so good, because they don’t return. You wouldn’t know that because it has high sales. Vice versa, if you have an item that maybe isn’t so appealing on the menu, but the people who have it come back. How would a normal restaurant know that? Normally that kind of item would get dropped off the menu, when in fact, it’s bringing people back,” he explained. “I think the information that comes out of Upserve helps greatly in the accessibility of data and insights that otherwise you would never have. For us, that’s been very valuable.”

Of course, technology is only as powerful as its reliability. Both Dickson and Wooff have utilized Upserve’s round-the-clock customer support resources, with Wooff having a credit card terminal replaced within 24 hours, and Dickson even getting an in-person visit from a staff member who left his hotel to give personal attention to a situation caused by construction in the neighborhood. “It made me feel like I’m not an IT department of one, even though that is how it usually goes,” she said.

Wooff also discussed how it can be difficult for any business owner to make decisions about which hardware and software products are worth the investment, especially when salespeople are regularly walking through the door with solutions.

“If you adopt every single technology that is going to bring you revenue or reduce your costs, you will die by a thousand cuts,” he said. “The key to it, for me, is you need a central point that you can actually start to adopt different technologies from. For us, it’s the POS.”

And no matter how advanced the technology, both agreed that the human connection that guests make with staff can be a deciding factor in their overall experience.

Respect and training are key for Wooff, he said. “They are experts in their field, and they are the direct interface with the client, the guest. The guest will think of the restaurant as their relationship with their server, so the servers are key and vital,” he said, adding that if a restaurant stocks fine wines, the servers should be well-versed in discussing them. “As soon as somebody walks into the restaurant, you’ve got to treat them like they’re special guests, so our training goes from the hostess all the way down to everybody who’s involved with the customer experience. That’s not just the people up front, but it’s also the people in the kitchen. It’s respect and training, I think that really works for us.”

Dickson, who has a small staff of only six, says her training involves more restaurant-industry books than formal programs. Still, she tries to instill in her staff a feeling of empowerment to act on behalf of the restaurant even when she and her husband are not in the room.

“If a guest comes into my dining room and they don’t see me, they need to be having some sort of amazing experience that has nothing to do with me. So I have to give my staff the agency to follow up on those relationships and figure out how they can make them the star of the show,” she said. “The big focus over the last three years has been to shift that so it’s the staff, making them as integral to the experience as the food or the atmosphere. To that end, I think the more they know, the better we do.”

Interested in attending the next Restaurant Insider Roundtable event? Check the schedule here.


Do you want to split the check four ways? No problem. Do you want to split the bottle of wine between two people? Too easy. Enhancing the guest experience is the business of Upserve POS.

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Meghan is an award-winning journalist and content marketing manager who lives to tell stories. Her favorites include highlighting all things restaurants, from front-of-house hospitality to back-of-house grit. When she's not writing about them, you can find her eating her way through Providence and Boston searching for inspiration with a rye Old Fashioned in hand.