Before Ben Rickerby joined Danforth Sidebar as the executive chef – and now the general manager – he was a customer. “I love going to shows. I like the vibe here and how it’s connected with music industry people,” he says. “That brings a lot of value over a paycheque. I just really enjoy the environment and I like being a part of it.”
Located in Toronto’s Danforth neighbourhood (also known as Greektown), Sidebar shares a wall with the legendary Danforth Music Hall – a 106-year-old venue known for hosting everything from indie shows to international acts. Since opening in 2017, Sidebar has become a destination for pre-show cocktails, post-show snacks and private events like weddings and bar mitzvahs. In the summer, it participates in BD Beats, a community initiative hosted by the Broadview Danforth BIA (Business Improvement Area), that features free live outdoor music on patios.“People really know the neighbourhood,” says Rickerby. “They’re used to coming to shows at the music hall. We’ve just kind of become a part of that.” With elevated pub fare like Barbacoa tacos, steak frites and smash burgers, Sidebar has built a menu that holds its own. There’s Collective Arts craft beer on tap and, on show nights, the espresso martinis are flowing.
But, running a high-volume bar and restaurant in sync with a live music venue comes with unique operational pressures. When Sidebar’s parent company went searching for a unified point-of-sale system for both venues, the team turned to Square for its upgrade.
Finding one seamless system for two high-traffic venues
Behind the scenes, some of Sidebar’s processes were still catching up to the venue’s growing popularity. “It was an old-school system,” says Rickerby of the previous POS system, which lacked the integrated tools to manage a modern operation. “It didn’t have the ability to clock [team members] in and out so we were just physically doing it ourselves in a record book.”
The team needed to maintain the strengths of a lean, independent operation – simple workflows, a tight-knit crew, and low overhead – while gaining more visibility and control. And because Sidebar shares ownership and foot traffic with the Danforth Music Hall, the tools had to work across both venues. “They wanted something that was going to be cohesive between Sidebar and the Danforth Music Hall,” Rickerby explains. “A point-of-sale system that would cover both their businesses and kind of run seamlessly.”
In other words, Sidebar needed a POS that could handle volume, connect departments and grow with the business – without overcomplicating operations or breaking the budget.
A restaurant-ready system that keeps up with busy nights
Square for Restaurants checked all of Sidebar’s boxes. “It has fairly low fees. The ease of the backend is great and the user interface is pretty easy to use compared to some other systems I’ve used before. We like things very simple here, so that was a big thing for us,” says Rickerby.
The all-in-one-solution provides flexibility and offers features like menu management. “This week, I ran a special featured mac and cheese dish. It’s super easy for me to add it to the item library and assign it to whatever menu I want,” says Rickerby.
Square Dashboard gives visibility into business performance. Rickerby exports profit and loss data in an Excel file and sends Sidebar’s owners a nightly report. The system also syncs with the venue’s inventory management tool, offering a clear picture of what’s coming in and going out.
With Square Shifts, the team ditched manual timekeeping. Now, staff can clock in and out from their phones, and Rickerby can review hours, approve changes and prep payroll easily. Sidebar also implemented Square’s new item-splitting feature, helping servers divide shared items quickly on busy nights.
Faster service, smarter operations and happier guests
The impact of the POS system upgrade is felt in both the front and back of the house. It helps the team keep up with the rush when music fans flood in on show nights by improving the flow of orders. As Rickerby puts it, “it’s speed of service and efficiency.”
Item splitting eliminates friction. “Obviously, you want to be accommodating to customers,” says Rickerby. “You hate telling them ‘no’.” Instead of letting people work out the math themselves or having a server ask their manager if they can split the bill multiple ways, staff can handle the request on the spot – no slowdown, no awkward explanation.
“You get people who come in, they’ve spent money on a ticket next door and are coming in here for just a drink and want to split something small,” says Rickerby. “To be able to say, ‘Hey, yeah, you can split those tacos,’ that’s huge. We can turn that table over pretty quickly and then fill that seat again. No stress on our staff.”
Beyond the service floor, the business benefits are just as strong. Management has a better handle on performance. Between profit and loss reports and integrated inventory tracking, the visibility provided by Square Dashboard enables data-driven decision-making. Rickerby tracks labour trends and optimizes costs accordingly. For example, if he notices that the restaurant was overstaffed the night before, he can make cuts in the schedule the next day. This helps tighten margins without compromising the customer experience.
Sidebar now has the tools to match the scale of sold-out concert nights while maintaining the agility of an independent venue. Most importantly, it can keep building its identity as a standalone destination.
“We’ve done a lot of work to keep elevating our food program and keeping that quality up,” says Rickerby. “The food gives someone a reason to go to Sidebar for dinner or date night even when there’s not a show. We are so well tied to the music, but I think we still have to kind of build our own brand too.”
In the future, Rickerby would love to push the envelope further by building on successful trivia nights and partnering with local breweries for special events. Think, three-course menu with beer pairings. “They talk about their beer, we talk about the food. It’s just more reasons for people from the neighbourhood [to come visit us] outside of the music.”