If you’ve been running your restaurant for more than a couple of years, you owe it to yourself to read the A.A. Milne poem “Now We Are Six.” In it, the author of Winnie the Pooh’s adventures captures the fleeting triumphs of growing and surviving. “When I was three,” the rhyme starts, “I was hardly me. / When I was four, / I was not much more.” He goes on: “When I was five / I was just alive. But now” — now! — “I am six, / I’m as clever as clever. / So I think I’ll be six now / forever and ever.”
The gentle joke is apparent to anyone who is not, in fact, still 6. If you want to keep advancing, the poem suggests, you’ve got to be prepared to leave behind some ways of being, as painful as that can seem. For many restaurant operators, the most stressful piece of technology to outgrow is probably the one most vital to your entire enterprise: the point of sale system.
At one time maybe not so long ago, you were just starting up, and your choice (or passive inheritance) of POS reflected your best option at the time. Hopefully your restaurant has grown since then, and you’ve been witness to a sea change in how restaurants and technology play together. It’s natural to ask yourself, then, whether your POS is still up to the job. Is it keeping up with you, or keeping you tied to the past? Whoever first surmised that pain is the touchstone of growth may well have spent time with a subpar POS — one with an overly complicated or difficult-to-use interface, a tendency to lag during peak hours, or a dearth of third-party integrations.
Wherever your pain points lie, if you’re considering switching your POS system to another, read on to get familiar with the snares and benefits of such a transition. We can’t tell you what the right move is, but at least you’ll come out the other end all the cleverer.
The best POS systems keep adding features, so take advantage
It’s one thing if your system is glitchy (or downright unwieldy) and you can’t get the help you need when you need it. But what if your POS functions perfectly well and suffers only from an inability to integrate with other platforms? Order/delivery, accounting, CRM, inventory — the list of crucial tech-powered facets of your business that you want talking to your POS goes on and on.
In days of yore, you had a POS akin to an electronic cash register, and the rest was relegated to the domain of clipboard and pencil (or, worse, ancient back office desktop computer). But we are well and truly mired in the digital age, and if your data is siloed you’re going to get left in the dust.
This was almost the case for Jay Wainwright, the CEO of the sustainable seafood restaurant group Seamore’s, which has six locations around New York City. A year and a half ago, Seamore’s ditched its previous POS provider and hitched its wagons to Toast. “It was becoming clear that the company we were using had kind of lost its way in terms of investing in the evolving universe of things that a POS can help with,” Wainwright said. “Toast’s open platform model is much more dynamic. On-premise transactions are tied to the same database that our website and all the order and delivery apps feed into. For a small operator like Seamore’s, that’s a game-changer.”
Another factor that motivated Wainwright to switch was the desire for more features, as the emerging Covid-era standby that is mobile order and paying off a QR code. “That whole process was pretty much a fantasy, say, five years ago,” Wainwright said. “Our previous POS company didn’t offer anything comparable, so Toast was the more attractive choice.”
Why move from an on-premise POS to a cloud-based system?
For Seamore’s, the switch amounted to swapping one cloud-based POS platform for another. If you’re working with an on-premise POS, you may simply be looking to move to the cloud. We covered some of the drawbacks of the on-premise rigs in our explainer on the difference between cloud-based and on-premise POS systems, but the quick and dirty of it is that on-premise systems work off a server that lives at your restaurant, which means all your data lives where you work. If you want to access the system remotely — an attractive option for many owner-operators, especially those running multi-location businesses — your POS won’t be up to the task.
On-premise POS systems also are especially vulnerable to security threats (theft, fire, etc.) due to the “the data is here and nowhere else” of it all. Increasing numbers of restaurateurs are pivoting away from these traditional “legacy” systems, for these reasons, and for one more: the hardware can be lavishly expensive. “A long time ago, when all you had were these behemoth companies like Aloha and Micros, a full set of terminals was a huge capital expense,” said Wainwright, whose career in the restaurant industry began in 1996 when he founded the quick-service chain Cosi. “If you were a big company with lots of restaurants, it could cost hundreds of thousands of dollars.” By comparison, Wainwright said that the hardware associated with Toast runs him a more humane $6,000 per location.
How to prepare to make a big POS switch
A POS leap requires homework. Don’t just opt for the first sponsored ad that crops up when you type “POS” into Google (and, while we’re at it, maybe don’t click on the Urban Dictionary results). Instead, talk to sales departments at different companies before you make your choice. When consorting with a potential POS provider, verify that the system has the features and integrations you need, and pin down details on pricing, hardware, and contracts. Some companies will try to rope you into signing a multi-year contract; add that into a mix that includes buying a lot of expensive hardware and you’ve got a recipe for ongoing dissatisfaction.
Get into the weeds. Talk about payment processors: Does the company that’s courting you offer — or mandate — integrated processing? If so, what are their rates? Many cloud-based operations like Toast and Square require relatively inexpensive hardware, but they lock you into their proprietary payment gateways, which often levy higher fees than standalone processors that can be used with a variety of other systems.
Then, before you bid your outbound system adieu, you’ve got to move your operation onto the new platform. That means cleaning the data in your existing system — menu and pricing information, loyalty data, inventory specifics — before it migrates to its new home. Once you’ve ensured your data is up-to-date and trim, your new provider should be able to help you transfer it to your new system. That process may be as simple as exporting a spreadsheet or a PDF from your outbound system and having the onboarding team at your new company help you input it into their system.
Next, get your staff ready for the culture shock. Make sure your new platform has training materials and reps on-call for this transition, and go ahead and plan for a learning curve. “Don’t make the switch on a busy weekend or during the holidays,” said Luisa Castellanos of Science on Call,, a tech consultancy for restaurants. “It might disrupt service, but it’ll definitely throw your team for a loop. Give your team enough time to learn the system, and, if possible, arrange for them to do a few test runs before going live.”
The pitfalls of a POS switchover
Whatever your new situation is, Andy Freivogel, the CEO of Science on Call, urges restaurant operators to understand their systems to the best of their ability. “Sometimes restaurant owners who are changing from one system to another don’t even realize that they have to switch processors,” he told us. “Then, when the new system goes live, the money isn’t flowing where it should, and you’ve got a huge mess to sort out.”
While you’re schmoozing with the sales team, make sure you get the skinny on the onboarding process. A dedicated staff that attends to your go-live day needs and assists in training up your staff is a huge plus, because things can go sideways. “In the case of the worst go-live I’ve ever seen,” Freivogel said, “the POS company did nothing to ascertain site readiness, and the staff was not trained on the new system at all.” That obviously won’t happen to you, wise reader, but if your would-be partner isn’t set up to help you execute a flawless launch, you might consider that a red flag.
Wainwright advises that you keep the old system running for a bit before you phase it out completely, in case something goes wrong with the implementation of the new. To avoid any down time, Wainwright said, Seamore’s kept both systems in place for a spell as they worked out the kinks. Overall, the shift went smoothly, but it wasn’t without its drama.
“In the years when I was overseeing switches from one legacy system to another, we’d run into these massive problems involving outlet placement, because everything had to be hardwired,” Wainwright said. “Most of our Toast equipment is handheld, but we still had some issues. The hardest part was making sure all the devices were routed to the correct printers. We had the bar tickets printing to the kitchen for a little bit, which was kind of a disaster.”
Snafus aside, Wainwright believes that the future of POS-switching is sunnier than the past, especially given that the overwhelming majority of operators who switch are moving to cloud-based systems. “It used to be a much harder process, and it involved a lot of loss,” he said. “In the old days, when the only option was to switch from one legacy system to another, you had to completely write off and get rid of all your existing equipment — which, again, cost you a ton — because it wasn’t compatible with the new system. The switch from one cloud-based system to another was ultimately really simple, and Toast had a good roadmap for us to follow.”
Freivogel shares that optimism. “I’d say there’s a correlation between go-lives that go smoothly and the POS solutions that are growing the fastest,” he said, referring, of course, to cloud-based systems like Toast and Square.
So, if you’re looking to make a switch: do your research, plan ahead for go-live day, and be prepared for something to go wrong. When it does, call up the (hopefully) helpful, friendly tech support team at your new company. And on the big day, in case you hear the sound of bar tickets printing in the kitchen, just remember the words of Christopher Robin, another A.A. Milne creation: “You’re braver than you believe, stronger than you seem, and smarter than you believe.”