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The Grove Hotel in Kingsville, Ontariosupplied

Forget chocolate on the pillows. At The Grove Hotel in Kingsville, Ont., guests love the pillows themselves.

“We get asked all the time about our pillows: what’s in them, where we get them and where customers can buy them,” says Jennifer Flynn, owner and operator of The Grove Hotel, which opened in 2016 and was named one of Tripadvisor’s “best of the best” small hotels in Canada five years running.

It became such a thing, in fact, that Ms. Flynn – with the help of payments solutions provider Square – started an online shop, selling the pillow and mattress brands that are found in guestrooms.

It was just another way to expand the business, which now consists of The Grove Hotel, The Grove Bike Company (an e-bike and cruiser rental shop), two coffee shops called Joe Hot+Cold, and The Grove Motel, which recently opened in the nearby beachside community of Colchester.

A multihyphenate business approach, which involves diversifying revenue streams by adding non-core products, services or experiences, has been at the centre of The Grove’s success. By not limiting itself to one type of business and always being on the lookout for new opportunities, The Grove has grown into a brand with unique but unified offerings.

Square has been there along the way, starting out as the point-of-sale technology in the hotel coffee shop and becoming the standard for all The Grove businesses last fall.

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The Grove Motel in Colchester, Ontariosupplied

“Square seemed like a better fit than the payment processor we were previously using,” recalls Ms. Flynn, adding the experience with Square has been nothing but positive. “It has allowed us to function as a multifaceted business very easily.”

For companies large and small, this new way of operating is moving full speed ahead. According to the 2023 Future of Commerce report by Square, 85 per cent of Canadian businesses plan to add even more channels this year. For example, 89 per cent of restaurant operators plan to expand their non-core products and services, such as selling retail goods and meal kits or offering cooking classes. The right payments provider makes it all seamless and helps businesses run smoothly.

That’s especially true on the labour front. With so many businesses and products, it’s imperative for Ms. Flynn to have a view into all locations and assess where her time and efforts are needed. She can do that with Square.

“Even on a cell phone, I can pull up sales for our properties without actually being there. Because we’re a family business, I tend to be wherever it’s needed. Just to know, ‘Oh, that location’s very busy at the moment, maybe I should check in.’ I love that aspect of Square,” she explains.

Knowing where sales are surging and where staff needs to help out is tracked and accounted for through Square’s software. “Seasonally, [Square is] especially helpful because we have a downtown property that is business-traveller focused during the week, and we have the motel in a beach community which tends to be busier during the weekend,” Ms. Flynn says. With Square, she adds, she’s able to effectively balance staffing needs at both properties.

In a business like The Grove where aesthetics matter, Square has the right mix of form and function. From The Grove Hotel’s homestead chic vibe to the eclectic and colourful cafés, the Square hardware’s sleek design fits in everywhere – an aspect Ms. Flynn found most appealing at first.

“It’s super sleek and clean-looking, which is important in the hotel, but especially in the cafés,” she says. “You want to have a clean-looking environment in business these days.”

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Jennifer Flynn, owner of The Grove Hotel and the Grove Motelsupplied

However, there are ways to make Square’s system feel custom in each location, adds Ms. Flynn, explaining that she and her team are able to load specific photos or content to the welcome screen of the payment system to give it a personal touch.

“Our branding is completely based on being fun, edgy and creative. I take to changing the screen all the time, so there’s always a funny quote or just something to spark someone’s interest,” she says. “I really enjoy that part of it because it allows our branding to shine.”

While the coffee shops currently use a loyalty app, Ms. Flynn says the plan is to switch to Square’s loyalty program software as “it’s much easier to have it all under one system and their pricing is much more favourable for us.”

Ms. Flynn admits letting go of the old system came with uncertainty about how the new system would measure up, but Square surpassed her expectations.

“If I’m being truthful, we kept it on the desk for a couple of weeks,” she laughs, “because I was afraid to let go and afraid of the change. But [Square] was easy and we never had to go back to the old system.”

Next, The Grove team plans to open a spa. Square will be an integral part of this next adventure as it has become a seamless part of the expansion process.

“It’s easy, reliable and lets us do what we want to do and expand where we want to,” says Ms. Flynn.

To learn more about Square’s solutions for multihyphenate businesses, visit

Advertising feature produced by Globe Content Studio with Square. The Globe’s editorial department was not involved.

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