You've-Got-This Holiday Guide

The holidays are the biggest selling season of the year. Let's get you set up.

Get Ready

Take a look back at last year’s sales. Then use your findings to help guide your inventory and staffing plans.

Holiday Fact #1

In 2017, November 25 (the Saturday after American Thanksgiving) was the busiest holiday shopping day for local retail businesses across Canada¹. Get ready for Saturday, November 24 this year!

Know what sells—when.

Square Point of Sale comes with detailed, real-time reports so you can track best-selling items and inventory levels, and use past sales to guide what you stock more (and less) of.

Let customers book online 24/7

Get ready for the holiday party season by building your online appointment book and accepting payments with Square.

Streamline your business.

Square works with all kinds of apps that help you run your business efficiently. Connect to shipping tools, eCommerce sites, and lots more.

Sell gift cards in person or online.

59% of Canadians plan to buy gift cards this holiday season.² Order Square Gift Cards now to stock them in time for holiday shopping.

Get Set

Make it easy for those early birds to start shopping.

Holiday Fact #2

More than half of holiday shoppers start to research and plan their gifts in early October.⁴

Accept the fastest and most secure ways to pay, even on the go.

With Square Reader for contactless and chip, customers can tap and go or pay with chip credit cards in just seconds.

Show off a sleek countertop point of sale.

With a small footprint and fast transactions, Square Stand is perfect for countertop businesses where size and speed matter.

Set up holiday discounts.

In 2017, 61% of merchants offered pre-Boxing Day sales⁵. Don’t get left behind in the price wars—grab customers’ attention with a holiday promo.

Help out friends.

Know someone who needs to start accepting card payments this holiday season? Don’t forget: You can get free processing on $1,000 of sales when you refer someone to Square.


Keep your lines moving. We all know this can get crazy.

Holiday Fact #3

On average, consumer spending at local retail businesses jumps 30% in November. And 40% of Canandian local retail businesses’ annual sales for the year are made during the months of November and December, with equal sales occurring in both months.⁶

Bust lines with extra readers.

In 2017, Canadian shoppers reported long register queues to be one of the top problems of shopping in stores.⁷ Capture every sale by busting lines with an extra reader or two.

Keep customers coming back.

Create rewards for returning customers and VIPs, offer referral rewards, request online reviews, and run flash sales to reach customers across all channels.

Save time and prevent errors.

Sell a few holiday items all the time? Use the same modifiers? Try the favourites function in Square Point of Sale and make your most frequent sales faster than ever.

Know that you’re covered with Square.

When you take payments with Square, you also get fast transfers, top-of-the-line data security, fraud monitoring, Offline Mode in case you lose signal, dispute management and lots more.

Want to keep reading?

We’ve pulled together some of our favorite articles on the how to prep for the holidays, so you can dive deep.

Give Your Social Media Accounts a Quick Boost This Holiday Season

Find Out If Your Customers Think You’re Naughty or Nice

Don’t Let Fraudsters Dampen Your Holiday Cheer

Plan Smart and Get Ahead This Holiday Season

  1. Statistic extrapolated from card processing data of businesses using Square Canada.
  2. 2018 RCC Holiday Shopping Survey (November, 2018)
  3. Canada Post 2018 Holiday Plan (August 16, 2018)
  4. Canada Post 2018 Holiday Plan (August 16, 2018)
  5. Statistic extrapolated from card processing data of businesses using Square Canada.
  6. 2018 RCC Holiday Shopping Survey (November, 2018)