Table of contents
For many retailers, the holiday season is the make-or-break stretch that can account for a huge share of yearly revenue. Last year, U.S. holiday shoppers spent $241.4 billion online, an 8.7% jump from the year before. And the National Retail Federation predicts sales will keep climbing, with total retail revenue expected to reach as high as $1.6 trillion this season.
That kind of spending power is great news, but it also comes with new challenges. Shoppers are more careful with their money than they used to be. According to Square’s Future of Retail Report, 58% of consumers say they’ve cut spending in the past year. Still, when they do open their wallets for holiday shopping, they are looking for deals, rewards, and confidence that they are making the right choice. More than 80% of shoppers said exclusive discounts and loyalty perks influence where they buy. And Google’s Consumer Insights shows that impulse buys are declining while researched, “sure-bet” purchases are on the rise.
Another big shift is timing. Holiday shopping is starting earlier every year. Nearly half of shoppers now begin browsing before November, with Gen Z and millennials leading the charge. Yet most do not wrap things up until December, which means retailers have to be ready for a long, steady season, not just a Black Friday spike.
That is where early preparation pays off. In this guide, you’ll discover how to use Square to get ahead of the rush, meet customers wherever they shop, and make this your most profitable holiday season yet.
1. Unlock more sales, in more places
Holiday shoppers are not choosing between online and in-store anymore. They expect both. And businesses that can meet customers in multiple channels see the biggest gains. According to Adobe Analytics, smartphones drove 54.5% of all online purchases during the 2024 holiday season, peaking at 65% on Christmas Day. At the same time, in-store shopping remains just as important. The Square Future of Retail Report found that 78% of retailers consider the in-store experience to be vital for long-term success.
So how do you show up in all the right places? Here are a few ideas to try.
Think omnichannel from the start.
Your customers are moving seamlessly between channels, and you need to be ready to meet them wherever they shop. That might mean running a holiday pop-up alongside your main store, creating Google product listings so new shoppers can discover you online, or using Instagram to highlight gift bundles and drive sales through your online store. Even small touches, like promoting a limited-time offer on Facebook, can help you capture sales beyond your physical space. Omnichannel means making it easy for your customers to buy from you in whichever way they prefer — without friction.
Prep your holiday catalog and inventory.
If you’re going omnichannel, your catalog and inventory need to keep up. Get your catalog ready long before the season, especially if you will be adding seasonal items or gift-friendly products.
Once your catalog is set, make plans for efficient inventory management. With Square’s new stock overview, you can. Whether you are selling online or in person, Square helps you keep everything organized with low-stock alerts, automatic purchase orders, and a real-time stock overview reporting. That way, you never risk disappointing customers when demand spikes. Even if you use third-party eCommerce tools, integrations like Thrive Inventory keep your data synced, so you do not have to juggle multiple systems.
Offer the right payment options.
Do not lose customers when it is time to pay. Holiday shoppers want flexibility at checkout, and Buy Now, Pay Later (BNPL) has become a go-to. BNPL purchases reached $18.2 billion in online spend during the 2024 season, with nearly 80% of them on mobile devices. With Square eCommerce, you can offer Cash App Afterpay alongside traditional payments, giving your customers more reasons to complete their purchase instead of abandoning their cart. For more insights on payment expectations, explore the Square guide on modern payment methods for retailers.
The takeaway is clear: every sale starts with being ready where your customers are, whether that is on their phones, at your pop-up, on your website, or in your store. With Square, you can tie it all together in one catalog, one inventory system, and one payment experience across every channel your customers want to shop.
2. Expand and tailor your product offering
Holiday shoppers are changing how they buy. They want variety, flexibility, and easy options to gift the people in their lives. The more ways you can deliver on that, the more revenue you can capture.
One of the simplest ways to expand your holiday offering is through gift cards. They remain one of the most popular holiday purchases, with the National Retail Federation reporting that shoppers planned to buy three to four gift cards each in 2024, spending more than $170 per person. You can create and sell both digital and physical cards from your Square Dashboard. Customers can send eGift cards to multiple people at once, set up a group gift, or even treat themselves. It is an easy last-minute purchase for them, and an extra revenue stream for you.
Another effective option is bundling. Instead of selling items individually, you can package them together in creative or seasonal ways. A coffee shop might bundle a bag of beans with a branded mug. A boutique might pair a scarf with matching gloves. With Square bundling features, you can sell these combinations as one product while still tracking the individual inventory behind the scenes. Bundles not only encourage larger purchases but can also cut down on shipping costs.
Subscriptions are another way to keep sales steady even after the holidays. Think of wine-of-the-month clubs, sock subscriptions, or weekly bakery boxes. With Square Subscriptions, you can turn any product into a recurring purchase. You also get tools to manage fulfillment, sales tax, and “subscribe and save” discounts that make it easier for customers to say yes.
Finally, consider offering preorders for your most in-demand products. Shoppers want the peace of mind of securing their holiday gifts early, and you get the benefit of managing demand more accurately. With Square Online preording features, customers can buy items before they are available and select pickup or delivery dates that work for them.
Together, these strategies — gift cards, bundles, subscriptions, and preorders — give customers more ways to buy from you, while helping you maximize revenue during the busiest season of the year.
3. Drive demand with marketing
Once your holiday catalog is ready, the next challenge is getting customers to discover it. The right marketing can help you attract new shoppers, bring back loyal ones, and keep your brand top of mind throughout the season.
Attract new customers
The holidays are a perfect time to experiment with fresh ways to reach people. Hosting a festive pop-up can draw in local shoppers and create buzz for your products. Our guide on creating the perfect holiday pop-up experience is full of ideas for making the most of these events. Exclusive in-store promotions also work well, especially when paired with collaborations. Teaming up with a neighboring business or complementary brand can introduce your business to a whole new audience.
But holiday discovery does not stop at your storefront. More and more shoppers begin their journey online, even if they plan to buy in person. If you are a local business, make sure your Google Business Profile is updated through Square so you show up in search results and on Google Maps. If you sell online, you can also list your products with Square’s Google Product Listings integration, which makes your inventory searchable across Google surfaces like Search, Shopping, Maps, and even Google Lens. And if you want to reach even further, Square connects with Meta for Business to help you run ads on Facebook and Instagram, or you can use Kliken to reach shoppers across search and social.
Bring back existing customers
Repeat buyers are your easiest wins during the holidays, and Square gives you plenty of tools to re-engage them. With Square Marketing, you can send email and text campaigns to announce new products, share holiday discounts, or even set up automated messages that trigger when customers meet certain criteria. Adding a loyalty program can make those promotions even stickier, rewarding shoppers with points they can redeem for discounts or freebies. Square Loyalty data shows that customers enrolled in a Square Loyalty program spend 53% more and visit 40% more often.
Make discounting work smarter
Discounts and special offers are a holiday staple, but the real win is making them effortless to manage. With Square, you can set up discounts and sales in advance so they run smoothly without extra work on your end.
-
Automatic discounts. You can create rules that automatically apply discounts at checkout once certain conditions are met. For example, you might set up a percentage off during a weekend sale or a dollar amount off when a customer spends above a threshold. Once active, the discount will apply to all items in the cart that meet your rules.
-
Vanity coupon codes. Shoppers love promo codes, but they are far more effective when the codes are easy to remember. With Square Marketing, you can create custom codes that tie into your campaign theme, like “HOLIDAY25” or “FREESHIP.” Share them in emails, on your website, or in-store signage to drive more sales.
-
Scheduled item updates. The holidays move fast, and it is easy to lose track of when a promotion should start or end. With scheduled updates, you can set sale prices or launch new items in advance, and Square will automatically update your site at the right time. You can even manage multiple items at once, so your big holiday sale goes live exactly when you want it to.
With these tools working together, your promotions feel seamless to customers and practically run themselves in the background.
Get ahead of the holiday rush
The businesses that win the holidays are the ones that start early. By preparing now, you set yourself up to meet customers wherever they shop — online, in-store, or both — and give them the seamless experience they expect.
Square makes it simple to do just that. With tools to manage your inventory, offer flexible payment options, and run smart marketing campaigns, you can spend less time on logistics and more time delivering a great holiday experience.
Ready to make this your best holiday season yet? Learn how Square for Retail can help.
