The Square Online Guide to Holiday Selling

The Square Online Guide to Holiday Selling
‘Tis the season for get-togethers with loved ones, special meals shared, traditions made, and gifts exchanged. The holidays are often the busiest season of the year for retailers, restaurants, and service providers alike.
by Samantha Argos Nov 10, 2023 — 5 min read
The Square Online Guide to Holiday Selling

‘Tis the season for get-togethers with loved ones, special meals shared, traditions made, and gifts exchanged. The holidays are often the busiest season of the year for retailers, restaurants, and service providers alike, with online sales making up 21.6% of holiday retail sales. Holiday shopping kicks off with Cyber Week, the five-day period from Thanksgiving to Cyber Monday. In 2022, Cyber Monday was the biggest online shopping day in U.S. history, with revenue hitting a new record $10.7 billion.

So how can you make the most of the year’s biggest shopping season? The Square Online Guide to Holiday selling is packed with tips on getting your seasonal offerings just right, attracting customers, leveraging the latest Square Online features to create the best online shopping experience, and maximizing online orders and bookings. Let’s dive in!

Tailor your offerings to customers’ holiday needs

Perfecting your holiday offerings can take several forms based on the type of business you run. You may want to consider introducing new inventory, menu items, or services, and it’s important to position your existing ones accurately to serve customers’ holiday needs.

Expand your inventory

Online retailers can win the holiday season by capitalizing on holiday shopping trends and offering seasonally-relevant items. If you’re a food and beverage business, consider launching specialty menu items such as premade holiday meals for preorder or giftables such as cocktail kits, cooking classes, and branded merch. Square Online’s Printful integration is a one-stop shop for inventory design and sourcing, print-on-demand production, and fulfillment — a streamlined way to expand into new offerings.

Make gifting simple

During the holidays, it’s more important than ever to allow customers to give gifts in the way that’s most convenient. Create a category or a Featured Items section on your Square Online site to highlight holiday-relevant items. Enable gifting options and allow customers to add a gift message, request a gift receipt, and pay extra for gift wrapping on their orders. Offer eGift Cards on your site as an extra convenient gift. And finally, if you offer shipping, you can now sell any of your online inventory as subscriptions, which make great gifts and lock in recurring revenue all year round. Customers are increasingly willing to subscribe for a small discount and for convenience: think monthly refills of beauty supplies and consumables and product of the month clubs which make great gifts.


Give your site a holiday glow-up with new design features

Since you’ll likely receive more site traffic during the holidays, what better time to make sure your site is looking its best? Square Online’s newest site customization features make it easy. Take advantage of new layouts, site styles that group colors, fonts, and other site elements together as an easy starting point, video and slideshow banners, scrolling marquees, and more to make your site perfectly reflect your brand or give it a holiday flair.

Emperor Cycle Co.jpeg

Run limited-time offers and promotions

The record-high online spending last holiday season was largely driven by deep discounting during Cyber Week. As inflation rates rise, consumers are increasingly selective about where and when they buy — often comparing multiple options before making a purchase — and today’s consumers expect Cyber Week to bring some of the biggest discounts of the year. While it’s important to be selective about how often you run a discount to maintain effectiveness, online shopping holidays are an ideal time to run a special offer to help drive sales.

Consider using an offer structure during Cyber Week that differs from your typical offers to generate added excitement. Some examples include deeper percentage discounts than usual on specific items and categories, a small percentage discount on all items plus a deeper discount for higher order values, or a buy one get one free offer. Also consider launching offers that ramp up in value throughout Cyber Week, reserving your best offer for Cyber Monday to sway last-minute purchasers.

Square provides a few different discounting tools to meet your business needs:

Automatic discounts

Use automatic discounts to automatically apply a discount to online and in-person purchases based on rules and criteria you set, including specific items and categories, customer groups, order values and quantities, and more. Your discount can exist for a limited time, or can recur on specific days of the week or times of day.

Vanity code coupons

Create vanity code coupons in Square Marketing if you want customers to input a promo code to redeem an offer. Vanity code coupons can be helpful when you only want a subset of customers to be aware of an offer — for example, customers you sent an email or text message campaign including the promo code — rather than making the offer available to all customers who visit your site.

Scheduled item updates

If you plan to run a $ or % discount across your whole site or on specific items and categories, scheduled item updates is another easy alternative to setting up an automatic discount. You can use scheduled item updates to schedule when a discount goes live or when a product becomes visible on your site, then generate excitement about the upcoming flash sale or product drop via marketing.

Generate awareness about your holiday offerings

That brings us to arguably the most important strategy to maximize online sales during the holidays — making customers aware of your holiday items and offers. Follow this playbook to drive purchases from existing customers and attract new ones that remain loyal for years to come.

Holiday sale.jpeg

Send email and text message campaigns

Send your contacts email and text message campaigns using Square Marketing, which offers a 30-day free trial as well as some free email templates. If you use a different marketing platform like Mailchimp or Klaviyo, leverage Square’s streamlined integrations to make sure your contacts sync seamlessly.

Year-round, it’s important to remain strategic about when you send one-off campaigns to avoid over-messaging your contacts and driving unsubscribes. However, customers are accustomed to a ramp-up in promotions during the holidays. Consider sending multiple campaigns to generate hype for upcoming offers, announce when your offers go live and drive urgency to purchase, and to launch deeper discounts later in the season. Learn more about crafting a holiday email strategy.

Post on social media

Craft posts on your social media channels to give followers a behind the scenes view into what makes your business special during the holidays. Showcase your physical location if you have one, your staff, your holiday production and fulfillment processes, holiday-relevant offerings, and available deals. If you’re a food & beverage or services business, use Order Food or Book Now buttons on your Facebook and Instagram profiles and stories to make online ordering and booking even more prominent. Get inspired by national brands’ holiday social media campaigns.

Launch a site banner

Use a banner to bring extra attention to limited-time holiday promos when potential customers visit your site.

Attract new customers

During the holiday rush, all businesses are competing for consumers’ attention. You want to make sure your site products show up everywhere potential customers are searching for them across the web. If you’re a local business, make sure your Google Business Profile is claimed and up to date via Square’s streamlined integration, which helps you show up more prominently in Google search results and Maps. If you sell physical products online and use Square for Retail, you can list your items across Google surfaces using Google Listings.

The holidays are also a good time to try digital ads to attract new customers that fit your target audience. Square has integrations with Meta for Business to help you run ads across Facebook and Instagram, along with apps like Kliken that enable ads on social, search, and across the web.

Keep customers coming back

With all the new customers you’ll attract during the holiday season, you’ll want to have programs in place encouraging them to come back year-round. Make sure you have a pop-up on your site to capture email addresses from site visitors (even those who don’t make a purchase) so you can grow your marketing contacts list. Square Marketing offers a suite of automated campaigns that you only need to set up once, and from that point they’ll be automatically sent to customers that meet specific criteria. For example, you can automatically send an email or text to first-time customers prompting them to purchase again, to customers who leave an item in their cart without completing the purchase, to customers on their birthday, and more.

With Square Loyalty, you can give customers even more reasons to come back by letting them earn points on purchases that they can then redeem for discounts or free items.

Here at Square, we’re excited for another record-breaking holiday season and we hope you are too. For more holiday best-practices, hear from other sellers in the Square Seller Community.

Samantha Argos
Samantha Argos is a product marketing manager at Square, where she focuses on helping sellers leverage Square Online’s powerful features to grow their online sales.


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