Squarespace Holiday Selling Guide: Boost Your eCommerce Success

Squarespace Holiday Selling Guide

Are you ready for the 2023 holiday selling season? The holiday shopping season provides a huge opportunity to bring in business from new and returning customers, and it's the most wonderful time of the year to spread some holiday cheer while boosting your sales. There’s a reason it’s called Black Friday, after all!

We all know that Black Friday and Cyber Monday are known for incredible deals and major discounts, setting the stage for a frenzy of shopping both in real life and online. The weeks between Thanksgiving and New Year's Day are the most hectic time of the year for brick-and-mortar retailers in the U.S., but eCommerce sellers tend to have a much longer crazy period. (In 2022, Black Friday generated a record-breaking $10.8 billion in online sales, making it the largest online spending day in U.S. history. Not to be outdone, Cyber Monday recorded a staggering $11.0 billion in online sales, surpassing Black Friday as the top online spending day ever.) What’s important to note is that the holiday season has expanded way beyond the traditional Thanksgiving weekend, encompassing the entire period from late November to early January. Shoppers now spread their purchases across several weeks and months, making it crucial for businesses to maintain consistent marketing efforts and be at the top of their games throughout the entire season.


To get ahead of this months-long holiday rush, here are my top 10 tips to get your brand ready for the season:

1. Have a Clear Return Policy (& Offer Free Returns)

One of the best eCommerce tips I can offer is to have a clear return policy and offer free returns. This will increase online sales, build trust with customers, and reduce abandonment rates. Customers may feel hesitant to make a purchase if they think they won't be able to return it if it's not what they expected. In fact, I've personally decided not to shop with companies that don't offer returns or exchanges. This time of year is a great opportunity to make sure your return policy is clear and easy to use. You don't want to be the scrooge that ruins a great experience with your stingy policies! For more information on setting up a self-serve returns portal, check out this post!

2. Offer Free Shipping

It's no secret that customers love free shipping, especially during the holiday season. This is why it’s a cornerstone of my most recommended shipping strategy! Even if you don’t do it the rest of the year (even though you should) offering free shipping as a way to incentivize shoppers to make a purchase is a great idea during the holidays. You can choose to provide free shipping on orders over a specific amount or for a limited time. This strategy not only encourages customers to buy but also eliminates any hesitation they may have due to additional shipping costs. Spread the holiday cheer by offering free shipping!

3. Turn on Afterpay

Many people prefer to spread out their purchases over time without relying on credit cards. It's similar to how your grandma might have put something on layaway at Kmart in the summer and paid it off over several months just in time for Christmas. However, with Afterpay, customers receive their order right away and pay Afterpay back over time. (Don't worry, you still receive 100% payment up front!) To learn more about how Afterpay works and how to enable it on your shop, check out this post.

4. Add Gift Cards

Gift cards are a fantastic option for shoppers who may be unsure of what to buy or prefer to let the recipient choose their own present. Some people think that gift cards are impersonal but I say that’s only true if the gift card is from a big box retailer. People LOVE shopping with small brands so consider adding gift cards to your product offerings. You can allow customers to purchase gift cards directly from your website by simply adding a new product and choosing the gift card option. This not only expands your sales opportunities but also caters to a wider range of customer preferences. Spread the joy of giving with the flexibility of gift cards.

5. Use Your Announcement Bar

The announcement bar on your website is valuable real estate for sharing important information with your customers. During the holiday season, make the most of this space by displaying enticing offers, shipping cut-off dates, or any other promotions you want to highlight. Captivate your visitors' attention and drive them towards making a purchase by leveraging the power of your announcement bar. 💡Bonus tip: if you’re looking to jazz up your announcement bar, I love this code from my pal Becca!

6. Reward Loyal Shoppers

Last Christmas, my family and I did a “favorite things” party instead of traditional Christmas gifts. The point was to share a little something that you used and loved throughout the year. The gifts weren’t necessarily huge or fancy - a really great pair of socks, a jar of someone’s favorite local-made hot sauce, another person’s must have scented candle. The point is that this is the time of year people are looking to the brands they already know and trust for gifts. Rewards could be simple (a special coupon code sent out to your VIP customer list) or more complex (I’m loving Offerwhere for a loyalty program that integrates amazingly with Squarespace) - whatever works best for you!

7. Add a Chat Widget

The holiday season can get pretty hectic, and this is when providing exceptional customer service is mission crucial. A chat widget (my favorite is LiveChat - all about that here!) can be a game-changer. By implementing a chatbot on your website, you can quickly address frequently asked questions, guide customers through the checkout process, provide product recommendations, and offer support in real-time. This efficient tool will help your customers feel heard and attended to, even during the busiest shopping days.

8. Offer Local Pickup

Even in the world of eCommerce, supporting local customers is important. By offering a local pickup option, you provide convenience to those who prefer to avoid shipping costs and long delivery times. Local pickup also gives you the opportunity to connect with your community and foster a sense of local pride. Don't forget to highlight this option on your website and let your customers know they can shop local even in the digital realm. For more on this, check out this post on how to set up local pickup or curbside delivery on Squarespace.

9. Add a Custom Checkout Form

Personalize the gift-giving experience by adding a custom checkout form to your website. This is such a simple way to allow customers to include a heartfelt gift note with their orders or offer them the option to add gift wrapping, if you offer it. Don’t forget, for those who want their purchases shipped directly to recipients, at checkout customers can enter the recipient's address in the shipping section instead of their own. You could use a custom form to allow people to indicate that the order is a gift and to not include any billing info along with the shipment. This small touch goes a long way in adding a personal and thoughtful element to each order that goes out this holiday season.

10. Create Gift Guides

Holiday shopping can sometimes feel overwhelming, with countless options to choose from. (And people are notoriously bad at making decisions when given too many options.) Help your customers navigate the gifting process by creating thoughtful gift guides. Curate collections for different categories of recipients, such as "gifts for him," "gifts for kids," or "gifts for the home." Include a mix of your own products and/or complementary offerings from other brands. By providing curated options, you make it easier for shoppers to find the perfect gifts and increase the likelihood of making a purchase. 💡Bonus tip! - an easy way to create shoppable gift categories is by using tags or categories to help shoppers filter their search!


As the holiday season approaches, it's essential to prepare your eCommerce business for the bustling days ahead. By following these tips, you can optimize your online presence, engage with customers effectively, and boost your sales during this festive time of year. Embrace the spirit of the season, spread holiday cheer, and get ready for a successful sales season!

Kristine Neil

Squarespace eCommerce Expert

My simple eCommerce solutions help you sell on Squarespace with confidence so that you can focus on running your business.

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