Your Checklist for Holiday Sales Success

For consumers, Black Friday marks the start of the holiday shopping season that ends in January with a final flurry of sales. But for sellers, the season begins much earlier. Critical ecommerce groundwork takes place starting in late summer, and that prep work can tap into a potential windfall.

Last year, revenue for Cyber Week, the five-day stretch between Thanksgiving and Cyber Monday, generated $44.2 billion online overall, a 7.7% increase from 2024. And Cyber Monday became the biggest online shopping day of the year pulling in $14.25 billion alone. Experts project those numbers to grow again in the 2026-2027 holiday season. 

Our number-one rule for BFCM is to start early. And if you’re wondering where to start, our checklists below make it easy to stay on top of what needs to be done. Read on to learn how to strengthen everything from AI search visibility and text message marketing to waitlists and Pay Links.

Before the sales season starts (Summer to October)

This is the on-ramp to the holiday sale season. Take advantage. The sooner you prepare your site and storefront, the more time you have to build interest in your catalog. Plus attracting a bigger audience and more traffic in this window means you’re well positioned once Thanksgiving hits.

To ensure you’re ready before the holiday season:

Generate product descriptions. Accurate, detailed product descriptions are a win on multiple levels. They make your site more polished and trustworthy, give shoppers key info to confidently complete a purchase, and create metadata so your products and services can be found via search. Squarespace’s AI Product Composer can move you off the blank page to a strong draft that you can polish and personalize.

Refine your images. Product images strongly influence ecommerce sales. In fact, 90% of Etsy shoppers say the quality of images influences them to make a purchase. Use Image Studio to generate new images faster, or reshoot and enhance existing ones, to make buying from you a no-brainer. Because it’s grounded in Squarespace’s design expertise, the output is cohesive and geared toward your brand.

Map out your holiday promotions. Make a full calendar or list of your holiday discounts and when and where you’ll promote them. Start with your Black Friday weekend offers. Consider a mix of discount types, like free shipping or returns, buy-one, get-one deals, and straightforward percentage or dollar-amount discounts.

Expand your offerings. In the 2025 holiday season, the National Retail Federation estimated that the gift card market reached $29.1 billion. Gift cards can be an easy add-to-cart moment for shoppers, and they work just as well for physical goods as they do for services and digital content. Along with gift cards, investigate add-ons and subscriptions for your most popular repeat buys.

Anticipate buyers’ questions. Along with robust product descriptions, it helps to add in an FAQ page that covers your return policy or your cancellation policy (if you’re offering a service). This gives shoppers more confidence when completing a sale while giving more context for search engines. If you need help spinning up a cancellation policy, Squarespace has a handy free cancellation policy generator. 

Cover your SEO bases. Focus on three areas: targeting the right keywords, showing up in shopping search results, and local SEO. Start by researching the keywords shoppers actually use, then draft site copy around them with Squarespace’s AI writing tool. Set up your business in Google Merchant Center so you can appear in shopping search results. To engage in-person shoppers, optimize for local SEO by claiming your Google Business Profile and adding your business address, service area, and location-specific keywords to your site. After all, Small Business Saturday is a part of Cyber Week.

Check how AI represents your site. AI search is changing the shopping scene. McKinsey is forecasting that $750 billion of consumer spending will flow through AI search by 2028. Check how your site is showing up in AI before the shopping season kicks off. Get a personalized visibility score, insights into how you're surfacing across AI platforms, and recommendations for improving your results.

Connect your payment tools. Online sales require a processing solution like Squarespace Payments, that can manage transactions, issue refunds, handle chargeback disputes, and more. Consider offering alternative payment methods, too, like buy now, pay later (e.g., Klarna and Afterpay) and digital wallets (e.g., Apple Pay and Google Pay). Digital wallets have become the most popular online payment method globally, so this is more than a “nice to have.” You can make the buying experience even more effortless by setting up mini cart and express checkout.

Test your checkout. In the lead-up to the holiday season, test your checkout process to avoid any hiccups and double-check that any planned discounts or sales show up as they should. In Squarespace, you can do this by switching on "test mode” to walk through your checkout process. 

Get your order fulfillment running smoothly. For physical goods, confirm your packing, shipping, and tracking processes can handle a surge in orders. Set clear delivery timelines and communicate them at checkout, then automate your shipping confirmations to alert customers as soon as their order goes out. Reliable fulfillment builds trust and can help bring customers back for more than one holiday season.

Build your mailing list. Email gives you a direct line to shoppers who’ve already opted in to hear from you and are looking for promotions and discounts. Start growing your list now with a sign-up incentive, like a discount code or early access to sales, so you can reach a larger audience once the holiday season hits. Consider segmenting your audience by purchase history or interests, which is shown to improve open rates by 14.31%. With Squarespace’s smart segmentation tool, you can automatically identify key groups and tailor campaigns to each.

During the holiday season (October to end of December)

When the holiday rush hits, focus on carrying out your plans and providing excellent customer service. Roll out a simple, clear marketing plan, so you see engagement well beyond the initial Cyber Week window.

Promote sales and discounts site-wide. If you’re doing Cyber Week sales or discounts, don’t limit promotion to individual listing pages. Let shoppers know the minute they land on your site. Add homepage announcement bars and pop-ups to highlight limited-time discounts. Even better, use a bit of animation to catch shoppers’ attention.

Create a sense of urgency. The scarcity principle, as economists call it, can be a driving force in holiday sales. Build demand and generate buzz by leaning into a release-based selling strategy. Consider waitlists, add low-stock labels to best selling products, and use a countdown clock on cart items to drive a fast checkout. 

Fire off your email campaigns. Don’t make the mistake of manually sending one-off emails. Scheduling and automating campaign workflows can help save you time and sanity during the rush. Start by scheduling emails so promotions go out at key dates. Draft high-impact, on-brand copy for those emails with Squarespace’s AI writing tools. Then leverage email automations to pull in products and discounts straight from your site. Use tried-and-true designer templates to stand out in inboxes and drive sales. For products that get left behind, set up abandoned cart reminders to point shoppers back to the checkout page. 

Keep your social media active. Cyber Week is a crowded, noisy time on social media, but a comprehensive social media strategy can help you be heard above the din. Share specific behind-the-scenes details about your business to connect with customers and stand out among big-name brands. You can also use all the holiday chatter to your advantage and engage in social listening.

Activate text message marketing. While inboxes are overflowing and social media feeds are algorithm-dependent, text messages provide almost guaranteed open rates. Current SMS reports show a 98% open rate, with 95% opened within three minutes. Squarespace’s new SMS marketing feature can promote holiday discounts, flash sales, abandoned cart recovery, or last-minute enrollment, among other things—all without leaving the platform.

Stay on top of orders. As orders may come in faster than usual, check in regularly so nothing slips through, especially with limited-stock items or short shipping windows around Cyber Week. If a product sells out or a shipping delay comes up, update your site and notify affected customers as soon as possible. Expect a rise in customer questions about order status, shipping times, and availability, so make sure you or your team can respond quickly. With the Squarespace app, you can track and fulfill orders on the go, so you stay on top of things even during your busiest days.

Make payment collection flexible. Even if you don’t have an online store, you can still have a Cyber Week sale. Use Pay Links to generate branded payment links you can share through email, text, social media, or QR codes. If you’re selling goods or services in person, consider using Tap to Pay to collect contactless payments from the Squarespace app on your phone.

Pay attention to what’s working. As you go through the holidays, notice what is and isn’t successful. Are you feeling overwhelmed by customer outreach? Did your text messaging campaigns really take off? Track what’s driving the most engagement, what’s selling, and what’s starting to feel unmanageable. Take this all as data to review to set yourself up even better next year.

After the Black Friday rush (late December to mid-January)

Marketers and ecommerce veterans know that by late December, the gift-giving may be over, but the shopping continues. People are still in “buy mode,” and that can translate into what’s known as “Q5” sales.

Remind shoppers to treat themselves. If holidays are “the giving season,” this post-holiday stretch is the “treat yourself season.” According to a survey by the National Retail Federation, plenty of people use this exact moment to pick up something for themselves or use their store credit and gift cards as they return items. 

Keep up with your audience outreach. The frenzied peak of the holiday season has passed. The relative quiet that follows can be a boon. Use this slowdown to your advantage. With less competition for customers’ attention, your emails, social media posts, paid ads, and text messages might be able to capture more attention. As a bonus, if you’re paying for ads, the costs may be lower. 

Share your gratitude. Now is the perfect time to thank your customers for their support during the holiday season. Make buyers feel seen and valued, and communicate what championing a small business means to you and the community at large. While you’re at it, remind them to leave reviews or testimonials, so you’ll be in business for many holidays to come.

Wrap up your holiday season with a plan for next year

Black Friday and Cyber Monday reward the sellers and service providers who prepare early, stay responsive during the rush, and keep the momentum going once the holidays end. Use what you learn this season, from which promotions performed best to where customers had questions, to build an even stronger plan for next year.

Squarespace’s tools are built to support you at every stage.