Beat the Holiday Hangover! — A Guide from Dynamic Yield
2026-02-28 19:07 Diff
https://www.dynamicyield.com/article/holiday-shopping-season/

Everyone is gearing up and there’s much to prepare for the upcoming holiday season: marketing campaigns, timely communications, promotions, server scaling, inventory updating, distribution planning, and more.

However, this year, shoppers who historically would have frequented physical locations to browse for gifts are now more likely to do so from the comfort of their own homes, meaning brands will need to step up their game in digital. With many companies rapidly transitioning to service customers online amid quarantine, even those once known for being online-first will have to find new and innovative ways to differentiate themselves. And if one thing has become abundantly clear, it’s that adapting and tailoring the digital experience based on shifts in consumer behavior, whether large or small, has become invaluable.

Compared to everyday website visitors, most holiday shoppers differ in a few key ways:

❄ They are predisposed to spend more
❄ Many are shopping for someone other than themselves
❄ Deals are everywhere and price comparison is rampant
❄ They are incredibly fickle and will bounce at the first sign of inefficiency
❄ They are often on a time crunch to receive their items before a certain date

And with this season set to break all-time records for online spending, the opportunities seem too vast, while also short-lived, to grasp.

But opportunities seized during the holidays don’t have to end there. In fact, it’s just the beginning of a potentially year-round relationship you don’t want to miss out on by focusing solely on this small, fiercely competitive window of time.

This year, it’s all about the long game.

Let’s consider a few additional holiday phenomena to tap into:

❄ A massive influx of entirely new visitors enter your site, representing a once-in-a-year opportunity like no other for new business.

❄ Visitors have their family, friends, colleagues, communities, and other social circles to care for, creating a shopping experience uniquely independent of their own.

❄ Due to the increased sense of competition, sales start earlier in the month every year, blurring the lines of Black Friday / Cyber week into what we predict will become a holiday shopping month.

Do you already have a strategy for catering to and nurturing these new visitors? We suggest ideation and experience building happens from August - September, with testing and QA in October to be ready to launch by November 1st.

In the rest of this guide, we’ll share advice on how to seamlessly onboard new guests, deliver effective messaging and employ loyalty-inspiring tactics to help you convert the new wave of holiday shoppers into frequent visitors, repeat purchasers, and brand advocates.

Chapter 1:

Enhance the Anonymous Experience

You may have the information to provide returning visitors with fully personalized experiences, but it’s the new visitors, unbeknownst to your brand, that will be arriving at your door in droves this holiday season.

First impressions with a website can make or break potentially lucrative relationships with those visitors. So, providing an all-encompassing, yet not-overwhelming overview of your goods aimed generically across audiences, is paramount.

Although you may not have any data on these visitors, you’d be surprised how much can be gleaned and leveraged from contextual information like location, traffic source, operating device, and more.

Regardless of the page your new visitors land on, they need to orient themselves and determine whether you offer items of interest to them.

A rotating hero banner showcasing your top four distinct categories, along with global bestseller product recommendations presented above the fold should set the stage and give your visitors the vote of confidence to proceed with browsing.

Any click on a category will immediately disclose the main area of the site in which they are most interested. 

If your Homepage is not a visitor’s initial entry point, consider an introductory overlay that loads once for anonymous first-time visitors, anywhere on the site.

❅

Product Discovery Widget

In addition to the above, a Pinterest-style product discovery widget with infinite scroll below the Homepage fold is a great way to quickly grab and consume visitor attention. The “misaligned” Pinterest design visually communicates to visitors that there is more content to scroll down to below, and in-fact is proven to urge visitors to scroll.

The Pinterest-style widget is ideal for new visitors, as you don’t have much data to work with and your main objective is to showcase the variety of your catalog.

Once you get to know your visitor, limited and more focused widgets are the way to go.

Looking for a more aggressive approach?

Launch a fun Tinder-style discovery widget upon arrival or exit intent.

❅

Top-in Category Navigation Recommendations

Unless visitors come with a specific goal in mind and directly seek out the search field, they’re most likely to browse using your main navigation menu.

Instead of presenting the usual laundry list of categories and subcategories, try throwing in a top-in-category product recommendation that matches the category menu currently in focus to further familiarize users with your catalog.

Take it a step further by emphasizing relevant menu items based on the categories your visitor visits during the session.

If your visitors know what they came for and are signaling their intent, all you need is a good search tool to yield the most relevant results for them to complete the purchase.

Dynamic Yield’s Search learns customer preferences and behaviors in real-time and continually improves the relevance and accuracy of search results populated.

❅

Cart threshold messaging based on location

A small gesture based on location can create a strong emotional connection.

As visitors browse your website and add items to their cart, provide a dedicated message that dynamically adapts to reflect the value of items relative to a free-shipping threshold.

For example, if an initial message says, “Free shipping to New York with $100 purchase” and a user adds a $50 product to the cart, the updated message would communicate, “You’re $50 Away from Free Shipping to New York” in order to encourage users to hit the magic number. 

New visitors may not be familiar with or necessarily trust your brand yet, but once they realize how many other people view and purchase products on your site, they’ll have the proof they need to make decisions with your business.

Notifying customers that, “157 people have bought this product within the last 24 hours,” for example, creates the impression that everyone is buying your product, validating the customer’s own thinking to buy it as well. Short-term discounts that are triggered once a product becomes really popular adds a nice twist to your social proofing strategies.

The flip-side of social proof and popularity messaging, once everyone has started buying your goods and inventory begins to run low, alert visitors of the scarcity of product and increase the sense of urgency to buy in-the-moment.

FOMO is a real thing – make sure to leverage it.

Chapter 2:

Your #1 Goal: Gain More Subscribers

The most critical of your holiday objectives is to develop continued relationships with new visitors by increasing your pool of members and subscribers.

Every new signup could mean multiple deals and opportunities down the road.

From a personalization perspective, signups are the most valuable key to identifying your customers across any channel or device, even in your brick and mortar locations, allowing you to provide a truly individualized, omnichannel experience throughout a customer’s entire journey.

❅

Leverage the ‘Deal Mindset’ to Capture Subscribers

Promos, discounts, and holiday offers might all be special, but they’re not free. 

Excite visitors with the promotions they expect, but make sure to obtain an email address in return. Otherwise, they are likely to take the discount and run. 

If you encounter visitors who are hesitant to give their contact details away, up the ante and offer a deal they can’t say no to. Gamify it by using a 'spin-the-wheel' or ‘scratch-off’ that reveals the coupon in exchange for the email address. Furthermore, offer visitors early access to holiday deals several weeks before Black Friday in exchange for their email address. People are open to sharing their details if a brand can understand and follow through with what they want and need. 

❅

Easy Membership at Checkout

Every transactional point in a visitor’s journey is an opportunity to convert them into a member. 

If a visitor has already invested effort into filling out a form, providing feedback, completing a purchase, or any other interaction with your brand, they will be more inclined to put in a little more effort in exchange for being rewarded. An optional email field for someone leaving a review or password field during checkout that immediately elevates the visitor’s status to full member are just two examples of easy gains.  

A small step for the visitor, a large step for your business.

It’s the most wonderful time of the year, so be sure to leverage the spirit of gift giving and sharing.

Allow visitors to send gift cards and e-cards with holiday greetings and blessings to friends and family. And by seizing the opportunity to incentivize recipients with a special offer to visit the site and become a member as well, you gain both the sender and recipient as potential long-term relationships to nurture.

Help customers by removing the overwhelming guesswork involved in gift giving. 

Wishlist sharing is the ultimate method for inspiring confidence when purchasing gifts visitors know their loved ones desire. The results of which can be attributed to sales, fewer returns, and potential lucrative entries in your CRM.

If a holiday shopper doesn’t have the luxury of working with a wishlist, gift finders are a great way to help customers uncover special items.

For example, some retailers serve a short survey asking questions such as who are you buying for, what are some of their interests, and what is your price range, followed by a list of recommended items to simplify the shopping experience.

Chapter 3:

Follow up, Inform, Lure Back

Obtaining contact details for new customers is just the first step in making the most from this holiday season. Once captured, you’ll need to build out a full nurture program, and we have just the tools for you.

❅

Trigger after signup/purchase

Program optimized and personalized triggered emails and push notifications to make sure you keep the relationship alive. Target visitors with emails they’ll open, messages they will engage with, and call-to-actions that drive them back to your site or app. 

❅

Trigger two weeks after last transaction

Ask for feedback, request a product review, or suggest a complementary add-on. There’s a lot of potential follows up to a sale, as well as preparation in laying the grounds for the next sale. Leverage Dynamic Yield’s optimized and personalized triggered emails and push notifications.

❅

Target with display campaigns

Regardless of sign up, once a visitor has been to your site, retarget them with relevant display ads across the web. Supporting all of our Dynamic Content capabilities, our Display Ads leverage all of our targeting capabilities -- they even support product recommendations in ads!

Chapter 4:

Build Loyalty and Brand Advocacy

Acquiring new customers is a step in the right direction. Converting them into brand advocates who serve as extensions of your marketing team is an invaluable step further. With the right incentives, up to 5% of your customers can increase your marketing reach by 95%.

Certain products need to be repurchased after certain stretches of time, such as diapers, formula, dietary supplements, and more. Get customers to sign up for repeat purchases at preset intervals.

Introduce a loyalty program offering cash-back or gift certificates based on repeat purchases to show customers you care and appreciate their business. A little goodwill goes a long way.

❅

Identify and Incentivise

Identify top performing users and target them with incentives to (a) leave voice-of-customer feedback, (b) review their experience, (c) become affiliates, and more.