5 Ways to Personalize Your Customer Experience Ahead of the Holidays


Editor’s Note: This article was originally published on August 23, 2019. It’s been updated to include the most recent data and insights. 

Building relationships with your customers throughout the year helps you to boost your sales when the holiday shopping season comes around, according to Klaviyo’s research.

What’s more, in looking at the data from Cyber Weekend 2019 specifically, researchers found that 60 percent of Cyber Weekend sales were driven by consumers who engaged with an email from a brand prior to Q3 that same year. 

Additionally, consumers who engaged with a brand’s email by clicking on it had a 10 percent greater average order value and accounted for 53 percent of total sales. 

But what if you haven’t been building relationships throughout the year? There’s still time.

With a decade of planning for Cyber Weekend under my belt, I’ve seen holiday shopping patterns change over the years. And I’ve observed how the retail industry has reacted to them. 

Due to the coronavirus pandemic, never before have consumer shopping habits changed so drastically and in favor of the ecommerce industry. That’s a big part of what will help ecommerce-driven sales top $1.1 trillion for the first time ever this year.  

But just because more people have had to make the bulk of their purchases online this year doesn’t mean they’re any less discerning in how they shop. 

Customers today are much more selective, so getting the customer experience right is critical to achieving your holiday revenue goals.

And that’s exactly why incorporating segmentation and personalization into your marketing strategy is so invaluable. 

Segmentation and personalization techniques help you tailor your customer experience to different groups of people so you can both deliver the experience your customers have come to expect, as well as a highly relevant experience for those customers who may be relatively new to your brand—for example, all of the people who discovered your brand for the first time this year as a result of having to shift their shopping behavior online.

“Anytime you see an influx of new customers, especially during a major event like this [the coronavirus pandemic], from a marketing perspective, you can expect that they may behave differently than your previous cohorts… We’re trying to segment our audience to understand, out of all the people who signed up to receive updates from us, who is in each group and how large is each group? Then, we want to separate the new customers from the returning customers and try to share that new onboarding story,” said Mike Altman, senior retention manager at Who Gives A Crap.

"Anytime you see an influx of new customers, especially during a major event like this [the coronavirus pandemic], from a marketing perspective, you can expect that they may behave differently than your previous cohorts."

Mike Altman, senior retention manager, Who Gives A Crap

Brands that create personalized experiences by integrating advanced digital technologies and proprietary data for customers are seeing revenue increase by six to 10 percent—two to three times faster than those that don’t, according to Boston Consulting Group.

Segmentation and personalization strategies are essential when it comes to driving additional revenue, especially as you prepare to make the most of the holiday shopping season.

Here are five tips you can implement now to personalize your customer experience and drive revenue during Cyber Weekend and the holiday season.

1 | Make relevant recommendations to repeat shoppers based on their phase of life

Understanding what your customers have bought over the years makes it much easier to spot trends and make more relevant product recommendations that will appeal to your customers.

Have a kid’s clothing store? If your customer bought a boy’s size 12 months t-shirt last year, show them a few top selections from your two-year-olds collection this year.

Have a jewelry store? If your customer bought an engagement ring last year, share pics from your anniversary collection this year.

Have a maternity store? Offer a monthly countdown newsletter with educational tips and products each month to help pregnant women find comfortable clothes.

By using the data from your customers’ past purchases, you can meet each one where they are in their lives. But beware, there’s a line you can cross where your messages might seem creepy to customers.

Avoid this by carefully creating thoughtful and personalized messages to make your emails and social ads more attractive to your customers.

2 | Examine the behavior of your once-a-year holiday shoppers

It’s likely you have many shoppers who’ve only made a purchase from you during the holidays. Take a look back to see what they purchased and what part of your marketing strategies converted them. If these once-a-year shoppers are focused only on buying during that time of year, work with that behavior.

Cyber Weekend falls late in the season once again this year and, given the hardships that many brands faced earlier in the year due to the pandemic, it’s fair to say that the holiday marketing season will kick off even earlier than usual this year.  

Fifty-four percent of shoppers begin researching holiday gift ideas in October or earlier, according to the National Retail Federation. That’s a perfect time to start sending personalized messages to your customers with your holiday gift guides and helpful shopping tips that feature items complementary to what they bought last year.

Did they buy a computer from you last year? Show them accessories to go with their computer, like travel cases, docking stations, or anti-virus software.

Have a food store? If your customer bought food baskets or popcorn tins from you last year, they might want to purchase them again. Show them items similar to what they ordered last year and a few new choices, too, so they have options.

Have a hat store? If your customer bought a Celtics hat from you last year, show them other Boston-based sports items—a Bruins hat or maybe even new Celtics hat styles that have come in.

This helps you to stay top of mind during the holidays so your brand is an easy choice when they’re ready to make a purchase.

3 | Create first-look and exclusive offers for your VIPs

How you define who a VIP is to your business is up to you, but typically they’re the people who’ve purchased from you frequently, they’ve spent a certain amount of money with you, or they don’t often use coupon codes to make their purchase (i.e., your most profitable customers). 

You could think of them as your high rollers or your potential high rollers.


A month before the holiday time period, try offering your VIPs a few gift guides and helpful shopping tips that showcase the products they might be interested in based on what they’ve previously purchased.

Have a clothing store? If you see customers have bought a wardrobe with neutral-colored pants and tops, offer them a warm neutral colored sweater and a jacket that’s just right for the holidays that would go with what they purchased to increase their average order value (AOV).

Have a brick-and-mortar store? Prior to the pandemic, you could offer your customers an incentive to come into your store and try your new capsule collection and provide feedback. But just because they may not be able or willing to physically visit your store this year doesn’t mean you can’t still use an engagement strategy like this. 

Instead of trying to drive people in-store, consider how you can use your website to execute this strategy instead. You could instead email VIPs with a first-look at your upcoming collection online and ask them to provide their feedback about what they like and what they don’t. You could even ask them to leave reviews on your new collection as a way to collect social proof you can then, in turn, use in your subsequent holiday marketing campaigns across your owned and paid channels. 

Regardless of whether you can execute this strategy in-store or online, it’s a powerful way to show these customers that they’re special and you care about their opinion. 

Ready to take it one step further? Offer your VIPs an exclusive thank-you gift.

If you’re in the beauty industry, for example, you could give them a deluxe trial-sized skincare sample of your new line with their purchase.

Offering an exclusive item and letting your VIPs try it before the masses do helps you surprise and delight your customers, as well as boost trial and awareness of your new product line.

4 | Extend your holiday revenue-generating period with a BOPIS service

During the holidays, many people shop for gifts but don’t make the cut-off for standard holiday shipping delivery. And given the increased volume of online orders this year, it’s likely that shipping cutoffs will have to inch up a bit earlier on the calendar this year, too, in order for customers to receive their purchases in time for holiday celebrations. 

If you don’t offer expedited delivery or if you know your customers don’t want to spend extra for faster shipping, you can target shoppers who live near your retail store and offer a buy online, pick up in-store (BOPIS) or curbside feature.

By offering your customers an option to buy online and pick up their purchases either in-store or curbside, you can essentially turn your physical location into a fulfillment center, similar to what Best Buy is doing, to help you drive sales beyond any dates you may have to set for shipping cutoffs. 

This strategy will be particularly helpful to have on-hand in the event there’s a second surge of the virus—if customers can’t come into your store to safely browse due stay-at-home and social distancing requirements, then giving them the option to pick up online orders at your store can help you drive additional sales during the season. 

Once your customer places an order, you can send them an email letting them know when their order will be ready for pick-up at your store. 

Then, if your customers are able to safely come into your store and browse, they might make an additional purchase, too. Eight-five percent of shoppers make additional purchases in the store when they pick up an online order, according to Doddle

But if in-store browsing isn’t an option for your customers this year, you can lean into your online store to increase average order values

For example, you could email customers relevant product recommendations based on their behavior—previous purchases they’ve made, pages they’ve visited on your site, or items they’ve abandoned in their carts. 

To complement these product recommendations, you can also curate a collection of your best-sellers or create a holiday gift guide with your top recommendations. This will be useful for those people who you may not have much behavioral data about yet, too.

BOPIS offers can urge those last-minute shoppers to make a purchase if you can guarantee they’ll get their products quickly and conveniently in time for the holidays. But before you offer a BOPIS service, make sure you can logistically fulfill these orders or this can easily backfire and damage your brand reputation. 

5 | Segment your customers by geography and offer weather-relevant messages

Another way you can segment your audience is by where your shoppers live. This strategy enables you to offer relevant products and messaging to meet their needs.

Is a cold front coming to New York City? Feature your cold-weather mittens with a matching scarf in your emails. 

Did a heatwave just pass through Kansas? Feature an incentive like, “Purchase one pair of sunglasses and get $15 dollars toward a new hat.”

By highlighting products that make the most sense for each customer where they live at an immediate point in time, you show them that you’re in tune with their needs and you can provide them with valuable products.

Key takeaway

While these tips are helpful, the best piece of advice I can offer about planning for the holiday time period is to over-plan and to have a Plan B. While planning this year, in particular, may seem daunting, it’s the best way to set your brand up for success as you continue to navigate the uncertainty of 2020.

Like many brands saw at the onset of the pandemic, inventory can run out, supply chains can stall, websites can crash from too much traffic—and I know this from my own personal experience. 

Having a backup plan—like offering a gift with purchase or having a coupon code with supporting creative assets on hand—will go a long way toward saving you valuable time if something goes awry.

Consumers spent nearly $723 billion globally during the 2019 holiday season and online sales grew by 18.8 percent, so it’s certainly not the time to be scrambling and gambling with your potential revenue. Use these tips as inspiration to create a more personalized customer experience ahead of the holidays to help set your brand up for your best holiday season yet.

Want to set your brand up for a successful holiday season?

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