When executed successfully, holidays are some of the highest revenue-driving times for businesses. But many businesses focus on year-end holidays with batch-and-blast campaigns targeting their entire audience. Holiday planning should be a year-round event focused on delivering personalized experiences to individuals on the holidays they care about.

This article will focus on delivering actionable insights around how businesses can strategize and execute successful holiday campaigns year-round.

We’ll discuss:

Key Holiday Trends of the Past and Present

When thinking about holiday trends, it’s important to look to the past to gain insights for the future, especially in retail. From year-round shopping to brand-centric holidays, the “holidays” no longer mean just the Black Friday and Cyber Monday sales leading up to Christmas. These traditional retail holidays are shifting in relevance and making room for burgeoning holiday trends throughout the year that drive business. But what are the reasons behind these changes and trends?

Changing Consumer Shopping Habits

As the years have gone by, single holiday events like Black Friday can no longer be the sole focus for marketers. Over the past two decades, we’ve seen the advent of a “holiday weekend” (the 5 days between Thanksgiving and Cyber Monday) for shoppers. This weekend packs in in-store deals, cyber deals, and even an emphasis on shopping local.

And even though the holiday weekend is still a big event, consumers have become more focused on shopping throughout the holiday season, not just on a single day. Convenience has become as important to them as price. They’ve also demanded more personalized experiences. Which means that they expect to have more opportunities to purchase (at an affordable price and in a convenient way) than just the last two months of the year.

A Year-Round Holiday Mentality

Because of the shift in consumer shopping habits, brands needed other ways to keep customers engaged. Not only that, but they needed to find ways to stretch their holiday success throughout the year.

So, brands turned to other special days throughout the year when they knew people would be shopping anyway and started creating marketing campaigns around them, like Mother’s Day and Back to School.

Then, when they ran out of special days, they started creating their own brand-centric holidays.

What exactly are brand-centric holidays? Chances are, you’ve seen several of them as subject lines in your inbox already this year. A brand-centric holiday is a marketing campaign that is focused on a niche holiday-like event. Think National Pet Day or National Pizza Day.

Consumers no longer had to wait for Black Friday or Cyber Monday to score huge deals. Instead, they could take advantage of the sales that happen around these year-round holidays.

The more competitive these holidays became among brands, the more consumers saw steep discounts and better deals. For some brands, these holiday deals were even better than their year-end sales and made a huge impact on revenue. And shoppers, always looking for both convenience and prices, took notice.

While the majority of holiday shopping still happens at the end of the year, it’s important to note the year-round trend of holidays. The more brands can identify which holidays are driving the best conversions and revenue, the better they can equip themselves to serve their customers.

Leveraging Historical Data to Improve Your Holiday Strategy

When thinking about planning your holiday strategy, it’s important to review more than just the year-end holidays. As discussed earlier, holidays are now a year-round event, and many major holidays are often regional – meaning if you put all your focus on one holiday, you may be excluding some of your audience.

Businesses should review their entire year’s sales and highlight holiday trends over the course of the year to identify where they’ll get the most bang for their buck. Here are a few tips for using historical data to create a fool-proof holiday strategy.

Review sales from last year (and the year before)

Before planning any strategy, it’s imperative to review your own historical data. Your customer data is your most important asset, as it can give you insights into your audience and their buying behavior. And because no two companies are the same, you should never rely on one-size-fits-all strategies. Instead, you should use your data to identify which holidays and which times of the year are most lucrative for your business.

Outside of just sales, it’s important to review your channel and campaign results. Which channels brought in the most traffic? Did you have more online sales than in-store sales? Dig into the data to find what brought you success and what fell flat.

And remember, just because something fell flat doesn’t mean it’s not worth trying again, but it’s important to review what happened and why it didn’t work.

Look for holiday trends (not just year-end holidays)

Dig into your year-round data. As discussed earlier, year-end holidays aren’t the only revenue drivers for many businesses. Look into your sales throughout the year and identify spikes that are associated with these brand-centric and niche holidays.

If Back to School campaigns perform extremely well for your brand, you want to make sure to set aside time (and budget) to focus on a campaign that kicks off the school year.

Pay special attention to these dates in the second half of the year, as many holiday shoppers no longer wait until Black Friday to start shopping. Also, identify what year-end sale days are your most lucrative. It’s important to identify when your audience is shopping with you and focus more time and attention on converting customers during those days.

Identify and Set Holiday Goals

Once you’ve reviewed your sales and campaigns, identify and set goals for the coming holiday season. It’s hard to understand how successful your company was without understanding what goals you’re trying to reach. Use the data from the last two years to set benchmarks for your team and identify areas for improvement.

Creating Year-Round Holiday Marketing Success

As marketers, we can no longer consider the holidays to only include the ones that happen at the end of the year. Customers shop throughout the year, and many wait for holiday deals to purchase items they’ve been eyeing. Holiday shopping has become a year-round event.

When it comes to sheer volume of spending, the winter holidays almost always win. But that doesn’t mean that there aren’t other lucrative holidays throughout the year that brands should be focused on.

According to Prosper Insights & Analytics Monthly Consumer Spending Surveys, US consumers planned to spend more per person on Back to College shopping than on the winter holidays. And Back to School shopping also carried a hefty price tag of $687.72 per person.

For the US, the above holidays are the most lucrative for retailers, and each deserves a brand’s attention. Whether it’s a full-blown marketing strategy or a simple campaign push, these are holidays that should be worked into your strategy during the year.

Not only that, but many holidays like Mother’s Day are celebrated at different times throughout the year depending on the region. So you may have to create separate campaigns for the different regions where your customers are.

Using post-holiday data to fuel your next campaign

Planning isn’t the only part of campaigns that should happen continuously throughout the year. As a marketer, reviewing campaign data and using it to optimize your next campaign is a must. When you’re planning a strategy for your next holiday campaign, look back at the data and use the insights to optimize future campaigns.

Beyond the previous year’s results, it’s also good practice to review the last holiday campaign you ran. Maybe that was a Back to School campaign or Labor Day sale. Either way, looking at the results from these campaigns can help you glean insights that can be used to improve the campaign you’re planning. Refining and optimizing campaigns are an important part of any marketing strategy.

How to Prepare for (Any) Holiday

Planning for any holiday campaign can seem stressful, especially the year-end holidays where it may feel like there is a lot riding on the success of campaigns. Let’s start to dive into how you can prepare for the impending holiday season and in turn, other holidays that lead up to (or come after) the winter holidays.

Analyze Your Audience

Before you do anything else, it’s important to analyze your audience. As discussed earlier, your historical customer data is your biggest asset, so use it! Understanding your audience and marketing to them in an appropriate manner is not only good practice, but customers now expect this from you.

Customers want you to know them and personalize your offerings to them. Even though you may have millions of customer profiles, you must find a way to treat each customer uniquely.

Your customers may share many common affinities – but that doesn’t make them the same. If you’re a sports-focused retailer, it’s safe to say that your customers are interested in sports, but that’s not the only way you should identify your customers. Instead, you need to dig further down into your data.

When you dive deeper, you’ll likely uncover more insights about their average lifecycles. You need to apply these findings to each campaign you run.

When analyzing your audience, keep these three questions in mind:

WHO is your target audience?

Before you plan a holiday blueprint for an automated email campaign or even a single social message, you need to understand WHO you are targeting. Maybe you want to target customers who purchased a certain product or more generally, anyone who purchased from you during the months of November and December last year. These audiences may seem the same at a glance, but when you dig deeper into their purchase intent, you’ll likely find that different things fueled their purchases and they need to be treated accordingly.

WHAT channels perform best with this audience?

Once you’ve identified the who, then look at which channels perform best with this audience. It wouldn’t make sense to create an all SMS-focused campaign for your top-converting email subscribers. Don’t let your gut tell you which channels these customers prefer — use data to identify those channels and then build your campaign around those.

WHAT does your audience expect from you?

As marketers, it’s our job to delight customers to the point of purchase. If you fail to do that, they’ll find a brand who can. Understanding your audience means more than just who they are, it means understanding what makes them purchase. If it’s personalized offers, make sure to tailor your campaigns. Whatever the WHAT is, take the time to plan it into your campaign.

Drive Omnichannel Success

Once you understand your audience (and in turn, the channels that matter to them), you must begin creating an omnichannel experience for your customers.

Customers no longer use one channel to shop. In fact, most shoppers switch between multiple channels and devices before making a purchase. Nearly 50% of shoppers use four or more touchpoints before making a purchase.

Not only that, but companies who deploy strong omnichannel strategies retain, on average, 89% of their customers. Consumers now expect the same brand experience across channels, and brands that deliver that are rewarded with customer retention.

Here are a few tips for creating an omnichannel strategy that engages your customers:

Consistent Experience Across Channels

Setting up each channel is the first step in creating an omnichannel experience. But after that, marketers need to focus on making their website, emails, social media, ads, and in-store experience feel consistent for customers. Your website should serve as the home base for all online branding. Anything that points back to your website should have the same look, feel, and messaging.

When it comes to your in-store experience, you should offer the same level of customer experience and personalization you offer customers online. Customers shouldn’t feel any disconnect between the experience they have with you online versus what they experience with your employees and products in-store.

Creating a Personalized Omnichannel Experience

Having a consistent message across channels isn’t enough to win customers — you have to personalize the experience for each customer. Personalization is a common topic among many marketers, and for good reason. Customers expect brands to treat them as individuals, and omnichannel marketing is not an exception to that expectation.

The best way to offer a personalized omnichannel experience is to collect and unify customer data in a single profile to get a holistic view of your customer. Unified customer profiles allow you to better understand your audience and create campaigns that serve them best.

Mapping online experiences to in-store experiences

It may seem easy to align your online channels, but what about your in-store experience? How can you give customers the same online and offline experience? For marketers, the answer lies in customer data and customer service.

Human interaction always adds a layer of personalization in-store, but marketers need to use data to offer additional services and incentives to in-store customers. When checking out, store clerks should collect additional data and offer perks. You can use this to tailor their future in-store experiences and also to further develop their unified customer profile to provide exceptional experiences online as well.

Take Holiday Personalization to the Next Level

Personalization should be a top focus for any holiday campaign. Customers demand more personalization, and this type of marketing leads to better experiences and, in turn, more sales. Here are 3 channels where you can take a more personalized approach to your holiday marketing.


Your website is most likely your most lucrative online channel. After all, your customers come to your website to learn more about products and ultimately make purchases. When thinking about creating more personalized experiences for your customers, consider your website as your most untapped channel.

Add personalization to your website by layering in widgets that focus on relevant ads for customers that recommend new products customers might like or products they’ve already abandoned.


Email is probably your best-converting channel, so why not take it a step further by adding personalization? Customers do a lot of research before purchasing, meaning they may come to your site and leave without purchasing. Take advantage of their browsing and buyer behavior by using that data to trigger personalized email messages.

Abandon cart and browse abandon emails are some of the best converting emails retailers have. Set up these triggered emails to automatically send after a customer has left your site. This keeps your brand top of mind and shows you understand what a customer is interested in.


As consumers, we are obsessed with our phones. Whether it’s shopping or checking social media, we spend hours on our phones every day. This makes mobile marketing a goldmine for marketers.

Mobile marketing offers a plethora of options for adding personalization. From in-app messaging to push notifications, mobile deserves attention from marketers. Using customer data, you can analyze mobile users’ propensity to buy and offer exclusive incentives via SMS or push notifications to mobile-friendly customers.

Leverage AI-Driven Strategies

AI-enabled marketing allows you to let a machine collect and analyze the data so you can focus on the who, what, and where of your campaigns. When you have data insights delivered to you, you can focus on the strategy, content, and creative of your holiday campaigns, rather than the mundane data collection many marketers find themselves bogged down by.

It also means you can let the machine help you personalize the customer experience. Here are two AI-driven strategies that can help you create a more personalized experience.

Re-engage defecting customers

Depending on your holiday strategy, you’ll likely have several different audience targets. One of those may be re-engaging defecting customers, while another may be targeting customers who spent a certain amount with your brand in the last year.

With AI-fueled tools, you can see your customers who are defecting and quickly re-engage them with personalized marketing campaigns. AI enables marketers to see and re-engage groups of customers, who have individual buying cycles, with a few steps, rather than creating and sending individual emails for each.

Predictive Product Recommendation

Using historical buying data, AI can actually predict and recommend products a customer may be interested in. These recommendations stand out because they actually take the customer into account. It’s true personalization.

Rather than have emails and website widgets that display ”recommended products” that are one-size-fits-all, you get products that are recommended based on browse and purchase behavior. When a customer sees products in line with others they’ve purchased, it’s a more personal experience for them and a better conversion opportunity for brands.

What Can You Do Right Now?

So all of this is great, but what can you do right now to set yourself up for holiday success? Check out these tips for setting up marketing campaigns now that you can start testing and refining for the upcoming holidays.

Automated Campaigns

One place to start is marketing automation. These are triggered events that happen based on customer behavior and offer a great way to move customers along in the buying process. Not only that, setting up these campaigns now allows you to begin to collect additional customer data and use it to refine your strategy before the holidays. Here are two campaigns you can set up that not only create a better experience for customers, but encourage them to convert.

Welcome Series

If you don’t have a Welcome Series yet, setting one up pre-holidays is a must. If you are trying to collect customer data, a great way to capture emails is with an incentive offer. Many brands who deploy welcome emails often see a large lift in subscriptions, meaning they’re an effective means of collecting data!

You’ve probably seen this across several of the websites you browse. It’s often a “Sign up for 10% off your first purchase,” or an offer of similar value. Once a customer gives their contact information, send them a welcome email with the offer included. Consider making the code only redeemable for a certain time period to make the most revenue in that period.

Quick Tip: Set up a segment of all new contacts with email addresses and create a triggered email that will deploy once this contact info is collected.

Cart Abandonment and Abandon Browse

Setting up cart abandonment and abandon browse emails enables the marketer to focus on personalization and re-engagement campaigns. It also helps drive purchases, making these campaigns a must-have for brands.

These emails are triggered when a customer abandons a cart with products in it or leaves a site after browsing without taking another action. Make sure the email includes the abandoned products and messaging tailored to the individual to make the message personalized and enticing.

Quick Tip: Set up a segment of all contacts who abandon a cart (or abandon after several product page visits) and create a triggered email that will deploy within an hour after this action is taken.

Website Personalization

We talked about the importance of personalization, but how can you add personalization to your website now that will keep you top of mind with customers come holiday season?

Predictive Product Recommendations

Adding predictive product recommendation widgets to pages is one way you can easily layer personalization into your website. When a customer visits your site, they will see a section titled “Recommendations for You.” The widget will pull in products that appear in this section based on browsing and purchase history, making it truly personalized to each individual customer.

You can also add single-product widgets on each page of your site. So as a customer browses your website, the products they’ve viewed or abandoned in a cart follow them around, keeping them top of mind and pushing customers to convert.

Quick Tip: Set up a segment of contacts who have purchased or browsed on your site. Then add a product widget to pages across your site that will pull in products based on customer behavior.

Related Content: 3 Powerful Website Personalization Examples That Will Instantly Boost Conversions

AI-Driven Marketing

You may be surprised to know that you can easily deploy artificial intelligence marketing to campaigns you already have deployed by adding a few special tools.

Send Time Optimization

When it comes to send times, many marketers spend a lot of time A/B testing to find the perfect time to send an email to their segments. But with Send Time Optimization (STO), emails are sent at the exact time a customer is most likely to open them. Rather than sending a large segment an email at 9:00 am on a Tuesday, this tool uses historical data to pinpoint which time is best for each individual customer. Utilizing STO in your email campaigns gives you the chance to begin maximizing open rates ahead of the holidays.

Open Time Content

For many marketers, getting an email opened is only half the battle. From there, you must have content engaging enough to garner a click. But if your email isn’t opened in a timely fashion, the offer might be outdated or the product no longer available. Open Time Content (OTC) allows marketers to create emails that change based on when and where it is opened.

Final Thoughts

When it comes to planning for the holidays, brands need to focus on these big events year-round. Brands who take the time to plan and strategize their campaigns are focused on using historical data to better serve their customer. This means they are creating campaigns that are personalized and matter to each individual customer. When you take a moment to step back and better understand your audience and their buying behavior, you’ll be able to create a successful holiday plan that you can use for year-round success and for holidays outside of just the winter months.

Dominate the holiday season in 2019/2020.