Holiday Planning

Holiday Strategies to Engage Your Customers 

Because of rising prices and concerns about a potential recession, many people are more hesitant to shop this year. During Back to School, orders fell five percent, and conversion rates were also down five percent over last year.¹ People are spending more time researching and deciding whether to buy, which means that it will be even more important for brands to cut through the clutter.

Contact us to plan your holiday strategy!


Here are a few tips from the Ovative experts to put your customers first this season. To learn more about how you can prepare, read our Marketer’s Guide to Holiday 2022.

Tip 1: Understand Your Customer Segments

While every customer is unique, it is important to segment your customers this holiday to prioritize your marketing investment strategy. Understanding how your customers are impacted by the current economy, their needs, and how they will shop with your brand this season will enable your brand speak to them effectively.

What’s A Marketer To Do:

Based on our Enterprise Marketing Return (EMR) framework, our experts ask the following questions about customer lifetime value as they develop their key customer segments:

  • How will the economy impact each segment’s needs and shopping behaviors this season?
  • Do I know the value of each of my customer segments? Which customers are most important to engage this Holiday season? Which customers are likely to have large basket size, repeat orders, and high lifetime value? 
  • What are we doing to re-engage customers we acquired earlier this year or last holiday season? If we are only focused on new customers, are we missing retaining and reactivating past customers?

Tip 2: Personalize Your Messaging And Creative

As you develop your marketing strategy to focus on your highest value segments, consider how you can use distinct messaging and creative that feel personalized to each customer. Consumers are 76% more likely to consider purchasing from brands that personalize.²

What’s A Marketer To Do:
  • Dynamic advertising opportunities are rapidly increasing and improving in effectiveness across media platforms. Dynamic Ad Broad Audience (DABA) or Feed-Based Dynamic Ads can help ads resonate with the target shopper as they dynamically retarget someone with relevant creative and copy based on products or interests they’ve already browsed. 
  • In addition to dynamic ads, use channels that are aligned to you high-value customer segments. Here are example profiles of potential customers you might see this Holiday and ideas for how to reach them: 


  • The Frugal Shopper:

    This shopper is affected by the current economic climate but still wants to get something for their loved ones. Engage them with attractive promotions and category/product callouts as they passively browse through an Affiliate partner. Our Affiliate team experts suggest investing in highly incremental placement opportunities with loyalty partners like Rakuten Rewards, or content partners like Buzzfeed, to catch shoppers’ attention.
  • The Early Bird:

    These shoppers are primed to shop now. Create a seamless purchasing experience for them through social media or your own site experience. They also could be ready to cross gifts off their list but might not have the funds for all the gifts they want to buy. Showcase your ‘Buy Now, Pay Later’ or other flexible purchase options to enable shoppers to buy with you now.
  • The One Who’s Late to The Party:

    For these last-minute shoppers, provide them with quick and easy shopping options such as BOPIS (Buy Online, Pick Up In Store).
  • The Luxury Gift Buyer:

    These customers know what they want. Make sure your advertising copy and creative matches the terms they’re searching for with tactics like Google’s Response Search Ad Customers/Extensions and dynamic ads to capture this shopper before the competition.
  • The “Treat Yourself” Buyer:

    Many people also take advantage of Holiday to shop for themselves. Showcase a strong deal to this shopper, it could be the perfect reward for finishing their shopping to-do list.
  • The Comeback Kid:

    This buyer has been to your site before or bought from you last season. Don’t forget about them! Find opportunities to speak to them, continue to engage them, and encourage new purchases in their cart. Providing email / loyalty sign-up incentives can be a great way to engage this audience for communication all season long.

Tip 3: Tailor Promotions To An Early And Elongated Season 

Major retailers are concerned about a potential soft Holiday season;³ Target, Amazon, and Walmart all started Holiday promotions in October, to pull demand forward and elongate the season. In a recent survey, more than half (56%) of people said that they plan to shop earlier than they did in previous years due to concerns about the economy and a desire to take advantage of earlier deals.

Last year, when the season was elongated, we observed smaller YoY growth for key Holiday moments (Black Friday and Cyber Monday), and we anticipate that trend to continue this Holiday season. A longer season means that specific key dates will be less important, and brands need to be prepared to compete in the long game.

What’s A Marketer To Do:
  • Stay Nimble through the Long Season: Make sure you have developed and aligned with finance teams around multiple spend scenarios, so that you can be flexible and make quick decisions when there are opportunities to capture demand. Decide early on a desired return threshold and spend when your performance data shows that you could achieve it. Avoid holding a rigid budget for later in the Holiday season; if you can spend at or above your desired return, continue to scale your advertising early.   
  • Utilize Multiple Marketing Touchpoints: Conversion rates were down during Back-to-School season this year. We expect that to continue into Holiday. High prices and concerns about the economy are creating more hesitant consumers who are doing more research and taking more time to buy. We expect that sales cycles will be longer, and that people will require more marketing touchpoints before they make a purchase. Consider your customers’ journey and ensure that your brand is present throughout it.
  • Keep An Eye On Your Competitors: Understand your competitors’ positioning and keep track of when and what promotions they launch. People will be weighing their options and carefully considering value propositions, so it’s imperative that brands present compelling creative and messaging that clearly communicate the brand’s differentiators. 

Tip 4: Don’t Just Attract Customers; Make The Sale

Often, retailers and brands think of Holiday as a season to maximize traffic to their site. Too many marketers overlook eliciting action from shopper who get to their site.  Our Digital Experience Optimization (DXO) experts ensure that clients maximize every visit by designing intelligent digital experiences that enable easy browsing, purchase, and basket-building. Because conversion rates for retailers will likely be lower this year than they were last year, it will be even more important to create a seamless path to purchase to ensure that you don’t lose any potential customers to a poor site or app experience. With the looming threat of shrinking marketing budgets, brands can maximize their return of every advertising dollar through just small improvements to their site that increase conversion rate!

What’s A Marketer To Do:  
  • Align media creative to site/app landing experiences to provide customers with a seamless experience and reduce bounce rates. 
  • Analyze customer progression through key shopping funnel stages to identify the areas of your site/app that contribute to abandonment and lost purchases. Combine quantitative data with qualitative insights from session recordings and user testing to validate your assumptions. Understand how shopping behavior changes by time of day and adjust site experiences to reflect that.
  • Develop, prioritize, and test enhancements to your site/app using an effort vs. impact matrix to maximize revenue through the Holiday season. Test in advance of highest traffic holiday moments.
  • Solicit feedback from your site visitors so that you can identify ways to drive higher customer retention and frequency. 

As you prepare for this hectic time of year, remember to understand your customer, personalize messaging for different types of Holiday customers, prepare for an early and elongated season, and and optimize your site for conversion. 

For more on Holiday preparation and execution, download our Marketer’s Guide to Holiday 2022 or connect with us.  

Ovative is a digital-first media and measurement firm seeking to transform the measure of marketing success. At Ovative, we help brands move the needle. We are curious. We value your brand. We want to see you succeed. Connect with us to learn more!

1 | A Look Back on the 2022 Back to School Shopping Season, Rakuten
2 | The value of getting personalization right—or wrong—is multiplying, McKinsey
3 | Families Prioritize Back-to-School and College Spending Amidst Rising Inflation, National Retail Federation
4 | With Holidays Around the Corner, Minnesota Retailers, Shoppers Expect Less Gift-Buying, Star Tribune


Insights Team

About the Author

Ovative is a digital-first media and measurement firm seeking to transform the measure of marketing success. At Ovative, we help brands move the needle. We are curious. We value your brand. We want to see you succeed. Connect with us to learn more!

More Holiday Planning

Holiday Planning

Leveraging Influencer for Your Holiday 2023 Marketing Strategy

Learn tips for incorporating influencer marketing into your existing holiday strategy.... Read More »


Insights Team

Holiday Planning

Holiday 2023 Marketing Strategies by Consumer Type

Different messaging resonates with different audiences. Learn our experts’ tips and tricks for targeting different types of consumers this... Read More »


Insights Team

Holiday Planning

3 Holiday 2023 Profit Pressures to Prepare For

Learn about 3 major profit pressures affecting retailers this holiday season—and how you can leverage effective marketing strategies to... Read More »


Insights Team

accent bar