Planning for the Extended Retail Holiday: 5 Tips from Top Retail Marketers

In a holiday that gets longer every year, it’s important to have a plan for every shopper throughout the season, from Black Friday to Green Monday — and that planning starts earlier and earlier. 

With a retail environment defined by inflation and persistent inventory issues, you might be preparing for the worst, but hoping for the best. However, the moments that will drive the most revenue are the moments that, in some ways, you can’t plan for. 

That’s why speed and flexibility are the name of the game this season.

By designing strategies to meet shoppers 1:1 at those on-the-fly moments that strike at just the right time — and by choosing quality over quantity — you’ll get the right shoppers to your site to convert from October through December.

In a special edition of our Coffee (ahem, cocktails) and Commerce roundtable, we sat down with retail marketers from Dick’s Sporting Goods, American Signature, The Gap, Vans, World Market and more to discuss strategies and campaigns to prepare for a great holiday (that will also protect the bottom line).

Here are five top insights from the discussion, complete with ideas and inspiration to drive profitability all season long.

5 Tips for the Retail Holiday Season

It’s not the size of the list, it’s the quality of the audience

The temptation to batch and blast across channels is strong, but size isn’t everything — what’s even more important are the behaviors of the shoppers on those lists. Naturally, marketing leadership doesn’t want to hear that people are getting cut out of a send, but the benefits of sending to those shoppers who are more engaged far outweigh the cost of not sending to people who are disinterested and may leave your list completely.

To drive the right traffic on email, use audiences that indicate a higher likelihood to purchase or a higher lifetime value. For those audiences that have a higher likelihood to unsubscribe, try sending 1:1 recommendations on paid media. Not only will this decrease the risk of an unsubscribe request, but it will give your paid media audiences that are familiar with your brand the nudge they need to come back and visit. 

Make your most expensive channels more effective

It’s no secret that paid media costs are rising, resulting in diminishing returns for retail marketers. One way to reach high-value customers is by increasing ad quality scores on Facebook. Facebook algorithms are actually counterintuitive to how marketers think in three key aspects:  First is what you’ll pay for an impression. Second is the kind of engagement you’re paying for — clicks, impressions, etc. And third is the creative value of your ad — are people liking, sharing, and commenting?

You can actually increase your score with the right targeting on social media. By targeting an audience with a high PCLV — those who are more likely to make a purchase — you can give your ads a higher engagement score, meaning you spend less for more. Once your score increases, move the ad to a broader audience to get more airtime on Facebook since at that point Facebook will be recognizing the ad as one that people want to see. That way, you can boost your acquisition strategy with more visibility.

The right triggers drive the most revenue

Triggers continue to be a powerhouse campaign for retail marketers, and acting on those in-the-moment behaviors is one of the keys to success this holiday season. Take cart abandonment campaigns: they continue to be one of the highest revenue-generating campaigns, but you have the opportunity to take them even further with the right prompts to supercharge those triggers. 

After last year’s inventory challenges, shoppers are more uneasy about the items they want going out of stock. By marrying products that are low inventory with your cart abandonment triggers, you can add an extra layer of urgency for shoppers to come back and complete the purchase before the product goes out of stock. This should also be leveraged for product abandonment triggers. 

You should take this further and create a trigger flow to make the most of those campaigns. If you pair your triggered emails with onsite campaigns, you can extend the inventory and product rec messaging even more urgently when your shoppers are online.

Drive the right site traffic — and stick the land

Catching shoppers at the right moment on email, Pinterest, Instagram, Google Search, or mobile is only half the battle — creating a site experience that closes the deal is key this season with the extended holiday. 

With all the high-quality traffic you’re driving with targeted audiences, you need to seal the deal. Leverage your site experience to be a conversion engine once your shopper clicks through. With 1:1 recommendations based on offer, product, and category affinity — plus inventory information and cart abandonment triggers — you can ensure that you’re always providing that extra nudge toward conversion. 

In a season of discounts, practice deal discretion

Shoppers are smart. They’ve been trained by each individual brand to know when the deal is coming so they get the best discount — and for retail marketers, it’s a race to get those dollars well ahead of Black Friday and Cyber Monday. 

But even though it’s the season of discounts, this year is all about protecting your bottom line. That’s why creating audiences that are more likely to convert with a discount will help you drive the discount-driven audiences when you need to, while holding those messages from other audiences when you don’t. 

Consider also what drives those audiences that might not be as discount-prone. What is the compelling thing that will get them to buy again (and again)? One key is product discovery through cross-category selling. This way you’re pulling shoppers in with value and products. To do this, send 1:1 cross-category recommendations to shoppers who purchased throughout the holiday season to encourage a quick return on a full-price item.

The long holiday season ahead — from Black Friday to Green Monday

Shoppers have been trained over the years to know when the deals are coming, but they’re starting to look earlier and earlier. For retail marketers, this creates a race to extend Black Friday deals, which have become a six-week event. That means it’s important to have compelling experiences that shoppers have come to expect in the period between the big holidays, from the Black Friday discounts to the BOPIS Green Monday. 

In a particularly volatile retail environment, it’s important to be prepared for anything. With campaigns that act on those in-the-moment shopper behaviors with compelling, 1:1 offers throughout the season, you can keep shoppers engaged until the new year (and beyond).