The holiday preparation is starting earlier and earlier with each passing year. This trend is a prime example of how the holiday marketing season has begun to take liberties with rewriting the calendar year.

The season represents a revenue goal line—make it or break it—for some businesses. That’s due to the recent, quiet rise of a new marketing phenomenon: Gray November.

Last year’s Gray November boasted $1 billion in online sales every single day of the month for the first time. Marketers are learning how to build and maintain an ample level of excitement throughout the month, rather than solely focusing on single-day events like Black Friday and Cyber Monday. The retail world is convinced that the energy of these days can be channeled and extended to cover the 20-plus days leading up to them. So, the question is: how do I ensure I make the most of Gray November without creating massive list fatigue?

Start with what you know

Email is meant to be segmented. Demographic data should be the first basic segmentation you look at to determine who should receive what kind of communication and, most importantly, when and how often. Browsing habits between men and women also vary substantially, so if you can infer gender from the products you sell and then track that through your customer database, then you have both a trend and an audience to create specific content and offers.

Email open rate is a leading indicator of engagement, but it’s not the whole story on whether or not someone should receive an email. Think of all the email that is deleted in under five seconds because someone opened it just to mark it as ‘read’ as they browse through their inbox looking for more high-priority communications. Sure, many emails are deleted on mobile devices by swiping left or right, but this ultimately degrades a sender’s reputation, according to the Gmail postmaster team. Marketers should be looking at opens and clicks as a further extension of engagement so that the passive openers can be segmented from the active openers who go on to follow a call to action through to the sender’s web page.

Preference centers are a great way to distinguish your most dedicated fans and brand ambassadors from your casual shoppers and detractors. Give people the option of increasing and decreasing messaging cadence and frequency. Learn to let the consumer drive the conversation—doing so will mean you do less “yelling” and engage in a more meaningful dialogue with them.

Email without A/B testing is like trying to hit free throws blindfolded

To snark or not to snark? Scarcity or abundance? Free shipping or deep discounts? Denigrate the competition or pretend they don’t exist? These are just some of the questions that A/B testing can answer. Consistent experimentation and testing of tone, style, images and conversions is a necessary and critical practice for all digital marketers to discover what really turns hungry eyes into actual clicks.

According to older, but still salient research, deep discounts trump free shipping, but not for every segment. Using past behavior to find the appropriate incentive to purchase is a crucial practice. Pricing and discount strategies constitute entire courses of study and focus. Finding the sweet spot that appeals to the shopper’s psyche is much more than simply choosing a round number that looks to be in line with every competitors’ discount.

One rule of thumb to follow when deciding on the kind of discount to offer is the rule of 100. If an item is priced below $100, consider offering a percentage discount. If the item is over $100, use a dollar value discount. $20 off on anything over $100 is less than a 20% off discount, but it crosses a psychological barrier: we all know the value of $20 and that appeal is powerful to consumers and doesn’t break the bank for businesses in terms of a profit margin. Again, test this—every segment and demographic will respond to pricing strategies differently. The only mistake is assuming that they won’t.

Starting with your deepest discounts on Nov. 1 may yield too low of a return on investment. Build awareness and anticipation by cranking up the heat and deepening the discounts as the month progresses. Be sure to consider activity, segment and loyalty as well. Maybe your most committed shoppers should reap the benefit of a deeper discount early on since they’re more likely to buy with less incentive while those on the fence need a solid reason to convert. Both of these are valid perspectives that will shake out through solid A/B testing.

Keep a record and check it twice

Email is a highly instrumented channel. The only way to avoid pitfalls and maximize razor-thin profit margins is learning from previous holiday seasons. The Gray November shopping season is not new—we’ve been doing this for nearly two decades without a designated name for it.

Keep notes of what is driving conversion throughout the holiday season so that you have this data available when you begin to plan the next cycle. Email is iterative, and for retailers, it’s cyclical and seasonal—you always have another bite at the apple, but only if you do your homework.


Opinions expressed in this article are those of the guest author and not necessarily Marketing Land. Staff authors are listed here.


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