The Email Marketer’s Guide to Stellar Holiday Email Marketing Strategies in 2023

‘Tis the season to blend in yet stand out,

‘Tis the season to give back yet rake in the moolah!

‘Tis the season to fine dine, down wine, & be merry,

Bring out the carved pumpkins, turkeys,

Sweep in through streets in swag with the witches & wizards!

Decorate those fir trees with beautiful ornaments & ‘em baubles…

Yes, ladies & gentlemen, the merriest time of the year is just around the corner! Come Halloween, the 31st of October 2023, the living and the “dead” will gear up to kick off the Holiday Season ‘23 in style. And as email marketers, this is the season to make merry and laugh your way to the bank as Santa Claus slides down your brand campaign’s proverbial chimney too!  

In the comprehensive guide that follows, we will begin the spread by crunching some holiday season shopping numbers, proceed towards the spade work containing the pre-planning months, and finally cook up a delicious main course with unmatched tips, tricks, and strategies to kickstart your best ever Holiday season email campaign. Did we mention the festive sprinkling of beautiful holiday email inspirations as well?! 🙂

The Early Bird Gets The Worm ~ Deciding On The Best Time To Kickstart Your Holiday Email Marketing Campaign.

Before we begin decoding the perfect time to hit the gas on your stellar holiday email marketing campaign, let’s familiarize ourselves with some relevant numbers:

  • To quote the findings of the National Retail Federation (NRF), 61% of consumers began holiday shopping by the first half of November, while 57% preferred shopping online deals. 
  • According to Klaviyo, consumers who had already engaged with a brand’s previous marketing emails were 60% more likely to indulge in Cyber Weekend Sales. 
  • We know that a personalized email is the most reliable way to hearts and ultimately ‘em purse strings, but the percentages are crazy! 80% of consumers are more likely to seal deals with brands that deliver a personalized experience, and no, it’s not just limited to getting their first names right. Yep, you have to dig deeper and offer them coupons and product selections based on their browsing histories and preferences. 

Now those numbers speak for themselves. If you don’t capitalize on this segment of the last quarter of the year, you could leave easy money on the table! 

If you want to steer clear of that, the best time to start preparing your holiday season email campaign was yesterday, and the next best time is now! 

Since Halloween is just around the corner, you could start planning your holiday email campaign as early as August or September. Holiday shoppers with limited budgets and those ever-growing gifting lists begin anticipating good deals as early as October, long before the Black Friday shopping fever kicks in.

The dates also differ depending on your industry’s genre and bespoke marketing goals. Here are three pointers that one can consider before zeroing in on that perfect holiday email campaign launch date:

  • Based on your unique buying cycle: Ecommerce or webshop owners, you may consider building segmented email lists on the basis of the consumers’ buying behavior. Once you have categorical email lists based on the average time a consumer takes to complete a purchase, you can begin launching campaign funnels according to the anticipated buying cycle. For instance, if your usual buying cycle is a week or two long and you are targeting Christmas sales, it makes sense to launch the campaign somewhere between 4th & 11th December. 
  • Keep your buyers’ bespoke shopping behavior in mind: Depending on the current location of your target consumer’s journey in the purchase funnel (awareness – interest – desire – action), you can curate campaigns that target consumers at every stage of the proverbial sales funnel. You may begin with creating product awareness campaigns, delivering product benefits and specs, creating value for customers, and finally packing in a powerful punch with awesome discounts and deals that are too sweet to refuse!
  • Don’t forget to curate that post-holiday season campaign too! Once the Holiday season ends with a bang and a new year is in the offing, post-holiday email campaigns are a lovely way to nurture leads and deliver that sweet aftertaste that your long-term subscribers will enjoy. Keep them coming back for more in the coming seasons. 

We suggest that you fetch that pad & pen and make a note of the important holiday dates you wouldn’t wanna miss!

Halloween – 31st October 2023

Thanksgiving – 23rd November 2023

Black Friday – 24th November 2023

Small Business Saturday – 25th November 2023

Cyber Monday – 27th November 2023

Giving Tuesday – 28th November 2023

Green Monday – 11th December 2023

Christmas Eve – 24th December 2023

Christmas Day – 25th December 2023

New Year’s Eve – 31st December 2023

New Year’s Day – 1st January 2024

Killer Holiday Email Campaign Strategies That You Should Not Miss! 

People are in a festive mood; your emails should reflect the same. Right from “pun”tastic CTAs, and quirky subject lines to those oh-so-festive body copies and holiday theme templates, let your creativity & imagination flow unfettered and deliver a delightful consumer experience replete with those interactive elements as well!

  1. Begin With Segmenting Your Holiday Email Lists

The stepping stone to ensuring good conversions and high ROIs on your email campaigns is to segment your subscribers on the basis of the following factors;

1. Browsing preferences & history: Segment subscribers into separate categories based on their preference for particular categories, product collections, previous purchases, etc.

2. Seasonal versus year-round shoppers: Getting this differentiation right can help you cater to each category with the relevant content at the right time and set the perfect email cadence.

3. Coupon lovers: There is almost always a segment of shoppers who shop only when coupons are available. Identify this segment and indulge their shopping sweet tooth with a sweeter holiday season coupon.

2. Keep the Spooky, Quirky, and Emoji Quotient High


This email from 8 AM Creative had us hooked from the word go. The punny subject line (dockyard graveyard, you know!), the cute Casper emojis, and of course, the spooky story. Our team actually hit the CTA button because we wanted to “Keep Reading”! Everything in this Halloween-themed email is bang on, the orange, black, and grey color themes and the single-column layout; we truly scrolled till the end. 

  1. Try Asking Them a Question 

We love receiving gifts, but when faced with the question of looking for the perfect gift for our loved ones, we often draw a blank. Chances are high that those sitting on the other end of the screen are equally confused. Give them a chance to seek answers without having to pose a question.

You could begin by asking them, “Are you searching for the best Christmas gifts for your nieces & nephews?” or “Did you miss out on the Cyber Monday sales? We got you!”

  1. Spruce Up Your Email Visuals With The Right Sized Images & Holiday Themed Templates

The first thing most of us notice about an email is its visuals. Stick to regular-sized images, not larger than 600 pixels, as anything upwards of that doesn’t render well on desktops. 


This visual treat truly delights with just the right amount of festive cheer, Christmas decor, and sweet early bird and personality-wise treats. We truly loved it! 

  1. Deliver a Memorable & Personalized Holiday Email Experience

Whenever one comes across the term personalization in email marketing, every marketer worth their salt vigorously nods their head in affirmation. However, very few truly understand the essence of personalization. Getting the first name right is just the first impression; the concentric onion layers run much deeper. 

The idea is to strike a connection, build a solid rapport or relationship with the subscriber so that they not just engage with the brand but end up connecting emotion with the brand ethos! Sounds like tough work? Well, technology may help you only as much if you don’t delve deeper and peel back the layers! Find out their likes and dislikes, the way they feel about the content that you share, and the relevance that it holds for them. The greater the value you deliver, the bond engendered will stand the test of time and tide.

  1. Leverage AI to Add The WOW Factor

Email marketers can deploy the power of artificial intelligence to come up with catchy, creative, and fun subject lines that will reel them in. You could try using tools like Phrasee or SubjectLine to get those scroll-stopping hooks and catchphrases. 

Also, one could use AI tools such as Optimove or Dynamic Yield to curate personalized email campaigns that hit the bull’s eye with the right message, in the right tone, delivered to the intended person at the perfect time!

A parting caveat, if we may add, though these tools can help you with the spade work, we recommend running it through the experienced eyes of human copywriters who can add the perfect tinge of human emotion and wisdom to the copy! 


On that note, we would like to sign off with an off-key Happy Hanukkah Monica (inserts Friends reference!) 😉  Need help with coding the perfect set of holiday emails? Email Uplers is literally a couple of clicks away! Hit us up now! 🙂 


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