Part 1:  Plan like a Pro: The Definitive Holiday Email Marketing Guide



23 Proven Tips to Help You Cruise into the New Year

Table of Contents
  • Part 1: Preparation: Plan Like a Pro
  • Part 2: Deliverability: Rock Solid Thoughts to Land Your Emails in the Inbox (Coming Sept 14th)
  • Part 3: Content Management: How to Elicit Emotions with Creative & Engaging Emails & Final Thoughts (Coming Sept 21)


Holiday Email Marketing Will (Once Again) Be Relied on  

The winter holidays – culminating with New Year’s Day – are coming up fast and furious. It seems that fall is the quickest season, and for good reason. Marketers are keen on turning over a new leaf, eyeing a shiny winter holiday promotional season. And once Halloween sales zip by, Thanksgiving and Black Friday sales begin, which ultimately morph into Christmas, New Year’s and Winter sales.

With that in mind, here are 23 email marketing tips to help you dominate the email marketing holiday season and allow you to cruise into 2023 in style!


Holiday Email Marketing Preparation: Plan Like a Pro


1. Understanding the Calendar

Yes, we all have our ways of knowing how many days October, November, and December have, but do you know what day of the week October 1st is this year? How about Halloween? Black Friday?

Well, if you have not yet checked, Halloween falls on a Monday and Black Friday will be on November 25th. And as the calendar goes, this is on the earlier side. For marketers, the longer the holiday marketing season is the better – remember, every single day counts. 

But back to the calendar, be sure to understand how things fall; view it as one big block and infuse that into your emails. For example, if you’re heavy on content, think about an overall story arc your emails can take. If you’re sending daily emails, consider adding in a daily countdown to New Year’s Day. Either way, know the calendar and plot out your plan accordingly.


2. Weekend Bonanza

Looking towards December, you will notice that Christmas and New Year’s Day both fall out on a Sunday. Depending on your business, this could either be good or bad; however, if you are prepared then this should not matter. Just take this into account as you prep your email marketing holiday calendar.


3. Major (and Minor) Winter Holidays

While Christmas and Kwanzaa are set firmly in the Gregorian calendar at the end of December, the Jewish festival of Hanukah is not. The 8-day holiday is based on the Jewish calendar, which fluctuates annually. This year, Hanukah begins on Sunday evening, December 18th and officially ends on December 26th, but you’ll want to make sure you get your emails out sooner than later. 

Another bonus that planning affords is the ability to be creative! Sure, you can run a special sale for the first day of winter (December 21st), but don’t forget the lesser-known days like to offer free shipping on National Package Protection Day or offer free cookies on Gingerbread House Day (yes, both are real days). Alternatively, make up your own holiday – think Festivus – if it suits your business goals.  


4. Party Like It’s 2021

For better or for worse, we’re creatures of habit. As marketers, we can capitalize on those tendencies – i.e., shopping habits and sales – by looking at data from 2021. In lieu of a crystal ball, I recommend looking at email marketing data and actual e-commerce purchases to try to guestimate when the big windfall of sales will come. 


Pro Tip: Don’t be lackadaisical about results. Be proactive and put these numbers up on a dashboard and then start plotting this year’s figures when they become available. This way you’ll know if you’re on or off track. Remember, when January arrives there will be nothing you can do about Q4 numbers!


5. If You Can’t Beat’em, Join’em

I don’t know who said it first – I recall hearing it from the mouth of Kermit the Frog – but if you can’t beat them, join them! By this I mean join your competitors’ newsletters and see what they are sending. Naturally, once you’re on their lists, stay on them and keep your eyes peeled to see what they’re doing and use this to help you plan out your email marketing calendar. And I don’t mean just perusing their emails – take diligent notes and try to really learn from them. 



About the Author


Shmuel Herschberg - He is a frequent contributor to the Webbula blog. 

Shmuel Herschberg is a seasoned digital marketing executive, who lives and breathes email marketing. He is the founder of Shyn Media (, a boutique agency that offers creative marketing automation, content strategy, and digital media services. 

Shmuel possesses a unique blend of technological awareness coupled with strategic thinking and customer psychology. This enables him to translate customer needs into actionable, winning strategies. Contact him today and see how he can power up your email marketing game in only 15 minutes!  


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