Part 2:  Plan like a Pro: The Definitive Holiday Email Marketing Guide (Clone)


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 
  • Part 3: Content Management: How to Elicit Emotions with Creative & Engaging Emails & Final Thoughts (Coming Sept 21)


Deliverability: Rock Solid Thoughts to Land Your Emails in the Inbox 


6. Buy Deliverability Equity

When it comes to the world of email deliverability – the ability to deliver email newsletters into the inbox – one of the most important things is having clout with the various email clients out there – this can be the difference from getting your holiday email into an inbox versus a spam box.

So, before the holiday rush do yourself a favor and buy deliverability equity. And before you begin searching for the sign-up link for an annual plan let me say deliverability is hard. The good news about this important email marketing commodity is that it is free! No credit card required. But there’s only one way to get it – throttle and send your email marketing campaigns with best send practices. You might be able to re-engage some lapsed customers, but don’t wait until the last week before December to warm up your inactive emails. Now is the time to segment and figure out who you can email to.

Pro Tip: Regardless of the holidays, when it comes to lapsed campaigns, you want to figure out when that proverbial lapsed cliff is for your brand and then set up your automated lapsed campaigns to run a week before the subscriber starts lapsing and churning. In addition, I recommend updating this email – be it with new products or a recent article – once a month.


Ensure you’re hitting the inbox of your subscribers this holiday season.

Let Webbula help you! Download the Complete Guide to Email Hygiene. 


7. Get Replies, Not Clicks, from Inactive Subscribers

When someone replies to your email, that sends an excellent signal to the Gmails and Yahoos of the world. So, expounding on the previous point, now is the perfect time to reach out to your lapsed segments and find out what they’re looking for. 

Don’t try selling them or getting them to click. Better yet, try getting them to reply to your emails. Ask them how you can be of better service to them; ask them what first brought them to your site; engage with your customers. Besides getting excellent customer feedback from a valuable customer demographic, you’re also signaling to email clients that you’re a legitimate sender – and that will help you inbox during the holiday season when your email marketing will be in fifth gear.

Pro Tip: Afraid that your customer success team will become overwhelmed with emails? Well, no one says you need to elicit a response from 100,000 subscribers. Start off small – work with your teams – to understand what a reasonable number of extra incoming emails are and then work from that point. And yes, every reply to an email marketing newsletter sends a positive response to the email client provider.



Check with the Experts: Inactive Email Subscribers to Send or Not to Send


8. Segment and Target

Don’t be afraid to cut your losses. Don’t just send blindly with one-off campaigns for your entire list. You must segment your list to ensure you’re not getting into any honeypots (not good). This might not be a popular opinion, but a while back, I was asked about what a good open rate is. My response was something along the lines of the open rate is fictitious. You see, I can guarantee a 75% open rate, although, the target send will be to 50 of the most active subscribers. The point is by segmenting you can finesse your open rates. Having said that, one should aim for over 20% and try to enlarge the list as much as possible. 

And when it comes to targeting, make sure you are showcasing your best storefront to everyone on an individual level – leave the one-and-done display windows to brick and mortar storefronts.

Pro Tip: Some ideas for segmenting could be either by customer LTV (lifetime value) or by email score. If you opt for the email score, first send out campaigns to the subscribers with higher scores – that is they have a higher propensity to engage – and then to the lower engaged. 


9. Check Your Spam Folder

I’m sure you’re receiving your company’s newsletters to your business email, but do you have seeder lists? You should. And you should monitor these to ensure your emails don’t land in the spam folder. One of the worst indicators that email clients get is if an email consistently lands in the junk mail box without anyone caring. Clicking on that “Report not spam” button sends a powerful message to the email client.


10. Hire Santa or Become an Elf!

Did you ever consider hiring Santa to send out your emails? Or if you don’t have the number to the North Pole, consider your spokesperson to volunteer as one of Santa’s helpers! Of course, I’m talking about replacing the sender name with something that’ll easily create a holiday experience so you stand out in the inbox. One caveat before all your holiday email campaigns are sent from Santa Claus: see the last tip in this article before determining if this is a good strategy for your brand.

Pro Tip: Be sure to get your company logo or spokesperson portrait in the company sender email address. This will ensure your emails are easily recognizable in the inbox. For more advanced tips consider upping your email marketing game and get DMARC and BIMI certification.


11. Pattern Interruption

The fact is people aren’t opening the majority of emails this holiday season (or for that matter, any season), so it’s imperative that you snap out of the mundane with some good pattern interruptions. 

Try sprinkling emojis in your subject line. Not surprisingly, the Christmas Tree🎄, Santa Claus 🎅, and a Wrapped Gift 🎁 were the most popular emojis last year. 

Here’s another tidbit about emojis: most Jewish holidays don’t have a holiday-specific emoji, but nothing screams Hanukah more than this 🕎 emoji! And if you’re still prepping Thanksgiving and Black Friday emails, be sure to push the turkey 🦃 and shopping bags 🛍️ the whole nine yards.


12. Negative Space in Your Inbox

Take a look at your inbox and what do you see? If you’re looking at your emails on a desktop, by my estimate you’ll see around 83% of the screen taken up by dates, from names, subject lines, and of course preview text. 

In an attempt to make the inbox look full, email clients like Gmail and automatically pull in the first few lines of your email and nestle it in as “preview text.” That’s a whole lot of text! And while emojis do a great job at pattern interruption, negative space can help draw eyes to your message. 

The good thing is that many email service providers – like ActiveCampaign, GetResponse, and MailerLite, to name a few – let you customize this space with your preview text. Either way, full translates to cluttered. So, this holiday season, try standing out in the inbox with negative space. 

Pro Tip: If leaving multiple spaces in the preview area in your campaign builder doesn’t achieve the desired result, simply enter the ‌ tag – this should do the trick!



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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