Holiday Email Marketing Strategy Automation Guide

August 20, 2023
Written by
SendGrid Team
Opinions expressed by Twilio contributors are their own
Reviewed by
Ayanna Julien
Opinions expressed by Twilio contributors are their own

Holiday Email Marketing Strategy Automation Guide

Nailing your holiday email marketing strategy can feel like finding a polar bear in the snow. There's a lot on your to-do list, but we can help you refine your holiday email marketing with automation, know-how, and some best practices.

The holiday season represents a time of heightened anticipation—whether you’re a consumer or a marketer. For retailers, November and December account for about 19% of total annual sales. And the National Retail Federation estimates American businesses will earn over $960 billion during the 2022 holiday push. In other words, the stakes are high. 

There’s still time to formulate your email marketing campaign plan and get your sweet piece of the pie. With the right email marketing automation strategy, you can kick back by the fire in no time, sipping cocoa in fuzzy pajamas while the systems you’ve put in place execute your campaigns to success.

Before we jump into this article, read this piece first if you need a primer on what email automation is—and why you should use it.

Benefits of email marketing automation

Writing and sending individual emails in a series-long holiday marketing campaign can be a tedious, time-consuming process. However, the best email marketing campaigns are automated, as software now exists to free you from mundane execution-related tasks. 

Some of the critical business goals automating holiday season emails can help with include boosting top-funnel awareness, conserving resources, or setting a strong foundation for success in 2024.

1. Boost brand awareness in a personalized way

Get your brand name into consumer inboxes to stay top of mind as shoppers prepare their lists.

Due to its cost-effectiveness and reach, email remains the primary customer acquisition strategy for retailers over the 2022 holiday season—employed by 89% of large companies and 96% of small companies. And while social and text marketing remain popular, 70% of consumers say email is still their preferred channel for communication.  

2. Save time and money

With $36 returned for every dollar spent, email marketing provides cost-effective advertising. What’s more, studies show email automation increases productivity by 20%—giving you even more bang for your buck. With email campaigns running in the background, you’ll have more time to focus your attention on creative and strategic work. 

3. Build repeat success

Automated or not, building an email marketing plan does require time and effort. The good news is that your email marketing automation strategy is reusable. Save templates, process automations, and deployment schedules to use next Black Friday and Cyber Monday—or perhaps sooner with Boxing Day, Valentine’s Day, and Presidents’ Day sales right around the corner. 

10 automated holiday email marketing strategy examples

Your email marketing campaign plan may include a single type of email or many. Here are 10 inspirational holiday email marketing ideas to make your holiday season merry and bright.

1. Set up abandoned cart triggered workflows

Many automated emails are behavior-triggered, meaning a system tracks user browsing, clicking, and buying activities across your website and lets you know when to send marketing emails. For instance, you might set your system to send an abandoned cart email once one or more items have been sitting in the cart for 24 hours. 

Shoppers may abandon their carts for numerous reasons—better options elsewhere, a frustrating checkout process, a lack of payment options, or costly shipping, for instance. So in your abandonment email, consider including a coupon code or a free shipping offer to overcome objections. 

Plus, the festive holiday season has many consumers feeling generous. It’s an ideal time to reach out to contacts you haven’t engaged with in a while, as data suggests customer reactivation tends to increase starting around Black Friday.

2. Clean up and segment your contact lists

If you’re constantly trying to email invalid or inactive email addresses, mailbox providers may start sending your correspondence directly to spam folders. For this reason, cleaning your contact lists needs to be a priority rather than an afterthought. Of course, manual cleaning can be tedious and time-consuming work. 

Fortunately, you can automate:
  • Deliverability troubleshooting: With Twilio SendGrid’s deliverability insights, you can automate the email list cleaning process and identify problematic addresses before compromising deliverability. 
  • Customer segmentation: With SendGrid’s email list management, you can import customer data to gain full-picture visibility. Then, use these customer insights to create strategic segments. For instance, you might tag audiences into segments based on demographics, geographic location, topics of interest, or reward tier.
  • Engagement tracking: With SendGrid, you can track results to yield the best email marketing campaigns, as you’ll know when to send marketing emails and which messages are most likely to resonate.

3. Create a holiday email calendar and schedule your campaigns

By outlining holiday emails weeks, if not months, in advance, you can organize your teams and set the tone with consumers for a season of promotions, announcements, and communications. 

When to send marketing emails is a classic quandary. However, spacing out your messages results in a well-choreographed campaign you can dazzle and sustain captivation. 

For instance, you might create an email marketing campaign plan based on big sales days like Black Friday, Small Business Saturday, Cyber Monday, and Boxing Day. Or you might launch a “12 Days of Christmas” promotion sequence that runs daily throughout December.


Need help planning? Let SendGrid’s Email Marketing Calendar be your guide. Once you decide on a sending schedule, SendGrid provides 3 ways to advance-schedule your emails, whether through Marketing Campaigns, the SMTP API header, or the API itself.

4. Automate a welcome series for new subscribers

Personalized welcome emails boast an average 50% open rate, so consider this trigger a best practice in email marketing automation strategy. Beyond a thank you, your welcome email should, at the very least, provide an enticing nugget of valuable information and invite subscribers to browse. 

Consider this simple welcome email from Harry’s, a shaving kit brand for men:


Or you might decide to sweeten the email further with helpful tips, how-to tutorials related to a purchase, personalized content recommendations based on browsing history, or a special offer. Even an incentive as modest as free shipping can encourage seasonal buyers to spend 30% more. Check out Chapter 2 for step-by-step instructions on how to implement welcome emails with SendGrid. 

5. Establish a drip campaign around your holiday gift guide or e-book

Holidays offer unique opportunities to design and write creative content that shoppers find useful. For instance, an exclusive gated content download is a straightforward automation trigger where leads enter their contact information to receive access to a holiday gift guide. Did you know gift guides yield 48% more transactions than a typical promotional email? 

Check out this gift guide from Carter’s, which breaks down popular buys by category:


After giving consumers a day or 2 to digest your gift guide, you can continue your email marketing campaign plan by sending customer reviews and testimonials, related blog posts, or a special offer to solidify the sale. See Chapter 4 for step-by-step directions on how to set up a custom automation based on downloaded content. 

6. Send a thank you and share a deal

This time of year, everyone is looking for a deal—and a deal can be the difference between shopping with you and shopping with a competitor. It’s easy to get wrapped up in the bright lights—focusing all your efforts on shiny, new shoppers—yet keep in mind, existing customers spend 67% more on average than new customers, making them worth courting. 

That means keep tabs on your most frequent customers and big spenders. Show your appreciation by automating a purchase-triggered email that makes reward members feel like VIPs with exclusive, tier-based promotions and experiences. 

Need help designing your thank you message? Check out SendGrid’s free holiday thank you email template.


7. Boost engagement for your holiday event with a drip campaign

Want to plan an in-person event this year? Be sure to develop a fun email marketing campaign plan to build awareness and attendance. Your message should offer a preview of what shoppers can browse and what deals they’ll find. And these days, most emails also offer online shopping alternatives to in-person events.


As you can see with the example above, email is an excellent medium for breaking down complex promotional tiers ahead of time to help shoppers plan their strategies and alleviate confusion at checkout time. See Chapter 3 for details on how to set up your event promotion email series. 

8. Use holiday email templates with built-in personalization

Take advantage of email marketing templates to automate the design process. And within a few minutes, you can have the perfect holiday email ready to go, whether you’d like to promote gift ideas or offer last-minute discounts.


SendGrid’s email editor lets you build with drag-and-drop tools, code, or a hybrid. Plus, there are plenty of responsive holiday email templates to choose from, no matter your style preference.

9. Collect analytics data to identify top-performing emails

The email marketing campaign plan is only part of automation’s full range of value. Automation is about much more than simply scheduling and sending marketing messages. In fact, some of the most valuable automation work happens behind the scenes as consumers open, click, and browse your holiday marketing emails. The best email marketing campaigns are determined by data. 

With SendGrid’s email statistics, you’ll capture valuable audience insights, keep tabs on deliverability, and understand how emails perform. Not to mention built-in testing allows you to test different email subject lines, offers, and call-to-action buttons, making success repeatable.

10. Follow up after the holidays to encourage connection

It’s easy to think of December 25 as the grand finale of the holiday season—yet Google found 20% of online store traffic in December happens in the 6 days after Christmas. But before breathing a big sigh of relief, consider how you can keep the momentum of the peak shopping season going.

“Buy yourself the gift you didn’t get” promotions can be very successful, especially when paired with a special offer that encourages shoppers to treat themselves or purchase for the new year. 

See how slippers brand mahabis keeps the party going:


Best practices for your holiday email marketing strategy

  1. Start early: Plan your holiday email campaigns well in advance to ensure you have time to create compelling content and design.
  2. Segment your audience: Divide your email list into segments based on demographics, behavior, purchase history, etc. This allows you to send targeted and relevant content.
  3. Personalize content: Use recipients' names, past purchase data, and preferences to create personalized and relevant email content.
  4. Eye-catching subject lines: Create subject lines that are attention-grabbing and clearly communicate the value of opening the email.
  5. Mobile optimization: Ensure your emails are mobile-friendly since many recipients will open them on smartphones and tablets.
  6. Clear call to action (CTA): Clearly direct recipients on what action to take after reading the email. Make your CTA buttons stand out.
  7. Limited-time offers: Leverage the urgency of the holiday season by including limited-time offers and deals.
  8. A/B testing: Test different elements like subject lines, CTAs, and visuals to determine what resonates best with your audience.
  9. Cart abandonment emails: Send reminders to users who added items to their cart but didn't complete the purchase.
  10. Countdown timers: Use countdown timers to create a sense of urgency, especially for limited-time offers.

Automate your emails to boost holiday sales with Twilio SendGrid

From design to deliverability, Twilio SendGrid has all the email marketing automation strategy tips and tools you need to successfully navigate the holiday push. Spend a few minutes setting up and let our infrastructure take care of your campaigns.

For more email marketing campaign plan recommendations: With the holidays already underway, there’s no time like the present to get started. SendGrid’s Marketing Campaigns Free Plan lets you create a sign-up form, send single emails, A/B test, and automate up to 6,000 messages per month—free of charge. That’s right, scaling your email marketing automation strategy is affordable and easy. Contact our Sales team for details.

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