3 Emails to Send Now to Improve Your Holiday Campaign Results

8 min read

The holiday season is upon us, and your email marketing campaigns should be ready to engage your subscribers. Before Black Friday and Cyber Monday rush in, now is the time to optimize your email strategy with three key emails that can help boost your holiday marketing success.

Creating a holiday marketing strategy that resonates

The holiday season is the perfect opportunity to connect with your subscribers on a deeper level. Start by crafting a holiday marketing strategy that blends email marketing with your social media efforts. Your emails should tap into the holiday spirit while driving engagement across channels like TikTok, LinkedIn, and Instagram.

  • Segment your audience: Not all of your subscribers have the same needs during the holiday shopping season. Create custom segments based on past purchasing behavior, holiday shoppers vs. non-shoppers, or engagement with specific email content. This allows you to deliver more targeted, personalized messages.
  • Timing is key: Launch your holiday ads and Christmas campaign early enough to capture interest, but don’t forget the power of a well-timed follow-up closer to Black Friday, Cyber Monday, and the new year. Time-sensitive deals and reminders of expiring offers can create urgency and increase open rates.
  • Leverage user-generated content: Encourage your audience to share their holiday experiences using a branded hashtag across social media. Incorporating their stories into your emails—whether it’s a heartwarming moment or a creative use of your product—can humanize your brand and build loyalty.

Hot tip: Integrate email with social media to create a consistent experience. Keep the focus on what’s most relevant to your target audience—whether that’s great deals, thoughtful gift guides, or timely content.

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1. Re-permission Emails

Email permission can expire, and the holiday season is no time for deliverability issues. With subscribers losing interest or changing habits over time, inbox service providers (ISPs) take subscriber engagement into account when filtering or blocking emails. 

To keep your list healthy, sending a re-permission email is essential, especially to those who haven’t opened or clicked on your emails in the past 13 to 25 months. This approach makes sure you’re engaging seasonal shoppers who may only make purchases once a year.

However, keep in mind that your ability to track subscriber inactivity may depend on your email sending platform (ESP). Some ESPs don’t store historical activity data beyond 90 days, which can limit how far back you can look for inactive subscribers. In this case, an automated re-engagement email campaign can help. Instead of running a standalone re-permission campaign, automating the process ensures your emails reach disengaged subscribers on a rolling basis, without losing track of long-term inactivity.

Where you draw the line on inactivity also depends on your sending frequency. For example, brands sending daily emails may need to act after just six months of inactivity. 

Here’s an example of a re-permission email that Dell sent, urging subscribers not to miss out on Black Friday deals, a compelling motivator for them to stay engaged.

dell-repermission

If you’re looking for more tips on triggering emails to the right audience at the right time, check out our guide on trigger emails.

Boost engagement with personalized holiday emails

Personalization is critical during the holiday shopping season, especially when customers are flooded with promotions. Brands like Amazon, Macy’s, and Spotify have perfected the art of personalized emails by tailoring content to specific subscriber interests.

Here’s how to personalize your holiday emails for better results:

  • Use dynamic content: Incorporate personalized product recommendations based on a subscriber’s browsing or purchase history. During the holidays, people are shopping for loved ones—not just themselves. Highlight items that would make the perfect gift, and tie them to seasonal themes like Santa or holiday gift guides.
  • Behavior-triggered emails: Consider sending abandoned cart reminders or win-back emails to past customers who haven’t engaged recently. Showcasing what they last viewed with a special discount can prompt them to return. Use examples like Apple and IKEA, which send timely emails about recently browsed products to capture interest and sales.
  • Tailor subject lines: For holiday emails to break through the noise, your subject lines need to grab attention. Inject festive language, references to Santa Claus, or urgency for last-minute shoppers, such as “Still searching? The perfect gift is waiting!” Check out our best email subject lines for Black Friday and Cyber Monday for more inspiration.

Hot tip: Personalize every email with relevant offers, targeted product recommendations, and festive subject lines to stand out and drive engagement.

2. Win-back Emails

Reactivating inactive customers before the holiday shopping season kicks off can drive sales, especially with exclusive deals. Unlike re-permission emails, win-back emails focus on past customers who haven’t made a recent purchase. Offer them a compelling deal to get them shopping again.

For example, West Elm ran a win-back campaign with a subject line like “We miss us”—a common phrase used in win-back emails.

west-elm-winback-compressor

In the email body, they highlighted a 20% discount, making it easy for the customer to act. Personalized product recommendations based on browsing history added a final touch to encourage conversions.

Craft winning holiday emails and boost engagement

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3. Preference Update Emails

Holiday shopping behaviors change drastically, with customers often buying gifts for loved ones, themselves, or splurging on non-gift items. To stay relevant, ask your subscribers what they’re interested in with a preference update email.

A great example comes from Threadless, which used a sweepstakes incentive to motivate subscribers to update their preferences.

threadless-preference-update

This email helped Threadless personalize content, adjust frequency, and understand which social networks subscribers are active on, leading to more tailored future emails.

For more best practices, check out our guide on email personalization and make sure your emails feel personal and timely this holiday season.

Maximize post-holiday engagement for long-term success

After the holidays, many brands lose momentum, but this is a prime time to nurture relationships and convert one-time buyers into loyal customers. As holiday shoppers start to redeem their gift cards or look for post-holiday deals, keep your communication lines open.

  • New Year emails: Send a new year message thanking customers for their support during the holiday season, and invite them to shop for new arrivals or use their holiday gift card. This builds a bridge between holiday purchases and future sales opportunities.
  • Feedback and surveys: The post-holiday season is a great time to gather feedback on your customers’ experience. Send a preference update email asking about what they enjoyed most or where you can improve. Offering a discount or entry into a sweepstakes for their response, as Sephora does, can boost participation and help you fine-tune your holiday marketing strategy for the next season.
  • Re-permission campaign: Subscribers who didn’t engage with your holiday marketing campaigns might still be interested in future promotions. Send a re-permission email offering special discounts on post-holiday items to keep them on your list for the long term.

Hot tip: Post-holiday emails aren’t just for saying thanks. Use them to retain holiday shoppers and guide them into the new year with relevant offers and feedback opportunities.

Wrapping up your holiday campaigns with confidence

The holiday season is the busiest time of the year for retailers (and consumers!), and your emails are a critical component of your overall digital marketing strategy. Whether you’re sending re-permission, win-back, or preference update emails, these key touchpoints keep your subscribers engaged and ready to shop. By crafting thoughtful, personalized messages, you ensure your audience is primed for action during major events like Black Friday, Cyber Monday, and Christmas.

As you finalize your holiday marketing ideas, remember that your emails should align with the spirit of the season—and your brand. Use this opportunity to create meaningful connections, offer the perfect gift, and showcase the best of what your brand has to offer. With the right strategy, you can drive both short-term sales and long-term loyalty, ensuring that your customers remain engaged well into the new year.

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Chad S. White

Chad S. White is the Head of Research at Oracle Digital Experience Agency.