How to Connect with Your Customers this Holiday Season

The holidays are fast approaching, and customers are getting ready to buy gifts for loved ones. This Black Friday and Cyber Week is set to grow 12% compared to last year, making it the biggest spending season on record. However, in order to achieve sustained growth, marketers must do more than just shout about their campaigns. As we head into an economic recession, driving loyalty and one-to-one messaging matters more than ever to connect with your customers across paid marketing channels and beyond. Quality marketing subscriptions ultimately drive more revenue through your owned channels

Depending on your brand and target demographic, holidays provide a great opportunity to connect with your customers and show them what you’ve got to offer. Not all holidays will be relevant to your brand, but celebrating those that are will build excitement and urgency. Utilize your text subscriber list this holiday season to connect with your customers on a personal level, and tell them directly what you’ve got to offer.


Reaching Customers With Holiday Text Messages

The bigger your subscriber list, the bigger your return. Consider sending those who opt-in to your text messaging services exclusive access to discounts, priority notifications on restocked items, and news about the latest holiday campaigns. The more subscribers you can amass, the better your one-to-one targeting and segmentation can be, so you can celebrate the right holidays with the right audiences. 

Quick Tip: Have a solid list? We suggest you aim to send 10-14 on-demand holiday messages to customers in November, and 7-10 in December.


Holiday Text Marketing Strategy Highlights

Be intentional when incorporating recurring sends into your on-demand text strategy–your ad tech should work for you to stay fresh and up-to-date with consumers. You can automate seasonally relevant text messages and promotional campaigns to your subscribers as frequently as once a week. However, get strategic with your segmentation so users don’t receive the same message twice. Through experimenting and testing, you can play around with different strategies to see which messages perform the best over the holiday season:

  • Simple and direct copy 
  • Use urgency to drive sales 
  • Leverage timers to drive urgency visually 
  • Create imagery to vary your messages by incorporating MMS through gifs and creative designs. 

Send Cyclical Holiday Marketing Messages to Customers

Gear your subscribers up for the changing seasons and temperature drops with seasonal messages. Use seasonal openers to send a lighthearted hello at the beginning of the new month or highlight exciting new products that have just hit the site.

October Seasonal favorites

If you’re looking for inspiration on how to connect with customers and tell your brand’s story then you’ve come to the right place. Here are a few of our favorite seasonal conversation starters for the month.

  • Get your subscribers in the Halloween spirit with on-demand texts such as:

“Halloween is almost here! If you’re still searching for a costume, we’ve got you covered. Reply with SCARY, SWEET, SILLY or STYLISH to find an outfit.” 

  • It’s Scorpio season, why not try: 

“It’s October 26th, and that means it’s Scorpio season. To kick it off, we’re giving you 10% off our Fall Favorites.” 

  • Other favorites include National Coffee Day, Mean Girl day, or World Smile Day:

“It’s World Smile Day, so we’re giving you something to smile about. Today, subscribers get free shipping on any order placed before midnight. Shop now.”

What’s on the calendar in November? 

Aside from just Black Friday and Cyber Monday, there are loads of holiday events approaching. What suits your brand? Happy hour day is perfect for alcohol brands, world vegan day for health and wellness, or international girls’ day for clothing or sportswear. Utilize awareness weeks with special offers to loyal customers, send zodiac-themed texts on a monthly basis, or simply build your brand storytelling by sharing tips and tricks relevant to the season. 

November Thought Starters 

  • Giving Tuesday – November 29th is Giving Tuesday. If your brand has a partnership with a non-profit, this is a great opportunity to promote that partnership and tell your customers if some of their spending with your brand is going to a good cause.
  • Movember – No Shave November is all month long, so brands with men’s grooming products can join in on the momentum with texts asking their subscribers if they’re participating.
  • Thanksgiving – This is a great time for brands to give thanks to their loyal customers and offer a discount to show appreciation to their text subscribers.

December Inspiration

  • 12 days of texts – Share twelve days of products with your subscribers in the days leading up to Christmas. 
  • Hanukkah & Christmas countdown – Convert last-minute shoppers with a shipping cutoff text. Give subscribers a date to order by to ensure they get their gifts in time. 
  • Holiday hangover – Message your subscribers between Christmas and New Years and encourage them to spend their holiday cash. 


Holiday text messaging is a powerful tool when it comes to reacting to current trends, topics, and moods; it’s key to accelerating eCommerce revenue. Gear up to get festive, and go above and beyond Black Friday and Cyber Week to connect with your loyal customers throughout the whole season. World Kindness Day, Small Business Saturday, or National Candy day — what’ll it be?


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Emily Black

Emily Black is a Senior Content Writer at Wunderkind.