Holiday Clienteling: How Retailers Can Sleigh the Holiday Season

Unwrap 7 clienteling strategies to boost holiday sales and customer relationships.

The front of a cozy retail store during the holidays

If you think about the upcoming holiday season as a bundle of stress, inventory management, complex merchandising challenges, and hoping to empty your warehouse of everything; you’re either Santa or you’re in retail. The holiday season—aka the most wonderful time of the year, aka the most stressful—can be a challenge for even the most seasoned seasonal managers.


Between the flurry of shoppers, the never-ending loop of Mariah Carey’s “All I Want for Christmas Is You,” and the pressure to hit those year-end sales targets, it’s enough to make anyone’s head spin. Luckily, there’s a strategy that can help you not just survive, but thrive during the holiday rush: holiday clienteling.


Clienteling is all about creating personalized, memorable shopping experiences that make your customers feel like VIPs. And during the holidays, when everyone’s on the hunt for the perfect gift, a little extra attention can go a long way. So, grab your hot cocoa, settle in by the yule log fire, and let’s unwrap some clienteling strategies that will help you sleigh this holiday season.

7 Strategies for Effective Holiday Clienteling

1. Personalized Gift Guides: The Santa's Little Helper Approach

We all have that one friend or family member who’s impossible to shop for—they’re usually called “mom.” This is where personalized gift guides come in handy. Instead of letting your customers wander aimlessly through your store (or website) like lost elves, create customized gift guides based on their past purchases and preferences.

Use your clienteling CRM to analyze customer data and suggest products that match their shopping history. For example, if Emily frequently buys cozy sweaters, you can send her a gift guide via email or SMS featuring your latest winter collection, complete with matching scarves and gloves. Not only does this make Sarah’s shopping experience easier, but it also shows that you know her tastes—making her feel special and valued.

Pro tip: Take it up a notch by offering a “Gift Wrapping Service” for the items in your personalized gift guide. Nothing says “I’ve got your back this holiday season” like taking the hassle of wrapping off your customer’s to-do list.

2. Holiday Shopping Appointments: The VIP Treatment

The holidays can turn even the calmest shoppers into frantic deal-hunters. The solution? Offer holiday shopping appointments that give your customers a more relaxed, one-on-one shopping experience. Think of it as the retail equivalent of a FastPass at Disney World—bypassing the lines and getting straight to the good stuff.

During these appointments, your associates can provide personalized recommendations, help customers find the perfect gifts, and even set aside popular items that are flying off the shelves. It’s like having a personal shopper without the luxury price tag, which really is at the heart of holiday clienteling. Plus, this approach allows you to manage store traffic, ensuring that everyone can shop safely and comfortably—even on Black Friday.

To sweeten the deal, consider offering a small perk for booking a holiday shopping appointment, like a complimentary holiday treat or a discount on their purchase. It’s a win-win: customers get a stress-free shopping experience, and you get more engaged, satisfied shoppers.

3. Digital Wish Lists: The High-Tech Santa’s Sleigh

A digital wish list is the modern-day equivalent of writing a letter to Santa, except ecommerce is real (unless you’re under 6 reading this blog, then of course Santa is real). Encourage your customers to create and share their wish lists with friends and family—this not only makes holiday shopping easier for them but also drives traffic to your store.

Use your clienteling platform to send personalized reminders to customers who have items lingering on their wish lists. “Hey, Tim! Don’t forget that new pair of boots you’ve been eyeing is still available, and it’s perfect for those winter hikes you love.” You can also offer exclusive promotions on wish-listed items to nudge customers towards making a purchase before the holidays.

And here’s the kicker: when a customer’s loved one purchases something from their wish list, send a “thank you” message from Santa’s workshop (or your store, whichever you prefer). It’s a fun, festive way to keep the holiday spirit alive and well, while also encouraging future wish list usage.

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4. Personalized Holiday Greetings: The Warm Fuzzy Feeling

The holidays are all about spreading cheer, so why not send personalized holiday greetings to your customers? Through your CRM, you can craft messages that speak directly to your customers, referencing their past purchases or favorite products. Check out some of Our favorite holiday templates as jumping off points.

For example, “Happy Holidays, Jane! We hope you’re enjoying the cozy blanket you purchased last winter—maybe it’s time to add a matching throw pillow to your collection?” A little personalization goes a long way in making your customers feel appreciated, and it can also serve as a gentle nudge to revisit your store for more holiday shopping.

Don’t forget to include a small incentive, like a discount code or free shipping offer, to encourage them to stop by. After all, who can resist a festive greeting paired with a deal? It’s the retail equivalent of a holiday card stuffed with cash—always appreciated, always in style.

5. Follow-Up After the Purchase: The Gift That Keeps on Giving

Holiday clienteling doesn’t end when the purchase is made—it’s just getting started. In fact, you want your holiday clienteling to give way to simply year-round clienteling. After a customer completes their holiday shopping, follow up with a thoughtful message to show that you care about their experience and their satisfaction.

For instance, “We hope you’re loving the new jacket you picked up! If you have any questions or need help finding more winter gear, we’re here for you.” This approach not only reinforces the relationship between your brand and the customer but also keeps the door open for future purchases.

Additionally, consider sending a post-holiday thank you message to your top customers, along with a sneak peek at upcoming sales or new arrivals. It’s a great way to keep the momentum going into the new year, ensuring that your holiday shoppers become year-round loyalists.

6. Surprise and Delight: The Unexpected Holiday Gift

Who doesn’t love a surprise? During the holiday season, go the extra mile by surprising your best customers with unexpected perks. It could be something as simple as including a small freebie with their purchase, like a festive ornament or a sample-sized product. Or, you could offer an exclusive invitation to a VIP holiday shopping event, complete with treats and special discounts.

The key here is to make the surprise feel personal and tailored to the individual customer. For example, if you know that a customer loves your store’s signature candle line, slip a mini version into their bag with a note saying, “Just a little something extra to brighten your holidays!”

These small gestures create memorable shopping experiences that your customers will associate with your brand long after the holidays are over.

7. Social Media Clienteling: The Instagrammable Holiday Experience

Social media is the new mall—it’s where your customers are hanging out (but without the hungover Santa)—so meet them there with some holiday clienteling magic. Use platforms like Instagram and TikTok to showcase your holiday collections, share gift ideas, and engage with your followers through interactive polls, Q&As, and live shopping events.

You can even offer personalized shopping advice through direct messages, helping customers find the perfect gift or answer questions about products. It’s like having a digital concierge that’s always on call, ready to assist with all their holiday shopping needs.

And don’t forget to encourage your customers to share their purchases on social media with a branded hashtag. It’s free advertising and a great way to build community around your brand during the holiday season.

The holiday season is the perfect time to up your clienteling game and create shopping experiences that are as memorable as they are merry. So, as you deck the halls and prepare for the busiest time of the year, remember that a little extra attention can go a long way. By focusing on personalized, customer-centric experiences, you’ll not only boost your holiday sales but also build lasting relationships that carry over into the new year. After all, there’s no better gift than a loyal customer.

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We’ve pulled together 24 holiday clienteling ideas that will help you delight, engage, and wow your customers throughout the festive season.