Ultimate Guide to Selling Through Holidays

Are you dashing through the snow on your marketing or sales “sleigh” to drive into the winter season? Or are you having no snow whatsoever but racking your brains on how to sell more on holidays in general, not only now?

Whichever relates to you, you’ve arrived at the right place.

Much like Santa’s sack full of presents for Christmas, this guide is packed with holiday marketing and sales trends, always-working tips, creative examples, and typical mistakes to beware of. And they are no joke: 75% of SMBs, in retail particularly, heavily depend on holiday customers. Here’s why. Holiday sales make up a quarter of annual revenues for 50%.

Besides, Deloitte forecasts a 7% to 9% rise in 2024–2025 eCommerce sales on holidays compared to 2023.

So, there’s no second to waste—delve into our bag, pick what suits your business, and pull out your perfect “gift” to maximize holiday sales.

What’s Trending in Holiday Marketing and Sales?

Let’s review the most impactful trends and examples of marketing and selling through holidays.

Gamification

Predominantly, gamified activities for holiday shoppers look like this (accompanied with CTAs):

• Game → Play our game—grab the reward!
• Quiz → Test your knowledge and win a prize!
• Wheel-spinning activity → Spin to win big!
• Challenge → Join the festive challenge—earn rewards!
• Scratching activity → Scratch to reveal your surprise gift 😉

For example:

SaaStr used a gamified spin-the-wheel popup on Cyber Monday for B2B SaaS lead generation.

X-day deals

The most common types are “12 days of deals” or “24-day advent calendar” campaigns, which are typically aimed at improving sales during winter holidays.

For example:

Last year, Digital Marketer offered 12 days of deals to drive B2B sales amid the Christmas holiday season.

Or consider the following email marketing example from Mirta with an advent calendar to pump up holiday sales. Such campaigns become even more effective when supplemented with dynamic pricing to adjust discounts dynamically.

Artificial intelligence (AI)

In fact, a massive cohort of retail executives (92%) said they planned to use generative AI for the 2024 holiday shopping season.

Just like many other brands, you can succeed in holiday marketing and sales with AI:

• AI tools for lead generation (e.g., LinkedIn Sales Navigator with new AI features)
• AI-powered chatbots for automated sales
• AI-generated holiday content
• AI for email marketing
• AI gift finders for holiday gifts

For example:

Tarte Cosmetics created an AI Gifting Assistant to give personalized product recommendations to holiday buyers.

Best Practices for Increasing Holiday Sales This Season and Beyond

Now, dig a little further and draw out the “evergreen” holiday marketing strategies.

Evoke FOMO with time-bound offers.

Hurry to read on and apply these tips to increase your holiday sales—the time is running out! (intentional FOMO here)

In the words of Julia Doak, Franchisor at Bedpost, “The fear of missing out, aka FOMO, is a universal psychological driver of sales, not only on holidays. But when you intentionally pinpoint it in holiday marketing, the chances are high to double or even triple your results. By and large, at Bedpost, this is all due to limited-time discounts on beds and mattresses during holidays.”

For example:

During the latest Black Friday sale on the website, the Bedpost team indicated the offer ends December 5 to induce FOMO in holiday customers.

Note: FOMO works brilliantly in email subject lines for holidays. Take a glimpse of these FOMO-provoking subject lines with a time limit from different brands:

• 💝 LAST CHANCE: Valentine’s Sale Finishes Tonight! – little whimsy
• Final Hours to Shop Mother’s Day Gifts – Gucci
• 👀 Final Warning ⏰ — Our Halloween Special Is Ending In 12 Hours – Dropship Breakthru
• 25% Off Everything Ends Midnight! 🎄📬 – Postable
• 🚨 Cyber Week Deal Ends Soon—Don’t Miss Out!  – RealEstateSkills.com

Marry holidays with giveaways.

Did you know that giveaways have a 34% conversion rate, higher than any other content type?

Although giveaways increase sales indirectly (first, they grow your email list on the website or follower count on social media), they become even more effective when married to holidays.

Max Tang, CMO at GEEKOM, believes a giveaway is a multi-purpose tool in holiday marketing and sales. “A holiday-themed giveaway captures user attention and engages users in a joyful interaction and celebration with your brand. More than that, the holiday season is often associated with generosity and warmth of gift giving, and giveaways help you tap into this sentiment. They, kind of, tune your brand into seasonal emotions.”

For example:

GEEKOM organized a Halloween-style giveaway with multiple prizes: a portable monitor, a keyboard + mouse set, and a $100 off coupon.

And here’s another holiday giveaway from Bucketlist on LinkedIn that is just in time for Christmas.

By the way, have you noticed that the company jumped on the holiday sales trend with not one but ten days of giving away (“X-day deals,” remember)?

Prepare exclusive offers for members only.

Just like FOMO evokes a sense of urgency and anxiety to lose an opportunity, member-only access hints at exclusivity and stimulates membership sign-ups.

While preparing exclusive deals for outdoor gear buyers on holidays, Matt Wouldes, Founder at Land & Sea NZ, explains, “Your consumers already have a shopping mindset during holidays, and exclusive promos nudge them to buy even more, making them feel special and valued and enhancing loyalty. Let alone that members spend more than non-members on average.”

He suggests rewarding your community members with:

• Holiday gift cards
• Member-only discounts
• Limited-edition gift sets
• Subscription perks for SaaS customers (e.g., an upgrade to a higher plan or a premium membership)
• Sneak peeks and behind-the-scenes content

For example:

On Black Friday, the Land & Sea NZ team rewarded customers with exclusive promo codes for members only.

As for event marketing on holidays, you can create VIP experiences, such as ticket discounts, reserved seats, meet-and-greets, etc. Similarly, a subject line like “Your exclusive holiday deal has arrived” can become the cherry on top of sales emails.

Create value-oriented holiday greetings.

Let’s take a wild guess: your customer greeting most probably goes like this on holidays: “Merry Christmas!” or “Happy New Year!”

An exclamation mark.

Nothing beyond.

If that’s so, how about adding a shared value?

It’s significant for nurturing leads and building customer relationships around common values as follows:

• Family
• Friendship
• Health and well-being
• Sustainability
• Social responsibility, etc.

For example:

Let’s sip from the experience of Greg Arnold, General Manager at Kitchen Mania, a family business of kitchen designs and installations. “As a family-built company, we prioritize family values that also resonate with our customers, especially on holidays like Thanksgiving or Christmas, when families gather around the table and feel a sense of togetherness and love. That’s the very sense we try to deliver in our holiday videos and greetings.”

Look at this video from the Kitchen Mania team on Christmas: “From our family to yours.”

Pro tip: You can also add value to subtle nuances like email sign-offs: “May your Christmas be filled with blessings” (the religious value) or “Happy holidays! May you and your loved ones be healthy and happy” (the value of health and wellness).

Involve influencers.

What if we told you that you can earn $6.5 for every dollar you invest in influencer marketing?

But back to holiday specifics: On Cyber Monday in 2024, social media influencers helped businesses generate roughly 20% of revenue via affiliate links.

Although Murtaza Oklu, Owner of OMO Transfer, didn’t participate in the latest Black Friday/Cyber Monday rush, he notes, “We smoothly moved from Halloween to Thanksgiving to Christmas this year hand in hand with influencers. Influencer-generated content for these holiday marketing campaigns ranged from Halloween-inspired T-shirts with our glitter DTF transfers to handmade gifts with our UV DTF wraps for Christmas. And they’re absolutely worth the investment. The key to remember is finding the right influencer, preferably from your niche.”

Indeed, OMO Transfer collaborated with several DIY content creators to generate more holiday sales this season. Instagram influencers also shared their unique discount codes with their followers on the platform to promote affiliate sales.

Choose strategic timing for sales calls.

“Call me after the holidays.”

This is perhaps the most dreaded and frequently heard objection in holiday sales calls.

Simon Healy, Director at Wardrobe Warehouse, says cold calling is a waste of time between Christmas and New Year’s Day. He shares, “We usually close our wardrobe showroom down on the last days of December and reopen at the beginning of January. There is no sales calling during this time of the year either. Calling on holidays is like building bridges to nowhere—it’s worthless.”

However, Toni Farrell, Marketing Manager at Coastal Motorhomes & Caravans, argues that the best sales call timing varies by business sector. “In our case, many people are eager to purchase motorhomes or caravans right before winter holidays to use them for holiday trips. Yet, spring holidays are particularly beneficial for sales calls in our market segment before the peak traveling time in summer.”

Pro tip: It’s always better to clarify your prospect’s availability and schedule calls with them beforehand. Whether via email or LinkedIn prospecting, offer your prospects to book a call two to three weeks before, mentioning that you don’t want to be a “holiday intruder” or “the mischievous Grinch stealing Christmas.”

Top 3 Holiday Marketing Mistakes to Watch Out For

Mistake #1. Leaving your website design untouched

Imagine that you’ve come to a holiday costume party without a costume. Everyone is shiny and festive, and you’re wearing routine clothes, just like yesterday, the day before, and the day before that day…

Think of your website as a holiday costume that can impress and cheer up your customers and even result in their impulse buying behavior.

In fact, exactly half of companies upgrade their eCommerce websites for higher sales before, during, and after the holiday season.

Nick Esposito, Founder at NYCServers, “Your website should be ‘well-dressed up’ for the holiday—no ifs, ands, or buts about it. Make sure to redesign the tiniest elements like popups, CTA buttons, animations, icons, and even the typography using Google Fonts to align with the holiday theme. It will help you improve the user experience and boost holiday sales.”

For example:

See how the Sender team revamped the popping-up lead magnet on the website for Christmas.

Mistake #2. Overlooking smaller holidays related to your niche

Again, just a gut feeling—

Do you actively sell only on high-profile holidays (Thanksgiving, Christmas, or Boxing Day, at best)?

John Grant, Founder & CEO of Premier Bidets, cautions brands against disregarding niche holiday marketing and missing out on its advantages. “It lets you market your product or service to a narrower but more engaged audience, gathered around a specific need, interest, or hobby. Naturally, you’ll stand out with less competition.”

For example:

On World Health Day, the Premier Bidets team encouraged their social media audiences to “splash” toward better hygiene and health with a proper bidet.

Here’s a handful of ideas for different industries:

• For tech companies and startups → World Innovation Day (May 17) 
• For travel agencies and hospitality businesses → World Tourism Day (September 27)
• For food brands → International Pizza Day (February 9)
• For digital marketing agencies → World Social Media Day (June 30)

You can also send cold emails or make cold calls on niche-related holidays, congratulate your prospects, and switch them to a holiday-buying mood.

Mistake #3. Overdoing it and getting into a PR scandal

Literally every brand tries to show off during the holiday season and use this chance to sell more.

Yet, you should remember: “The holiday season is a very sensitive time for brand reputation management, especially on social media,” pointed out Kathryn MacDonell, CEO at Trilby Misso Lawyers. “Reputational PR scandals can wipe out your marketing efforts, cut your holiday sales, or—worse—set the stage for a lawsuit against your company.”

A fresh example here is Coca-Cola’s AI-generated video for Christmas advertising. It brought “tidings of bad cheer” with mockery and disgust from social media users.

The lesson?

Be extra careful with AI or other tools, and use social listening to monitor your holiday campaigns on social platforms.

Sell Through Holidays Like a Pro

What fun it is to ride and read this holiday marketing and sales guide!

Isn’t it?

But the bells are already jingling, and it’s high time to act and implement all the tactics from this article.

Don’t forget to grab Skrapp along, a bulk email finder tool for looking up professional contacts. Sign up today to find prospects and turn them into customers.

Let your holiday sales soar higher than ever!