Boosting Holiday Sales with AI-Powered Engagement
Many brands are turning to AI-powered chatbots to automate self-service, providing quicker responses that meet the needs of busy holiday shoppers.
As the year draws to a close, many organisations will see employees take time off as they settle into the holiday season. With more time on their hands, and motivated by enticing sales, these same employees will transform into avid shoppers, presenting an unmissable opportunity for brands.
Between now and the start of the new year, retailers have their work cut out for them. While through the year, it makes sense for these brands to focus on building loyalty, dynamics shift drastically in this year-end season. McKinsey research indicates that 43% of US consumers would switch retailers for lower prices during the holiday season.
Far from seeing this as a threat, retailers should recognise the opportunity this shift presents. By engaging customers where they prefer to shop and managing interactions at scale, AI enables retailers to go beyond traditional approaches. In the past, businesses might have ramped up human capacity or hired temporary resources to meet demand. Today, they can achieve the same—if not better—results by strategically deploying AI solutions to engage customers and optimise operations.
Unmissable deals might pique the interest of prospective consumers, but turning clicks to conversions will take more than just rock-bottom prices. So, as we lead up to the holiday season, let’s explore key ways in which AI-powered engagement can help retailers drive exceptional customer support and sales conversations.
Always On Support
While shoppers may have their wish list of items well prepared ahead of the sales season, many will be swayed by unmissable deals on products they hadn’t previously considered. After all, while your current laptop might work perfectly, upgrading might seem all but logical when a cutting-edge alternative is dramatically discounted.
While the ability of attractive pricing to sway decision making is appreciable, taking contemplation to conversation often requires a fair amount of support – what are the warranty details, how long is the return period, if any? Shoppers, under pressure to capitalise on short term deals, expect assistance around the clock. However, given the number of digital channels available to consumers, retailers may find it challenging to offer quality omnichannel support.
Rather than missing out on the opportunity, many brands are turning to AI-powered chatbots to automate self-service, providing quicker responses that meet the needs of busy holiday shoppers. GenAI now makes it even easier for retailers to deploy chatbots that can be programmed with simple prompts, allowing them to respond effectively to various customer inquiries.
Retailers using AI-driven bots can swiftly address routine queries—such as store hours, product availability, and shipping information—ensuring shoppers receive immediate answers without delay. These AI tools can also capture basic information for more complex requests when human agents are unavailable, routing these to team members for follow-up while managing response time expectations.
Perhaps most critically, with AI-powered bots, retail businesses can provide 24/7 support, showing they are more proactive to consumer needs, moving shoppers down the purchase journey even during off-peak hours. This constant availability not only enhances customer engagement but also drives additional revenue by effectively doubling operational hours and capturing more opportunities to convert interactions into sales.
Personalised Customer Engagement
During the holiday season, shoppers are flooded with choices, making the experience retailers offer a key differentiator beyond product quality and pricing. I would even go so far as to say that today, personalising and understanding your customers based on their interactions with your organisation is no longer a novel approach—it’s an expectation.
Hyper-personalisation delights customers, with 77% of global consumers willing to share their information for a more tailored, value-driven experience. In fact, 84% actively seek deals and promotions this season. Retailers can get ahead by sharing personalised offers on customers’ preferred channels well before the holidays.
Powerful support platforms like Freshworks’ Freshdesk Omni enable retailers to segment audiences and create customised journeys, delivering timely, contextual messages based on user behaviour. For instance, if a customer lingers on a product without adding it to their cart, an automatic discount message can encourage action, guiding them toward a purchase.
Alternatively, AI-powered bots can offer personalised suggestions based on recent purchases or even recommend thoughtful gift ideas tailored to the customer’s buying history, creating a more engaging and revenue-driven shopping experience. This personalised approach keeps shoppers engaged, enhancing both their experience and conversion rates during the holiday rush.
Superior Post-Sales Support
Post-purchase engagement is equally vital to maintaining excellent customer relationships. The complications of holiday season shipping and delivery add a dash of volatility to customer expectations, which is why retailers need to double down on customer support and CX tech that improve it.
Modern support platforms can automate order updates and notifications on customers’ preferred channels. No matter the channel—WhatsApp, email, SMS, or the like—brands can trigger timely messages to inform customers when their order is shipped, picked up, or delivered. Proper and relevant engagement throughout the process not only keeps customers informed but also reduces unnecessary support tickets by pre-emptively addressing concerns. This creates a seamless, stress-free experience—an essential advantage during the already hectic holiday season.
Proactive order and shipment details are a win-win: Customers get peace of mind while companies deflect queries on order updates, allowing them to be as efficient as possible in a peak period.
Using AI to Mitigate the Return Rush
Impulse spending can lead to change of mind, which is why returns are an especially important aspect of peak sales seasons. Easily accessible return and exchange policies and business processes are essential for boosting customer confidence, with 60% of consumers in key markets like the US, UK, Germany, and Australia checking these policies before buying from a new brand. Traditionally, retailers streamline the purchase journey by clearly listing FAQs and return/exchange policies online, making them easy for customers to find.
With genAI, technology can analyse customers’ shopping history and product return data to proactively reduce returns. By identifying patterns like frequent size mismatches or high-return items, it can issue personalised warnings at checkout.
For instance, if a customer selects a size they often return, the AI can suggest alternatives or provide a size guide. Similarly, for items with high return rates, the system can display cautionary alerts, such as “Customers often find this product runs small.” These proactive measures not only improve customer satisfaction by guiding better purchase decisions but also help businesses lower return volumes, saving costs and streamlining operations.
If it does get to a return scenario, conversational AI can further enhance this process by identifying customer intent, suggesting relevant FAQs on returns and exchanges via website chat or in-app support, and even proactively offering assistance. Queries can then be seamlessly routed to support agents who handle returns, ensuring swift and efficient service that builds customer trust.
While facilitating a smooth exchange or return process can significantly impact customer satisfaction and loyalty, mitigating the scenario altogether is a smarter way to balance operational costs with the value of retaining happy customers.
Thriving through the Holiday Rush
As the holiday season approaches, the stakes rise for retailers aiming to turn fleeting interest into loyal customers. By integrating AI-driven engagement tools, brands can deliver exceptional, round-the-clock support, craft personalised experiences, and simplify post-sales processes. Each of these elements not only increases conversions but also builds trust, which is essential in a season where brand-switching is common.
Embracing these customer experience and AI strategies allows retailers to navigate the high expectations of holiday shoppers and set themselves apart, ensuring they end the year with stronger customer relationships and a solid competitive edge.
