Navigating holiday sales with AI-first conversational support

Retailers can more easily handle the holiday shopping rush with generative-AI-powered customer support software

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Ida Jessie Sagina

Ida Jessie SaginaThe Works Contributor

Nov 02, 20235 MINS READ

It’s a yearly retail tradition: Deal-seeking shoppers’ activity spikes in the run-up to Black Friday, peaking on Cyber Monday. In 2022, Black Friday sales in the U.S. clipped $9 billion for the first time, and as of September 2023, Google’s consumer trends show that 35% of U.S. consumers have already started their holiday shopping, with that number climbing to 40% as of October.

While it may be daunting for retailers to handle the surge in interest, as Black Friday is also the time when shoppers aren’t bound by brand loyalty, a well-executed strategy could deliver higher sales. McKinsey research indicates that 43% of U.S. consumers would switch retailers for lower prices during the holiday season. 

As they approach the online shopping season, retailers can tap into modern technologies, including generative-AI-powered conversational support, to navigate the Black Friday rush.

From prompt customer assistance to additional revenue for the business, here are five ways AI-powered conversations can help retailers drive exceptional customer support during the busy holiday shopping season. For even more tips, check out our free holiday guide

1. Offer 24/7 support across customers’ preferred communication channels

Shoppers often expect brands to be available for online assistance around the clock. However, given the number of digital channels available to consumers, retailers may find it challenging to offer quality omnichannel support.

Brands can automate self-service using AI-powered chatbots to provide faster resolutions. And generative AI advancements allow companies to program and deploy chatbots with simple prompts. 

Retailers can use AI bots across their own website, live chat, WhatsApp, SMS, and other channels to:

  • Give immediate answers to simple customer queries, including store hours, product availability, and shipping information

  • Collect basic details for complex queries during non-business hours and route them to agents while setting response expectations

  • Surface relevant FAQs or policy documentation

  • Engage with online shoppers in real time to offer purchase suggestions and ease checkouts

Retail businesses that can provide 24/7 support show they are more proactive to consumer needs, moving shoppers down the purchase journey even during off-peak hours.

People-first AI is transforming service. Are you ready?

2. Respond swiftly to help customers successfully check out 

In the frenzy to grab the best Black Friday deals and make quick purchase decisions, holiday shoppers demand prompt support to their questions. In fact, 47% of U.S. consumers will abandon their online carts if they fail to find a quick answer to their questions.

Retail businesses can be better-equipped to give fast and contextual replies—during the holiday season and year-round—by adopting chat as a primary channel. 

With conversational support, retailers can:

  • Handle more customer queries concurrently and cut wait times

  • Create preset responses to commonly asked questions and expedite replies

  • Assign the queries to the right teams and provide super-quick answers

Additionally, with generative AI, retailers get an always-on personal assistant, such as Freshworks’ Freddy AI, that can help them craft higher-quality responses faster and improve the team’s productivity.

In one instance, India-based cosmetics brand Iba Cosmetics accelerated the query-to-order placement process with faster responses, directly increasing its conversion rates from 20% to 36%.

Read the free holiday guide to learn more: Unlock holiday support with AI 

3. Drive memorable experiences with personalized customer engagement

During peak holiday shopping season, shoppers are rich with choices. That’s why, beyond the quality and price of your products, the experience you offer can be the biggest competitive differentiator.

Customers delight in hyper-personalized experiences when they engage with brands, and 77% of global consumers are willing to exchange their information for a more personalized and value-driven experience. During the holiday season, 84% of consumers say they keep an eye out for deals, discounts, and promotions. Retailers can get a head start by letting their customers know of relevant offers and discounts on their preferred communication channel well before the Black Friday sales begin.

Powerful conversational support platforms such as Freshworks’ Freshdesk Omni allow retailers to segment users and set up personalized journeys to trigger contextual messages at the right time, based on website and mobile app activity. For instance, a discount message can automatically pop up for a customer who is looking at a product but is taking longer than usual to add it to the shopping cart.

U.S.-based online retailer BEL USA, which sells customized promotional items like mugs, tote bags, and pens, used conversational engagement to boost sales by nudging website visitors with useful information on discounts and promos. Their timely engagement saw a 28% response rate to personalized in-app messages, which was much higher than the open rates of their email notifications.

4. Keep customers informed with order updates

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 conversational 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.

Proactive order and shipment details are a win-win: Customers get peace of mind while companies deflect queries on order updates, allowing them to focus on revenue as opposed to customer service.

5. Make return and exchange policies easily accessible

Google research indicates that 60% of consumers in certain markets—including the U.S., the U.K., Germany, and Australia—check return policies before deciding to buy from a new brand. Companies can simplify the purchase journey by creating and indexing FAQs and return/exchange policies, and making them easily accessible online.

What’s more, retail businesses can tap into conversational AI to gauge user intent, recommend FAQs related to returns or exchanges via their website or in-app chat, and proactively ask customers if they need help. Queries can also be automatically routed to support agents who handle returns or exchange requests.

Keep the holiday cheer brimming with AI-driven conversational support

Black Friday and Cyber Monday are stressful periods for e-commerce and retail companies. But proper planning and the right customer service strategy, processes, tools, and resources go a long way in attracting and nurturing new and repeat customers. The post-holiday crush also offers a learning experience for companies that analyze support performance data to improve engagement and experience year-round.

With AI-powered conversational support, retailers can create seamless holiday shopping experiences by interacting with consumers on their favorite messaging channels, providing personalized recommendations, and offering helpful information swiftly. 

Download the free holiday guide to learn more: Unlock holiday support with AI

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