Chatbots and Checkouts

As the holidays approach, so do the decisions about where we’ll spend our shopping dollars this season and how AI-powered shopping is shaping those experiences. Recently, I purchased some home goods for my new house through Walmart’s online store. Unfortunately, my items never arrived. Trying to get help was nearly impossible since I couldn’t reach a human being. Instead, I was redirected to an online chatbot that struggled to understand why I wanted to return an item I never received. I kept explaining that it was a lost order, not a return, but the system didn’t grasp the issue.

This experience inspired my November blog series, which will focus on how to manage around AI-powered customer experiences. These systems are not going away; they are becoming the new normal, and we all need to learn how to navigate them effectively.

The upcoming themes will explore:

1. Use Chatbots for Product Discovery
Ask the chatbot for personalized gift ideas or product comparisons. Many bots can recommend items based on your budget, preferences, and purchase history, saving time and reducing decision fatigue.

2. Check Order Status and Delivery Updates
Use chatbots to track your packages in real time. A well-designed bot can provide shipment updates, estimated delivery times, and even handle rerouting requests if you’re traveling for the holidays.

3. Simplify the Checkout Process
Retailers can program chatbots to confirm that all steps of the checkout are completed, including payment confirmation and order numbers. This helps reduce the risk of failed transactions like the one I experienced.

4. Enable Smart Returns and Exchanges
Chatbots can guide customers through return or exchange options by automatically retrieving order information and offering instant shipping labels or store credit choices.

5. Leverage Chatbots for Promotions and Savings
Shoppers can ask bots for active coupons, bundle offers, or upcoming sales. Retailers can personalize these promotions to increase loyalty and repeat purchases.

6. Request Human Assistance When Needed
The best chatbots include an easy “talk to a person” option. AI should enhance, not replace, the human touch, especially for complex or sensitive issues.

7. Highlight Ethical and Sustainable Options
Retailers can use chatbots to showcase products made from sustainable materials or from companies with ethical supply chains. This helps shoppers make mindful choices that align with their values.

The Takeaway

AI is here to stay, especially in retail. As consumers, we can embrace AI-powered shopping tools to make our shopping more efficient, and as businesses, we can design smarter, more responsive systems that meet the needs of today’s digital shopper.

This holiday season, make your customer experience as seamless as your checkout process. CMA’s digital marketing team helps retailers use AI and automation to keep shoppers engaged long after the holidays are over.

Kim Kelley, Marketing Guru

Kim Kelley is the founder of Creative Marketing Arts, a California-based marketing agency specializing in digital strategy, experiential events, and community-driven campaigns. With over 30 years in the shopping center industry, Kim blends creative ideas with data-driven marketing to deliver innovative solutions for REIT advertising and brand engagement. With an eye for detail and a passion for results, she helps clients discover Out of the Box strategies that connect with audiences and build loyalty.

CMA partners with local and national brands to create meaningful connections that inspire action. The full service marketing agency proudly supports community causes, including the Homeless Assistance Resource Team (HART) and the Sacramento SPCA, by donating a portion of proceeds from every event to help families and animals in need.