The Smarter Way to Cross-Sell and Upsell Online: Boost Revenue Without Losing Shoppers

Cross-selling and upselling are among the most effective ways to grow revenue without bringing in new traffic. The best stores use them to increase cart value by helping customers add complementary products and by guiding them toward higher-value versions of what they’re already considering.

But while the upside is huge, the execution often falls flat. Static product carousels, irrelevant add-on prompts, or pushy upgrade offers can feel disconnected from the shopper’s intent. Instead of driving more sales, they end up irritating customers.

Cross-Selling: Helping Shoppers Discover More

Cross-selling is all about showing customers products that complement what they’re already buying. Think coffee filters with a coffee machine, or a phone case with a smartphone. When it works, it improves the shopping journey and boosts average order value by leading customers to add more products to their cart.

How Cross-Selling Is Usually Done

In most online stores, cross-selling happens in predictable, static ways:

• Product page modules like “Customers also bought…”
• Pop-ups at checkout offering “commonly paired” items
• Bundle promotions created manually by merchandisers

The problem is that these methods rarely adapt to the individual shopper. They rely on pre-set rules or broad purchase data, not on the context of the current purchase. A shopper buying a coffee machine as a gift might not need filters. Someone buying sneakers for a child isn’t interested in adult shoe cleaners.

What should be a helpful encouragement often ends up as a missed opportunity - or worse, noise that frustrates the shopper.

Cross-Selling with AI Sales Agents

This is where conversational AI changes the game. Instead of relying on static rules or asking the shopper more questions, an AI sales agent can pick up context directly from the conversation and the way the customer described their needs.

If a shopper says “I’m looking for a coffee machine as a gift”, the AI already knows not to push filters - it can suggest gift-ready accessories like mugs or a premium blend instead. If someone asks about “lightweight sneakers for running”, the AI understands the use case and can surface complementary items like running socks or a water bottle.

By reading between the lines, the AI delivers cross-sell recommendations that feel natural and relevant, without forcing the shopper to do extra work. The result: more products in the cart, higher AOV, and a better customer experience.

Upselling: Guiding Customers Toward Better Fits

Upselling is about encouraging shoppers to consider a higher-value version of the product they’re browsing. A laptop with more storage, a mattress with higher-end materials, or a more premium skincare product. When relevant, upselling benefits everyone: shoppers get more value, and retailers drive stronger margins.

The challenge is timing and relevance. Traditional upsell tactics often feel pushy, like being asked to “upgrade” at checkout without knowing why. This can backfire, leaving customers annoyed or skeptical.

Upselling with AI Sales Agents

An AI sales agent makes upselling more natural by presenting it as guidance, not pressure. Through conversation, it can surface options that genuinely match what the shopper cares about:

"Since you'll be using this for travel, the next model up is lighter and has longer battery life." "For daily wear, this premium version has extra cushioning and is more durable."

This way, the upsell isn’t a random message: it’s a clear, context-aware suggestion that feels like advice. Shoppers feel understood rather than being sold to.

Smarter Recommendations, Happier Customers

Cross-selling and upselling aren’t new. They’ve always been part of retail, both offline and online. But what’s changing is how they’re delivered. Static modules and one-size-fits-all offers can’t keep up with customer expectations.

Conversational AI sales agents provide the missing piece: real-time, personalized guidance that feels natural to the shopper while driving measurable growth for the retailer.

When cross-selling and upselling are done this way, they stop being gimmicks and start becoming a real source of customer value and revenue growth.