Top 7 ways to use chatbots to boost upsells & cross-sells in 2025

If you run an ecommerce store, you know the feeling. You’re getting traffic, you’re making sales, but you have this sense that you could be doing more with each customer. That the average order value (AOV) just isn't hitting the numbers you're aiming for. It’s a common frustration.

The good news is that AI chatbots are becoming a surprisingly effective way to tackle this. They're no longer just for looking up order statuses. Today’s chatbots can act like skilled sales assistants, having real conversations, figuring out what a customer actually needs, and gently guiding them toward a better, more valuable purchase.

This article is your guide to making that happen. We’ll walk through seven practical strategies to turn your chatbot into a tool that genuinely helps customers and, in turn, boosts your sales. And you can get started without the complicated, lengthy setup you might be picturing.

Defining upsells and cross-sells

Before we jump into the tactics, let’s make sure we’re on the same page. Using a chatbot to increase sales isn’t about being pushy. It’s about being helpful in the right way, at the right time.

Upselling is when you encourage a customer to buy a slightly better, more expensive version of what they’re already considering. Think suggesting the iPhone with 256GB of storage when they’re looking at the 128GB model, or pointing out the "Pro" version of an app that has a few extra features they might like.

Cross-selling is all about suggesting products that go well together. If someone’s buying a new camera, you might suggest a memory card and a tripod. If they’re buying a plant, you could offer a nice pot and some fertilizer to go with it.

So, what makes a chatbot better at this than those pop-ups we all reflexively close? It’s the conversation. A pop-up just yells an offer. A chatbot can ask questions, listen, and feel more like a helpful person in a store than an advertisement. This conversational style really works. In fact, research from Forrester found that chat-based interactions can lead to up to four times more conversions than static ads.

What makes a good upsell or cross-sell strategy?

Not all chatbot prompts work. A good sales suggestion is much more than just throwing a random product at a customer. The methods we’re about to cover are effective because they all share these four traits:

• They’re context-aware. The suggestion is directly tied to what the customer is doing at that very moment. It just makes sense, whether they’re looking at a specific item or are about to pay.

• They feel personal. The offer seems tailored to them, not like a generic message blasted out to everyone. It might use their browsing history to make the recommendation feel a bit more special.

• They’re helpful, not pushy.

  

  The offer is positioned as friendly advice that will improve their experience or help them get more out of their purchase. It’s about solving a problem for them, not just making a bigger sale.

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• They’re seamless. The whole process is smooth. A customer can add an item, ask for more info, or decline the offer with a single click, all without losing their place or getting frustrated.

A quick comparison of chatbot strategies

Here’s a quick overview of the strategies we'll be covering, so you can get a feel for which ones might work best for your store.

7 ways to boost upsells and cross-sells with chatbots

Alright, let's get into the specifics. Each of these can help turn your chatbot into a valuable part of your sales process.

1. Offer proactive recommendations based on user behavior

This is when your chatbot notices a customer spending a bit of time on a product page and proactively chimes in to offer help or suggest a related item.

It works because it’s both timely and relevant. Someone lingering on a page is clearly interested, and a well-timed message can feel just like a helpful shop assistant approaching you in a real store. You can set up your chatbot to appear after a visitor has been on a page for 10-15 seconds. It might say something like, "Hey! I see you're looking at the Pro Camera. A lot of people who bought this also grabbed our high-speed memory card so they'd never miss a shot. Want to take a look?"

To pull this off, your chatbot needs to know your products well. An embeddable tool like the eesel AI Chatbot can learn your entire Shopify store in just a few minutes. This lets it make smart, relevant recommendations right away, without you needing to manually program every possible product combination.

2. Suggest "complete the look" or product bundles

Here, the chatbot pops up with ideas for complementary products right after a customer adds something to their cart. This strategy catches the customer at their peak moment of interest. They’ve already decided to buy one thing, making them much more open to adding items that complete the set.

For example, if a customer adds a summer dress to their cart, the chatbot could suggest a pair of matching sandals. If they add a tent, it could recommend a sleeping bag and a lantern. The key is making the bundle feel natural and intuitive.

This requires a chatbot that lets you customize its flows. With eesel AI, you aren't locked into rigid, pre-made conversations. You can use a simple prompt editor to map out custom actions and dialogue, making sure the bot's suggestions and personality fit your brand perfectly.

3. Nudge customers toward smart premium upgrades

When a customer is viewing a product that has a "better" version, the chatbot can jump in to explain the benefits of upgrading for just a little more money. This is great because it cuts through the confusion of comparing specs. The chatbot can clearly explain the value of the higher-end product, helping the customer feel confident about spending a bit more.

On a product page for a "Standard" model, the chatbot could say, "Great choice! Just so you know, for only $10 more, the 'Pro' version includes [Benefit 1] and [Benefit 2]. Most people find it's worth it in the long run."

Many platforms box you into a one-size-fits-all approach to automation. In contrast, eesel AI gives you full control. You can decide exactly which products or pages trigger these upsell prompts, which means you can start small with your bestsellers and expand your strategy from there.

4. Use the "free shipping threshold" nudge

This one is simple but very effective. When a customer's cart is just short of your free shipping minimum, the chatbot points it out and suggests a low-cost, useful item to get them over the line.

Free shipping is a huge motivator in ecommerce. People are often happy to spend a few extra dollars on a product they want rather than on shipping fees. Your chatbot just needs to keep an eye on the cart total. If it’s $45 and free shipping starts at $50, it could pop up and say, "You're only $5 away from free shipping! How about adding a pair of our popular hiking socks to your order?"

5. Provide post-purchase cross-sell offers

Right after a customer completes their purchase, the chatbot can present a special offer on the confirmation page. Usually, it's for a related product with a small "thank you" discount.

By this point, the customer already trusts your brand enough to have made a purchase. They’re feeling good about their decision and are often open to a relevant, easy-to-accept offer that enhances what they just bought. On the order confirmation page, the chatbot could say, "Thanks for your order! As a small thank you, here's 15% off a protective case for your new device. This offer is good for the next 24 hours."

6. Create guided shopping quizzes

This turns your chatbot into a personal shopper. It asks a few simple questions to figure out what the customer needs and then recommends a handpicked set of products. This is perfect for industries with a lot of options, like skincare or electronics, or for people who are just browsing and aren't sure what to buy.

A chatbot on your homepage could greet visitors with, "Welcome! Looking for the perfect gift? Answer a few quick questions and I'll find it for you." It could then ask about who the gift is for, their interests, and your budget before showing a few tailored options.

7. Recover abandoned carts with a conversation

Instead of just sending an automated email later, a chatbot can talk to a user who has items in their cart but seems to be leaving the site. It can ask if they have questions or offer a small incentive to finish checking out.

This is a great way to deal with the common reasons for cart abandonment, like questions about shipping or hesitation over the price, right in the moment. An email can’t have a real-time conversation to solve a problem, but a chatbot can. If a user with items in their cart moves their mouse toward the exit, a chatbot can pop up and say, "Wait! Looks like you left something behind. Can I help answer any questions about your items before you go?"

This works best when the chatbot knows everything about your company. Some native AI tools, like those in Gorgias or Zendesk, are stuck with only the information in their own helpdesk. eesel AI is different. It connects to all your knowledge sources, including your helpdesk, past support tickets, and internal docs in places like Confluence or Google Docs. That means it can confidently answer those complex, last-minute questions about your return policy or product specs, which is often the final nudge a customer needs.

How to implement these strategies without annoying customers

Putting these ideas into practice is one thing, but doing it without driving people away is another. Here are a few tips to make sure your chatbot stays helpful.

• Focus on being helpful first. Always. Frame every suggestion as a way to make the customer’s experience better. Your goal is to be a helpful expert, not just another salesperson.

• Make it easy to say no. Nothing is more frustrating than a chatbot that won’t let you leave. Always include a clear "No, thanks" or "Not right now" button. Trapping a user in a sales pitch is a fast way to lose them for good.

• Keep it brief and conversational. Write like a real person talks. Use short sentences, a friendly tone, and maybe an emoji here and there. Steer clear of corporate jargon and long, robotic blocks of text.

• Test and simulate before you launch. A bad chatbot is worse than no chatbot at all. You need a way to see how your bot will react to real questions before it’s live on your site.

Final thoughts

So, let's wrap this up. AI chatbots can be a fantastic tool for increasing your store's average order value, but only if you use them thoughtfully. By focusing on helpful, relevant, and personalized conversations, you can guide customers toward better buying decisions that are good for them and good for your business.

The best part is that you don't need a team of developers or a months-long project to get started. The right platform makes it surprisingly simple.

With a tool like eesel AI, you can connect your knowledge sources, customize your chatbot’s logic using plain English, and go live in minutes, not months. Ready to turn your chatbot into your best salesperson?

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