When I first started selling digital products, I was happy just making a sale.
One product, one customer, one order. Simple, right?
But then I noticed something on Amazon. After I added a book to my cart, it suggested another book, a workbook, and even a Kindle version. Suddenly I was checking out with three items instead of one. I realized something big: I didn’t need more customers. I needed to sell more to the ones I already had.
Enter: cross-selling and upselling. These two strategies completely changed how I structure my offers and boosted my average order value without needing a single extra visitor.
What’s the Difference?
Let’s keep it simple:
Cross-selling = Suggesting a related product. (Think: “You bought the planner — want some matching stickers?”)
Upselling = Offering an upgraded or higher-priced version. (“Want the premium bundle with coaching included?”)
Both are about helping your customer get more value. It’s not about pushing, it’s about guiding.
If you want a deeper dive into how these two strategies work in real life, check out what cross-selling is and how it works.
When to Offer Upsells or Cross-Sells?
I’ve tested this a lot, and here’s where they convert best:
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On the product page — A section that says “Pairs well with…” or “Customers also bought…”
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During checkout — This works really well when it’s low-friction. One click, no extra info needed.
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Post-purchase thank-you page — A “special offer” after the sale can bring in more.
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Email follow-ups — Some people just need a day or two before saying yes to the add-on.
I once added a “matching workbook” as a cross-sell right below my product description. Conversion jumped 17% on that offer alone. It was just sitting there — now it’s my top bundle.
Want to know exactly when and where these strategies work best? These 11 case studies of successful upsell strategies break it down beautifully.
How I Set It Up? (No Fancy Tools Needed)
I use Payhip, and here’s how I set it up:
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I created bundles: For example, a “Content Calendar + Social Media Template” pack.
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I used the cross-sell section on my product page (Payhip has a built-in feature for this).
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I added manual links in my email thank-you messages: “P.S. Want the Canva version too?”
If you’re using Shopify or WooCommerce, there are apps and plugins galore — just don’t let tech overwhelm you. Keep it simple.
You can also explore how to create product bundles from someone who messed it up first to avoid common mistakes I ran into.
Tips to Keep It Helpful (Not Pushy)
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Make sure the offer fits what they’re already buying. A customer buying a fitness planner probably doesn’t want a meal prep guide unless you connect the dots.
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Show the value. Instead of “Add this too!” say “Most buyers get better results with this workbook.”
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Keep the design clean. Avoid popups that block the cart or slow down checkout.
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Limit choices. Three or fewer options = better decisions.
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And yes, use urgency sparingly. “Limited-time upgrade” works great. “BUY NOW OR LOSE EVERYTHING!” not so much.
Want an emotional edge? Learn about the psychology behind successful upselling to connect more meaningfully with your audience.
Use Email to Upsell Too
Here’s my favorite automated flow:
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Email 1 (Immediately after purchase): “Thank you! Your download is ready.” + P.S. “Want to upgrade to the full toolkit?”
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Email 2 (2 days later): Highlight a case study or testimonial of someone who bought the upsell.
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Email 3 (5 days later): Last chance to grab the upgrade, offer a small discount or bonus.
These emails run on autopilot. I set them up in ConvertKit, but you could use MailerLite or any basic tool that allows automation.
You can get even more tactical with how to upsell in email marketing, especially if you’re running automations.
Track What’s Working (and What Isn’t)
I made the mistake of offering everything to everyone — and my cart page became a mess. That’s when I started tracking:
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Average Order Value (AOV) — If it’s going up, your offers are working.
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Conversion Rate on the offer — Is your upsell getting clicks but no sales? Maybe it’s too expensive or unclear.
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Refund requests — If they go up, you might be pushing too hard or confusing the offer.
One tweak that helped? I moved my upsell after checkout instead of on the cart page. Felt smoother, and my AOV still improved.
Final Thoughts
Cross-selling and upselling aren’t just about making more money, they’re about serving your customers better. When someone says “yes” to buying from you, it means they trust you. Why not guide them toward even more value?
Start small. Add one related product to your checkout page. Create a bundle. Send one follow-up email. Test. Tweak. Repeat.
It’s not about pushing more products. It’s about solving more problems and that’s how you grow with integrity.
