Back when I first launched my online store, I was thrilled just to get sales.
I didn’t care if someone bought a $5 eBook or a $99 bundle — a sale was a sale, and I celebrated every ping like it was Christmas morning.
But then I noticed something: I was leaving money on the table. Big time.
Someone would check out with a low-ticket item, and that was it. No follow-up. No suggestion. No nudge to buy something else. I’d worked so hard to earn that sale but once they bought, I basically ghosted them. Total rookie move.
That’s when I discovered automation for upselling and cross-selling and it changed the game.
What I Wish I Knew Sooner About Upselling & Cross-Selling?
Let’s get one thing straight: upselling and cross-selling isn’t about being pushy. It’s about relevance. You’re helping customers discover more value — and if you do it right, they actually appreciate it.
Here’s how I define it (real-world style):
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Upselling = encouraging customers to upgrade or choose a higher-end product
(“You bought the basic planner? Cool. Here’s the full productivity system with bonus templates.”) -
Cross-selling = suggesting complementary items
(“You bought a recipe book? Here’s the grocery list pack that goes with it.”)
And automation? That’s what turns these strategies from a manual hustle into a smooth, hands-off system.
Step 1: Use Email Automation After Purchase
One of the easiest wins I ever had was setting up a simple email flow: right after someone bought my digital planner, they’d get a follow-up email suggesting the “advanced” bundle — same planner, but with training videos and a Notion version.
Conversion rate? Around 12%.
That may not sound crazy, but when you’re sending that to hundreds of buyers, it adds up fast.
Here’s how I structure the email:
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Email 1 (Immediate): “Thanks for your purchase — here’s how to access your item.”
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Email 2 (Next day): “Want to get even more out of your purchase?” → upsell
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Email 3 (2–3 days later): “People who bought this also grabbed…” → cross-sell
Pro tip: use tools like Mailchimp, Klaviyo, ConvertKit, or MailerLite to trigger these flows automatically based on the product someone purchased.
Step 2: Use In-Cart and Post-Purchase Upsells
I used to think the checkout page was sacred — don’t touch it, don’t distract the buyer. But I was wrong. Turns out, in-cart upsells work great if done right.
Here’s what worked for me:
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In-cart bump: Right below the product, I added a checkbox: “Add the 20-page workbook for just $5.”
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Post-purchase thank you page: After the order went through, I offered a one-time deal: “Want the full workshop replay for 50% off?”
That last one pulled in an extra $200 in the first week alone. All automated.
Most eCommerce platforms (like Shopify, Payhip, or ThriveCart) let you set this up with just a few clicks — no coding required.
Step 3: Use Behavior-Based Triggers
This one’s next level — and so worth it. I started tracking what people clicked on in my emails and store. If someone clicked on “Course A” but didn’t buy? They’d get a follow-up email the next day saying, “Hey, noticed you were checking this out — got any questions?”
If they bought “Course B,” they’d get a cross-sell 3 days later: “Here’s the workbook that pairs perfectly with Course B.”
Tools like ActiveCampaign, Drip, and Klaviyo are great for this. You can tag users based on clicks, product views, and purchase behavior — and trigger personalized messages without lifting a finger.
Step 4: Bundle and Discount Smartly (With Automation)
Bundles are your upsell superpower. But instead of offering them to everyone, I started using automation to offer bundles only to repeat customers or those who bought a certain product.
I used ConvertKit to tag buyers of my digital course, and 10 days later, they’d get an exclusive bundle offer for the course + templates + coaching session. The email subject was: “You’re gonna love this next step…”
That campaign brought in a 19% conversion rate, without any discounts shown publicly on my site.
Step 5: Don’t Forget Your Abandoned Carts
Okay, this one isn’t just about upsells but it’s where I accidentally added a cross-sell that worked like magic.
In my abandoned cart sequence, I added a P.S. that said:
“P.S. People who liked this also grabbed the productivity habit tracker — you can add it to your cart in one click.”
I didn’t expect much from it, but it turned into a top-performing cross-sell. People who were on the fence now had two things to get excited about.
Final Thought: Automate Like You’re Helping, Not Selling
Here’s the truth: automation doesn’t replace relationships — it enhances them when done right. Upselling and cross-selling through automation isn’t about squeezing every penny. It’s about guiding people to the next best thing for them.
When someone buys from you, they’re saying, “I trust you.” Automation lets you respond by saying, “Here’s something else you might love — no pressure.”
Set it up once. Watch it run. Then focus on building even more cool stuff to offer your customers.
Because once the machine is running? That’s when the fun really begins.
