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Home E-commerce

11 Case Studies of Successful Upsell Strategies (That Actually Worked)

by Ethan
April 17, 2025
in E-commerce
Reading Time: 5 mins read
11 Case Studies of Successful Upsell Strategies (That Actually Worked)
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Once I started selling my own digital products, I realized upselling isn’t about tricking people.

It’s about helping them get more of what they actually need. The trick is doing it in a way that feels helpful, not pushy.

So I started testing. And failing. And tweaking. And eventually, I found a rhythm that worked. Along the way, I studied other brands — big and small — and took notes on what they did right.

This post is a collection of 11 upsell strategies that actually worked. These aren’t just theories — they’re real examples with lessons you can steal. Whether you’re selling physical goods, online courses, or digital downloads, you’ll find ideas here that are tested and proven.

1. Amazon’s “Add Protection Plan” at Checkout

This one’s sneaky smart.

Right when you’re about to hit “Buy Now,” Amazon offers a protection plan. It’s low-cost, high-margin, and super timely. The offer only shows after you’ve already committed to the main purchase — which makes saying yes way easier.

Takeaway: Offer small, relevant add-ons at the final checkout stage when buyer intent is highest.


2. Canva’s “Pro Elements” for Free Users

I noticed this while designing a client’s Instagram post.

As a free user, you can access Pro design elements — but when you try to download them, boom: you’re hit with an upgrade prompt. It doesn’t block you before designing, only when you’re emotionally invested.

Takeaway: Let people experience the premium value before asking them to pay more. It’s a tactic that aligns closely with the psychology behind successful upselling.


3. Digital Course + Workbook Bundle (My First Win)

Okay, this was mine.

I had a mini course on productivity, priced at $49. I added an optional $19 workbook as an upsell — nothing fancy, just a one-click “add this workbook to your purchase.” About 1 in 4 people took the offer. Easy money.

Takeaway: Don’t overthink it. Pair a core offer with a logical upgrade — even something simple. This is exactly what I covered in how to create product bundles from someone who messed it up first.


4. Gymshark’s “Complete the Look” Upsell

After adding leggings to my cart, I got hit with a styled outfit suggestion — all matching items.

It wasn’t just random. It was built around what I already picked. It made me think, “Well… if I’m getting the leggings, I might as well get the matching top.”

Takeaway: Use visuals and context to recommend complementary products, not just more stuff.


5. Payhip’s “Add a Coaching Call” Upsell

Saw this while buying a PDF template from a digital creator.

After checkout, she offered a discounted 30-minute strategy call. Same branding, same vibe. Felt like a premium touch — not a hard sell.

Takeaway: Add a personal touch or service as a post-purchase upsell. People love access. If you’re using Payhip, check out how to create automated upsell funnels on Payhip from trial to triumph.


6. ThriveCart’s One-Click Upsell Funnel

ThriveCart lets you stack upsells after the main purchase — and I’ve seen creators use it brilliantly.

One marketer I follow sells a $27 ebook, then offers a $97 course as a follow-up with just one click. It’s seamless and doesn’t feel spammy because it’s all value-aligned.

Takeaway: Post-purchase upsells can feel natural if the timing and offer align with the buyer’s intent. For more ideas, check out these 9 best upselling techniques for online stores told from experience.


7. Starbucks’ Upsize Prompt

Classic, right?

“Would you like to make that a grande?” It’s so ingrained we don’t even notice it. But Starbucks turns a $4 coffee into a $6 order, effortlessly.

Takeaway: Simple language + consistent prompts = powerful results. Don’t be afraid to just ask.


8. Etsy’s “You Might Also Like” Page During Checkout

This one nearly got me last week.

While buying a handmade planner, Etsy slid in a little “You might also like” section — with similar items by the same creator. It didn’t feel intrusive. More like, “Hey, here’s more of the good stuff.”

Takeaway: Use related product carousels, especially if you have a creative brand or catalog.


9. Notion Template Creator’s Premium Add-On

A Notion creator I bought from offered a $10 productivity system. But right after checkout, she offered a $25 upgrade that included goal tracking, habit logs, and extra customization.

Guess what? I bought it.

Takeaway: Offer a deluxe version after the base product — especially with digital goods.


10. Adobe Creative Cloud’s Annual Plan Discount

Adobe gives you two options: pay monthly or commit to an annual plan and save. It’s a subtle upsell baked into the pricing table.

And yeah, most people go for the discounted annual plan — it just looks like the better deal.

Takeaway: Structure pricing so that the upsell feels like the smarter financial decision. You’ll find more smart pricing tips in this post on limited-time upsell offers that convert.


11. ConvertKit’s Subscriber Tier Upsell

As your email list grows, so does your pricing tier on ConvertKit. It’s a usage-based upsell and it works because it’s directly tied to your business growth.

Takeaway: Usage-based or scaling upsells feel fair and keep customers upgrading naturally.


Conclusion

Upsells don’t have to be aggressive or awkward. In fact, when they’re done right, they actually make the customer experience better.

The key is relevance. Timing. And giving people something that makes their original purchase even more valuable.

So, try one of these. Just one. Add a workbook to your course. Suggest a related product at checkout. Offer a premium call. Keep it simple. You don’t need 11 strategies — just one that works for your offer.

And hey, if you try one of these and it works? Shoot me a message. I love hearing those stories.

Tags: Cross-Selling and Upselling Strategies
Ethan

Ethan

Ethan is an email marketing and eCommerce pro who truly gets the ins and outs of the industry. His expertise covers everything from designing compelling email templates that drive conversions to using smart segmentation strategies that target the right audiences.

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