Let me take you back a bit. I was running a little digital shop selling planners and templates.
I’d just made a decent chunk from a weekend flash sale and thought, “Cool, done for the week.” But then one customer emailed me back and said, “Hey, do you have a bundle with this other template too?”
And I sat there, blinking at the screen, thinking… “Wait, I could’ve made more from that order?” That’s when the lightbulb went off: I wasn’t upselling or cross-selling. I was leaving money on the table.
If you’re a small business owner and you’re not using email to upsell and cross-sell, you’re seriously missing out. Not in a sleazy “sell more, sell harder” kind of way but in a “make it easier for your customer to get more of what they actually want” kind of way.
Here’s how I started doing it and how you can too.
1. Start With What They Already Bought
This one’s obvious, but most people don’t do it. Look at what your customer just purchased, and ask yourself: “What’s the next logical step?”
If someone bought a digital planner, maybe they’d love an additional sticker pack. If they signed up for a course, maybe they’d benefit from a workbook or one-on-one session.
I set up an automation in ConvertKit that triggers a follow-up email 24 hours after a purchase. Subject line? Simple: “Want to get the most out of your purchase?” Inside the email, I offer them an add-on, usually at a discount. Works like a charm.
2. Bundle Suggestions in Abandoned Cart Emails
I used to think abandoned cart emails were just to nudge folks back to buy what they left behind. And sure, that’s part of it. But one day, just for fun, I added a “You might also love” section with 2 other products.
Guess what happened? One person came back and bought not one, not two, but three items — including stuff they hadn’t even considered originally.
So now all my abandoned cart sequences include upsells and cross-sells. If you’ve got an email platform like Klaviyo or ActiveCampaign, it’s easy to segment and set this up based on what they viewed or added to their cart.
3. Use Purchase Behavior to Suggest the Next Thing
Your customer data is gold. If someone bought a beginner course, they might be ready for the intermediate one in a few weeks. If they bought a skin care serum, they’ll probably need moisturizer or refills soon.
I now run a monthly email campaign to past buyers, suggesting “next step” products. Sometimes it’s a follow-up, sometimes a complementary product. And I personalize it based on what they’ve already purchased.
You don’t need to overthink the tech. Just tag buyers by product and build a few segmented lists. Even basic automation will make your cross-sells feel tailor-made.
4.Time-Based Upsell Automations
Here’s something I wish I did sooner: time-delayed upsells.
Let’s say a customer buys a digital course. Instead of pitching something new right away, I wait 7 days and then send an email like, “Ready to level up?” Inside, I offer a more advanced product or even a coaching call.
It feels helpful — not pushy — because it comes after they’ve had time to experience the value of the first purchase. It also gives you an excuse to stay top of mind without being annoying.
5. Add Product Recommendations to Your Regular Newsletters
Every now and then, I drop product suggestions into my newsletters. Not full-on promotions — just a “P.S.” at the bottom or a sidebar with “Other tools I think you’ll like.”
Surprisingly, these convert really well. Especially when they’re framed around solving a specific problem. Think: “Struggling to stay consistent? This checklist might help.”
It feels like a recommendation from a friend instead of a sales pitch — which is exactly what you want.
6. Offer Bundles and Limited-Time Add-Ons
I once ran a promo where if someone bought Product A, they could grab Product B at 50% off — but only if they did it within 48 hours. I sent two emails about it: one right after purchase and one as a reminder.
That little add-on campaign pulled in 30% more revenue from the original group of buyers.
Urgency + relevance = magic. Email is the perfect place to combine both without being spammy.
7. Don’t Forget the Psychology
People love feeling like they’re getting a good deal or discovering something just for them.
Phrase your upsells and cross-sells as solutions. Not “Buy this too,” but “Most people who got [this] also loved [that].” Or “Want to get better results? Here’s what helps.”
When you align your emails with your customer’s goals — not just your revenue targets — the sales happen naturally.
Final Thought
Upselling and cross-selling through email isn’t about squeezing every dollar out of your customer. It’s about making the experience better, smoother, and more complete. Think of it like a helpful store associate saying, “Hey, this goes great with that.”
Small businesses don’t need massive funnels to win big. A few thoughtful emails, some smart automation, and genuine customer care? That’s all it takes.
Now go look at your last five sales. What else could those customers benefit from? Start there. The email practically writes itself.
