4 Ways on How to Upsell in Email Marketing

But turns out, it’s a goldmine for upselling. When I finally got the hang of it, my average customer spend almost doubled. Not overnight, but close.

And here’s the kicker: the first few times I tried to upsell in emails? It tanked. Hard. People unsubscribed. One even replied with a “Please stop trying to sell me stuff.” Ouch.

But that’s how you learn. So let me save you the trial and error and walk you through four upselling tactics that actually work in email marketing — all based on real screwups and small wins I’ve had along the way.

1. Use Post-Purchase Emails to Offer Upgrades

The biggest mistake I made? Not emailing customers after they bought something.

I used to send a receipt and go silent. Now? That’s where the magic happens. A simple post-purchase email with a “Thanks for your order — want to upgrade?” message has brought in some of my easiest sales.

What I did:

• Added a one-time upgrade offer 24 hours after the initial purchase.

• Example: Someone buys a basic $19 eBook? I offer the $49 bundle version with videos and templates.

• I use urgency, but gently: “You’ve got 48 hours to grab the full toolkit for 30% off.”

Pro tip: Keep it short. People just bought from you — don’t overwhelm. Just one call-to-action, one offer.

If you’re looking to sharpen this kind of messaging, check out how to write high-converting upsell copy that gets clicks without sounding pushy.

2. Segment Based on What They Bought

This was a game-changer.

At first, I sent the same upsell to everyone. Bad move. Now I split my list based on purchase behavior. If someone bought a design template, they probably don’t care about email writing guides.

What I learned:

• Use email tools like ConvertKit or MailerLite to tag purchases.

• Send product-specific upsell emails like “Loved the template? Here’s 5 more.”

• Personalized upsell emails convert 3x better than generic blasts (seriously, I tested it).

Quick win: Start with your top-selling product. Create one follow-up upsell email based on that. Build from there.

Want ideas for what to promote? Start with this list of 15 best cross-sell products for digital creators — especially if you’ve got a library of digital goods.

3. Add Upsells Inside Automated Sequences

I avoided automation for too long because it felt cold or robotic. But when I finally set up a welcome sequence with upsells, things got a lot smoother (and more profitable).

How it works:

• Email 1: Deliver the freebie or intro offer.

• Email 2: Share your story or how you used the product.

• Email 3: Offer an upsell that expands the value — like a workbook, bonus module, or template pack.

This way, you’re not just selling — you’re building trust first. And by email 3 or 4, they’re warmed up. When I started doing this, my upsell click rate jumped from 2% to 11.5%.

What to upsell:

• Think of what naturally comes next. If they bought a guide, offer the video version. If they joined a challenge, upsell a coaching call.

Need a tech-friendly way to structure that? Check out this guide on how to create automated upsell funnels on Payhip — it’s beginner-friendly and based on trial-and-error experience.

4. Use Scarcity and Bonuses Without Being Pushy

I hate pushy marketing. I’ve unsubscribed from lists that yell “LAST CHANCE!” every other day. So I almost didn’t try using limited-time upsells. But when I framed it as a bonus rather than a threat, it actually felt… kind?

My setup:

• Subject line: “Want a bonus? Only until Friday.”

• Offer: “If you upgrade by Friday, I’ll include 3 bonus templates I don’t sell anywhere else.”

The twist: I never said, “Buy now!” Just, “If you’re ready to level up, this bonus is here for a few days.”

What worked:

• No fake countdowns.

• No pressure.

• Just a helpful nudge with an actual bonus.

It reminded me how much using scarcity to boost upsell conversions can work — when it’s used ethically and in service of the customer.

Conclusion: Start Small, Stay Human

Look, upselling in email marketing does work. But only when it feels like you’re helping, not hustling. Every tactic I shared came from trying, failing, adjusting, and trying again.

Here’s what I’d recommend:

• Start with just one post-purchase upsell email.

• Segment your audience by what they’ve bought.

• Build a simple 3-email sequence with one natural upsell.

• Test one limited-time offer that feels like a gift, not a sales pitch.

You don’t need fancy tools or massive lists. Just pay attention to what your people need next — then offer it kindly.

If you want even more inspiration, don’t miss these 11 case studies of successful upsell strategies — they show just how powerful the right upsell at the right time can be.

And if you mess it up? Hey, you’re in good company. I did too. Keep tweaking. Keep testing. Your email list is more than leads, it’s a customer journey, and upselling is just a helpful step along the way.