How to Add an Extra $9K per Month to Your Abandon Checkout Automation

It’s starting to feel like summer in Atlanta.

The weather’s heating up, school’s out in two weeks, and my wife and I are scrambling to lock in camps and keep the kids entertained.

Growing up summer was always It my favorite season.

But man… it’s a lot different as a parent.

Every day’s a blur of half-finished tasks. I’ll be cleaning up breakfast, hear suspicious silence, and find my two-year-old emptying a salt shaker onto the pantry floor.

By the end of the day, I’ve started twelve things and finished maybe three.

Kind of like your customers.

They get to checkout, they’re halfway there… then life happens. A notification. A toddler. A meeting.

Gone.

That’s why abandoned checkout flows matter so much. And why today’s issue is all about making yours actually work.

The Pound For Pound #1 Automation

Ah, the good ol’ abandoned checkout automation.

It’s the digital version of someone walking away mid-checkout… and the cashier chasing them down in the parking lot.

If I could only set up one automation for a brand, this would be it.

Abandoned checkout is almost always a top revenue driver. It’s a high-intent, bottom-of-funnel moment.

Someone made it to checkout. They were about to pull the trigger…

…but something stopped them.

I’ve audited nearly 100 email accounts, and most brands run the same default flow:

2–4 emails. Toss in a discount. Add a  “You forgot something” subject line.

Don’t get me wrong, having something is better than nothing.

But a few simple changes can take it from meh to mucho mejor.

I did exactly that for a brand I’m working with, and now a few simple tweaks are bringing in an extra $9,000 a month.

Let’s check it out.

Split Your Abandon Checkout Into Two

Funny how brands obsess over segmentation for campaigns… but when it comes to abandoned checkout, they phone it in.

First-time visitor? Loyal customer? Everyone gets the same emails, same subject line, same offer.

But those two people are at completely different stages of the journey.

A prospect is still on the fence.

They’re unsure. Maybe it’s returns, taste, sizing — whatever.

They need reassurance. An offer, a guarantee, or a quick answer.

A returning customer already decided.

They’ve bought before. They know the product. They just need a nudge.

Here’s a few problems with tossing everyone in the same abandon checkout automation: 

• You give discounts to people who would buy without them and cut into your profit margins.

• You create customer support headaches when codes don’t work for returning customers.

• You miss conversions by sending painfully generic emails to everyone.
  

Prospect vs. Customer: Writing email copy that converts

One instant win from splitting abandoned checkout flows by prospects and customers?

Copywriting gets way easier.

You’re no longer trying to cram two jobs into one email. No more defaulting to “You forgot something” and hoping it lands.

For prospects, your goal is to close the gap between interest and action.

Help them feel confident placing that first order — with reviews, trust signals, a strong guarantee, maybe even a smart offer.

Here’s a structure that works well:

Prospect path

• Email 1: Soft reminder + trust builder
  
  Plain text. Gentle nudge that they left something behind. Include a few short reviews and mention your guarantee to remove early hesitation.
  

• Email 2: Objection handling
  
  Tackle a common hesitation like shipping, price, or returns. Use transparency and remind them there’s no risk with your guarantee.
  

• Email 3: Strategic offer
  
  If your margins allow, introduce a small discount or incentive. Position it as a low-risk way to try something new — backed by the guarantee.
  

• Email 4: Brand story + social proof
  
  Reinforce belief in the brand. Use origin story, product values, or customer love. End with one last nod to the guarantee.
  

If someone’s a returning customer, you don’t need to re-sell them on features and benefits, or handle objections. They’ve already bought in. Instead speak to the outcome they’re chasing, the identity they see in themselves, or the feeling they want more of.

Returning customer path

• Email 1: Friendly reminder
  
  Warm, casual note that their cart is still waiting. Reassure them it’s easy to come back.
  

• Email 2: Support-forward
  
  Offer help. Include a short reminder that your guarantee still stands.
  

• Email 3: Subtle challenge
  
  Light pattern-break like “Do you still want this?” to nudge action. Keep the tone playful but anchored in trust.
  

• Email 4: Light-hearted follow-up
  
  Friendly tone. Gentle reminder of what they’re missing, with one last mention of the risk-free guarantee.
  

Mo’ Emails, Mo’ Money

What I just laid out above is the starting point I use for every abandoned checkout flow.

And that’s exactly what I did here.

After a couple months, the automation was pulling in around $40,000 a month. Not too shabby.

This is where most agencies will tell you with a straight face to start A/B testing anything that moves.

Headlines. Button colors. Timing tweaks. Emojis in subject lines.

But instead of going down the micro-optimization rabbit hole, I noticed something that caught my attention…

The fourth email in both paths was still converting.

1.7% for prospects.

3% for returning customers.

That’s strong. So I thought — why stop there?

Why not crank it up to 11?

We added a fifth email. Then a sixth. Then a seventh.

We’re now running eight emails per path… and some of those late-stage emails are still converting around 1%.

That extension alone added $9,000 in the last 30 days.

Over $100,000 a year from emails that didn’t exist two months ago.

And I know what you’re thinking…

“Four extra emails? What do you even write about?”

Simple. We just kept doing what was already working.

For prospects: we pushed the offer, reinforced the guarantee, and added a little challenge —

“The only way to know if you’ll like it is to try. Risk free.”

For returning customers: more nudges.

Light-touch reminders focused on outcomes — to bring them back to why they bought in the first place.

Well I hope you folks enjoyed yourselves. I’ll catch you later on down the trail.

Got a topic you want me to cook up a recipe for? Drop me an email or a DM.

- Ben

P.S.

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