The three most powerful Mailchimp automations

Email automation doesn’t have to be scary.

It can actually become the most important part of your business, since it helps you connect with new leads, turn them into customers, then into fans—no nerdiness, coding or tech skills required. It can even happen while you’re sleeping (or eating vegan burritos). No matter what type of business you run, from an online course website to a vegan burrito delivery service, email automations are a powerful way to connect with folks interested in what you’re doing.

(Note: Even if you don’t use Mailchimp, you can set the following email automations up in any newsletter service.)

In fact, you probably already use it without realizing, since you’ve got a welcome message when someone signs up for your list (Mailchimp automatically sends one, unless you turn it off or use a customized welcome automation instead).

Unlike campaigns in Mailchimp, which are one-offs, automations happen every time specific people meet specific criteria, like buying a product or signing up for a demo. And once an automation is running, you can segment people out. For example, if you’re pitching your product and someone buys on the 2nd email, you don’t want them to get the 3rd pitch. By tracking who buys what from you, you can take your automations to a whole ‘nother level. You can learn how to do this in Chimp Essentials.

This is the whole point of mail automation–sending the right emails to the right people at the right time. It’s as simple as that. So let’s look at three of the most helpful automations, beyond the welcome email and basic Mailchimp setup.

Turning leads into customers with Mailchimp

You know how sometimes you go to Costco and there’s stations set up with delicious free samples (sometimes even vegan burrito samples, although the frozen ones aren’t ever as good as the ones made fresh)? That’s because people want to try (or taste!) before they buy.

The same is true with digital products, like ebooks, online courses and  software. Which is why automation sequences, like onboarding, that help give people a taste of what you’re offering can be so helpful—and by helpful, I mean profitable.

My highest converting automations sequences are the ones that do a few things really well:

  1. They educate. If I’m selling an online course on the business of freelancing, I’m going to offer an email automation sequence that teaches people some valuable lessons about the business of freelancing first. I’m going to let folks sign up for this free series on the homepage of course, and I’m going to drip out daily lessons to them to really give them as much education as possible. The best lessons won’t be held back or hidden behind a paywall either. I’m going to lead with solid gold. Showing these subscribers how useful the course can be helps build trust.

  2. They self-select. For myself and many other people who sell things online, I’d rather make sure someone is a great fit for my product first, before money is involved, then take their money only to give them a refund later. Automations triggered before any purchase is made allows people to get a taste of my teaching style, my language and exactly what they’re going to get with my offering. That way, if they come to realize what I’m offering isn’t for them, they can unsubscribe and not have to ask for a refund.

  3. They share and build relationships. The best way I’ve found to sell is to tell other people’s stories. All the automation sequences dispatched (get it?!) before I ask for a sale involve sharing how other customers have used what I sell to do better or profit more. I share case studies, success stories, videos of people who’ve been customers for ages and short testimonials. Such tangible data helps build even more trust, because it’s not just you saying how awesome your product is. It’s other people saying it

  4. Then, they ask for the sale. Once I’ve educated subscribers, shown them exactly what they’ll get and shared other people’s stories about what I’m selling, I can ask them if they want to buy. Here’s where things get fun: I only want to ask if they didn’t buy yet. Sometimes folks sign up for a free sample which has 10 days of automations but they buy on day 2. Or day 9. I don’t want to pitch to people who’ve bought already because it makes me look silly. Imagine you buy a freelancing course, then a few days later get an email telling you how amazing the course is and that you should buy it today! Preposterous. Mailchimp lets you be smarter than that. Coupled with what you learn in Chimp Essentials, you can automatically segment out people who’ve already purchased your product from your automations. That way they can still get the educational emails (if they want), but won’t see pitches for any products they already own.

Within each email in a Mailchimp automation sequence, you have the ability to create segment conditions. If you’re using Fixtail (or something like Shopify or WooCommerce) to send purchase information about subscribers to Mailchimp, then you can segment people out if they’ve purchased a specific product. This is how the right email is sent (or not!) to the right person at the right time.

Turning customers into fans with Mailchimp

Too often businesses don’t pay enough attention to their most important people—their customers. They work so hard at making the sale but then put almost no time into what happens after the sale.

Which is too bad, since that’s the best time to connect with your new customers, right after they buy. Once you add purchase and order information to subscriber details, so you can set up automation sequences that trigger the second they become customers.

Here are a few things post-sale automations can do to really benefit your business:

  1. They say thanks. Call me a polite Canadian, but I like to say thank you when someone does something for me, whether it’s holding the elevator or buying something I sell. I like to let folks know that, even though it’s an automation that’s being sent, I noticed their purchase and was appreciative of it. You can even get fancy, by creating personal video thank you messages in a pretty neat app called Bonjoro. The first email in a post-purchase automation can simply thank a person for buying and maybe ask if they have any initial feedback.

  2. They give a reminder about access details and important URLs. Typically, if you’re selling something digital, after a purchase people are taken right to the thing they just bought: a course, an ebook, a piece of software. But, after they use it a bit, they get distracted (probably by cat videos), they might forget how to log in, where their downloads are, or other important information. The second automated email I send in a post-purchase sequence is a reminder email that gives all the details they need to keep handy.

  3. They show customers how to get the most out of what they bought. Just because someone bought from you doesn’t mean the education should end. Indeed, if you want your customers to become fans of what you do, the education can’t stop. Sometimes people don’t know how to properly use what they’ve purchased—like software—or don’t know how to get the most out of it—like a course. By teaching them all the ins and outs of what they bought, they’ll be more likely to use it. And if they’re using it, they’ll like it more and tell others. For bigger items, I tend to drip education out in 4-8 emails, with each email covering one important topic.

  4. They help ensure customers are using what they bought. A post-purchase sequence can help your customers actually use what they bought from you. Are they watching the lessons in your course? Have they started using your software? Reading your ebook? If they aren’t, you can ask why or offer to help. If they are, and they’re digging it, you can give them a way to review their purchase (on Amazon, on the App Store, wherever).

  5. They take their pulse. After I’ve thanked, reminded, educated and made sure someone is using what they bought, I like to ask them how likely they’d be to recommend the purchase to others. This is done with a simple survey or poll in Mailchimp. Basically, “would you recommend this to others?” If they respond yes then I trigger a follow-up email that gives them a way to share it and join an affiliate program, if there is one. If they say they wouldn’t recommend it, I reach out to find out why. Either way, the feedback is invaluable.

By engaging with customers after the sale, you can take them from simply buyers of what you’re selling to fans of you and your company. Fans are much better than customers too. Fans are a part of your sales team. They’ll tell everyone they know about what you’re doing and selling. So treat them well.

Turning fans into repeat offenders with Mailchimp

Whoa, kudos for making it to the final step! You’ve turned subscribers into customers, and customers into fans. Now you’re ready for the final step: turning those fans into repeat offenders. And I’m not talking about stealing vegan burritos for a living (burrito bandits, if you will). I’m talking about doing what it takes to make folks want to buy from you… again.

If you know exactly what someone bought and when, you can do some powerful stuff with Mailchimp automations. You can turn a $20 one-time purchaser into a long-term fan who spends thousands of dollars on your products/services over the course of years (or even decades). Let’s look at some of the most useful automations to get your fans to come back for more:

  1. They offer replenishment. This doesn’t just apply if you’re selling subscription-based foods, like Soylent. Replenishment emails also work if you sell software that uses credits or you sell subscription based digital products that are close to the renewal date. I’ve seen them work really well for charity organizations that offer virtual animal adoptions (I may virtually adopt a lot of animals…) to let folks know what another yearly donation can mean for their adopted friend. By reminding folks what they’ll lose out on if they don’t renew or replenish, you give your business the best chance to keep them as customers for longer. You can even offer deals or discounts for returning customers to make them even more eager to buy more.

  2. They pitch additional products. What I’ve noticed with my own customers is that getting them to buy the first time is the hardest part. It takes the longest, it requires more work on my end (which is totally fine, I like working) and it’s the most trepidatious a person will be, since they don’t know your business that well yet. On the other hand, once someone becomes a customer of mine, they’re more likely to buy more of my stuff. And not just a bit more likely either, a whole lot more likely. Most of my customers have bought more than one thing from me. That’s why having an automation sequence that triggers if someone buys one thing, but hasn’t bought another is super useful.

  3. They reward your biggest fans. Since I sell several things: courses, software, and the occasional random product, I like to know which subscribers are the biggest financial supporters of what I create. That’s why I like to reward the people who’ve spent the most money with my business and do something special for them. I like to ask for their mailing address if they spend more than a certain threshold, so I can send them something fun in the mail. This gesture helps create a better connection with the people who are the most supportive. And hopefully, it helps keep them stoked to buy from me in the future.

To sum it up

Hopefully now you can see that email automation isn’t so scary. In fact, it’s super useful to any business that sells online.

  1. Make sure your leads get to know you before you try and sell them stuff. Educate them, show them why what you’re selling is valuable, show them there’s more than just you talking about your products.

  2. Make sure your customers know how to, then use what they’ve just bought. Teach them the ins and outs or little tricks. Show them what they bought is valuable and how they apply that value to their own lives or businesses.

  3. Make sure you keep them coming back for more. Give them a reason to. And then treat them like super stars when they do.

This is why I teach Chimp Essentials—so you can learn how to setup automations like the ones I listed above. Because when you know how to do things like that that, you can get pretty smart with how you set up and segment your automations.

The best part is you can set these automations up and almost-forget about them. You do need to check in on them from time to time to make sure they’re converting well, helping a lot and being read. But that said, they’ll still work for your business whether or not you’re sleeping or eating those delicious vegan burritos!

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A/B testing, multivariate testing, split testing, the same thing. The idea is simple, you test one thing (or many things) against one another to see which performs best. Some people get scared of this, cos it appears quite technical on the surface, but typically...

How to write awesome email subject lines

Subject lines, along with timing and relevancy, is the single biggest influencer to help you boost your open rates, BUT there’s SO much info out there on what constitutes a great subject line, and a lot of this advice conflicts. In our many years of hands-on...

How to build your Mailchimp audience

So, one of the main things people want to know is – how do I get more subscribers. Some people resort to buying, worse still scraping, data. I get it, it can be hard. There’s so much noise out there online, trying to put your hand up and be like ‘hey, subscribe’ can...

Intuit buys Mailchimp for $12bn — but what does that mean for customers?

So, Mailchimp is to be acquired by Intuit. It’s now official. BUT, what does that mean for you? Here, I predict where Intuit will take Mailchimp, and what impact that will have on you, the customer. Less free stuff Taking a quick look at Intuit’s primary offering...

Mailchimp Stores: a giant leap forward into commerce

Ben Chestnut (Mailchimp CEO) recently announced Mailchimp Stores, their first proper foray into the world of commerce. Let's take a dive into how this all works. First up, click on the Website icon on the left to go to your website settings. Here's where you'll find...

Introducing Click Maps from Mailchimp

Hey chimp fans, Mailchimp is rolling out cool feature after cool feature. So we're gonna tell you all about them and where you can find them. First up, Click Maps. Click maps are a great way to visually see which links are being clicked the most. So, let's take a...

Mailchimp’s New Email Builder: What’s Changed and How to Switch

When Mailchimp first introduced its new email builder, it sat alongside the classic editor as something you had to switch on manually from your account settings. That was the experience back when we first wrote about this. A lot has changed since then: the new builder...

How Mailchimp makes $700m revenue — A Chimp Essentials growth story

Hey all, so we thought we would give you a study guide on some of the big brands out there, and we decided the best place to start is with the company we all know and love here - Mailchimp. Now before we dive into things, Mailchimp sends out more than 600 million...

Email Marketing Strategy: Why Email Newsletters Still Work in 2026

This guide explains what actually works in modern email marketing in 2026, and how to design, write, and send emails people want to open, read, and click. Let’s start with something blunt. Email newsletters are dead. Not email marketing. Not automation. Not lifecycle...

“The lessons are easy to apply”

Here’s a note from a recent student, Simon Lamey: “If you are hesitating about taking this course, I wouldn’t. What you get for the money you spend is of great value.”

Why almost no one is actually leaving Mailchimp (2019 updates explained)

Mailchimp is still the email marketing platform I use and believe in to run my online business which includes selling courses, software products, books and speaking directly to my audience through a weekly newsletter.

A conversation with QuHarrison Terry about building a brand through his newsletter and the amazing story of getting hired by Mark Cuban after putting his resume on a billboard above a Banksy

A video interview talking about newsletters and QuHarrisons amazing story that lead him to being hired by Mark Cuban (owner of the Dallas Mavericks, entrepreneur and Shark Tank investor).

Truth time: are Mailchimp alternatives really better?

Let’s get real with each other right now, there are a lot of newsletter software companies out there, beyond Mailchimp. There are probably a hundred Mailchimp alternatives available. But Mailchimp will always be my first choice. Learn why in my Mailchimp review and why I choose it over other email marketing software.

Mailchimp vs Constant Contact, which is better?

Should you use Mailchimp or Constant Contact for your email marketing? Learn more about the differences between Mailchimp and Constant Contact to help you choose the right email marketing software for your business.

(Unfortunately) the best Mailchimp templates are simple and boring

The debate has raged on for years—which is better for email templates, well designed HTML or plain-text? If you’re searching for the best Mailchimp templates for your email marketing, knowing what templates perform best is important in your search. In the world of...

Mailchimp surveys are your most powerful tool for personalizing your email marketing

Mailchimp surveys are a powerful tool for personalizing your email marketing. Learn why & how to use Mailchimp surveys & polls, integrate third-party services like Google Forms, SurveyMonkey & Typeform into newsletters.

What is Mailchimp (and why should you care)?

Mailchimp is email marketing and marketing automation software that lets you stay in touch with groups of people via email. Mailchimp is even free to use for smaller email lists! Learn why you should use Mailchimp for your business and how I’ve used Mailchimp to grow my own.

Which is better, AWeber or Mailchimp?

Looking at AWeber vs Mailhcimp for your email marketing software? Find out why Mailchimp is better than AWeber for your business’ email marketing.

Does Mailchimp have drip campaigns?

Can you deliver content upgrades with Mailchimp? Absolutely. Learn how to create content upgrades on your website to grow your list and deliver opt-in freebies to your subscribers with a Mailchimp drip campaign without being charged twice for subscribers.

Every business should have a mailing list

The benefits of using email marketing in a business are invaluable. Learn why email marketing is my top recommended marketing strategy for businesses of any size and why email marketing for small businesses is more important than social media.

Automating potential leads

Automating your client onboarding process with email makes it easier and quicker to turn leads into customers. What is onboarding? Learn more about the benefits of onboarding clients and how to start using an onboarding process with your business.

Dear FNAME, newsletter personalization isn’t what you think it is

Personalized email is so much more than using the FNAME Mailchimp merge tag. It’s about segmenting your list to send the right emails to the right people at the right time. Learn more about personalized email marketing and how you can use it in your business.

Email automation and your business

On its surface “automation” brings forth images of robotic arms in widget factories or lifeless emails (selling those robotic arm fabricated widgets) blasting out mindlessly for eternity. Using automation email for business, however, can make a big difference in how...

Want to improve your newsletter deliverability?

Improve your Mailchimp newsletter deliverability by using Mailchimp’s SPF and DKIM settings to verify your domain. This loads images by default in Gmail and allows you to use your custom domain. Follow this video tutorial to set it up in under 15 minutes.

Mailchimp automation is great!

The possibilities for email automation and automating your business are endless. And if you do it correctly, your audience or even your customers will be happy to be taken care of with your personal, albeit automated touch.

This is the exact opposite of every “grow your list” article

There are SO MANY articles about growing your email list, and really, they just spew the same tired crap about “more subscribers = more profit” and using “All The Popups”. Real list building centers on knowing your purpose and giving value. Learn how to build an email list that actually works.

Why my favourite mailing list isn’t even a mailing list

You might think my great email design inspiration come from studying emails of big corporations with slick designs and professional marketers. No, it’s from my local farm. I love this email newsletter so freaking much it’s lead me to create other great emails.

Which is better, ConvertKit or Mailchimp?

Here’s the honest look at comparing the two email software programs, ConvertKit vs Mailchimp. Many of the gripes about Mailchimp aren’t actually true, like double charging for subscribers. Learn why Mailchimp is just as good (and even better) than ConvertKit and why I’m sticking with Mailchimp.

How to make money from your Mailchimp mailing list

Year over year, more and more of my income is a direct result of my newsletter. For each $1 I spend on my email list, I make $120 in revenue. Learn how to make money with an email list from my experience running my successful email list and helping others do the same.

Email Marketing agency Mailchimp Experts
Mailchimp Pro Partner
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