Mailchimp’s Marketing Automation Recipes Guide for Startups

October 10, 2014 Will Lam


slow cooker recipe mailchimp marketing automation guide
While I’ve previously written about what Mailchimp’s marketing automation means for startups, executing it and making it happen for your startup or small business is entirely different.  I’m currently going through the process of evaluating which workflows work the best for the organization I work for so I’ve had the opportunity to dig deep into what makes sense for us and what doesn’t.

I would imagine you as a reader will have to go through a lot of the guess work and perhaps jumping on a live chat with the lovely Mailchimp support staff (which I’ve done dozens of times over the years).  My guess is that you want to get to the good stuff and don’t have the luxury of time or care for exploring all the nuances of Mailchimp’s automation features the hard way quite yet.

This guide and its recipes assumes that you’re already familiar with Mailchimp and how to navigate it in terms of sending out basic newsletters to your list.  With that said, instead of ruminating and speculating of the possibilities, we’re going to get to the nitty gritty of a few general workflows that would work for your business starting with a proper testing process.

I’ll also be creating video walkthroughs, narrated by yours truly that are exclusive to subscribers of Bootstrapper’s Weekly Digest (a weekly digest of blog posts and resources that relate to bootstrapping that personally handpick and curate), but I’ll only produce them once I hit 200 subscribers so be sure to sign up. You can help out by sharing this post on Twitter or sharing on Facebook :)


Testing Recipe:

Before deploying any automation workflows that will allow you to deliver value to your subscribers automatically without lifting a finger after you set it up, you’ll need to test all of it out first. Here’s what you need.

Ingredients: Test Content, a “staging list” of emails that you can test without any consequence, older or test campaigns that you can send to your staging list. Depending on how nice it is, and the complexity, you might need a designer as well as someone proficient in crafting the HTML and CSS for emails. If you don’t, you might want to hop over to Treehouse and check out their course on crafting emails, taught by one of Mailchimp’s very own designers.

Preparation time.  Depending on a variety of factors such as how quick your organization is, how many level of approvals you’ll need to go through and the number of stakeholders, you’re looking at anywhere between a few weeks to about a month or so in order to test everything thoroughly, so as long as you have a content strategy and content ready for deployment.  If you’re just running a quick and dirty experiment as a proof of concept you can execute an experiment within a week or sooner than that to use as a proof of concept.

Keeping in mind that you don’t have time to wait 4 weeks or however long you want your lifecycle email marketing campaign to be.  Assuming that you have everything in place, the test can be completed within a few hours as the shortest period of time Mailchimp allows between emails is 1 hour (as of writing this). Mailchimp does have a test mode to be able to send you   However, if you like you can set your automated campaign to send out immediately when a person subscribes to a list.


Before even considering setting up a workflow in the Automation tab, and I’m surprised Mailchimp hasn’t suggested this anyway – I would highly suggest you create a sandbox for you to “play” in before experimenting with any of your (or your company or client’s for that matter) live lists.  You want to avoid the worst case scenario of sending out a bunch of irrelevant test automation emails to a live list.  If you go ahead and attempt a workflow on your live list, you’re risking unsubscribes and cancellations all due to an ill executed marketing automation campaign to your entire list or user base.

Creating a list with emails that are directly in your control, others on your team.  I’d say a sample of around 10-30 emails that you can essentially jump into or verify with your team who’s willing to tolerate many of your automation campaigns.  You don’t have to have unique emails as part of your list, you could simply add a “+1” to an email in your direct control to create a variation. For instance if your email is, you can extra emails in this fashion: “”, “” etc.

staging list mailchimp automation
Create a staging list where you open emails with some, click through, and not so much with others. You want to simulate a live list.
Mailchimp Automation tutorial 2 Mailchimp automation tutorial staging list mailchimp automation configuring trigger tutorial Mailchimp automation tutorial 3 Mailchimp automation confirmation tutorial Mailchimp automation tutorial 4

After that, I’d replicate previous campaigns (if you have them) and start sending them out to that staging list that you created and open up those sent campaigns in certain emails and not in others to simulate a live list where you have highly engaged customers and those who aren’t.

This is especially useful if you’re going to be mimicking a re-engagement campaign.  For customers who have recently become inactive and haven’t opened up an email or engaged with any of your campaigns for a while will be those who should in theory (and have less Mailchimp stars according to their rating system) get the re-engagement emails to hopefully become re-activated and using your product or engaging with your campaigns again.

Since you’re already testing this, I’d play around with the conditions to see how many recipients meet the requirements of a trigger and look into crafting an automated workflow if it makes sense for that segment.


Once you get the sequence down and the emails are hitting your inbox, check to see which emails hit the inboxes so you gain a level of confidence in your automation workflow.  Once you’re comfortable with the results, consider the timing of your emails and looking into segmentation.




milkman delivery service email automation

Proper segmentation is part of the foundation of having a successful automation strategy in place, so that the right users are getting the right emails at the right time.  Think about that for a moment.  It takes a bit of getting used to in terms of wrapping your head around it but it’s worthwhile to understand and very powerful once you do.

At any given moment, your list has subscribers that have joined at different points in time.  To give you an example of not segmenting leads to a poor user experience, if you were sending the same campaign for users who have already purchased something from you that’s targeted towards first time buyers, it would make absolutely no sense.  But if you were to properly segment your automated campaign so that only those who have not made a purchase get the campaign, then you’d have something that would resonate with subscribers of your list at any given time – without lifting a finger.  How cool is that?

segment profile activity

Proper segmentation can help you understand and separate your most engaged members of your list between those who aren’t as engaged with different campaigns for those two segments among many others, such as signup source and so on .  Doing so will inform your email and automation strategy to keep your members regularly engaged with your email marketing efforts.

To get a sense of what kind of segmentation you can do, Mailchimp has their complete list on segmentation here.



Welcome / Onboarding workflow recipe

welcome onboarding email california

Ingredients: strategy, onboarding content, setting up Mailchimp Goals javascript code into header is optional for a more advanced setup.  Understanding all the necessary steps of your product to deliver value and get your subscriber to the “A Ha” moment as soon as possible.  The number of onboarding emails may vary from product to product.

Preparation time: two weeks for strategy, map out the sign up flows, content first draft, and a few days for testing.  It would be a good idea sign up for services that you admire and dissect their welcome series of emails and see what you can learn from them or perhaps copy (where it makes sense).

If you’re starting from scratch, a quick way you can hit the ground running is to search your email history of a product you first used (let’s say Dropbox or a tool that’s similar in your space) right from the beginning and get some inspiration from the series of onboarding / welcome emails from services you already use (unless you’ve already deleted those emails.  I’d also  highly recommend checking out  Copy, test and iterate until you have an onboarding workflow that works for your company.


Your welcome / onboarding workflow can be as simple as one email, but the power in spreading out the onboarding sequence over time so your users get to the “ah ha” moment sooner.  This is especially important if your product requires a bit more cognitive effort from the user.  It will be exponentially harder when you throw downloading software or installing hardware in the mix.  By properly onboarding your users, you’re doing them a service by delivering succinct instructions and teaching the user how use your service.  You’re doing yourself a service as you do want not overwhelm your new users and who wants to answer more support tickets when it comes to setup?

At the end of the onboarding flow, all of these emails should result in a favourable first impression of your product so they’ll come back and hopefully make it a habit to use your product.  Depending on the complexity of your product, and the tooltips (if you have a web or mobile app) that are spread throughout your initial product experience.


While you probably won’t get your initial onboarding sequence right – it’s always a good to have something to help your newly acquired subscribers truly discover what your product is all about.  If you’re adept at cohort analysis or conversion optimization, you’ll be able to unearth reasons why users aren’t coming back or why they’re sticking around if you’re constantly in communication with your users (which is always a good practice). Doing in person user testing or signing up for a service should be able to help you understand the ideal onboarding process and whether or not the user acclimates themselves with the user experience that you had in mind.



Drip Campaigns / e-courses

drip email course

Purpose: generate and nurture leads to hopefully convert them to a paid service because of the value you’ve delivered that’s tied into your paid product during  by the end of an e-course with a call to action and a compelling offer at the end of your course or drip campaign.  Can be used to re-engage inactive users.

Ingredients: Research about what you’ll be teaching and how it ties back to your core value proposition.  Are there recurring themes in terms of questions asked time and time again by customers, subscribers or users?  When you answer that, ask yourself why would it make sense to create these series of emails and why your subscribers want to receive them in the first place?  It could be for a sales nurturing track, lead up to a event that you’re hosting, driving sign-ups for a webinar.  Once you’ve determined what the purpose of the drip campaign, you’ll have to start planning out how many emails will be part of that campaign, the time span you have to work with before

Preparation time: there’s no clear cut answer here as the answer varies across different industries and verticals.  Whether you decide to produce your email course in house or outsource it, the amount of time required depends on the complexity of the topic you’re trying to teach and how it leads back to whether or not how closely aligned the topic is with the product you’re solving and the pain it solves.  Again, you’ve probably experienced a drip campaign at one point or another, and your inbox would be the first place to see what drip campaigns have been most effective for you.


If you’re launching a new product, usually there’s a sequence of emails leading up to a launch, so look into how long you want to space out the course (usually a month is a good yard stick to start with).  While there isn’t an optimal number of emails, spacing them out a few days between each other so your subscribers can digest and take action on your email course.

Study and dissect Noah Kagan’s free Summer of Marketing and Double Your Email List email courses  or Peep Laja of ConversionXL’s Free Conversion Optimization course to get an idea of what how it’s properly done.


Be sure to check your open rates over time to see whether or not users are actually engaging with the e-course. Here you’ll want to see if subscribers to your drip campaign or email course actually converts or moves subscribers down the funnel in your analytics outside of Mailchimp like Google analytics with special landing pages or UTM parameters.  If your goal is to convert users to a paid option, you should see whether or not there’s a downstream effect on conversions of email subscribers.



Re-engagement / Win back campaign:

miss you email marketing mailchimp automation

Purpose: To bring back previously active subscribers, customers or users that have lapsed or are simply not opening your emails at all. Famous examples of re-engagement strategies are Facebook’s use of guilt

Ingredients: Understanding of why your customers have lapsed. Tools that help you understand are a cohort analysis tool that’s built in-house or something off the shelf from Mixpanel, Kissmetrics, RJMetrics or if you have a mobile app, Taplytics to understand the activity or purchasing behaviour of your subscribers.

Preparation time:

If you have a smaller team, and have the authority to bake re-engagement into the lifecycle of a user, it should take a few weeks if you have a good grasp of the concept of re-engaging old subscribers or users.


If you don’t quite understand cohort analysis yet, it’s a very powerful visual tool to understand how certain groups of users are behaving or as Wikipedia succinctly puts  “Cohort analysis allows a company to “see patterns clearly across the lifecycle of a customer (or user), rather than slicing across all customers blindly without accounting for the natural cycle that a customer undergoes.” has a great primer or cohort analysis over on their blog if you want to dig into it further.  I’ve also curated a list of cohort analysis resources on Kippt for your convenience as well.

While I would argue it is worth the time to understanding cohort analysis as it allows you to understand your subscribers even more intimately, you might not have the time or the desire to use something as sophisticated as cohort analysis.  However, through segmenting your list by focusing on those who are “3 stars” and below according to Mailchimp’s engagement metrics, it should help you re-engage some users.

In the Trigger step of setting up an automation workflow, after selecting the list, it would look like the screenshot below.

mailchimp re-engagement segmentation


By setting up an automated email that will bring back subscribers, you can still increase the bottom line, instead of having a list that doesn’t convert at a higher percentage. Here’s a great example of something that re-engaged and eventually converted me.

Blinkist re-engagement email
Yup. Hook. Line and Sinker. I converted after I got this email.


Depending on what tools you’re using to measure re-engagement, you should see an uptick in previous cohorts of users if it’s a success.  I’d give the re-engagement workflow a month to review before you tweak anything.  Also, checking out Google Analytics or whatever measurement tool you’re using for conversions is something you should look into.  The end result should be some lift or impact on revenues.  If you’re not getting any lift in conversions down the line, then you’re doing something wrong.  (Email me over at will(at)willlam(dot) if you want to talk!).   Remember, if you’re not using a re-engagement strategy, whether you’re a SaaS app or have a digital product to sell, then you’re simply leaving money on the table.

Advocacy/Evangelist Campaign

word of mouth marketing

Purpose: On the opposite end of the spectrum of lapsed subscribers, are those subscribers that really engaged and absolutely love you.  They’ve written to you,  blogged about you, tweeted at you, wrote about you on Quora, go to your events and maybe even bring you more customers through word of mouth – all without you prompting them.  They are advocates of what you or your company does and shout out about you on their rooftops whenever they have the chance because they really love what they do. But what if you had a process to empower those who want to evangelize on your behalf

You can have them like your Facebook pages, follow you on Twitter, answer questions on your behalf on Quora if they’ve demonstrated a high level of engagement with your campaigns.  You can easily flag these advocates with the VIP function manually.  With these users, they can help you generate more leads, create buzz and discussion amongst your friends.  If you’re in the B2B space, advocates can help you speed up sales cycles as well if they’re willing to get onto reference calls to vouch and evangelize you.  You’ll want to treat these advocates with utmost care and respect.

Ingredients: social media channels, such as Twitter, Facebook, Quora. Events to validate and say “thanks” in real life to your VIPs.  to help amplify the reach of your content. If you’re a bit further along and there’s a sales process, they can benefit from this workflow as well, especially if those customers can get on reference calls – which is particularly helpful in closing and speeding up the sales process in the B2B world

Preparation time: At the very minimum you’ll be looking at a month to start using this particular recipe, but it’s better to assign a longer time horizon to be able to surface and identify your advocates and evangelists. This should be an ongoing process, but a high touch one so that they’re not talking to an automated sequence of emails all the time.  By then, you should have a team set up for customer success / relations.

Manage Subscribers Create a VIP segment Choose a Custom Mailchimp Workflow Configure your workflow create a vip segment for mailchimp Set Your Up Advocacy Email Sequence for Mailchimp

Instructions: Over time, those who are closest to your users are the ones who can designate certain users as VIPs, such as a customer success team, product managers, marketing managers to even the Founder/CEO themselves if they’re really early stage.  Another way of designating those who are VIPs without actually tagging them might be to segment those who are “5 stars”.  It also might be a good idea to have tokens of appreciation that you can freely give away to your users that are exclusive to them.  It might be t-shirts, or upgrades to the product or even calls from the founders/CEO themselves soliciting product feedback from their most valued customers.

This might not be the best workflow to start off with until you’ve reached product / market fit, but when you do, this should help accelerate the business by helping amplify your marketing efforts and closing sales.


Like other workflows, there should be some impact in terms of the word of mouth generated that is directly attributed to your VIPs.  If there’s a higher touch sales process at your company, it should help accelerate growth to your bottom line as well.



Caveats & Limitations

One of the big things that separates Mailchimp from marketing automation vendors or other automation first companies is while they execute the email part of automation very well as it’s their bread and butter (they didn’t put the “mail” in Mailchimp for no reason..) – what they sorely lack are things that are entirely outside the scope of what their capabilities are.

It’s a bit disingenuous on Mailchimp’s part to call their product “Marketing Automation” when in fact, it isn’t.  Automation it can do, but full Marketing Automation comparable to other vendors it isn’t.

Some examples would be landing page creation,  lead scoring, and CRM integration to name a few.  There’s also the lack of granularity in creating smarter segments with a “if this, then that” precision, along with the ability to assign a unique cookie to each user to attribute all events a subscriber has taken from the top to the end of the funnel.  Then  there’s  the presence of their “suppression lists”.  Suppression lists are a good thing and can protect your sender reputation, mitigate spam complaints, and to generally not send irrelevant email to subscribers.  In Mailchimp’s case, they are akin to unsubscribing the email altogether, which isn’t ideal especially if there’s a fair chance to re-engage or convert a subscriber that’s gone cold.

For a workaround in terms of suppression lists for subscribers who have already converted you can try this Mailchimp workaround:

@jlinowski Groups might be the best way to do what you’re describing.

— MailChimp (@MailChimp) September 22, 2014

For startups and small businesses that aren’t quite ready to sink in the tens of thousands of dollars for enterprise grade Marketing Automation, Mailchimp is a great solution that every marketer and business owner should push the limits of Mailchimp until they face the strain of needing full fledged solutions.  For all that the Automation features Mailchimp has going for them, there’s still a long ways to go for it to be a full blown marketing automation vendor comparable to the Hubspot, Marketo, Eloqua and other big players.  However, Mailchimp has some good uses cases to get startups and small businesses to hit the ground running with some high ROI results before moving onto more granular marketing automation workflows.  I am excited and expect to see Mailchimp to be filling more gaps as time goes on.

I’ll also be creating video walkthroughs, narrated by yours truly that are exclusive to subscribers of Bootstrapper’s Weekly Digest (a weekly digest of blog posts and resources that relate to bootstrapping that personally handpick and curate), but I’ll only produce them once I hit 200 subscribers so be sure to sign up. You can help out by sharing this post on Twitter or sharing on Facebook :)

Are there other workflows that you think I should include? Leave a comment and let me know!

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