Back to Convertkit: Painful Lessons Learned + How-To Checklist

Email marketing for entrepreneurs is one of those things in small business that is super necessary but difficult to do right (at least at first).

Somewhere along the line you realize that you’d like to be able to build a relationship with your audience by more direct means (being allowed in their inbox), rather than hoping your post on Facebook or Instagram will make it through the algorithm and into their feed.

So you sign up for something simple and free (hello bootstrapping!) like Mailchimp and fumble around.

Now, this isn’t a blog on the trials and tribulations of learning email marketing from scratch or even how to get started.

It IS a blog on how there are always lessons to be learned - even when you’re farther down the line in your business.

Here’s what happened when I switched from ConvertKit to Active Campaign, and why I switched back.

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A couple of years ago I decided to invest in my business by switching from Mailchimp to ConvertKit.

I wanted the fancy automations and the ability to really segment and serve my email signups in a way that I couldn’t with Mailchimp.

I rolled along just fine with a mostly-together email marketing strategy that was tied to my consistent blogging and occasional training/promotions.

Then in 2017 all this buzz started around Active Campaign.

I knew several peers that were using it and loved it. What appealed to me the most was that you could set up automation sequences visually (which ConverKit did not offer at the time).

The fact that the setup was visual and it would cost me $20 a month less seemed to make my decision easy.

I spent over a month transferring my subscribers, forms, data, etc to Active Campaign with only one eye on the how-to as I had hired someone to help me.

Within a month of completing the transfer, two things happened.

  1. ConvertKit announced they were rolling out visual automation sequences.

  2. My email open rate tanked.*t.


In the fall of 2017 I made a concerted effort to up my email marketing game and figure out how I could do better.

No matter what I tried (different subject lines, different sending days/times, etc), my open rate just wouldn’t budge.

I had gone from consistently getting between 25-30% opens for my general newsletters with ConvertKit, to barely 15% with Active Campaign. OUCH.

Then one day this past March, I was drafting an email and I noticed that the test email wasn’t coming through to my email address. Although Active Campaign suggests that you don’t send the test email to the same email that the email is coming from, I had never had an issue with it before.

Here’s where it gets crazy.

I reached out to support to find out what was going on. After a few automated and cut/paste answers that I shot down, someone was able to take a closer look at my account.

It took 6 emails back and forth for them to discover and admit that they had been using a “bad” IP address for my account to send emails from.

They assured me they “fixed” it, admitted it was their fault, and informed me they had been using this bad IP for my account THE ENTIRE TIME I HAD BEEN WITH THEM (since the day I opened my account).

After I resumed breathing, I requested a partial refund since they had not been providing a quality service and were 100% at fault. 

This was the response I received:

Hi Cara,

Unfortunately we can't provide refunds per our terms of service:

However, your deliverability should be very good at the moment. If you believe there is still a delivery issue, can you please provide a few specific contacts that have received the message in the spam folder or not at all, and specify the campaign where this occurred?

Once we have this information from you we will be happy to investigate the issue right away.

The refund policy link sent me here:

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So essentially, even though they royally messed up an admitted fault, “buyer beware” and not their problem.

BUH BYE Active Campaign.

And so back to ConvertKit I go!

Now let’s get to the good stuff…

If you are in need of switching your email marketing provider, I would encourage you to think through the steps so you can make the switch as seamless and quick as possible.

I wish I had done this last summer and having a plan this time has made it so much easier!

Want help with your email marketing plan? Yeah - we do that inside Pinterest PowerUp - because once you get that traffic from Pinterest, you need to do something with that traffic. Click below to learn more.


Before deleting any cold subscribers, I planned out and drafted a 6-week reengagement campaign. I sent an email every Sunday for 6 weeks that was stuffed full of pure value.

No selling, offers, or any links other than to more resources.

The aim of this 6-week campaign was to weed out any subscribers that were just totally cold and not likely to ever open another email from me.


While my reengagement campaign was running, I copied and downloaded all of the following into my Google Drive:

  • All email sequences

  • All email templates

  • All subscribers

  • All subscribers by list

  • All subscribers by tag/segment

I then documented in a spreadsheet:

  • All forms

  • All automations

  • All Leadboxes (what I use for forms on my website)

  • All Zaps (from Zapier)


I created a list of cold subscribers that had never opened my emails. Since I had been with Active Campaign less than a year, I was ok with that list being from about 9 months of campaigns.

Here’s the kicker: 

Due to Active Campaign using a bad IP for my account since the day I signed up, approximately ONE THIRD of my list never received an email again from me.

Let that sink in for a second.

One third of my list.

That’s money lost and relationships broken.

Even a partial refund from Active Campaign wouldn’t have made up for that.


As soon as my lists, subscribers, and documentation were ready, I reactivated my ConvertKit account.

The customer support person even gave me 2-weeks free to make the switch and get set up, even though she wasn’t technically supposed to (that’s customer service).

Here’s exactly the order in which I set up my ConvertKit:

  • Created all forms

  • Created all tags and segments

  • Created one sequence at a time

  • Edited one Leadbox at a time

  • Created all automations

  • Uploaded all subscribers by list/tags/segments

Once the forms, tags, and segments were in and situated, I found it easier to create each sequence and connect the sequence to the form, change the Leadbox and create the automation one at a time.


The best part (besides the lessons learned) has been the chance to really fine-tune my systems for naming and building my workflows.

Because my switch last summer was so willy-nilly, I had broken automations, duplicated automations, and a rat’s nest of tags and segments.

Essentially starting over enabled me to really and truly build a strong foundation with my subscribers that will be easy to maintain going forward.

If you want to check out ConvertKit for your email marketing, you can do so right here:

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Hey hey, I'm Cara - Pinterest marketing evangelist and lover of all things Squarespace website design. I team up with online entrepreneurs to get tons of website traffic into sales funnels (marketing speak for getting eyeballs on your website and turning them into customers).

Click the button below to get in touch! 



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