The Ultimate Guide to ConvertKit for Service Businesses

I’m excited that you’re here. I put this ConvertKit guide together to help me organize my decade-plus experience and knowledge of email marketing and I hope it helps you.

Along the way, I’ve made just about every mistake you can make with email marketing. My goal is that through this guide, you’ll be able to “stand on my shoulders” and bypass some of those missteps.

In the process, you’ll see results more quickly.

Is this guide only for ConvertKit Users?

This guide is written with ConvertKit in mind, however, the principles we’ll cover together are really email marketing principles and can be applied to most any email marketing system. And I should know, I’ve used most all of the major email marketing systems.

In fact, here’s a short list of the tools I’ve used over the years…

  • Infusionsoft (I was an early user and stayed with them for almost eight years).
  • ActiveCampaign
  • Aweber
  • Drip
  • MailChimp
  • Hubspot
  • ConvertKit (which currently runs our mailing list).

And for clients, my team and I have used (in addition to those listed above):

  • Zoho Campaigns
  • Agile CRM
  • ConstantContact

The point is, we tried and tested and used every major player in email marketing over the last decade. What you do with the tool is often more important than the tool.

That said, ConvertKit gives us the right balance of simplicity and power, and it might be right for you. If you’re looking for your first email marketing tool, or just looking for something that suits you better, you can get a free trial of ConvertKit here. (Full transparency: Links to ConvertKit, Demio, and Bonjoro in this post are affiliate links. We believe in and use all three tools.)

Now, lets get going…

Setup ConvertKit

Business man riding a rocket - ready to start email marketing.
There are plenty of guides that will teach you the technical ins and outs of setting up ConvertKit. But do they guide on the two key decisions that will help your business? Let’s look at what those decisions are, now.

There are two things you want to do to get yourself setup for success with email marketing.

First: Choose your template.

I’ve seen entrepreneurs agonize over something as simple as choosing a template for their email newsletter. Sounds crazy doesn’t it. But for many, they see it as a big decision. One that dictates how their brand will show up to their clients and potential clients.

And they are right.

However, when you frame the decision in this way, it leads you to a bad decision. See, the natural tendency when you think “this is a representation of my brand” is to immediately believe that your brand is visual.

Then, you start adding logos, and fancy fonts, and pictures, and colors.

The problem is that your brand isn’t primarily visual. You brand is a promise you make to the people you want to do business with. It’s a feeling you create in them. In smaller businesses, your brand is more often the “personal” relationship (a feeling) that exists between you and your prospects and clients.

Key word…personal.

We’ve found over the years that we get the best results for ourselves and our clients by using an email template that is shockingly simple.

One that looks very much like an email they would get from a friend. Your friend doesn’t usually put a big logo at the top of his emails. She doesn’t use much color—probably just black text.

And certainly no fancy fonts.

Your email template needs to be the same.

Thankfully, ConvertKit’s default template works perfectly for this kind of simple email.

Don’t overthink this whole template thing. Just keep it simple.

Next: Create your “super signature.”

This is an idea I picked up from Dean Jackson, and it’s been a huge help in directing people to the right offer for them.

The idea of the super signature is simple.

In all of your newsletter-style emails you put three or four offers at the bottom of each email.

The easiest way to do it is to make a copy of the default template in ConvertKit (On your settings page, the email templates link is in the upper right), and add a little bit of code at the bottom of the email content.

Example email super-signature HTML code, Dean Jackson style.
Insert the super-signature between the “message-content” section and the “footer” section in the email template.

Here’s what it looks like in an email…

One of the biggest frustrations with people who use an email newsletter is that they send out stuff every few weeks, but no one takes action. Most of the time, this is because you’re either not giving them a clear action to take, or you’re asking them to take a single action that they’re not ready to take.

That’s where the magic of the super signature comes in. It allows you to offer three or four “next steps” in a non-salesy way, and let the prospect choose what’s right for them.

We used to put a single, specific call to action in our email newsletters. Since switching to the super signature we’ve seen the number of people engaging with our offers increase by two and a half times.

What offers should you put in your super-signature?

I had a feeling you were wondering that, and well you should. Putting just anything in there won’t serve your purposes, and won’t benefit your subscriber.

You want to think about three (or at most four) offers that go from low commitment to higher commitment, with the last offer being to reply to inquire about working with you and your firm.

The first offer is often going to be your philosophy or manifesto on how you solve the problem your clients face.

The second should be a higher level of commitment. I prefer using a webinar, that you either have running on-demand or present on a frequent schedule. This requires a commitment of time on the part of the prospect, and often gives you an excellent opportunity to convert subscribers into sales appointments.

You’ll see in the example, we actually use my latest book as the second offer, then put our webinar in at #3, and the “work with us” offer is a fourth. But remember, three is optimal, and don’t go over four.

If you want to implement this in your own template, here’s some HTML you can copy and paste. (Remember, put it between the message content and the footer.)

<div class="post-s">
	<p><strong>AND...</strong> Whenever you're are 3 ways we can help you [insert how you help clients]:</p>
	<p><strong>1. [Insert your low-commitment offer here] - <a href="">Click Here</a></p>
	<p><strong>2. Tune-in to the next [insert your webinar or higher-commitment offer here] - <a href="">Click Here</a></p>
	<p><strong>3. Work with us One-on-One.</strong> If you're ready to [describe result you deliver for clients], hit reply to this message and put "1-on-1" in the subject line. Tell me a bit about your situation and your goals, and I'll get you all the details.</p>

OK… now, let’s talk about how to segment your list.

Email Segmentation Strategies for Service Businesses

cartoon of manager segmenting customers
Segmentation is really just a fancy word for treating prospects as individuals. The goal is to know what to say to every subscriber and when to say it. Let’s look at how to do that, without overcomplicating things.

Back in 2006 when I first found Infusionsoft it had this ability to sort contacts into all these buckets called tags.

Tags were amazing. You could add and remove them easily. You could have as many as you wanted. You could even organize your tags into categories.

I soon discovered that I could tag people who clicked a certain link in an email, who filled out a form, who had an interest in this or that. It was so exciting that I sat down and mapped out an entire tag structure, which I ultimately published as an ebook.

But there was a serious problem with this business of tagging contacts.

Soon, we hit tag overwhelm. We had so many. A lot of our tags (essentially groups of contacts) were documented, but even more were not. It seemed innocent enough. We’d create a tag for something that seemed important to track, then, six months later we had no idea what the tag meant.

Some tags had zero people, some had just one or two, and a few had everyone in our system.

What a mess. And it missed the whole point.

The purpose of segmentation (and tags are a way to do that) is to help you know who should get which message, and when they should get it.

For most businesses, that’s actually pretty simple. But, now with over a decade of experience segmenting our own CRM, and untangling the CRMs of dozens of clients, I can tell you with confidence that there are two approaches to segmentation “in the wild.” See which one fits you…

Approach #1: You have a newsletter segment, and not much else.

Approach #2: You have 1238 tags/buckets/categories and it gives you a headache every time you open your CRM because you have no idea which tags you need right now. (Heck, you probably look at most of them and don’t have a clue why they exist…but you’re afraid to delete them aren’t you??)

No matter where you are, I’m here to grant you segmentation absolution. It’s time to start with a clean slate.

How to create meaningful segmentation?

There’s an important word in that headline, did you see it? The word meaningful. That’s what we’re going for. You don’t need to track everything. You won’t use it. The only businesses I’ve ever seen that could justify having hundreds or even thousands of segments are businesses with over 50,000 subscribers. If that’s not you, let’s figure out how to create simple and meaningful segmentation.

Reverse Engineer Your Sales Process

The way to approach this is to start at the end of your sales process and work backwards towards your new leads. This is often the opposite of what most do.

Pull out clients first.

So, starting at the end, we begin with a segment for your clients, active and inactive. You might tag them like this:

CLIENT – Active

CLIENT – Inactive

Track sales conversations.

Next, you want to segment all of the people you’ve had a sales conversation with and (possibly) sent a proposal to. There are a few more options needed here.

PROSPECT – Scheduled Consult

PROSPECT – Completed Consult – Not a fit

PROSPECT – Completed Consult – Proposal Out

PROSPECT – Completed Consult – Didn’t Close

We could add five or eight more categories to track nuances of the sales cycle, but I find that it usually just adds extra work and overhead, without any real value. Unless you’re doing dozens of proposals a week or month, these four tags will be enough.

Why these categories? The first is rather obvious: you want to know who has scheduled a consultation or sales call.

Then, it’s important to know which contacts you’ve spoken with and determined are not a fit (for some reason, these tend to keep coming back, so it’s a useful filter). It’s also helpful to know who you have sent proposals to—these people need daily attention. And finally, you want to know who seemed like a fit, but didn’t close. Often, if you stay in touch, they’ll come back around.

Identify the key step before the sales conversation.

This is where it becomes difficult for most businesses. They don’t know what really happens before the sales conversation. Prospects just show up at random intervals. That’s a completely different problem that I address in my guide to selling professional services.

For now, let’s assume you’re following my advice and using a presentation to turn prospects into appointments (a webinar or live seminar). That’s a key milepost on the buyer journey.

So we need to identify who’s passed the milepost.

Here’s how to do it…

WEBINAR – Registered

WEBINAR – Attended within 30 days

WEBINAR – Attended within 60 days

WEBINAR – Attended within 180 days


Remember our goal—to know who the important people are right now in our CRM. That’s why knowing who’s attended a presentation within the last 30 days or 60 days or 6 months is vital. If someone attended two years ago, I don’t care. That action is no longer relevant.

In marketing terms we’ve just tagged for “recency.”

Is anything else important? Funny you should ask. It’s also important to know how many times someone hits this milepost in our sales process. Why? Because we’ve observed that prospects will often get to this point in the sales process and then attend the same presentation three to five times before scheduling a consultation.

Seems silly, but it happens. These prospects are selling and reselling themselves on making the leap and working with you. And we want to know who’s exhibiting this behavior.

There are two ways you could do this. The simplest way is to create six tags:

WEBINAR – Attended 1

WEBINAR – Attended 2

WEBINAR – Attended 3

WEBINAR – Attended 4

WEBINAR – Attended 5

WEBINAR – Attended 5+

Then use an automation to add and remove the appropriate tag, based on the existence of the previous tag. For someone who has already attended two webinars and has now attended a third, the logic works like this:

If contact has the tag “WEBINAR – Attended 2” then remove tag “WEBINAR – Attended 2” and add tag WEBINAR – Attended 3”.

You then setup similar logic for all six tags.

The other way to implement this in ConvertKit is to create a custom field called “Webinar Attendance Counter” and each time someone attends a webinar update that field using some Liquid code like this:

{{ subscriber.webinar_attendance_counter | plus: 1 }}

Then you can simply create a ConvertKit segment (like a saved search) to pull all contacts with a “Webinar Attendance Value” of 5 or more.

If you use another tool, there is likely a way to accomplish something very similar.

Finally, identify your subscribers.

This is the proverbial “top of the funnel.” It’s important to note, that when someone jumps into one of the buckets we’ve already discussed, they should be removed from your subscriber tag. That DOES NOT mean you stop sending them your regular communication. In this case “subscriber” describes the lowest-priority place—the starting point—on the buyer’s journey.

And, if they jumped up to the level above by attending a presentation, but haven’t attended one in six months, I’d move them back to “subscriber” status, so you can focus on only the prospects who are acting interested now.

The only people I would never bump back down the ladder of categorization are customers/clients. Once a client, always a client. They might be inactive, but you’ve done business. You want to know who these people are and treat them differently.

Do you need more than this?

It depends. I’d only add more when absolutely necessary, and only when you know how you’ll use the information. That’s where most people get into trouble with segmentation. They think, “I’ll track everything, in case I ever need it.” This is a huge mistake. Most never use all of this, yet they’re saddled with the operational overhead from all of these categories.

And it’s easy to assume that “it’s just tags” but there is a factor of maintenance that’s necessary, and honestly, a factor of confusion and overwhelm that comes from having hundreds of seldom used tags.

If you do add to what I’ve laid out here, this is how I would do it.

First, I’d focus on clients/customers and tag them based on the product or service they purchased (one for each product or service).

Second, I’d create a list of no more than five areas of interest that would help you know what topics you should send to a particular prospect.

Third, if you have different groups of prospects, or different size companies, or some other demographic grouping that is an important qualifier, I’d consider adding that. Here’s how we handle industry and company size.

BIZ TYPE – Accountant

BIZ TYPE – Consultant


BIZ TYPE – Marketing Agency

BIZ TYPE – Financial Advisor

BIZ TYPE – Other


BIZ SIZE – 2-10

BIZ SIZE – 11-25

BIZ SIZE – 26-50

BIZ SIZE – 51+

We use the fewest meaningful categories to describe the information we need.

The First Four Email Automations You Need

marketing automation cartoon
So many business owners get excited by the possibilities of marketing automation, but soon find themselves tied in knots when they try to implement all these whiz-bang workflows. In this section, we demystify marketing automation so you can create what you need.

Last year, I was interviewed on a podcast. Great host, great show. Then, about six months after my episode was published, I got an email from the host letting me know my episode was live (note, the email was six months late).

Then three days later…same email.

And three days after that…same.

And again, and again…for six weeks.

And if you’re wondering, yes, I did let him know that his email robots had run amuck.

I’ve had weird things happen with automation, too. And that’s the big danger with massive automation. If you’re not careful you begin to build conflicting logic in your tangled web of automations, triggers, and rules.

I find that most entrepreneurs are missing the basics. And, if you do these basics exceptionally well, you often don’t need much beyond them.

So, build these four with excellence, then carefully add simple automations, only as needed.

Automation #1: The Welcome Email

This is just about as simple as it gets (on the surface). Someone subscribes to your list, they get a welcome email. I’m not talking about an email that delivers whatever they opt-in for—report, download, lead magnet.

The welcome email is designed to orient the brand new subscriber to you, your business, what you stand for…and to point them deeper down your rabbit hole.

And that little twist means you need to think about how to track who’s been sent your welcome email (or welcome series of emails), and who has not.

Here’s how we do it…

First, create an automation rule that triggers for each one of your forms, and has just one action: Add a tag named “Welcome Sequence – Start.”

Here’s what it looks like:

What I’d really love to see ConvertKit add is a trigger option in visual automations for “any form.” That would eliminate the need to update this rule each time you add a form, but for now, be sure to add every new form to this automation rule.

This rule as it is will add the “Welcome Sequence – Start” tag to a person every time they fill-in one of your forms. Now we need to build a visual automation to act as the traffic cop—only sending the welcome emails to new subscribers.

Here’s how we do it.

Create a new visual automation, name it something like “Welcome Sequence” (original, I know ?).

Set the trigger to “When a Subscriber is Tagged With” and choose the “Welcome Sequence – Start” tag you just created.

Now, everyone who fills out a form will trigger the automation rule, which adds the “Welcome Sequence – Start” tag, and triggers the Welcome Sequence visual automation. (Sounds confusing, I know.)

Now for the “traffic cop”…

Add a condition below the trigger in the visual automation, that asks “If the subscriber is tagged with” and choose (or create) a tag named “Welcome Sequence – Completed.”

If the person has this tag, we’ll bypass sending the welcome emails (because they’ve already received them). But, if they do not have the tag, we’ll send the welcome emails.

Here’s what it looks like in the visual automation builder.

convertkit visual automation tool

Next, we simply need to add our welcome email sequence, and do some tag cleanup.

Note: If you’re new to email automation, one of the best habits you can acquire is to always cleanup tags at the end of an automation. If you don’t you’ll end up with contacts that have dozens of meaningless tags, that you’re afraid to delete because you can’t remember what they do. (Speaks from experience…)

Piece of cake. Automation #1, ✅.

Automation #2: Email “Training”

All over marketing land you’ll hear you need a “lead magnet”…some downloadable report or PDF cheat sheet.

I’ve used them for 10+ years and they do get people to opt-in. Especially if you use a really jazzy headline filled with curiosity. And opt-ins are great for sure, but here’s what I’ve observed over the years—many people opt-in, get the thing you’re offering, then never engage again.

We could just chalk this up to the idea that to get really good prospects you have to cast a wide net and you’ll capture some duds, too. And there’s some truth in that, but I’d prefer to optimize my entire marketing and sales process for quality.

And while we’re at it, I want to optimize for people who will interact with me and my firm in the way that we choose to market. For us, that means we need people who open, read, and click stuff we send in email.

Why this focus? Simple, I know that to land a new client I need to be able to communicate with a person repeatedly, over time. The most reliable way to do that is email (sorry Facebook ?).

So, we want people on our list that read email. And we need to “train” them right off the bat to think, “Oh, another email from Steve, I wonder what he has for me today?”

So where is all of this going, you ask? Simple, match your bait to the action you want your future clients to take. In this case, the immediate action is that we want them to look forward to our emails. And, the best way to do that is to get them to opt-in for something delivered by…wait for it…EMAIL!

Excellent. Now, how do we accomplish all of this? Simple, offer as “bait” a 5-day email course. Could it be longer? Sure. Shorter? Probably not. But 5 days (5 emails) is usually something you can implement in a day.

What to write in your emails.

Ah yes, the eternal question: “What shall I write?” The first impulse is to explain everything there is to explain about what you do in the course of five emails. The problem with this isn’t so much in the emails themselves, but in framing the promise of your 5-day email course.

For my business, if I said, “hey, signup for a 5-day email course and I’ll tell you everything that you should know about marketing” no one would signup. No, instead, you need to have the power of specificity.

How to use the power of specificity to increase opt-ins.

Specificity—being specific—is really about choosing one thing, out of all the things you’re an expert at, and focusing on that one thing alone. So instead of using an email course to tell you everything you need to know about marketing, instead I might focus on the idea of pre-selling. And build an email course on how to pre-sell prospects, so you don’t have to “sell”.

And instantly, there’s more interest, there’s more pull. Instead of being vague, we’re focused and promising to deliver one specific result in five short emails.

What’s your end game?

Before we get to a structure for your email course, we need to be clear on the outcome we want. Typically, you’ll want to move a prospect from “subscriber” to the next key milepost in your sales process.

In our case, that means getting them to register for a webinar, while making it clear for ready-to-buy prospects that they can book a call with our team to get started. Whatever is the appropriate next step in your sales process, write it down, and get really clear on the specific action you want a subscriber to take next.

A framework for your email course.

Let’s simplify creating your email course. It’s just five emails, and they don’t (necessarily) need to be long. Five hundred words is often plenty. One thousand words is long. So don’t feel like you have to write your magnum-opus.

Email 1 – The benefit and philosophy.

In the first email, you need to restate the benefit to the reader (or big promise you made) that caused them to enroll in the course. You’re affirming their good decision to trust you with access to their inbox.

You also want to share your unique philosophy (way of thinking) about what you’re about to share in the next few emails. This frames the rest of the material and gives the reader the “why” behind what you’re sharing.

Email 2 and Email 3 – One Idea + One Action

In each of the next two emails you want to share one idea that leads to the result you promised when the subscriber joined your course. Ideally, you’ll also give the reader a single action to take to move themselves forward towards the result.

It doesn’t need to be a big action at all. In fact, it’s better to ask them to do something small, but tangible. For example, if I were a consultant that worked with CEOs of small firms, I might explain the importance of tackling issues in the business based on priority, rather than when they come up. So the action would be—take 10 minutes Mr. CEO, set a timer, and write a list of every issue that needs to be fixed in your business that you can think of before the timer goes off.

That’s simple and achievable.

In the third email, you’ll build on the idea and action you shared in the previous email, following the same pattern of one idea and one action. Email 3 is a great place to insert a case study that illustrates the idea/action.

Email 4 – One Idea + A Next Step Action

At this point we’ve built some rapport with the potential client. And, we’ve laid the ground work for making a higher-commitment offer. For most service businesses this should be an offer to attend a presentation (probably a webinar).

The webinar should build on the content from the email course, so that registering would be the logical next step to continue the journey the prospect is already on.

If you don’t have a presentation, you can offer a consultation/call of some kind, but know that response will be low. And, you’ll need to sell the benefits of this call if you want any hope of getting the right prospects in the door.

Email 5 – Summary and Next Steps

Ok, you’re at the last email. This is your opportunity to summarize everything that you covered in earlier emails and emphasize the importance of taking action. And, of course, offering that clear next step—webinar or call or whatever.

And, in the P.S. let the subscriber know what’s coming next from you. How will you keep in touch—a weekly newsletter/article, a podcast interview, carrier pigeons. However you’ll be regularly communicating, let them know what to expect next.

Automation #3 – Do Something That Won’t Scale

I’m a big fan of automation when it makes sense. And I know that the best use of automation is when it enables you to create personal connections with people.

That’s what Automation 3 does.

When you subscribe to our list, you’ll get something surprising…a video message from me. And no, this is not some canned message. It’s really me, talking to you. Each one is custom and personal.

And no, it doesn’t scale, but I’m not trying to reach 100,000 people. I want to create real relationships with a much smaller number. That’s all I need to have a wildly successful business—and all you need too.

The people who will tell you you need a massive email list say that because they tend to develop very thin connections with their subscribers. They need a metric-ton of subscribers to make the financials work out. But you’re smarter than that. You’re focused on real relationships that won’t churn.

That’s where the video comes in for us. We use a cool tool called Bonjoro. It’s an app for your phone, and also works on the web.

To make it easy for me to send these messages, I’ve got to have a system that organizes all of our new subscribers and sets me up for efficiency.

Bonjoro makes this very easy. It has an integration for ConvertKit that’s easy to configure. It “listens” for new subscribers in ConvertKit, grabs the name and email address from ConvertKit and puts them into Bonjoro.

And Bonjoro gives me a nice list of everyone who needs to get a video. I have their name (most of the time), and I have their email address, which Bonjoro uses to send the video.

All I have to do is open up the app a couple of times a week and in under 30-minutes I can greet all of our new subscribers, individually.

(Note: if you subscribe and give no first name or something that looks like a bogus name, I won’t send you a video. Sorry.)

That’s all there is to it.

Automation #4 – New Client Onboarding

I’ll bet you weren’t expecting this one, ‘eh? To be fair, this is one automation that we’re usually late to implement when we launch a new service. We tend to handle onboarding manually until we sort out the right set of steps.

Then, once we have those steps, it’s fairly easy to implement this automation. And, it will not only save you a ton of time answering the same questions over and over again, you’ll also give your new clients great confidence because you’ll answer their questions before they think to ask.

What you’ll share in your onboard emails will vary greatly based on your business, and what the client bought. However, we’ve found that the following timing works well in most situations, and gives you lots of opportunities to communicate with new clients.

Sample Onboarding Sequence Timing

Email 1 – Day 1

Email 2 – Day 2

Email 3 – Day 3

Email 4 – Day 5

Email 5 – Day 8

Email 6 – Day 13

Email 7 – Day 21

Email 8 – Day 34

Email 9 – Day 55

Email 10 – Day 89

One tip—we like to create a private onboarding podcast to deliver the content. It’s usually far easier to speak the content, especially if it’s complex, than to write it.

That’s it. If you have those four automations in place, you can largely stop thinking about automation and focus on serving the people you’re trying to serve, while knowing that your key communications are running in the background.

Webinar Automations in ConvertKit (and Demio)

Webinars are one of the most effective tools for converting prospects into clients, yet setting up all of the technical details can be time-consuming. Let’s look at a “friction-free” webinar setup.

Why webinars? In most of the businesses we end up working with, there’s a gaping hole in their marketing. They may be sending a newsletter by email or snail mail, or they might have some regular schedule for posting to social media, or maybe they even have a podcast.

Those are all great. Yet, when we talk to these business owners they’re totally frustrated because their newsletter or posts or podcast aren’t converting passive subscribers into sales opportunities.

(I’d be frustrated, too…it’s a lot of work to pump out all that content to never see a significant return.)

So what’s missing?

The missing piece is what I call a “conversion event.” Something that happens at a specific point on the calendar (an event), that focuses the attention of your prospects on the problem they face, the very real consequences of allowing the problem to fester, and leads the way towards a solution. Then, offers the opportunity to get personalized help in the form of a meeting with you.

This is the bridge that carries passive subscribers over into your sales process.

I recommend running at least one webinar every month. In fact, when we were really ramping up our business, we ran one a week for nearly a year.

When you run frequent webinars there’s a big problem.

Setting up the webinar and all of the emails and automation is a lot of work!

To save time, we figured out a simple system that involves two automations and three sequences in ConvertKit that we can quickly clone, tweak, and launch. Here’s how it works…

Step 1: Automating Your Webinar Promotion

Once you set the goal of running a monthly webinar, the whole thing can quickly fall apart if you don’t plan for the promotion.

Writing promo emails can be time consuming, and after the first webinar, you might wonder, “What am I going to write to promote the next one.”

Create 3 webinar email campaigns

I used to run into this problem all the time. The webinar would be a week out and I’d be scrambling to write the promotion. Then I got smart…

I blocked a half-day, left the office, landed at my friendly neighborhood Starbucks and (fully caffeinated ☕️) I wrote three separate promotional campaigns.

Each campaign has four emails and is designed to be mailed on the Monday, Tuesday, Wednesday, and Thursday of the week of the webinar, with the webinar happening on Thursday afternoon (we usually start at 3pm Eastern on Thursdays).

Why write 3 webinar campaigns?

By batching the writing and getting three promotions done, we have the ability to rotate campaigns. We run a monthly webinar, so the rotation looks like this:

Month 1 – Campaign A

Month 2 – Campaign B

Month 3 – Campaign C

Month 4 – Campaign A

People on our list won’t see a campaign repeated for three months. Each time we re-send the campaign, we’ll tweak the headline to test something new, but the message remains the same.

The big objection to doing this is that people will complain. I can assure you, that is not the case. With open rates between 20% and 30%, we know that the majority of our subscribers didn’t see the campaign the first time it was sent. So, when it comes around again, it’s new to them.

Taking this one step will dramatically increase the likelihood that you’ll follow-through on a monthly webinar strategy.

Setting up your tags and form in ConvertKit

You can setup your tags on-the-fly in ConvertKit, but I find that it’s faster to create them all at once, before you do anything else. You need three tags for each webinar:

WEBINAR – WebinarName – YYYY-MM-DD – Registered

WEBINAR – WebinarName – YYYY-MM-DD – Attended

WEBINAR – WebinarName – YYYY-MM-DD – No Show

Sure you could track more, but I’ve found that this is enough, and adding more granular tracking doesn’t add much real value.

Next, setup a ConvertKit form. I know that ConvertKit seems to be moving to tags as the single method for segmentation and for triggering actions, but one of the things I really liked when I first started with ConvertKit was the idea that all subscribers enter through a form (even if they’re being added through the API).

So, I recommend you create a form named WEBINAR – WebinarName – YYYY-MM-DD. I like to add first name, last name, email, and mobile phone (for sending SMS reminders with Twilio) fields to the form. Only require the email field.

Next, you’ll want to create an automation rule that triggers whenever a contact gets the WEBINAR – WebinarName – YYYY-MM-DD – Registered tag you just created and adds them to the form you created.

Note: This is necessary if you use Demio, as we do, for presenting your webinar. Some other tools may add the contact directly through the form you just created, so this automation rule wouldn’t be necessary.

Set up your webinar tool

Before creating your automation in ConvertKit, I recommend that you configure your webinar tool. We use Demio, and I highly recommend it. I’ve tried virtually every webinar platform out there, and have been presenting webinars since 2007.

Demio is the simplest and the fastest to setup. This is extremely important if you’re going to be doing frequent webinars. You want to remove as much friction from the setup process as possible. Plus, they have fast and amazing support.

If you need a tool, and would like to give Demio a try, you can do a free trial using our partner link.

Webinar automation in ConvertKit

Inside ConvertKit you’ll start by creating a visual automation. I like to name them using this naming convention: (Webinar) – WebinarName – YYYY-MM-DD.

Our goal is to build an automation that you can clone again and again, so setting up webinars takes a minimum of time.

Inside the automation, the first thing you’ll create is a trigger. I usually trigger the automation with a tag named (Webinar) – WebinarName – YYY-MM-DD – START PROMO.

The mistake most make at this point is to have the first action add the subscriber to an email sequence and start emailing. We’ll get to that in a moment, but first, you’ve got to do some tag cleanup.

We use the same tags over and over inside all of our webinar automations. That’s a huge boon to productivity, and it keeps our tag list manageable. But, if you don’t clean up those tags at the start of the automation, you can create some serious bugs in your automation, and often never know it.

So the first thing we do is remove every tag we use in the automation (see image).

removing tags from a ConvertKit visual automation

After we remove the tags we insert a date delay and set it to the day and time we want the promo to start. This allows us to precisely control when the promotion emails will begin sending, and allows us to setup webinar campaigns months in advance.

When the date arrives, everyone in the automation is moved into the promotional email sequence. This sequence usually includes three or four emails and sends on Monday, Tuesday, Wednesday, and Thursday, with the webinar happening on Thursday afternoon. Occasionally we have to run a webinar on a Wednesday and we’ll just drop one of the emails from the sequence.

We’ve found that for our market we get a better show-up rate by using this short promotional window, versus starting promotion the week before. Your market may be different, so test it.

When a subscriber registers for the webinar, Demio tags the person through ConvertKit’s API, and that tag is set as an event, below the promotional sequence. This pulls the person out of the promo, and we then send them to a separate “post registration” visual automation.

Anyone who does not register for the webinar is taken to the end of the automation automatically using another date delay event set for two days after the webinar, and we clean up tags on all of those contacts.

Automating the post-registration experience

We let Demio handle all of the webinar reminders, and we customize them inside Demio. This ensures that everyone who registers gets the correct link to access the webinar. We could do it in ConvertKit, but honestly, it’s one more complication and we’ve tested both methods, with no difference in results. So, we take the path of least friction.

And, Demio makes it so simple to clone an event and automatically recreates all of your notification emails, and keeps all of your customizations.

With registration emails handled, the ConvertKit automation is focused on communicating with subscribers after the webinar, based on their behavior.

We break them into two groups. You could do more, and we have in the past, but we’ve found that the results don’t justify the extra work. So, we have one follow-up path for people who attend the webinar, and a different path for those who register, but don’t attend.


Those who attend get a link to book an appointment with us (the offer used on the webinar), and a link to the replay. And the no-shows just get a link to the replay. We don’t want to meet with them until they watch the presentation.

One of the ways we’ve made this automation very easy to clone and update for every webinar is that we dynamically insert the link to the replay into a ConvertKit custom field. This way, we don’t have to manually edit the follow-up emails, since the only thing that changes is the replay link.

This is a manual process that has to get done a few hours after the webinar, but it’s takes less than five minutes. Demio automatically records every webinar. It takes an hour or two for the replay to be processed and available in your account. And, they create a great, branded replay page and give you a link.

A couple of hours after the webinar, someone from my team will login to Demio, grab the replay link, then open our post-registration automation in ConvertKit and paste the link into a step in the automation that updates the custom “replay link” field for all of the contacts in the automation. Here’s what it looks like:

set Demio replay link in custom field

We tag everyone in the automation with (Webinar) – WebinarName – Replay Ready and they’re immediately updated with the replay link value and sent the follow-up emails.

Why all of these steps?

Good question! Webinars are one of the best tools we’ve ever used for connecting with future clients and giving them a reason to schedule a call to find out how we can help them. But setting up webinars has always been a huge time suck, complicated, and prone to mistakes that make you look plain foolish.

So we have looked for years for tools that combine power, with ease of use. With Demio and ConvertKit, we’ve found them.

By spending the time to create these automations, it allows us to setup 12 webinars for the year in under a day. Once they’re on the calendar and setup in the system, we know we’ll follow-through and reap the benefits (more and better clients).

A lot of businesses say they want to do webinars. Some even think they’re ‘doing’ webinars. But most businesses will only do one or a few webinars a year. That’s not nearly enough to create consistent results.

We’ve done enough webinars to know that clients will often attend the same presentation four or five times before hiring us. Why? They’re selling themselves on working with us. You need a system that allows them to do that. One that’s easy to execute on, so you’ll actually follow-through.

Advanced Segmentation in ConvertKit

Use all that ConvertKit gives you for segmenting your email list–forms, tags, and custom fields–and know when to use each one.

You could stop with all of the things we’ve covered so far, but if you’d like to make the most of ConvertKit, here’s where I’d go next.

In Part 2 of this guide, I talked about the importance of segmentation. To get segmentation to work, you’ll need some automations to help you keep track of it all. A word of caution, we’re about to get technical, so bear with me.

Storing Segmentation Data in ConvertKit

Before we get into automations we need to understand how we’ll store the information that will drive the automations. In mast cases, you could choose to use more than one of the three options to store a piece of information. Choosing the right one makes a huge difference in the complexity of the automation you’ll need to build.

ConvertKit has three ways to store information about a subscriber:

  1. Forms – Records whether a subscriber has completed a particular form or not.
  2. Tags – Can be used to attach any kind of “information indicator” to a subscriber.
  3. Custom fields – Used to store text-based values.

Of the three, forms are probably the simplest to understand. Either the subscriber submitted the form or not. We use them as entry points to our database. Everyone must come through a form. Even when using a 3rd party tool like Demio, which sends contacts to ConvertKit using the API and tags them, we’ll still add the person to the correct form. That way our forms hold the complete record of who opted-in for each of our offers. We can use that information in our segmentation and advanced automations.

Let’s look at the two more complex data storage options.

Understanding ConvertKit Tags

Tags in marketing automation software aren’t new. Infusionsoft had them when I first used it back in 2007, and tags were their killer feature. They give you limitless flexibility. And, with that flexibility comes complexity.

The nature of tags. A subscriber can have any number of tags—from zero to essentially infinity. And you can use tags to mean anything you want. So let’s look at some common scenarios.

Tags are particularly useful when a contact can have many values for the same data point. For example, interests. A subscriber might be interested in email marketing, webinars, cold email, and Facebook ads. So, I could have the following tags:

  • Interest – Email Marketing
  • Interest – Webinars
  • Interest – Cold Email
  • Interest – Facebook Ads

And any given subscriber might have none, a few, or all of those tags. Another example might be for tracking your webinars. Let’s say you want to know who attends each webinar throughout the year. You might have the following tags:

  • Webinar – 2019-01-17 – Attended
  • Webinar – 2019-02-14 – Attended
  • Webinar – 2019-03-21 – Attended

And so on…with one tag per webinar.

Again, the contact could have any combination of those tags and it would be valid.

Now, let’s look at an example where tags begin to be less than optimal. Imagine, we want to track the industry for a contact’s company. We might have tags that look like this:

  • Industry – Accounting
  • Industry – Law
  • Industry – IT Consulting
  • Industry – Business Consulting
  • Industry – Marketing Agency

In the real world each subscriber can only be in one industry at a time. Yet, it’s possible to add more than one of these tags to a subscriber at the same time. In fact, it’s possible to add them all.

Now, you might think, “Well how would that happen.” There are a number of ways, from prospects clicking the wrong industry in a survey (intentionally or not), to human error on your part, or by someone on your team. The point is, it can happen, and it does…often.

The problem occurs, when you’re using this information to drive personalized emails. Your automations either break, or they begin sending the wrong information to the wrong subscribers.

There are two ways to solve this problem. If you choose to stick with tags to store this kind of discreet value data, you need a “cleanup automation.” One that goes through every time one of the values in a set like the one above is added to a subscriber, checks for and removes all of the other tags if they exist on that subscriber.

The other solution is to use custom fields.

Understanding ConvertKit Custom Fields

Custom fields are the third option for storing information about a subscriber in ConvertKit. Coming from tools like Drip, ConvertKit’s implementation of custom fields feels like it’s still in its early stages.

You can create an unlimited number of custom fields, and each one holds a plain text value that you put in it. As of this writing, ConvertKit has recently updated it’s Zapier integration to allow you to populate custom field values through Zapier, which opens up a lot of new possibilities.

Custom fields are extremely useful when you’re working with subscriber “states”—situations where the subscriber can only be one of the many options at a time.

Our industry example above is one to solve with a custom field. Each contact can only be in one industry at a time. You’d create a custom field named ‘industry’ (I always keep the names in all lowercase and substitute underscores for spaces between words, i.e. ‘revenue_range’.)

It’s important that you use the exact same value every time you add or remove data from a field if you’re using it to hold discreet values. In other words, you’ll have mess on your hands if you’re tracking industry and get sloppy with your values for “accounting” and use “accountant”, “accounting”, “CPA”, “accounting firm”.

It can easily happen. The solution is to maintain a spreadsheet with all the possible values for each custom field. You can download an example that you can modify for yourself here.

The Problem with Custom Fields in ConvertKit

While custom fields serve an important role, there’s some functionality that’s missing from ConvertKit, that I hope will be addressed in the future.

First, managing custom fields (adding/removing them) is done on an individual contact record. So, you can open up any contact, add a custom field and it is now available for all contacts. While this is really convenient, it would be great to have a single, central place to manage your custom fields.

Second, because custom fields store plain text, there’s no data validation built-in. One of the real possibilities for custom fields in ConvertKit is in working with dates and numbers. You can use ConvertKit to store date and number values (as plain text), but you’ll need Zapier (or something like it) to do much automation with the info.

Third, while ConvertKit does use the Liquid templating language (which is awesome), there’s not a lot of documentation on what you can do with it inside ConvertKit. Yes, you can use it to conditionally insert blocks of text into emails based on tags, but it’s not clear how far you can go with using it to perform calculations and logic to update custom fields on-the-fly inside automations.

From our tests, we’ve found it’s possible to update custom fields using Liquid within visual automations, but not in automation rules. More documentation from ConvertKit on what’s possible with Liquid would give us the confidence to do more.

For now, we’ve taken a middle road. We’re storing values in custom fields, as we collect the information, hoping that in the future custom fields will be more capable. In the short-term doing this gives us the ability to implement some advanced personalization, which we’ll cover in the next section. And, we’re also mirroring the information in tags, so that we have more capabilities to drive our automations.

This is probably a deeper dive into storing data in ConvertKit than you might have wanted, but when you ignore this thinking, you soon end up with a spaghetti mess of tags and fields, that becomes difficult to manage.

Now…on to next-level automations.

ConvertKit Automations That Will Make You Money

Once you have the basic automations running, you can add these three money-making email campaigns to plug the holes in your marketing funnel.

In this final section of of the article, we’ll look at three automations that will make you money. I recommend you implement them in the order we’ll cover them here. These are designed to help you make the most of your lead flow.

The Past Client Win-Back Campaign

So you finished up work for a client, they’re happy and they go off into the world with whatever it is that you did for them. Great!

Now what?

How do you stimulate repeat business? The simple answer is to stay in-touch with good follow-up. But you have a relationship with these clients. You know things about their businesses and about their future plans.

It would be a mistake to treat them like just another prospect. Here’s how to handle your past clients.

First, make sure they are on your general newsletter list (at a minimum).

Second, using a visual automation and delay timers in ConvertKit, schedule a standard set of follow-up activities. You’ll need Zapier to make this work, but here’s the flow.

  1. Create a visual automation that’s triggered on the application of a tag: ‘Client – Inactive’.
  2. Inside the automation setup delay timers as follows: 30-days, 15 days, 30 days, 25 days, 45 days, 60 days, 25 days, 35 days, 50 days…you could continue with as many timers as you want. This sets up a semi-random follow-up pattern that is more frequent in the short-term, right after your engagement, and less frequent as you move out into the future. But notice, it’s not spacing any two touch points more than 60 days.
  3. After each delay timer add a tag ‘Outreach – Contact Past Client Now’, then add an action to remove the tag 10 days after it’s added.
  4. In Zapier, create a Zap to listen for the tag ‘Outreach – Contact Past Client Now’ being applied to any subscriber, and have it add a task to your to-do application or have it email you a reminder.
  5. At the end of the automation have a goal that removes the past client from the automation if they become an active client again.

What to say at each touch point.

You’re probably thinking, “That’s great, I have a reminder to follow-up, but I don’t know how to follow-up.” There’s certainly a big gap between good follow-up and being annoying. Getting into all of the possibilities is beyond the scope of this article, but I’ve released a new book on the topic called The Follow-up Formula (complete with follow-up templates).

In general, there are two ways to follow-up that will work in virtually all situations:

  1. Ask an easy to answer question. Sometimes this can be as simple as “Hey Bob, I was just thinking about you. What are you up to this month?”
  2. Be valuable. You know the things that your clients are struggling with in their businesses/lives. Find information that will help them, and send it.

These are personal emails, text messages, or phone calls. The trick is to use ConvertKit to control the timing of these contacts, so you don’t let one slip through the cracks.

The Strategy Call Pre-Sell Campaign

This campaign is designed to prepare a prospect who has booked a strategy call with you. You’ll want to send case studies, your service prospectus, articles, and other information to help the prospect get fully informed about the benefits of the work you do, before the meeting.

This will eliminate much of the selling that’s required, and allow you to focus more on the problems and challenges your prospect needs help with, making your sales meetings more productive and efficient.

The pre-sell campaign should be triggered when a subscriber books a strategy call. If you’re scheduling these appointments with an online scheduler (we use Calendly, but most any will work) then you can use the scheduler along with Zapier to add a tag to a contact when they book a call: ‘Strategy Call – Booked’.

Note: You’ll want to configure your scheduler to allow at least a week between when the call is booked, and when it takes place, but not allow calls to be booked many weeks or months into the future. This will give you enough time to send the pre-sell material, but not so much time that the prospect will forget why they booked the call (it happens).

Here’s the flow for the automation:

  1. Trigger the automation when the tag ‘Strategy Call – Booked’ is applied.
  2. Add the ‘Locked’ tag. I like to use a locked tag to prevent any other promotional emails from being sent to any prospect who’s scheduled a call with me. It just muddies the waters. This tag is then used to filter out subscribers with the Locked tag from other promotions.
  3. Send an email sequence with three to four emails over seven days:
    • Email 1: “Looking forward to our call, here’s what to expect.” Explain how the call will be run and explain what you’ll cover, and what decisions will be made during the call.
    • Email 2: “Success Story.” Send a success story from another client, who’s seen great results from working with you. This can be text, video or audio (I prefer audio).
    • Email 3: “The Prospectus.” Send your service “prospectus”—a document that describes what you do, your unique method for delivering your service, and includes testimonials. This will answer many of the questions you’d otherwise have to deal with in the meeting, and if written well, will address the most common objections you hear from prospects.
    • Email 4: “Frequently Asked Questions.” Address the most asked questions about your service.
  4. Remove the locked tag 3-4 weeks after the last email. There’s no easy way to use a dynamic date in ConvertKit—i.e. the date of your strategy call. But, you still want to make sure you remove the Locked tag, so the prospect can receive future promotions. Usually, waiting 3-4 weeks is enough to get you past the sales conversation and decision window.

The Automatic Sales Stage Tracker

The last of these advanced automations is what I call the Automatic Sales Stage Tracker. Most businesses have just two sales stages: prospect and client.

But that’s not very helpful when you’re trying to figure out who to connect with in your pipeline. As you already know, I’m a big believer in using webinars (or live seminars) to sell services. They just work, and they’re relatively simple to master.

So we recommend building your stages around your webinar as the primary indicator of position in your pipeline. So, here are the basic stages:

  1. Stage – Subscriber. Someone who is simply a subscriber to your list.
  2. Stage – Webinar Attendee (90-days). A subscriber who has attended a webinar with the last 90 days.
  3. Stage – Webinar Multi-Attendee (90-days). A subscriber who has attended multiple webinars within the last 90 days. This is usually a very valuable group. You want to know who they are.
  4. Stage – Booked a Strategy Call (90-days). A subscriber who has booked a strategy call within the last 90-days.
  5. Stage – Booked a Strategy Call (>90-days). A subscriber who booked a strategy call more than 90 days ago.
  6. Stage – Completed Strategy Call – Didn’t Close (<6mo). A subscriber who completed the strategy call less than 6 months ago, was a good fit, but didn’t close.
  7. Stage – Completed Strategy Call – Didn’t Close (>6mo). A subscriber who completed the strategy call more than 6 months ago, was a good fit, but didn’t close.
  8. Stage – Completed Strategy Call – Not a Fit. A subscriber that, after meeting with him or her, you decide isn’t a fit.

Stages 3 through 7 often hold hidden money. The people who had enough interest to attend multiple webinars or book a call, but for whatever reason, didn’t become a client will often come back months later. But, if you haven’t segmented them out, you won’t know who to follow-up with.

With this group, the name of the game is to continue to show up and be valuable. Bring new ideas, new resources, and new connections. You get them close to the finish line, don’t give up on them unless you decide they’re not a fit for you.

You can use an automation similar to the Past Client Win-Back campaign to ensure that prospects in these groups stay on your radar.

We’ve covered a lot of ground in this guide. Here’s a simple checklist to get you moving in the right direction.

  1. If you don’t have a ConvertKit account, you can get a free 30-day trial here. If you book using that link, ConvertKit will send me some coffee money. ?☕️ If you’d prefer to keep me under-caffeinated, you can Google ConvertKit and signup.
  2. If you want to learn my strategy for pre-selling clients (so you don’t have to sell) check out my guide to selling professional services.
  3. Share this article with your network…

If I offered to write a great lead-generating book for you in the next 60-days would you take me up on that offer?

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