20 Email Marketing Automation Concepts from Brennan Dunn's Mastering Convertkit
If you're interested in teaching what you know and developing a healthy audience of customers that are genuinely achieving their desired outcomes, Brennan Dunn's Convertkit Masterclass is an excellent place to start.
Mastering Convertkit isn't a simple "how-to" of using the specific email service provider (Convertkit), but in Brennan spilling ALL of the beans in terms of how he thinks about email, product development, marketing, customer service, and generally making a living online as a creator.
Mastering Convertkit provides several "bonus" workshops that are recordings of live sessions Brennan gave to dive deeply into the most valuable aspects of his overall email strategy. One of those videos is title 20 Automation Best-Practices and Recommendations and is by far the best introduction to marketing automation, and more deeply product development, that I have ever seen.
These are my notes from the workshop. They contain my context with a focus on selling online learning products/courses.
The Big Ideas
These are several of the big ideas that Brennan identifies throughout the workshop.
💡 Dialogue before Monologue
You can sit down and bang out a "course" without ever talking to anybody, but the odds of that producing something effective and valuable that actually achieves desired learner outcomes
what i know 👉 meets 👈 what you need
💡 Things that don't scale like 1:1 conversations and consultancy provide the foundational work for more scalable and focused offers
Talking to learners is critical, otherwise you're just guessing.
Stop fucking guessing.
💡 If you want to personalize you need to have effective segmentation in place first. Segmentation is the foundation personalization is built on.
Personalization is an optimization and isn't something that should even be considered if you haven't done the work to truly understand your customers through dialogue and segmenting accordingly
💡 Use live workshops to create a more effective and higher quality course
this is a consistent pattern that is recommended by multiple sources and also matches our experience in general
workshops are a practice space practice and iteration are essential for creating an effective product that will achieve desired learner outcomes
💡 focus on creating customers and less on persuasion^^
The goal isn't to convince or persuade people into a sale.
The goal is to create a customer.
A customer has a relationship with us.
When we create a customer we are helping them achieve their desired learner outcomes.
For our customers we apply the Strategy of Preeminence.
💡 Audience growth and sales will both be positively affected when you move from one-to-many (broadcast sent today) to one-to-one (THIS email sent to THIS person about THIS thing they care about)
one-to-many is a newsletter model where you acquire subscribers
one-to-one is a process where you provide your customers what they need now and a clear way forward with obvious next steps and mutual buy in to a process
What is Marketing Automation?
In this presentation Brennan specifies that we are talking about marketing and sales automation, specifically tooled around an email list. This is as opposed to onboarding, support, invoices, or general onboarding.
That said, I think that what Brennan is discussion is very specifically about designing the long-format onboarding process that produces really great user experience and helps your customers achieve the outcomes they are looking for in their lives.
1. Seed Your Email List - Don't bank on Google (SEO
You can't rely on Google and luck to build your business. Your email list is where you eat, and everything you are working on emerges from the email list.
Your list isn't an orange that you squeeze juice ($$) from. Instead you can think of your email list as building a relationship between you and your customers and a vehicle for helping them achive their goals.
Your email list isn't a newsletter. Unless you are delivering topical news as a journalist, it's likely that nobody really cares about the newsletter aspect of your email list.
Your email list is a delivery mechanism for valuable assets that folks are willing to trade their email address and atention for.
When people sign up for your email list they are starting a long-form process.
Nobody is signing up for an email list excited about the prospect of future emails 🤣
If you're wondering how you build an email list the instinct might be to build a landing page with a pretty form and hope Google does the rest.
Instead, for your first 100 subscribers, you can reach out to folks individually and encourage them to join. Take some time to understand what they need and how you can help them, and use that as the pitch.
Follow through.
Don't even think about automation or personalization before the 500 subscriber mark. We are working the long game here. Manually.
You can also borrow other people's audiences by writing guest posts or going on podcasts. You aren't going in hot with a sales pitch, but talking about your reseach and expertise and how you are using those to help people achieve their desired outcomes.
Think about who can benefit from what you are building/researching and how you can get in front of their audiences.
2. Optimize for things that don't scale
We are talking about conversations. 1:1. Working the processes you are designing with individuals from start to finish. Get them where they want to go and validate that the processes you are designing are actually effective and not just guesswork.
We are encouraging dialogue and avoiding droning on with our own assumed monologue.
This is the "in the trenches" work and not automated workflows, but it's critical to focus on these fundamentals to make sure what you build is something that actually works and helps people achieve their desired outcomes effectively.
3. Don't shy away from 1:1
Dialogue >>>>>>>>>> Monologue
This is something that Brennan repeats consistently throughout the entire workshop.
You've got to talk to your customers. 1:1. Repeatedly.
These conversations are going to be the most valuable input you'll have to creating something truly valuable that actually works and helps people achieve their desired outcomes.
Many people make the mistake of focusing on growth too early. Quantity.
Instead, we can focus on quality.
what i know 👉 meets 👈 what you need
When you have low signups, 10 or so a week, take that as an opportunity to literally google everybody that signs up. Send them individually tailored invitations to chat on Zoom so that you can learn about their goals and desired outcomes.
Pitch them your current offer (a workshop, guide, etc) directly when it's appropriate ro use what you learn to craft a valuable asset that meets the needs of the folks signing up to your list.
You can do this without a fancy landing page, sales funnel, checkout, or delivery mechanism.
Sell it live. Directly. Through direct 1:1 conversations. Scale it through iterations of this process.
4. Don't focus too much "hard" segmentation
Your assumptions about your audience are probably incorrect.
Even if you've got a large list, you're probably making incorrect assumptions about their desired outcomes (WHAT they want) and WHO they are.
Once you've spent time with the 1:1 conversations, you can start asking for open-ended replies to your emails.
These replies can be used to gather voice-of-the-customer data that you can catalog and use in future messaging.
Brennan has a great video on YouTube focused on gathering the voice-of-the-customer data.
5. Build Everything in the Open
This is a powerful tactic that doesn't always come naturally or obviously. We often feel like we need to hide what we are working on because it's not "done enough" or might lead to other people snatching our ideas and beating us to the market.
Working alone in a cave often results in shipping nothing at all!
Self-doubt and fear set in.
You put in a ton of work and create something big...
but nobody wants it ðŸ˜
Confidence is built through iteration and doing the work to create successful processes for your customers.
It truly sucks to spend a lot of time, energy, and sweat on building something that nobody even fuckin wants.
Instead, you can involve your audience in the process. You can share your research, your drafts, your fledgling processes with the folks you can help. This can create a vested interest for your potential customers in what you are creating.
You are a curator, the researcher-in-chief blazing trails and sharing what you learn as you learn it so that people can use it RIGHT NOW and not at some distance point in the future when you finally release a polished product.
This feedback loop is valuable to you because it provides continuous wins, grows trust with your audience in your expertise and ability to deliver, and will ultimately lead to more sales when your product is released 🌀
6. The Scrappy use of PSes (Postscripts)
If you've ever got email from Brennan than this is familiar. He's always got a PS that point to something interesting that he is offering that you might be interested in.
A workshop, a guide, an event, an appearance, a product, whatever it may be there is always something down there making a little offer. A soft sell for us to opt-in to.
Brennan used this approach to iterate on small scale live workshops that netted over $100,000 for one of his products!
The formula Brennan describes is:
- Offer an interesting proposition in the PS and let them know they can reply to find out more.
- Manually sell them on your workshop or other offer. 1:1. Not a landing page or sales form. You are pitching an offer and sending a payment link with your own two hands.
These workshops are practice sessions for your final product that bring immediate value to a subset of your audience that you can refine into more repeatable general solutions for others.
7. 🌀 Consult -> Group work -> Live workshop -> Cohort-driven course -> Evergreen course
This is the sequence of offers that Brennan recommends for developing a high-quality evergreen course product that successfully achieves the desired outcomes of your customer. Each of these offers iterates on the last using what you learn to focus on the processes that are most effective for the audience they can most help.
Consult
Consulting is using your expertise in a very high-touch way to help individuals (orgs or people) achieve their desired outcome.
They have a specific context.
They need your expertise to get from where they are to where they want to be.
This is a bespoke crafted experience where you are likely contractually responsible to deliver value and help your customer succeed.
You aren't just providing a service though, you are using this as a research opportunity to refine a process and deliver value in a more general way.
Work with groups
I think of this like a knowledge adventure club where you are designing a module and taking a group of learners on a journey with a shared desired outcome.
Generally these are going to be over a period of time versus a single session and the individuals in the group will require different solutions and research to achieve the outcome in their context.
It's like a round table versus the more refined workshop experience that comes next.
Live Workshops
Workshops are condensed and more specific than the group/clubs. A workshop is typically 1-2 days of intense work towards a specific goal.
With workshops, this might be the first of these offerings that includes a landing page of some sort. An interest form, or some other ways for the gneral public to express interest in attending versus an invitation only experience.
A landing page isn't require to run a successful workshop and only a handful of folks need to attend for your to learn a ton about the process you are offering to help people with to achieve their outcomes.
Cohort-based "Flipped Classroom" (recorded)
Now that you've done the process with individuals and groups, you can often refine the outcome to something more specific that can be recorded into a set of videos and offered to small groups that want to work though it together.
This is a prototype of the self-paced evergreen style course that you'll ultimately offer and can be more rough around the edges.
Notion is a great venue for these sorts of course prototypes.
Self-Paced Evergreen Course
This is your product. A refined repeatable process that you are offering to the world of folks that want to achieve a specific outcome.
You can't get here buy avoiding the things that don't scale.
THIS IS NOT YOUR STARTING POINT
Do the work, iterate, and produce something that is actually effective and people will trade money for access to the process.
8. Pre-Launch - Find out WHO people are and WHAT they want
WHO: Understand how the people on your list identify themselves WHAT: Understand what difference they are attempting to make in their lives
Before you launch a product you can use survey segmentation and directly ask folks WHO they are (or want to be) and WHAT difference they are hoping you can help them achieve.
The WHAT is how you will craft your pitch.
This is a great opportunity for segmentation.
We don't need fancy automation or extensive liquid template conditionals.
Write a single pitch for the largest WHAT you've identified. Copy it 2-3 times and rewrite the same pitch for the next few WHATs that you've identified.
The WHO data you've gathered will influence the language and jargon that you will use.
9. Share what you learn in your build-up
As you gather WHO and WHAT data you can share what you are learning with your audience and demonstrate that you are listening and that they have been heard.
10. Don't go overboard with personalization
Personalization is an optimization!
You need to have fundamentals with segments in place before you can successfully start to personalize.
If you can't identify 2-5 segments and how well they are converting with your baseline/generic pitch, then it's likely you need to focus on those fundamentals instead of personalization.
Use the manual cut-n-paste method, but don't invest in heavy automation or templating yet.
You should be able to superimpose your segmentation data on top of your conversion data and undeerstand which of the segments you've identified are converting into customers.
If you can't do this, work on being able to.
11. Don't bother with a bunch of lead magnets
JOIN MY NEWSLETTER is a shitty pitch. Stop.
Alternatively:
- Signup up and I'll send you X right now (better)
- Sign up and we will work together to achieve X over time together (best)
Getting something right now is OK, but embarking on a learning process journey to achieve a specific goal? That's better for sure.
Often people will create many lead magnets, but you can usually reframe/reuse an existing lead magnet for WHO and WHAT segments.
Get a 21-day personalized plan of action for WHAT_THEY_WANT_TO_ACHIEVE specifically designed for WHO_THEY_ARE like you
This only works if you've got solid segmentation data in place.
12. Focus on Creating Customers
Customers aren't numbers on a list. They are the folks that trust you and the process that you have prepared for them to get them from where they are today to the WHAT they are working towards.
Your 1:1 work through coaching, groups, workshops, and other process development is part of the key to developming successful customers that are seeing the difference they desire happen in their lives.
The last thing you want to do is pitch somebody before they are ready to buy because you risk them not being successful, not buying at all, or often unsubscribing entirely.
Work more directly with your customers to make sure that they are seeing the promised difference in their lives as much as possible until the results are proven and repeatable.
13. The Shortcut Versus the Long Road
If they don't buy from you, but are still working to see the difference WHAT will make in their lives, what are the alternatives?
How are they achieving this change in their lives today, without you?
What's the long road, and how can your process be the shortcut?
"Go with us, or figure it out on your own."
14. Ask people why they don't buy
Just ask. Many people don't and you can learn a lot.
Assuming you can tell, once you've completed a pitch you can simply ask folks that don't buy in "why?".
Find out why they didn't buy in their own words and then correlate those reason to the WHO and WHAT segments you've already applied to them.
Fix your offer and pitch accordingly.
15. Live Launches Don't Always Make Sense
Live, general admission product launches are standard.
They provide a solid burst of income, but aren't always the best way to serve your customers.
Instead, you can glue together the process of creating customers with providing the shortcut to a long road and a personalized pitch when they are ready to hear it.
This allows people to self-select when they are ready to enter the process you've designed for them to achieve their WHAT.
16. Discount, Bundle, and Supply
The three types of launches are:
- discount: buy now or pay more later
- bundle: buy now and get extra exclusive cool stuff
- supply: buy now or miss out because it's going away
These are widely used conversion tactics but force customers to buy on your timeline not theirs.
We often focus on persuasion tactics, but instead consider focusing on creating successful customers.
17. Your Email List is a Fast Moving River
Don't throw them in head first! 🤣
Fast moving rivers have entry points that are safe and fun to hop in at.
You can curate your entry points to your email list.
Unless you are reporting news or other time sensitive information it almost never makes sense to sort things in chronological order as the default entry point to your email list or web content in general.
Curate serial content as entry points, "Learn X in 10 weeks"
Curate and design an evergreen sequence that those bits of serial content flow into.
Allow your customers to flow in and out of the serial content and evergreen sequence when they need or want to.
Curate an intentional learning experience that helps WHO achieve WHAT.
18. Back your hard pitches with soft pitches
Your launches are hard pitches. A sequence of events that leads to the hard sell. BUY NOW.
There's always a next step.
A CTA that will help your customer get from where they are today to a step closer to the WHAT they are hoping for tomorrow.
Unless your in the middle of a hard sell pitch, sprinkle around the soft pitches. Use them as PSes or as CTAs on your website. These are events, serial content, other products, etc that might be relevant to WHO working on WHAT.
Maybe it's a survey question to better align WHO and WHAT.
It's always something, so figure it out and show it.
19. Ask people to reply to your emails
This is great for gathering voice-of-customer data, improves email deliverability by showing that your emails often have interaction and you're not a filthy spammer, and most importantly solidify your actual IRL relationships with your customers.
The replies and conversations can be an ongoing machine for creating useful content. Turn questions into blog posts, new processes, serial email content, value nuggets, goodies, etc
20. Free Yourself from the Content Hamster Wheel
Once you've really dialed in a repeatable process to take WHO to WHAT, it often makes sense to create an automated fly-wheel sales process.
Customers are flowing through the nurturing river of your email list, learning more, gaining value, experiencing visible progress towards the WHAT.
They see an offer and click.
This moves them into a pitch which we deliver to them over time.
We take a pause at the end of the pitch to check if they interacted with it at all. If they did, lets close the sale, if not let's extend a bridge to build the relationship before we send the hard sell.
Customers aren't concerned with WHEN you created the process to get to WHAT, they only care about getting to WHAT.
Audience growth and sales will both be positively affected when you move from one-to-many (broadcast sent today, live launch, general admission) to one-to-one (THIS delivered to WHO about WHAT they care about)
I wrote about some of the mechanics of creating an evergreen sales funnel automation in ConvertKit in this post.