Hi! We're Jason and Caroline, a husband and wife creative team taking you behind-the-scenes of building our new business from scratch. Poke around and watch us figure it out as we go!

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Marketing Part 3: Our Ongoing Marketing Strategy & Customizing Our Email Sequences

Marketing Part 3: Our Ongoing Marketing Strategy & Customizing Our Email Sequences


"Marketing" is one of those terms used so broadly it's sometimes hard to know what someone is referring to when they use it. In our minds marketing means: how are your customers going to find you?

We may be building Wandering Aimfully from the ground up, but we’re not starting from scratch in the audience/marketing department. 

We’re in the unique position of having quite a bit of built-in traffic coming from our existing brand sites (JasonDoesStuff and Made Vibrant bring in ~50,000 monthly visitors). We’ve spent the past four years writing consistently, building an email audience of about 15,000 subscribers and, as you read in last week’s post, this has led to quite a bit of revenue for us. 

Given the fact that we know this marketing strategy works (high quality content -> high quality newsletter(s) -> email launches -> sales) and that we enjoy it, we’re not planning to deviate too much from this. 

Content Marketing vs. Paid Advertising

In fact, we want to take this organic content strategy as far as it can go, and we only want to use paid advertising as a last resort. We don't have anything against a paid advertising strategy, it’s just that we honestly don’t want to have to manage it, nor do we want to have to rely on paying X dollars a month in order to get paying customers. Operating on that model might work for now (and for other folks), but what happens when the ad prices go up or they stop being effective? We would feel more comfortable knowing that our word-of-mouth and content strategy works and any paid ads we choose to run on top of that in the future will be gravy on top. 

Marketing starts with understanding the journey of a customer

So, "selling memberships to our subscribers through email" is a pretty vague marketing strategy. How can we break it down into something more specific and tactical? How can we trace the journey of a customer from their first interaction with us to their eventual purchase?

To map our the customer journey, let’s start at the end with our ultimate goal: 

The goal is for someone to purchase a Wandering Aimfully Membership. Now, how are they most likely to get to the payment page and hit "join?" 

As we mentioned in yesterday’s post, we plan to do open and closed launch windows every month to our email list, with the goal being to take on only 30 new members every month. These launch windows will last one week, from Monday morning to the following Monday evening (Monday being the same day our email newsletter goes out.) 

Our most engaged audience is our email newsletter list, and potential customers are most likely to find out about the monthly launches from that newsletter. So, (again, working backwards here) we want to develop an ongoing email sequence that can accomplish three things:

  1. Provide ongoing value to our list. (Whether they're a Wandering Aimfully member or not, this is always a priority for us. We always want to lead with value whether a person is in a position to buy a membership or not.)
  2. Get new subscribers immediately excited about what we do, what resources we can offer, and how we teach.
  3. Convert engaged email subscribers to buyers of our membership.

We plan to accomplish these three goals using email customization and automation...

Using customization and automation in our email sequences to give subscribers the best experience possible

Setting up our email “sifters”

There's a lot of jargon in the online business world, but certain words make us cringe (JVs, funnel, tripwire, funnels, ew, ew, ew), so we like building our own language that's fun and different. Instead of using the word "funnel" to describe how someone could become a potential customer, we're using the word sifter. (Plus, a sifter makes us think of powdered sugar on funnel cake, and that's a deliciously unhealthy childhood memory!) 

The basic journey of a customer

To accomplish the three goals we laid out above, it helps to start with the basic journey of a customer from their first touchpoint with us to our end goal: a purchase of our membership. It looks something like this:

Our basic email journey to purchasing

Our basic email journey to purchasing

[person lands on our website/article] -> [signs up to our newsletter] -> [gets Monday weekly newsletter] -> [when membership window opens, gets launch email] -> [signs up for membership]

Once we see this basic flow laid out, there are a few questions that immediately come to mind:

  • Will one email “announcing” the membership be enough for a potential customer to join? (Spoiler alert: No.)
  • What if someone doesn’t want to join right now or is already a member… won’t that be annoying to get a sales email (or set of sales emails) about the memberships once a month if they're on our newsletter? 
  • And is there a way to deliver value to a new email subscriber up front that gets them excited to join, even if the membership window is “closed?”

These are the three caveats that we want to address in our email “sifter.”

It’s important for us to note, if you’re starting out and using a similar strategy, this doesn’t mean you have to go down a rabbit hole of email automation right away. Having a simple (un-automated) newsletter strategy can most certainly work. We know because we used it for many years. 

But, in our minds, if you know how to improve the experience for someone in your audience and you have the resources to pull it off, it's time to automate.

Our plan is to use the email automation tools within our email provider Drip to customize our basic customer journey to something more specific to each person's wants and needs.  

Three important pieces to our customization strategy 

1. A lead magnet/onboarding email sequence: When someone first subscribes to your email list, this is when they're most engaged and excited about your content. They enjoyed your stuff enough that they took action and signed up for your list, so why not use that as an opportunity to give them what they want: more valuable content from you. We'll be setting up a four-day email sequence that walks a subscriber through a framework we created called "Working To Live" which gives actionable advice on how to reverse engineer your ideal business based on the life you want. This workshop went over really well with our subscribers before, so we'll be breaking it up into four days of short actionable lessons and videos. In our minds, not only does this give new subscribers immense value when they're most excited about us, BUT it also primes them for the type of resources they can expect inside the Wandering Aimfully membership.

Basic email journey with Working To Live onboarding added

Basic email journey with Working To Live onboarding added

2. A week-long sales sequence ONLY for new subscribers: As we mentioned above, one email on the Monday that our launch window opens won't likely be enough to sell our membership. We'll want multiple opportunities to remind someone of what's included in the membership and how it can help them. That's why we'll write a 6-email sales sequence during the launch window, but only for new subscribers (aka subscribers that have been on our list for less than a month and haven't been through a sales window already.) This way we'll be able to do an adequate sales sequence for those interested in the membership, but we won't bother our regular subscribers with a repetitive sales sequence every month. 

Email journey with onboarding and sales sequence added

Email journey with onboarding and sales sequence added

3. Customizable content based on membership status: The final fun thing we can do with our email customization is to only show certain email content to certain subscribers. We can hide content within the body of our emails to subscribers that are already members of Wandering Aimfully. So, on the Monday that our sales window opens, here are the three different versions of the email subscribers will get:

  1. New subscribers, not members yet - These subscribers haven't been through our sales sequence yet, so instead of our regular newsletter on the Monday our sales window opens, they'll get a longer "launch" email announcing that memberships are open.
  2. Existing subscribers, not members yet - They'll receive our normal Monday newsletter, with a smaller callout at the bottom saying memberships are now open. 
  3. Existing or new subscribers, already members - They'll receive our Monday newsletter but thanks to Drip tags, their email won't mention the Wandering Aimfully membership or try to sell anything.

This is where customization and automation does come in handy. We can customize the journey of a subscriber based on their activity, their interest level in the Wandering Aimfully Membership, AND how long they’ve been a subscriber. 

It's also important to note here: We know we aren't building the perfect "sifter" right out of the gates. But, we're picking a direction we feel good about AND that we can execute. We'll let this strategy run its course for a few months, see what the data tells us, then tweak and change things based on what we've learned. 

The power of segmenting, tagging, and email automations

If you haven't heard, we use the email provider Drip. We don't recommend Drip to everyone, in fact, Jason wrote a comparison article about which email provider we think is best for different situations. We use and love Drip because we can do some pretty advanced stuff to ensure our email subscribers get a good experience (read: don't get sales emails every single month.)

Subscriber Tagging

One of the first things we do in Drip is to create tags that help us know more about a person's activity with our emails. A couple tags we'll be using:

  • Interested In: WAIM Membership - This tag will be applied any time someone clicks a buy/sales link in our emails.
  • Opted Out: WAIM Sales Emails - This tag will be applied any time someone clicks an opt-out link that we provide in our sales emails (different than unsubscribes, which removes people from our email list completely)
  • Customer Segment: WAIM Member - This tag will be applied any time someone purchased the Wandering Aimfully Membership.

These tags are incredibly helpful, because when we're setting up our sales emails or our sales automation workflows, we can segment people out who shouldn't get sold to (specifically people tagged with Opted Out and Customer Segment).

Automation Workflows

We're not gonna sugarcoat it (bringing the funnel cake back around!), email automations can get REALLY tricky. I spent months last summer learning how to build them and I'd be lying if I said they were easy to concept/build. 

A few initial automation workflow sketches

A few initial automation workflow sketches

The reason we want to use automation workflows and not just schedule a few broadcast sales emails each month, is that we can automatically pull people out of a group of sales emails if they don't meet certain qualifications: 

  1. We're only going to send our monthly sales pitch to a subscriber every 3 months (unless they opt out completely, then they'll never see it again).
  2. We're going to send a tailored sales pitch to VERY engaged new subscribers who open all four emails in the initial onboarding workflow we'll be sending. These people should NOT get our standard monthly sales pitch if they subscribed close to the end of the month.
  3. Subscribers who are already paying members should never see a sales pitch. (Even on our website, which we'll talk about later on down the road.)
A snapshot of one of the many automation workflows we'll be creating

A snapshot of one of the many automation workflows we'll be creating

And, just to give you an idea of how complex this can all get, here's a rough idea of the actions and triggers within Drip that are required to actually execute on all the things mentioned above (warning - 🤓🚨):

  • User registers through our form (gets email to confirm subscription)
  • Automation Rule triggered, applies tag “Registered: WAIM Newsletter”
  • “Registered: WAIM Newsletter” triggers “Onboarding Shell” workflow to begin:
    • User starts “WAIM - Working To Live” onboarding workflow
      • Applies “Started Workflow: Working To Live”
      • Immediately: Sends WTL Email #1
      • Next day at 7:00am - Email #2
      • Next day at 7:00am - Email #3
      • Next day at 7:00am - Email #4
      • Next day at 7:00am - updates final email score; applies “Completed Workflow: Working To Live” tag
    • User exits “WAIM - Working To Live” workflow
    • If WTL score is equal to 4 (all emails were opened), triggers “WAIM - Back-door pitch” workflow
      • Applies “Started Workflow: WAIM Back-door Pitch”
      • Applies “Pitching - WAIM” tag
      • Sends “Back Door Pitch #1”
      • 2 days later at 11:00 am - Sends “Back Door Pitch #2”
      • 2 days later at 11:00 am - Sends “Back Door Pitch #3”
      • Event triggered: Completed WAIM back-door pitch
      • If purchased at any time or finishes workflow, applies: “Completed Workflow: WAIM back-door pitch” and removes from pitch sequence
    • If score is less than 4, event triggered: “Forced completed: WAIM onboarding shell”
    • If purchased at any point, applies “Purchased: WAM Membership” and moves on OR forced completes, which:
      • Applies “WAIM Newsletter - Active”
      • Applies “WAIM - New Subscriber”

Weekly Monday newsletteres are sent through Broadcasts to segment including tag "WAIM - Newsletter Active"

Sunday before pitch, we add Saved "New Subscriber" Segment to workflow “WAIM - Launch Window Pitch”

If “WAIM - New Subscriber” …

  • Apply “Pitching - WAIM” tag
  • Mon 7am - Sales Email #1
  • Tue 7am - Sales Email #2
  • Thu 7am - Sales Email #3
  • Sat 7am - Sales Email #4
  • Monday morning - Sales Email #5
  • Monday morning - Sales Email #6

And then we test ALL the things! It's pretty complex, but we'll do an even more thorough write-up later on.

Going back through our sifters, we'll put ourselves in the shoes of our subscribers and customers. We'll sign up for our lead magnets. We'll add certain tags and then start automation workflows for our own emails. We'll review our subscribers in Drip to make sure they're getting the right tags, emails, etc. 

Unpopular opinion: Not every subscriber has to become a customer

While we are setting up our email sifters to give our subscribers to opportunity to become a paying customer, it's not the end-all-be-all for us. 

We need to keep our lights on and run a profitable business, but we aren't interested in trying to squeeze a dollar out of every subscriber/website visitor. That's why we do things like offer opt-out links in sales emails, and are doing a 3-month rotating sales cycle. 

In fact, if/when we hit our goal of 300 paying Wandering Aimfully customers, we'll turn off our sales automations completely. Who does that?? This crazy couple, that's who!

The Challenges of Building Something Won't Get Us Down

The Challenges of Building Something Won't Get Us Down

Marketing Part 2: Our open and closed launch strategy to sell Wandering Aimfully Memberships

Marketing Part 2: Our open and closed launch strategy to sell Wandering Aimfully Memberships