In this article, I’ll be walking you through one of my proven email strategies that upsells your customers and grows your customer lifetime value (C-LTV)—completely on autopilot…

It’s something you set up once, and let run continuously. And it continues to take your current customers… identify when to email them next to get them to buy from you again…Ultimately letting you see higher C-LTV, and higher margins, with minimal effort on your part. This is one of the highest-leverage activities you can do in your business, so read through this article carefully. 

Also, you may qualify to have this entire process set up for you to save you time and give you peace of mind, knowing your Customer’s Lifetime Value (C-LTV) will be continually increasing—without you having to step in and do things yourself.

Let’s jump into how to do this (using a proven process that already works)… 

What is Customer journey mapping? 

Customer journey mapping is a strategic process to visualize and understand the various touchpoints a customer experiences as they move through different stages of engagement with a business, product, or service. 

When done effectively, it helps you see things from the customer’s perspective, allowing you to create a tailored experience that aligns with their needs and desires at each stage.

In essence, whenever we want to upsell customers, we start with customer journey mapping, because that is the thinking process that allows us to establish a good upsell framework.

It’s what allows us to understand our customer on a more “macro” level. Then dictate, what EXACTLY we have to do to make the next sale—knowing our customer in and out, allows us to do this in a way that CONVERTS, instead of something that…doesn’t convert lol. 

Let’s peel back a layer of the onion.

Step 1: Macro-Level Customer Journey Mapping

Before we get into the upsell, we first need to establish the customer journey from a broad perspective. Every customer goes through phases, and mapping these out gives us clarity on how they interact with our business at each stage.

Key Phases of the Customer Journey:

1. Awareness: The customer first learns about your brand or product.
2. Consideration: They start comparing options, exploring solutions to their problem.
3. Decision: They make a purchase.
4. Onboarding: They begin using the product or service and getting value.
5. Engagement/Retention: They continue interacting with the product and the brand, exploring additional value.
6. Advocacy: They become loyal, recommending your product to others.

It’s important to note, this is the same process when UPSELLING, too…

Even when a person knows you have a higher “tier” in your product stack or value chain, they still are looking at other options. 

(Eg. you have an agency coaching program that takes people from 7-figures to 8-figures.)

(eg. you have a business coaching program that takes people from 7 to 8-figures. Then 8-figures to 9-figures. The people scaling past multi-7 figures, approaching 8, are still looking at other options that will take from 8 to 9-figs.)

Step 2: Identify Key Moments in the Journey

Now, when it comes to upselling…

We need to understand the emotional and psychological state of the customer as they progress through each stage. This helps us know where to introduce an upsell without being disruptive.

1. In the Awareness and Consideration Stages:
   • The customer is problem-aware and is seeking solutions.
   • This is NOT the time for an upsell. The focus here is on addressing their pain points and helping them understand how your initial offering solves their problem.
2. In the Decision and Onboarding Stages:
   • They’ve made the first purchase.
   • Emotion State: They’re likely feeling excited but might also be cautious, wanting to ensure they made the right decision. They’re in a discovery phase, starting to explore the full value of what they bought.
   • Key Moment: This is still not the time for an upsell, but it’s crucial for creating trust and making sure they feel successful with their purchase.
3. In the Engagement/Retention Stage:
   • They’ve used the product or service for some time and are starting to experience its benefits, as well as any limitations or challenges.
   • Emotion State: They’re feeling comfortable but could be starting to notice gaps that the current product doesn’t fill. This is where an upsell can fit, based on pain or opportunity that naturally arises in the product experience.
   • Key Moment: This is where we introduce the upsell. It’s framed not as a sales pitch, but as the next logical step in their journey. The customer is primed to see how the new offering solves their emerging challenges or enhances their experience.

Step 3: Pinpoint the Customer’s Emotional and Psychological State

When you reach the Engagement/Retention stage, the customer has already invested in the product or service. They’re familiar with your brand, and they trust you to some degree. However, they’re now at a point where they might:

• Encounter a limitation: They see where the initial product helps, but they realize there’s more they need to fulfill their biggest desires in life. 
• Desire further success: They’ve had success with your product, and now they’re open to the idea of expanding their capabilities. Buying more stuff to build on this success. Or addressing some of the “gaps” they’re missing. To make them feel more complete.

This is where having bundled products if you’re an ecom store helps. And, having a “next step” for courses, coaching programs and more become your secret sauce for retention and higher C-LTV…

Here’s the most important part though, that will drastically improve the conversions for your upsell emails:

The customer may not be aware they have a NEW problem—this is crucial to understand. They’ve experienced some success with their first purchase, but now, we need to gently reveal the next hurdle that’s holding them back. Here’s how we approach it:

Emotional State:

• Complacency or Plateau: They’ve experienced an initial win but now may feel like they’re stuck, plateauing, or not getting the full results they imagined. Emotionally, they could be starting to doubt whether they’re fully equipped to achieve the ultimate success they want.
• Uncertainty or Hidden Frustration: They might not even realize that a deeper issue is causing their frustration, but they feel like something’s missing. They could be hitting a hidden roadblock that’s limiting their progress without them fully knowing it yet.

Psychological State:

• Unaware of the New Problem: They don’t necessarily know they have a new issue yet. They’ve achieved success with the first purchase, but something else is now holding them back—and they’re not entirely conscious of it.
• The Shift from Satisfaction to Discomfort: While they’re satisfied with their initial purchase, they could also feel discomfort—something isn’t fully aligning with their desired outcome. This is where we need to introduce the problem that they’re now facing, even if they didn’t realize it at first.

Step 4: Create the Upsell as a Natural Step

Now that we’ve identified the exact moment where the upsell fits, the next part is to introduce it in a way that feels like the logical next step in the customer’s journey. 

This is about presenting the upsell not as an additional product, but as the next natural step toward achieving the bigger goals they have in mind.

And the way we do this, depending on the audience’s awareness level…

Is by exposing a NEW problem to them, and or a NEW opportunity to achieve better results.

Typically, we expose the new problem and intensify it, as that’s what drives the motivation to purchase again. 

But we do so carefully to avoid creating buyer’s remorse. 

We want the customer to feel congratulated and good about themselves for their previous purchase. But also feel pain and desire to address this next challenge…

And the only way we can really do these things together is by exposing the problem and agitating it in a strategic way. 

Here’s what that looks like…

Deeply Exposing the New Problem:

• Reveal the Roadblock: The key here is to introduce a new pain point that naturally arises because of the success they’ve had with the initial purchase. This pain point needs to feel like a bottleneck that’s preventing them from achieving the next level of success.
• Make it Personal: Use language that helps them connect emotionally to the problem. Rather than saying, “Get better results,” we frame it as: 
• “As you start to get more results with product XYZ, one thing you might notice is challenge] is beginning to show up.”
• Then → 
• “And if that’s the case, and you’re still facing [insert specific challenge], maybe that’s why you’re not getting to the next level as quickly as you wanted.”
  • For example, they might not realize that without addressing this new issue, their current success will stall or even diminish over time.

Basically, the person has plateaued, and the only way they will break past this plateau is by addressing this NEW challenge/opportunity we’ve revealed to them.

And we have to do this in a more gentle way. By congratulating them first, so we can avoid potential buyer’s remorse. 

But then, we create pain and desire, as that’s what will motivate them to purchase again. 

And it lets us do it in an empathetic way, that shows a deep concern for their struggles, and a strong belief in their potential… And giving them the solution to achieve what they want. 

As you can see, we’re exposing a new problem that arises as a result of their success, and positioning the upsell as a solution that helps them break past the plateau.

By mapping out the customer journey, we know exactly where they are and can introduce the upsell at the right moment.

Here’s a step by step way.

How to Position the Upsell in the Customer Journey

1. Acknowledge Their Success (Avoid Buyer’s Remorse)
   • Customer Journey Context: They are in the Engagement/Retention phase, having experienced some success with their initial purchase.
   • Goal: Celebrate their progress and reinforce that they’ve made the right decision, eliminating any doubt and ensuring they feel good about their purchase.
   • Example:
     “You’ve already made incredible progress with [product]. Your results so far show that you’ve taken the right first step toward [desired outcome], and you’re well on your way.”
2. Reveal the Roadblock (Deeply Expose the New Problem)
   • Customer Journey Context: As they continue on their journey, they’re starting to experience limitations in what the initial product can do.
   • Goal: Introduce the new problem that naturally arises because of their success. This bottleneck needs to feel like it’s preventing them from reaching the next level, but it should be introduced gently to avoid overwhelming them.
   • Example:
     “As you’re starting to get more results with [product], one thing you might notice is that [specific challenge] is beginning to show up. It’s something many people at your level face once they’ve made this much progress.”
3. Make the Problem Personal
   • Customer Journey Context: They are moving into the phase where they desire further success and are noticing gaps.
   • Goal: Use language that helps them connect emotionally to the problem. Make them realize this problem is holding them back, but do it in an empathetic way that aligns with their experience.
   • Example:
     “And if that’s the case, and you’re still facing [specific challenge], maybe that’s why you’re not getting to the next level as quickly as you wanted. Without addressing this issue, your current success could start to stall or even diminish over time.”
4. Position the Upsell as the Solution to Unlock a New Opportunity
   • Customer Journey Context: They’ve now hit a plateau, which makes this the right moment to position the upsell as a solution that will help them reach the next level.
   • Goal: Present the upsell as the exact solution to help them overcome the new problem and break through the plateau. It’s framed as the next step they need to take to continue their momentum.
   • Example:
     “That’s why we created [upsell product]. It’s specifically designed to help you tackle [new challenge] and unlock the next level of [desired outcome]. By addressing this now, you’ll ensure your progress continues without any roadblocks.”
5. Create Desire and Drive Action (Through Pain and Opportunity)
   • Customer Journey Context: They’re aware of the limitations and are ready to move forward but need motivation.
   • Goal: Without overwhelming them, create both the desire to improve and the pain of staying stuck where they are. You want them to feel motivated to take action to avoid missing out on their next big win.
   • Example:
     “This is your opportunity to break past the plateau and continue achieving the results you’ve been working toward. By addressing [new challenge], you’ll be able to get [desired outcome] faster and smoother.”
6. Focus on Benefits, Not the Product
   • Customer Journey Context: They are still in the decision-making phase, where they are ready to invest but need a clear understanding of what they’ll achieve.
   • Goal: Focus on the benefits they’ll get by addressing this new challenge with the upsell, not the product features.
   • Example:
     “With [upsell product], you’ll gain [specific benefit 1], avoid [specific problem 2], and continue to build on the success you’ve already achieved.”
7. Timing Is Critical (But Keep It Subtle)
   • Customer Journey Context: They are in a critical moment of deciding whether to take the next step.
   • Goal: Emphasize that now is the perfect time to take this next step, but without pushing urgency too hard.
   • Example:
     “Now is the ideal time to act. You’ve already laid the foundation, and [upsell product] ensures you won’t lose momentum or get stuck.”

Summary of Step 4:

• Acknowledge their success, reinforcing their progress and avoiding buyer’s remorse.
• Expose the new problem that arises as a result of their current success, making it personal to them.
• Position the upsell as the solution to this new challenge, showing how it fits naturally within their customer journey.
• Focus on benefits, highlighting what they will achieve if they take the next step.
• Make sure the timing feels natural, offering the upsell at the point where they are most ready for it.

Can you see how customer journey mapping is what lets us create our upsell sequence here? 

Because that’s what allows us to…

Step 5: Deliver the Upsell Emails at the Right Time For Maximum Conversions

Look at this sample sequence below, then read my notes after. 

Email 1: Post-Purchase Confirmation – Congratulate them on their purchase and set expectations for what’s next.

Delay (30-180 days) – The exact time delay is based on when they’ve likely started using the product and experiencing results.

Email 2: Introducing the New Challenge (after the delay) – This is when we begin the upsell process. We start by congratulating them to reduce buyers remorse, while weaving in how…

“One thing you may start noticing is problem XYZ… If that’s been happening to you, that’s perfectly normal… that’s what tends to happen when you start succeeding with product X. It’s a good problem to have. It shows you’re doing well, and on the right path. Eventually, though, if you’re looking to [scale past 8-figs/see continued success] you have to start addressing problem X that prevents you from getting benefit Y. I have some resources I can send your way. So just be on the lookout. If you don’t want those resources you can click here and I won’t share anything else to help address problem X. You’ll still get my other emails, you just won’t see any future emails about solving problem X to get benefit Y. Talk soon.”

Email 3: Offer the Solution – After presenting the problem in Email 2, offer a resource or product that can help them solve the issue. Be direct, but still friendly and empathetic.

Give them the option to “opt out” of these emails.

Email 4: Highlight Success Stories – Share customer testimonials or examples of how others have overcome the same problem by using your upsell product. Build credibility and trust here.

Email 5: Reinforce the Benefits and Call to Action – This email could reinforce the benefits of your upsell product and include a clear, well-timed call to action. You want them to feel motivated to take the next step.

So, we have our first purchase email, right? That’s basically your post-purchase email. 

Then, we add a DELAY based on the customer journey mapping we did.

Eg… *Wait* 30 to 180-day delay etc. 

Here we wait until whenever the next email makes rational sense for us to begin making that next sale. So essentially, we reverse engineer, how long does it take for people to get our product and start using it.

For example, if they buy a course and need to get a certification or do 2000 hours of training first… well that might take some time.

So by doing your customer journey mapping in the beginning, you can see when to do each email. 

If I need to Trade for 30 days first, until the market starts kicking my butt, well then, give me 30 days until you start getting me to buy your next trading program or whatever. 

Ya see?

By giving the right offer to the right person at the right time, you can see higher conversions without ever having to do a strong promotion to your customers. 

It’s all about knowing them deeply, what their journey looks like for a customer, which all begins with the customer journey mapping process. 

>> Click here and book your call if you would like to have this exact strategy installed in your business—completely done-for-you.