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Email Growth Marketer

The Ultimate Email Marketing Upsell Sequence

Most companies post-purchase sequences lose them more customers than they retain (or upsell).

Most companies post-purchase sequences lose them more customers than they retain (or upsell).

Their customer base is shrinking…

And they’re always having to rely on expensive acquisition channels & chase new customers just to maintain their current revenue levels…

They can never consistently scale.

Sound familiar?

Luckily, there’s a unique post-purchase sequence that quickly grows your revenue, retains customers longer, and increases AOV.

I call it the Elongated Post-Purchase Flow.

The Elongated Post Purchase Flow

Basically, you want to combine both a post-purchase flow and an upsell flow together.

Essentially, you STACK an upsell flow on top of your post-purchase flow.

There’s 2 elements:

  1. Post-Purchase Process (generates reviews, onboards/trains, gives FAQs/education, drives consumption, ensures they use the product and get value from it)
  2. Upsell Process (belief shifting, educating/exposing the “next” problem you’ve created for them, boosting AOV, customer journey mapping)

But here’s why most people mess this up:

There’s a reason why we structure these 2 flows together.

You see, after the 1st purchase, there’s generally gonna be people ready to buy a 2nd time.

So you want to be able to scoop those people up right away.

Otherwise, you’ll be losing out on a lot of extra revenue you could be getting. Right?

At the same time…

There’s gonna be people who AREN’T ready to buy a 2nd time yet. Usually, they aren’t ready to buy again because they need more selling/belief shifting.

This is where the upsell sequence comes into play (after they go through the post-purchase flow)…

The post purchase flow’s role

You see, post purchase flows make offers that convert those ready to buy TODAY.

But they don’t do all the belief shifting, desire creating, and other psychology techniques needed to convert “not ready” buyers into ready to “buy something more expensive buyers.”

That’s why taking people through a regular post-purchase flow FIRST… and then BOLTING on an upsell sequence after works so much better.

If you wait to upsell, you’ll miss out on those who are ready now/today – plus your chance to get reviews, and accomplish everything else you want to do in your post-purchase flow.

To convert those people who aren’t ready yet, you must ask: what’s the natural next step in their customer journey, and how do you accelerate it with email? This is where buyer LTV growth happens on autopilot.

Now let me walk you through the process step by step.

The Post-Purchase Flow (Phase 1)

The post-purchase flow has a few jobs:

  1. Generate reviews.
  2. Onboard and train the customer.
  3. Give them FAQs and education.
  4. Drive consumption.
  5. Make sure they actually use the product and get value from it.

Here’s the structure.

Email 1A: Order Confirmation (Same Day)

This is a transactional email, but it’s so underutilized.

Give them their order details. Then subtly show other products and drive traffic back to the site.

Matt Hommel, marketing expert, discussing customer LTV growth strategies.
Matt Hommel, marketing expert, discussing customer LTV growth strategies.
yH5BAEAAAAALAAAAAABAAEAAAIBRAA7 The Ultimate Email Marketing Upsell Sequence
Upsell Order Confirmation Email The Ultimate Email Marketing Upsell Sequence

If it’s a repeat purchase (a customer’s 2nd purchase), push for referrals instead of the upsell.

Email 1B: Celebratory Email (Same Day)

This one is fun. Celebratory. Confetti goes off…

Matt Hommel speaking at a DTC brand growth event, engaging with an audience.
Matt Hommel speaking at a DTC brand growth event, engaging with an audience.

Basically, tell them what to expect…

How the shipping process is going to work…

How they can keep track of their order (their tracking number)…

And anything else important for your order process.

Then…

Give them a customer-only discount with a CTA.

The key here is framing the discount delivery like a favor, not a sale.

Email 2: Anticipation Builder (2 Days Later)

Here we do an unboxing video… or push to social channels to cross-promote and leverage other traffic sources.

(Example below)

The video builds anticipation and excitement…

It resells them on the product before it arrives.

I call this tremendous onboarding.

Because the sale hasn’t closed yet, until the customer actually gets the product, uses it, and achieves what they wanted to with it.

As you’ll see… this is the beginning of their journey…

You have to take them through this EXACT process if you want to create lifelong customers…

Each one of these emails achieves a specific goal in the customer lifecycle…

And you HAVE to send them in this exact order I’m showing you…

To increase your customer retention rate, and increase your customer lifetime value.

Matt Hommel demonstrating customer lifetime value strategies for DTC brands.
Matt Hommel demonstrating customer lifetime value strategies for DTC brands.

On top of the unboxing video or push to social channels…

You also give another customer-only discount with a CTA here too.

Unboxing Cacao Bliss Box & Boosting Customer LTV with Email Marketing.
Unboxing Cacao Bliss Box & Boosting Customer LTV with Email Marketing.

(If you don’t have a video, you can use blogs, social videos/UGC, or link to social to cross promote.)

Email marketing strategy boosting customer lifetime value for DTC brands.
Email marketing strategy boosting customer lifetime value for DTC brands.

Email 3: Shipping Updates (2-3 Days Later)

Sync shipping updates with your delivery system. Klaviyo and Shopify native features do this well…

yH5BAEAAAAALAAAAAABAAEAAAIBRAA7 The Ultimate Email Marketing Upsell Sequence
Your order has arrived email The Ultimate Email Marketing Upsell Sequence

Depending on shipping timeline, you might want content here:

Blog articles, success stories from other people who bought…

Send them to pages and content with the highest revenue-per-page-view.

Rebuild excitement. Give encouragement.

(You don’t wanna be that person who only talks to the customer when they buy and then again when you ask for a review later.)

Email 4: How to Use Your Product / FAQ (2 Days Later)

Your title or opening line should acknowledge the exact thing they purchased. And illustrate benefits and education specifically for that product.

Email flow increases customer lifetime value for DTC brands.
Email flow increases customer lifetime value for DTC brands.

Include the actual takeaways…

Link to helpful pieces of info:

  • Blogs
  • Video tutorials on YouTube (how to use the product)
  • Customer videos/UGC (customers showing how THEY use the product)

Ask yourself:

Does this help them use the product and get value from it?

Is it simple? Engaging?

Does it NOT sound like a research paper?

I like to show I know what they purchased, and I’m here to help them get the best results possible with that purchase.

(Nobody wants buyers remorse)

Hand holding a perfume bottle demonstrating effective perfume storage tips.
Hand holding a perfume bottle demonstrating effective perfume storage tips.

Email 5: How to Use Your Product / FAQ Again (7+ Days Later, Optional)

More helpful content.

More links to blogs, video tutorials, UGC.

This one is optional depending on the complexity of the product…

Zapier Onboarding Email Example
Zapier Onboarding Email Example

Email 6: Review Request (30 Days Later)

Personalized at the name AND product level.

Make it easy to leave a review.

Incentivize them, or make it polarizing/funny.

You can use Okendo, Yotpo, or Stamped.io for this:

Customer review of Huron Shower Kit with 5-star rating and feedback.
Customer review of Huron Shower Kit with 5-star rating and feedback.

Advanced Tip: Based on their review, you can send them different offers.

Bonuses for 5-star reviews. Coupons based on not-great reviews. “Try this instead.” etc.

This is also where the upsell flow begins.

If they leave a positive review, that’s an incredible time to start the next phase of the sales process…

Email marketing strategy for increasing customer lifetime value.
Email marketing strategy for increasing customer lifetime value.

Customer Journey Mapping

Before you write a single upsell email, you must do customer journey mapping.

Document every interaction a customer has with your brand…

From discovering products on social media to post-purchase, unboxing, loyalty and advocacy.

Visual guide illustrating the customer lifecycle stages to boost DTC brand growth through email flows.

There are a few key elements here:

Touchpoints: Mapping out all interaction points. Paid social, organic social, website browsing, email marketing, checkout, upsells and loyalty.

Stages: Tracking the process through awareness, consideration, purchase, retention, and advocacy.

Emotions and Motivations: Understanding how a customer feels and what drives them at each stage from lead, 1st purchase, 2nd purchase, subscriptions, upsells/cross-sells, etc.

Goals: Identifying what the customer wants to achieve throughout their journey with you. For example, if you’re a nutrition brand, it’s their health journey (gain muscle, lose fat), or if you’re a fashion brand it could be their wardrobe, or it could be their financial journey if you’re a trading education business or selling other financial produces.

Here’s the process.

Step 1: Macro-Level Customer Journey Mapping

Every customer goes through phases. Mapping these out gives you clarity on how they interact with your business at each stage.

  • Awareness. They first learn about your brand or product.
  • Consideration. They start comparing options, exploring solutions to their problem.
  • Decision. They make a purchase.
  • Onboarding. They begin using the product and getting value from it.
  • Engagement/Retention. They continue using the product and reading your emails, while exploring other forms of value.
  • Advocacy. They become loyal, recommending your product to others, placing fat orders with huge AOV.

Step 2: Identify Key Moments in the Journey

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 WHEN to introduce upsells without being pushy.

Ask yourself:

Why did they buy the front-end product?
What do they want to accomplish next?
Where do they get stuck?
Why do customers get stuck with this product?
What products help them get unstuck?
What beliefs need to shift for those products to feel like an obvious next step?

In the Decision and Onboarding stages, they’ve made the first purchase. They’re usually feeling motivated. But they’re also still feeling a bit skeptical.

They don’t trust us or the product entirely yet… They want the product to work. But if something weird happens, they’ll be quick to blame us or feel like it’s always their fault. (On the other hand, someone who has bought the product from us many times and gotten good results with it, if they have a bad experience one time, they’ll assume it’s other factors without ending the relationship.)

This is NOT the time for an upsell…

It’s a crucial window to create trust and make sure they feel successful with their purchase.

(This is why we do onboarding in the post-purchase flow.)

Analyzing customer journey stages to increase LTV and sales.
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Step 3: Identify NEW Challenges and Frustrations

When you reach the Engagement/Retention stage, the customer has already invested in the product or service. They’re familiar with your brand, they trust you to some degree.

And most importantly…

They’ve used the product and are starting to experience its benefits.

However, they might be starting to experience NEW challenges….

They could be starting to notice gaps that the current product doesn’t fill.

Just like in video games… every new level unlocks a new monster you have to face.

They solved 1 problem, and by doing so they’ve unlocked a NEW problem…

Eg. “I’m jacked but now my clothes don’t fit.”

or, “I’m getting more leads now, but I can’t close any of them!”

This is where an upsell is appropriate, based on a pain point or opportunity that arises naturally in the product experience.

This is where we begin the upsell process…

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.

In order to upsell them, we need to make them aware of that problem, and then make them actually feel pain. Or desire for improvement. Without those emotions, they won’t feel compelled to buy the upsell.

You’ll have to map out the different points of your customer’s lifecycle based on your product and business model.

For example, if you sell airplane trainings… do they get their pilots license and fly around for a few months until they need more advanced pilot training?

Or if you’re selling bedding or interior design… Does your customer leave their mattress on the floor for the first 30 days after moving into a new apartment? (Peak male experience).

Understand your buyer, when they typically do things allows you to time the upsell at the right timing.

Eg – 30 days after they purchase, 6 months after getting a certification (for a renewal.)

Step 4: Create the Upsell as a Natural Next 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 their bigger goals they have in mind.

The way we do this 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.

The only way we can do these things together is by exposing the problem and agitating it in a strategic way…

That looks like:

  1. Congratulate them on their purchase
  2. Reassure them they made the right decision
  3. Acknowledge their success to avoid buyer’s remorse
  4. Expose the new problem that arises as a result of fixing their first problem
  5. Position your upsell as the solution to this new problem
  6. Focus on benefits, what pain they’ll remove, how they’ll get better, faster results
  7. Explain how your new solution works
  8. Give them a no-brainer, one-time offer (this is their only chance)
  9. Give them a guarantee
  10. CTA

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

This is where customer journey mapping pays off…

Because it’s what allows us to time the upsell perfectly.

Example:

Email 1: Post-Purchase Confirmation – Congratulate them on their purchase and set expectations for what’s next. (This is the same post-purchase from earlier. 

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

Email 7: Introducing the New Challenge (after the delay) – This is when we begin the upsell process.

This brings us to the actual upsell emails…

The Upsell Flow (Phase 2)

This is where buyer LTV growth happens on autopilot.

And where you skyrocket your EPS (Earnings per Subscriber).

But before you write a single email, remember when I said to ask yourself:

  • Why did they buy the front-end product?
  • What do they want to accomplish next?
  • Where do they get stuck?
  • Why do customers get stuck with this product?
  • What products help them get unstuck?
  • What beliefs need to shift for those products to feel like an obvious next step?

…you need to answer those 6 questions first!

At a minimum, you need to know:

  • What upsell product you’ll use
  • Why it’s a logical next step for them
  • Why it will get them better, faster results
  • What new pain/challenges they have now (and how to press on that wound!)
  • What they need to THINK, FEEL, BELIEVE to buy
  • What objections or other factors would cause them not to buy

If they feel like they can continue their life without ever purchasing the upsell product… and they’ll have ZERO consequences for doing… it’s a weak offer.

Now, let me show you what successful email upsell offers look like.

Email 7: Belief Shifting (After 30-180 Day Delay)

The delay is based on your customer lifecycle and the customer journey mapping we did earlier.

Here’s how to structure your 1st upsell email (email #7, because we did 6 post-purchase emails already):

  • Congratulate them, reassure them them they’re on the right track to reduce buyers remorse
  • Acknowledge the success they’ve already have (if they left a review or got a certification, etc.)
  • Then, shift beliefs and get them to start thinking about the next phase of their lifecycle…
    • What goals or milestones they want to hit.
    • What problems they might be facing, and that you’re here to help them navigate the journey
  • Gently expose the new problem, and make a logical connection to why this problem is new and pressing and deserves attention, and only exists because they just solved their first problem
  • Tell them what to expect next, you’ll be sharing resources to help them with their problem
    • Encouraging tone, because you’re on this journey with them and will be with them every step of the way throughout their entire lifecycle… there’s nothing you both can’t achieve together!

Link with your review software, too!

If they leave a positive review, that’s an incredible time to upsell and begin the next phase of the sales process.

Examples:

Drone industry growth and pilot training to boost your drone career opportunities.
Drone industry growth and pilot training to boost your drone career opportunities.
Endurance BCAA supplement for muscle recovery, endurance, and growth. Boost your workout results wit.
Endurance BCAA supplement for muscle recovery, endurance, and growth. Boost your workout results wit.

Email 8: Belief Shifting + More Direct Offer

After presenting the problem in email 7, use another belief shifting email while introducing the upsell offer or a resource that can help them solve their issue.

Send them to your highest revenue-per-page-view content.

“This pairs perfectly with…”

Drone pilot training for advanced skills and certification.
Drone pilot training for advanced skills and certification.

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Matt Hommel promoting gut health with a focus on customer LTV growth.

Matt Hommel shares insights on growing a DTC brand’s customer lifetime value through effective email flows.

Email 9: Testimonials + Urgency

More belief shifting… Creating urgency…

Share customer testimonials or examples of how others have overcome the same problem by using your upsell product.

Gauge interest in supplementary offers too, by including them in the footer section of the email…

They help you segment people based on what they click and how many times they click.

Then, you can see what they likely want the most and serve more content that will convince them to buy that thing.

Drone safety and training courses to improve skills and knowledge for drone pilots.
Drone safety and training courses to improve skills and knowledge for drone pilots.
Enzyme supporting body functions in smoothies and snacks with pineapple and citrus images.
Enzyme supporting body functions in smoothies and snacks with pineapple and citrus images.

Emails 10-12+: Direct Offers

This is where you get more aggressive.

  • FREE [thing they bought] with purchase
  • Just checking in… (on the “free thing they bought”)
  • Running low? Here’s a code to restock. Or introduce subscribe and save.
  • ESPECIALLY if they gave a 5-star review

Leverage behavioral analytics here.

Lifetimely (Shopify plugin) and Klaviyo analytics are your best friends.

Special Offer Example

Email marketing strategy to boost DTC brand customer lifetime value.
Email marketing strategy to boost DTC brand customer lifetime value.

So…

How Do You Find the Right Upsell Offers?

Product Sales Report For Email Marketing Campaigns
Analyzify

Pull product sales reports. Look at your best selling products/categories. 

What are some popular slept on products?

Look at what’s already selling organically. Is there anything that’s selling well organically, that hasn’t been promoted to the email list yet?

Offer exclusive offers to buyers that non-buyers can’t access —> repeat the cycle.

That’s your lowest-hanging fruit.

Then use Lifetimely and your predictive analytics to identify cross-purchase patterns and buy cycles. Just like I did with the whey protein and BCAA supplement.

Look at what customers are already buying together on their own. Then build a flow that accelerates that behavior.

You can run this like quiz funnels too. With segmented emails based on people’s interests or what they buy.

In fact, I built a quiz funnel for a 9-figure client that got a $48 rev per recipient. How I’d know what to sell? I pulled product sales reports to identify our best selling products for each category.

People would go through and tell me what they wanted more of… I’d then offer a 3 email promo “for the next 72 hours, here’s an exclusive discount… then add related products in the footer. Segment these by product categories and make sure to use the top sellers in those categories that already show demand!

Get creative! Find bundles with other products as your “upsell” to boost AOV. 

Either find a bigger supply (60 day supply vs 30 day), or “this gets better results when combined with this” 

The Best Upsell Offers For Email Marketing

At a minimum, sometimes the easiest LTV driver is just more of the same thing they bought (typically best upsell #1 in DTC cold traffic funnels and often beats done-for-you, faster results/better results.)

To do this, identify the supply and typical buy cycle/renewal cycle of a product.

Then send an automated “re-stock” campaign.

Something like:

“Top off your supply… wanna make sure you don’t run out, so you can continue getting these great results. The more consistent you are the even better your results get. I opened a 20% discount to make it easier for you [Stock up and save].”

If you’re using Klaviyo, you can link this based on the Sku— so you can get granular— if a person buys a 30 day supply, you can use that logic in the flow to time the upsell/resell perfectly (especially with predictive analytics and customer journey mapping tools)

If someone bought a 30-day supply of something, and your data shows the average reorder happens at day 45, build a flow that hits them at day 40 with a restock reminder.

You don’t always need a new product to upsell. Sometimes you just need to make it stupidly easy for them to buy again. And then use a little pain/benefit language to push them over the edge.

More-of-the-same is good for physical products (like supplements)

Done-for-you and faster results are good for informational products (books, investment subscriptions and stock picks).

The highest converting upsells are either:

  • Done-for-you results
  • Faster results
  • More-of-the-same

Example:

1st purchase: How to fix your bad credit

2nd purchase/upsell: An automated program that files the forms to fix your bad credit for you

Summary

Start with customer journey mapping…

  1. Identify the buying cycle customers go through (timing, products, etc.)
  2. Use lifetimely, predictive analytics, to identify unique product journeys and congruent upsell opportunities.
  3. Identify the timing and buy cycles to time your upsell flows perfectly.
  4. Use conditional logic in flows by SKU for razor sharp targeting and messaging. 

Then, setup your post purchase flow:

  • Order confirmation
  • Congratulations “Confetti” email
  • FAQ/onboarding 
  • Get reviews/testimonials 

The goal of your post-purchase flow is to get them to USE the product and get results.

Then… based on your customer journey mapping process and upsell paths you’ve identified…

Start the belief shifting process, and introducing the new problem.

You want them to be well aware of their new problem, feel pain and desire…

And then, shift their beliefs…

Get them to realize your upsell is the ONLY way their situation will ever get better.  

Goal: Boost AOV. Make them go from placing $47 orders to placing $97+ orders and up. Higher AOV generally is more margins and practically guarantees higher LTV. If you can double someone’s AOV, you’ll often double their lifetime value. 

Someone who spends more money with you in a single transaction buys more over time. And it’s a lot easier to do that than increase the frequency of their orders, especially when they have to wait for shipping more often. You reduce the time to value. So many other obvious benefits of increasing AOV with upsell flows like this. 

Use bundles, etc. or just sell more of the same thing and a bigger supply (60 capsules instead of 30).

Conclusion

Most companies post-purchase sequences don’t retain or upsell their customers.

Forcing them to rely on expensive acquisition channels as the only option just to maintain their current revenue level.

The Elongated Post-Purchase Flow is a unique post-purchase flow that quickly grows your revenue, retains customers for longer, and increases your AOV.

When you combine a strategic post-purchase flow with a well-timed upsell sequence – and use customer journey mapping to nail the timing – you turn every single buyer into a revenue multiplier.

The framework is simple:

Phase 1 gets them to use the product, trust you, and feel good about their purchase.

Phase 2 exposes the next problem, shifts their beliefs, and positions your upsell as the obvious next step.

If you take one thing from this post, let it be this:

Stop treating your post-purchase flow and your upsell strategy as two separate things. Stack them together. Time them perfectly.

Then let the data tell you when your customer is ready to buy again… so you can make the easiest upsell of your life. Or if you just want someone who does this for a living to implement everything for you like the push of a button, fill out the form on this page to see if you qualify, and reserve your free consult.

About the author:

Matt Hommel

Matt Hommel is a multi 8-figure email and growth marketer. He’s the publisher and editorial director for the popular email and growth marketing newsletter known as Email Growth Marketer, and he’s founded H&C Media, a leading marketing firm now scaling today’s most sought after education and finance brands.
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