Your CAC is Climbing Because You're Ignoring Retention

AI helps scale messaging. Humans help deepen connection. You need both in order to build speed and quality. Using AI to spot performance trends and suggest fixes. This is something that we love AI for right now. The future is AI-supported humans creating messages that scale and still feel personal. That's very much how we believe we're seeing the best brands and their behavior in this market here today.

Help your new buyer succeed with what they just purchased. If they don't use the product, they can't come back. It's simple as that. Teach them how to use the product. Give them tips and tricks on how to utilize it. Teach them about something that's tangential And correlated and related to the product. People love learning about things like that.

Hey, what's up everybody? All right, today I've got a very special podcast for you. So Chase and I, we just went in front of almost 1,000 people and we did a conversation with the Omnisend team about a practical framework on profitable email and SMS in 2026. So listen, this is a really Great watch. So if you're listening to this on like Spotify or Apple Music, you might not be able to catch the slides. We also have downloadables, and there's a link. There's a worksheet that we're giving out at the end. We've got all the links in the show notes below as well. But with that being said, we hope you enjoy.

From the open to the click, they're the masters of the flow. Just watch your list grow and your leads turn to go. Did we retain you so far, or do we have to extend it? If you want results, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it.

Let's jump into Retention Redefined, a practical framework for profitable email and SMS in 2026. This is going to be an exciting 8-step framework based around everything we've learned from the data that we've received from Omnisend over the past couple years working together to all the information that we've gathered working with brands, consulting for different brands and companies. And so we've all put it packaged into a nice little framework here that we think you'll enjoy. We even have a downloadable worksheet that we'll give you later on. And in the middle of this thing, if you're paying attention, we've actually got Q&A, or I guess pop trivia that's going to be occurring where you'll be able to win actual prizes throughout this little presentation. So let's go ahead. If you're ready, you're locked in, take notes if you need to. Well, again, we'll get you this presentation and you'll have a downloader as well too. At the end. However, let's get right to it. So just to kick this thing off, I will kick off with myself and introduce myself. My name is Jimmy Kim. For those that don't know who I am, I've been in digital marketing and email marketing for the past 17 years. I've been on the brand side, I've been on the SaaS side, and I've been on the agency side. So I've been doing a little bit of all 3 formats of what you might be listening to this in the room here as well too. On my free time, other things that I do, I have— I'm a podcast host. For those that don't know, Chase Diamond and I have a podcast called Send It, where we talk everything about email and SMS all day, every day for hours on end. We're also doing live in-person event called Commerce Roundtable. This happens twice a year in Austin and in San Diego this year, but this is a live event that we host about 1,000 people a year. So if you're interested in meeting us, hanging out with us, and also coming to a very focused event, go check us out at Commerce Roundtable. There's a couple logos and we'll let Chase go ahead and introduce himself.

All right. Hello everyone. My name's Chase. You know, most of my experience comes from being a partner at Structured where we've driven, you know, $200 million in email revenue for clients. I'm a huge self-proclaimed email marketing nerd and frankly, just really excited to get into the playbook we have for you today. today for you guys.

And Chase obviously has been in e-commerce since 2016. So we're excited here today to jump right into this presentation. So let's go ahead and start and just talk about retention marketing because I always like to level set, right? I know that many of you guys in this room are probably experts or, you know, know what retention marketing is, but we always like to level set and make sure that we're talking from the same framework and mindset together. So if you're reading this, you already know the truth. First, Acquisition is getting harder, right? This is the truth right now. This is something that people are talking about. Paid media is becoming more unpredictable and the CACs or the customer acquisition costs keep climbing. Those are all true that are happening right now. And the biggest thing that I see in the market is attribution continues to feel like guesswork most days, not just some days. Now, this is what's interesting. However, there are brands with strong retention systems that aren't spiraling, that aren't feeling these effects. In fact, they're scaling it. And doing it profitably. And that's what we're really focused on here today.

So on this next one, um, I kind of want to level set on like what retention actually is. And it's kind of helpful to start by what it, what it isn't. So, um, retention at this point in stage is not a nice to have, right? Um, and with that, it's not a single flow. I think a lot of people are like, oh, I've got a single automation. Let's call it a day. Um, and then also too, I think people are so obsessed with campaigns and I hate to break it to you, but a single campaign, you know, a group of campaigns, that's not going to magically fix all of your problems. Um, the right way to think about retention is as a system. It's knowing when to use email versus SMS and both. There's still a lot of people that are not using them together. Um, and it's really focused on sending messages based on where someone's at in their specific unique journey. And that's going to be different than where other people are at in their journey. And I think like the, the main point that I want to get across is really shifting your mindset from just sending more campaigns, more campaigns, more campaigns to sending slightly fewer campaigns, but better and smarter campaigns. And that's really what we're focused on today is how do you build this system that's going to allow you to drive revenue in a more predictable way without having just to sling endless number of campaigns?

With that being said, let's jump into this framework and let's jump into the 8 steps in 2026. That you should be focused on, and then we'll give you a 90-day playbook on how to execute this thing. Okay. So the retention mind shift, let's start here because I think this is something that everybody should be thinking about. The shift is happening right now, right? We've, we've thought about the whole idea of an email marketer, an SMS marketer, a lifecycle marketer. We've talked about a lot of things, but what's really boiling into 2026 that we're seeing is the shift into really a retention mindset focus. So it no longer is thinking about, we need to send another campaign. The modern retention thinking really comes down to where is the customer in their journey and how do we move them one step further?

Okay.

I'm going to repeat that one more time because I think this is really important to think about. The modern retention thinking is where is the customer in their journey and how do we move them forward one step at a time? It's no longer about a batch and blast system. It's really about creating a good experience, an authentic experience for humans, and more than ever with the data and information that they're giving you today. So that mind shift continues to shift where the goals of modern retention are shifting right now. The things that people are thinking about how to measure their actual retention within the system is not just the attributable number that's on your dashboard and your ESP. It really is an actual goal-setting property. So number one, your number one goal is to reduce the time of first purchase, right? That's obvious, right? When you have a popup, Right? And they put their email address to opt in for whatever coupon or free gift or guide or whatever they might be giving you. Your goal is to get them to make that first purchase as soon as possible. Then your number 2 goal, and this is the profit center for most businesses, is to increase the repeat purchase rate, to get a person to make that second purchase more often, right? So you have 100 people and you have 30 people making a second purchase. You're trying to get that to 35, for example. And so forth. You also want to improve the average order value because it's not just about making more purchases, it's also about making people buy more. So your goal is not to just take them and get them to repeat purchase, it's also to take them and make more money off of it. And then of course, the biggest thing that I know a lot of brands are talking about today, and it should be in the back of your head, is about lifetime value. This is what does your customer value over a lifetime of their span with your company going to be. Look, There's always a beginning and an exit for every customer in a lifecycle. That's natural, right? They no longer need your product, your service, whatever it might be eventually. But during that time that they're with you, you want to maximize that. So each of these steps kind of takes you through that kind of principle that you think about.

Cool.

So on this next part, right, let's talk about kind of like the modern kind of updated customer journey. And really here, this is going to be the foundation that everything else is really built on. So focusing on this and This is probably one of my favorite slides just visually, but I'd say like what happens here is most brands focus on the first 3 stages as you're going to see, right? And stage 1 is awareness. So get them aware. Number 2 is get them interested. And then number 3 is get them to buy it. Then from there, for whatever reason, they just wing it, right? They put a lot of effort into acquisition and getting someone to convert. And then from there, there's no game plan. Where like this map that you're kind of looking at and you're going to see, this shows you the entire full journey. And I know it might seem like overkill, but really this is super important. Everything after first purchase is where brands have no plan. So, you know, I'm going to walk through this really quickly. So from the top, awareness, it basically is, I know you exist, right? So they're on your list, but they have never made a purchase. And your goal at this awareness phase Is to educate them and build trust. That's the most important thing to be able to kind of have them extend across the timeline. And then the next bucket here is interested. So people are thinking, okay, now that I know a little bit about the company and I have some trust, I'm a little bit interested in this. You know what you guys sell? It may or may not be relevant to me, but I'm paying attention. And now you need to show them why you're the right choice. So differentiating between yourself and everyone else, et cetera. And then this is the bucket, right? The first purchase bucket that I think most people get, right? Where people are like, all right, I feel confident enough to at least try it. So people are going to take a chance here. And again, this is where most brands stop thinking about the customer journey, which is a huge mistake. So in terms of the next step, onboarding is basically help me succeed. So here is where they actually need to utilize and leverage and use what they purchased. If they don't take full advantage of the product or maybe even the service that they bought, the likelihood of them coming back is very, very, very low. And then this next part is a second purchase trigger. So essentially, right, if we get them to try it and the experience was good, they start thinking, okay, this is going to be potentially worth repeating, assuming that the product is something you buy more than once. And this is really the most important stage in my mind. You want to get them to this stage as fast and as quick as possible. And then you have a customer, right? If you don't get them to the second purchase phase, you just have a one-time buyer. And that's going to be really, really hard to scale your business is if you can't convert people into second, third, fourth, fifth-time purchases. Right. And then with that, like, how do you actually do that? You have to do that by building habits and emotional buy-in, right? You have to allow people to connect in a way to your product again, or service. That allows them to remember a positive experience. And now they're not going to hopefully think about alternatives here, right? You're going to become their default product, their default coffee, their default supplement, whatever that might be. And then the last stage is really kind of the stage that is like the holy grail of advocacy where you feel so profound and moved and excited about a product that you now want other people to know. You're telling your friends, you're telling your family, you're leaving glowing reviews, you're posting about it on social. And essentially, right, like this is the stage in which your customers are doing your marketing for you. Um, and I guess the question, and you know, maybe you can answer if you want, but really this is rhetorical, um, is do you have these flows mapped out right for each of these stages? Um, and if you don't, right, that's the gap. And that's kind of the job of today is to go fill those gaps because this is how you're gonna win. That was a great breakdown, Chase.

And just to add to that, you know, I think the biggest key takeaway people should be listening to here is if you look at that first line, those first 3, that's your buyer. And then you turn that onboarding to that second purchase is your customer. And your goal as a retention marketer is to build customers, not just buyers, right? And that's really something that's really important as we think about this modern customer journey.

Hey, it's Chase. Got 30 quick seconds? We built something specifically for you. Jimmy and I together have over 20 years of combined experience in email marketing, and we finally put everything together in one place, and it's called Ecom Email Certified. I know it's fancy, but it's going to be great whether you're brand new or running campaigns for 7, 8, 9-figure brands. It covers it all— deliverability, AI, copywriting, design, strategy, SMS, literally everything. Has over 175 total modules totaling 25+ hours of content. Even has quizzes, a community, and you're gonna get a real certification. It's way better than college, right? Don't tell your professor that, but it is. And we've designed it to take you from beginner to certified expert. We're talking about the kind of marketer who actually moves the needle and drives real revenue. Check it out at ecomemailcertified.com. And now back to the pod.

I hope everyone enjoyed that little fun break. Thanks for participating. We've got more coming up down the road here. But all right, so number 1, we talked about the mindset shifts. Number 2, we talked about the customer journey. Now we're going to talk about segmentation now because we're going to dive a little bit deeper into this because phase 3 of the 8 steps is segmentation that actually matters in 2026. So let's talk about how segmentation should mature over time. This is probably the best way that I think about this chart, and I'm going to kind of walk you through from the top to the bottom here and really walk you through how this doc thinks about, right? So the basic is simple, right? Everybody is doing this right now— engaged versus unengaged, right? More relevance, obviously, people who are engaged. That's the most basics of segmentation. If you're doing that today, you're doing segmentation, you're using the module. Otherwise, you're just probably batching and blasting, which means you're selecting all and making a send. So number 1 is basic, engaged versus unengaged, which outputs more relevance. Number 2, you're thinking about behavioral. This is when people browse, add it to cart, repurchase. These are what we call triggered messages. These are pretty standard things that people are doing. This is what most businesses will run on. So number 1 and number 2, you should have a checkmark for already today. If you don't, Let's get started there, right? Number 3 is the customer type. This is when you start thinking about your customer and start focusing on the journey of a personalized lifecycle. Did they make once a purchase? Did they make it twice? Did they jump into a subscription? Did they purchase 17 times, right? All of these are different customer types that you're generating. You don't want to have too many of them, but you want to have a couple of them available on your segments that you're building. Then you get into the predictive layer, and this is where a lot of people are starting to figure out that they need to be tapping into. 4 and 5 are probably the biggest things that we can talk about here today. So predictive, this is the magical keyword. You know, it's a keyword and a buzzword that's been happening, but the reality is it's pretty straightforward and simple. It's replenishment timing, churn models, and category preferences. So let's break those down real quick. Replenishment timing is simple. You're looking at how long does it take for a customer to make your second purchase on average. So if you have 100 customers, that 30 of them make a purchase in the next 30 days, What was the average time in those 30 days? That's your timing, right? You're starting to narrow it down with data. Then you got churn modeling. Churn modeling shows kind of the same thing. If I have 100 people come into the top of the funnel today, how many people do I have after month 1, after month 2, after month 3, and how long and fast does this diminish? This gives you an idea of where to predict when the most purchases happen. And then of course category preferences again happen through the things that you're collecting on the data. What did they buy? What did they browse? What did they add to cart? Those start to show you the category preferences of the usual, right, user. And that ultimately delivers a messaging that a client anticipates, right? And then number 5, level 5 is when you start using zero-party data. This comes in way too early for many people. Zero-party data is only useful if you can nail the other levels of segmentation before you get to that place where you can layer in that information, which is going to be dynamic and personalized and information that the user is giving you, quiz values, results, tests, quizzes, whatever that you do in order to get those persons to engage with you, right? This is where high personalization comes into place. But if you can layer these different things, you can only, you can only layer these things together in order to tailor your message together. Often if you aren't layering things together like this that I'm talking about with segmentation, you probably don't have the right tone and voice to the audience that you have. You have a list that you're emailing, you don't have an audience that is listening. And I think that is the biggest key to this message of phase 3.

Cool. Let's talk now about kind of channel pairing, right? So I think a lot of people have a big opportunity here. And I think a lot of brands leave money on the table by not pairing, you know, these well together. So in terms of like email and SMS, like, I think the problem is that a lot of people treat these as the exact same channel. And frankly, they're, they're not right. Each channel has a job and they can work together to help complete that job, but they also, you know, work independently because they're not the same. So the way I think about email, email is really like your workhorse. So when you think about like visuals and design and kind of longer form storytelling, education, uh, trust building, right? Email is great at that because you can be a lot more kind of in-depth and you have a lot more context. than you could in an SMS, just due to obviously the short-form nature. So that's email. SMS is really great for urgency, right? It's really great for removing friction. It's really great for trying to get people to transact. Essentially, it's like moments where you wanna have like a real conversation, not just focusing on marketing and more conversational and more kind of like moment in time. Urgency, do it now type thing. And with that, right, there's also moments when you want to use both together. So abandoned carts is a great one. Launches is another great one. When you launch a product, launching on SMS, on email, kind of going back and forth, that's super important. Giving even like VIP early access to people on your SMS list. Those are the people that really want to hear from you, you know, potentially doing some subscription onboarding, but really like the high-intent moments where you wanna hit both channels, that's when it makes the most sense. When you have a big sale, when you've got a big launch, when you wanna just maximize the impact. And really the key here is like SMS should never feel like the email version. It really should feel more like a human version. Again, obviously your email should feel human as well, but the quick test that we always talk about and think about is essentially like, Go read your last SMS message or your last couple SMS messages. Does it sound like a text from a friend or does it sound like a marketing email with fewer words? And if it's the latter one, the marketing email with fewer words, you know, your unsubscribe rate's gonna probably be pretty high and gonna continue to increase. So really think about that and really work on that.

All right. With that, let's go to phase 5. This is when AI starts to show up, the messaging framework, right? This is what's going to be really important. A lot of people are expecting it to replace, but in our humble opinion of what we've seen, it's only accelerating those who use human integration well to be able to accelerate AI. AI is not doing it for you, but it can help you do it faster. And that's the framework we're going to talk about as phase 5 here. Once you've nailed the understanding of who your customer is with, uh, you know, understanding what retention is, what the customer journey is, what segmentation looks like, how you're merging the channels together. And now we get into the messaging framework. All right, so let's talk about it. AI helps scale messaging, right? Humans help deepen connection. You need both in order to build speed and quality. The best retention strategies in 2026 are not about replacing the marketer, about giving the marketer leverage. It's kind of what I kind of framed work here. So let's talk about this real quick. Think about your AI as this: your draft generator, your personal data analyst, your segmentation assistant, your timing delivery optimizer, your idea starter when creativity hits the wall. If you look at what it is, it really becomes almost like a, a junior marketer that is working with you that knows a little bit of everything and has high accuracy around the things that you're feeding it and giving it information. And if you start thinking about it this way, What you ultimately think about as the human touch, and you'll see how this all comes together, is one, you think about the emotional clarity, right? Humans can think about the current world economics, the things that are happening around them, how people are evolving, how the generation that they're talking to reacts to that information. They're the relationship builder. How do they really understand the difference of human emotional relationship versus a robot, which is going to give you something on historical values, right? Humor and tone. That's something that's really hard to nail. That's probably one of the hardest things and how most people know that things are made by AI is the humor and tone is not able to be relatable to what they've seen in the past or one that is relating to the audience because that is the key to all of this, right? That also increases brand memory, right? If you create that humor and tone and that relationship and that emotional clarity, all you're going to do is ultimately build brand memory and all of it lands down to real conversation layer, right? Having a human touch and bringing those together You can almost see how this happens, right? The draft generator will help you think about things on how to position, and the emotional clarity of the human touch takes the second part of that layer and adds more emotion to the actual conversation. A personal data analyst is great. They're going to give you the data, but we all know data doesn't tell the full story. The relationship builder— sometimes you're doing things away from the data on purpose. This is a perfect example of why. This doesn't merge together. Same thing with segmentation, you know, having humor and tone, right? All of these things work absolutely together. Some of the strongest use cases that we see right now in the market is using AI to spot performance trends and suggest fixes. This is something that we love AI for right now. As a retention marketer, I'm able to feed it data, feed it information, and say, what do you see on the trends? And sometimes those minor blips in the data don't show much, but at the data, when they're merging multiple points and data points together, It really is able to suggest those fixes, right? You let AI create test variants so you can learn faster, right? Look, we should be testing, we should be doing different things, we should be split testing within our businesses, everything you do, right? If you're not doing that right now, you're just not taking advantage of the tools that you have available to you. But where people get stuck often is how do I create test variations? Well, the great news with AI is that it's going to help you create a million of them as soon as you can, as fast as you can. And be able to turn those out really quickly, right? You also want to predict the best, best, best send times based on your customer behavior, not guesswork. This is a great use case that I've started to see is where they're starting to understand when are my customers interacting? Can I feed it data from my other networks, my social, my website, and all these different places and start predicting down to when I should send that email into the user? And of course there's personalizing the messages at scale, right? This is no doubt something that people are using more and more today. Something that people are trying to nail down, which is the personalized messaging at scale using the purchase data, tone signals, and lifecycle stages. Those start coming together a little bit faster with AI. And then of course, offloading repetitive tasks. This is probably the best use case of AI right now. A lot of people call these agents or different things that they can build, but if you have repetitive tasks where you can focus on the hierarchy of strategy, creativity, and storytelling, and you can have your AI take care of the rest ultimately, or take care of the tasks that are repeated over and over again, this is where you can ultimately win. That's phase 5. That leads us to phase 6. Oh, and remember, the future isn't AI-free humans, it's AI-supported humans creating messages that scale and still feel personal. That's very much how we believe we're seeing and seeing the best brands and their behavior in this market here today. Hey, it's Jimmy, and I've got 30 seconds to tell you something that will change how you get inspired on your very next marketing campaign. You know when you're screenshotting those emails in your inbox and Slack and pasting them here? You saw it on Twitter, trying to remember what brand did that killer Black Friday sequence. Well, guess what? Inbox.ai just solved that. It's an AI-powered database with over a million real emails from the best DTC brands— Ridge, Fenty Skin, Casper— they're all in there. You can search by promotional type, journey stages, whatever you need. Get AI breakdowns of what worked and why, track your competitors, and even request brands that are not in there. No more hunting through screenshots or saved folders. Inbox.ai turns your inspiration into revenue. Check it out at inbox.ai, link in the show description.

Uh, this is a fun one. So when I think about this section, this is really the core of the, the whole system. And I think we went through a lot of great stuff today, but I think if you only remember one thing, it's probably this section. 'Cause I think a lot of people have a ton of room and opportunity to improve. Specifically on their automations or their flows. So kind of these 8 flows on the, on the next slide. Let's see. Cool. So essentially, when we think about these, this is what makes up a functioning retention engine, right? As I mentioned in the beginning, if you have 1 or 2 flows, you know, you have 1 or 2 flows. That's not a retention engine. I think most people maybe have some of these, and most people probably don't have Enough. So I'm gonna walk you guys through kind of each one, starting with the welcome flow. I think this is pretty common, but I'm gonna go through it anyways. So this, this is really like your first impression with your subscribers that just joined your list. They're super excited. They're super engaged, right? If you are collecting SMS, here's a great opportunity to pair email and SMS together. But, but this is really gonna set the tone for your entire relationship with the subscriber. So you really want to make sure that this is on point. And it's something that you're constantly iterating, right? I think the best thing to do is like open yours and read it, right? Like if you've, if you haven't done this for more than 6 months, it's probably hurting you, right? And I would probably say that to be the case for all the flows, but this one especially. The next one is the conversion boost. So this is things like abandoned cart, you know, abandoned checkout, browse abandonment, et cetera. And these are really like what we call like money recovery flows. So this is a huge opportunity because people have some varying level of interest. Obviously at abandoned checkout, the interest is quite high. They're very close to buying. Um, and if your recovery rate for some of these is like sub 10%, then there's some work to do there. So that's, that's definitely a big focus. Then we move on to onboarding. So kind of talked about this a little bit earlier. This is where most people seem to stop for whatever reason. But the goal here is really to help your new buyers or your buyers, help them succeed with what they just purchased, right? So if they don't use the product, they can't come back. It's simple as that. So teach them how to use the product. You know, give them tips and tricks on how to utilize it. Teach them about something that's kind of tangential and correlated and related to the product. People love learning about things like that. We mentioned this one earlier as well, but the second purchase accelerator. Almost no one seems to build this from what we see, but essentially it's one of the most important flows you can have where customers who buy again within 30 days, they're going to be 3 times more likely to become repeat buyers. So if you don't have this, you know, you're hoping for a second purchase instead of engineering it. So again, this is everything that happens after that first purchase to build that trust, get them to use it, showing them testimonials and reviews. Giving them recommendations of other products, etc. And that lends itself to like the next one, which is the cross-sell. So you want people to expand kind of what they've purchased from you related to, you know, what you know about them. So if someone bought skincare, think about like what else might they need to, you know, benefit that skincare routine, or what other things might someone that bought skincare want? Don't make them figure it out themselves, or if you do kind of put it on them, give them some kind of quiz or some kind of a way to answer a few questions or even track a few of their clicks to try to suggest the most relevant product or products for them. Replenishment ones. So if you have something that's like a consumable or topical, essentially your product runs out. Skincare, haircare, supplements, food, drinks. This is a really great flow to set up. Where the really the key here is you're going to want to figure out the timing. You know, if it's a 30-day supply of vitamins, figuring out do you hit them on day 22, day 25, day 27, all of those days? What does that look like? The next one is the VIP and loyalty. But I know I'm going through this very quickly. You're going to get the recording. You're going to get the slides at the end. Don't worry. And if you have questions, we'll take questions at the end as well. But the VIP and loyalty, again, this is for the people That are spending the most amount of money with you. And those types of customers, they want to feel special. If you're treating someone that's bought 5 or 10 times from you the same as someone that's bought once from you, you're basically telling them that they're no different and they don't really matter. So you do want to treat one-time buyers, multi-time buyers, your VIP buyers, you know, differently. The next one is the win-back. So This is basically trying to bring back customers who've gone quiet. And the kind of the caveat here is if your win-back is one of your top-performing flows, that's probably a red flag. It means everything upstream that we just talked about is leaking. So again, you want win-back, you want it to convert, but it shouldn't be like your top 3 converting flows. And the last thing here is every single one of these flows needs to focus on kind of 5 primary things. Number 1 is a clear purpose. Number 2 is a trigger, right? So how does someone actually enter into this flow? Um, the, the persona-specific messaging. So you shouldn't have the exact same tone and voice for all of these. It should be specific and unique to whatever flow they're in, whatever stage they're at. A game plan for testing. So you need to be A/B testing. These are not set it and forget it. Otherwise they'll go stale. Um, and then the improvement metric. And we're gonna talk about some of the improvement metrics in a little bit.

All right. That brings us to phase 7, the metrics that matter in 2026. Let's talk about 2026 and what metrics that people are thinking about in their retention scorecard. I'll go ahead and go through a couple and Chase will go through a couple with us here too. So let's talk first about, we've talked about this before, repeat purchase rate, why it matters. And look, the reality of what a repeat purchase rate is, if you don't, as an email marketer or a retention marketer or whatever role you have that is working within the email side of it, if you're not really focused on this data point, the retention of repeat purchase rate, this should be brought up to the top. The main reason why acquisition is happening is to drive repeat purchase rate. You know, when I ran a brand, what was really always interesting about the metrics that people didn't understand, and I quickly understood as we went and started scaling our paid media, was As we started to increase, we've quickly learned that a one-time purchase is great, but getting them to make that second purchase is where the profit is made. And this is why it's really important. And the business understands that a retained customer on a repeat purchase drives profit. That is how you know retention is actually working. Otherwise, you're just a messaging delivery person, and that's not really helping the outcome of the business. It's really just delivering and creating the sales that A little bit quicker. But when you can actually show repeat purchase rate increasing due to your efforts, that's why it should be on a retention scorecard as a marketer, as an operator. Second thing that you should be thinking about is the time to second purchase. If, if Joe, Sue, and Ted purchased on day 1, let's just pretend today, and then Joe bought on day 10, Sue on day 14, and, uh, you know, uh, I forget the last name, uh, Joe Jr. on day 21. You're starting to measure the time of second purchase. And what this is going to help you do, not only is it going to allow you to be more predictive because you're going to know based on averages of your data, because I gave you 3 examples, but majority of them are going to start showing up in, hey, they opted into day 1, they're making a purchase by day 3, they're making a second purchase by day 28, right? Something like that's going to come up. And based on that data, it's going to give you an indicator of how you should approach your retention. Getting that time of second purchase reduced is a very strong predictor of your long-term retention. So you're going to use the data to drive the data down and drive that marker down. All right, Chase.

Awesome. So on this one, right? So essentially here, we're going to talk about like 2 metrics that most brands ignore. And it's really focused on like, I guess the first one is like active subscriber and kind of SMS list health. So if you think about your list right now, right, how many people have actually engaged in, let's call it the last 90 days? I think that is kind of really like what people should call their real list. You know, if you have a huge list, but no one engaged in the last 90 days, you don't have a huge list, right? You have a small list. You know, the rest of the people, you know, with a little bit of wiggle room, but the rest of the people outside that 90 days, It really is dead weight and it's gonna hurt your deliverability, right? I think too many people still are chasing like vanity metrics, like list size, where people really need to start focusing on kind of measuring their, their list health. Um, that's really the only thing that matters. Jimmy and I have done a podcast recently. I don't know if it's come live or not about like how some of the ISPs, so like Google, Yahoo, et cetera, are really focused on engagement and prioritizing your email. If you have high engagement at the top, um, it's almost like a social algorithm. It's kind of what's coming to email. So engagement is everything. And then the next part here is the LTV by cohort. So essentially, right, like thinking about like, are your customers that you acquired last quarter as valuable as customers from a year ago? And if you don't know, you're kind of just guessing whether it's actually improving or not, right? So you want to pull this report. It's going to basically give you kind of the, the truth of the matter about whether your system is working or not. And I think after this presentation, you're gonna have a lot to update. So maybe pull it before you update it and then pull this again, you know, in 3 or 6 months once you've updated the things we talked about today and you should see a noticeable difference.

Yeah.

LTV to cohort is one of my favorite metrics to look at, but some other ones that I really enjoy are AOV by channel. I think this is something that's becoming more important than ever because diversity of channel is bigger than ever in the world of direct-to-consumer and e-commerce back in 5 years ago when I asked a brand what do they use, they say Meta, right? Meta being Facebook, Facebook Ads, whatever you want to call. But now when you ask a brand what they want to use, they're using Facebook, AppLovin, Google, TikTok Shop, you know, they're using Amazon. They're using so many different places that you no longer can look at a single AOV point and look at that as a retention marketer and know that that's happening. So where TikTok may give you a $20 AOV, where Facebook might give you an $80 AOV, yet you're treating everyone the same. And that is going to help you balance campaigns and flows. This is where it gets really important. If you know you have a low AOV customer, stop showing them heavy, expensive products to make their second purchase on. It's going to be a challenge versus if you've got a low— a high AOV product and you're showing them cheap products, that may also not align. And that AOV by channel is so important. Average order value is going to help that balancing campaign. And then of course, this is a metric that people don't think enough about. And I like to call this the do they care signal. And I think this is really important. Unsubscribe percent. Look, naturally unsubscribes happen. There's nothing you can do about that. That is part of the game of unsubscribe, but you've got to be able to track that. Well, again, like Chase mentioned, we had a pod. We talked about the unsubscribe for a while in depth actually. And the idea behind trends and understanding that this is a common practice. There's a funnel on the top that's happening and a funnel that's happening on the bottom. These are people entering your lifecycle and people exiting the lifecycle. Unsubscribe is their way of saying, I no longer relate or want the product that you have. And there could be other reasons, you send too much, you do other things, but that's the minimal part. Those are all symptoms of an output of people who are no longer interested in your brand or different things. So unsubscribe percent is really something you should look at. It's a trend line. If you're seeing a spike, it means that your messaging or conversation or something along the line is no longer connecting with that audience. Hey, quick 60-second break to shout out our title sponsor, Omnisend. If you don't know them, Omnisend is an all-in-one email and SMS platform built specifically for e-commerce. They're trusted by over 155,000 merchants with a 4.8 rating star on Shopify's marketplace with over 2,800 100+ reviews. People love using them. Their support is incredible, responsive team, great help docs, and they actually show up when you need them. 3, look, everyone loves saving a buck. They've got great features and great pricing. Listen, I've heard this inside the community that someone actually dropped their bill by almost 50% and then included their SMS costs, which is absolutely wild. Another agency that we talked to shifted all his clients over when he discovered that he could and save them 30 to 60% off of their actual monthly bill. And taking that money now reinvesting into ads and that real money is going to come back into your pocket too because you're helping them out or, you know, whatever it might be. You know, with all this, I literally just helped Chase migrate his personal list to Omnisend not too long ago. It was super easy. They got team, they have an automated solution. It's really great. So if you're looking to scale your email and SMS game, check out omnisend.com/sendit. Tell 'em Chase and Jimmy sent you. Now back to your pod.

Okay. So, you know, we've covered a lot, right? And I'm sure people are having questions like, how do we implement this without getting overwhelmed? Um, because it is a lot, right? So I think like the best way to think about this is as like a 90-day plan and sprint. So on the, on the next slide, we kind of break down like really an actionable plan, I guess we'd call it. So looking at it in terms of like weeks, so that way over the next 90 days, you can kind of build this out. So, um, for weeks 1 through 4. I think the opportunity— I know Jimmy went into it— is the segmentation. Again, most people think they have segmentation. I think, not being mean, I think most people have sorting, right? They're not segmenting, they're just sorting with very basic things that are outdated. So go fix your segmentation. That's number one. Number 2, just given how impactful and important your welcome series is, like the welcome flow for non-buyers, you should go review it, review the data, and update it and start running A/B tests there because That is such an important flow, has high engagement, has high conversion, and it just sets the tone. So that's number one. Number 2. So for, for weeks 1 through 4, um, it's going to be a lot, right? To do that. We want to be reasonable. So that's it. Get the foundation right before we talk about scaling and building on top of it. Then from there, you're going to want to optimize your core flows. So we went through the 8 flows, the welcome being one of them. So that means you'll have 7 other kind of flows to work on, build out. Optimize, edit, et cetera. And then if you can, if you don't do SMS already, start adding SMS collection, adding it to the welcome series. And if you do do SMS, you know, add SMS pairing to your cart abandonment, your checkout abandonment, those types of things. And then also to like really begin to start measuring the flow performance properly, kind of mapping it out, understanding where you're at and having a plan and a sense of like where you want to get to that's reasonable. Then from there, kind of the last part, the 9 through 12 weeks is focusing on getting a bit more advanced. So focusing on collecting and building out as much as kind of zero-party, first-party personalization, building out and leveraging like more predictive analytics and predictive triggers, et cetera. And then when you get to this 90 days, kind of at the end of this sprint that you're going to do, you're going to want to measure 4 things that we kind of talked about already. Would be the time to the second purchase, right? The sooner you get to the better. I think the stat we told you was if you can do it within the first 30 days, it's 3 times more likely that someone's going to buy again. Um, basically active subscriber segments. So what people are actually opened and engaging emails within the 90 days. Um, how much revenue is coming from flows versus campaigns? And then what is the lifetime value, the LTV uplift? So if those numbers are all increasing in the right direction, then you know that you're building out the system properly. And then kind of some final thoughts. I kind of started with this. I'll end with this as well. Retention is a system, right? It's not a one-off email. It's not a single flow, etc. It's a system that's built on five primary things. Number one is value, and that's super important, right? You have to deliver value. Value could be a discount. Value could be education. Value could be. You know, whole hope, you know, giving people support. It could be giving people exclusive access. Like everyone finds values in different ways. And that's why it's so important that you mix up what you send. So people do find value. Number 2 is the timing. Really be testing timing. Omnisend has a great report. I don't remember the name of it, but they have a great report that shows you actually people's behaviors throughout different times where Certain times might surprise you where maybe at 6 PM at night or 8 PM at night, that's when people open and click and purchase emails, but everyone's sending emails at 8 AM or 9 AM. The next part is the relevance. So again, this is kind of the holy grail is the timing and the relevance. So the email needs to be specific to a person. You can't treat someone that's bought one time versus 10 times the exact same. The relationship. So again, the more that you can humanize your brand, the more that you can speak to them, your subscribers, your customers, not at them, the better. And then the last part is progression, right? The goal is to take them from a subscriber to a one-time buyer to a repeat customer. And with that, every flow you build, every message you send, every campaign, right? It doesn't matter what you're doing. Everything needs to tie back to at least one of those 5. And if it doesn't, you know, cut it. And if you could pick just one thing from today, Um, just one, you know, do it, build it out and fix it. So it doesn't matter which of the one things you do, but your homework this week is to go build out one of the things we talked about and fix it.

All right. Welcome back. We hope you enjoyed that little presentation that we did here, uh, in front of a live audience. And we even did a little bit of Q&A and all that fun stuff there. But anyways, uh, important things. Number one, if you want that worksheet we talked about down below, I also will link the presentation link down below too, just so that you have it. Again, if If you listen to this, there's a lot of valuable display and visibility in the things that we're talking about. Plus that worksheet, make sure you grab that thing because it's going to allow you to kind of follow along and watch our framework. This is the framework and something that we do in a live element when we're doing with training with people. We're excited to bring this out to the market for absolutely free that you can get. There's nothing to buy. You can download it. We hope to— we hope you enjoy. And oh yeah, P.S., we've got that brand new vault. You should check that out.

From the open to the click, they're the masters of the flow. Just watch your list grow and your leads turn to go. Did we retain you so far, or do we have to extend it? If you want results, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it.