How to do winback campaigns in ecommerce

You don't lead with money at all. You lead with that reconnection.

A lapsed prospect, they never proved anything. They raised their hand, they gave you email address or a phone number, and lots of people do that to join those lists for discounts, but they never really might have even had intent to buy.

Someone signs up, maybe they browse, add to cart, whatever that trigger was, that's going to be the peak for that person. That's the hottest they will ever be. And then from that moment and forward, their intent actually dwindles, it decays.

You can have good customers, the ones that love you, they start landing in spam or promotions or AI's filtering it out because you're Your overall engagement looks terrible, so you're literally sacrificing your best subscriber deliverability to keep email emailing people who will never ultimately buy.

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.

What is up everyone? Welcome back to Send It, where we discuss anything and everything retention marketing, specifically in email and SMS marketing in e-commerce. My name is Jimmy Kim and I'm here with my co-host.

Chase Diamond.

All right, Chase. So today we're talking about win-backs because this is where I want to talk about things that I think most people don't think about. So here's how I'm going to set this up, right? When somebody says win-back, they say it like it's one thing. It's either this like one flow strategy, one strategy. We miss you, and with a coupon of some sort slapped on it, and that's it. Like that's generally what we hear about when people think that about winbacks, and I think that's the biggest single reason why winbacks, in my opinion, are broken at most brands because winback isn't one thing; it's actually two completely different problems wearing a similar name. There's a customer here. Let me explain. So there's a customer who bought from you at one point, spent dollars with you, and they eventually drifted all away. And then it was the prospect who joined your list from your free discount. They may have showed some interest, browsed some pages, abandoned a cart, but then they never pulled the trigger before going cold. To me, that's not the same person. They're not even the same value and they don't get the same message because you can't use the same level of aggression or even, or the same ending. And ultimately when you run them through the same flow, you lose both because neither of the messages are for them. What are your thoughts?

Yeah, I think the stakes also here are lopsided as well, which is really kind of the part that I'd like to dig into. You know, if you lose a customer you already earned, that's really painful and that can be quite expensive. Whereas if you lose a prospect who never bought, in my mind, that's a different kind of loss. And some of those prospects, I think you actually should be trying to lose faster, not slower.

Yeah, that's exactly right. So today we're going to split the whole win-back idea into 2 real buckets, a customer win-back and a prospecting win-back. And that's what this episode's going So we'll cover why the customer lapse hurts so much and how it actually approaches each one of those differently and why prospect win-back can be fast, like you said, and aggressive, and why, you know, those who don't respond need to get dumped into like a hygiene pool instead of dragging out your whole program down, which I think is a big problem in this market. So let's get into it. So let's start by defining those 2 buckets clearly because the whole episode hangs on this. I want everyone listening to make sure you really understand here.

So— Yeah.

Buyer bucket 1, we're going to call, is the customer win-back. This is someone who has actually purchased from you. That means they pulled dollars and cents out of their pocket, a credit card swipe, received your product maybe once, maybe 10 times, but they've crossed that line, that threshold. They gave you that money, they got the product, and then they went quiet. They stopped opening any of your emails or clicking, and they stopped buying, and they stopped engaging. That to me is a lapsed customer. Then you've got bucket number 2. That is the prospect. This is someone who's never bought. They joined your list through either like a popup or discount. They browse your site and they showed some level of interest. They might even have abandoned a cart, but they never converted. And now they're going cold because they're not responding to your messaging. That's a lapsed prospect. Though it's the same word, win back, these are 2 totally different situations that many marketers are treating exactly the same. And the reason it matters is that the value of what you're losing is wildly different between the 2.

Yeah. And with that, like, I think let me add some kind of weight on like what the customer lapse hurts, you know, and why it hurts so much more, because I don't think people actually think about this or feel this quite deeply enough. Essentially, like when a customer lapses, you're not losing a maybe, you're actually losing a proven known value asset for kind of a lack of better way to explain it. This is a person who's already answered the single hardest question in all of marketing. Is will you give this brand your money? And they said yes, which is this enormous kind of leap of faith, right? And you also have this data on them. You know what they bought, when, how much they spent, what they browsed, and you have some sort of relationship with them. And you already paid this customer acquisition cost to get them here in the first place. Now that cost is sunk whether they come back or not. So this lapsed customer is paid for. There's proven, there's this data-rich relationship that's now kind of slipping away from your fingertips, which is quite painful. This really big expensive hole and loss. And I think it does need more thought and care than most people do currently.

Yeah, you're exactly right. And I would say that if you think about the prospect lapse, it's a totally different, entirely different animal, right? A lapsed prospect never, they never proved anything. They raised their hand. Sure. They gave you, you know, an email address or a phone number. And lots of people do that to join those lists for discounts, but they never really might've even had intent to buy. So when the prospect goes cold, you're not really losing a proven relationship. There's nothing there ultimately. You're losing a maybe that's probably always going to be a no. Now, that doesn't mean the prospect is worthless. I don't want people to think that. Some of them are real buyers who just haven't converted yet. And we'll get to how you fight for those. But the emotional and the financial weight is nowhere near a lapsed customer. And this is very important to understand. And here's the reframe I want everyone to think about that unlocks what we're talking about. Because the losses are so different, the responses have to be different. You fight to win a customer back with patience and care. You've got to take it slow, but you have to fight to win a prospect back at the speed and aggression that if they don't respond quickly, you need to cut them loose, right? This, it's the same idea, but totally opposite results. So what do you think about that?

Yeah, that's a big one. I think a lot of people do this kind of opposite to how you've described. Too many marketers and companies are so patient and kind of gentle with prospects, endlessly resending like, we miss you, we miss you, we miss you, right? To people who've never actually ever bought. And then they're weirdly aggressive and discount heavy with lapsed customers, which just Absolutely explodes and kind of erodes that relationship that you've actually built the hardest to build. So I think again, it's the wrong way. And I think, you know, patience for the customer, aggression for the prospect.

All right, stop. I know you're enjoying this pod, but I've got just 30 seconds of your time real quick because I have a question for you. Is it just me or has everyone's tools gotten way more expensive lately? And SMS is where one of those tool prices continues to sneak up on you. You'd think, cool, it's just a few cents a send, but once you're sending like a real list, That bill really adds up because I've run brands and I've been on the ESP side. So I know what the pricing models work and how it's really priced. But SMS can look simple on the surface. And then once you get starting to send some volume, the bill starts looking a bit different. That's one of the reasons why I really like what Omnisend is doing right now. They just rolled out SMS pricing update. And guess what? They lowered the prices starting at just $0.007 per SMS, depending on the country and device. Volume, of course, but you're already sending email and SMS together and having it all in one platform. That matters a lot. You can build automations where email and SMS works together instead of treating them like completely separate channels. And secondly, Omnisend has been investing in AI. They launched their brand new MCP that connects Omnisend to ChatGPT or Claude. So you can ask questions, pull insights, check performance, move faster without digging through any dashboards. So if SMS is a real part of your growth strategy or even meaning to make it one, Go check out Omnisend. Head to omnisend.com/sendit to get started. And now back to your show. Yeah, that's right. So let's take the customer bucket first and let's talk about that because it's one of the ones that deserves the most care, in my opinion, and gets the least amount of thought. Now, the instinct when a customer lapses is to panic, right? Fire a discount at them. Come back, here's 30%. And I get that. But that to me is a little bit like begging ultimately. And begging does 2 bad things here. A, You don't want to signal desperation. And B, the last thing I'm trying to do is train my customer that lapsing is how you get a deal. You want to make sure your best people don't go quiet on purpose just to get a better deal. The better approach starts with a question most brands never ask: why did they leave? Because a lapsed customer doesn't lapse for one reason. They lapse for many, many reasons, I'm sure. And each one of them want a different response. Maybe they ran out of, you know, ran out and forgot to reorder. That's like number one and a very common one. Maybe they had a bad experience, a shipping problem, a product that didn't work for them. Maybe their life changed and they don't need the product anymore. Maybe they drifted to a competitor, they saw an ad. Those are 4 completely different problems and a blanket coupon addresses exactly none of them. What do you think about this?

Yeah, I think this is like essentially like where you have the room and kind of the grace to be patient, which you don't have with the actual prospect themselves. I think a lapsed customer has a longer fuse, right? And they're not gonna be offended that you emailed them because you have some sort and some regard of relationship. So you can build kind of this proper ladder over time instead of like this one super desperate type of blast. And you think of it as like a sequence that kind of escalates in some kind of like reasonable order. So early on, you don't lead with money at all. You lead with that reconnection, remind them what they loved or what they enjoyed or what they purchased. And then you wanna show them, you know, kind of what's new since they left. So ask genuinely if everything was okay with their last order, because if there was a problem, trying to solve that problem is gonna be way more valuable for both you and them than just trying to offer some kind of discount, right? And then further down the ladder for the people who engaged but didn't buy, you then can introduce like an actual reason to return. And even then, if it doesn't have to be a discount, right, it could be A product that's new, a restock of something they purchased. Here's kind of what you've been missing type of message. And then only at like the deepest end of this ladder for a customer who's clearly slipping away and hasn't responded to any of like your softer messages and nudges, do you actually kind of resort to bringing out like a real offer. And then when you do, you wanna frame it more as like a welcome back offer. It's like a one-time thing. Not like there's a new baseline price that you're going to have to send to them every single time.

And that reminds me, you know, as you're saying this, and I'm— it's 100% spot on. Let me add that the timing matters a ton here too. And it ties straight back to when we said the second purchase episode was a couple episodes ago, because elapsed isn't a fixed date. It's relative to your customer buying cycle. So if someone buys coffee every 3 weeks and they're on week 6, They're lapsing in my opinion, right? But if someone buys a mattress, six months of silence is probably completely normal. So your win back trigger has to be based on kind of the expected purchase cadence, not generic ninety day timers to the whole list. So the brands that do this well are basically catching the customers right as they slip past their normal order window gently before the relationship goes fully cold. And that's very different motion than waiting until someone has been like missing or. Not 180 days or 90 days or 130-day segments. Like, that's just taking like a random static date and then hitting them with a fire sale as well too.

Yeah. And then you're kind of much slower to give up on a customer. And I think that's the other half of the patience. Like, a proven customer earns a longer leash before you'd ever consider suppressing them, right? Because they've actually bought before and they potentially could buy again, hopefully will buy again. So the cost of keeping them on your list is quite low. Relative to their proven value and their potential kind of future upside. So the customer bucket is patience on the front end and patience on actually the back end as well, cuz you work with them thoughtfully. You don't cut them super quickly. And then hold that thought for one second, right? Because the prospect bucket is going to be then the opposite. So every prospect, right? So like on the prospect side, if we flip there, I wanna build this one around the concept that I think is key to all this, which is like The buyer's window, right? So every prospect who joins your list arrives with some certain amount of intent, and the intent has a shelf life. When someone signs up, maybe they browse, add to cart, whatever that trigger was, that's gonna be the peak for that person. That's the hottest they will ever be. And then from that moment and forward, their intent actually dwindles. It decays. And sometimes over days, sometimes it's a couple weeks, but it decays. And once it decays, dude, it goes fast. So that window from like that moment of peak intent to the moment, you know, that other moment we're talking about decay, it's basically gone, right? Like that's like the buyer's window and the entire game with the prospect is converting them within that window of time because once it closes, dude, the likelihood that you'll ever convert them is extremely low.

Yeah, that's exactly why the prospect win back has to be fast and why it's why treating a customer Win back is a disaster ultimately, like treating the prospect like a customer. So if you wait 90 days to win back a prospect, there's generally like nothing left to win. That intent has made worth anything evaporated probably at week 2 ultimately, 14 days in, right? You're emailing a course. The prospect win back isn't slow, isn't a slow patient ladder basically. It's a sprint. You have to grab them as fast as you can, grab their attention while there's still a flicker of intent. So the moment a prospect starts going cold and starts trailing off in engagement and drifting towards the edge of the window, you don't want to wait. You want to hit them, you want to hit them hard and fast. And then there's like something hopefully maybe there to reignite, right?

It's funny how much time brands spend trying to get more traffic and how little time they spend thinking about the traffic that they actually already have. Because every day people are landing on your site, they're browsing products, clicking around, And then they're leaving without buying or joining your list. And for most brands, they just accept this as normal. I don't know why, but they do. And this is where retention.com comes in. It helps e-commerce brands identify anonymous website visitors and turn more of that traffic into opted-in email subscribers. So instead of only marketing to the people who actually filled out a form, you can actually grow your list from the visitors who are already visiting your site. And what I like about it is that it's flexible. You can start free, you can turn it on when you need it, you can pause it when you don't, and you just pay as you go. There's no big annual commitment, so you just test it, and if it works for your brand, you keep using it. It's basically a way to get more value out of the traffic you're already paying for. Go check it out at retention.com today. And now we're back to the pod. For sure. And then I, I'd say like, this is where like aggression's not only okay, it's actually Most often than not the right move, which again, I know is going to be like really hard for most people to wrap their heads around. So I want to really quickly kind of try to justify this for the folks that are listening. So when you think about collapsed customer, aggression is dangerous because you can damage a potentially really valuable relationship. Or with a prospect, there's almost no real relationship to damage. They never bought. And if you push too hard, you know, they're going to probably just unsubscribe, right? So you lost a maybe that was trending towards a Most likely a no anyways. So the math that you actually run here on like the risk is 2 different scenarios, which I think is like the essence of what we've been trying to say here. The downside of being aggressive with a prospect is small. Downside of being timid is that they slip out of the window and become just dead weight on your list. That's frankly worth zero to you. So you wanna lead with your strongest stuff first, your best offer, Your hardest urgency, your most compelling reason to act right now, essentially.

And I want to add to this aggression thing because I think it's a good topic because being aggressive is useless without any kind of specifics. Like, okay, let me make this a little bit more clear. For a fading prospect, this is where you throw the real punch. Basically, you lead with your best converting offer, not some watered-down one. If the discount's ever going to be justified, This is it, right? Here's the one that you want to like throw at him because this is really your last chance ditch effort. You have to use hard urgency with real deadlines because you're going to force a decision inside some type of closing window. You may compress a timeline, a tight sequence over days, but you don't want to leisurely drip over months here. You may ask for a dead simple one obvious action because you're not nurturing relationship. You're trying to get a conversion before the lights go out basically. So, you know, just remember the whole energy of what aggression means is very different versus a customer win back, which is more of a conversation. A prospect win back is like a last call. That's like the best way I explain it.

And then the reason like you can be that aggressive without guilt is the piece we're about to get into here coming up, because there's a hard deadline on the prospect. And if your aggressive push doesn't work, they don't just sit on your list forever. Like they, they do need to leave. They do have to go. And that's really for like your list health and your deliverability. And I think this part separates the people that understand email from those who just press send without any regard. When a prospect doesn't respond kind of to this aggressive win-back, the correct move is to then not keep emailing them. The correct move is to remove them from your active sending, sunset them, dump them into some kind of hygiene. And I think it's really important that like this isn't about being just neat. Unengaged subscribers are gonna actively hurt, you know, the entirety of your actual list.

Yeah, that's a good point. Uh, we didn't even get into that, you know, the holding of prospects. Is definitely a mechanism that's going to hurt you. Things like Gmail, Yahoo, Apple, they decide where your emails land based heavily on engagement these days, and especially even on placement. And if people aren't or are opening, clicking, replying, or they're ignoring you and deleting you, when that list starts getting larger and larger and the percentage of the people doing that, it's going to start affecting your overall metrics. And that signal doesn't just hurt you with the dead people, drags down your placement for everybody ultimately. So you can have good customers, the ones that love you, they start landing in spam or promotions or, you know, AI's filtering it out because your overall engagement looks terrible. So you're literally sacrificing your best subscriber deliverability to keep emailing people who will never ultimately buy.

Yes. And that trade is one that I don't think people think about. Everyone's just on default kind of mode and doing it the way that they've always done it. We're like keeping the dead prospects on the active list Does feel harmless, right? It doesn't feel like it's a big deal, but it actually is potentially really detrimental, especially the longer that this goes on. You know, so again, a prospect gets your aggressive win-back push, one concentrated strong sequence inside their actual window. They engage, great, they're back in play. If they don't, they come off the kind of active sending list. You know, you suppress them, sunset them, you move them to like this rarely touched hygiene segment. And then this is where kind of like the 2 buckets that we've been talking about really kind of diverge. The customer gets a longer leash and a lot of patience. The prospect gets aggressive shots and a faster exit.

So real quick, I've got 30 seconds of your time right now. I would love to tell you about something I've been personally working on that I think is really interesting and that's led me to discover these guys. So I've been in my other business running advertising on Meta specifically. And one of the things that's cool about advertising, if you're a retention marketer, you may not know this. What I do is I upload a headline, a body, an image, and a link or a call to action. And then Meta transfers all of those around in circles until it finds the right winning combination for the end user. And I wondered, why aren't people running an email this way, the way that people are running ads? Imagine if I could just upload headlines and images and angles and, you know, AI is smart enough where it's gonna be able to pick the right things and put it all together and send out the email. But the reality is today is people are getting one email, one hero, one offer, and it's going out to 50,000 people on the list. That's why one of the cool tools that I saw is a tool called Allen. It caught my eye. It's very unique. You stock it basically with a library of things and Allen will generate the assets and send real emails one-on-one to each subscriber. So if you send it out to 50,000 people, it will send 50,000 individual emails specifically catered to that end user. And it sits on top of your Klaviyo or your Omnisend, of course, holler at Omnisend, of course. And so go check it out. It's getallen.com and you can start for free and you can test it out in your next campaign. There's nothing to migrate. You just stock some assets in, you set some stuff up. They'll even help you out over there. So go check 'em out over there. Let 'em know Chase and Jimmy sent you. getallen.com. We'll see you back in that video. All right. So I totally agree with you, but I want to hit them with this emotional block that people might be having. I know exactly what people are thinking, but that's a subscriber. I worked to get them here. It feels wrong to stop emailing them. That's definitely a thought process that I feel like runs through people's heads. And that feeling is costing you money. A dead prospect on your active list is not an asset. It's actually, in my opinion, liability. And they're not going to just buy. They're hurting the people who will potentially buy. Letting them go isn't a loss. It's a clear win. cleanup that makes every other email perform better. This is really important. And you know what? I'm sure you know as much as me, Chase, the best brand, they're ruthless about this stuff. They'd rather have a smaller, hotter list that lands in the inbox than a big bloated list that lands in spam because size is a vanity here in 2026 in the future and engagement is a thing that actually pays. You agree?

Agreed. And this is like where your tooling should be doing the work for you. Now you want the engagement-based segments and the sunset law, kind of logic running automatically. So prospects who go cold get their aggressive sequence and then they get pulled from active sending without you having to babysit it. So for example, like a platform like Omnisend makes this super easy and manageable because you can actually set like the engagement rules and then the win-back sequence once and then let it enforce the discipline for you instead of having to rely on somebody who actually remembers to prune the list every quarter. Because let's be frank, that doesn't happen.

It never happens. The manual version of list hygiene is, we will get to it. And you generally never get to it. It has to be some level automatic or it doesn't exist. So anyways, I think we've beat this dead horse. So let's kind of bring this together because the practical risk here isn't running these 2 win-backs as one flow, which everyone does, which is why, in my opinion, win-back kind of unreforms. The first thing you have to do is almost separate the 2 audiences at the segment level. So here, people who have purchased, yes or no, like that's the first thing. The question splits your entire win back into 2 buckets and everything downstream branches goes from there. So when customers go quiet, they route into the patient ladder, ladder it off with their purchase cadence, leading with some kind of reconnection message, holding a real offer for them in the deep end, right? If you have to go there. Where prospects, That should fire off much faster because they go cold much faster. Aggressive sprints inside their window. And you've got to like offer them the most aggressive offer that you can do. And the trigger will be about the same, but going quiet has 2 different meanings. You can almost design them as 2 different flows if you really want to, because that's what's going to work. Anything else you'd add to that?

I would say like you also want to measure them differently, which matters because if you judge them by the same metric, I think you're going to just have wrong data and wrong kind of crossfires from both. I'd say for like the customer winback, success would be like reactivation and then the value of the customers you bring back, right? So you're playing for a high-value relationship. So even some sort of modest reactivation is a real win in my opinion, because each person you reactivate could potentially be worth quite a bit. And then for like the prospect winback, I think success could be defined by 2 primary things. Right. Did you convert some of them inside that window? And just as important, did you cleanly remove the ones who didn't so your deliverability stays strong? Right. I think the successful project program shrinks your list on purpose, and that just is a sign that it's actually working.

Yeah, this is definitely a mindset shift. I would say for many, a win-back program that never removes anyone is not a win-back program. It's a hoarding program. And I really want people to stop hoarding their list ultimately. And that's part of the conversation here. So wrapping this up, Real quick, win back has 2 problems, not one. Customer win back and prospect win back. A lapsed customer, just remember, I'm going to beat this like a dead horse a little bit. Lapsed customer is a proven paid-for data-rich relationship that it only hurts to lose them. So you got to fight with patience and diagnose why they left, build a reason for them to come back and discount them at the end if you have to, to try to bring them back. Where a lapsed prospect never proved anything to you and their intent is going further and further away the longer it's been since they've opted So you have to fight with speed and aggression, the best offer, the hardest urgency, the tightest timeline. And if they don't respond, well, you got to dump them because your hygiene really, really matters around there. So if you do one thing this week, I always tell people the easiest way to start is to split your win back with one question. Has this person purchased? Yes or no? If they said no, put them in that other group. And then you got to figure out the timing. That's on you. If you go back to that second purchase, a pod. We talk a lot about timing, so you should go check that out. And the moment you see these 2 lists instead of one, the right strategy for each one becomes very obvious here, and you'll realize that you've probably been treating both of those exactly the same. Any final thoughts here, Chase?

Um, no, just kind of round it out. Patience for the proven, speed for the maybes, and the clean exit for those that you deem kind of as dead weight.

That's a fantastic way to end today's episode. Thank you for tuning in. As always, We'll see you next week.

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.