Stop ignoring these emails (they get the most opens)

Transactional email doesn't feel like marketing to a customer. Anything you layer into the email gets received completely different frame of thought than the same message you would've had if you sent it in a campaign.

The goal is to enhance, measure both sides, and never let the bonus compromise the core.

You are touching the most trusted, most critical emails in your systems and make sure that you're keeping an eye on it.

Transactional email is not a receipt with some branding. It's the highest trust, highest attention moment you get with your customers.

From the open to the click, they're the masters of the flow. Just watch your list grow. When 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. What is up everyone? Welcome back to Send It, where we discuss anything and everything retention marketing, specifically in email and SMS marketing and e-commerce. I'm your host Jimmy Kim, and I'm here with my co-host Chase Diamond. Oh, I fumbled that a little bit today. But listen, Chase, today's episode is all about emails you spend zero time on that happen to be your best performing emails in your entire business. Here's what I mean. Look, you pour hours into your campaign and you obsess over your subject lines, you A/B test the 2 hero images, and then you argue with your team about send times. And then that email, the one you sweated so much time and energy with, gets opened by just a fraction of your list. Meanwhile, there's a whole category of emails going out that your brand that gets opened by almost anybody and everybody that you probably never even think about. And some developers set it up 2 years ago and no one's touched it. And you got some guesses, Chase, on what that might be?

Order confirmation maybe, or the shipping notification or something about like the package is out for delivery. Is it some of those?

Exactly, man. The stuff that people treat like pure utility, and those are actually the emails with the highest open rates by a mile, but most brands use them like receipts and nothing else. So that's what I want to cover on the pod today. These are the most open, most trusted, most anticipated emails that the ones that are completely being ignored. And today we're going to work on fixing that together, but carefully because there's a real line in how you can cross that if you can get yourself in trouble. So I don't want people to hear this and just run off and make these like total marketing messages. That line is the part that nobody really talks about. So let's spend some time on that. And because advice here is not to put offers in your order confirmation, it can also hurt you in a negative way and torture deliverability and stuff like that. Plus it could start breaking laws if you're using it like a transactional message. So you got to be really careful here, but we're going to cover on today's pod why these emails are great and why they crush, why they're the most valuable real estate you probably own in the email side of things and everything you can do to push on them to that fine line and a playbook that actually do. So you want to, let's get to these things and get going on it. So let's start with the numbers because I want you to internalize this so you can't unsee it basically. A transactional email, an order confirmation, a shipping update, they get opened at a rate that's matching, that makes your email marketing potentially look bad. I'm talking about like the multiples. We're talking about like, 80, 90, almost close to 100%. And then depending on the type of brand you are, an order confirmation can pull open rates way better than any of your campaigns, mostly because people want them. It's psychology, right? When people buy something online, they're at this heightened state of awareness and they're in this like excitement bubble basically. And they just bought the thing they want. And there's this a little bit of anxiety. They just sent money on the internet and they're not really sure it works. They go looking for this thing called the confirmation email. That resolves both. So you don't just open it, they wait for it. They're actually looking for it. You know what I mean?

Yeah, 100%. And then one thing to add is like all of this compounds across the entire shipping journey. So like every stage here has its like own little spike of attention, for lack of a better word. So for example, maybe like the order confirmation. So that's like, did it go through? You know, they're wondering. The shipping notification's like, okay. It's really actually happening. You know, it's on the way. This is exciting. I'm pumped. The out for delivery is like, it's almost there. You feel like a kid at Christmas just waiting for that morning of gifts and presents. And then like, you know, with that, right? Like every single one of those moments is where the customer is actively, eagerly opening an email from a brand. Dude, you know me, I'm like the most impatient person. As soon as I get those things, You know, I'm pumped, I'm pumped. And you'll never ever get that level of attention from an actual marketing campaign, right? In this type of opportunity we're talking about, the person's leaning in, whereas with marketing, you're interrupting their day, you're interrupting them and then hoping and praying. Whereas it's this transactional email world that we're talking about, it's quite the opposite. They're coming looking for you.

Yeah, so then the obvious question is, if these are the most open, most wanted emails a brand sends, Why does every brand treat them like garbage? And I think there's 2 reasons and they're both a little dumb once you say them out loud. So I'll tell you what I think it is. The first is the ownership. So transactional emails usually get set up by a developer or they come default out of the platform and they live in a different part of the system than your marketing team usually is involved in. So the marketing team doesn't even think about them as their own. They think about it as IT and as IT, nobody thinks about this as marketing basically. So nobody on the growth team ever opens their own order confirmation and goes, what could we do with this? Right? That's just not something that happens very often. And the second reason I think is that they just look boring. So people assume that they're supposed to be boring. It's a receipt. A receipt is utilitarian. It's the end of the story. And nobody questions whether the single most opened email in the business may deserve just a little bit more Than great tables of items. What are your thoughts here?

Yeah, that's a good point. I think like the ownership piece is, is really kind of painful, um, there because I think it basically shows you that like the most valuable inbox real estate you have is just sitting part within this organization, um, that has no incentive or no reason, or maybe you don't even remember to actually optimize it, right? The dev team's job is that it sends and that it's accurate. And then the other job is that it, you know, is that it goes through, right? Like, not that it actually drives the second purchase. So it kind of just sits there, collects dust. Technically, it works, but it just doesn't look good. There's no appeal. There's— it's not exciting.

Yeah, I would say that it's technically working but commercially dead. That's a good way to think about it. That's what most transactional emails in ecommerce in just like one little phrase.

For sure. And then with that, right, like I think we should go into like what people are leaving on the table here because the magnitude of this is quite important. Like if you think about like what a transactional email really is, in a world of like open rates and kind of uncertainty, like this is one that actually people legitimately do open, right? There's a lot of trust there and there's a lot of attention with a customer. At the exact moment that again, they're most engaged with your brand. So if you try to buy a placement like that, if that were an ad unit, it's gotta be, I would say, the most expensive inventory that you could bid on across the board. And you own that moment, you own it outright. You don't have to pay anyone for it. You just need to take better advantage and utilize it more.

And the thing you mentioned about the trust piece is the part that people underrate basically. A transaction email doesn't feel like a marketing to a customer, which is exactly why I think it's so powerful. When the campaign hits, there is a little wall that goes up for the consumer, right? Here's a brand trying to sell me something, yada, yada. But the wall is just human. But an order confirmation, as you said, gets none of that. It's welcomed. It's useful. Your guard's down basically. And you really want to know what's going on in that email. So anything you layer into the email gets received completely different frame of thought than the same message you would've had if you sent it in a campaign. And you're talking to someone who trusts specifics on email. And it's happy that it arrived. 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 to 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 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 their prices starting at just $0.007 per SMS depending on the country and the 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 you've been meaning to make it one, go check out Omnisend. Head to omnisend.com/sendit to get started. And now back To your show.

Yeah, well said. So I think the best way to think about this, like the best reframe here is that a transactional email is not a receipt with some branding. It's the highest trust, highest attention moment you get with your customers. And the transactional function is the reason actually why they opened it. So the receipt is basically like the Trojan horse. It's like your ticket in. And then what you do with the rest of that is the opportunity that you need to take advantage of. And don't waste it like most brands waste it.

And here, and let me add something, something, some things I want to be really clear about because this is where people hear this episode and go off and do something dumb. The opportunity is real, but the second you get greedy with it, you're going to lose the entire thing. So both trust and potentially the legal right to send it the way that you've been sending it. So before we give you the playbook, we want to kind of almost set up some guardrails, some doors, some ways to make sure that you don't hurt yourself because this is the difference between a smart brand and a smart marketer and a brand that just, well, they nuke or hurt their own deliverability pretty bad there. So there's definitely this part of it. What do you think?

I know this sounds super boring and the part that no one wants to listen to, but please do not skip this. This part from here on out is very, very, very important. So let's get into it.

Well, I want you to do it, Chase. Why don't you tell them and walk them through them? Because I think you could deliver a good solid bad news, but in a good tone kind of thing. So you tell them where the line is.

All right, sure. So kind of the quick disclaimer up top. Again, we are not your lawyers. We are gonna try our best to give you as much good advice as possible. But if you're doing anything serious here, please do consult your own lawyers. But essentially here, like the concept in email that you need to understand is like the idea of the primary purpose of an email. You know, in copywriting, it's a similar thing where we're kind of focused on a single big idea. But essentially what happens here is like the reason that transactional emails Our special is not just deliverability, it's the legal part. So under the rates that govern commercial email, a message whose primary purpose is transactional or relationship-based, you know, confirming an order, giving shrimpy info, handling an account, getting treated differently than a kind of commercial marketing message. So basically different rules apply to it. That's why an order confirmation can go to someone, even if they've actually never opted in. To your marketing. And why does it need the same unsubscribe machinery that like the promo blast does?

Which is exactly why it's so tempting to abuse, right? So, oh, this email reaches everyone, doesn't need an unsubscribe button legally even. Let me stuff up with a bunch full of offers. And that's the trap, I would say.

Yeah, 100%. And with that, like the mechanism of it. So the special status with this type of send is tied to As we talked about before, like the primary purpose of it staying transactional in nature. So the moment that it becomes very promotional, right, the promotional content becomes the main point. Well, now the actual purpose of the email flipped entirely. So if you think about it from a legal perspective, it's now a commercial email that is being sent as a transactional one, whereas the commercial email part that has to follow then the commercial rules, including the working unsubscribe, and then kind of the honest way of abiding by the people opt in or not. So you have potentially now sent someone this commercial content to those who have never opted into your marketing or those who actually potentially that even explicitly opted out, which no longer takes it from like this kind of gray area. This is a thing that actually can get your brand in a world of trouble.

The way I keep this simple is that transactional information has to genuinely be the star of the email. That's really the key here. Not a line on a sales flyer underneath. It has to be actually the primary hero message of here's your order information. This promo that we're talking about has to be almost a supporting act, the guest, right? It rides along under the real content. The second offer becomes the reason the email exists. You've crossed the line. That's where this is really important to understand.

Right. And I think it's not just the legal side either. There's also like the deliverability layer sitting on top of that that I think hurts people sooner, kind of day to day. For example, like transactional emails very often send through a separate kind of stream, for lack of a better word, where there's like a different system, some kind of different IP or subdomain. Specifically so that your critical, did my order go through messages always land, you know, no matter what your marketing sender reputation is doing. So that separation is a feature and it protects the emails that absolutely need to arrive.

Yeah. And basically when you start jamming promotional emails into that stream, you're risking that protection you just basically talked about.

Yeah, exactly. Or you can basically drag your marketing reputation problems into one stream that was supposed to be Like a sure thing or as much of a sure thing as possible, right? And now you've jeopardized the deliverability of the actual receipts, which is one email the customer will file a support ticket over if it doesn't show up. They're expecting it, right?

Yeah. So long story short, I think what we're saying is you could end up in the wrong, uh, worst of both worlds if you're careless about this. You break the trust, that's a problem. You risk legal status and you can contaminate one of your sending streams that you need to keep Very, very clean. All this to shove a 10% off banner into the receipt. That's basically the thought, 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 fill 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. Yeah, for sure. Exactly right. So, uh, keep the guardrails simple, right? So transactional content stays as the clear primary purpose, as Jimmy mentioned, the star up top. Unmistakable. Whereas then with the promotional element, that is going to be secondary and kind of supplementary, never kind of the primary point. So anything security or account related, password resets, login alerts, those are clean. That's not marketing. End of the story. And you have to understand how your platform separates transactional from marketing. So you're not ruining kind of that transactional special send that we're talking about.

Yeah. All right. So, you know, as kind of Chase has talked about staying in the line, you've got to make sure that, you know, you don't want to get into any kind of liabilities or anything like that. So there's a ton you can do though. Do you want to walk into some examples here?

Yeah. Should we go email by email maybe? Yeah.

Yeah. All right. So I'll walk and I'll start with this thing with like the actual shipping journey. Okay. The email by email, I'll give you what belongs where. All right. So let's start with the order confirmation. This is the highest open rate in the whole set. So it's the most valuable and the one you want to kind of get right first. The order details stay front and center. That's the hero message. But underneath it, the best additions are things that reduce anxiety and build anticipation. What happens next? How to get the most out of what they bought? Or if they've— if you're going to merchandise at all, tastefully move to genuine, relevant complement of what they've ordered, not some random bestseller. So if you can make it tie in together, that'd be great. So example, someone who bought a coffee maker, seeing the beans to go with it might be helpful. Or someone who bought a coffee maker seeing here's 25% off of hoodies, that's really just not going to connect, right? So that's the first one I think about. The second email that I think about is the shipping notifications. That's an excitement peak. It's really happening. It's on the way. The tracking info, that's the star of the message, right? But it's a fantastic place to put content rather than just a hard sell. How to prep for the product, how to use it, what to expect when it lands. I mean, you're building anticipation and setting customers up for a great great first experience, which actually drives a second purchase later, of course. A soft referral or share what you got ask also fits here, but the excitement is real in that moment, in my opinion. Then the third one I think about is the out for delivery or the delivery notification. This is one of my most exciting ones because that means that it's almost here. The product is about to be here, and this is almost your onboarding moment. Point it to them on how to use it, how to get the best results, how to get a quick start, self-care instructions, all that stuff. And the more you can get in front of them and tell them exactly what to do, it's not only going to reduce returns but increase satisfaction, but it's also going to start opening their minds up to the cross-sell. They also want to setting up for an eventual review request, of course, though you don't want to actually ask for a review before you see the thing. So I'm not saying stick that in there, right? And then after that is probably the last one, which is like the post-delivery follow-up, which is arguably the bridge between your like transactional and the start of what we call lifecycle marketing. Once they have the product for a little while, This is where the natural home for like you ask for like UGC reviews, but the replenishment setup, if it's a consumable or if you have some kind of genuinely good next purchase, this is where the transactional journey hands off to the retention program we talk about on every other episode we talk about. And so when one— I want to add one more actually. I got one more, which is something that people forget, the back in stock and account notification. Back in stock is basically a transactional message with an enormous intent baked in. Basically, They're sitting on a website, they see, you know, the product's out of stock, but you can put your email in and get it. So you treat it with urgency and make the path frictionless, right? Account security emails, things like that, you leave alone. You don't want to mess with those things. And the same thing with the password reset. I wouldn't put anything more than like a banner on there. But what I'm trying to say is that there's a lot of places where there's space where you can still kind of tap into.

Yeah, I'd say like with this, right? Like every one of what you mentioned reduces anxiety or builds some kind of anticipation. Anticipation, or then improves kind of the overall product experience, or then teases a genuinely relevant next step, right? So essentially, like, you're enhancing the customer experience through, like, the emails that they're actually wanting. You're not distracting or taking away from it. And then with this, right, like, it makes the transaction better for the customer, right? It makes it more helpful, more interesting. If it makes it Worse kind of to serve you, you become like the thing we warned about a minute ago. So I think that's super helpful what you mentioned.

Yeah. And this is the spot where a good tooling, a good platform earns its keep because the dream is your transactional emails and your marketing flows aren't 2 separate worlds that you don't know anything about each other. That's kind of the problem that exists and why. But platforms like Omnisend, for example, let you bring real logic into the send so you can complement and show those order confirmations and reflect what they bought instead of some static banner that you hardcoded back in like 2022. And you can even mark them transactional. So Chase, how do we know if any of these are actually working? Like, that's a good question that I think people are going to ask as they start thinking about this. 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 going to 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 the episode.

Yeah, for sure. I'd say like, honestly, the upside here is obvious that people forget to actually track and prove it. And then with this, right, like these emails get opened at rates your campaigns can only dream of, right? Like actually that. So even like a modest click-through rate here on some of like these relevant kind of tasteful additions can produce like strong, real incremental revenue because the open side of the equation is massive. Like if your campaigns are getting 25 or 30%, whatever that looks like, open rate, Dude, I wouldn't be surprised if this could be 2 or 3x that, right? So you wanna track the clicks and then the revenue coming from these new additions. That way you can understand the logic behind it. And I do wanna go out on a limb and say, I can almost guarantee that if you do these and you're not doing it already, the number of clicks and revenue you're gonna drive will really surprise you relative to the low amount of effort it's gonna take.

Yeah. And let me just add like a devil's advocate caveat here.

Sure.

And this is a place where like most people skip with these things. You are touching the most trusted, most critical emails in your system. So make sure you're monitoring for damage. Support tickets are going more up because receipts confusing, for example. Are complaints ticking up? Did anything happen to your deliverability of the transactional stream? Like you just want to pay attention to it, especially when you first start it and make sure that you're keeping an eye on it. Because if you add content and the core transactional message function gets worse in any way, You want to pull back immediately. The job of the transaction is the main goal here, but the revenue bonus that rides on the top is what can keep it going if it's done right. So that's something that I want to kind of advise there too.

100%. Yeah. And with that, right, like the goal is to enhance, you know, measure both sides and never let kind of like the bonus kind of compromise the core. You know, if the receipt becomes— I'll give it a stop. If it becomes like a great receipt, that's great. And then nothing else Matters if it's not a great receipt. So it's really important that you follow this to the plan that we laid out.

Okay, cool. And I think we got this message home, but look, just like a TL;DR right now, your transactional email, your order confirmation, your shipping notifications are going to have your highest engagement, highest open rates, because they are your highest trusted emails that you can send. And most brands treat them like plumbing and they forget them all about— all about them, all Ultimately, but they are very valuable real estate because your customers will look for them with their guard down and you can turn them into revenue and a little relationship. But the purpose needs to stay transactional from the start and the promo can go underneath. You can educate them, you can start warming them up with education content and even just a little promo and it could help you get a little bit more extra edge on that first relationship email that you can get it out there. So if you're doing one thing this week, here it is, go to your own order confirmation email Just look at it as a customer. I bet you, first of all, it's probably this gray receipt that a developer or it came out of the box like that and no one's really touched it. Start by branding it and making it look better and linking it to little things like instructions or challenges. Even put a little next order bonus on there. You can play with it. Just make sure you don't lose the hero of the message, which is the transactional emails. You should show it to other people, make sure that they see it and see the order information first before they see the transactional stuff, but make sure you're using that valuable real estate. Chase, any last final words here as we end the show?

No. As a recap, I think, or I guess the last thing I would say is like, this really is the email or kind of like the series of emails that most people never think about, but the ones that like legitimately everyone opens. So you really do need to make it actually count.

Yep. With that being said, dude, it's a wrap for this week. We'll see you guys later. Thanks for tuning in and we'll see you next week. See you guys later. Adiós. 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.