The Secret to Higher AOV: Cross-Selling and Upselling with Email & SMS in eCommerce - EP20

While you do want to stay in front of people and you do want to follow up and you do want to stay top of mind, you also want to limit though, like how often you're actually hitting someone with these specific cross-sell and upsell offers so that way you aren't fatiguing them, right? So there always is a line.

Make sure the messages are short and timely, right? Your product is on the way. Pair it with blah, blah, blah. Use bundle blah for 10% off, right? Like really simple, straightforward messaging because you know that the product pairs really well. You don't want to burn a lot of credits on it. So it's really easy to just kind of add that little blurb.

You want to identify which products and combinations make the most sense for cross-selling and upselling at the same time? Like when you sell this, what kind of evolves and exists with this, right?

You need to cohort major campaigns. And what I'm talking about is not just for your email and SMS, but you gotta be thinking about this entirely as a business, right? You know, you got your key sales items, your product launches, your holiday promotions on your main calendars, but you should also plan upsells and cross-sells around these events that naturally fit the narrative. Yo, Chase, what's What's good, dude?

How are you, man?

I'm good, man. I'm ready for this pod here today.

I'm ready to run it. Let's do it.

Dude, it's episode 20 here. You know that podcasts, only 10% of podcasts gets to episode 20s and above, I think is the stat right now.

That's crazy. I believe it though. They're hard. So congratulations to us.

So much work. Yeah. Congrats to you too. And congrats to everyone listening. Thank you for that. So with that today, I have a masterclass, a masterclass for this milestone on cross-selling, upselling for AOV. We're gonna get real tactical here. So you ready to shoot this one?

Dude, let's give the people what they want. Let's do it.

All right, let's do this in 3, 2, 1.

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.

What is up everyone? Welcome 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, today episode 20, we're gonna talk about cross-selling and upselling for AOV growth in email and SMS marketing. This will be a masterclass on strategies, timing, and automation. So today we're going to go beyond the basics of cross-selling, upselling. Everyone knows what those are. And we wanted to get tactical and go step by step and give you an approach to seamlessly integrating these strategies into your email and SMS. But before we grab into specific automations and different tactics, let's talk strategy. Chase, I want to start off with a question, and I know I sent this to you already, but why should you— why should anybody who's listening to this thing think about cross-selling and upselling from day one?

Yeah, there's a lot, right? I'd say the 3 primary things that kind of come to mind. Number one is, this is something that you have to consider and think about. You have to know your product ecosystem, right? So you should do kind of, whether it's on paper or digitally, some kind of map out of your products and how they pair together, right? What is stuff that people will typically buy like in a bundle or at the same time that complement one another? So it could be something like a hero product plus accessories. So it might be a t-shirt, and then it might be things like a hat or a bracelet or pants that maybe are going to complement that t-shirt if you're, let's say, an apparel brand. And then with that, right, like you also want to identify kind of the, the natural ascension and descension, right? So what are kind of like the premium tier products for clear upsell paths? And alternatively, right, you know, if you can't get people to take the upsells, how do you get people to take kind of more of the, the downsells or the cross-sells, would you have you? So that's number one is just really knowing your customer, knowing your kind of SKUs in your product line. Number 2 is with that, you wanna segment your customer base. So you're gonna wanna study kind of past behavior, right? Past behavior is gonna be helpful and be indicative of potential future behavior, right? So segments could be things like people that frequently purchase. And if that's the case, what are the things that they're frequently buying? Where can you draw kind of the line in, in the patterns? And then maybe there's first-time buyers. What did they buy for the first time? And what did other customers that bought those same or similar items for their first time, what did they buy on kind of some of their future visits and whatnot? And then additionally, things like the average spend pattern. So are people buying things when they're on discounts and they're kind of more low spenders, or are they buying things no matter whether it's discounted or not that are really expensive, like your best sellers that have no discount, right? These are kind of more of your high spenders. And then there's obviously gonna be folks in between. And then I'd say the last one is really setting your goals for your AOV increase, right? So if your AOV is $50 and your goal is to get it to $75, like what does that look like? How do you get there? So you have to decide that target percentage or that dollar increase that's appropriate. You know, that, that $25 increase may or may not be appropriate, right? Maybe you don't have a way to get there, or maybe that's too small, right? Maybe it should be towards $100. So You wanna align kind of your cross-sells and your upsell plans with really that KPI. I know that was a lot, but really kind of the, the key here is you can't just randomly suggest and throw things out, you know, without any kind of rationale or reason. You really wanna define these pairings and these upgrade paths that make sense for your brand, which ultimately are gonna make sense for the specific customer segments that you're setting up. Does that make sense?

Yeah, no, that makes so sense. So know your product ecosystem. You got to know how to segment your customer base and then you got to set goals. I love that. All right, let's get tactical about this because, you know, when you think about the exact points in a customer journey, when there's a cross-sell and upsell automation that should occur, there's 2 different types of points that triggers in my opinion, right? There's the post and there's a lifecycle.

Yes.

So let's dive into the chase. I'll kick off the pre or the post-purchase triggers and then you'll jump over to the lifecycle. So for me, right? When I think about the post-purchase triggers, it starts with the immediate upsell on the post-purchase. So, you know, we're talking about soon as they've made a purchase, order confirmation or a thank you page. And, you know, the tactic to me is very simple. How can you get someone to complete their set or upgrade now with the discount? Now, I don't love discounts provided in a general blanket term when you're selling something. So when they made a purchase discount, but I do love if you can coordinate a perfect product to a person and say, hey, I want to show you a product. And we've seen cool little tools that do this in like, like the upsell funnel. But in my opinion, on top of that, knowing that email number 1 is that first email that people are going to get and they're most likely going to open that, there's a super high percentage. And that timing of right after purchase is so key, right?

Yeah.

The second part of that post-purchase, in my opinion, is the post-delivery cross-sell. So I'm talking about when the product is delivered, right? You know, we're all using great tools now these days that are identifying when tools are being— I mean, not tools, but when products are being delivered. So if you can get in there and you can be really timely, hope you're loving your brand new product, uh, people often get that product with this accessory, right? And really giving them a couple of days after they've received their delivery confirmation and being in front of them. And that's to me, really, really powerful ways to think about upsells. So you think about that. And when you think about that, Chase, you know, there's also the lifecycle thought. You know, I gave you those 2. What do you think about when you think about lifecycle ultimately?

Yeah, for me, the first one that comes to mind is like the replenishment or kind of the reorder. So for example, right, like people buy something that's topical or consumable, maybe it's like a multivitamin or some kind of protein powder, right? These, if you use them properly, like if you use them daily in the case of a multivitamin, that's gonna run out after 30 days, right? So these things, you know, that you sell, they're gonna run low after, you know, a specific or an estimated period of time. So with that, you wanna set up kind of emails and automations around these triggers that, hey, is it time to reorder? You know, make sure that you reorder now so you don't run out of the product. And then with this, right, like you can add these additional and kind of complementary products for a discount, right? So you know what someone bought, let's say they bought the multivitamin, you want them to buy that again, because that's something that they should be using, you know, day in and day out. And alongside that, right, what are the things that are going to complement the multivitamin, right? Is it A fish oil? Is it a protein powder? Is it a collagen? What are the things that you sell that would be good for someone's health and well-being? And with that, like the timing, depending on what you sell and the frequency and the quantity, it should be 30, 60, 90 days post-purchase. Again, depending on what it is. If it's a multivitamin, you know, you should be doing that somewhere in the ballpark of like day 21 to day 30. You know, get ahead of it. Hey, you're about a week out from running out. Make sure we order now so you've got time to get the actual item back in stock. And by the way, while we have you, here are 3 other things that we know that you're gonna love based off of what other customers in your same shoes have purchased and loved as well, right? So that's that one. That's a really big one. I think that's an easy one to do to just drive that constant repeat purchase and whatnot. And then the last one would be kind of the milestone upsell. So some kind of milestone. Whether a customer hits a third purchase, maybe it's some kind of a year anniversary of the last purchase, right? Whatever it might be, trying to get people to take some action based off what you know about them and what they've done. So, hey, thanks for your third purchase. You're now an exclusive member. Here's your chance to upgrade. And you want to do this right when that trigger is hit. So for one person, their third purchase could happen within a couple months, might happen in 6 months, might happen in 12 months. But having that trigger set up is a really great way to get people excited about that purchase and hopefully get them to keep buying time and time again from you.

Dude, I love that. You know, lifecycle is one of those terminologies I think are used really broadly in this market. But when you think about what lifecycle is, those 2 are the truest lifecycle triggers, which is very standard and people don't think about them. And they're actually not really well used in the flows of many brands out there because I've definitely been a 3rd-time customer and they never seem to know. But with that, let's jump into the nitty-gritty on how to construct these flows because I know that If we're going to nerd out on this stuff, we want to get really deep into it. So let's talk about the email structure flow, and I'll kick it off with 2 things. And I'm sure you've got 2 or 3 things that you can kind of share with, but let's talk about it. So for me, when I first think about making sure we're setting this thing up, first thing I'm thinking about is the segment setup. And I'm talking about using past purchases to identify segments who've brought— who've purchased product A but not product B. That's really nice to do because look, most brands, you know this, Chase, they're only 3, 4, 5 products that most people are buying, uh, as they're like main hero brand products. And that's where I'm focusing my energy on because I don't need to go off and identify every little product because I may have a lot of SKUs, but I need to look at my hero products and look at those ones that people are upselling to because it's going to be clear and identifiable, right?

Yeah.

So with that, that leads me to the second part of that segment, which is also starting to split up, as you kind of mentioned, high-value customers versus low-value customers. And really even down to different messaging. It's also depending on if they made their first purchase and they made high value versus their second purchase and made their high value, because some people might've bought the first product, had to kind of dabble in and then said, hey, I'm going to get in there and I'm going to start buying that bigger product because now I'm more confident with the product. So that's the first thing I think about when you're thinking about your flow structure is making sure you're thinking about your segments that are happening in real time. And from there, it really drives into the second point, which is conditional splits, right? I'm talking about if your customer opened the last upsell email but did not purchase, send them a follow-up with a different incentive. Little things like that are so powerful by using the behavior and data that's available in front of you. Now, if they did purchase, you should also move them on. I think the worst thing you can do is continue to follow a person's flow when they have already done something. And I know with tools like Omnisend or, you know, any of the other tools, you can identify with triggers that they've made that purchase. You can stop them and And move them forward and you can move them onto a thank you and kind of a next step sequence. You know, I love conditional splits because for me, for instance, if someone's shown an interest in a premium product or bought a top tier item from me before, we can safely offer them a higher tier or a complimentary premium add-on so much easier because the data is right there and you can really drive what people consider that personalized experience of recommendation. And that's really what you're trying to ultimately do. Chase, what do you think about when you think about email structure flow? What are the things that you think about?

Yeah, kind of 2 quick ones to add. I like the ones that you have. I'd say the, the one, the first one for me would be kind of dynamic product recommendations. So using kind of the platforms recommended for you or customers also bought blocks. And again, really making that personal and specific and unique to each individual user. That's fantastic, right? Then people are gonna be able to see item or items that are specific and relevant to them, which is gonna increase the likelihood that they actually convert on the upsell or the cross-sell. And with these, right, like you want these to update based on the behavior of the user. So, you know, the more relevant, you know, the more stock you have and the more popular they are, like you wanna showcase those types of things versus like things that no one cares about that don't sell. You're just wasting space otherwise, right? You wanna take advantage of this digital real estate within your emails for things that you think have the highest likelihood of conversion on a per-user basis. And then—

You know, that gives me a little quick shout out here. You know, one of our pod sponsors right now is Nacelle, and they have a really cool feature Nacelle is doing AI personalization. They are really focusing and honing down on this one segment of the lifecycle, which is the dynamic product recommendation. You should definitely check them out after this pod, of course, but I just wanted to kind of plug that.

Yeah, they're cool. They're doing stuff I've been really impressed by. How do people find them? What— how do people— we have a link in the—

Yeah, we have a link in the bio. It's nacelle.com, but you should go check them out. They have an AI engine that will basically do one-on-one recommended product and they'll even do like the email to landing page to all that fun stuff. So really powerful stuff.

Yeah, they're sick. Definitely check them out. What's up, guys? Real quick, I need just 30 seconds of your time. You already know that personalization is the holy grail of retention marketing. It's that unicorn that we're all chasing, no pun intended. But let's face it, time, resource, and nonstop content changes can make it incredibly difficult for any retention marketer to create real personalization. Well, not until today, that is. I'm really excited to share that the sales new AI-powered product recommendation solution is here. And this AI-powered suite goes way beyond basic customers also bought recommendations. It actually analyzes the entire customer journey. Yes, that's right, from first click to checkout, so you can deliver hyper-relevant experiences to each of your customers. Okay, let me make this super, super simple for you so we're on the same page. So basically, their AI is going to analyze each customer's complete product journey. It's going to create a product collection to automatically push into your email marketing campaigns, which is going to generate a dynamic landing page with those exact personalizations and those exact recommendations. This is going to create a true unified personalized experience at scale, and merchants can transform their e-com store with AI-powered product recommendations that understand their customers' actual behaviors, not just their purchases. So if you're an e-com brand hungry for next-level personalization, you know, the ones that you always hear people talk about, but they don't actually give you a tool to use. Now you have one. You have to check out Nacelle's new AI-powered product recommendation today and let them know that Jimmy and I sent you. Now back to the pod. And then I'd say that the second one, and then we'll move on, is kind of frequency capping. So you also know, while you do want to stay in front of people and you do want to follow up and you do want to stay top of mind, you also want to limit though, like how often you're actually hitting someone with these specific cross-sell and upsell offers. So that way you aren't fatiguing them, right? So there's always a line. I like to straddle the line, right? You don't want to, you know, be too shy of it or kind of over it because if you're over it, you're being too aggressive. And if you're too shy, you're just not sending enough. So, you know, making sure that people don't receive these emails every single time they come to your site, right? Or every single time they open an email, it should be for kind of milestones as we talked about. And, and kind of, I guess, more special occasions than kind of a A daily or a weekly type of thing.

Yeah, no, these are great. All right. But let's not forget about SMS flow structure. Now, look, there's not a ton to add to what you kind of shared because they use a lot of the similar properties. But there's 2 things to add. And remembering that your SMS and email should ideally be echoing and aligned with your email messaging, especially in flows. And of course, remembering if you don't have their SMS, this is the time where you should also be thinking about how can I use that SMS message I would be doing and send it as an email. And just segment against each other. But to me, there's only 2 really important things to think about with SMS flow structure. One, make sure the messages are short and timely, right? Your product is on the way, pair it with blah, blah, blah, use bundle blah for 10% off, right? Like really simple, straightforward messaging because you know that the product pairs really well. You don't want to burn a lot of credits on it. So it's really easy to just kind of add that little blurb. The second thing and something that I think is underutilized in this market ultimately is 2-way SMS ultimately, right? If available, right? If you're using tools that connect to your third party or your SMS provider is also allowing you to have 2-way messages, let the customer reply and ask questions about the suggested products. Talk to them. I think that is such a powerful thing that brands are really missing out on that opportunity to talk to them. And really, it's not hard. And we know that if a customer has made a purchase, they're more likely going to make another purchase.

All right.

Let's shift gears and talk about developing a cross-sell and upsell content calendar, because I know people are hearing us. They're like, okay, I get it, Jimmy and Chase. Like, this all makes sense. I understand that these are important things. I'm going to go work on them. But I want to really dive into what we call the content calendar. And I'm talking things like mapping out your product ecosystem and your goal, how to align your overall marketing calendar, how to define your themes for your marketing, how to push those into automations, how to balance it into evergreen. and time-sensitive frequency management. Let's dive deeper into that. Let's talk about how we should be looking at monthly and quarterly reviews as well. And now kind of give us some examples as we go along and talk about it. I know that's a lot of stuff, but then we'll all wrap it up with how to measure this for success. All right, Chase, you want to kick off the first one, which is map out your product and ecosystem goals?

Yeah. So starting with kind of product mapping. So what you're going to want to do is you want to list out All of your main products. And then again, like the common add-ons or accessories. So the main products and then the things that pair with those products and include also things like premium upgrades and seasonal items. Slide tangent. I just bought my flight to Miami for Commerce Roundtable and I was overwhelmed. But obviously airlines do this better than anyone else with like, oh dude, do I need to buy this upgrade? Do I need to buy this insurance? Do I need this thing that I can get a refund? And I know I was slacking with you and stuff. So I think airlines are just so great at all of these things like upsells, cross-sells, and then just like the psychology. Like I knew the one, I knew the plan and the package that they wanted me to pick, but it was just messing with me so much psychologically. And of course I ended up picking the one that the airline wanted me to pick, right? The best bang for their buck, not mine. So it's just really interesting. And obviously, right, physical products are a little bit different, but Study airlines. That was just an interesting thing that happened recently. And with that, like back to kind of physical products and e-com, you wanna identify which products and combinations make the most sense for cross-selling and upselling at the same time. Like when you, when you sell this, what kind of evolves and exists with this, right? You know, if it's this t-shirt, you know, what are the pants, maybe the hat, the, the bracelet, the accessories that would look really great with this white t-shirt or this black t-shirt or this gray t-shirt? Um, et cetera. Does that make sense so far?

Yeah, absolutely, man.

Cool. And then the next one would be, again, we kind of talked about this briefly before, but kind of setting monthly or quarterly AOV targets. So you wanna decide like for your kind of profitability, for your numbers, for all your metrics in mind, right? So that way you factor in cost of goods, shipping, acquisition costs, et cetera. You know, where do you need and want your AOV to be and, and what's realistic? So, In a given timeframe, right? You know, maybe it's in Q2, Q3, Q4, whatever. I want to increase my AOV by 10% or 20%. And then you use this target kind of to reverse engineer the type of frequency and the offers and kind of the really the upsell package, the cross-sell package and the types of campaigns you need and should be running.

Yeah, I think that I bet you airlines have used so much data to figure out what they can upsell you on, how much of a little bump they can get you to move up on. And dude, they do upsell you like you want the Wi-Fi, you want the mileage, You want this insurance, you want this and that. And I guarantee you all of those on average probably do at least a 10% bump on the person's AOV ultimately of that purchase. So—

100%.

Very, very cool. All right. Let me jump into the next one, which is when you're thinking about aligning with overall marketing calendars. All right. So first of all, look, you know, it's not hard to think about this too much, but you need to coordinate your major campaigns. And what I'm talking about is not just for your email and SMS, but you got to be thinking about this entirely as a business, right? You know, you got your key sales items, your product launches, your holiday promotions on your main calendars, but you should also plan upsells and cross-sells around these events that naturally fit the narrative. So you're thinking about things like holiday gift bundles, new collection add-ons. These are really easy ways to get a person to kind of look at it when you're launching a holiday sale, for example, or seasonal sales. Dude, everybody's looking for the bundle or the set. I mean, we could go into a physical store and, you know, you come to buy perfume for your wife. They'll always tend to be like, well, you can buy perfume or you can buy this bundle set for $10 more and it's going to include a free towel or whatever it might be. The perceived value is so strong there and people just like to do it because they're also looking for higher perceived values on those different purchases they're making. The same thing with new collection add-ons, right? I'm buying a new collection. I'm hyped on a new product purchase. Well, then I'm going to want to really push on that. Now, if you're sending a promotional blast on Monday, here's some things you want to start avoiding. Time of cross-sell and upsell, you should be preventing oversaturation. What I mean there is don't try to overlap the messaging too much, right? I know your narrative in your mind is I need to sell them as fast as possible, but reality is you've got to give it time and you want to make sure that you're integrating it together with your existing stuff rather than trying to create separate emails on everything. And what I mean by that is simple. Let's say you're doing a product launch. Your first email may be the big promotional announcement. The second one may be the promotional announcement with a collection add-on that you've thrown in there to say, here's the product that we've been emailing you about. By the way, we've got this collection version where it's this product plus some of the collections of our best sellers or whatever it might be, or add-ons or accessories that are really good. Let's go ahead and put them together. So you should be using those messages and trying to upsell them in real time. I almost call this like a pre-purchase upsell where you're really getting them to buy in on a bigger package. That's really the narrative you want to kind of build. All right. Let's talk about themes a little bit. I think that was the third thing on my list.

Yeah.

So with themes, right? Like you want to try, if you can, every month to have some kind of theme or focus product. So in January, right? You might emphasize the whole new year, new you, the whole upgrade type thing. While February could be like a Valentine's accessory bundle. So every month kind of naturally leads itself to some kind of overall theme and therefore maybe product focus or product bundle. And then with that, like each theme really needs to make sure that it guides your store and guides kind of your marketing, guides all your efforts towards the products that you're gonna upsell and cross-sell in your automations. And you should have all of this being kind of cohesive. Now the ads, the website, the emails, the SMS, the push, they all are working together each month or each quarter or whatever the frequency is. To push the same types of bundles or products. So that way you really can get those nice cross-sell and upsells in place. You just kind of have the messaging really congruent across the board. And then also too, right? Like, and as you think about like these monthly kind of themes and these focus products, you know, tying in seasonal and trend-based angles is super important. So in the event that maybe you're kind of selling fitness products in January, you might wanna focus on selling kind of an upsell into a higher-end workout gear because people are really motivated, incentivized to do the whole kind of new year, new me, put the best self forward. That's really top of mind for them. You know, health is a really big priority, whereas kind of a beauty brand might push kind of complimentary skincare items during dry winter months, right? Hey, when you buy or you spend this much, we're going to toss in, you know, these types of products complimentary, right? Or, hey, when you buy these items, we want to kind of toss in this new product that we've been working on or whatever it might be, trying to get people to spend more money with your store, either through paying for additional things or through pushing the bundle thing and then them getting a freebie because it's kind of baked into the cost that you're, that you're selling already.

Yeah, that makes total sense. And I love the thought process of really being seasonal or creating trends or I guess like themes ultimately, because really it's what people want. People want a theme and they want consistency behind that theme. And that's what you end up driving when you have a good theme. In fact, when you think about the next point here that I mentioned is talking about automation touchpoints, and we've talked about this with Omnisend's recent report of different things, dude, automations are like the forgotten stepchild that is happening right now.

Yeah.

And for me, my next point here is all about updating your automation touchpoints and you should be doing this I think every 30 days ultimately right now.

Yeah.

Here's some of the things you should be thinking about. Your pre-purchase automation. You've got to be thinking about your cart abandonments and your browse abandonments. You should be scheduling variations and cross-sell recommendations based on current promotions or seasonal bestsellers. In the holidays, your cart abandonment should be really based around what you know sells in the holidays versus in the summer, sell bathing suits. In the winter, sell coats, right? Don't try to sell bathing suits in the middle of the winter even though they're your best-selling product because Well, it's not really seasonal or theme-based, right? The same thing kind of happens with post-purchase automations. I'm talking about order confirmations and thank you flows, inserting timely add-ons with premium upsells on these messages, updating monthly with fresh offers or the newest products. Dude, you got to be thinking about that. And same thing even goes down to your delivery and reorder reminders. You talked about lifecycle earlier. When you're thinking about lifecycle, these should be all recommended seasonally. So every month things are changing. People are buying, especially if you're an apparel company, for example, For a, you know, for example, like a fitness company, for example, in January, I'm probably talking about fat loss and weight loss, wherein summer I'm talking about toning up, and maybe in this wintertime talking about bulking up and getting stronger, right? Those are different upsells that you've got to be putting into your automations. And too often brands are forgetting to put these upsell changes that are happening, and you're really losing money on the table and losing AOV opportunities. So if you're a retention marketer listening to this, this should be your note. This is what you should be focusing on. Yeah, you should be optimizing, you should be looking at the data, you should be looking at that. But the way you optimize for dollars and revenue is to really drill in and look at what you're recommending at the post-purchase and pre-purchase stages and really driving and focusing on not just your best sellers, but products that are relevant and seasonal and, you know, things that people might buy today. In fact, that kind of leads us to evergreen stuff. Talk about that to me.

Yeah. I love what you said. The next part is like making sure that you're balancing kind of these evergreen offers with more time-sensitive promos. Right. So again, we talked about having things monthly and having things based off themes and whatnot. It's great to have evergreen as well that you could run year-round or kind of quarterly, whatever, but you also want to have things that are time-sensitive. So with kind of the evergreen content, let's focus on that first. You're going to want to have certain kind of cross-sell upsells, like you know, your classic accessories, let's say, remain relevant all year. And you're gonna wanna keep these kind of in your automated sequences, but you do wanna update copy and kind of refresh images and kind of some of the messaging periodically. That way it's still fresh and relevant depending on what you've learned, what's changed with your customer, those types of things. You don't want it to be the same thing evergreen from 4 years ago. It's great to find something that works, But you do need to kind of add some fresh paint to it every once in a while so it doesn't go stale. And then on the other side of that, right, while that's super important to have evergreen, you do need and want to kind of have these more time-sensitive flash offers. Again, these are kind of more short-term in nature. They're not gonna be evergreen. So they're gonna be having a fixed amount of time kind of from start to end where, you know, the beginning and the end date upfront. So that way, kind of with this, they kind of coincide potentially with holidays or new product launches. And you can add kind of this urgent language within your email and your SMS messages that's, hey, upgrade in the next 48 hours for a special 10% discount. And with that, right, this plays more into all the psychological elements that are so important to getting someone to actually take an action. Because sure, the evergreen things are great, but if it's kind of an open-ended thing, there's no real need to do it today. Whereas with this time-sensitive flash offers, it is get it today or tomorrow or miss out on it. And people hate missing out.

100%, dude. I love that because if you think about it, right? When people run a special weekend sale, they don't think about their automations. They just think about setting up their campaigns. But the reality is you've got to set up everything. And when we talk about campaigns, it's not just your campaign, it's your campaign plus your automation that kind of work one and two together. All right. I know you're enjoying this pod, but I wanted to stop you just for 30 seconds and tell you about something very special that Chase and I have been working on. Between the two of us, we have over 20 years of experience in email marketing, and when we And when we teamed up to do this pod, we realized we had even a bigger opportunity to put our minds together and create a certification program that takes our 20 years of knowledge and share it to the world. And that's why we created Ecom Email Certified, an end-to-end course and certification program that's designed to take anyone, regardless if you're a newbie to an experienced marketer, founder, executive, agency marketer, or any other marketing professional, to teach them everything we know about email marketing. Yeah. Email and SMS marketing. From deliverability to AI to copywriting to design to strategy, we cover it all. It's loaded with 175+ modules, 25 hours of education combined with quizzes and community, all designed to educate, test, and certify you as a full-fledged email marketer for e-commerce. And since you're listening to this pod, we want to reward you for your loyalty. So we're going to give you a coupon for $100 off this certification. Jump over to ecomemailcertified.com. Use coupon code SENDIT. That's S-E-N-D-I-T, no space. Join our certification program today. Now back to your pod. All right. The next point that we have when you're thinking about getting tactical here is the frequency management and channel coordination. All right. So there's 2 things you want to, of course, coordinate across email and SMS. But let's start off by avoiding the overwhelm, even though you're excited about boosting your AOV. Spaced out cross-sell and upsell messages are super crucial. You can't be in front of them too fast. And if you're not using the same platform for your ESP and SMS, this becomes even more important because the last thing you want to do is to have 2 different platforms sending a message, the same message in a really tight timeframe where people are feeling a little bit more pushy than they are really being upsold or curated or narrated through, kind of guided through that purchase, right? And that's why it's so important to coordinate across your email and SMS platforms using SMS timely, right? We talked about now and in the time. It's about creating immediate nudges. And email is more detailed where you're doing like product education and bundling and all that stuff. So make sure you're staggering them. On first day, you might send an email first and let them know about this upsell opportunity or this cross-sell, then the SMS a day later to reinforce that message without bombarding. I know it sounds really basic, but I see it all the time. I make purchases, Chase, from some of the biggest brands, and I'll get hit the next day with Thank you for order. Here's an upsell product. And at the same time getting SMS for either this campaign or the same product. And it feels very redundant without feeling like they're kind of narrating and guiding me down the kind of customer journey ultimately. All right, Chase, when you're thinking about this, the last point I mentioned was really about getting down and saying, okay, now how should we be looking at it? What should we be reviewing? So tell me about that.

Yeah, I think one of the big things that people fail to do is they fail to review and therefore they can't really make adjustments on the fly. So every month, every quarter, you really need to be kind of reviewing and auditing and then therefore finding kind of the opportunities to go implement of the data that you have, right? You have all this data, you might as well do something with it. So step 1 is check the performance. So compare your AOV and attach rates before and after implementing each campaign and really identify which of the cross-sell or upsell offers So, right, with the goal of kind of this whole episode and the goal of all of this strategy being increasing AOV, see if on a monthly kind of quarterly basis, are you increasing it? Is it staying the same? Is it, is it getting worse? Like what, what is happening? And if it is working, what's working, right? What are the offers as mentioned that are actually moving the needle and how do you go do more of that? And then the next one, right, is like as you review that data, You're gonna wanna make these refinements to the products that you're suggesting. Maybe you're just not moving the needle and it probably could be your recommendation engine. Maybe you have the wrong tech, maybe you have the wrong pairings. You know, maybe things are just like outta whack, right? Maybe they're, maybe something broke. You wanna basically make sure that you're swapping out kind of these low-performing items or bundling strategies for something that could or should be working better. And keep an eye on your inventory to make sure that you're not recommending things that are outta stock. That might be why you're not moving the needle. Maybe you're recommending something that people wanna buy, but they can't buy it cuz you've got no units in stock. That happens a lot for popular products, right? And then the last thing is kind of gather this feedback. So look at your unsub rates, look at the open clicks, other types of engagement behaviors, and see if you're pushing too hard, if you're pushing the right amount, or maybe you're not pushing hard enough, right? And then with this, maybe consider adding like surveys or kind of Forms so you can get feedback on are these reviews and recommendations helpful or are they not?

Oh, that's beautiful, man. I love, I love that thought process when especially that gather feedback thing. Dude, customers don't mind telling you how they feel about things and it's the best thing to ask them. I mean, you got to remember there's a real, a real human behind that keyboard and for, or that mobile device and your job really is to kind of drive that question. All right. Let's get a little practical here. Now we've kind of shared the theory and understanding of how things go. I'll kind of tell you about 2 different things that I'm thinking about, and I think you can kind of help us kind of hone it in with how you can kind of take it.

Okay.

So let's talk really big picture first, right? We're thinking seasonal, right? When you think about seasonal bundles, I can, I can kind of name you some examples. So in Q1, if I'm a fitness company, right, I might say something like New Year, New Gear, and my upsell may be from basic equipment to premium equipment, really taking the same thing they're purchasing and bringing them up because Everybody wants the newest and freshest and the best for themselves. Or if I'm a wardrobe company, I'm a fashion company, I might go spring theme and say, hey, refresh your wardrobe, right? Everybody wants to look fresh for the spring. Something about us as humans wants to go out in the spring into the summer and always look fresh with the newest clothes. That's kind of due. So cross-selling or cross-selling for different fashion stuff inside of your wardrobe by refreshing is a really good one. And then in the summer, people are traveling and they're on vacation. So in Q3, I'm thinking about summer travel accessories for my luggage or my clothing store. Really simple ways. And then Q4, to me, one of the things that I've seen over and over again that is working really well is holiday gift bundles. Everybody loves bundles. All you got to do is take your bestsellers, put some stocking stuffer accessories together, and suddenly you got a bundle. You can charge just a little bit more and you can just get people to buy more, right? These are things that I think about. Chase, what do you think about those?

Dude, I love that. I love that. And one kind of thing that came to mind for me, kind of as I guess the next one is the rotation of promotions, right? So as you're talking about seasonally, kind of from Q1 all the way through Q4, going from the new year vibe to the spring, the summer, the holiday, et cetera, you know, you need to have a schedule that you build and you keep. Ideally you're planning well in advance, so you know what that looks like, that kind of rotates. So each month you refresh the recommended products in your post-purchase flow. I know it sounds like a lot of work, but if you do this, it is gonna increase your conversion. So the work is gonna be granted and, and worth it. And this really makes sure that when people do buy time and time again, they are seeing new and relevant kind of cross-sell offers each time. I mean, that's one of the best ways to avoid fatigue is if you just keep hammering the same offer every single month for the entirety of the year, and you're, you are including people that purchased this in the past, you're just gonna burn them out. It's nothing new, it's nothing different, it's just the same. Whereas if you do rotate things, you can get away sending to people that have bought recently because it's a new offer. It's a new product. It's a new upsell, whatever it might be. It's gonna be fresh.

Yeah. No, I love that. And if you're a retention marketer and you're, like, thinking about this and you're asking, okay, well, how do I map this out? And I'm thinking about it a little bit more deeply and I wanna get really core into the nitty-gritty. Here's an example I'm thinking about. Alright. So week 1, we might launch a new product with an upgrade upsell email. Alright. So We launched that product, we're promoting it. On week 2, I'm taking those cart abandonments and checkout flow abandonments, and I'm automatically referencing the new product basically. So I'm adding that new product into my checkout because it's the new upsell product that I'm putting out in the market, right? And then in week 3, I might take an SMS campaign and take that product and bundle it with a good complementary bestseller that I know people buy often and bundle the new product, really getting it out there and continuously talking about it. Without just pushing that single product. And then the last week, I think this is something that I love. You can either use social media, you can use your blog, you can use your vlog, whatever video or anything you're doing, or you can just send an email featuring the success stories of that new product and continue to promote not only the new product, but related products to that. Because really it's about mapping it all out. It's being about methodical and mapping out your cross-sell and upsell ideas on a content calendar and syncing them with your automation flows. And creating a real customer journey, man. So brands that take this approach can steadily increase their AOV without delivering— while delivering a consistent brand experience and it's relevant for people each and every month. Like that's all it really is. That's to me, a well-defined customer journey is when every part of your funnel, including your automations, including your campaigns, including your social media, including all those different pieces work together really cohesively and they feel like They're meant to be there because, well, they are, and that's how you should be thinking about it. All right, Chase, we went through a lot of stuff here. Let's talk about measuring this. What are the things that you should be thinking about when you measure? Because I don't think it's just AOV. I know that's important, but what else should we be thinking about?

Hey, it's Chase, and I hope you're enjoying the pod. But if I could just have 30 seconds of your time, I want to tell you about our special friends at Omnisend. Omnisend is an all-in-one email and SMS marketing platform built specifically for e-commerce brands. They make it super easy to engage your customers, drive repeat sales, and create those seamless personalized experiences that we're always talking about on this pod. And one thing that I love about Omnisend is they're trusted by over 125,000 e-commerce merchants around the world, and their users absolutely love them. They have a 4.8-star rating from over 5,800 reviews on the Shopify App Store. It's an obvious choice for your email, SMS, and push needs. In fact, I'm actually in the process of moving over my own email newsletter and some of my clients, and they have been fantastic. Their support and their platform has been amazing, and there's tons of features, and it's been surprisingly very easy to use. And the whole migration process, I know it sounds daunting, it's actually been a breeze. It's been way easier than I could imagine, and their team has really carried a lot of the weight of that migration, and they'll do the same for you as well as they have a great automation tool that are going to help bring over your contacts and all your other important data that you need. And they aren't raising any prices, right? They're not going to raise prices like you— on you constantly, like some of the other ones. You know who we're talking about and call them profile-based pricing alignment. Really fancy term that no one means, but Omnisend is not going to do that. They're going to speak the language that we speak. They're not going to raise prices on you constantly. So if you're looking to take your email marketing and your SMS marketing and your push to the next level, I highly recommend that you check out Omnisend. They've got the tools, the automation, and the expertise needed to help grow your brand So you can ultimately thrive. Head over to omnisend.com/sendit to learn more and start scaling your customer engagement today and let them know that Jimmy and I sent you. Now back to the pod.

Yeah.

So starting with AOV, and then I'll talk about a couple others. Number one is the AOV shift, right? So the average order value shift. So again, compare the baseline before implementing these new flows and these new strategies to after and see is it working or is it not working? The next one would be kind of the attach rate. So basically kind of the percentage of orders that added the recommended accessories. Or the upgrade. So what is the percentage of people that actually are, you know, taking your upsell or your cross-sell? The next one is conversion window. So how long after receiving kind of these messages do people typically purchase? And you're gonna wanna adjust your timing based on these insights. And then the last one, kind of quickly going through all these, I know would be, of course you need to be A/B testing these products. So test different kind of recommended product sets, different offers, different copies, different angles. Just to see what works. And again, don't forget to monitor unsub spam complaints, those types of things as well, just to see kind of what's happening. 'Cause you're gonna be a little bit more aggressive with all of this. Our users, our customers, our subscribers, are they liking and kind of engaging in a positive behavior or are they disliking these types of things? And you'll see from their actions. And then kind of lastly, Kind of one quick kind of hot tip. Don't forget, again, I know I just mentioned this, don't forget to watch your unsub rate because if you are being aggressive with this, you know, it is something, right? That like you wanna be mindful of because now kind of unsubscribes and marked as spams, they're just so much more important in the world that we live in today with, you know, Google and Yahoo and certain providers being a lot more strict with kind of some of the negative metrics.

I love that. So here's what I heard. Make sure you don't want to over-segment or too many segments can lead to confusion, right? That's number one. You don't want inconsistent inventory. You want to recommend— not recommend out-of-stock products. You want to make sure that you're not frustrating the customer ultimately, right? You also don't want irrelevant recommendations, pushing random items that don't really relate to the person. If I just sold you a weight loss pill, I'm not going to send you a You know, a muscle gaining pill at the same time. They're irrelevant and that really kills trust. And then last but not least, it's really spamming, right? Being too frequent and bombarding your customer will erode your customer quality. Like people won't trust you because you're telling them things that they probably don't care about and you're probably just sending messages and it starts to feel a bit desperate. So there's a fine line behind all of this stuff. Chase, this has been a great episode, man. This has been truly a masterclass when we're talking about this stuff. Let's do a recap. You wanna recap the 5 takeaways that you heard here today on today's episode?

Yeah, of course. So 5 kind of key takeaways from today's episode. I hope you guys got obviously a lot of value, but 5 of them. So number 1 is map your products for logical kind of cross-sell and upsell paths. Number 2 is you wanna use timing and triggers wisely in these automations. So consider pre and post-purchase, kind of what makes sense when and where. Number 3 is you have to build smart segments and dynamic recommendations so that way the offers are personal to each individual person. Then, okay, as with any campaign, number 4 is you have to measure and refine with your KPIs and the use of A/B testing just to figure out, you know, how are you performing and how do you continue improving? And then lastly, avoiding kind of common mistakes and pitfalls like Irrelevant recommendations and spammy frequency. Again, don't hammer people too hard. You want to find that right frequency where you're driving revenue, but you're not making people upset.

That was great, man. That's a good recap of this episode. I feel like there was so much we went over here today. And, you know, to me, being able to talk about this, not only exciting, I'm passionate about this stuff. I think there's so many little things that retention marketers often fall into the gap of thinking about just campaigns and They'll set up your basic automation flows, but all of this stuff is what you should be doing on a day-to-day job. I was just on a call and someone MentorPass recently, Chase, and they were like, well, what do they do besides send a campaign, you know? And I was like, oh my God, my friend, there is so much you're missing out if you think that a retention marketer, or if your agency that you have is not thinking like this and they're just purely sitting there and sending these campaigns, though it may be holiday-centric or whatever it is It's definitely things you've seen. And I'm sure you've seen that too, right, Chase?

100%. Yes.

Dude, that's crazy, man. It's wild when people start to do it. And hopefully people have listened to it and gotten this far, really opened up their mind. And you can take one thing away, as simple as taking advantage of checking your automations and updating your product flows, or getting really strategic and starting to unlock and realizing you as a retention marketer, it's not just about making that second purchase, but it's about increasing the value of that second purchase, increasing their AOV and getting more money out of that same customer. And it's not really a bad thing if you're doing it with good intent and purpose. All right. So if you enjoyed this podcast today, please make sure you like, subscribe, follow, leave us a rating on your favorite listening platform. You can follow this show on X, LinkedIn, YouTube, IG, TikTok, etc. But we're mainly found on YouTube and that's where you should come check us out. A lot of times we're sharing things on a screen, plus you get to look at our beautiful faces too. And there's a few ways to connect with us. First, you can encourage us— encourage you to join our newsletter at ecomemailmarketer.com. We drop newsletters about retention every day. I think we're doing it 3 times a week right now. Link in the show notes. Secondly, if you enjoyed this topic, you enjoy the things we talk about, and you want to learn more about retention marketing, well, we've got a brand new certification course. You probably heard the little episode commercial that we had. But if you fast forward and didn't listen to it, well, I'm going to tell you about it one more time. It's 25 hours of training, includes a full exam, gives you certification to proudly present on your social media, use it to get a new job, or even ask for a promotion. It's found on ecomemailcertified.com. Use coupon code SENDIT, all one word, and get $100 off your certification today. And last but not least, let's make sure you follow us on social because we share all these wisdoms and tips, tips every day on social. Chase, where can we find you on social?

Most platforms, Chase Diamond, O-A-N Diamond.

There you go. And the man is found everywhere. And I'm found mostly on X and LinkedIn here today, though I might go jump into more. Now, look, Chase, next week, because this topic spurred up so many conversations around personalization, well, next week we're going to bring in a special guest, Brian Anderson, CEO of Nacelle. Remember I talked about it earlier about personalization and how you can take that main important point and drive a true one-on-one personalization? Well, we're going to talk about it because they're launching this new personalization using AI because that's really important to us and we love AI around here. And they are going to help you create an Amazon-like experience for each and every customer at scale. We're going to grill him about the tech. We're going to learn about what he's been working on. We're going to talk about results. I'm super excited about that. Hope that this one's going to be a really good one for you guys. So hope you tune in for that one. With that, 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.