Email Deliverability with Jimmy Kim and Chase Dimond

Introduction: The Importance of Content Engagement

0:00you're getting things delivered people are opening them but they're just not engaging it's your content dude basically it's the one variable that we have left to mess with right people are receiving the emails they're opening but they're just not engaging it's your content your content is not meeting their needs right like we can't force someone to click people have their own free will so you have to make that your audience can resonate with your message right you know that can happen through solving their problems right so even if they're not engaging on the CTR level as long as it's engaging enough where people are reading it and enjoying it you're still doing a service to your score and your reputation rank so it's not terrible newsletters are very much an example of this right we send a newsletter out for example and there's a lot of text and not a lot of clickthrough rate options there and sometimes we don't get a lot of clickthrough rate but we don't see a decline in our deliverability or our

0:47engagement because we know the value of the content is being engaged inside the email and it doesn't mean that it's always coming out on the other size of Metro hello everyone excited to be here

Welcome and Introductions

1:01what's up Chase how are you dude good how you doing I'm good man let me go ahead and pull this thing up so we can get this thing rocking enrolling here today very excited everybody here today looks like you guys are all engaging and we love the engagement you guys are providing here always love a good engaged group I'm going to go ahead and pull up my slide throw in slideshow mode and get this show on the road let me go ahead and hide Nick here so that he's not there there perfect okay cool all

Email Deliverability Masterclass Overview

1:29right guys well with that since we saw so much great information here from Greg and Brian so far we're going to go nerd it out even more and we're going to jump over into email deliverability Master Class what Google doesn't want you to know in 2025 so we're going to go back and forth got a lot of information to share of course the deck will be available at the end because we're going to go through a lot of information here excited to go through this with you guys all let's get started so first things first who am I I'll start with introducing myself my name is Jimmy Kim for those that don't know I have been in the email and digital marketing world for over 17 plus years now I'm a former DDC brand a Peril owner I turned into the SAS founder and today I do a lot of media I'm a podcast host email SMS expert and if you didn't know the Commerce Round Table is actually presented and started by me and my

2:20team and we are here with Shaq and I today to be able to present this to you on our digital experience and then we've got our live experiences well I know Shaq is going to be giving away a couple tickets at the end of this event for our Miami event which is in April 25th and then of course our San Diego event which is our big event in September as well other things I do I do the awesome pod which is a a show by perspective and then the send it so if you love retention you should 100% check out that podcast that's Chase and I and chase you want to introduce yourself what's up everyone soak to be here this chat is just insane so I appreciate the the energy I'm a self-proclaimed email marketing nerd I'm a partner with Nick who is our gracious host over at structured we've done over $200 million in email tributal revenue for our clients I was recently named by Shopify as the number one Ecom

3:09influencer to follow which was very very cool so very grateful for that and then I've built multiple agencies I had an Ecom brand in the past and I've been an adviser to some fast growing Ecom SAS so let's get into the agenda all right

Why You Should Care About Deliverability

3:23well we've got a beefy agenda here today we've got five things we're going to go over here today we're going to start off with why you should care about deliverability I know you've probably heard it but we want to explain to you what we think and what we believe we're going to go into how you think deliverability works this is how most people think and then we're going to do a deep dive of how deliverability actually works and this is where the eye opening part really gets into place and then we're going to leave you with two very tactical sections to this one how you what you should do to get better at deliverability think best practices things that you should be thinking about and then we're going to get really focused into 10 tips that you should be doing into 2025 so let's start off with why should you care about deliverability so Chase why should you care about deliverability yeah well it's a good sign that you guys are all here cuz that

4:07means you guys all care but for those that maybe aren't familiar there there's a couple things so number one is it's like the whole thing of a tree falls in the forest and no one's there to hear it does it make a sound the same thing's true with email if you send an email but it doesn't land in the Inbox and it's in someone's spam does it really matter what you write did you actually send that email very very few people are actually going to be able to engage with that where you're going to waste a lot of time and waste a lot of money that's number one number two it is like the one thing that you can do that will dramatically increase your bottom line if you can get more people to actually receive your emails therefore more people in theory can open it and then click and then make a purchase so it is the single most important thing within email marketing as a whole making sure that your subscribers your

4:55customers your prospects are actually receiving your emails and then with that right kind of related to the above you know for those that are running paid media right with e-commerce you have to really run paid media these days to do well I'm sure maybe you can have influencers or kind of Tik Tok shop type thing Affiliates but if you're running paid media and you can't get people to engage and see your emails all the money that you're spending on top of funnel is going to be wasted you're leaving money on the table by not being able to communicate properly with your list and I guess the last two things is you know this is something that g and I hear a lot Jimmy as a former kind of ESP owner himself you know we do a lot of work with omnisend you know today this is something that a lot of people think omnisend and other esps are responsible for and sure they provide great tools they provide great visibility they provide a lot of great stuff but at the

5:47end of the day the deliverability you know responsibility is in your hands as a brand owner and more importantly as a marketer and with that for anyone that's not focused on deliverability anyone that's not paying attention anyone that's batching and Blasting and doing all the things that you're not supposed to it's going to be a really tough wakeup call this year because there are a lot of things that have changed and it's only going to get harder but good news we're going to talk about how to do all the right things today absolutely Chas so let's talk about it I think one

How Deliverability Actually Works

6:15of the things that have happened as you zap forward through the last 20 years and we look at the evolution of what's happened with email and everything first things first we talk about the promotional box right everybody's thinking about the tabs iOS 18.2 just rolled out where even the iPhone I know ped for a while but we'll pretend that it's brand new in this world but iPhone even rolled out a tab system with inbox and Promotional and social and different things that are in there we also saw an evolution of spam traps and providers right if you don't know what a Spam trap is it's an expired email it's a seated email these are bad emails that are out there floating around and the whole idea behind him is to catch people who are sending emails that are unwanted we also sell isps which are your internet service providers like Gmail AT&T Yahoo and all these different people start to evolve and get better and start working on their technology again we'll talk a lot about that a

7:09little bit later we also saw the evolution of algorithms right we saw things changing we saw dmark and dkm d SPF all those new things that are coming into place but all of those come with a change in the algorithms that are occurring in this market we saw this thing we call an early reputation reset if you did not know some of the providers like Yahoo Verizon and AOL for example every year they're resetting your reputation to make you start fresh in the background and those who are doing a great job today probably have not felt it but people who are shaky or on the gray area on the cusp are often feeling these changes occur and the last thing as you guys all know AI is here and AI is changing everything once again it's making algorithms better making spam filters better it's making things easier to do but also harder to do at the same time which is why deliverability is on the Forefront of this as Chase said if those emails

8:03aren't getting into it so Chase why don't you break down how most people think deliverability works yeah so I'm going to break down kind of a really simplified version then Jimmy's going to actually break down how it actually works so I think most people think it's as simple as you select your audience so you pick some kind of list or segment then you create your content right you write your plain text or your designed emails you then press send and then it magically is going to go to the Gmail the Yahoo all of the different providers and it's either going to hit the inbox or it's not going to get delivered and if it's not delivered in the case that maybe it goes to spam or gets blocked you're going to go oh man I hate my ESP you know you're going to start blaming them you know so and so you guys suck you guys suck whereas really again as we've talked about the responsibility and the power of all of this deliverability is in your hands as

8:55marketers so you know you have to follow best practices because it's so much easier to prent prent going into spam versus once you're in spam you have to really claw and dig your way out it's going to be you know 10 times harder so follow best practices that we're going to talk about to make sure that you never get into spam Jimmy will you share how it actually works no Absolutely I'll tell you how deliverability actually works we're going to break down Google because that's the most exciting one so just like Chase said you're going to start off by selecting your audience and creating your engaging content that's number one and you're going to start sending it we're going to use on Gmail today and we're going to pick on them just because it's the easiest but what happens is once it gets to Gmail right there's a transfer of information it's a packet of information your email your HTML your links everything gets transferred to Gmail the first thing Gmail does it starts scoring the first

9:42thing it does is checks your technical setup does it have the IP the dkim SPF then it goes to the next later and checks your domain and looks at the reputation behind it then it looks at your subject line your footer and your images and it starts to check out and ensure that these are relevant important they don't have the spammy Q worth they you know they good information points then it starts looking at your links and this is something that's pretty interesting that we see actually happening they're actually digging into your links and your link reputation behind it something we've seen in the past is if you're sending to a link that has a poor reputation on the web and it has nothing to do with your email it could still get you scored into the wrong place so they check your first link your secondary link your final destination link and even your landing page link and last but not least it does check your is ESP IP and reputation though that is a little bit less

10:31important today now continuing on after it scores that what happens is then it starts scoring your website and this is something a lot of people don't understand or don't even know but one it checks if you have the two things terms of service and privacy policy so if you don't have that for some crazy reason right now you need to make sure you have that on the end link of your domain web website secondly you've got to make sure you've got your reply address right if I hit reply is it a real inbox is it a real place that you can go I know big companies will do the whole no reply thing that is not good for deliverability that is not something you should do as important secondly it also looks at your web analytics right you guys all use Google analytics or some version of it you guys hook up your things to Google it's reviewing your traffic and making sure you're doing real things on the internet it checks against your IP and volumes this is

11:19important too if you go from zero to 100 today meaning if you go from 5,000 emails to 20,000 emails tomorrow it's not going to like that because it's looking at historical data behind that and then of course last but not least it starts to check against the content links against spam networks with Google they're looking at spam hos specifically but every provider has a different one in fact if you look at all the networks they all have a different Alliance Yahoo has spam hos they've got their own internal Hotmail is actually using proof point and Barracuda along with Spam house so they've got a lot of things around it Apple's and other proof point one they've got their own homegrown system Apple Mail also has their own homegrown and and Outlook of course has spet vade OTP so these are all alliances they're making where they're basically relying on third parties to give them spam spam information and now that's not super important in that you know about what they do you just need to understand that

12:13there's so many things in moving parts that are occurring as you're scoring your email and so we continue to go on and then it goes into either the inbox or the spam or junk inbox and what it's doing in real time as it's getting delivered is it's starting to look at these signals these are the the eight signals that they're looking for a are the emails being received going to a valid email you know what a bounce is Right a bounce is when an email is rejected because it's not a real email address right so that's the first thing it's starting to check and score the second thing it's starting to check and score is are these emails being received by a Spam trap so these are seated or bad emails that the isps are putting out there and they own and their whole goal is to catch people who are buying or selling lists and also to capture people who are tapping the list like 10-year-old list where they're trying to bring into the into the picture are the

13:02same accounts clicking on every email or every link you know I know there's all these Services out there that will open and click your link unfortunately isps are smarter than that already they already know what's going on and that's something that people are starting to look at has the email received an email in the sender from the past so they look at historical actions right is it the first time you've received it or have you been receiving these emails these are scorings does the reply address work I already talked about that but they're checking that in real time each and every time it's checking your spam trigger words that are being used not I'm saying that it's bad I'm just saying that they're going to check it they want to know that you're not over there sending something truly spam and there's plenty of things that are going in and this is where AI comes into place it's looking at subject lines is it clickbait meaning are people opening clicking and deleting it and all that

13:48stuff and then they last but not least they're looking at is this cender a person is it info is it support it's trying to understand and identify the user on the other end and from there and we're continuing on still does it starts to react to that email it starts to look at the thing the number one thing you'll notice on this list here is it does not care about the open Google itself tells you on their own documents and forms they do not track or look at opens what they do track is very simple do they click do they reply do they share that means like forward to a friend do they remove it from the box spam folder do they read it and for how long do they forward it off do they trash it do they archive it do they click spam was the email wanted that's ultimately what people are trying to understand right they want to make sure that as they're getting these emails and how those things are reacting what happens and

14:41then the magical thing happens again where they're inboxing and spamming so this happens all in real time and one of the weird things that I've seen over time is when you see an email go out sometimes an email will land in your inbox and it'll magically disappear and you'll go off and look for it and can't find it you'll end up going to a Spam box and find it there any of you guys ever have seen this actually happen well I bet you have because it happens all the time because an email has a low quality score it's actually pulling people out from that email so that's something you got to watch out for this is how Google actually is doing in real time and this happens it's just a matter of seconds that's happening in real time and this is what's happening not with just Google but everybody some of them more stringent like Microsoft or or apple those guys are even more stringent with the process with this but this is the rudimentary but not so rudimentary

15:32way that their intelligence Works to score the filter and decide if your email is valid good and wanted by other people awesome and and with that right

Understanding the Promotional Box

15:41one question we get a lot is well what about the promotional box right what about the promo box isn't that spam and the reality is no it is not spam the way they think about it too is like each kind of folder that you're in has you know potentially an Associated range of open rates if you're in the spam folder you're going to see you know low singled digigit open rates maybe one to probably Max of like 5% in the promotions you're probably going to maybe see slightly lower than the primary folder but it's still a really great place to be and when you think about the promotions tab when you think about like Google for example they have designed these tabs so that way not everything is cluttered in the primary folder could you imagine if like spam and promotions and social and the primary stuff was all in the main folder it just doesn't make sense so essentially what they did is they've designed the promotions tab for marketing emails and its purpose again

16:36as mentioned is to separate it from other content and kind of going to the next point this sorting is based on user Behavior so depending on how each individual person on your list engages with your emails will depend on kind of where they they fall so for example if you're you know primarily in the kind of promotions folder but someone's engaging with the email say on Gmail they're opening they're clicking they're forwarding they're reading it you know if they're doing that time and time again there's a chance that Google might be like all right these people actually want this this is something that they really care about then it might move to the primary right or for whatever reason if you're in the promotions and people don't really engage you'll probably you know stay there type of a thing and then you know if they don't engage for a long time and you keep mailing them you know maybe you'll end up in spam so it just really depends on what someone is or isn't doing and then

17:27with that right like the design of your email does affect deliverability it's not the only thing I think a lot of people are like I have a single image email or I have images within my email does that mean I'm automatically going to be in spam or does that automatically it doesn't mean automatically but it does carry some weight it doesn't carry the entirety of the weight like Jimmy talked about there's a lot of different factors but yes the design and the structure of your email can impact placement so emails that seem like overly promotional so if they have a lot of images tons of buttons tons of discounts that's going to come across to you know Gmail Yahoo and the others as you know a promotion whereas if something is more kind of plain text if something kind of feels a little bit more personalized in nature you know maybe it's going to be more likely to be you know potentially the the primary folder as well right and then with that the content quality that you guys are

18:19going to be focused on and building out is super important the content within the email does matter a great deal so emails that are super salesy and super Promotional and maybe even super spammy like they have free all over it and they have all this language that's like limited time and there's tons of links and the links go to different places you know that's not going to be something that's likely to ever be in the primary that's something that's going to more likely be in the promotions and again depending on other variables could potentially be in the spam but but again focus on the content don't make it spammy and then you should be in the primary or the promotions and I guess the last thing to kind of talk about here as I mentioned before it's it's not dependent on your ESP right like you know if you use one of the top esps like an omnis for example or like a clavio or others you know and you're following best practice and you're doing these

19:05things you should be in the primary or the promotions you should not be in the spam you're going to be in the spam if you abuse the systems that are set up and your emails are basically doing you know all the Opposites of what we're talking about you know they're spammy they're all caps they've got tons of emojis and we'll talk a bit more later about like all those specifics and then I was going to say do you mind

Improving Your Deliverability

19:27telling us like how do we get better at this yeah so let's talk about deliverability a little bit well first things first Chase if I asked anybody and I know the the number one thing that people ask is what should you do when you to get better deliverability answer so yeah I mean test a lot right like it's a no-brainer we're going to screen this test a lot yeah absolutely and you want to test a lot and you want to get through it and and basically go through it and now you're probably asking well how do we test if we're telling you things well I have a very simple formula that you can understand right now to go ahead and start testing today and this is very proven it's what I do today it's how we did it at an ESP and this is actually a really great way to kind of think about it right and this is 100% free this is my favorite part about it so first things first you create 10

20:11inboxes and what you mean what I mean by this is what kind of tenin boxes well you're going to look at your data and based on your demographic you're going to create that you've seen this kind of pretty chart before some version of it inside of your ESP that tells you your breakdown by percentages of how many Yahoo and how many Google and how many AOL and you're literally going to mimic that based on percentages powered by 10 so if I have 50% Google I'm going to create five inboxes for Gmail create two one one hot mail one apple and so forth here's the trick and number four here is the really important part you never open these all you're simply doing is checking out the placement of where these are occurring that's what you want to do you want to pretend and not feed the systems any behavioral actions these are your seeds that are purely for deliverability inbox texting and so you want to go and start by saying hey is that email inboxing where is it showing

21:05up and then you want to start going through the system right the first thing I always tell people is to check out is it a domain problem and the easiest way to kind of check if it's domain problem is just add a one to your domain on your sending domain and send it to yourself as a test again and see if that email is sending to a different deliverability inbox right is it hitting the inbox is it hitting primary or or promotional or is it hitting spam that little trick will allow you to know if it's a domain reputation problem from there from there you're going to start thinking about all right if it's going your spam in Blacklist still you obviously have a domain problem you need to check your dmark your SPF your DK and review your sending practices from your segmentation and so forth so that usually tells you that you have a domain problem however if it still shows up and it's still spamming then you've got to go through some of these and I I rank him through

21:56importance of how you should be going through this situation and this is how I'm going through and checking out how email deliverability really works so first I'm going to go through the links is it going to your website is a link causing a problem I'll remove and strip the link out for example and I'll try to see if the email continues to do the same reaction if you check remove the link and it ends up going to a inbox and it was going to spam well there you go there's your problem and you're going to literally do that with each one of these you're going to go through your content you're going to go through and scrub some words out the way I do it I start from the bottom and I scrub out half the email did it go to inbox after I tested and removed it then I had something wrong with my content then I go into images maybe I'm using too many stock images maybe I've used the same image a

22:38million times sometimes images will trigger spam because of not only yourself but other people that might be using it and that's still not doing it then I'm going to check the subject line and take the prub line the sender name the sender address believe it or not an address can cause and spam a flag I'm going to make sure that I have my can spam disclaimer which is you know my Marketing address and my information and also making sure I have my insubscribe link so I'm literally going down this each and every time to make sure that I'm testing to ensure that my deliverability is occurring and trying to figure out why my inbox is why the email I'm trying to test right now is not inboxing and I'm going through it backwards to go Discover it and find out what's happening and then step three you start eliminating and testing each one of those right just like I explained you eliminate you remove one by one and you're checking and seeing if things are

23:27working and it's not ultimately working and that's it right and use those inboxes that I told you about those 10 to start sending and testing again a big reminder do not engage do not open just check for placement right now step four now my emails are inboxing but why aren't I getting clicks Chase why am I not getting clicks if my emails are inboxing so you're you're getting things delivered people are opening them but they're just not engaging it's your content dude basically look like it's it's the one variable that we have left to mess with right people are receiving the emails they're opening but they're just not engaging it's your content your content is not meeting their their needs right like we can't force someone to click people have their own free will so you have to make sure that your audience can resonate with your your message right you know that can happen through solving their problems right so giving them kind of helpful educational emails that they have to click through to read

24:25on a blog post or maybe watch a video maybe you're not being kind of you're not driving on psychological elements of fomo or scarcity or curiosity or maybe you're just not offering real value I see a lot of people come to me like hey do you mind reviewing this email it's like I don't really know what this email is about there's no real you know answer

Understanding Subscriber Needs

24:44to what's in it for me from the subscriber or the customer so before I press send before Jimmy press send on every email we're trying to think in our head what's in it for our subscribers and if we can't think of a reason we're going to scrap it and and rework it so and the more that you learn through all the different types of me methods of collecting information about your guys' subscribers to find out about their individual specific needs and the more that you segment and then you send relevant content there's no way that your clickr rate is not going to improve and if you drive more clicks right now you're setting yourself up to drive more conversion so at the end of the day your content has to be good it doesn't matter if your subject Line's good and if you're getting into the primary folder if your content's not good people just are not going to click yep absolutely and what it comes down to is this right

10 Quick Tips for Better Email Delivery

25:28and we've got two more slides here but the first one Chase I'd love if you can give the 10 quick tips for delivering your emails better these are best practices again and then we're going to drill down into what it really means in 2025 so I'll let you break these down well I know we're up on time so I'm just going to fastfire number one we talk about this a lot a lot of people talk about this a lot you need to be testing a lot and often so always be working to improve your email collection your campaigns your automations you know your deliverability you want to make sure that everything is leading to towards higher engagement and better performance and the only way that you can do that is through rigorous testing and and with the testing make sure that you're actually jotting down what tests you've run and how things are performed that way you can understand the trends I see a lot of people test and they just don't study the data and they wonder why

26:13they're not performing but I'm testing well you're not iterating on the data that's number one number two is ensuring that you have a clear sender name and you authenticate yourself so a lot of the changes that happened kind of last year with the whole Google Yahoo thing made this a requirement they don't want people to be ambiguous you have to basically raise your hand and say hey I'm Chase sending from Chase or I'm Jimmy sending from Jimmy or whoever it is the company name and you have to leverage the proper authentication like the SPF the dkim and the dmark that Jimmy talked about to ensure that you're going to be able to reach one of the primary the promotion inboxes that's a requirement now so make sure that that's set up properly number three so subject lines and preheader Tech so these are some of the very first things that people see outside of you know the from name which we already talked about so you have to make sure that they're relevant that they're not kind of click

27:07baity and they grab attention you have to stand out if you think about how many emails we all receive you can't just be vanilla you have to kind of make a statement but you also have to back it up with the content within the email don't do clickbait but you have to be a little bit hey look at look at me to get people to actually open your emails number four I think this one's common sense now but like don't go crazy with Emojis and characters and whatnot be normal like this looks like a text from my grandma honestly she just sends me nothing but emojis and things like this and I have I love her to death but I have no clue what she's trying to tell me so make sure that you avoid using unnecessary an excessive symbols characters and emojis in your subject lines and within your content as well because they can trigger spam filters and they don't come across super professional number five the body of email we talked about this before but

27:56again the content needs to be helpful it needs to be well written needs to be valuable and it needs to be personalized and based on the expectations that you've set with your subscribers and your customers if it's not then people are not going to engage and therefore your reputation's not going to do as well and therefore your deliverability is going to suffer number six links Jimmy talked about this but you know the links and where they go is super important right you know if you're trying to be an affiliate marketer and send out to all these spammy offers you're going to get dinged you know if you're a company that's an e-commerce brand more often than not you should just be be linking to your own company's website maybe it makes sense to occasionally review to like a reputable review site or maybe to like a YouTube video or something but more often than not the links within your content should be your own and they shouldn't be spammy or suspicious I know I'm going fast but

28:44kind of moving on number seven this is really important making sure you have the proper ratio between text and images you know sending the single image emails isn't great that is going to ding you you know kind of slice and dice it make sure there's a mixture of images but also text and with the text make sure that the text is actually live text don't just do a screenshot of text that doesn't help I see a lot of people screenshotting text because they want a specific font that's still an image like you have to make sure the text is actually live text and and plain text not just a screenshot of text number eight inactive data you know you don't want that you need your data to be active people want to be and need to be opening and clicking and engaging with your emails and if you're just mailing a stale list that's going to kind of bite you later number nine is spam trigger words so being cautious of certain words I mean there's a a ton of words but like

29:33overusing free or overusing guaranteed or over using limited time offer just too many times and again there's a whole bulk other list I can't go through today but just be mindful of the the words that you're using because they do matter and then lastly making sure that you have a clear footer with an easy unsubscribe is super important for compliance you know if people can't unsubscribe they're going to Mark you a Spam which is the worst thing that can happen so that was a lot does that make sense no that was great man and let's go into

Best Practices for 2025

30:012025 specifically as you're starting to master it in the retention marketers and Founders and operators in here listening what are you should be thinking about outside of those best practices so let's go ahead and break those down chase the first one we've talked about this a lot so I'm just going to kind of quickly I guess so we haven't talked about this one as much we talked about this a lot on the Pod the first one is

Advanced Tools for Email Marketers

30:22Google postmaster it is by far the best tool you can have at your disposal a it's free and be it's the data directly and specifically from Google it's basically Google analytics for your website traffic but specifically for kind of your email that you're sending it will tell you all the different types of things about reputation you know and is your stuff being authenticated properly Etc it's free a lot of the esps do not report this because Google kind of has a stronghold on this and they keep it to themselves so make sure you have Google postmaster it's the only and primary way to get data from Google directly from the source the second one is Yahoo centerhub so this is also free it's very much around the Verizon and AOL emails just like Google postmaster Tools Yahoo now has a sender Hub where you can track your spam records you can upload your Bimi images you can do all these things you should 100% start using that too as an alternative place to look at the ESP data is no longer just

31:18sufficient enough you need to be doing more today this is something that's just released not too long ago 100% look at that absolutely seed testing on emails

Optimizing Email Content and Engagement

31:26Jimmy gave a great example when we talked about getting better at deliverability about creating the 10 in boxes this is that we just wanted to reiterate how important that is make sure that you're always sending to your seeds so that way you are trying to understand what your user are actually going to receive and before you even send to your full list by testing with your seeds you know maybe they all hit the spam what could you do what could you change and going through that list before checking spammy words checking links you know checking the ratio between text and images if you can make a few adjustments before you hit your whole list that's going to really make difference and then of course mobile becoming bigger than ever you want to make sure you're starting to look at your desktop and mobile email separately checking and ensuring that they look good they act well the clicks work really well and all the links and the website and everything works really well together too and number five is focusing

32:16on the CTR so basically the click through like the Click to open rate essentially understanding of the people that are opening and obviously right being mindful that opens can be inflated through kind of some of the Apple stuff but being mindful of that understanding who is actually clicking links within your emails what does that percentage look like who is doing that and if there is a low click to open rate that means you again have to go back you know your content dude that whole thing that we talked about you have to go back to your content you have to make it something that people want think through your offers think through your positioning all those types of things matter to increase the number of people are actually clicking who open your email yeah and click rate often is Mis misleading because you're looking at your over overall send volume which you've got to drill down because if you have a low open rate you probably have a deliverability issue more than you have

33:04a open issue just because the way that MPP and iOS 18 and all these different changes that are occurring so make sure you're drilling down one level de deeper in fact number six I think this is huge right now because people are only looking at their surface level metrics I'm talking about oh I loaded my Dash where I see my open rate my click rate but what you need to be doing to understand your deliverability and how successful is is actually dig one layer deeper driving into your deliverability tab and going down and looking at how did my Gmail do how did my Verizon do how did my Hotmail or Microsoft do how did my apple do looking at those metrics looking at the specific open and click rates down at that level is going to give you a better understanding of what's actually happening within your inbox oftentimes the number one thing that I find when I audit and count is someone has a single point of failure occurring oftentimes Gmail or Yahoo which are your one two punch of your

33:58main dollars and cents that are being ignored because of surface level you don't see that so number six is all about going deeper into your metrics number seven unsubscribed to action this is actually one that Jimmy talked about so if you think about like an omnisend or other ESP essentially what they're understanding with every list is of the clicks that occur which ones are positive and which ones are negative positive would be things like they're clicking a link within your email that goes to your site whereas a negative click would be someone clicking like on a unsubscribed link right so what is the unsubscribe to action so understanding again of the people that click on subscribe how many are actually doing it how many of the total licks actually link clicks actually go to unsubscribe versus the content itself and just being mindful of it again this comes down to relevant content and personalized content if you do these things everything is going to be better and then eight is revenue per subscriber a real metric of success I think people

34:55ignored what this really means but you need to be drilling down to what you're actually earning nowadays more than you should be looking at just your surface level metric so a real metric for success is 100% Revenue per subscriber last one for me on the segmentation side again well one make sure you're segmenting don't just batch and blast two the end all Beall is not 90day actives right you want to be more granular you want to be more specific it's only way that your content is going to perform at scale so you want to include things like buyers versus non- buyers you know within the buyer Cate or there's first-time buyers there's repeat buyers there's your best VIP buyers right so when you're thinking about segmentation you do need to have different groups Beyond just a 90day active because that's that's too General sure you can send some to that but that doesn't distinguish between buyers non- buyers people that bought with a discount people that haven't bought with a discount it's just it's just too

35:46inclusive or we want to be a little bit more exclusive these days and last but not least number 10 remember that emails are now being sunsetted what I mean by that is if an email has been dormant for 24 months on Google 12 months on Yahoo or Microsoft this means that these are aged emails that have not engaged Google and Yahoo and Microsoft are sunsetting AKA deleting them or converting them into spam traps and so I know that sometimes the you know you've got a big promotion going on you want to reach out and throw the net out and you want to go tap into those really really old emails this is something you guys really want to be careful about right now because tripping up on one of these can create a specific problem with that TLD your top level domain your Googles your yahoos and microsofts so this is something that you should 100% think about when you're going through it so these right here as we're kind of wrapping this up these are

36:38your 10 things that you need to be thinking about as a retention marketer in 2025 things that are really impacting and changing the way you look at the email for the first time I think in many years the playbooks are changing the things that are becoming really important are changing and deliverability is becoming one of the most important topics for a retention marketer and as you guys are listening to this and leveling up your skill I hope you guys understand why this is very powerful next thing I just want to give a special invite I know Nick at the beginning of this thing also threw it out there we'll throw the link in the comments also if you love retention marketing and your retention marketer this not for Founders and I mean you guys are all welcome to come join us but really you're retention marketer and you love what we're talking about and you want to get deep like this you want to talk about deliverability you want to talk about Ai and different things we

37:25have a community of over 300 retention marketers that are available that we are hanging out on slack talking doing webinars and doing different things and dissecting different things that we're doing come join us we're going to drop a link in the chat so you can come check us out afterwards but that's your invite here today it's a buck for 90 days to come try it really engulf yourself get your questions answered we do email reviews and so much more with that I want to thank you guys all for allowing us to share our thoughts here today so if you want to find us on the web these are the places that you can find us on the web myself obviously on X and Linkedin those are my links that's my email address if you want to find us and Chase you can find Chase actually on these platforms and every other social media platform in the world he's everywhere Chase Diamond no a right there you go yeah thank you guys all for sitting here and enjoy hopefully we

38:14didn't nerd out too much fortunately or unfortunately you really can't get away from Jimmy Chase or myself on socials so you whether you've signed up for our emails or not you will find a way to get in your inbox or on your feed you don't have a choice no I'm kidding like I will say that very rarely this is this is why I love Ecom this is why I love what we do is that we can and this is why you're here because this is our people we're speaking the language of our people and we're trying to find our community ongoing and when you guys speak about this stuff like I'm I'm new to the retention space I'm an acquisition guy but as over the years especially as I'm in charge of retention subscription Etc I'm learning more and more now I can start speaking the nerd with you which is really really fun we

Q&A Session

38:56do have some questions You' extended time because you both are the best yappers in the space so I'm going to ask a couple more right here as I come into it so the first one Emanuel goes considering that there's a constant flow of net new customers coming into your email database as well as users unsubscribing what's the best way to accurately measure retention rates that's a great question I love this question all right so there's two two things that come into place for me number one you start off with just the store level data right before you even get into the retention of the email and SMS side you're looking at a store and looking at your repeat customer rate right that's going to tell you and identify how well your product and how much people enjoy your product and come back and average is about 30% some people are lower some people are higher obviously depends on you then you take the second layer of that thing and you start looking at the revenue per

39:44subscriber that you're earning and you're Trend lining the consistency of that and you're matching that percentage compared to your actual return Revenue number that your store is seeing right you're going to be able to kind of see hey how much am I contributing into the store versus how much my email and SMS and there should be a gap there it's not going to be spoton because people are going to come back to your pry your product without ever clicking on email or SMS so that's the way that I'm digging through that data Melissa asked us real quick before I get the other ones how much does your domain matter if it's not a.com doesn't they don't care M they don't they don't care not anymore these days as long as it's not like like XXX or dot like anything anything super gross or gnarly you're fine yeah there's so many tlds now it doesn't matter if I'm sending the same email but to different segments by domain do I need to swap oh do I need to swap out the

40:35subject line to avoid being flagged as spam no not at all I mean if you're sending different domains to different like like a Gmail and Yahoo and everything the spam filters are different right the spam filters and the recipients are different so the reaction will be different it will give you better data obviously if you're sending very hyperactive but it's not going to make a difference no Randy asks any tip on how to email private addresses from Apple all of these are bouncing for me oo that is undiscovered I don't know Chase if you've figured that out one with me but we just I mean the way that I look at him is Apple is already super finicky about the way that they handle privacy and bulk email it's hard because you don't know where this email is handling and going to and it's if they're if they're bouncing or they're rejecting you need to get rid of him as soon as you see it so that's the only advice that I can give on my side okay

41:26anything on that or is all good that's good cool there's a theory going around that it's okay to send image-based emails as long as you add text to the footer make it very small and essentially invisible what are your thoughts on this approach it's I just had a rant about this on social it's it's not bad it's not terrible but the reality is is like I don't understand and there's a plethora reasons why I'll go through it I know Chase has probably his thoughts but like there's a plethora of reasons why I think it's better if you're actually doing the right thing instead of trying to trick and manipulate the system if you've ever seen those things we like we're going to put you on the promotional Tab and bring you to the primary box all they're doing is manipulating by putting a bunch of text down at the bottom of it right but that's not really giving you the data that you want right if I'm sending an email out I want to know where people

42:14are clicking I don't want to know they clicked on the big box of an image did they accidentally click it did they were they trying to zoom in to look at the image and then they accidentally clicked it or were they intending to scroll and they accidentally clicked it things happen but I prefer when you can actually track it down Chase what are your thoughts around that yeah no I I agree and I think too especially with like some of the updates from iOS like if your email's all an image and then you have this random text at the bottom the summarization that you're going to have within the inbox is going to be weird right they going to start pulling random things because you're not going to have the proper text within the email so I don't know I feel like some of the categorization and some of the summary of the emails that you're sending if you do that are just going to be really weird you think save if it's like a

42:53massive promo s Black Friday cyber Mone is coming up you want to do a heavy text based and you want to get the you put you want to do a heavy imaged email but then make sure it inboxes would you use it as like a I really need to get into the inbox for them to open it would this be a play that you pull there if you had to I mean I think that it works and it's one of those things Nick like it works until it stops working does that make sense hey man so is a little boost but if you overuse it you end up un boosting yourself so at the end of the day what I tell people is it gets you to the same results you may see artificial lifts that occur and you may feel like you're a genius for about a minute or two but that genius disappears pretty quickly because you're not tricking technology at the end of the day there's actual engagement behavior and data that's occurring in

43:39the back of it no I'm G Li on this up and again it's it's a tactic to play and there's there's moments in time in your business where you're like dude I just need this ha Mary I really need to generate this rev and it's good to have something in the back pocket right like we we manage large lists that at the end of the day like prints money but we need to be very smart of how we leverage this two more questions for me for live text how to get over dark mode issue dude that is that's the million-dollar question these days I mean all you can do is design for literally design for black dark mode and and regular you just have to design how how do you know how do you know that like how do the only way you do is literally testing that's the only way I've seen it successfully done people are testing the alternative colors right there's a there's a Playbook on like if I'm playing Black

44:26it's going to turn white White's going to turn to black you're going to literally have to go down the chart design for that and then work on the same thing on the other side and basically test both modes on devices to ensure that you're doing that's the only way I've seen it successfully done there's no like magic secret with it right now I feel like this needs to be an actual like mini course like testing or or like testing for dark mode would be like a nice little presentation or or education Series so that Zar thank you for that that's a no I'll make sure we we think through that potentially okay final question how important is it to optimize for the highest possible CTR if your email content is valuable but easily consumable directly within the email many of our emails are value packed rather than clickbait should I still prioritize driving Clicks in every email she has a lot more we know driving traffic to our website is important but we also believe in delivering high

45:16quality within the email itself how should we balance these two goals KD first off thank you for your questions all day especially these ones you've been super thorough and thoughtful on how you're positioning this thank you so much for taking the time so this is a great question to end on guys chase you want to handle this yeah I mean that's I I think it's a great question like it it depends I think like for my personal newsletter I try to do a bit of both right I try to make a lot of the content consumable within the email itself but I also try I do try to link out when it's important right so I I do try to accomplish both because I'm going for more of like a newsletter approach but yeah I don't know I think I think it is important to get people to open them ideally right like with these types of things I also like to get people to reply so Jimmy and I ran a camp pign I

45:57think it was last Thursday or Friday where we basically asked people to reply to the email and I think we ended up with like 150 or 200 replies which is a really good signal and then I reply back to people as well so I would try to do things like that as well although it it did take me a lot of time to actually reply to everyone but I think it is a great way to engage your audience get people to reply have the conversation so I think you could do both yeah and don't forget the spam filters are also watching if you're spending time how long you're spending time on an email and how many Scrolls and up and down you're doing along that email too so even if they're not engaging on the CTR level as long as it's engaging enough where people are reading it and enjoying it you're still doing a a service to your score and your reputation rank so it's not terrible newsletters are very much an example of this right we send a

46:45newsletter out for example and there's a lot of text and not a lot of clickthrough rate options there and sometimes we don't get a lot of clickthrough rate but we don't see a decline in our deliverability or our engagement because we know the value of the cont content is being engaged inside the email and it doesn't mean that it's always coming out on the other side the metric so good I we can keep going on the Q&A guys again you're you're such an AAG chat we got more speakers I want to share and keep with you chase and Jimmy where can we find you actually we all know where to find you we're already finding you anyways so we don't want to know any other places look guys I live close to chase so like I could literally see him on my feet this is true story I'll end it on this one true story my wife had a block Chase because she's like I'm sick of seeing him all over and know that he can come to the house

47:27so it's actually it's it's actually a real thing she's like I'm tired of seeing this dude all over the place but it's it's funny like this that is why I love you for being who you are and Jimmy I'll see you backstage all right guys thank you guys all all right bye