AI Found What's Wrong With Your Emails

Chase walks through using AI to audit and fix e-commerce email programs. He shows how to prompt AI like a retention strategist, input your metrics, and get a scorecard that spots missing flows and over-reliance on discounts. Then he demonstrates generating and iterating on email copy, building content calendars, and analyzing competitors.
Chapters
This is really important here is the ask. So you're gonna ask Claude, where am I underperforming? What are the top 3 fixes that I should make? What am I doing wrong? And give me a 90-day roadmap. We need to focus on reassurance here, not necessarily a discount. We wanna make people consider it heavier. The more back and forth that you do with the AI and the more prompting and the more robust these prompts are, the better. The rules of using AI is you have to edit and review everything the AI writes. Giving AI your actual data is gonna make a world of difference. And then reading it out loud, just like you would write and read any copy. And don't allow AI to fabricate stats. When they make something up, wreck them, push back, and just double-check everything.
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? Doing a solo episode today without Jimmy because we're gonna go through an actionable presentation that I have for you guys all about how to use AI within your content creation and your email marketing. Gonna be applicable for brands, agencies, and freelancers alike. Pay attention. We're gonna go through a screen share. Um, there will be, uh, basically a link in the description that will give you all these prompts. I'm gonna go through a bunch of prompts. This way you don't have to take notes. We're gonna give it to you just through the link. So look for that. But without further ado, let's dive into this. I'm gonna share my screen real quick so we can get into the presentation today. So hopefully you guys can see my screen, but as mentioned, going through email and content creation, and essentially what's gonna happen here is I'm gonna try to go through this in the next 20, 25-ish minutes. I'm gonna give you 3 primary things. Number one is I'm gonna give you guys a prompt that's going to allow you to audit your own email program. Or your client's email program. So that's gonna be something where you drop in numbers, you're gonna get back a rank list of what's broken and, and get priority back of what you need to fix. Then from there, I'm gonna give you a workflow and some prompts to actually recreate and rewrite the actual content. So the flows themselves, et cetera. So we're gonna see what that looks like. And then lastly, I'm gonna give you some prompts and some explanations on how to build out subject lines, sell the bell dot, 30-day content calendars, how to leverage, you know, your competitors' content to see where you're doing well and where you could be improving, as well as different segments that you should be running, hitting, and what you should be sending to each. So with that, what we're gonna basically do is I'm gonna run through kind of this brand that I made up. I didn't wanna share any client data, but I basically took data as if it were a real brand. So we can go through a tangible kind of case study and example here. So think about this diamond apparel company that I'm going to run you through as like a Viori, a Biltz, a Cuts, et cetera. Um, and essentially they're selling to 25 to kind of 45-year-old adults and people spend on average, the average order value is about $95 and people purchase every couple months. So this business has 85,000 subscribers. It's doing about 24% of its revenue from email. On average, they're getting about a 38% open rate. And a 2.1% click rate. And then lastly, you have the email setup. So they've got 3 automated emails for a welcome series, 2 for the cart, and 1 post-purchase, but they've got no browse, no win-back, and no sunset. So with that, right, I know that was a lot. It kind of sounds like on the surface, like everything's great and going well and doing fine. However, they're short on what they could be doing in terms of revenue. So they're at 24% of the revenue from email. They could be doing upwards of 30 to 40%. Their click rate is below the industry average at 2.1. The industry average is about 3 to 5%. And then the flows live, they only have 3 of the 6 core flows live. So when you run this audit, this is what you're going to get back. And I'm going to actually walk you through the audit in one second, but these are the types of things that you'll put in. And then you'll get basically a scorecard and a ranking on like where you can improve in And what you could do better. So on the next one, we're gonna see here, here's basically the prompt, and I'm gonna show you in 1 second the actual full prompt. This is just kind of what fit on the screen. But to kind of walk you through this, you know, it's gonna assume the role of a senior retention strategist that's audited 250+ e-com email programs. And you're gonna basically tell them to be— and tell them, I mean, Claude, ChatGPT, et cetera, to be direct, specific, and no fluff. And then you're gonna talk about the brand, right? So I told you a little bit about my brand. That's kind of mock Diamond Apparel. Enter in the ESP, the AOV, et cetera. Um, the numbers, the setup, and essentially this is really important here is the ask. So you're gonna ask Claude, where am I underperforming? What are the top 3 fixes that I should make? You know, what am I doing wrong? And give me a 90-day roadmap. So I'm gonna switch screens here, which if you, Follow the link in the description. You're gonna be getting access to 1, 2, 4, there's like 7 prompts here, but this first one on the left-hand side is the email audit prompt. And you're gonna basically replace all of these parameters, the Xs and kind of the personalization parameters with your own data or your own client's data. So here, right, went through the role, it goes through your brand, you know, it's gonna ask you for some metrics about your list. Etcetera. So you're gonna go through, fill this all out, and once you fill this all out, you know, you submit it to Claude, ChatGPT, etcetera. This is what you're going to actually get back.
Hey, quick 60-second break to shout out our title sponsor, Omnisend. If you don't know them, Omnisend is an all-in-one email and SMS platform built specifically for e-commerce. They've trusted by over 155,000 merchants with a 4.8 rating star on Shopify's marketplace with over 2,800 100+ reviews. People love using them. Their support is incredible, responsive team, great help docs. They actually show up when you need them. Look, everyone loves saving a buck. They've got great features and great pricing. Listen, I've heard this inside the community that someone actually dropped their bill by almost 50% and then included their SMS costs, which is absolutely wild. Another agency that we talked to shifted all his clients over when he discovered that he can save them 30 to 60% Off of their actual monthly bill and taking that money, reinvesting into ads. And that real money is going to come back into your pocket too, because you're helping them out or whatever it might be. With all this, I literally just helped Chase migrate his personal list to Omnisend not too long ago. It was super easy. They got team, they have an automated solution. It's really great. So if you're looking to scale your email and SMS game, check out omnisend.com/sendit. Tell them Chase and Jimmy sent you. Now back to your pod.
So you're going to see here's 6 kind of immediate fixes and they've identified 3 being the most urgent. So quickly going through each one. Number 1 is the welcome flows stop too early because you have a product that typically people spend around $95, close to $100. You should be sending more than 3 welcome emails. You know, you should be sending maybe upwards of 6 or 7. Number 2 is we've identified that there's no browse abandonment. This is low-hanging fruit. A lot of people view products, but don't add to cart. Don't make a purchase. This is going to be a great opportunity for you to target those folks. Then from there, it noticed that your cart abandonment flow doesn't have separate flows and doesn't separate based off intent between cart and checkout, right? Cart is for people that added to cart but didn't start checkout. Checkout is for those that started checkout but did not make a purchase. And then from there, right, there's no win-back flow. There's no sunset flow. And the promotions that you're sending are very promo heavy. They're very discount heavy. So the campaigns are typically sending about twice a week and they're mostly discounts. There's not enough value, story, brand building, et cetera. And then from there, what's gonna happen essentially is the, that same prompt that we had uploaded is going to prioritize of these 6, here are the 3 that you need to do immediately. Number 1 is the cart flow. And what we're gonna do here, because it's such high intent, is we're gonna split out the cart and the checkout, and we're gonna build those out into different types of content, different types of offers, different types of social proof. That's number one. Number 2 is you already have the welcome flow in place, but as mentioned, you're missing emails 4, 5, 6, maybe even 7. So we're gonna add those. And then the last one is because the browse doesn't exist, we are going to basically prioritize that. And if you wanna change any of the parameters, what I would probably do is come here to the bottom. And for the ask, right, you know, if you wanna say here's 5 instead of 3, what am I doing well? You know, what are 5 metrics I should ask for? Those types of things. You could always change the parameters. These are kind of just placeholders for you to at least kind of get the ball rolling. So next up, right, like this is kind of what we're gonna focus on. So going deeper into Sending kind of the same email right now. We want to separate these. So we're gonna have the cart abandoned orders, and then we're gonna have the checkout. So with the cart abandonment, we might do something like, hey, we need to focus on reassurance here, not necessarily a discount, because we wanna make people consider it heavier. And then with checkout, people got cold feet. Maybe something broke, something got— they got distracted. Maybe an email 2 or 3, we might wanna consider a small discount if the initial nudge doesn't work. So that's that. And then with this, what you're gonna basically do to then get emails that you can actually send is you're gonna paste in this next prompt. And this next prompt can be found in the sheet that, you know, right here called Writing Emails. And they give you the instructions right here about like fill in the brackets, you know, run this in the different sequences. And what you're gonna do here is you're now, you know, assuming the role of an email copywriter that's writing for kind of a warm audience. You're not desperate, et cetera. Again, giving the details and parameters of the brand, which you've already done if you did the audit step and then the writing. So, hey, write it for email 1 of 3, write it for email 2 of 3, write it for email 3 of 3. Do it for the cart abandonment, do it for the checkout abandonment. For the rules, for the cart abandonment, let's do no discounts, no urgency hype. Subject line should be under 50 characters, single clear call to action. And then the format, give me back a subject line, a preview text, a full body. And you'll see in this version, right, it breaks it out a lot further so you can basically kind of see what it looks like. And as a really quick example, this is just really simple for the illustration of this teaching is here's like a subject line, right, that I gave back. Still thinking about the weekend hoodie. And in yours, this is gonna be kind of a dynamic parameter that's gonna change based off the actual product that someone looked. Instead of the weekend hoodie, maybe it's the weekend t-shirt or the weekend shorts or whatever the product is. That's the subject line. And then the preview text is, we set one aside in your actual size. And then the body copy is, hey, so-and-so, We noticed this hoodie made it to your cart. We're gonna hold this in your size for the next 24 hours. The same hoodie was purchased by 12,000 people who love it. It's heavy enough for actual weekends, but it's cut well so it doesn't ride up. Pick up where you left off, right? You'll have some design, some personalization, complete your order, finish your order. But this is just an example of when you use that prompt of something that you might receive back. And then from there, right, like the prompts are going to help you get, you know, 80 or 90% of the way there. They're not going to be the end-all be-all. You do still need some human editing. You need your voice. You might have to go through a few revisions of sending things back and forth to Claude or ChatGPT. But then from there, after we've audited, we've written it, we're going to now do a prompt to actually audit the draft that it wrote. And that will be in the document under audit the draft. And essentially what's gonna happen here is you're now a strategist who's reviewed tons and tons of e-commerce brand sends. You know, you're gonna audit, you know, the entire part of the draft. And essentially what you're gonna do is you're going to give me scores for different parts of the email. You're gonna gimme a sentence from each and you're gonna give me a rating out of 10. For anything under an 8, you're gonna tell me to redo it or rewrite it. So this is something that you'll get back right here. So for that email, the subject line is a 9 outta 10. Reason being, it's, you know, on-brand, specific, and curiosity-driven. The preview text is 8 outta 10. It works well with the subject line and adds new info. However, the hook, right, is a 7 outta 10. It has a strong open, but it could land harder and, you know, resonate more. So rewrite that, whether it's you personally or you, you send back notes to Claude, you upload the scorecard. In terms of scannability, in terms of looking at the actual email from a design and copy standpoint, they're short paragraphs. It's easy on the eyes. It's easy to read, easy to understand. However, you're getting a call to action of 6 out of 10, so you should rewrite this. The call to action is too generic. And on mobile, it looks clean, it reads well, so this is fine. So again, we're gonna go audit. We're gonna write the emails that the audit flags as something we need to focus on as a high priority. And then we're going to audit this. And then after you audit it and you make the changes manually or with Claude, you're gonna put the final polish and then it will be ready for sending.
Real quick one for you. Big news. Commerce Roundtable is hitting the road this June with Retention Roadshow. We're hitting 4 cities, New York, Miami, LA, and Austin. And here's what's really cool. This is a half-day workshop-style event built specifically for retention marketers. That's you. We're talking about tactical sessions with email, SMS, AI, and lifecycle. This is the stuff that moves the needle on repeat purchasing and LTV. And these will be small rooms. We're talking 75 to 100 people max. There won't be any fluff or high-level theory. This is really walking into the practicality. Plus, you're going to walk away with strategies that you can implement that week. Plus, we're going to include breakfast, lunch, and of course, plenty of networking. To have real conversations with the great people around you. Look, tickets are limited because of the room sizes. So you can go over to commerceroundtable.com/roadshow. We're gonna put the link below and use this code SENDIT to get $25 off a ticket. It's not very expensive anyways to go. Again, we're coming to New York, Miami, LA, commerceroundtable.com/roadshow, code SENDIT. Come hang out with me, come hang out with Chase, hang out with a bunch of retention marketers. Back to the pod.
So that's kind of that process there. And then kind of moving on, the next part here is like, how do you generate subject lines that are relevant and interesting and on brand? So what you're gonna have to do is we're gonna focus on, let's say, summer essentials. That's like coming up, you know, maybe when you're watching this, this is summer. You're gonna come up with a prompt that basically says, hey, give me 10 subject lines again for my brand, Diamond Apparel, who focuses on this audience, I want a mix of curiosity, urgency, social proof, benefit. So subject lines don't get cut off by Yahoo, Gmail, et cetera. Keep them under 50 characters and no clickbait, right? And here's just like a sample, right? Your closet got quieter. Summer essentials last 48 hours. And you can see what angle they're playing to. The T10,000 or 12,000 that you asked for, social proof. Built for the office, made for the weekend is the benefit. What our customers wear after work, right? Is curiosity. And then urgency. If you're doing a drop, drops Friday, gone by Sunday. So this is kind of something you'll get back. You'll get back a table or, you know, different types of ones. Again, I don't like this, change that, rewrite 'em yourself. Subject line should look like this. The more back and forth that you do with the AI and the more prompting and the more robust these prompts are, the better. But again, subject line prompts. Here's the overview. Here's the workflow, and here's the prompt itself. So copy that, fill this out, get it going. It will do 80-90% of the work. You keep training and building it, and over time you've got a really rich chat history and library where Claude is going to be, you know, a really, really great asset for you and/or your team. The next part here. Is building out a 30-day calendar really quickly. So tell Claude what you're working on, and then it's gonna give you ideas based off of your brand, the season, and everything else it knows about you that will help you. So the problem I mentioned with Diamond Apparel is it was sending 2 campaigns a week and they both were promotional. So our goal now is let's start sending 3 times a week and let's focus on a mixture of social proof, value, brand building, brand storytelling, and never do more than 2 promotions back to back. Give me a table of what this could look like. So for example, on a Monday, we might send an email that's value-based saying, here are 3 ways to wear our linen shirts this summer, right? How to dress them, how to style them, how to not get too hot in them, whatever that looks like. And then from the story, it's like we cut the seam. So why is your design— and maybe you have some patent— why is your clothing, your fabric, your material Better, different. That's really focused on brand building. And then if you're gonna do a drop for some kind of promotion, summer drop, last 48 hours remaining, and this is really focused on revenue. And if you go back to the handy document, this is gonna be the full prompt here of actually how to build this out and make sure that you're hitting different segments, you're hitting different people, et cetera. And then 2 more before we wrap up. And hopefully this has been helpful. If you have any questions, drop them underneath this video and we'll circle back and answer anything that we may have missed and we'll create some other content as well. But the first one is going to be a competitor teardown. So here, right now, Diamond Apparel competes with Buck Mason, Viore, Built, Cuts, et cetera. What you're going to do is you're basically going to copy in or screenshot in 5 to 10 of each of your competitors' recent emails. And you're gonna ask AI to analyze the cadence, the content mix, the flows, just to really understand side by side where you're at versus where they're at and how you can kind of differentiate yourself. We also have a platform called Inbooks. That's also a great way. So the way in which you get these emails is either go to inbooks.ai or just manually subscribe, like go to built.com or builtbasics.com, whatever their site is, enter your email. Star them, keep them, upload them into Claude, et cetera. And this will be kind of the prompt that you do here is, hey, you're a senior retention strategist. We wanna compare our program versus their program. These are the competitors. Here's a little bit about them, right? Buck Mason sells premium men's essentials and they probably have a similar, if not greater AOV to us, right? I think their stuff's more expensive, so maybe they have $150 or $200 AOV, for example. For each one, study these, right? Subject lines, the send time, the send dates, et cetera. And given the analysis of where we're ahead, where we're behind, and really where we should focus on our campaigns and automations for the coming months. And then the next part as well is the segmentation side. So a quick break to talk about SuperScale. If you've ever found yourself on a Friday afternoon scrolling through the Meta ad library, screenshooting your competitors' hooks and trying to reverse engineer why their ads are working while yours personally have been stalled. That's exactly the problem that SuperScale is built to solve. It's the first AI agent specifically for social marketing. You connect it to your Meta, TikTok, and your Google ad accounts, point it at your site, add your ICP, and pass testing notes, and it actually goes and does the work. How cool is that, right? You can literally prompt it to analyze your top competitors, identify what's converting in your space, And turn that into a new batch of creatives across different formats, all from a single prompt. What would normally take a designer and a growth lead a few days can now be done in a matter of minutes. They're backed by C— Cradium and trusted by brands like TaxFix and SumUp. You can check them out at superscale.ai. Now to the show. Hey, we're on Omnisend. We have 85,000 subs. We have a 38% open rate, a 2.1% click rate. We typically send to our engaged, which we define as our last 30 days, our at-risk, which we define as our last 31 to 90 days, and our inactive, which are 90 days and beyond. And with this, right, give us kind of the table with the cadence, content type, and goal per segment that we should be focused on. And when you do that, you go here to segmentation prompt and you copy that in, and then you're gonna understand, okay, we don't have a VIP segment here. We don't have people that had gone through maybe our abandoned flows, but didn't buy. We don't have folks that bought last BFCM, like building out the right segments and the right content and ensuring that you're sending content to each one so that way they hopefully don't lapse or go inactive. And then the last thing here is AI. Again, it's gonna get you 80, 90% of the way there and it's getting better by the day, right? Right by the minute, really. But that being said, like there are still a couple things that you really have to look out for. Number one is AI loves to fabricate stats. So a number that sounds right, but it might be slightly off. So make sure you're checking that. For whatever reason, they love to invent features and make claims about your product or your service that probably aren't entirely true. And they make unverifiable kind of hype claims. So you might have 100,000 customers and they might say you're trusted by millions. So the rules of using AI is you have to edit and review everything the AI writes. Giving AI your actual data is gonna make a world of difference, and then reading it out loud just like you would write and read any copy. And don't allow AI to fabricate stats. When they make something up, correct them, push back, and just double, double check everything. So hopefully that was helpful. Again, if you have any questions, let us know. The prompts for this all will have been in the description of this video. And if you want more kind of actionable videos like this from Jimmy and/or myself, let us know in the, in the chat. We'll see you guys soon.
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.










