Exit Five: B2B Marketing with Dave Gerhardt

Dave sits down with Knak Co-Founder & CEO Pierce Ujjainwalla, and SubjectLine.com Founder Jay Schwedelson, two experts in the B2B Email Marketing, for a one hour deep dive into what’s working in 2024.

They cover:
  • Subject line strategies
  • Design do’s and don’ts
  • What makes a truly great email in 2024
This is a recording of an Exit Five Live session - to follow along with the examples, check out the deck here.

Timestamps
  • (00:00) - - Intro to Jay and Pierce
  • (05:13) - - What Personalization Looks Like in 2024
  • (09:58) - - Using “Friendly Froms” to Increase Open Rates
  • (14:11) - - How the Best Emails Are Designed
  • (17:53) - - How Often Should You Send Emails?
  • (18:57) - - Sending a Killer First Email
  • (26:42) - - Your Reader Needs Context
  • (28:27) - - Use First Person for Better Call-to-Action Buttons
  • (31:25) - - How to Avoid Confusing Content
  • (36:13) - - Why You Need To Focus On Building Trust
  • (37:52) - - Writing for Engagement
  • (45:28) - - Email Branding Trends in 2024

Send guest pitches and ideas to hi@exitfive.com
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What is Exit Five: B2B Marketing with Dave Gerhardt?

Dave Gerhardt (Founder of Exit Five, former CMO) and guests help you grow your career in B2B marketing. Episodes include conversations with CMOs, marketing leaders, and subject matter experts across all aspects of modern B2B marketing: planning, strategy, operations, ABM, demand gen., product marketing, brand, content, social media, and more. Join 3,500+ members in our private community at exitfive.com.

Jay Schewedelson [00:00:00]:
1234.

Pierce Uijainwalla [00:00:01]:
Exit.

Dave Gerhardt [00:00:08]:
Exit, exit. Hey, we're here at the top. We got this highly anticipated live session. Don't call it a webinar. It's not a webinar. It's a live session. Capital L, capital s live, live session. We're going to cover email.

Dave Gerhardt [00:00:27]:
We're going to go deep dive in email. We have a bunch of best practices. We're going to spend about 15 minutes giving you some insight from Jay and Pierce based on their experience. Then I have a deck. We actually got real examples from companies that are inside the exit five community. They were brave enough to send us their emails. I actually was blown away by how many people sent emails. If we had a three hour session, we could have done them all, but we didn't, so we picked some good ones.

Dave Gerhardt [00:00:51]:
We're going to dive into some feedback on those emails, I hope. I think like most things in marketing, there's going to be an 80 20 rule. So, like, whatever we say about one email is going to be applicable to you and your business in some way. And then I want to leave time for myself, Pierce and Jay to hang out with you and answer your questions. You're the ones who took the time out of your day. We just crossed 250 people here. Holy cow. All right, without further ado, I'm going to turn it over to real quick.

Dave Gerhardt [00:01:15]:
Pierce, you're going to introduce yourself. Jay's going to introduce yourself, talk about who you are, what you do, and then Jay's got some slides. We're going to go from there. Here we go. Lightwork says Mallory Pierce.

Pierce Uijainwalla [00:01:24]:
Uijainwalla shoutouts I saw another pierce in the comments. I've only met three in my life. So what's up? Piers Smith. I'm Pierce Uijainwalla. I'm the co founder and CEO of NAC. NAC isn't is a marketing platform. We make your lives as marketers a lot easier to help you build your digital campaigns.

Pierce Uijainwalla [00:01:44]:
I've been doing email for like 20 years now for way too long, but really excited to be sharing some of my tips with you all today. Jay, over to you.

Jay Schewedelson [00:01:55]:
I'm Jay Schewedelson. I'm the founder of Guru Mediahub and we have a bunch of free content and things for marketers. Subjectline.com is a free resource for marketers that I started like 15 years ago. And you can check your subject line there. And we put on the world's largest email event called Guru conference, which is a virtual free event. So we have 20,000 email marketers that go to that so I spend a lot of time in the email world and the B two B email world. Excited to be here.

Dave Gerhardt [00:02:23]:
Let's get into this. So before we flip over to the email examples, we're going to set the table here with some best practices. Talk a little bit about what makes a good email good. Jay's got some stuff to talk about. Subject lines first, because before you even get into the email, you get that subject line and it says free pizza. And the open rate is 100%.

Jay Schewedelson [00:02:45]:
You had me at pizza. So before we get into the emails that you all submitted and what's good or bad about all them, and Pierce is going to take us through some design stuff. I want to spend just a few minutes to talk about the elements that get your email opened. Right? Cause if you don't get the email open, who actually cares what's inside your email? So the number one thing that's gonna dictate whether or not your email does or does not get open is your subject line. And one of the things, the things that bothers me about best practices in general is if you go and you google what are the best practices for subject lines, they'll tell you personalization. And what most people think personalization is, is the horribleness of putting J comma whatever in that subject line, the person's first name. That worked five years ago, okay? That's not what you do anymore in terms of personalization in the subject line. That's not what works.

Jay Schewedelson [00:03:36]:
But personalization is the number one driver of getting your emails open. So I wanted to take you through a handful of things specifically for business to business marketers that are crushing it right now. And this is data from, we send out about 6 billion emails a year. This is data from the last 90 days. So in your subject line, what you always want to think about is this simple thing, tell the person who they are. The sooner you tell somebody who they are, the faster that they want to engage. Right? So for example, if you put in the subject line, if the name of your company was Acme, and then you got a subject line that said, is Acme at risk? Like, oh my God, whats going on in my company? I need to check it out or Acme needs to know this. What do we need to know? Personalization of the company name actually lifts open rates by about 41% on average, because it speaks to you the same thing for job function.

Jay Schewedelson [00:04:28]:
So often as marketers, we target by function, we target people by HR Pros, right, or CFO's or whatever it is. Tell them who they are. When you put the job function in that subject line just for HR Pros, if it said just for B two b marketers, you're opening up that email increases open rates by about 38%. Same thing for industry. Tell them who they are. This is trending in the retail sector. I work in the retail sector. I better open this up.

Jay Schewedelson [00:04:56]:
Some other new things that are working really well is this idea of us versus them, right. If you see your company name versus another company name in that subject line, like, whoa, this is wild. You have the data, you can personalize like this because you're targeting like this. It's just putting it in that subject line. And then the last one is longevity of the customer. Right. If you are marketing to your customer database, this is just for our new customers. This is for people that just renewed.

Jay Schewedelson [00:05:24]:
This is for customers that have been with us for five years. Tell people who they are and that is how you get people to want to open up that emails. So we'll go to the next slide and talk about the other key piece. The other key piece is the from address, right. And this is really, really important. When we send out our emails, you have the email address that you send from. My email address is the letter j. Schwettlesonorpwd.com.

Jay Schewedelson [00:05:47]:
but when you get an email from me, it says Jay Schweddelson. It looks nice. And that's because I changed the friendly from. It could literally say howdy duty. I could have it say whatever it is I want it to say. Right. You could change that from name to anything. I'm not talking about changing your email address.

Jay Schewedelson [00:06:02]:
Right. You could literally on every send that you do change the from name. It doesn't impact your deliverability. You're not changing your sending name. Why does that matter? Because now what works is treating your friendly from that from name as the start of your subject line, basically. And so when you take that friendly from, and instead of it just being acme, it could say acme events, it could say acme demo, Acme new event. Right. Acme special guide.

Jay Schewedelson [00:06:31]:
You put whatever your offer is in that from name and you change it every time you hit send. And that way it gets the person a little bit more excited to open up your email. And that's what you see here on the screen when you're friendly from matches. Whatever it is that you're about to talk about, it increases open rates by 31%. My wife's a dermatologist, so this is her inbox. This is all the same sender. They're just doing different things with their from name. And if you go to the next slide, the last piece of this, look at Apple just as an example.

Jay Schewedelson [00:07:02]:
The other benefit is not just that you get people to understand what you're emailing about faster. There's always this argument internally in every organization is we want to send more email, but we just sent the email, we can't send more email. And there's the internal conflict, right? Apple on any given day sends you five to six emails a day, all from the same address, all to the same address. But what they do is they delineate in their from name what it is that it's about. So you, the recipient, you don't feel like it's the same sender. You don't get annoyed. So the way that you can win the internal battle to be able to send out more is to almost create these brands by using the friendly from. It could be Acme events, right? Acme special content, Acme software update.

Jay Schewedelson [00:07:45]:
It allows you to have license to send out more, not annoy people. And that's how Apple wins the day. And that's how b, two b markers are winning the day.

Dave Gerhardt [00:07:52]:
Right now I'm going to ask you a selfish question. So right now we're thinking about our email strategy at exit five. We brought on more people, we got more stuff to do. We got to send a little bit more email. We have this one email that we send out regularly, which is our newsletter. How would you handle sending things like a webinar promo or another type of email? Would you that we want to send. Give me like a practical piece of advice for. So Danielle sends our newsletter.

Dave Gerhardt [00:08:16]:
So the newsletter says, danielle from exit five. What would you do for the other emails?

Jay Schewedelson [00:08:21]:
So let's say you have your events, it would be exit five events that would literally be in that from and even a lot of newsletters, it doesn't come from a person, which by the way, I think that is the absolute best tactic to do. You could do things like exit five, FYI or ad age does a great job. They do ad age don't miss when they have things that they really want people to see so you can delineate. So people start to get to understand, oh, this is their events thing. This is their special guide release thing. And you start to almost brand it in people's minds. These friendly frums are about different things and so it is sub brand within your email sending. You don't want to have just one friendly from because that's just one big slop of garbage.

Jay Schewedelson [00:09:00]:
And then that's where your open rates go down really good. So, Pierce, I'm going to hand it off to you because now we got people to open up the emails. We won the day. Now it's your job to land the plane and let's get them to click on this stuff.

Pierce Uijainwalla [00:09:11]:
Let's do that. Jay, killing it. As always, I love that you started with the subject line, because that is really the first battle that all of us marketers have to win. We have to get people and captivate them to take action. And so really, what we've developed here at NAC, we're all about helping marketers move quicker, go faster. And so the cheetah was the obvious animal to pick to help all of you build emails quicker. And it's also the acronym that I really like to use. It's my framework of amazing, making amazing emails.

Pierce Uijainwalla [00:09:46]:
A lot has to do with design. But, yeah, she's already touched on a lot of great points on the captivate side. You know, you have to get people interested, curious to actually click and open your email. And then once you've done that, then you can focus on the design, which I'm going to talk about today day. So on the human element, we are all humans. At the end of the day, what emails do we open most? We open most emails from other humans that actually sent them to us. And we like reading emails from people, people who are sending us one to one emails. I think personalization is great.

Pierce Uijainwalla [00:10:26]:
The queen of this is Anne Hanley. She does an amazing job. If you ever want, I highly recommend. If you haven't subscribed to her newsletter yet, do it. And look at how she writes. My big hack for this is pretend you're writing every marketing email. Just open up Gmail, put in your friend or someone you know, maybe a customer you know personally. How would you write to them? I have a feeling it's going to be different than how you write your mass emails.

Pierce Uijainwalla [00:10:57]:
E for entertains. So we're in b, two b. I know a lot of b, two b. Marketing can be boring sometimes. It doesn't have to be. But I think the hardest part there is taking the risk to be different. So what I would encourage all of you is take a risk on something. Tell your boss, tell your cmo.

Pierce Uijainwalla [00:11:16]:
I want to try something and let the results speak for themselves. Easy. We are all very busy. We look at emails for a matter of seconds. It has to be short, quick and simple so that people know what they're doing without having to engage much of their brain in the process. When it comes to design. A lot of nice HTML emails have lots of different sections and for some reason marketers love to do boring straight line transitions. And this is somewhere that I think we can be creative and add that really an extra element of design there.

Pierce Uijainwalla [00:12:00]:
Animate for gifs or Gifs or however you guys say it, this is something that can also elevate your email. It can also ruin your email. We're not trying to give anyone seizures here, but with subtle animations you can help elevate your email. And I'm going to have some examples of those. And then finally, you know, Jay started with the subject line. That's step one. Step two is the design and hopefully getting someone to click. And when they click, you're going to get them to a landing page most likely.

Pierce Uijainwalla [00:12:34]:
And you need to have harmony on those two experiences. People need to know if they're looking at something that's promoting a cardinal. You don't bring them to a landing page with a boat on it. Right. It needs to be simple and flow together. So I want to show you two emails that I think I do a great job of this cheetah framework. And to do that I'm actually going to go into NAc and show you these two in our inspiration center. So the inspiration center, if anyone's ever been on these different websites that have a bunch of different emails and different categories, you can kind of pick your email and you can actually use them.

Pierce Uijainwalla [00:13:19]:
So the first one I want to show everybody is the salesforce email. First thing you see is this amazing headline. Right? So that is really going to captivate you. What are they saying? Are they saying the f word here? No, they're not. But it's gotten your attention now, Dave, I love that you opened, we're not calling this a webinar.

Dave Gerhardt [00:13:43]:
I'm talking to my team in the side of my, I just saw the side of my eye and you literally brought me right then I said, is your data effed up? What?

Pierce Uijainwalla [00:13:51]:
Yeah, that is a great way. It captivated it, break the ice. It gets you through what you see in your inbox all the time. I also love that they're not talking about webinars here. Marketers have ruined webinars forever. Virtual events, streaming events, much cooler right now. I'm sure we'll ruin it at some point, but I'd say it's still in the cool phase. And then I was talking about transitions.

Pierce Uijainwalla [00:14:19]:
Salesforce does an awesome job right here with this kind of curve, transition and the cloud. Those are kind of those elements of design that I think really elevate your email. Great buttons here or bullets here to identify what is this. Quickly I can scan and see what it is and then it's easy. There's one button. What do they want me to do? They want me to register. I thought this was a great example. They used animation.

Pierce Uijainwalla [00:14:51]:
They captivated us. They kept it simple. And that was really good. Here's another one. This is a NAC one that we have just sent out to some of our customers. So again, looking at the subject line of this particular email, we had the subject line as who approved this email? And then the preview line was just one more edit. And so I think that as a marketer captures that human element. We've all been there, we've all went through 57 revisions of an email.

Pierce Uijainwalla [00:15:28]:
And in this particular email, we're trying to show you that we feel your pain and here's a better way of doing it. So again, with the animation, this one, I would say, actually isn't that subtle. But we're trying to use it in a way to kind of capture people's attention. Single call to action, quick to skim. What do you want me to do? A cool transition down here that kind of leads you to the call to action. What's some kind of design that you don't see all the time?

Dave Gerhardt [00:16:05]:
I'm going to just hang up. You guys nailed it. That was amazing. Take notes. That's how you do the first 15 minutes of a webinar. I got the exit five team is blowing me up. The chat has been awesome. So that was really good.

Dave Gerhardt [00:16:16]:
I really, really, really want to ask all the questions now because I have so many follow ups. Like I want to ask about plain text emails. I want to go back to Jay's question thing about the different from names. I want going to talk to Pierce about multiple CTA's in an email, but I'm not. I'm going to do what we said. We're going to stick to here. We got real brand emails that we're going to go to and then we will have plenty of time for Q and A. Let me share my screen here.

Dave Gerhardt [00:16:40]:
And we are going to show the emails that we have submitted. The first email right here. This is from Chili Piper. The subject line is welcome. We didn't grab all the from name, but we have the email. It's tarahillypiper.com dot. This email is. Hey, congrats on being on our newest subscriber to the sauce.

Dave Gerhardt [00:16:57]:
Thank you. I can assure you we don't take this lightly. This newsletter will be hitting your inbox once a month and we'll highlight new posts we've published, useful tips and upcoming events for our team and partners. In the meantime, I'd love to hear you answer these questions. Why did you sign up for a newsletter? What would you want to learn more? Your answer helps me get value in return. Let me know by hitting reply. Blah, blah, blah. And then they have a bunch of links and stuff in here.

Dave Gerhardt [00:17:17]:
So initial reaction to this one, guys.

Jay Schewedelson [00:17:20]:
First of all, I like Julie Piper and if Tara made this email, I like tower a lot. So no shade towards Chile Piper because I use them all the time. But I think there's something here that a lot of b two b marketers do that I think you either rethink this is a newsletter confirmation email. Somebody sign up for newsletter that they got this email. You have to always keep in mind that the first email you send to anybody, if they download a piece of content, if they sign up for your newsletter, anything, it's the most important email you're ever going to send anybody. Because if they open and click on that email, the likelihood of you staying in that inbox goes up exponentially because you as a sender and them as a recipient are teaching each other's infrastructures. Do you like each other? If it doesn't get opened, you're going to go to the junk folder much more often. So the reason I say that, that subject line that says welcome, that's very nice, but that treats the email almost like it's a receipt.

Jay Schewedelson [00:18:08]:
Like saying thank you, you need to say something super compelling to get it open from a technical perspective. So you want to say something like no thanks and something special inside or thanks, and you got to see this dot, dot, dot. Anything you could do to get that email open, that newsletter confirmation email, it'll keep that email in the inbox. So I think that's the first thing I would think about changing.

Pierce Uijainwalla [00:18:30]:
Yeah, I totally agree, Jay. We're all conditioned now to just be clearing our inboxes there, right? So like that welcome to me. I've seen so many bad welcome emails that I'm like, that's probably one of those. I actually think Tara did something really smart here in the sense that she's trying to get somebody to reply to the message because the j's point, that's what gets you out of the promo tab. But that's why, Dave, I know you asked about plain text to me, this one has a lot of good elements. Like, you sent it from a person, you signed it off from a person. But the banner, I would ask the question, does the banner actually add enough value for this to be an HTML email? If the real goal is to get people to reply to this email or to click a link, do you need that there? I did think the banner was creative. Like, I like the sauce reference to Chili Piper, and I like that you have the chili Piper logo.

Pierce Uijainwalla [00:19:33]:
But I would really test probably going full text only on this. And also, in my opinion, on the kind of like on the easy of the cheetahe would be to get rid of some of those links at the end and just have it like, hey, boom. Here's what I want you to do. Please reply. From my understanding, the biggest signal to the email clients is a reply. And so if you get that reply, you have a better chance of being in the inbox proper.

Dave Gerhardt [00:20:05]:
You like Tara, so it's a little bit better than normal, I would say here.

Pierce Uijainwalla [00:20:10]:
The other thing that's a bit tricky is I think some of these are forwarded emails. So, like, to me, when I look at this, kind of, some of the spacing between the paragraphs is a bit janky from a design perspective, but I think that's just the forward. So honestly, as a welcome email, I'm actually going to give this like an 8.3 because the goal and the intent of the email is there. I think there's just like a few sets. Yeah. Very much of Dave Portnoy's pizza reviews. And you gotta use the decimal system or it's a rookie square. Wow.

Jay Schewedelson [00:20:53]:
I don't know. I think I would go 8.2 just because I just don't like it as much as Pierce does. And the other thing I would think about changing is the high there. It's literally your first entree point into communicating with these people. And I know it sounds cheesy and weird, especially for b two B. But believe it or nothing, saying things like, hey, friend, or hey, go getter, or hey, anything that you think actually is cringey is probably what's going to do really well.

Dave Gerhardt [00:21:16]:
Hey, big dog. I like to say big. I like big dog. Channel my Scott Galloway. And every email, big dog, the dog.

Jay Schewedelson [00:21:22]:
Big dog. And Hanley says, hello, sunshine. Daniel Murray says, hey, bestie. The. It actually matters. You're creating your brand right out of the gate. So I would think about that too, but not bad. Not bad.

Jay Schewedelson [00:21:33]:
I give it a not bad.

Pierce Uijainwalla [00:21:34]:
Yeah. Yeah. Shout out to Zach. They're one click. Everyone knows the rules. Love that. I might take that.

Dave Gerhardt [00:21:41]:
All right, here we go. We got another one. This is from Neera. Dave is doing his best. I'm going to navigate. All right, so Nira, subject line, what do these three utilities have in common? Obviously we did the preview send, so tough to know the from name, but I think the point is general advice here and we're delivering on that. So. Hey will, here's the situation.

Dave Gerhardt [00:21:59]:
One of the following utilities is in a rural area. One is in a wildfire prone location, and one serves a major global city. Bullet point with a stat. Bullet point with the stat. What do they all have in common? They all use nearest 3d digital network platform. Something, something about the company, kind of like a statement and then leads to a call to action. This looks like an email that they would send to somebody, maybe open opportunity, somebody in the funnel somewhere trying to get them to read a case study.

Pierce Uijainwalla [00:22:24]:
I think that context is important because depending on when this is being sent, I think it could be a really good email for sure if it's an open op or you're trying to give data points on why you should work with them. I think just stepping back as like from just someone looking at this email for the first time, I find just the language makes me mentally really have to think about what's going on. I thought it was like a riddle at first and I was trying to solve it in my head. So I think, yeah, on the easy side, just making. What is it? What are you trying to communicate with them and making it, making them have to think, think less about what's going on. I like that there's one call to action. It's very clear what you want to get them to do. I would say that it would be awesome if the call to action was like a little bit more compelling.

Pierce Uijainwalla [00:23:19]:
How can we like spice this up a little bit? Not to use the chili Piper heat reference, but how do we get this like a bit more compelling and have a bit more kind of captivate in this? I'm not sure how much I want to click that button right now.

Jay Schewedelson [00:23:36]:
No, zero. I wouldn't open this or click on this. I'm sorry, I just wouldn't. I know that's terrible, but I'll tell you why. So it's almost like when you create this stuff, you're too close to it. I get it, you know that these three utilities have something in common. But how does that help me? You know, I see that subject line. I'm like, who cares? You know what I mean? And so I would almost think about it more like three utilities transform their operations.

Jay Schewedelson [00:23:56]:
What's the secret? So I can get excited about it. And then the call to action button, that is not going to do it. Read the case studies. Might as well say go get root canal. Nobody click on that. No offense. Well it is offensive. Im sorry.

Jay Schewedelson [00:24:09]:
But really you want to think about your call to action buttons. If you write a call to action button in the first person click through rates go up by over 20% because instantly the persons a little bit invested they may or may not even realize they are but they are. So instead of read the case studies its I want to see the secrets of how they transform their utilities. And you by the way can make your call to action buttons really long. They dont need to be two words or three words, it could be a whole sentence. So write them in the first person, get them a little bit more engaged. If you tell somebody, read something, register for something, download something, theyre like screw you. I dont want to do that.

Jay Schewedelson [00:24:43]:
Its save my seat, save my spot, give me the content. I want in. You got to reframe it. So thats what I would do.

Dave Gerhardt [00:24:50]:
What about the concept of just putting the content in this email? I feel like sometimes we over market like well if I put the case study button in there I can know that they click the case study button and that's an intense signal and I can measure that where like rational me is like but yeah nobody's ever going to click it. Why not just put that all in the content of the email?

Pierce Uijainwalla [00:25:09]:
My suggestion to this person and shout out to all the marketers who put this in because putting your work out there and getting people to tear it down is brave. So yeah, please take this as you apologize, find feedback. Okay, but what I want to say is really read each one of those three case studies and then if you were trying to tell like a ten year old about them, what would you say? How would you describe that story? And Dave, I love that point. Like put the teaser of that in this email and then have a button if they want to learn more about it. Break it down into human English that anybody could understand with like learn more here.

Dave Gerhardt [00:25:57]:
Nicole said the nice canadian teardown.

Pierce Uijainwalla [00:26:01]:
Yes that's it.

Dave Gerhardt [00:26:04]:
You guys want to give this one a rating? We'll move on to the next one. Is this going to beat 8.3?

Jay Schewedelson [00:26:09]:
No chance. I'll give this to 6.2.

Pierce Uijainwalla [00:26:12]:
Oh that's okay. I was going to go lower than that. I was going to go 5.1.

Dave Gerhardt [00:26:19]:
Oh, 5.1. Diana, put 5.4. All right. Nara, 5.1. We're here to help you step it up. Okay, next slide. Blue J subject line, June edition. Here's how I read this.

Dave Gerhardt [00:26:32]:
June edition. Exciting updates to ask. Blue J key events and more. Did I nail it?

Jay Schewedelson [00:26:37]:
Well, the first thing I say is the subject line. Here's the problem we need. Nobody should ever be putting the subject line, what the edition is. This is the 27th version of this newsletter. This is the June edition. Enough. Nobody cares, right? You want to put the topic of the newsletter, maybe a key stat, something. And here's the other problem.

Jay Schewedelson [00:26:54]:
When you say June edition by, like, June 5, it's outdated. So you are setting yourself for a massive failure. And then the rest of the words in there are just fluff. They don't mean anything. There's nothing in that subject lines going to get you to open it. But before I go into the rest of it, what do you all think?

Pierce Uijainwalla [00:27:07]:
I've just found it was pretty disjointed from the, as I skim through it, right? Like, there were multiple buttons. They're in different colors. It looks like chat GPT is, like, embedded some at some point. I think that's probably because you're trying to show, like, what the product does, but in the email context, just, I found it was a little bit confusing. And then if you go back to the human copy, when I read these two paragraphs and I read them a couple of times, you got to really work to figure out what they're saying. I think, taking like, a step back, what are you trying to say? What are you trying to get the person to understand from this, from the words you're using? But, yeah, I think this one, I would probably go back to the drawing board and just kind of actually see this. What's.

Dave Gerhardt [00:28:07]:
I see this all the time, this type of email. And I actually think there's actually a deeper root cause here. It's actually not that the email is not well executed. I know exactly what's going on here. This is a company, every month they do product updates. Every month they, they say, oh, we got to do our product update message. We got to write our blog post about the product updates, and we got to send the email out about the product updates. What are the product updates this month? And we send it.

Dave Gerhardt [00:28:33]:
I see it all the time. This is actually, like, my very first job working at a tech company. I was a product marketing associate, and my job was the release notes. And this is pretty much. What I would do is just write about it where it's just like anything in marketing. If we don't have a good hook, if we don't have a. Why you, why now? If we don't have a real story here, then we have no context. We don't have a good way to frame this.

Dave Gerhardt [00:28:53]:
And so I think Blue Jay needs to think more about, like, how do we use this as an opportunity? If we're going to send an email to our whole list right now, which they probably are, how are we going to use this as an opportunity to retell our story? Who are we for? Why do we exist? And why should you care about those things and then fit them within that frame? That's separate than, like, what Jay and Pierce might say about the actual design and layout of the email. But that's my kind of spidey sense about what's going on here.

Jay Schewedelson [00:29:18]:
First of all, I totally agree with you that this is somebody checking a box. They had to send the email out, and so they sent it out. But everything is marketing. And, you know, the other thing I would say is, visually, it's boring. What I mean by that is the paragraphs have, like, six lines each in them, and it doesn't matter what they say. They could say, here's the winning lottery ticket. You're going to be a billionaire. No one's going to ever read it and see it because visually, it looks.

Jay Schewedelson [00:29:40]:
It's like when you get a text from a family member, that's like a big block of text, and you're like, holy crap, I'm going to read that later because that looks like drama. I don't have the time for that. That's your family member. You'll read it. But when you get an email like this and it's like six lines in a paragraph, you're like, who cares? I'm not reading. It's visually boring. So you really want to limit it to three, maybe four lines with whatever you're sending out. Otherwise, people will not consume the content no matter what you're writing.

Pierce Uijainwalla [00:30:04]:
What do you actually want me to do? Do you want me to try it? Do you want me to read the product updates? Do you want me to book a demo? What do you want the person to do? Yeah, the strategy, but also just the cognitive load on the person to figure out what they're supposed to be doing is just too high.

Dave Gerhardt [00:30:24]:
Jeff wants us to eat a slice of pizza. After every email breakdown, I actually think that we're going to do another one of these in a couple of months, and I think we got to find a way to do that. We've gotten the crowd's responses here, and Dave GPT did a little bit of math, and the average rating right now is 3.3. So, Pearson J, either of you have a score that is higher than 3.3 for this email before we move on? Yeah.

Pierce Uijainwalla [00:30:48]:
And no.

Jay Schewedelson [00:30:49]:
No. Zero.

Dave Gerhardt [00:30:51]:
All right, thank you for coming out. Next, pleo. This is three financial trends to keep in mind for 2024. Light bulb emoji. Hey, Marco. It's clear that digital transformation is happening in a big way. And AI is shaping finance teams ways of working like never before. Not to mention the role of the CFO is evolving away from number cruncher into strategic partner territory.

Dave Gerhardt [00:31:14]:
Check out what speakers at beyond our european roadshow all about the new way of finance had to say about these key trends. Dig into these trends. Have a great day, team Pleo.

Pierce Uijainwalla [00:31:25]:
Let's start with the positives. The canadian niceness again here. I like the image. That's interesting. I feel like I don't know your brand, but it feels like it could have a good brand element to it. And then I think the button, dig into the trends has some good design. Like, I like there's kind of that retro font on it. The button isn't just like submit or register, it's you've put some effort into it.

Pierce Uijainwalla [00:31:55]:
So I'll start there. I think for me, the first thing that kind of short circuited my brain a little bit was when in the subject line, you say three financial trends, but then in the email, there's absolutely no mention of that. I don't know. Just right away I'm kind of, as an email audience member, I've lost some trust now in this brand because they promised me one thing, and then it's. There's not even a reference to it when I get to the email. So that's a bit of the harmony thing that I was talking about earlier. There's also just kind of, like, some typos or I'm not sure if a word is missing or something. So that kind of threw me off a little bit, too.

Jay Schewedelson [00:32:42]:
First of all, I don't think the subject line is terrible at all. I don't think the email is terrible. But you say we're getting these three trends, and then you open it up and, like, where are they? Do I have to dig through all this to read what they are? They should be bulleted out. And in that image, nice image. It's a meaningless image. I don't care if it's on brand or not. It should say some sort of big number three. Three trends.

Jay Schewedelson [00:33:00]:
You need to know something because it almost feels like the email doesn't match up to what they're promoting in the subject line, which is not that cool from a design standpoint. It's fine. It just doesn't say what it's supposed to say. And again, the call to action, I think, could be stronger. If you're going to have three financial trends and you're giving you a little bit of a peek at what they are, the button should be something like, show me the full trends report, exclamation mark. Get them excited to interact with it, but push the agenda of what you're promoting. Because I think it's like apples and garbage cans. It's two different things that they're doing.

Dave Gerhardt [00:33:34]:
Apples and garbage cans. That's definitely not the first time this guy's used that line. I love that. I think, like, you got to think about the purpose of the email, right? Like, if you have this great piece of content about these trends, the email is the delivery vehicle. How does the email walk people to get, you know, marketing is ultimately about the next step. It's like this endless funnel, right? It's like, my favorite copywriting lesson is, like, what's the goal of the first line of copy? To get you to read the second. What's the goal of the second line of copy? To get you read the third. If the goal of this email is to get someone to read that article, then you, you got to write this email differently and actually build up some intrigue and some mystery and do some things to lead them to that.

Dave Gerhardt [00:34:13]:
So, Pierce rating, I think this one.

Pierce Uijainwalla [00:34:16]:
Should be a 6.8, but it could be like an eight and a half for a nine with some minor changes.

Jay Schewedelson [00:34:23]:
I'm in the sevens. I'm going to go like 7.2. Why not? I'm feeling it.

Dave Gerhardt [00:34:27]:
Pleo will be reaching out to add you to their board of advisors. Jay, good work. We got two left. Let's try to do these each in, like, minutes. Ready, set this emails from ready, set. You're invited. AI and creativity and marketing partners or rivals. Bold move.

Dave Gerhardt [00:34:42]:
Right out of the gate with the double colon in the subject line. I'll let Jay take that in a minute. But hey there. Tired of the same old AI is going to take you. So this seems to be like a webinar invite. Jay, why don't you kick us off on this one?

Jay Schewedelson [00:34:53]:
Yeah. First of all, colon, the subject line for the win. You put a colon after the first word or the first two words, it will boost your open rates. A double colon is very rare. I mean, you really just don't see that. But I don't think they took advantage of what they're doing here, because when you open up the email, it says, AI is going to take your job. And to me, that's very compelling. So I would have a subject line that said, invited Colon.

Jay Schewedelson [00:35:14]:
AI is going to take your job.

Pierce Uijainwalla [00:35:16]:
Dude.

Jay Schewedelson [00:35:16]:
I'm opening up that email all day long, and that's what they're talking about anyway. And then when they get into the email, the thing that drives me a little crazy with any webinar invites is two things. Number one, how long is this webinar? I can't seem to figure it out. And if it's less than an hour, which is great. Okay. And if it's 45 minutes, they could drive home the point, we're going to do five things in 45 minutes, whatever it is. But I don't know how long this thing is, and I absolutely hate register now. That is the worst thing you could possibly put in an email, as far as I'm concerned.

Jay Schewedelson [00:35:44]:
It should say, I want in. Save my spot. I can't wait. Register now is like getting a colonoscopy, which is with the double colon, what this thing is all about.

Pierce Uijainwalla [00:35:53]:
Oh, God.

Jay Schewedelson [00:35:55]:
Sorry.

Pierce Uijainwalla [00:35:55]:
That's good. Good stuff. I actually really love the hook of this email. That's something that I do think is pretty captivating. I'm terrified of AI. So, like, I probably would go to an event about that. Ditch the webinar, you know, I think we get rid of that. It's going to make it better on the copywriting piece.

Pierce Uijainwalla [00:36:16]:
I also feel just that. Yeah, so are we could have been on its own line and it would have more impact and emphasis. Yeah, I think this one was pretty good. Agreed on the actual call to action copy, but I am not sure how I feel about the whole, like, sign up anyways and we'll send it to you. I've seen some people starting to test, like, there is no recording. Jay, I know you did that with the guru event. We all know how hard it is to get people to actually attend live. And I think that, like, these kinds of events with the chat, it's just so hard to replicate.

Pierce Uijainwalla [00:36:57]:
How many people have actually watched a webinar on demand? I can't remember the last time I did.

Jay Schewedelson [00:37:04]:
Yeah. And I think to that point, you know what? We're seeing a big new trend is this attend to receive, which is if you attend live, you'll get the special tip sheet. If you attend live, you'll be there for Q and a. That won't be in the on demand version where you have elements of content that only the live attendees will get. So this idea of attend to receive is really growing in the b two b space, which is getting people to show up more. It's increasing show up rates for these.

Dave Gerhardt [00:37:28]:
I think, actually think the offer is pretty good. It's a good hook for a webinar. Like, if this is your world and you sell to designers and creatives and talk about marketing, I think this is an interesting hook. I think the webinar offer is good. For me, the biggest thing here would just be the copywriting and how we could drive people to that actual session real quick. Ratings. Second to last one ratings.

Jay Schewedelson [00:37:48]:
I give it an eight.

Pierce Uijainwalla [00:37:49]:
Yeah, I was going to go 8.3. I thought this one was pretty good. I really especially like that image they have in the middle. Again, I think it tells you a lot without having to think about it too much.

Dave Gerhardt [00:38:04]:
Our last one, then we're going to flip over to questions real quick. Proceed. New webinar how to implement a change management office. Okay, I think this one's pretty self explanatory. Right out of the gate, it looks like just a straight up webinar invite. Now they're selling to an industry that seems to be a little, well, actually they sell to cmos here it looks like. Right. Register for proceeds.

Dave Gerhardt [00:38:28]:
Upcoming live webinar discover how effectively implement your cmo design while overcoming typical obstacles.

Jay Schewedelson [00:38:33]:
So I think they're selling to nobody with this email, I'm pretty sure.

Pierce Uijainwalla [00:38:36]:
Yeah.

Dave Gerhardt [00:38:36]:
Just, there's a lot of jargon. This. This is, unfortunately, when I think of b two b marketing in my head, this is what I see.

Jay Schewedelson [00:38:42]:
This is a no go for me, like zero burger.

Pierce Uijainwalla [00:38:45]:
I can almost picture what the webinar will be like by looking at this.

Jay Schewedelson [00:38:50]:
Yeah, I mean, a lot of power. Insomnia then. Yeah, the webinar's gonna crush it for you. But seriously, I mean, this is not gonna do it. You gotta really kind of rethink the imagery, the words, everything you're doing here, because it's just like you said, it's telling you what it's going to be like. It's going to be. I don't think I really want to attend this thing. And that's not what you're looking for.

Dave Gerhardt [00:39:07]:
Yeah, I think it's just got to rethink it from the beginning. How are we going to. This is where I love me some Gary v. And I love when he talks about empathy and understanding. Like, can you put yourself in your customer shoes? Or the recipient of this message is shoes. Like, out of the 59 new emails you're going to get in your inbox today, are you really going to open this? Are you really going to read it? Are you really going to click and register for this thing? Probably not. And so let's rewind back from there. It's not even an email design thing.

Dave Gerhardt [00:39:35]:
I think when we have new webinar in the subject line, it just means that we haven't thought about what it takes to compete for attention in somebody's inbox today.

Jay Schewedelson [00:39:45]:
Agreed, by the way. And we know in the subject line the word webinar, it will depress performance dramatically. What you want to talk about is the topic that you're going to talk about, like how to implement a change management office. Then you open up, oh, it's a webinar, fine. But webinar is the same thing as ebook. Nobody cares about the vehicle, they care about the topic. So when you say ebook or webinar, you're basically saying boring colon. This is what it's about.

Jay Schewedelson [00:40:08]:
So lose the vehicle.

Dave Gerhardt [00:40:09]:
Robert, I would just wonder like how, what are the results to this? You know, I'm open to this being wrong. I would be surprised if this was a high performing email and driving a lot of registrants. And I think you can just, you can kind of work backwards from like, yeah, are we even driving people to this webinar? If so, if not, we gotta, we gotta change the delivery here. And so I would start with the hook, start with the copy. This one is less about changing the, it is less of a design thing and more about the, like, what are we actually sending in this email? Is this, is this content that's going to land with this audience? I'm going to stop sharing here. We're going to skip a rating on this one. I think it needs a bunch of work and I think that's clear. I want to get a bunch of these questions.

Dave Gerhardt [00:40:46]:
And while I look for this, I'm going to summarize this one. But Jay, this one's for you. You mentioned sending from different, from names. There was a question. I actually thought of this myself too. Didn't the school of thought used to be, or maybe did something change that? Like, it's better to send from one consistent name over and over to build up that credibility versus switching it around in the inbox? Did something change? Is this a newer opinion or just maybe you can shed some light on that?

Jay Schewedelson [00:41:10]:
Yeah, this is really something that's evolved over the last two years and you're still keeping the core of your brand in there. So if you're Acme, it's, you know, Acme events or Acme, FYI, if it's the newsletter or Acme, don't miss, you still have that brand element or gen from Acme. Right. But delineating what it's about and getting people interested earlier on, you're winning that inbox battle because only about 20% or so of marketers are using the from name to delineate what it's about, which is why is it standing out? And if you see what's going to be happening when iOS 18 hits from Apple this fall when they update their mail app, okay, they're actually going to be removing the pre header from the way that emails are going to be viewed. So now all you're going to have available to really get that email open is going to be your from name and that subject line. So I think that from name usage and how it's being written is going to become more of a thing, not less, between now and the end of the year.

Dave Gerhardt [00:42:05]:
Pierce, on multiple CTA's in an email, there was a question about that. Do you always recommend one? Is there ever a time that multiple CTA's is appropriate? Can that ever work?

Pierce Uijainwalla [00:42:17]:
Yeah, I mean, there's always exceptions to every rule. I think it goes back to what is your goal for the email? Right. And starting from the goal, if your goal is to drive as many webinar registrations or live event registrations or streaming or whatever we want to call it, then yeah, have the one CTA, depending on the email, maybe there's like an event that you're hosting, but you have a very relevant piece of content that could be applicable to people going to that event. It's like, hey, come and see us at Dreamforce, but then also hear the top ten things to do at Dreamforce. That could be something that you include both in one email. But I think general rule of thumb is less is more. I always talk about the in and out menu compared to the cheesecake factory. You don't want to be a cheesecake factory menu with your emails.

Dave Gerhardt [00:43:16]:
It's my, I use that analogy all the time. And then sometimes people like, hey, but I like, I like the cheesecake factory. And it's, yeah, it's fine.

Pierce Uijainwalla [00:43:23]:
They have like 37 types of hamburgers.

Dave Gerhardt [00:43:27]:
Yeah, you can get it on a pizza, you could get on a cheesecake. Uh, this question's from Caitlin. Thoughts on the email coming from a person at the company versus the company name? This was the most upvoted question in the chat.

Jay Schewedelson [00:43:39]:
Oh, well, I think person from brand. Right. Jen from Gong or Dave from exit five is an absolute win. It does incredibly, incredibly well because it creates that direct connection with people. So if you haven't tested that, you should. And that doesn't mean you're changing the sending email address. You're just layering in that person. And then when you open it up, it needs to continue to be from a person.

Jay Schewedelson [00:44:03]:
It can't be like Jen from exit five. Then you open it up and it's like generic webinar invite. It needs to still feel one to one, so you got to carry it through. But it is a crusher. It does so well.

Dave Gerhardt [00:44:13]:
This question's from Amanda, maybe, Pierce, you'll have some thoughts on this. Do animations and I guess images would also fall in this bucket. Do animations and images make it more likely to get caught in spam?

Pierce Uijainwalla [00:44:23]:
It's a good question. I'm not going to pretend to be like a spam trap expert here. I think it's a trade off, like anything, right? If your images and animations are going to increase your engagement rate, then maybe it's worth the spam hit. If you're finding that that's happening, from my understanding, I don't think that plays a big role right now. But if there's any experts out there who can prove me wrong, let me know. I genuinely, like, want to know the answer to that.

Dave Gerhardt [00:44:54]:
There's a comment in chat says, no animations. Don't make your email, go to spam. It's bad links, poor sending reputation, no engagement, and poor list management that leads to spam.

Pierce Uijainwalla [00:45:01]:
Here's one thing I would have one tip about animated gifs that I don't think everybody knows is that in some email clients, they only play the first frame of your animated gifs. So that's something that you really need to check because it can be an unfortunate frame depending on what is happening in that animation.

Dave Gerhardt [00:45:24]:
All right, well, Jay has disappeared off into the night. I'm here, Pierce is here, but we're going to wrap up. So I asked, this is your turn to tear us down or build us up. Leave your rating for us in the chat right now. We're going to hang up in two minutes. But, uh, did we beat 8.3? Was this a 3.4? Was this an 8.3. Put it. Put it in the chat.

Dave Gerhardt [00:45:39]:
Alex says we're ten, so I'm going to hang up before anybody else can get off. Right now, a bunch of tens, a twelve, nine, a 25. Crank it to eleven. So anybody who's going to give a poor rating now just. We've already been drowned out by, like, ten, nines and tens, so. Very good.

Pierce Uijainwalla [00:45:54]:
Look at all these gifts.

Dave Gerhardt [00:45:56]:
And you heard me. That's a hard g. That's a hard gift. Pierce, thank you for doing this. This is awesome. Pierce is the founder and CEO of a great company called NaC. They're a sponsor of exit five, one of our partners for this year. And, uh, we've been in the exit five chat during this, just saying how awesome this was.

Dave Gerhardt [00:46:11]:
And we are already ready to run it back and do another email session. This was really great, Pierce. Enjoy the rest of your day. Thanks for hanging out and everybody that took the time out of their day, there was 346 people was the max that I saw live here. Awesome. Thank you for coming and hanging out with us. If you're listening to this on the podcast later, you can go find the recording on YouTube so you can see the emails and everything. Other than that, we'll see you on the next thing that we do here at exit five.

Dave Gerhardt [00:46:33]:
Check us out. Exit five.com dot. Go check out NAcDa and we will see you later. Good job, everybody. See you later. Exit.