B (3:13)

Welcome.

C (3:13)

Welcome everyone. Welcome to Exit 5 Live. I'm Jess Lytle, I'm the head of marketing here at exit 5. Actually stepping in for Dave today, so go easy on me. He's out. He's actually recovering from kind of a major hip surgery. So there's going to be no peloton in his near future for the next couple of weeks. But I promised him that I wouldn't, wouldn't break anything on here, so we'll see how it goes. But if you're new here, we, we do these free live sessions like twice a month. And before I actually joined Exit 5, I was a guest on one of these webinars myself and they're pretty cool. I was actually showing an ROI tool that I built on Lovable. But they're really fun. They're just really like conversations. They're unscripted. There's real operators on this call who are in the trenches kind of doing the work every day. So really here they're just here to help us get smarter, have a conversation. Maybe you learn something, maybe you walk away with like a moment where you're like, oh, that's great. I want to do that. I want to take that back. So I know selfishly, I'm also excited to learn to improve some of the email strategy and Systems here at Exit 5 as well. So, so welcome. This conversation is all about messaging. Email, SMS in app messaging, what's actually working this year in 2025 through 2026? Because as we know, email isn't dead, right? People are making this work. Messaging isn't dead, bad messaging is. And AI is making that a lot more scalable. So the bar for attention in the inbox today is higher than ever and I think we can all feel that. So thanks for being here. I'm also just going to do a quick read for our sponsors here. So thank you to Customer I.O. for sponsoring today's session. If you haven't used it or know of them already, they're one of like the OG OG data driven messaging platform. So turning your customer data into personalized messages across email, push SMS and in app. So it's really great because it gives us as marketers that control so you can really kind of create and change your messages on your own. You don't need to like bug your dev team or engineer to help. Actually in my last role Prior to joining Exit 5, I used Customer IO. I was Director of Demand Gen at a PLG vertical SaaS organization. That is actually a lot of little terms there. But our team used customer IO heavily. It was actually really great for our 30 day trial onboarding flow. Everything was kind of triggered off of user behavior which was great and really helpful. So that really kind of behavior LED flow didn't really make it feel like marketing. It was more like they'll be being guided through. So the timing, the relevance and the messaging was kind of the secret sauce there. So really cool. Great for smaller big teams. So huge. Thank you to Customer IO for supporting these sessions and check out their website Customer IO. All right, let's introduce the guests on this call. All right, here's our panel. Amazing group today. I'll just have everyone do a quick intro on themselves. Let's just start with Gabby and then we'll go to Alyssa and Joe.

D (6:11)

Jess, thanks so much and the Exit FEM team. Thanks so much for having me and.

C (6:14)

All of us here today.

D (6:14)

My name's Gabby. I'm based in New York City. I have been at Customer IO now for about six years, working in lifecycle marketing and growth marketing. So I cover our onboarding and activation series for our users.

E (6:25)

My name is Alyssa. I run an email marketing agency. I help with email and SMS for D2C and B2B brands.

B (6:31)

My name is Joe Cunningham. I am an email marketing consultant and copywriter and I've edited hundreds of emails newsletter ads for Stack Marketer, which is a digital marketing newsletter and also works with SaaS and tech brands with event emails and some cold outbounds and some like conjecture stuff too.

D (6:53)

Nice.

B (6:54)

And I'm based in Michigan.

D (6:56)

Awesome.

C (6:57)

Yeah, we have folks from all over. I'm in Tampa, I think. Alyssa, you're in like outside of Seattle. Gabby's in New York. Let us know where else everyone else is. It's around lunchtime for us, but awesome. Thanks for those intros, guys. All right, let's get into it. So these, if you haven't been on one of these, like live combos before, they're really interactive. So drop questions in the chat as we go. I'll be watching that like a hawk, pulling questions into the conversation. I think we have like over a thousand people on this, couple hundred live already, so please ask away. All right, I will kick us off. So email is dead. Everything's dead. Alive is dead. I love that comment. Nobody reads anymore. Nobody does it. Right. It's not. It can't be true. Right? Like, so we know we've heard these things. But the truth is though, that AI has really has changed the game a little bit.

E (7:45)

Right.

C (7:46)

It's really kind of changed how we stand out in the inbox. I think most folks recognize that there's a lot of AI being delivered to us in our inboxes and it's hard to kind of sift through the signal from the noise here. So I think we could just start with like just a high level kind of thought here. And how has this change, like, how is the messaging changed this year? You know, what's working?

D (8:11)

What.

C (8:12)

What are you doing? I mean, Joe, you mess. You mentioned, like messaging. Do you want to kind of kick us off on. On just your thoughts on like, what is changing with messaging right now?

B (8:22)

A few things I've noticed. This isn't like messaging per se, but it is related. I'm seeing more and more. I almost feel like the email inbox is becoming a bit more of like a social feedback. I'm seeing more companies sending emails from team members. So it's going to be the name of the person and the sender and there's going to be. They often have a sign off or some kind of a signature at the end of the email. I'm noticing for myself. I almost instinctively look for names in my inbox and not so much company names. So I see Mark Huber's emails from User Evidence and I'm like, oh, sweet. Like, I like work, like, I like reading his insights. I see Kaylee Edmondson from Demand Loops and I'm like, oh, Kaylee's Awesome. I love her.

C (9:10)

I mentors too. Yeah.

B (9:12)

Yeah. So like I think that it's related to messaging in the sense that messaging is still coming from the sender is just as important. The person who's delivering the message is just as important, maybe even more so. Now another thing I'm seeing is the teams and the companies that seem to have the best grasp of their icp. It's clear they know who they're talking to. It's clear they understand the problems that they're solving or that their company solves. It's like they're putting in the work to make their messaging actually quality. I think that's pretty apparent. The weasel words, the ad speak, things like we've got you covered. And that kind of messaging I just don't think lands anymore. It's brutally obvious that if it's not AI, it's just not. There's not a lot of ICP depth in terms of the research and the copy there.

C (10:05)

Yeah, looking for like you're like looking for the human. I've noticed that too with like having even just a photo and adding that to your, your CRM systems. We did that with the prompt. But like you'll see if you scroll through your inbox, some people will have a photo there and some people will just be like nothing or like the company logo and that, that could be like a big teller and you. There's a good question here from, from Rachel, but are they actually being sent by that individual? Like do you know Joe? Like is there, is it just like are they. Is it going directly back to the sender? Is it like ghost written sent from the map? Like do you know if they're sending or it just looks like it's being sent from someone else?

B (10:45)

I mean it looks like it's being sent from someone else but usually it's, it's automated, it's ghost written or whatever. But a lot of companies are. It's. I do see some companies that will, if you were to hit reply the email would actually go to that person's address, which I do think is kind of like the next level up. If you are, if you're able to do that, if you're willing to do that or able to set up some kind of routing system so you kind of like filter out the out of office replies and stuff like that. Like if you want email to be that kind of, to feel like that one to one channel and to be that, that relationship builder, that makes sense to me. So. But I am seeing a mix some People still use general inboxes. Some people are using actual team emails.

C (11:25)

Yeah, we get all of the replies so that the whole Exit 5 team can see them for. For all of our emails. I know that also helps with deliverability. So that's a good hack, just asking everyone to reply, but then actually have that somewhere where you could see it. There's some really awesome responses sometimes and make it to where someone actually could respond to. What about Alyssa, Gabby, you guys thoughts on just messaging and how that's changing this year? What's working? What's. What are you guys doing there?

E (11:54)

Yeah, I think just to add to that, really you tapped into something, was saying, like, finding the human in it. The inbox is like a personal space. And anytime I'm writing an email, like, not to get too existential for a second, but really, like, look at it as someone invited you into their inbox. Like, I'm going to treat that with respect. Like, they've invited me into this place to have communication with them. Yeah, I'm going to treat them like an actual person. Try to filter your emails through that. And so with that perspective, I think too, taking it a next step to be like, how can I define my role in their inbox? So if I am this person, something good with a client of mine is like, we made all of the emails come from the intern, and then that was like, his role in the inbox. So you knew you were getting messages from someone who was, like, testing things out and kind of fumbling and learning their way along. It almost created this story narrative between these emails. Even though the emails themselves were just like plain text reaching out conversations, it really gave him, like, a distinct voice. So you were like, wanting to opt into this story, almost like an ongoing podcast or audiobook, like you're wanting to opt into it. And then with that, like, really shifting attention, if you have the ability to. To asking for more replies, like getting people to engage with email in the way that it's meant to be engaged with.

C (13:05)

Yeah, love that.

D (13:06)

By the way, my WI fi at work is like, suddenly getting a little spazzy. So I drop off, of course. But to add to what Alyssa was saying, and I mean, from what I've seen, if you work Alyssa, you're really good at this human tone of voice. But I think what makes each marketer's contribution unique is that at some point all the LLMs will sound the same because they have so much similar input. And even if you say make it casual, like make it friendly, it will still sound similar to what everyone else is doing there. So I think what each individual person, like, on this call can contribute is their tone of voice, which only that person can write. And that's what I remember. One of my coworkers was at a talk like, a month ago where someone said, like, their best practice for email is like, like pretend like you're writing to your best friend. So I think, like, and each of us would address, like, our best friends in their way. So I think that's something very powerful that can still send out in the inbox even in the age of, like, LLM generated emails.

C (13:54)

Yeah. Somebody asked here, Maria, how do you balance, like, what company stakeholders are asking you to include in, like, emails, newsletters. I'm laughing. Also product feature updates, announcements with what you think will be actually useful.

D (14:09)

That's the hard one.

C (14:10)

To the death.

E (14:10)

No, I'm just kidding.

C (14:14)

You block them and ignore them.

E (14:18)

That day.

B (14:22)

We don't do that here.

D (14:24)

Yeah, I mean, also, Maria, but I think that, like, it's. It's a fine line depending on, like, the state of. I mean, not politics, but like the state of, like, what's going on at the company at the moment. No, like, you have to kind of. You need to know how to nurture your relationships with other orgs, but also be like, hey, if we include the nine new product releases this month, literally no one will have read about any of them, you know, So I think you need to step in as the expert and be like, hey, I know that we should include more than three product releases because no, like, science says that no one will read longer than 10 seconds of this email. You know, So I think you need to be stacked by religion management, but also, like, be the expert that you are in your space.

B (15:00)

Oh, and I think to kind of add to that, Gabby, like, part of that. Yeah, part of this. Like, I had this with a client recently where they had a event, they had a conference coming up and their CMO wanted to send out emails that were basically saying, hey, our team is going to be there. Like, you should come too. And they were like, okay, so how do we write this so that it's actually going to be meaningful? I think that's kind of the challenge for we marketers. That part of it, there's always going to be an element of that and sometimes there can be. There's going to be a part of you that's like, oh, man, we shouldn't really send this guy on email. But they kind of have to. But I think there's a unique challenge there in that that's kind of the story finding part of marketing is there is a story there, There is probably a way you can connect that product update to that, to that recipient, but guiding your team to think in terms of the segments you're sending to. So we're not just going to be blasting this, everyone. Relevance is everything in the inbox now. So sending it to the right people and like, we could send this product update, but we're going to send it to the right people and we're going to tell the story about this product in the right way. So it actually shows that, hey, here's how this makes your workflow better. Here's how this helps you get from A to B. Yeah, I think that can.

C (16:19)

It sounds so simple, but sometimes, like, we forget as marketers, there's just like humans like you and I opening emails on the other side reading them. So, like, why would they want to read that if it's just a feature update that doesn't offer like a helpful use case or like a value point to them? Like, is that really helpful or is it just us pushing the message we want to push and hoping that it triggers something from them to do? Right. So sometimes it's just like going back to the basics and thinking about who's on the other end receiving that. But I think relevance over volume is critical right now, especially today with AI. But, but yeah, death to blasting, as they say in the chats. That is the thing that does need to be dead. Even us internally at XO5, we're working constantly to try to improve the way that we're communicating with everyone. And I think that there's always some place that you can grow and improve in these things. Speaking of AI, let's move on to that layer of this because I think it is really interesting to hear how different marketers are using AI, whether it's for like, personalization, like, what part of the journey is it being used on? Is it like the personalization aspect of it, the testing aspect of it, or the send strategy that's, you know, AI is involved in that mix. Gabby, you look like you were nodding like you had something good.

D (17:40)

I was like, alyssa, go. Okay, so, well, okay, I'll try and speak quickly. So the thought I had was, Joe, I saw that in, like, in some of your portfolio work you've implemented, like Singulate, AI is like, presumably AI feature to kind of pull in business. Yeah, Business name, probably use case to like, use some personalization and open and copy. So, yeah, we've, we've Also had like some success with that at customer IO where like it increased engagement for users in trial but not as much I think success as you saw Joe on revenue. So that was making me think so like for example, you're using Singulate AI. We were using like an end to end workflow with API calls to ChatGPT to be like hey, use our data enrichment workflow that we already have going for our sales tools to like bring in some information and like guess how this person would like to be talked to given their role on LinkedIn if it's available or whatever. But I saw that like Joe's campaign had a lot of revenue impact for like a cold, a more cold like outreach sort of sales. If that's, if I'm describing that right, I'm just the looming that was on your website whereas ours where they were already users and had already opted into the free trial, it drove high engagement not but not so much free to paid conversion. So I think that for sales like more BDR, like BDR 8 outreaches, there might be some really good like LLM enrichment text use cases. But anyway, I don't know if Joe or Elizabeth, you want to talk to that a little bit more because for us it's been like high engagement for our trial users but less revenue driving and like hard to implement.

B (19:01)

Yeah. One of my clients is a, is a company called Singulate. They're like an AI personalization tool. Yeah. So for another one of my clients, I helped them use Singulate and we sent an email to a list of. They were a list of potential sponsors for the newsletter, people who had expressed interest in advertising. And one of the things we did was we personalized elements of the email body itself so that it would show like the intro would speak to, it would share an example of someone in their space, like in their vertical or had a similar business model who had run ads before and saw decent results. And then based on the industry they were in, we would show the relevant like logos that they would either find like compelling or, or like another relevant mini case study. And then we also had a, a part in there that spoke to their growth stage, where were they at in terms of their, their company size or company growth. And that was also a personalized section of the email. So each email that every contact got was slightly different. So that's like one, that's like one way that you can, there are AI tools like that can help you really personalize the messaging and make it a little more relevant to that contact and their circumstances and the signals you had from them and so on. That's part of it. I do think, speaking generally to AI email workflows, it's never going to be perfect, right? Because kind of like Jess was saying a lot of these LLMs for me, it was Lizza, I can't remember who said this, but a lot of the LLMs, at some point, if you're using them, that kind of weak generic phrasings and those weird structures, like, that's going to slip in. But I do think it's helpful to almost think of your content as data. So if you're building a content workflow for your emails to make sure the content you're training your LLMs on is as high quality as possible, it's like very strong human voice, really strong stories, case studies, data, like, whatever you're able to train your own workflow on, it's going to help you get better outputs and then training your models that day for like your email specifically, if you're doing a newsletter, for example, like, one of my clients put together a series of pro of workflows where they had each section of the newsletter produced, like section by section. So it's not like a total newsletter all at once. Each section has its own strategy, its own purpose. And so you're like developing a main workflow for that section alone. And you get much better outputs that way. And then the last stage is you do have that human editor, the human in the loop who like reviews the whole thing for not just accuracy, but also for tone, for structure, for strategy, making sure the email, the newsletter, whatever it is that's going out, is it optimized to perform as much as possible based on that particular campaign, that particular audience, so on, and then also adding in those little like, kind of like, I kind of think of them as like spontaneity elements where you're adding like, like that, you know, that GIF or that like office reference or like whatever it is, like that, you know that, that final human touch that it does feel a little spontaneous, a little natural, feels like it's coming from a human, feels like it's coming from someone at your team who's just like, oh, this, this kind of thing like happened today, we're talking about, let's pull that in. So I do think you can kind of like you can use AI to help you personalize your emails, which I think is really, can be good for outbound, where you need that. It needs to feel researched and it needs to feel relevant because it's no context, it's coming from a rando. But then there's like LLM, like the randos. But then there's the LLM, like workflow side for your own team where you're trying to. You want to make your content more efficient for your emails, but you still need that kind of balance of, like, authenticity and quality.

C (23:00)

What about optimizing for subject lines too? You know, trying to get like, those open rates up, you know, anything kind of beyond just generally personalizing. Like, this is something I'm really working on right now for our newsletter. My first newsletter ever that I'm writing and that's. It seems so simple, but it's like the subject line and the preview text, I feel like are so important and there's. It's hard to get that down.

E (23:26)

Yeah, I think we lean a lot into too, like, your. Again, going back to, like, who you are in the inbox. Because I've noticed, like, take a step back for a second. If you notice your own scrolling patterns, like, when you go to open an email, stop and think, like, what made me open this email?

C (23:41)

I just started doing that. Sounds. Yeah, I'm like, why did I not read this?

E (23:46)

It's one of three things, right? It's a subject line. You're either like, that's golden. That's totally me. It's the sender. So you're like, I'm going to open this no matter what. Or it's the time of day and you're like, I'm kind of just opening emails right now anyways. And if you're having struggles opening emails, you can kind of lean into those three strategies too. Like, know that you have more available to you than just subject lines. But also, I think it's a really good practice to lean into, like, when you're opening emails, what's making you open it? What subject lines are really capturing your attention. Start taking note of that and then see how you can implement it. But then taking that a step further and understanding who you are in the inbox. Sometimes I've noticed really short subject lines that, like, don't make any sense. There's certain people I'm totally going to open that for, and there's certain people where I'm like, this feels off brand. I don't like that. This feels gimmicky. And so kind of again, like, developing your inbox Persona, knowing what people are expecting from you and then really leaning into that character.

B (24:38)

Yeah.

C (24:39)

Yeah. All good points. Actually, I'd love to go, like, super tactical for a second too, on this is There anything that like you could think of top of your head recently that was a campaign like this or like an email like this or like a subject line or something that like worked way better than you thought. Like why? Like I could start with one. There was an email, a newsletter that went out for Exit 5 and I call it like our viral email because it had we'll get replies all of the time, but this one had like, it was crazy. It was like 20 replies within like the first like 10 minutes it went out and then they still came in over weeks and it was like, it was really punching on like the human connection part of it, like the empathy part, it was the story in it. I think that really resonated with folks and like their, their day to day. It actually had nothing to do with marketing also, which is interesting. This is a marketing newsletter from Exit 5, but it was about like, how are you managing your mornings? How are you not burning out? Here are some like things that I'm doing that aren't like the things you, you've heard of a thousand times. And then folks were replying like, wow, this really hit. Or like this is how I'm actually doing it or I'm going to try this thing. It's kind of, kind of just. But it was like, you know, it was just, it was cool to see that too, that resonate. So sometimes maybe not even the things that you think that will resonate, but that, that human kind of empathy story part. Anyone else?

D (26:01)

I'll jump on that example, Jess. Oh, and say, I'm sure many people here subscribe to Lenny's podcast newsletter and I personally have like real. I subscribe because I'm like, I need to know what he's talking about. But I do not open his emails. I'm like, I can't read another AI foundation story. But he sent an email this morning. People have seen about like his Christmas tech recommendations. Black Friday is coming up. I was like, wait, I got to see what he's talking about. Because I don't want to hear another unicorn story. But I do want to know what Christmas gifts he's recommending.

C (26:27)

Interesting.

D (26:30)

Taking a beat and like doing something different or more human or that's like, yeah, interest of your audience.

C (26:35)

Yeah, mix it up. Because like, we all know our ICPs are well rounded human beings, right? They're subscribing to your newsletter because they want to read about the thing. But they also have other interests that we probably know what those are, right? Like book interests or like what does your ICP typically engage in outside of work and how can you provide value for them in that way? So it kind of mixes things up a little bit and humanizes your brand a little. Yeah, it's kind of like LinkedIn posting. You kind of got to do the same thing, right? Like some personal with some. Some top 10 list.

D (27:10)

Mix it up.

B (27:11)

Yeah, totally. That kind of stuff is probably, it's probably worth adding to your. Your like ICP documentation, your Personas too. Every time someone in your like responds to an email with something and mention something that they're into or whatever, like add that to your documentation that being content influenced in the future. That's really good.

D (27:33)

Yeah.

B (27:34)

You guys, you do that quite a bit. Or like Dave, Dave does that quite a bit. He'll talk about like parenting and. Absolutely. I'm a parent, I work out, so I'm like, oh yeah, like that. You know, I get into that.

D (27:48)

Yeah.

C (27:48)

And it inspires you to do that too, you know, to do more of it. It's not always just like the same story. Yeah, cool. I'm seeing some really cool. Let me look through these questions in the chat. Go Canada. Great newsletter there was good. Oh, here's an interesting one. Do you have any advice for. And they're all interesting, but this one's standing out. Do you have any advice for cold sending domains are subdomains a hundred percent safe for protecting the main domain.

E (28:17)

You definitely want to try a strong warmup strategy.

B (28:21)

Yeah.

E (28:22)

Weeks sometimes.

C (28:23)

I know that inboxes are. They're getting a lot tighter on. On like all of this too. And like you'll find your, your email showing up in promotions chat, which what, like nobody checks? Maybe like once a year, if that, you know, before they delete them all. Yeah. Any thoughts on that? So warming up the domain first.

B (28:42)

Yeah, definitely warming up the domain. And this is like, I don't know, this is tangential related but I would almost like even before you do that, I don't know, I would almost suggest like make just make sure that your audience is actually like make sure you understand how your ICP uses email. Maybe it makes more sense to do cold outreach somewhere else like LinkedIn.

C (29:06)

I don't know, maybe email isn't the channel for that. Yeah. Is finding emails a better assist channel these days? Especially these days, like assist channel or closing channel.

B (29:17)

Oh, that's a good question. I think it really depends. It does seem to depend on the client and their industry. And like what also what their offer is. You know, like the offer is such an important part of Every email you send, like what are you like asking for a meeting isn't really an offer. So like I think there, I think there are a lot of elements that go, go into that but I do see, I am seeing like, like there's, there's an email marketer, Tyler Cook. I think he's on this call actually shout out to you Tyler. He does a really nice job of like blending email and LinkedIn. So he's, he's like inviting subscribers to join him and connect with his team on LinkedIn as well.

C (29:55)

Okay.

B (29:55)

Eddie Schlater, Eddie Schlanger, who's a fantastic copywriter, he does the same thing. So I do think that the email, if you're going to do like cold email, consider doing, consider not treating it as a, like, you know, operating on its own in a vacuum. Because keep in mind too that if people do get cold email and it's interesting, they're probably going to look you up. So they're probably going to want to see like, all right, who is this? What's their company about? They're going to want to see that kind of proof and any, that, that social presence is going to help you build that proof. So being in, you know. Yeah, numerous places, not just email, I think can, can help.

A (30:36)

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C (31:47)

Yeah, that's kind of the, the multi, the multi channel strategy. So I mean hopefully nobody's relying on just one channel. But are you, how are you guys all thinking about email vs SMS? When to use it, when to use each vs like in app messaging, when does each matter? Is there a right orchestration? I know it depends on a lot of factors. Maybe we, maybe we have specific examples of like hey, this is when this works well when you've got this type of business or this type of vertical. But is there anywhere, Gabby, do you want to jump in? Because I know that that's like a big kind of value point that you could do with with customer. I o too.

D (32:24)

Sure. Yeah. So Customaryo does offer like. Yep. Push in app, email, sms. We personally only use in app and email because we don't do SMS direct messaging because we're B2B SaaS and we don't have mobile apps. So no push notifications.

C (32:38)

That was a question earlier is like should you do SMS for B2B SaaS? So you, you're like, you're thinking this isn't the right. Nope.

D (32:45)

Yeah, people love debating it. I'm sure everyone on this call has hot takes. Yeah, A lot of people are like absolutely not like but never, you know, the phone is sacred anyway. So there's a.

C (32:56)

Depends on the ICP too. Right. But yeah, so it's hard to always have like a general like yes or no but probably for the majority of the time. Yeah. Yeah.

D (33:04)

I personally would not love to receive work related texts on my personal phone but I'll just say that when I'm working more with like activating, trying to activate like users who we see like are in danger of churning or whatever. Obviously the move there is not to do in app you should do email because they're not logging into your product. So like you need to try and get them back in like an email and that's hard. We're still trying to figure out the recipe there of like people are opening all these emails but they're not taking the action I want them to take. So why is that? But yeah, I think it depends a lot on where they are in the user journey. If they're already active in your product, hits up with in apps and if they're new. But if they're not active, obviously email is going to be better.

C (33:40)

Yep. That's when we used them to that first 30 day like three free trial that we did. That's when we would do some. So maybe some in app helpful nudges on on hey, try this. Or here's a video to help with this. Slow. And then some emails connected to that too to get them from, you know, free trial to activation. That's good feedback. Jud, you gotta get that call.

B (34:01)

So sorry about that. It was spam too.

C (34:03)

Totally kidding. Can we have some tips on how to remove our cell phones from. Because I get 40 of those a day. Cold call.

B (34:12)

I've got so many calls and I still get them.

C (34:15)

I don't even. Yeah, I think I block all calls that aren't saved to my contacts. But anyways, yeah, good stuff. Alyssa, do you do any SMS and with any of your. Okay, how, when, where do you wear and when.

E (34:28)

Yeah, I feel kind of similar to what Gabby shared. I think SMS really strong utilization if you have like something that's urgent. So for brands that are in D2C, more like if you're having a sale, sometimes educational can perform but really what I think you need to think about is like yeah, people are opening email on their phone for sure. But if there's a time where they're specifically going to be on their phone, we might lean more towards SMS or in app because those are most likely to be open on the phone. If they're more likely to be on computer and you want them to scroll and do a lot of clicking. If you want them to do big screen work, then email can sometimes provide more of that space. So think about like what the CTA is where you're calling to next and then help work backwards. Like what's going to be the best form to communicate that then like what's most likely to get them through. If I want them to engage on the app on their phone then I'm going to try to engage them on their app on their phone so they're not pulling out an extra step.

C (35:20)

Yep, true. I wonder, would anybody be mad if we if Exit 5 sent texts to people? Maybe as like reminders for live meetup events or if you're signed up for one already maybe that would be helpful if you're like hey I want to go to this New York event and you get a little text like it is tomorrow or if like we include yes, free pizza for sure like free apparel spritzes or something.

E (35:41)

I also think adding things like the address people can just click to like their Google Maps opening up. That can be really useful.

C (35:48)

Okay, yeah, something like value that adds value, not like just a spam. Yeah. Okay. Somebody said if it was a Dave bot. Yes. Maybe we'll just have Dave randomly just texting people like as really himself.

E (35:59)

It's really me.

C (36:01)

It's really me. Is it cool? All right. Yeah. Somebody said I think transactional related to a time sensitive thing. You've opted into great use case for tax. Yeah, that's a good point.

B (36:14)

Sound like Melissa was saying maybe like event related. That does make sense. People who are attending an event and like they're getting updates. That makes sense.

C (36:25)

Yeah, I agree. Dave cameo vids. Maybe you could send some of those unhinged Sora videos to people randomly.

E (36:34)

I think we're stepping outside of the inbox and even sometimes in the inbox like utilizing things like voice, text messages, videos like engaging past just like writing or typing is really useful.

C (36:46)

Yeah, yeah. Somebody said that their customers are event organizers so SMS is their number one channel but really just for re engagement. So I think that's where it could actually be really helpful if like we said like whether it's ever maybe a virtual event or a live event but if somebody's opted in and this is just like reminding them in another method outside of just email, maybe that actually would be helpful for someone as long as you're not emailing them anything else. That's really interesting because we have a lot of events and I think that could be like a cool like just way to notify people too if there's like a change in plans or like if you're finding like people are having difficulty getting to the site like sending them the Google like the maps address or something like you said Alyssa, that could be really helpful. Cool.

D (37:30)

So.

C (37:31)

Oh, that's a good one too. Reminders for SMS and email in tandem really helped in tune and tune. It helped people to tune in in attendance. So seems that that is working for folks. So when we're. If we are running a multi channel strategy and you've got SMS where you know it should be and, and, and maybe outbound email isn't your isn't like the winning channel and you're using other channels for outbound but email is assisting throughout the how are you or how are folks in the chat? How is everyone measuring the success of email? And I think this is also really challenging because it may not always be a first or last. Maybe you could see it was a closer but it may be also assisted throughout the journey. These customer journeys are never linear and they're never the same. So is anyone able to attribute how are folks attributing impact here.

B (38:21)

Such a good question. One of my clients, they, they sent a, an event follow up but they got a list of attendees from the event and they did a, they did a really nice job. Like I think we did a really good job of sending a follow up, a very small two email follow up sequence to this list. But the thing that they were most interested in was who was reading the email, who was reading the email and who was replying. So it's not that like the open rates and the click throughs didn't matter at all. But I almost think that like, certainly for some campaigns it's probably helpful to think in terms of like what, what is the, what really is the outcome that we want from this email? Maybe it's like, maybe it's just making sure like the right ICP is reading this and like engaging with it. Maybe it's like, maybe it's replies people are, they're actually saying, you know, they want to continue conversations that they had at the event. Something like that. But I almost think that like opens and clicks are good as long as you're filtering out bot activity. And as long as they're right, they're like kind of contributing to the, you know, to the overall like strategy of that campaign. They're like supportive metrics, not like the leading, the leading KPIs.

C (39:34)

That's a really good call out because every email plays a different. Has a different job. Right. So it's like just measure it, measure it fairly based on the job that you had it do. If it's there to be your closer, then measure it based on whether it drove a demo or a signup. But if it's there to offer value and helpful for nurture and content, then measure it that way. Yeah. Good call out.

B (40:02)

Yeah. Yeah.

C (40:03)

Gabulous. Any thoughts there on measurement?

E (40:06)

Yeah, I think Joe kind of hit on something of just saying like be really attuned to your attribution. It's like the big question, right, is like how do we attribute things? Really, really dig into the actual.

C (40:16)

It's never perfect.

E (40:18)

Yeah. Don't get caught up in vanity metrics. Figure out like your one or two top priorities and then work the story backwards that way. But I think looking into things, some things that people often forget to check into is like how many contacts has this person had before they convert? Really looking into like a bigger narrative.

B (40:35)

That's a good one also.

E (40:36)

Yeah, yeah, I think that one's been super helpful even Jess, We've started looking into that too. We, we wanted to dig into a little bit more some of our unsubscribe stories and narrative, and we started looking into what exactly was that? Like, how many emails exactly were they getting, when exactly were they getting them, and the information we were able to pull from that tool to so much more than just looking at kind of like the vanity metrics.

C (40:57)

Exactly. Yeah. Such a good call.

B (41:00)

Yeah. Because you're going to have those lurkers in the inbox, right? Like, they might not be. Yeah, they might not be, like, acting on every email, but if they are reading, if they are reading consistently and engaging consistently, that's still, like, that's still a signal that can be valuable.

E (41:15)

Very true, very true. There's a reason you use the, like, engagement statement of, like, 90 days. Right. Because not everyone's going to be engaged in 30 days, but they give them enough time to, like, actually engage when they need to engage and still read the subject lines and keep you top of mind. And as long as they're engaging sometime in those 90 days, that's a pretty healthy segment.

D (41:34)

Mm.

B (41:34)

Yeah.

C (41:35)

Yeah, Good call. Someone else said here too, like, they had a monthly. This, like, to your point, Joe, about lurkers, because I think, like, the majority are lurkers, Right. And that's like the dark part of this that we don't always notice until it's like you don't know what you had until it's gone. Because it's like they said they had a monthly customer email that was stopped at some point that probably really asked. Probably not good. Like, turn it off before he joined or. Yeah, before he joined and when he dug in, he saw consistent spikes in usage after that email would go out and then he talked to a customer and they were like, oh, yeah, I used to use that email as a reminder to go log in and schedule things and use the product. So sometimes also, someone told me, a marketer told me sometimes, like, just reminding people to do things is good marketing if it's. If it's really helpful and useful. But yeah, maybe also, like, incrementally test, like, did. Did things take a hit after you stopped something that you didn't think was effective? Like, there's other ways to. To look at that and talk to your customers and just hear from them directly.

B (42:37)

Oh, yeah, good luck.

C (42:41)

Was that sarcastic or was that real, Joe?

B (42:44)

No, that was real. I really like it. No, because, like. Yeah. No, the idea of.

E (42:50)

Yeah.

B (42:50)

Paying attention to what stops happening too, can still be the data.

C (42:54)

Yeah.

B (42:55)

Oh, yeah, I meant that that was 100% secure. Good stuff. Good stuff.

C (43:00)

Well, sometimes customers are hard to get in touch with, so like, oh, good luck with that. But no, I totally get what you're saying. Yeah, I know we're. We're coming up on 1:45 here. I don't know if there's like a 15 minute last Q& A kind of thing, but we'll. We'll just keep going until I get pinged from. From Allison. But so far I think we're okay. So any while we covered a lot of really good stuff on this call. I'm just like reading through the messages. Using emails to help the customer. Great emails. More persistent. Yes. People don't delete. True. What Joe gonna play us off with a free bird? I don't know if that means no.

B (43:38)

Not gonna do it. I can't do it.

C (43:42)

Well, that was like a big message that passed us up in school. I just want to make sure. Yeah, go ahead, Alyssa. I was gonna say there's a fun.

E (43:54)

AI things that we haven't talked about real fast if we want to throw them in there if we haven't.

C (43:57)

Yeah, let's. Any AI thing.

D (44:00)

Any.

E (44:00)

I know I was talking to the right lady.

C (44:05)

We. Some.

E (44:06)

Some things that I think to keep in consideration. I know we talked about like automating the email itself, but I think AI plays a really strong role both in the reporting and then like getting people onto the email list. That's still. I think it's like strongest use case is helping create really cool lead magnets. Just as like queen of that helping. You know, just as simple as like manychat helping. Kind of do customer support in that way and get people onto the list. Like don't forget about all the other ways that AI can help bolster email without being in the email itself.

B (44:35)

Sometimes I'll do it for testing messaging too. Like for cold campaigns in particular. I started creating like a mockup ICP in Claude and I will have. I'll like do research on the ICP have and then also on their like day. Day in the life and then test messaging on that icp. And so it's just helpful in terms of getting a sense of is this. Are there potential risks or like things that are just getting me dismissed that I might be missing can be really helpful.

C (45:11)

Yeah, I love that. One tool that I feel like I beat with a dead horse for something like this too is NoteBookLM. If you have a lot of that input data already about your ICP, putting that into NotebookLM is awesome to kind of pull insights and content and email and copy from that could be a good one too if you've got a lot of that personal data to send to get ideas to send some sort of a non marketing type of message, but something that hits to like their personal interests. You guys can keep talking. I'm just reading through the, the chats. How do you promote your newsletter? Homepage slide out, blog page, pop up, subtle footer form, what's best and non intrusive.

D (45:54)

Can I ask a quick question to Alyssa and Joe and maybe anyone else who's on the call. So one of my, one of my, one of my co workers was at this, they were like March of world form in San Francisco a month ago or two months ago and they mentioned this like presentation on marketing that was great. On email marketing that was like now with AI, email marketing is moving from this moment where like it used to be this kind of like timeline where it was like you know, user creates account like check for product behavior, send triggered email, check for product behavior centric email. Where now like ideally we'll move to this world where like you create an LLM or whatever, you create a model where like you fed it like all the key moments for your product or whatever it is that you need, that your client needs you to take, your client wants to be taking. And like that model can like just spit out in a timely manner like the action they need in a complex, like a complex thing where it's like there's like 10 product actions or 10 actions on them to take and they've done 1, 7 and 9, like what the next best thing is. But like apart from like I know we still need to sit on with like our data team and our marketing office to be like how the heck could we build something like this? But I'm like, I have a hard time conceiving like how you would, how do you, how does one build something like this? Like, do you have any ideas?

E (47:00)

I don't know about building it in house, but I do know that there are quite a few basically extensions that would be added onto your inbox provider. I've tested out a few of them mainly in the DT space. I don't know of any that are really working proficiently for B2B yet just because it's a different kind of messaging usually. But it is really cool to see where it's going and I do think that that will become a little bit more readily available. I'm going to think on that and I'll send out, I'll Maybe post on LinkedIn too if I think of anything helpful. But I'll get back to you on how you could start building that out in B2B, because I know that it's happening in the D2D space.

B (47:29)

Yeah, I'll give it some thought. To Gabby, that's a really good question. Yeah. But I don't have a good answer for you right now. Sorry.

D (47:38)

Only for your LinkedIn post.

B (47:40)

Yeah.

E (47:42)

It feels like one of those things we're on the cusp of and it's like you can feel so excited. It's how I imagine people felt about saying we were going to space. Right. It's like I can see that it's going to happen, but are we there yet?

D (47:52)

I don't know.

B (47:53)

Yeah, because there was like so much. The big thing that keeps coming up for a lot of clients I've been talking to more recently is data. Like the list data. Where is it coming from? Where is it living? What tools is it interacting with? Like, how do you get data from Salesforce and Gong and HubSpot kind of to be working together and talking together, updating regularly. Like, I think there's a lot of. There's definitely a lot of opportunity there. But yeah, I think it would. I have to think on it because it's. It's complicated.

E (48:26)

And adding to that point too, I think the problem that people are running into is it running away with data it's not supposed to have and freaking out subscribers. Those information about themselves is now being.

C (48:38)

Repeated back to them.

E (48:39)

It's like, whoa, whoa, whoa, whoa.

B (48:42)

That's the.

E (48:43)

Yeah, I think that's one of the quirks kind of being wrestled with right now for sure.

C (48:48)

I have some good questions in the Q and A, I think kind of related, but what's the best practice for number of in app guides during the first 30, 60 days and et cetera and new benefits with features like best practice for the number, I guess, of in app things that happen in the first 30 to 60 days as someone gets into a product.

D (49:11)

We've definitely been burned on this. We had something happened where our. I mean, right now our onboarding team on the product side has like a lot of like in product in apps. They're not even in apps that we're sending natively with our platform. They're like the engineering team built them. So I think you need to be really like. I mean, Sam, I'm not sure what. What you're. What the UA you're building off of is like, but whether it's a website or whatever, like, you should try and you know, you want to be aware of like, what already are the like things that are calling for attention on the screen when you're putting it in apps and. Very true, like trying to work closely with your team to make sure that like we definitely have issues sometimes where like multiple teams are like sending out in apps about different things that really seem to pertain to different life like cycles. So I think it's always the really difficult struggle of like we want to be respectful but like I need to make sure that my voice is heard amidst all the other teams or all the other people that are like sending in apps in the same moment. So just trying to be respectful and working closely with your team and like, like Joe mentioned, like segmenting really strongly, like only show this in app for those people who like clicked into that page and like showed interest in.

C (50:09)

Exactly. It's like driven mainly by behavior triggers first and foremost. So then you feel like confident that this is a need. And then I know when I worked in a plg Org that we were very careful about the messages we sent in app and very intentional to not flood it too much because then they could start to get ignored. So it was like maybe major feature updates if they weren't behaviorally triggered. But like I think if they're just really helpful, like the person hasn't done the next thing from that step, you know, in a certain amount of days, can you send them like a guide or some direction on where to go? Because, you know, being on the user side of it, it's definitely helpful to have those come up. Sometimes when you're like trying to navigate through and learn, but like sounds like there's like no perfect answer. But I think it's good to just be in intentional.

B (51:06)

Yeah. And almost like just from a kind of more, maybe more of a messaging side like, but also the, you know, the kind of their own user journey side. What is the. What are those micro yeses or those micro wins that get them closer to that job to be done? And how do you help them hit those many like milestones, those many like micro achievements that I think actually like a lot of trying to think of a specific example. I think Zapier is pretty good at this. When you first sign up for like, you know, Zapier, they are pretty good about helping you just send your first zap and then send your like plug in your first, you know, integration. And those little steps get you one of the things like the more I use tech, the more I realize like it is hard to get people to Use tech like it does take a lot of encouraging and education. Like we. It's so easy to assume that your users, they almost know more about the platform that they. Than they do. Which depending on how they heard about it, whether it's from a team member or like someone else bought the platform and then they joined later and they're like, oh, we've got to learn this new tool now. Like, there's a.

C (52:22)

It's so true.

B (52:24)

There's a lot that goes into that, that buy that user's context and what those. How you get it to plug into their workflow, how you show it. How you show it plugs into their workflow obviously and as easily as possible. And then how do you help them start like using it daily? Like, I don't know. This is just stuff I've been thinking about a lot. Not like I have a really good answer for it, but. Well, what does that journey look like? You know, like, how can like you and your like product team kind of map that out? How can you help people get closer to. Yeah, actually using it, seeing wins with it.

C (53:02)

Like if they only knew what it could do. Yeah. I think the use cases too are really helpful because it's like if you only knew what you could do. You're using this at like this layer, but it's hard to know what you don't know. So I think that's where the use cases are so critical to share to see that this is exactly how it can be done versus just a feature explainer of like, here's this feature we have. It's like here's how seven different customers are using this feature that starts to give them ideas for how they could use it themselves. I think that that's the, that's the big key for that.

B (53:37)

So good.

C (53:38)

This is a good one too. They want us to riff on what LLMs we're using for what connected to email and SMS and app. I guess just like the entire flow. I have a few in my mind, but I feel like. Gabby, you mentioned some good ones too, like Nadan and is it Naten or is it Nan? We don't have to discuss this here, but I don't know. I said Nate, I said Nate and I felt like it was. Yeah, how are you used? Like, are you using Claude Sonnet? Are you using ChatGPT? Like, what are you using?

D (54:11)

For what I can start, I sometimes use Claude for the customer McP server because ChatGPT is like really lagging with McP servers. But ChatGPT, like one of My teammates has developed a really good ChatGPT voice brand guide for us that is really easy to use. And also it's so much. I think that's what you start building and then you're like, oh no, I put all the knowledge in clotter here, so I better keep using that.

C (54:34)

So true.

D (54:34)

I've been trying to train a ChatGPT thing to help me with analyzing my. The revenue metrics tracked like email engagement. So I feel like I've invested a lot there. But I think so many of them are very similar to each other right now.

C (54:46)

Yeah, yeah. And then you get comfortable in one. I just, I gotta add one to the list. If there's. Just go check out NotebookLM. It's like ChatGPT and Google Drive had a baby. So it works just like ChatGPT, but only from your sources. I don't know if that was the best analogy. But only from your sources. And you can upload like 300 sources into it and it's like. And then you chat it. So it's. So it just doesn't hallucinate. It removes like that piece of it, which can be kind of frustrating sometimes. Do like, don't have 100% trust, but it can create like mind maps of it with like the click of a button. Podcasts, like, I think a lot of product marketers use it. A lot of marketers use it for a bunch of different use cases, but that would be a top one on my list.

B (55:30)

That's good to know because I've been using Claude mostly more recently.

C (55:35)

Like Claude projects.

B (55:37)

Yeah, Cloud projects. And they like, it still hallucinates quite a bit. Like, even when I tell it explicitly, like, hey, refer to this document. It'll make stuff up. Like, where'd you get it? It's like, oh, I'm sorry, I totally made that up. Like, so yeah, I have to try.

C (55:52)

Yes, yes, yes, yes. Yeah.

B (55:54)

If you've noticed, it doesn't hallucinate as.

C (55:55)

Much at all because it's. It's literally. It's not what, it's not doing any data scraping. It's just. So if you have a lot of sources, like input sources, like I even know like sal reps that are using it to build RFPs because like they have all of like their decks and their videos, all of like their customer. Like, so you could put three, like you could make a debt a database from it essentially. So it's like there's so many ways that you can use it, but it's only pulling from the source.

D (56:19)

You give It So if you don't.

C (56:20)

Give it the source, it won't have that information from you. But over time, what's really nice too is it syncs with Google. So if you're like adding stuff to a document about your icp, you just sync it and it's in your notebook. I'm telling you this. Everyone, long list.

E (56:34)

This one.

C (56:35)

It's been like a game changer.

B (56:37)

Yeah. Oh, that's good.

C (56:38)

Yep, That's a good one. I know we're at three minutes left, so let me see this Q and A.

B (56:43)

Can I quickly throw something on the.

C (56:46)

Yeah, I was gonna say go ahead.

B (56:49)

One more quick thing on riffing on LLM. So I use cloud projects and I let like, one of the things I love doing is having I have an email messaging brief which goes pretty deep into important parts of building your messaging for your emails, like the audience. But also things like unique mechanism. What's the unique mechanism of your particular product or particular webinar? Like getting into the differentiators and the value props of that, what you're offering. Stuff like that. So I have a brief. I give Claude a bunch of context and data around that particular audience, that client, whatever, and then I basically have fill out the brief for me and it helps me structure some really good email promo campaigns for like webinars, stuff like that.

C (57:37)

Love that. All right, well, for. There's a. Yeah, that's a great call out. I wrote that down, Joe. To fill out the brief. Folks, please rate today's session as highly as possible. I'm kidding. Would be great to see everyone's feedback here. We really take it seriously. And just please vote the other one. The other question was, can you recommend resources for finding a freelance fractional marketer who has strong familiarity with customer IO segments and campaigns? Or like somewhere to find them or just go straight to the source.

D (58:15)

I think I replied to Joshua, but. You did.

C (58:18)

Oh, that was you. Okay.

D (58:20)

I know some freelancers I can be in touch with. Who, like we're trusting her in the past.

C (58:23)

Perfect. Yeah, perfect. Okay, great. Awesome. 10 seconds left. We're really going down to the wire on this one. Protecting your reputation with engagement. That might be too long to answer. All right, any last folks? I think that sounds like. Oh, that was so good. Can you say more about ideas for how to balance protecting your reputation for HubSpot or whatever your domain is, Prioritizing engaged contacts while continuing to send to lurkers?

B (58:55)

I feel like Alyssa and Gabby could have some really good thoughts on this. I'll just say Quickly. I think having a plan for it's good. I think it's good to re engage people or try to re engage people. So keep so monitoring those like 30 day, 60 day plus engagement cohorts and inviting them to sign up for your newsletter. Like don't just opt them in, invite them to sign up for the newsletter or like whatever it is you want them that that thing you want them to do, do that. Send those emails. If you're sending promotions, people click on something but they don't actually go through with it. Send retargeting emails. Like when my clients did that and saw a lot of success from those like retargeted emails. But also having fun for phasing those inactives out too. If people are really not like if you have tried re engaging them, they're just not engaging. I think it's called like a sunset policy or something. Or something. But have that, have that policy in place.

C (59:48)

Have a plan for Facebook sunset flow.

B (59:50)

Sunset flow. Because it doesn't make sense to keep emailing people who are not engaging. Probably do a few like renurture touches but like phase them out otherwise because that pulls drag on your deliverability and stuff.

C (60:04)

Yeah, for sure. All great points guys. This was super helpful. I learned a ton of thank you. I know we're over time, but I just wanted to get to as many questions as I could. But thank you. Thank you to the guests, Alyssa, Joe, Gabby, thank you Customer IO, our sponsors, the awesome people engaging in the chat. This was really fun. So thanks everyone. The recording will be sent afterwards and we'll see you on the next one.

E (60:29)

So fun. Thanks.

B (60:30)

Sounds good. Thank you so much. Thanks Jenna.

C (60:33)

Have a good one.

B (60:34)

Thank you too.

C (60:35)

Bye.

A (60:39)

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