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I have some really exciting news. We just released our second annual AI Marketing Industry Report and it's free. You'll be surprised by how often marketers are using AI and the tools that they're using. This is a comprehensive study of more than 730 marketers, and it covers how marketers are applying AI to their work, the benefits of AI, the big concerns marketers have, and a whole lot more. Even though I'm the author of this research study, I can say with full confidence that this is the most comprehensive study of AI adoption among marketers that I have ever seen. Get your free copy now by visiting social mediaexaminer.com aireport25 this might be just what you need to get your boss or your clients moving along with those AI initiatives you want to start. Get it now@social mediaexaminer.com airport25 hey, it's Michael Stelzner here. After running Social Media marketing world for 12 years, I've noticed something fascinating about the marketers who attend. They usually fall into two camps. Camp number one is those who show up because they have to. Their results are declining. They're scrambling to catch up. And camp number two is those who show up because they want to. They're already achieving a level of success, but they know that change is coming and they want to go so much further. Both learn valuable insights, but their outcomes are completely different. As Emily Ray Shutti said, I came away with a million ideas and new creative ways to approach my work. My business has since doubled in size and revenue. The AI revolution is here. Instagram algorithms keep shifting, Facebook's ad costs keep rising, and the list goes on and on and on. What type of marketer will you be in 2026? Join thousands of marketers at Social Media Marketing World 2026 this April in Anaheim, California. Save big when you register today at Social MediaMarketingWorld.info welcome to the Social Media Marketing Podcast, helping you navigate the social media jungle. And now, here is your host, Michael Stelzner. Hello, hello, hello. Thank you so much for joining me for the Social Media Marketing podcast brought to you by Social Media Marketing examiner. I'm your host, Michael Stelzer, and this is the podcast for marketers and business owners who want more exposure, more leads, and more sales. You're probably focused on social media, obviously, because that's what this podcast is all about. But what about email? And what about email marketing automation? If you know there's so much more that you could be doing to get in front of prospects and customers via email automation, Then today's guest is going to unlock a lot of opportunities for you. Her name is Jessica Best and we're going to explore email automation that actually moves people to take the desired actions you want them to take. By the way, if you're new to the show, be sure to follow us on whatever platform you're listening on. Let's now transition over to this week's interview with Jessica Best, helping you to simplify your social safari. Here is this week week's expert guide. Today, I am very excited to be joined by Jessica Best. If you don't know who Jessica is, she is an email marketing strategist who helps marketers mine their customer data to deliver better results for their company or clients. She's the founder of Better Ave and has worked with businesses such as Applebee's, Winnebago, Planet Fitness and more to drive revenue using customer data. Jessica, welcome to the show.
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Hi. Thank you for having me. I'm excited to be here.
A
I'm super excited that you're here. Today, Jessica and I will explore email automation strategies that move people into action. Now, before we get into that, I would love to hear a little bit of your story. How in the world did you get into email marketing?
B
Do you know? A lot of people actually ask me, like, how did you get into email marketing? Like, how has that occurred to you as a job? It didn't. I didn't go to school for this spoiler alert. But I did get a background in journalism and it's surprising to me how much of that I actually use in my current career. No, I fell into email marketing, like all the good ones. It became part of my job. I was a content marketer and it became part of my job to send out the newsletter, kind of get into automation. And I actually got scooped up by the email platform we were using to be their marketer. So, like, I was, I kind of taught myself email marketing and they were like, oh, you're reasonably good at this and you have a lot of enthusiasm for our email platform. So would you, would you consider coming on board to be our email marketer for email marketing? So I definitely went full meta. I went into the deep end of email marketing about 15 years ago and I've fallen completely in love with it. I think over the course of my career, I've gotten a chance to be kind of an educator, teacher, type about email marketing because nobody really got an education in email marketing. And I got a chance to work on some pretty big brands. I love that you call out Some of my favorite clients that I've had over the years when I went to a larger agency. So I spent about eight years, seven years actually, at Barkley here in Kansas City. And it took me from, you know, kind of a one woman show to a 17 person team and getting to not just teach my clients how to do email marketing, but really grow a team of strategists and executioners. And that was a really fun time. So about three years ago, I actually took the leap and went out on my own. You mentioned my company name, Better Ave. My last name is Best and I didn't want to call myself Best Email Marketing. So little play on my name, Better Ave or Better Avenue. And I've been out on my own for about three years, still doing a fair amount of speaking, but really helping clients of a variety of sizes learn the stuff that I can do really well that I learned on some of the really big brands. Now I get to help maybe more regional or growth mode brands bring email marketing to part of their strategy.
A
Love it. We are huge advocates of email marketing over here at Social Media examiner, but not everyone who is listening to the social media marketing podcast has really fully embraced the email marketing side of things. So what do you want to say to marketers who maybe are not taking full advantage of email automation? What, what are they missing or said another way? When this is done really well, what is the upside for marketers?
B
Yeah, so I'm going to answer two questions because the first one is, I promise you that no matter how much you love social media, email marketing can be your very best buddy. So I actually became really good friends with both the paid media and organic media side social media sides of my agency because email is kind of a different bag, right? Like this is an owned database of people that literally gave you permission to put ideas in their inbox. You guys know the power of it. I mean, you know the power of it, Michael. So I think just maybe if you're not sure about email marketing and you listen to this podcast to see if you might have interest, I will tell you my two favorite letters. Roi. Email marketing makes money. We have permission to send and we do, and then people read it and they take the actions that we want. So we're a channel that really prides ourselves on attributable action and that's what we hope to maybe optimize today together. Today, specifically, email marketing automation. So I know one of the big gaps in the marketplace when I talk to marketers is I'm doing emails and they mean they're doing like a monthly newsletter, which is a good start, or they're doing when they have time, ish newsletters. So I think just really dialing in on where do you make your effort back, where do you make your money back in email marketing. And that's in automation. So when done really well, email marketing automation not only saves you time and sanity, it also puts something in somebody's inbox at the exact right moment for them. And there's almost nothing more powerful than that. So getting into email marketing and doing, you know, permission based content is a great start. But we're gonna, we're gonna challenge the folks that are listening today to level up because I want to see that automated perfect timing with perfect content at the perfect cadence for each recipient on our list.
A
So why don't we just define email marketing automation for those that are already doing what I'm gonna call email broadcasts, you know, which probably is what a lot of us do. We schedule an email and we send it out, just kind of like unravel a little bit about defining and then we can get into some of how.
B
To use it perfect. So I love broadcast as a, as a counter term, right? Broadcast means it's sent on my schedule, the marketer schedule. And then automation is that it's really almost that one to one send at the moment that means something to the recipient. And the best example, the most basic example of this is a welcome email. Somebody signs up for your email list, they should get a email so it's triggered by an action or by inaction. Some of my favorite automation is actually how do we wake folks up if they haven't taken the next step. So automation is meant to mostly be in very small quantities. You might send one at a time, but over the course of every minute of the day so that that recipient gets it when it is probably most relevant to them. Whether that's they just purchased something or they didn't purchase something and we want them to.
A
And I'm glad you added that distinction because now all of a sudden you perked the ears of a lot of marketers are like, oh, interesting. So what I'm hearing you say, Jess, is that I can create some really good, well, refined emails that are designed to trigger, for lack of better words, when certain things occur or a certain amount of time occurs and things do not occur. And that opens up a lot of cool stuff in the eyes of marketers. Because this is almost like a set and forget kind of thing, right? Because with organic marketing, it's not set and forget it's like new every morning. That's a huge advantage, right?
B
Yeah. I'm staring at a white piece of paper again. Oh my God. No. You know, that's a really good call out because I say automation saves our sanity. What I mean is I don't want to have to send the birthday emails every day. I mean, there's no way a human being has time for that. We aren't going to let the machines do the heavy lifting for us. So I love that additional benefit or that additional distinction of it doesn't have to be entirely set it and forget it, but once it's on, it kind of makes you money till you turn it off. Now my plea will be that you take a look at the things that are automatically going out on behalf of your brand. Maybe once a year, if you're really doing a lot of automation, try and do a batch of them once a quarter.
A
Love it. Okay, so we're going to spend some time today going through a bunch of different automations that there's a really good chance that some marketers are doing. But there's a really good chance most marketers are not going to be doing all the things that we're talking about today. And even if you do some of the things that we're about to talk about today, there's a good chance you could be doing them better. So let's start with wherever you want to start. When it comes to email automation, where do you want to begin?
B
Well, we have to begin at the beginning, right? So the one you already heard me say is the one that I hope everyone listening is at least doing something for their welcome email. And this is kind of in two categories, right? When somebody signs up or subscribes for your newsletter, they should get a welcome email. Welcome to the newsletter. Here's some of our best stuff, some of our subscribers favorites, and here's what we want you to do next. Right. Don't forget, this is email marketing. Is there something else that would deepen their relationship with us? And I would say even better than one email would be to send a series of emails where the first one is sent immediately and then sort of the next email is, you know, since you're interested in our newsletter, you might also check out our social channels or you might love this 5 star review from one of our readers. Is there anyone else that you think should be subscribed? Right. What is the next thing? People will never be more engaged with your brand than the second after they just signed up to receive your emails. That was a pretty big step they took. So just taking advantage of that and really trying to deepen the relationship at the right moment. But I will say there's another sort of immediate trigger that I think especially our B2B listeners are probably already using and wouldn't think of as a quote unquote welcome email. And that's a lead nurture email. So lead nurture is the first thing you send when somebody fills out a form. It just doesn't have anything to do with your newsletter or your newsletter content. It's probably more on the side of sales automation or following up with that person.
A
Love it. Okay. And I definitely want to get into lead nurturing, but I do want to really dig in deep if you're cool with it, in this welcome email because I feel like there's so much wisdom you have to share here. So, so far, here's what we've heard. The best time to send an email and the easiest thing is the moment they sign up for your newsletter or whatever your free offer is. And that even in your case could be like a PDF or something like that, right?
B
Oh, yeah.
A
But the, the part that I thought was really interesting is I want to kind of break down like the. Your professional tips on what to put in the first message. And then I want to actually explore some of these second messages. Because you said, well, there's two obvious second messages. The first one was like, hey, check out our socials. Another one was like, hey, here' a review from one of our other customers. Maybe you want to add your name to the review or give us a review or maybe you want to share that with the colleague or a friend. But what I want to do is start with that very first message because obviously if they, if you get that message, like, right, then it might set in motion a series of things. So, like, what should we include? Because I bet you most people just are like, thank you for signing up and that's it. And they're done, right?
B
No ask. That's exactly right. So many people are like, I did it. I set an oh, welcome email up. Like you've set it up in your email platform because it's turned on by default and so you customized it with the sign off from your president or something. So I want to answer that in three ways. And I know this is cheating, but you did give me the platform. So the first One is for B2B marketers. I think even signing up for a newsletter, you want to really start to show your brand, your voice. So you and I Are both friends with Rich Brooks and his agents have changed. Podcast does this so well. If you sign up for his podcast newsletter, he immediately starts talking in his own voice and sharing some of his own stories. Stories, you know who they're going to be. You've, like, almost validated why they signed up for you, which that's what a welcome email does, right? So one piece of that is setting the tone and kind of giving them a pat on the back. They're going to feel really good about signing up because they're already starting to relate to you. The second thing I would say is just newsletters, whether it's B2B or B2C or whatever in general is. We kind of just said it. I think the next ask needs to be in there. Do I want them to download something now? Do I want them to follow me in social? Do I want them to reach out to somebody? Do I want them to start shopping? So this is where that third piece comes in. If you are direct to consumer, if you are literally an E commerce brand, that first welcome email, forgive me, should sell something. That's probably why they got on the list to begin with. And while I'm not a huge believer in every welcome email needing an offer, it is pretty prevalent for e commerce. And at the very least, they probably signed up because they're shopping for your brand. So final word for me is e commerce folks. It's time to put products in front of them. They've said yes to the first date. We gotta ask them out again.
A
Okay, I love this and I want to dig a little deeper on some of this stuff. So first of all, your voice, for those that don't know Rich Brooks, he's very funny. He's a great communicator and has a unique style in the way that he communicates. But every business has a style of how they communicate, right? Some are very friendly, some are very formal. It's just kind of like whatever that style is. What I'm hearing you say is like, make sure that that voice translates into that message. Because if you just use the standard templates that are built in with these email platforms, it's going to be super generic, right? Because like, this is the first time they're showing up in the inbox. You want to make sure that that matches completely. And then you also said, sell them something. And I wanted to ask. I like that. But should we also set expectations in the email as well? If we know we're going to be sending them a series of emails, should we say, hey, thank you so much for signing up. Just so you know, here's what you can expect from us. Is that worthy of putting in there as well?
B
So, yes, and I want that on the signup form. I want that to be before they ever hit subscribe because there have been some mismatches. I literally had a guy walk up to me at a conference a couple years ago and he was like, hey, so, gosh, I am really struggling with my inbox placement. I can't figure it out. My emails are so good. And I was like, yeah, you're, you know, some of the things you're saying, everything sounds okay. How often do you send email? And he's like, oh, it's a daily newsletter. And I, I was like, are you the New York Times? Like, what did. Did you tell people it was a daily newsletter? And when I went to look at his signup form, he didn't set that expectation. And so he was getting a gargantuan unsubscribe rate from subscribers in their first seven days because they were just overwhelmed. So I would say set those expectations on what you're going to receive from us and how often. Right on the signup form. And then the welcome email can maybe back that up a little bit. But I think we're setting the tone for that more with, you know, marketing Profs, of course, does a great job of onboarding as well. Where at the bot literally says this is warmup email, one of three.
A
Okay.
B
Like, you already know you're going to get free emails.
A
Yeah. So. Okay, perfect. So tell us a little bit about, like, the variety of options, the cacophony, the menu of options of things we could do just to give people, like you've already mentioned a couple, but let's, let's just like expand a little bit just so people can open their eyes a little bit to what's possible on the second and third message. Maybe.
B
Yeah, so the second and third message. We have a couple of ways we can go. We can also deepen sort of the ask for. I'm going to go with Winnebago really quickly. I know we're going to come back to that example, but we're kind of delivering on what we said we were going to send them. And then we immediately start suggesting either other content or other products that they might like. And for Winnebago, that's not like, buy now. It's a $400,000 vehicle. Nobody's clicking to buy now. It's more like, I can see that you're considering this, can I help you by supporting that with more about that product or customer reviews of that product or just customer reviews? I mean, I think Voice of Customer is a interesting thing in a welcome series because it kind of again, validates like, oh, it's not. There's a little social proof to that, right? It's not just me. I'm very smart because I also see here that Michael gives this company five stars. So there's that continuing down the funnel of sort of validating the relationship that you're creating with the brand. I do think, like I said, an ask is appropriate. So whatever that is for your brand and I will be a little bit maybe textbook ish here and say that what that is is going to depend on your customer journey. So. So, you know, it's not just email marketing. Think back to what your actual customer is experiencing or prospect is experiencing. What is the right next step? For some companies it's here's more free education. That's the most we think we can ask for. For some companies it's, you know, buy this product right now and then everything in between. And I would consider follow us in social media to be the in between. It's still a pretty significant ask. But what I found is that showing people samples of what you post in social is so much more effective than just saying follow us in social hears.
A
The icon and if you have like an incredible YouTube channel or something, you know, and show a little thumbnail and with or a picture of like you got a big subscriber base there, they might find that really interesting. How often on this welcome email sequence that we're really talking about, if we're going to send however many we're going to send, is there any kind of general rule of thumb of like send the first one on day one, the second one on week two, or what's your general feedback on that?
B
So the first one has to go out immediately. That's the only hard and fast rule. Like the thing automation, email marketing automation can do better than almost any other marketing channel is it can beat human beings to the punch. So the first one should go out immediately. That's the expectation of the person who subscribed. And I think it's just our best chance to get in front of somebody while they're still warm. The second and third I would typically start with. Well, I would start with one. So if you don't have any, start with one. But if you have one, I would suggest trying to expand that to three. That's one of my favorite sort of bundles of email marketing. And it's because we're trying not to overwhelm the person. We're going to send them a newsletter at some point in this month, so we're just trying to kind of warm them up. And again, as just a template, I would say that starts in the first week. So if you send one immediately, wait a couple of days, send maybe a plus up. Hey, did you think about this or have you seen this? And then I like to send on day eight, which is usually the same day of the week as that first immediate email. If they subscribed on Tuesday morning, heck, maybe Tuesday mornings are their free time. So I like to match that day of week for the third email just to come back around and put something else in front of them that they might also like to read.
A
Okay. I love it. So we have talked so far about welcome emails, which typically are for newsletters or like free offers. But what about. You kind of mentioned lead forms a little bit. And there's all sorts of different kinds of lead forms. There's the kind where you just have a free PDF and then there's the kind where you have to fill out a, a, a form to get a demo or to actually talk to a person. Like, there's all these different kinds of forms. And I, I'm assuming when we say lead form, we're, we're talking about like actual prospect who's interested in buying something. So talk to me a little bit about that whole process because, like, a lot of people just send one email off to a salesperson that says, here's your lead, and they move on. So there's probably a lot of opportunity here, right?
B
There's so much opportunity here. And I think this is actually, I, I love that you bring up the sales, like shoot the email off to the salesperson and it's in their court. It is. But remember I said automation beats humans to the punch every time. So I want to figure out as a marketer, how I can best support my sales team by either supporting or even automating what they would send. Already what I can't automate is picking up the phone and calling the person. So, like, if you get a request for a demo and they put a phone number in, please call them. Like, I can't beat that. Right? As an email marketing person, I cannot substitute you picking up the phone and calling them. But what I can do is if you, Michael, are my assigned sales rep when I submit that lead form because it's based on the product that you own or the geography that you're assigned to. I, the marketer, can actually send an email as if I'm Michael. That beats that call to the punch. Right. I can literally get that out the door before a human being even has time to dial the number. And the truth is, while I would love to say that all of our sales teams are calling within five minutes because they know the effectiveness of that, the truth is it might be in the first few hours or maybe even a day. And so this is one of those. I get it, you're listening, you're ready for me. I'm going to give you a call. So kind of prepping that prospect for. I'd love to set time to call. I'm going to give you a call in the next couple of hours. If there's a time that works better for you, hit reply and we'll take care of you. That type of thing. So you're right that there are two kind of categories of lead nurture. I want to go back to that really quickly, because if somebody has downloaded a free piece of content and they were sort of of, let's not say begrudgingly, but they kind of gave you their contact information because it was a worthy trade.
A
Yeah. That's the purchase they made, Right? They gave you their information for that thing, right?
B
Exactly. Exactly. But that doesn't. It's not the same thing as I'm requesting a demo. Right. The trade of information needs to be treated a little bit more gently, almost like that welcome email. There are some other pieces of information I can send to you, and then I like to sprinkle in. Maybe the brand sends me. I have a great HR client in Kansas City that does this really well. When you download something, she keeps track of what topic that was on and then sends a nurture stream about more things on that topic while the salesperson is also calling and following up. So there's this beautiful sort of dance between what she's sending and Beth and what the salesperson Derek is actually like, sending. And I was like, so do you know, does Derek know that we can automate that for him too? Like one from Beth from the brand, and then wait a day, one from Derek the salesperson, and then one from the brand. So just setting that dance up can be a little bit lighter or gentler for somebody who didn't say, I'm ready for a demo. Give me a demo right now. But if they requested a demo, kids, you're gonna. I'm gonna be so, like, on repeat, this whole podcast. This is Marketing, we should do some marketing. So if somebody requests a demo, what we really want to do is start, start trying to get that schedule. So we're really doing almost sales automation to try and get that person either to pick up the phone the next time we dial or to reply back and let us know when we can set some time.
A
Have you ever attended a conference and came back with all sorts of ideas and you were fired up but you struggled to get everyone else on your team to be on the same page? Well, here's what I noticed after a dozen years of social media marketing world. When one person attends, they get great ideas. But when a team attends together, they create something much bigger. Think about it. One person learns about AI and marketing. A team builds out an AI strategy, one person discovers Instagram tactics, A team redesigns their entire content approach. Noah Stanley told us, quote, I will bring multiple members of my staff next year. The mindset, openness and amount of time the experts gave to us was head and shoulders above other conferences unquestioned. Quote, when your team attends together, you can cross pollinate ideas in real time, divide and conquer to cover more ground and return with a unified action plan, not just a bunch of scattered notes that you never get around to. Plus you've got a built in support system when you try new strategies and you're back at the office. The company seeing the biggest results from social media marketing world, they're the ones investing in team transformation. Bring your team to Anaheim this April and multiply your impact. Learn more at socialmediamarketingworld.info you mentioned Winnebago earlier and I know this is the area where you have an example, so why don't you share with us a little bit about what you did for them so people can understand some of the possibilities here.
B
Yeah, well, and I love the results of that one. So if you're looking for why you're listening to this podcast, a 50x ROI is a pretty good reason. So they had a brochure on their website for each of their models. Again, Winnebago, big expensive purchase. There's a, a lot of detail on the website, including literally a downloadable brochure, technical specifications, all the model variations, and they basically just said here, do you want it? Click and there was a form that said do you want to give us your email address? And I was like, oh great lead capture. And then they didn't do anything with it. And I was like, I'm about to blow your mind. What if we sent the brochure that they just downloaded to their inbox. If they give us their email address and permission to use it. Like, like we have to make sure that they want to receive emails. But since it's not a required field, if they give us an email address and say I'd like to get this in my inbox, I think we should send it to them. What do you think? So not only that, first again, immediate email saying here's the brochure you were looking for. But then that Nurture series was actually over about two weeks. Winnebago is a long term decision. So we actually the next email was here's kind of a deep dive into the specifications of the model that you were looking at at. The third one is behind the scenes or influencer videos of kind of the tour of the vehicle, either how it was made or how it's laid out. And we start to add in a, you know, if you're shopping for this model, you might also be interested in this model in case this isn't quite the fit for you. So starting to suggest you may also like. And then the fourth email was really just driving the Winnebago brand home. So we talked about this a little bit with Rich. It's so important that if Winnebago has direct access to someone while they're shopping for an rv that they take that opportunity to really convince that person that there's no other brand like Winnebago. Because Winnebago doesn't sell direct to the consumer, they have to sell through a dealer. And that dealer might have an incentive from a competitive brand that's better. And they'd rather move that person that comes in for a test drive to another brand. We have an opportunity to convince them them no other brand will do. It has to be Winnebago. So that four part email series, we set this up for one of the vehicles just to like, let's see if it works guys. We set this up for one of the vehicles and it made an immediate lift year over year in sales. Not just like we saw clicks or like, like we literally could see the jump in sales for that model. And we matched back buyers, the warranty, registration, email address to the people that were on the nurture structure. And once we'd finished drinking champagne, we rolled it out for the rest of the models. We did a total of nine different Nurture series, nine different models. And in I think it was the end of the year 2022, we figured out that of those people who were nurtured to buy that went on to Buy that model within 30 days, we could calculate a 50 to 1 ROI.
A
I love it. I want to ask you a couple questions here because I've got a couple of thoughts on my mind.
B
Yes.
A
When you are asking for an email address in order to get some sort of PDF, in this case maybe a Winnebago detailed PDF, after they submit the form, are you instantly letting them download it or do you wait for them to get the email so that you can validate that it's a legit email? Because this is one of those things that I've always wondered about 100%.
B
This is maybe one of the top three questions I get from a B2B audience. Especially, do we gate our content or do we just ask people for their email address and give away the content anyway? Right. And I think the answer is maybe shifted a little bit over the years. I definitely know some brands that still say, give us a correct email address and we'll just send it to your email address. If you didn't give us a real email address, go back and fill out the form again. But I think we've kind of moved away from that a little bit and partially. You can kind of see the example with Winnebago. It maybe doesn't make sense to gate that. Like, if you're shopping for a Winnebago and you want all of the specifications of a $400,000 vehicle, I don't think we should gate that. I don't think we should say, you have to give this to us to get it delivered to your inbox. So I think it depends on the content.
A
Ah, so in this case, you offer the option to have it delivered to their inbox or download it. Okay, that's interesting.
B
Exactly. So when they submitted their email, we did just say, and here you go, it's going to download in a new window. But we did take that opportunity to send it to inbox so that it's for safekeeping later on. But I would say if you have something on the flip side that's more like primary research, let's say you spent three months doing primary research on the topic that everyone quotes, but nobody has numbers for. You can gate that that is wildly valuable and it's fair to say no, no, we'll send that to your inbox for you. You're going to have to give us a valid work email address. Now, I will say the asterisk there is. I don't automatically opt people in in. You do have to tell me who you are because we're a sales driven organization. But you don't have to opt in for marketing automation. You don't have to opt in for our newsletter. Someone's going to call you, because that's the deal. Right. But we aren't going to automatically shove you into every nurture stream that we've got. You have to kind of still give me a checkbox with permission. And also I would love to know when you come out with next year's research. Sign me up for your email list.
A
Got it. Okay, cool. All right, so anything else on the lead side of things? Because the personalization stuff, I feel like we barely scratched the surface there because based on how they enter information, I would imagine you can do a whole bunch of stuff. Right. Depending on how many forms fields.
B
Exactly. So that's the one piece that I want to make sure that we say is possible and don't get overwhelmed if you're like, listen, I just turned this thing on. I'm not personalizing 15 versions of it. That's okay. But using the data that you're collecting on that form, you actually can send people either down different paths entirely or just an assigned sales rep is a great example. If you're in Nebraska shopping for a Winnebago, I can literally send the email, the nurture email from the Nebraska Winnebago dealer. Right. It's signed by that person at the bottom. If you have any questions. My name is Bob. Call me Bob. Right. So I think doing little things like that, you know, we think of personalization as being, hi, Jessica, hi, first name, but really valuable. Personalization also makes sure that the content of that email matches what the person is shopping for. So for example, somebody is shopping for a Travato for Winnebago. If we send them the brochure for an Adventurer, what are we even doing? That doesn't even make sense. Right. So really using the data of where somebody is on your site, what does that mean? They're interested in who's getting assigned to that person who should be signing the email. Then frankly, using what they click on in that email, if nothing else, if we don't know if they're this product or this product, that first email, what they click on could actually give the salesperson some direction on what that person is most interested in. We could use that to personalize future emails.
A
I think what I'm hearing you say, and I know that a lot of software tools out there allow this. Like if you have a website with a bazillion different articles on it and they come in off A specific article you should know they came in off that article. So for example, in our system we have articles on everything you can imagine. So if they're on a page related to Facebook, we can tell that versus Instagram. And if we wanted to, we could kind of flag them as interested in Facebook because they came in on that page and then we could customize the message. Hey, we know you're interested in Facebook. Did you know that we have a bunch of content at Social Media Marketing World that's Facebook focused? That's kind of what we're talking about here.
B
Bingo. Exactly right. And it can either be done through all of the AI and machine learning and automatic dynamic content. You can get into fancy tools or you can just say if this is the page you were on and this is the piece you downloaded. I'm going to suggest these two other things in follow up emails. It can be manual for lack of a better word. The automation comes in the timing. Right. Here's the thing you wanted. Ah. Two days later. Did you know we also have. Right. So we're kind of still giving them reasons to come back and engage with us, especially as a content driven organization like you guys are.
A
When it comes to forms, the obvious things are name and email address so you can personalize the email over the years. Like HubSpot is great at this. They ask a bazillion questions. I don't, I'm not a big fan of that because I feel like every question is a barrier for someone filling out the form. But they say they justify this because obviously we know what they're doing. They're hunting for qualified leads for their sales team. But what's your general take on how much information should be drop down menu choices or check boxes versus like, like discerned through actions of the user.
B
So it's gotta be a balance. If I don't have enough information to send you the relevant email that you're actually looking for, then I didn't collect enough. But the truth is more than four fields on the first signup form is probably too many. Like all of this is friction, right? Do I really want to give you my contact information request? A demo is different. But as long as we're talking about gated content content, we keep those pretty short in my world. It could be first name, company, email address. I don't really have a use for last name mostly. You talked about HubSpot for example. There are platforms out there that will tell you the rest of what you need to know about that person. Oh, Jessica with Better app. Her last name is Best. She's been doing email marketing for 20 years. She has one company, one employee at her company. I mean, we can fill in a lot of information now with some of the data systems there. And so so that I think starting simply and either paying for additional information to be appended or just asking for more information later, either with clicks like you said, or a progressive profile approach, which HubSpot actually, as an email platform has that built in. If you go to my HR client that we were talking about, if you go to their website and you've already downloaded a white paper, it says, are you still jessetterav.com and if so, tell us how many employees you have. It asks one more question. Instead of asking for the same form fill every single time. That progressive capture is actually a really sneaky way to keep friction really low, but still continually get to know that prospect better.
A
Wow, that's really cool. I had another question, but I got totally caught in the progressive capture thing. I thought that was really cool. I've never heard of that before. I can't think of what the other question was, but I knew it was a really important question. But it's going to have to come back to me. So if it does, I will interject and ask what that question was somewhere in the next question here.
B
I love that I said such an amazing answer that it literally made you.
A
I had a really important question and it just went poof when you said progressive capture because I was like, whoa, I've never heard of such a thing. Okay, so so far, here's what we've talked about. We've talked about the initial onboarding email, when with like a welcome series. Then we've talked about lead forms, which is really, really important. Oh, I know what it was. Okay. See, I knew it would come back to me. You mentioned earlier business email and I've seen some websites where, because, you know, everybody has their junk email, maybe it's their Gmail account or their Hotmail account or whatever. How do they do that? How do they. I feel like that's smart, but us marketers need to understand, like, how in the world do email platforms have a checkbox generally that says do not accept generic email, aol, Hotmail, Gmail accounts, and only a business like. Tell us a little bit on the wisdom of that.
B
Yeah, so most of my clients don't actually need to exclude those because if all that's going to them is marketing automation, it didn't cost us anything.
A
Right.
B
So even if there's an Auto fill or it's a student. Ah, you can have the content for free. I don't really care. We just wouldn't assign that person to a sales rep. So it's more like rules on the backside. If fewer than 10 employees or a edu email address or gmail.com, we're just not going to assign that person, but they can still have our content for free. And if they reply and it's like, hey, I'm actually the like CEO of Coca Cola, but I'm using my Gmail address on accident, like, oh, well then yeah, let's, let's hang out, let's talk.
A
Yeah, because I don't, I'm using my personal address or whatever. Okay, yeah, I, I see what you're saying. I like this a lot. So what I'm hearing you say is that like, hey, if you're actually fishing for leads and they don't put their company email address in there, maybe throw them into a nurture sequence and then when they, they hit a series of actions that qualify them through a different route, then bring them back to the sales team. Is that kind of what I'm hearing you say? If they're on like a welcome sequence or a newsletter or something like that?
B
Absolutely. And I think you just have to be really stringent about how you're scoring that because you might get a student email address that's really engaged that would otherwise have a really high lead score, but you still don't really want to call them. So if they're clicking on the right things again, I'll stick with the HR example. X. At hr, they have high value clicks. So like they've got like free content about legal risk and some of these other. But they also have high value clicks like what to look for when hiring a PEO firm that is a shopping click. Like that person is ready to talk. And even if it's a Gmail address, it's probably worth sending that one to the sales team. Right. Because that action is so strong. So yeah, I think you just have to have a good sense of what you're defining as engagement or what you're defining as. Okay, that one's ready, that one's cooked. Let's send them to sales.
A
Well, and I would imagine if you decided to want to enforce this business email address only, there must be tools that do that because I've seen it, I don't know how the world it works well.
B
So I'll just give you this. This is like the Santa Claus doesn't exist. It's not that the form is validating whether it's business or not. It's domain based.
A
Ah. Aol, Hotmail, Gmail, those basic ones.
B
Yeah. Which is a. Not. I mean it's, it's a blunt object, but it's not actually a bad way to go about it because most likely if you're giving me a Yahoo address, you, you're not the CEO of Coca Cola.
A
Right.
B
So, yeah, it's, it's an okay filter for our use case.
A
Okay, let's now talk about people who have actually made a purchase because this is a whole can of worms that most people don't even understand. So talk to me a little bit about what our options are. Let's say they just bought your consumer product or whatever. You know what I mean? Whatever the product is you're selling or service you're selling off your website. Like, talk to me a little bit about what automation can do here.
B
Yeah, so this is again a big gap that I see when I talk to folks on the road. We're really good at nurturing people by email until they buy something. And then they were like, okay, thanks.
A
That's no longer my job because I'm marketing. Right. And that's somebody else's job. Right?
B
Well, a little bit, but. So I'll, I'll go back to the Winnebago example. We looked in their, their database, their numbers. 70% of the people that will buy a Winnebago this year already own a Winnebago right now their best prospects are the people on their list already are the owners that are in their database already. And if they're not sort of welcoming them on board, there's a missed opportunity there. So new customer or new product owner onboarding. Right. So this is almost like the welcome email, but to the next level because this person has literally done the exact thing you wanted them to do and they might do it again if you're nice to them. So new customers sort of of post purchase, are you pleased with your purchase? Do you need assistance with your purchase? Frankly, one of my favorites is doing a post purchase customer satisfaction survey or NPS NET Promoter Score survey, which is just a one question customer satisfaction survey. And then if that person is really satisfied, what's the next thing we can ask for? Right. What's the thing we're marketing for? It's a review or a referral. Right. We're asking somebody if they're happy and then if they are, we're putting them back into the content library as a really Satisfied customer or a five star review or whatever that is. So that first thing I think onboarding new clients and still making one more ask. But also, you know, between you and me, I would almost rather know right away if somebody is unhappy. So even though it doesn't give me a marketing five star review, if I get the results back from that customer satisfaction survey and they are a 2 out of 10, I gotta know that because I am never going to get to cross sell. I'm never going to resell that person on the brand again until I fix that issue. So right after that purchase there's that moment where we're really trying to both welcome them to the family of brands and to the experience and to kind of help them have the best experience possible. But we also got to ask them how was your experience?
A
You have some examples maybe you want to share here?
B
Yeah, well my favorite is I got to work on. There was a Mercedes Benz dealership in Kansas City and Mercedes Benz brand is the best or nothing. So like they have a customer satisfaction survey after you purchase a Mercedes and unless you say you were 10 out of 10 happy, somebody calls you a 9 is not good enough. It has to be a 10. Now if you score them a 10 out of 10 and most people did, then they would send you a second follow up email that says thank you. That is so wonderful to hear that you had such a great experience. Here is our Google review link link for you. Right. Notice we don't ask for the review until we're sure that you are a 10 out of 10 happy customer. So Mercedes Benz was one where we kind of set up that neat automation and a lot of platforms are starting to I think give you that as an out of the box template. Send the survey if a 9 or 10 send the follow up request for a review or a referral.
A
Yeah, it's interesting because I do see these little one to ten boxes all the time and a lot of times I don't even click them and I would imagine if no one clicks them you could send it down another sequence. Right. Like you could just assume if they don't click it maybe they're not willing to give you the negative feedback. Right. So maybe that's another route you could send them down. Now you were also when we were prepping for this, talking about cross selling and stuff like that. I would love to hear a little bit about that.
B
Yeah. So the post purchase cross sell is one of the like go to money making email marketing automation campaigns. You bought this, this a toilet seat do you also need a toilet? So my least favorite version of marketing automation is those people that buy a toilet and then they get nurtured to buy other toilets. They may also like Michael, how many toilets do I need?
A
You need just enough.
B
Just, just the one, just the one that I just bought. So I think there's a bad way to do this sort of lookalike suggestion modeling. But if we can get to things you might like that go with your purchase. Right. And I love an example from the retail space at home was a client of mine when I was at Barkley and they actually paid for software like a SaaS plugin that did this both on their website and in email. You didn't have to buy it, you could actually abandon it like cart abandonment or page abandonment. And it would say, oh, I saw you were looking at this rug, do you like these instead? Right. Again, if they bought the rug, selling them a second rug, very low probability. But if they didn't buy the rug, selling them a different rug. Oh, did you need a different size? Or if this is your style, try these others that you may also like. That lookalike model was something that absolutely paid them back when they invested in a tool like that.
A
And I would imagine if you have lots of products, this could become an automation nightmare almost. Right. Is this where a lot of third party tools come in and help out?
B
Yeah, absolutely. And Frankly they had 50,000 SKUs. But I would say even if you have have 50 SKUs, I don't want to do that matchback or that, that matchup manually. For Winnebago it was kind of straightforward. Right. If you buy a class B camper van, statistically I know you're gonna buy a class B camper van the next time too. But if you buy a class C sort of that traditional Winnebago that makes a C over the cab, you're actually as likely to upgrade to the class A like the big Taylor Swift tour bus sized van as you are to buy another class C. So I actually might show different options based on what I know you own now, which I have in my database. Right, but there's only those three categories. It's not like, I mean they have a total of 14 products. Once you get to at home and you start talking about thousands of SKUs, there's not a great way to do that manually and I don't recommend it. It probably will pay you back to start looking at these third party tools. Like I said, the one that at Home used is called Certon and it actually plugged into both their website and their emails. So when you're on a product on the website, the you may also like section filled in on the website too. So it's sort of dual use that way.
A
Just out of curiosity, does AI, and I know this wasn't part of my questions, but does AI play a role in any of this now? Because, you know, I've got another show called AI Explored and there's so much you can do now with automation, agents, agentic kind of stuff, stuff research and all this. I mean, like, are you starting to like see this coming into the world of email automation?
B
Yeah. So actually, I mean, not to brag, but email marketing has been doing AI and machine learning led automation and triggers for a long time. So just what we were just talking about, Sertona, is machine learning and AI. It's literally letting the computer figure out what the correlation is instead of the human having to do it. So that that level of AI or that system of AI, I think is something that's so embedded in, in our marketing brains that it doesn't seem like maybe it's the same thing and it's not the same as generative AI or agentic AI, but it is the same idea of why don't you just tell me what the right answer is computer that has all the data in it and it will actually give you the quote right answer or those segments or bubbles that you need to be able to market to without a human being having to ask it questions or prompt it it or whatever. Right. We're using a system that already knows how to find the next best recommendation.
A
Well, and if we think about a lot of these email platforms that we use, they're almost like a big old database with all sorts. They are a database of not just email addresses, but all the actions that prospects and customers have taken. And I would imagine they're all working on some sort of AI analysis to help identify the people in the database that are the most likely prospects. Right. And then you can just go ahead and have those messages kind of even slightly customized behind the scenes. Are you seeing that coming out from a lot of the email platforms?
B
Yeah, and actually again, it's not even entirely new. So I think probably five, six, seven years ago, Salesforce Marketing Cloud rolled up sort of their quote AI and their email platform. And it was very underwhelming because all it was was your top 25 most engaged and your lowest 25 engaged. And I was like, I could have done that with a SORT feature. But thank you for trying. So they are now, I think, progressing into flight risk. Right? Like likely risk of no longer being engaged so that we can catch somebody before they just stop checking that email address. I think we're, we're also seeing to what you're saying. The point that you make is can you actually kind of listen to what Jessica clicks and then just decide what Jessica should get next? For me right now, that's pretty third party driven, but I can see that a lot of especially larger email platforms are looking to either roll up or own products that do that so they can just plug it right in.
A
Jessica Best, we have only scratched the surface of that mind of yours and I know a lot of people are going to want to reach out to you if you have a preferred social platform, share where they can connect with you and then if they want to potentially do business with you, where do you want to send them?
B
Yeah, LinkedIn all day, both answers. You can find me Jessica Best on LinkedIn. I might be the only one with a big green stage behind me in my profile and I spend a lot of my time there. For me, social media has been a great way to actually, like, learn and connect. And so I get a lot out of LinkedIn. That's where I spend a lot of my time. And I'd be happy to connect with anybody that's listening, so. Or you can find me on my website. You can actually go to Jessica Best to see my speaker website. When Dot Best came available on the market, I was like, oh, I have to have it. And so I bought the domain Jessica Best, which you can also reach out to me through.
A
Very cool, Jessica. Thank you so much for sharing your insights and wisdom with us today.
B
I'm happy to do it. Thanks for having me, Michael. This was so fun.
A
Hey, if you missed anything, we took all the notes for you over@socialmediaexaminer.com 688. If you're new to the show, be sure to follow us. If you've been a listener for a little while, we would love a review and do let your friends know about it. Also. Also, we've got some other shows. Check out the AI Explored podcast hosted by me and the Social Media Marketing Talk show. This brings us to the end of the Social Media Marketing Podcast. I'm your host, Michael Stelzner. I'll be back with you next week. I hope you make the best out of your day and may your marketing keep evolving. The Social Media Marketing Podcast is a production of Social Media Examiner. This is the year to finally come to Social Media Marketing World 2026. Grab your tickets right now. Now by visiting socialmediamarketingworld info.
Title: Email Marketing Automation That Moves People to Action
Host: Michael Stelzner (Social Media Examiner)
Guest: Jessica Best (Founder, Better Ave)
Date: October 16, 2025
This episode dives into the world of email marketing automation—how to move beyond basic newsletters into impactful automated communications that trigger the right behaviors at the right time. Jessica Best, a seasoned email strategist, shares frameworks, actionable examples, and her philosophy on building automations that genuinely drive leads, conversions, and long-term customer engagement.
| Timestamp | Segment | |-------------|-------------------------------------------------------------------------------------| | 03:56 | Jessica’s personal journey into email marketing | | 06:16 | The “ROI” of email and why automation is superior | | 08:22 | Broadcast vs automation defined | | 10:54 | Start with the welcome email/series, why it matters | | 13:38 | What makes a good welcome email—voice, next ask, and offers | | 16:22 | The importance of setting expectations up front | | 19:50 | Sequencing timing for welcome emails | | 21:42 | Lead nurturing—automation’s role in supporting sales | | 26:16 | Winnebago's nurture sequence and measurable ROI | | 29:38 | To gate or not gate downloadable content | | 31:49 | Personalization opportunities using captured data | | 34:59 | Form strategy: friction, progressive profiling | | 39:42 | Filtering/non-business emails in automation flows | | 40:29 | Post-purchase onboarding and survey automation | | 42:44 | Mercedes-Benz NPS and review automation | | 44:03 | Cross-sell and recommendation examples, automation at scale | | 47:06 | AI and ML’s long history in email marketing, future potential | | 49:44 | How to connect with Jessica Best |
Email automation presents a massive opportunity beyond sending newsletters: it’s about meeting users at their most engaged moments with just the right message, automated for scale, but crafted for personal relevance. Done well, as Jessica Best’s stories reveal, it drives formidable ROI, supports sales, increases customer loyalty, and expands possibilities for marketers in any industry.