From Inbox to Sales - Proven Automation Tricks You Need Now
Are you ready to elevate your digital marketing in 2025? In this episode of Digital Marketing Stories, Perry Sheraw email marketing expert and automation strategist joins host Jim Banks to dive deep into the latest trends, game-changing tools, and proven strategies for turning your email list into a revenue powerhouse.
From leveraging AI for advanced personalization to practical segmentation tactics and platform recommendations (HubSpot, Klaviyo, Shopify), get actionable tips straight from a seasoned pro.
Whether you're a marketing manager at a growing e-commerce brand, a B2B leader, or a digital marketing enthusiast, this episode delivers the strategies you need to succeed in the evolving digital landscape.
Are you ready to elevate your digital marketing in 2025?
In this episode of Digital Marketing Stories, Perry Sheraw—email marketing expert and automation strategist—joins host Jim Banks to dive deep into the latest trends, game-changing tools, and proven strategies for turning your email list into a revenue powerhouse.
From leveraging AI for advanced personalization to practical segmentation tactics and platform recommendations (HubSpot, Klaviyo, Shopify), get actionable tips straight from a seasoned pro.
Whether you're a marketing manager at a growing e-commerce brand, a B2B leader, or a digital marketing enthusiast, this episode delivers the strategies you need to succeed in the evolving digital landscape.
Important Notes
This is Digital Marketing Stories on Bad Decisions with Jim Banks, the weekly podcast for digital marketers who want to learn from the best.
New episodes are released every Wednesday at 2PM GMT where you'll get digital marketing stories and anecdotes along with bad decisions and success stories from digital marketing guests who've been there and done that in many of the disciplines that make up the discipline of digital marketing.
The podcast is powered by Captivate and all the ums, and ers have been removed using Descript to make your listening more enjoyable.
Some of the snappy titles, introductions, transcripts were created using AI Magic via Castmagic
Disclaimer: some of the links on the show notes of my podcast are affiliate links.
If you click and buy from any of these links, I may receive a commission as a result of your action.
Jim Banks [00:00:00]:
Hello there and welcome to this episode of digital marketing stories. I'm delighted today to have Perry. I always butchered people's names. Is it Sheraw or how do you pronounce your last name?
Perry Sheraw [00:00:09]:
Yes, Sheraw.
Jim Banks [00:00:11]:
There we go. Yeah. I always think sometimes people say, do you choose the people to come onto the podcast specifically based on the complexity of their names to pronounce or not? But anyway, it's like I say, no, generally speaking. I just want to have great guests who have great stories and great background. So Perry, it's great to have you on the show today.
Perry Sheraw [00:00:27]:
Great to be here. Thank you so much.
Jim Banks [00:00:28]:
We were just talking in agreement a little while ago. Perry was saying I'm based Salisbury. She was saying she was in Salisbury a couple of years ago in Salisbury Cathedral. So. But where is it you're calling in from today?
Perry Sheraw [00:00:37]:
I'm calling in from St. Croix in the U. S. Virgin Island.
Jim Banks [00:00:40]:
And what's it, what's it like there?
Perry Sheraw [00:00:41]:
It's beautiful, probably 86 and sunny and gorgeous. Caribbean water all.
Jim Banks [00:00:48]:
But you get like lots of hurricanes and things like that. Is that kind of the. The pain that you have to deal with?
Perry Sheraw [00:00:52]:
Well, the hurricanes really, yes, when they come, it's bad. But I've lived here 25 years and knock on wood, we've had two really bad ones. So it's not like they come all the time. It's more, if you're talking pain points, it's more the answers, the need for a lot of redundancy. For example, we always, we have a backup generator that comes on when the power goes out, that sort of thing. And two Internet services, expensive groceries. It's. That's more of the paradise tax as we call it.
Jim Banks [00:01:21]:
Do you find in. In life there's generally trade offs, aren't there? Like you have one thing but you have to trade off something else as a. As a result of that. But obviously I was delighted to have you on today to talk primarily, I mean like. So your expertise like sits in marketing automation. Looks like you've been doing email marketing for forever. Perhaps you can just tell us a little bit about your background.
Perry Sheraw [00:01:39]:
Yeah, absolutely. I started in print journalism in the 90s. I was a news reporter in Cincinnati and also in Lexington, Kentucky. And then I moved to the Virgin Islands and gave it all up and had my first retirement and then ended up working a company that was based here and ended up running their marketing program. And at the time there was no marketing automation platform. There was barely an email deployment system. And so I started to piece together the idea that we could have this cohesive conversation from marketing all the way through to sales and that that would ultimately help close deals. And of course there were some thought leaders, it was harder to get to that.
Perry Sheraw [00:02:19]:
It was all book based at the time, but some thought leaders that definitely agreed with that. And I worked with it in that company to craft a kind of Frankenstein version of SA sales logics at the time and create something that was very similar to HubSpot today, but a very rudimentary version of it.
Jim Banks [00:02:38]:
So what I mean, like, I mean I've been using HubSpot for, for a long time. Like for me it's been my CRM of choice. But yeah, to your point, in the olden days I used to use all sorts of different Frankenstein monster type CRM solutions to try and kind of capture information. And again, in my sort of very early days of selling insurance for a living, everything I used to have on an index card I had like a plastic box with all these index cards on file, alphabetically by name, all written down, peoples' names and all that sort of stuff. What, what sort of, what do you think have been the biggest changes? Clearly we're, we're inundated with AI at the moment. What, apart from that, what would you say have been the biggest changes in email marketing over the years?
Perry Sheraw [00:03:13]:
I think the biggest change and the biggest challenge is the ability to be so nimble. And so the challenge now is the companies that are doing that are causing the consumer to say, wow, this company doesn't even know who I am. They're noticing and they're expecting you to know who they are. And if you're not stepping up to that challenge, it's going to show. And I think that for a lot of companies causes them to seek marketing automation experts and try and create a more valuable and helpful experience for consumers.
Jim Banks [00:03:46]:
So one of the biggest challenges. So I primarily run paid advertising for clients, but I kind of like have a bit of an oversight into some of the marketing that goes on on the email side of things. Because I think one of the challenges, a lot of people think that email sits in isolation and typically we find that it does better when all of the kind of chann cohesively work together towards the same outcome. Right. So paid media doesn't work in a silo, email doesn't work in a silo, SEO doesn't work in a silo. Right. Everything works together.
Perry Sheraw [00:04:13]:
Yes.
Jim Banks [00:04:14]:
How are you, how are you using AI in today's world for, for that sort of, to try Try and bring some of that cohesion together in one place.
Perry Sheraw [00:04:21]:
Well, I think there's two pieces to that answer, right? There's the tried and true seven touch points of marketing, right? You know that my father ran an advertising agency in the 70s and it was, I was a thing then. That's where it came from. But the other piece to that is that we can transfer that data from platform to platform more efficiently through AI, and we can analyze all of those touch points in that data more efficiently through AI, which basically elevates our ability to respond more real time. And that's something that marketing automation platforms like HubSpot have been doing for a number of years already. But it's just making those that were doing it before better at it. And it's removing a lot of the manual download upload lists between platforms.
Jim Banks [00:05:07]:
So. So for me, one of the biggest challenges is you kind of hit the nail on the head. Consumers expect you to know who they are, right? And nothing gets my goat up more than when people are writing to you. And either that they're doing one or two things, they're either being very familiar in advance of when they should be, right, Because I don't know who they are and everything else. And they're, hey, you come on the putting up a chair, somebody having dinner and they're putting up a chair to sit down and join me, right? And I'm like, whoa, I don't even know who you are, right? So. But equally right, there are people who know who I am but don't actually talk to me like they do. It's almost like they've got sort of a, some sort of brain fog going on where they don't understand kind of anything. The classic example here in the UK we have something called the National Health Service.
Jim Banks [00:05:45]:
And the National Health Service is all about your medical. And I get emails from the National Health Service through, through one of their sort of solutions. And everything talks about this is what happens when you're going through the menopause and when you get your periods. And I'm like, you know any about me? I'm really concerned if that's what they're, they're writing to me about, right? They should be writing to me about the things that are based on my medical records, right? They should say, you need to lose weight, you need to do this and you do that. They should, they should be able to say based on what they know about me, that that's what they should be doing. So I think as much as email marketing has been traditionally a kind of a blasting solution. I think now we're at the point where it really needs to be laser targeted and focused in on individuals and what what you know about them based on the past and what you can make some presumptions about the future for them and present solutions for them that way.
Perry Sheraw [00:06:27]:
I agree completely when we're talking about some of the HIPAA compliant solutions that are available like HubSpot now, thankfully being HIPAA compliant, right. We can talk to people even in that HIPAA compliant environment on a much more personal level based on the demographics and the personal information that we know about them in a safe and secure environment because theoretically, because HubSpot is HIPAA compliant and so larger companies especially or even medium sized companies, I work with a lot of med device companies, those who are taking that have a compliant environment coupled with the workflows coupled with digital marketing and AI to process data and to really understand the insights about that contact are the ones that are winning. They're having the engagement.
Jim Banks [00:07:15]:
So. But when I was researching your your profile, I noticed that you're in the. Are you in the process of writing a book or have you written the.
Perry Sheraw [00:07:21]:
I'm in the process of writing a book. I am. And, and really it's going to be geared toward marketing managers, primarily those who are at medium sized to small businesses who are trying to source proper technology and helping them make the case for it and develop the ROI for it. For example, someone trying to go from Mailchimp to a hub or something like that for their company because it is. I always say my stock line is it's all about the conversation. It's really hard to do that with just blasts. And so I think it will elevate. I'm hoping the book will help elevate the experience not just for those marketing managers but also for the consumers that they're serving because it really should be more helpful.
Perry Sheraw [00:08:07]:
And that is something that will help longevity with email and the channel itself if people can just really start to elevate their use of it and make it more personal.
Jim Banks [00:08:16]:
So I always ask this. I got so many of my friends that I know have written books and to a person, right, Every single one of them has said with the benefits of hindsight, it was probably one of the stupidest things they've ever done. What for you, what was the kind of itch you were looking to scratch in terms of wanting to write a book?
Perry Sheraw [00:08:33]:
Well, I definitely would like to have. I I'll just be honest. There's some credibility related to writing the book. I think that it also is an exercise in self discipline to gather the materials that I'm looking to only use on my upcoming YouTube channel and just developing my brand. It's, it's, it's, it almost is just the, the itch that you're talking about is just get my act together, get my material together and just move my personal branding forward.
Jim Banks [00:09:04]:
Yeah, because I know a lot of people who have used the writing a book as a, as a sort of springboard to then get onto the speaking circuit, doing kind of keynotes and things like that. Because usually like event organizers, in order to kind of book you as a speaker, they'll probably have to commit to buying a certain number of books. Books again. I've talked to so many of my friends who started life in the black SEO sphere and they found out all the gamification ways of becoming a bestselling author. And I'm like, again, if I was going to do it, I'd want to do it and become a best selling author because it's a good book rather than just because I was, I knew how to game the system.
Perry Sheraw [00:09:35]:
So yeah, it's, it's a little bit, it's such a funny time too for books. I know that there are other podcasts that talk about whether it's, there's even any value in it anymore. Is anybody reading these? Etc. And so I don't know the series out on it, but I wouldn't mind getting on like a speaker circuit doing a little bit of that. Although I also think that is a little, it's fading out of existence but maybe it's coming back. I know that conferences are starting to come back as well and so I think what I'm really excited about though is launching my YouTube channel in the first quarter of next year and it's.
Jim Banks [00:10:15]:
Going to need a context to that.
Perry Sheraw [00:10:16]:
That will be a comparison complete kind of course driven proposition where I share how to whether it's about HubSpot, whether it's about Klaviyo and E commerce, but just basically getting down into the nitty gritty of email deliverability, email design, which I think is woefully underserved in a lot of medium sized businesses and also just talking to people on a personal level utilizing the data that you have. So personalization.
Jim Banks [00:10:45]:
I used to be a sort of high volume mailer back in the day, but technically I was just a spammer. Right, Right. But, but I used to send a lot of emails in the affiliate space and what was really interesting and challenging for me was we had a lot of emails to send and we worked on the kind of high, high volume, low, low profitability in terms of success in the emails that we sent out. But one of the things that became really apparent was that ultimately it became about getting into the inbox, right? And if you couldn't get into the inbox, it didn't matter how well designed your, your, your emails were. And one of the challenges I find sometimes when you're working with a CRM solution like a HubSpot where they give you email marketing capabilities, one, I find it very expensive and two, I just don't necessarily think that that's their core kind of business. They call businesses the CRM piece of it. And I think the email side of things becomes less of a. It's part of the solution, but it's not the best part of the solution.
Jim Banks [00:11:35]:
So what do you recommend? You recommend sticking with the CRM for HubSpot on its own and then having something like a Klaviyo as a sort of separate or do you have everything all in the hub ecosystem?
Perry Sheraw [00:11:46]:
Yeah, that's a good question. Klaviyo is definitely digital commerce and if you're doing E commerce, you should be using Klaviyo. Some very complex E commerce will use HubSpot and HubSpot's been developing that section of their business. But for the most part, if you're using Shopify and doing online digital commerce, you should be using Shopify and Klaviyo. They almost. They are, they were, they started as native integrations and I know Shopify is building on its own thing now, but the functionality and Klaviyo and Shopify can't be beat. Their, their dream team. Now over on the HubSpot side of things, HubSpot's been doing email ever since 2002.
Perry Sheraw [00:12:23]:
So when you're talking HubSpot, I think that they are very effective at email. They're not effective at cold email and kind of inboxing that way. And I have a totally different approach when it comes to say, purchase list or folks that, you know, haven't given you the email for a purchase or at a trade show where they understand and expect they're going to email to you. But for marketing emails where you're not too worried about ending up in the promotions folder, most of the HubSpot's of the world maybe act on activecampaign. They actually have deliverability teams though that will work with you. If you find that you're going into spam and then it becomes all about helpful conversations that will continue to have people click and open.
Jim Banks [00:13:08]:
Yeah, I was, I always find it sometimes like, because I use HubSpot for my business and use it for email as well and they have that tracking capability. And it's always interesting, like when, when you see the alert come up to say somebody's opened an email, somebody's clicked on a link or whatever it might be, I always get giddy with excitement because I'm thinking, what's coming next? And I don't know, do you kind of have the same sort of excitement when you see something actually come to fruition? You go, this is my plan. And then it actually executes that way and you're thinking, well, that's great. Do you get the same feeling?
Perry Sheraw [00:13:33]:
Totally get the same feeling. I love that, I love that. And I had to train myself out of refresh, refresh, refresh for open rates and click through and all of that. And that's another thing though, that kind of joy coming from some of the deeper tracking and analytics that we can get today. It goes all the way through, especially if you're looking. Going back to Klaviyo. One of the things that just got me so excited after spending a lot of my career in B2B was getting into Klaviyo and Shopify and then not just seeing performance data on the emails, but seeing revenue attribution right there on the dashboard is so exciting to see. We have some clients that will send an email and we'll get $81,000 off of the email in 24 hours.
Perry Sheraw [00:14:17]:
And it's just great. We did it. And so I love it.
Jim Banks [00:14:20]:
So I, I. In the same way that we talk about the segmentation of your audience and everything. Right. I think sometimes the best way to get the best value out of your email platform is to understand who you have in your database and create lists that you can then use again. I've always said it much better to have a small list of like people that absolutely spot on for a particular initiative rather than sending an email to your whole audience and ending up with a massive, massively high unsubscribe rate. What are the sort of lists that you think, say E commerce businesses should have in order to be successful with email marketing platforms?
Perry Sheraw [00:14:52]:
Yeah, absolutely. You need your prospective purchasers list, list your past purchasers, list existing customers, if that is a thing. If it's not just a single transaction, you need your replenishment. So hopefully you've got some kind of subscribe and save program on our loyalty program. So you need a replenishment list. To let them know that they're about to run out of your product, that sort of thing. So those are really key top level segments that you want to approach. But then let's get into some specifics.
Perry Sheraw [00:15:23]:
If someone traditionally orders products that are related to skin care, then let's make sure that we're using dynamic content and have them segmented in a way that says for this segment, insert this skincare product that we've just launched. For this segment, insert this heart health product that we've just launched. That sort of segmentation. Because that's when it really gets personal. A lot of times people think personalization still to this day is more about hi and not putting in sender or recipient and messing up.
Jim Banks [00:15:57]:
Square brackets, first name. Exactly.
Perry Sheraw [00:15:59]:
We've all gotten them. So some people think just getting that right is a win for personalization. But you know, we just have the ability to go so much deeper now. And the content that you present should be set up in a dynamic way. Even in a small scale you can do this. Set it up in a dynamic way that really shows them what you think from the data that they're going to be entering interested in.
Jim Banks [00:16:20]:
I've always found marketers are the easiest people to market to. Even though I know exactly what people are doing, I still fall for it most of the time.
Perry Sheraw [00:16:27]:
And, and how about those phone calls? I stay on those phone calls. I'm like, yeah. And then I sometimes go into the critique, I'm like, oh, if you'd asked me this way.
Jim Banks [00:16:36]:
Yeah, yeah. I always, I always find the like so many people will try and use a different approach for cold email where they don't know who you are. And they'll try and use a bit of humor or a bit of this or a bit of that. And it's like as soon as I receive an unsolicited email approach, I'm like, report sp, I'm done. Because for me, if they want to get in touch with me, there's so many better ways of doing it than just trying to find a place to grab my email. My email's out there a lot, right. So it's easy to find. But you know, it's like that doesn't mean that just because you have it, you have permission to use it.
Perry Sheraw [00:17:04]:
So no, it's true. I really. And over the years I've had management has passed down in different scenarios. Hey, my brother's cousin got this list, let's take this and send to them. And I'm no, that's a terrible idea. But you know, sometimes you have to. In one scenario like that we did, and it shut down not only our deployment system but the website because they've, they reported it all the way up to GoDaddy when it shut down our website because we weren't built to be that kind of spammy marketing organization. And so that was many years ago.
Perry Sheraw [00:17:40]:
But it is best to work with, even if you're working, it's best to work with people that want to hear from you. And, and, and, and the one tricky part is some people may want to hear from you, but they're not going to respond to you every time you send. So finding that right cadence so that you keep your list warm, don't overuse it, don't burn it, but also don't throw people out of your list without factoring in things like seasonality and the amount of times of year they might need your digital marketing service, that sort of thing. So that's, it's a balance.
Jim Banks [00:18:14]:
Absolutely. And, and I again, I think the, the biggest challenge sometimes is I, I think in the same way that you're talking launching a YouTube channel, I've been doing so much analysis of YouTube as a, as a, as a distribution method for people, right? And there's clearly a lot of people doing incredibly well with YouTube as a solution. And every single person says it's all about the packaging, right? Because the packaging is good of creating the best video in the world. And I, I've seen it, I've seen examples of big marketing conferences that take place in Singapore. They've got people like Martin Sorrel as, as the guest keynote speaker. He's doing a fire fireside chat. You look at this YouTube video, it's got 27 views, right? And you're thinking why on earth would such a great speaker talking about a great pick such for view rate. And when you look at it, it's the packaging, right? Because ultimately the packaging for YouTube videos, it's about the title of the video.
Jim Banks [00:19:00]:
It's about the thumbnail, right? If you don't have the title and thumbnail, right, it doesn't matter how good the content is, people are not going to click through. And in some respects that's the same thing with email, right? It's all about the packaging, right? It's about the design, yes. But it's also about what is the subject line of that. Because in most cases if people are on a mobile, that's all they see, right? They see the title, subject line of the email. And in some cases I use the subject line as a means of saying, saying spam. No, it's, it's not going to be of any value. I'm not even going to open the email at all. I'm just going to send it straight to junk.
Perry Sheraw [00:19:28]:
Yeah, absolutely. And I was on the YouTube front. I was on a conference call, I'm sorry, a podcast of someone named James Allen, and he's very focused on YouTube video production. And he said the exact same thing that it's all about your thumbnail, your title. Just getting those keywords into your title and making it really straight, speak to the audience that you're looking to grab. So he's somebody really great to check out when you're doing your research, if you haven't already come across him.
Jim Banks [00:19:57]:
...I changed it to digital marketing stories because everyone has a story to tell, right? And sometimes stories are good, sometimes, sometimes they're not so good. It was originally supposed to be about people's mistakes, right? But everyone has made them and in some respect is everyone's story kind of talks about the things they've done well and the things they've done not so well and what they learned about and, but, but again, I think in some respects, I look at some of my stats and, and some of the better podcast episodes, even though I've had great guests in every episode, some of them do better than others. And part of the reason for that is because of the, it goes onto YouTube. I use decent thumbnails to do that.
Jim Banks [00:20:47]:
...right? So think about the thumbnail. Think about the title of the video on YouTube, right? And also have a different one in Spotify and a different one in Apple, right? Because they're, they're different in terms of the way they present things and everything else. And it's not always a case of just using the same thing and just going, right, there's one podcast episode and just send it out to the whole world, right? Because every, every platform is different in terms of the way they look at things.
Perry Sheraw [00:21:15]:
Yeah. That is interesting. And I haven't used it enough to know. But of course with email marketing, I mean we a B test as a rule when it comes to subject lines, we'll do things like if we're not a B testing at the actual send level, then sometimes we will pop the subject line and the preview text and see if we can get additional opens on the second on a recent but to non opens. But I wonder, I don't Even know if YouTube has the ability to a B test.
Jim Banks [00:21:45]:
Oh yeah, do they? They do, yeah. And, and one that they give you the ability to upload multiple thumbnails now whereas it used. But you had to upload one. You could switch it out and do that. But I think what you tend to find there's a couple of people. So Mr. Beast, he, he quite often if he doesn't have a good thumbnail and a good title for his video, he doesn't make the video. Even though he, he may have spent millions of dollars making it, if he can't find a good thumbnail and title, he just won't make the video.
Perry Sheraw [00:22:08]:
What a phenomenon.
Jim Banks [00:22:09]:
Yeah. And, and there's a guy called Stephen Bartler who has a podcast called Diary of a CEO. And again he, if you look at the sort of history, virtually every single episode that he creates, right. You look at it and you think, oh that's, that's a good catchy title and thumbnail when you look at it. There are historically there are hundreds in some cases of titles that he's used and multiple variation thumbnails. Right. Just for him to land on the, the ultimately the best one. Right.
Jim Banks [00:22:33]:
Because if you can get the, the right combination then that sort of. You're off to the races at that point. Right. YouTube really helps put it in front of as many people as possible based upon the click through rate from people seeing the title and thumbnail because they don't know how good the actual content is until they get into it. Right. And I've always maintained that whenever people have a video, the first, almost like the first sentence of the video should reinforce whatever it is. It's in the title and the thumbnail that should be reinforced in the first 30 seconds of you talking about whatever it is. Right.
Jim Banks [00:23:02]:
So if the video is going to be about some sort of medical device or whatever it might be. Right. If that's what the title and thumbnail then the first 30 seconds needs to reinforce that. Otherwise people are going to be bouncing out the door as quick as Possible. And that that's going to harm you in the same way that bounce rate harms you on SEO.
Perry Sheraw [00:23:17]:
Right.
Jim Banks [00:23:18]:
Exactly the same thing in YouTube. And it's blown my mind Realiz, just how much similarity there is, even though everyone works in different disciplines. So email to YouTube, whatever it is, everything comes back to that whole thing of packaging. It's. It all boils down to that, really.
Perry Sheraw [00:23:32]:
What is it? We're an attention economy. I think I was just reading about that the other day. And that's really what you're saying, is that if we're not grabbing that attention in the first three, four seconds, we lose it. No. 1. There's so much content.
Jim Banks [00:23:46]:
Yeah. I mean, it's, it's, it's ridiculous how much content is put up now and again, like a lot of people. So I downloaded a piece of software as one of my Black Friday purchases that gives you the ability to put in a YouTube URL. Right. And what it will do is it will go and download the video and extract the script from the video and then basically write a summary for you. So you don't need to even watch the video. You can just download it, transcribe it, summarize it, and if you wanted to, I could probably remake exactly the same video, but just in a completely different way. So it's exactly the same content, just packaged differently.
Perry Sheraw [00:24:17]:
Yeah, it's crazy. It's like, when do we reach a point of diminish? Or have we already reached a point of diminishing returns on all of the volume of content that's out there? It's just, you can't even. You can't even process it. You go down these rabbit holes and you've got this app, that app. I mean, how many apps have I gotten? About. Many apps that I, I have been excited to try, try to a little bit, and then wanted to come back to it. Are you using what. What are your preferred AI platforms right now?
Jim Banks [00:24:44]:
So I, I've played with all of them. Right. So I think I've landed on Claude is my preferred sort of solution. Right. Even though I know that most people kind of have dived into chat GPT. Right. I found when I initially I didn't particularly like it. I know it's, it's evolved a lot since then, but, you know, again, I'm just almost like a digital.
Jim Banks [00:25:02]:
I almost think I'm too old to be using AI in the way some of these young kids are. And I'm. Again, I'm a bit old school. I like, I prefer to see people Touch people rather than. It's all bit done that way. For me when, when Covid happened, I hated the fact that I couldn't go and travel around the world and speak at conferences and meet people, go out for drinks and dinners and things like that because I felt that was really what sort of cemented the relationships that you could forge with people. So some of my best deals have always been done 2 o' clock in the morning with a cocktail at a bar somewhere and all your inhibitions have gone out the window. You can be very forthright and say, look, I think I could do an amazing job for your company.
Jim Banks [00:25:37]:
Why don't we work together and people go the way this guy holds his drink and everything else and yeah, and I think that's part of it. And I think as much as yes, AI is great for helping. For me, I use AI primarily to allow me to continue to do the things that happen face to face without having to spend all my time kind of doing stuff in the background. So that's what I use it for, to help cut down and, and eliminate some of the friction to make life easier for me to do more of the things I enjoy doing. Right. And less of the things that I don't like doing.
Perry Sheraw [00:26:03]:
Yeah.
Jim Banks [00:26:03]:
Editing videos and that sort of thing. I love the conversations. I hate editing the video together. I think it's all part of the marketing.
Perry Sheraw [00:26:08]:
So yeah, that's great. Yeah, I agree. I agree. I've been diving in a little bit to perplexity and I use Claude and chatgpt bounce around between them. Homeschooling my kids gives me a lot of opportunity to work through different platforms, just see what the research. Research what, what works better for which applications. For sure. Yeah.
Jim Banks [00:26:30]:
I mean joy, I mean join using Claude. Right. Because I've done a fair bit with it. I enjoy kind of like configuring MCP so I can put my Google Drive and my notion and email into it and it'll give, it'll spit data out to me, which is great. But equally, I'm also enjoying certain elements of. Of Google Gemini. Right. Again, I find sometimes when you're looking to send a reply to somebody for an email and it's almost written one, you go, I couldn't have written it better myself.
Jim Banks [00:26:54]:
But I think sometimes when you look at things like in the digital marketing world, everything became about UGC, right? User generated content. And so much of the user generated content, one, they're not users, they're not people actually work with that brand. And two, they're not even real people, they're. They're AI generated.
Jim Banks [00:27:25]:
I think if it is a genuine testimonial, right, there should be some way of actually flagging and saying this is actually a real person, right. Rather than an AI generated person.
Perry Sheraw [00:27:37]:
So yeah, I agree, I agree. And I think we'll start to see. It's been so hard for any kind of legal guidance to keep up with technology for what, the last 20 years, really. But it, I do think that the, the end users of these platforms are starting to band together and demand certain transparency for this. And I think that'll just continue to grow for sure. But you know, I wanted to circle back to the sales and just talk a little bit about one of the things that I think has been unique in my career is I've found myself and partly because of where I am in geographically in the world, there has, there is an economic development program sanctioned by Congress that's based here on the US Virgin Islands. So I've been able to work with some really large companies who have quartered here for tax purposes. And that has given me insight and action, access to 200 plus person sales teams and I've handled all the marketing for those teams.
Perry Sheraw [00:28:33]:
And one of the things that I have always focused on is spending as much time as possible listening and hearing how sales interacts with the prospective customer and traveling, doing some of the trade shows and just really getting familiar with the conversation all the way through the customer journey. And I am super curious about how that is going to change with the current technology. Are those 2am meeting meetings still going to happen? And even at smaller scale levels, will those travel budgets, are they gonna, Are they re. Are they coming back after Covid. What are you, what are you seeing with all of that?
Jim Banks [00:29:11]:
Yeah, I just think, I think a lot of companies have just almost given up. When, when I first started out doing kind of what I do, I used to go and speak at conferences and it would literally be, I'd finish speaking, there'd be a room full of decision makers and budget holders, right? And they would come, come and kind of mob me at the back of the auditorium after afterwards saying, I want to work with you. I want to work with you. And I think what's happened now is that obviously the industry has become more mature, right? And I think what tends to happen now is the people that used to be the budget holders and decision makers, they don't go to the conferences anymore. They send their team, and they send their team primarily to learn, right? They're not there to, to find new vendors. They're there primarily to learn the new techniques and everything else. So I think there's a lot of. Again, I've got a lot of friends who still spend a ton of time and money and commitments on the speaker circuit traveling around the world.
Jim Banks [00:29:56]:
So I do tend to go to conferences now, but more, more often than not, most of the time I'll just go and sit in the bar, right? And it's almost become like we call it LobbyCon, right? So I go, I'm there at the time the conference is happening, but I don't actually go into the conferences. There's no point in me going and talking to vendors in the booths. There's no point in me talking to other people.
Jim Banks [00:30:33]:
People who know me, know where I'm going to be. They will come and hang out and have a drink and, and have a chat and everything else. And for me, it's. It's always been. I've picked up plenty of business that way. So it's not like I. I feel I need to have a big booth with a. Leaflets to hand out to people and everything.
Jim Banks [00:30:46]:
But I don't think that's necessarily the way that everyone could do. I think that's just probably a unique bdwjb thing rather than everyone maybe try and do the same thing. Really?
Perry Sheraw [00:30:58]:
Yeah. That's so interesting.
Jim Banks [00:30:59]:
But I think the cost of travel has gone up exponentially. I think it's so much more expensive now to travel. Flights, hotels, everything is like so much more expensive.
Perry Sheraw [00:31:07]:
Yeah, more expensive and more inconvenient, I think, for sure. Wow. Yeah, really interesting. I hope the relationships and the interpersonal. I think as we get further and further away from COVID it's just really interesting to see how the person to person. Person contact will continue to change. It was funny because I pretty much worked remotely here in the middle of the Caribbean since, for, for 18 years, you know, and so I've traveled out some, but I've always been that really comfortable with behind the scenes, the person helping and supporting the people that are going out there face to face. But it was funny when Covid happened.
Perry Sheraw [00:31:44]:
All of a sudden I, I soundproofed my bedroom. I like had locks on the doors. I had like all kinds of things. But it just makes sure people didn't think I was working from my be. But then all of a sudden Covid happens and there's like dogs and babies and it was crazy. It was just a crazy time.
Jim Banks [00:32:02]:
And I think, I think like the, it really gets my goat when, when I watch people on tv, right? So if I, if I watch the news and they're interviewing somebody, it really gets on my nerves because you see these people and they're important people, whether they're politicians or whatever, and they're there and their lighting's horrible, their audio is horrible. Right. The way they frame themselves is horrible. Again, if you look at you and I, we're the same level heads near the top of the screen where get some people, it's almost like they're peeking up from the bottom of the screen about that, that far right, tiny little bit at the bottom. Right, right. And as you say, like you can see the cushions on the bed behind them and everything else. I just think it's, it's. People don't realize how important that sort of thing is.
Jim Banks [00:32:41]:
I've seen myself watching an interview and I'm like, I can't stand up the audio. It sounds tinny. It's. It's dreadful. The lighting's horrible. And I just turned change the channel. And I think that's. I could understand it for.
Jim Banks [00:32:50]:
If you, if you're working in a place like war correspondence, if they're working in Ukraine, you can't expect them to have a whole production studio and everything else. But if you're working again, if you're working from home, there's no reason why you shouldn't have invested in, in your, like I said, your technology, your, Your microphone, your lighting, everything else to make it so that if you do appear on a zoom call that people go, wow, the picture. Virtually everyone I come on to talk to, they go, wow, your picture quality is really good. Audio sounds good. And again, I, I invested heavily in, in that when Covid happened mainly because I was bored. I couldn't go anywhere. So I'm like, I know what I'll do. I'll go and buy some technology, some gear.
Jim Banks [00:33:25]:
Right. And I just ended up spending so much money on lights and cameras and, and everything else. But I, I think eventually it will get to the point where I think probably 40, 50% of the business will be done like remotely without face to face. But I think more and more people will start to go back to face to face. Because they miss it.
Perry Sheraw [00:33:41]:
Yeah. Because we're people. And also though the technology side of it, they just released a study, I'm sure you saw it, that people who have glitchy zoom calls, glitchy scenarios on online are there are perceived as less trustworthy. Which is really interesting. Yeah.
Jim Banks [00:33:59]:
So, Perry, this has been a phenomenal conversation. I've loved having the opportunity to one meet you and to kind of get to talk to you about your background. All of, all of your kind of details will be available in the show notes after we finish up. It just reminds me to say thank you so much for being a fantastic guest. Is there anything you want to leave it in terms of a parting kind of remark to the audience in terms of specifically what you'd like them to reach out to you for if you, if you're looking to provide some help to them?
Perry Sheraw [00:34:21]:
Oh, for sure we are. My SEA is available to assist globally for e commerce activity, whether it's digital marketing automation integration and optimization between Klaviyo and Shopify or B2B marketing device marketing. There are a variety of platforms that we work with. So if you're looking to optimize your communications along the customer journey, that's what we specialize in and I've been doing it for over 20 years. So just look@harryshirra.com and reach out and we'd be happy to do a free consultation and, and get started that way.
Jim Banks [00:34:58]:
Well, it's been great talking to you and for anyone that's watching or listening in, we'll see you on the next episode of digital marketing stories. Thanks a lot. Recording.
Podcast Host
Jim is the CEO of performance-based digital marketing agency Spades Media.
He is also the founder of Elite Media Buyers a 5000 person Facebook Group of Elite Media Buyers.
He is the host of the leading digital marketing podcast Digital Marketing Stories.
Jim is joined by great guests there are some great stories of success and solid life and business lessons.
Managing Partner
Perry Sheraw is a marketing automation expert with over 20 years of experience turning chaotic email strategies into high-converting customer journeys.
A former print journalist turned C-suite executive, Perry launched her first email campaign in 2002 and never looked back.
She has since led marketing strategy for both Fortune 500 companies and scaling startups, with deep specialization in email, SMS, CRM alignment, and marketing tech.
Now the Managing Partner of Duma Marketing, LLC, Perry helps e-commerce and med device brands eliminate communication gaps and unlock consistent revenue through personalized automation.
She’s a certified Shopify and Klaviyo Partner, HubSpot Partner, and has worked extensively in highly regulated industries including HIPAA-compliant marketing.
From running call centers and launching lending funnels to building Frankenstein CRMs before HubSpot existed—Perry has done it all.
And she’s now writing the book (literally) on how brands can finally get email right.


