The Evolution of Email Marketing: How AI is Transforming Lead Generation

C&C Interview Simmonds.mp3

John Gauntt [00:00:06] This is Culture and Code, a podcast about creativity and artificial intelligence. I’m John Gauntt. Culture and Code explores innovation across storytelling, technology and audiences to help professional creators collaborate better with AI and each other. Support this podcast by subscribing to our newsletter. Visit our website, Culture and code.io. This show is a conversation with Shira Simmonds, who is the founder of Smart Reach AI, a lead generation company based in Israel. In her career across multiple companies, Shira has helped build lead generation and sales funnels for over 200 B2B companies, resulting in over 11,000 booked meetings and generating more than $27 million in revenue growth. Now you can find a full bio on our website, Culture and code.io. Now in this show. Shira and I will explore how email has evolved as a B2B sales tool. Specifically, we’ll look at the workflows for researching and crafting personalized email at scale for B2B lead generation. We’ll look at how AI changes the game, plus where the human touch will always be best. So Shira Simmonds, thank you so much for speaking with the Culture and Code Podcast.

Shira Simmonds [00:01:20] Thank you so much, John. I’m so excited to be here.

John Gauntt [00:01:24] Okay. Well, let’s start with Smart Reach AI. Basically, it’s origin story, customer base and its value proposition.

Shira Simmonds [00:01:32] Absolutely. So yeah, I actually have been running a company called SSC Digital for the last 13 years. This is an outbound lead generation marketing agency and we’ve been doing it all manually, full service. Like I said, for the last 13 years. And what we do is we build lists of prospects that meet our client’s ideal customer profile. We craft unique messaging. We send out the messaging both by email and LinkedIn, and we book calls with decision makers that are interested in our client services. And like I said, we’ve been doing it manually for so long. And as AI started coming, I was cooking this idea for like several years, really, how we can do this in a smarter, more automated way, but also go deeper than a human can go in 24 hours. And let’s say working 8 to 10 hour days. And what I really wanted to figure out was, as my team was doing all of our optimizations and reviewing the data every week with our clients and looking at, you know, how many calls is this campaign booking? What is the conversion rate, how many emails and LinkedIn messages do we need to send in order to book these calls? What I really wanted to be able to do was go a little bit deeper and optimize by persona, right? And not just by campaign. So how can I do that? How can I really look and say, okay, for a CEO in the US with 200 employees in the advertising industry, what would be the best subject line? The best call to action? The best tone. And so really that’s where Smart Reach AI was born was around doing deeper analytics and also letting the data lead me in terms of different personas, respond to different offers, the different tones to different lengths, to different subject lines, and how can I build that out in a very smart way without having to spend hundreds of thousands of dollars on data scientists and hours to do that. So that’s where Smart Reach AI was built. So so Smart Reach AI? What it does is it hyper personalizes every single email after it reviews that data. So the first step is it analyzes all that data. It looks at what’s going to be the best makeup of an email for each persona. Then it scrapes each profile’s LinkedIn profile. So it looks like you spend time researching that prospect and really finding something unique about them. And then it creates that message with that hook for each and every client and for each and every prospect at scale. So you can do thousands of messages, both LinkedIn and email, very, very quickly without having to spend hours and hours doing the data and analytics as well as doing the personalization.

John Gauntt [00:04:29] So when your customers come to you, it sounds like their first source of data is their their LinkedIn presence. What would be some other primary sources of data that you’re drawing from?

Shira Simmonds [00:04:41] So we’re actually initially drawing from our previous history as a company. We’ve sent over 25 million emails. So we’re able to look at historically all of the emails that we sent. What was the best subject line for each persona? What was the best call to action? Was it a soft call to action? Like, hey, this of interest? Or was that a hard call to action? Like, how’s Monday at five for a call? Right. So we’re first drawing on all of the data points that we have built over the last 13 years for all of the clients that we’ve serviced and messages that we’ve made. Then we look at LinkedIn and we’re able to scrape each persona’s LinkedIn profile, and that’s our primary source that we use because that’s really the biggest business social footprint for each individual that we can find it. We can also integrate Instagram and YouTube, but we find that from a business perspective, it’s usually best to focus on LinkedIn.

John Gauntt [00:05:39] And then for your customers by industry. I know that you’re that you’re focused on B2B. Are there particular industries or sectors where you’ve got a heavier concentration of customers?

Shira Simmonds [00:05:51] Yeah, I would say, first of all, we like you, like you said, we’re B2B agnostic, but there’s definitely, I would say, certain industries that work really well. For example, any company that’s targeting e-commerce or Shopify works really well for us. Any advertising or marketing, any SaaS or technology companies work really, really well. Events work really well as well. I can I can. To be honest, it’s easier for me to tell you the ones that don’t work as well because most do. But there’s a few, I would say, personas that are not very interactive, I would say.

John Gauntt [00:06:28] What specifically drew you into this space? You’ve got several decades of experience with SSC Digital and now with Smart Reach AI.

Shira Simmonds [00:06:37] Yeah, I mean, honestly, when I first started, this is actually my second company and when I first started SSC, I really thought I would be just more of a consultant. You know, after you have your first exit, you want to just relax and take some time. But that did not happen. I had a lot of companies come to me and say, Hey, can you help us find, you know, potential partners, potential customers? And it kind of just blossomed into expanding the team and growing and growing from there. But what really, I would say inspired me to build Smart Reach AI was the fact that the landscape was changing. You know, it used to be that you can send an email and book a call, I would say, in a much easier fashion than you can now. And same with LinkedIn and now with AI, anybody can write a message and easily send out tons of emails and everyone’s inbox is getting inundated right now as well as their LinkedIn, you know, inbox. And in addition, you know, Gmail came out with new filters and new rules around what is going to be marked as spam and what is going to be delivered. And so I realized that I really had to change up the game if I was going to get my emails through to that deliverability and really increase the deliverability and make sure that people actually were reading the emails. So the concept of having a hyper personalized email where it’s not just the first sentence, that’s personalized. The entire email from beginning to end is completely hyper personalized. And that way it also doesn’t look like a bulk email sender that gets flagged by Gmail and Outlook, etc.. So that was one of the big drivers for me was coming up with something that was just going to get through. And then the second part honestly, was just my ultimate goal. And our goal as a company is to just book good calls for our clients so that they can grow. That’s the ultimate goal. I want to help companies grow by bringing them new business and not just calls, but good calls, calls that are actually going to convert to sales. And so that’s always been my objective. And how can I leverage this amazing technology and go deeper than what humans can do in order to accomplish that goal?

John Gauntt [00:08:44] Let’s actually go over outbound email. The 100 or the 101 level. What are the primary areas and tasks for making outbound email? Cold Call email a legitimate contributor to your B2B success?

Shira Simmonds [00:08:58] Absolutely. So I mean, there’s many components that go into a successful email. I think I touched upon one, which could be a whole show in and of itself is email deliverability. The first step is you need to really make sure that you’re not using your main company domain that you’re setting up and warming up your domains. You have all the right settings set up for those domains and that they’re healthy and they have a good score. That’s the first thing. The second thing is really your list. Okay. Where are you getting your leads from? Your data from? One of the things that we really like to focus on is what we call smart signals. And that is not just building a list of companies that meet our ICP, which I can look on Sales Navigator very easily and look for anyone that has this revenue, this employee accounts, this title, these industries, these countries, right. But to go a little bit deeper than that, because just because they’re my ideal customer profile and they meet the criteria, it doesn’t mean they’re interested in what I have to offer. It doesn’t mean they really have this problem that I can solve. So how can I find people that actually are showing some intent where they may have a problem? So that could be they’re following your competitors, right? So if they’re following your competitors on link with LinkedIn, the likelihood is that they’re going to be a potential lead for you because they’re following them for a reason. They may have commented on somebody’s post that was about something that you’re offering, right? So it’s about finding these signals and finding people that are actually searching for you and then have an amazing email copy to complement that with personalization with the right hook. The right length, the right tone. So those are the three pillars that are required for success in cold email marketing.

John Gauntt [00:10:49] Aside from kind of the obvious, what is a main differentiator between trying to do this for B2B versus someone who says, you know, hey, I want to find consumers for my widget, You know, what’s what? What are some of the B2B differentiating factors?

Shira Simmonds [00:11:08] Yeah. I mean, I think with B2B, the differentiating factors are it’s not an ad. It’s a little bit different, whereas B2C, you’re more focused on, okay, I would love to run these like Facebook ads or Instagram ads because they’re visuals and there’s there’s a whole art. And that’s definitely not my area of expertise. B2B is you’re finding these companies based on their intent. Did the company just raise funding? Right. Are they hiring new employees? Right. So it’s really more focused on the events of the companies and what the company’s needs are versus what the consumers needs are.

John Gauntt [00:11:44] When we’re looking at the compelling reasons for actually bringing AI into this, you know, efficiency is given, you know, anything AI can make efficient. But you know, what makes you efficient also makes your competitor efficient. You mentioned earlier about diving deeper analytics. Can you dive deeper into precisely what’s your what’s your meaning that AI is helping you get analytics that either A you always knew you wanted or B you’re uncovering and going on? That’s interesting. Yeah.

Shira Simmonds [00:12:15] For sure. Like it’s really interesting for us because we spent a lot of time figuring out how to leverage the AI with the data science, like what are we really going to be looking at? And we uncovered a lot of really, really interesting things like, for example, the open rate, which is something that we were always looking at to optimize. We were always looking at, you know, what is the open rate through the funnel, right? Then the reply rate. But the open rate had much less significance than the unsubscribed rates, right? And that’s not something that we really ever looked at in depth, I would say. And through these analytics we were able to uncover, we actually the unsubscribed rate is showing that this message is clearly not for the subject, right? Is not matching where the open rate could be like a fake open or could be that they open the subject line and then they were happy and it wasn’t a real good indication of booked calls. So we are use we do very deep to really uncover through the 25 million emails and hundreds of thousands of LinkedIn messages that we sent to really look at what are the factors and how do we weight them, how are we going to weight and unsubscribe? Is it a negative one like we gave each one to waits based on the success and based on what really made sense in terms of what was going to book the calls. So again, it all goes back to for us, what is booking the calls and how can we find the trends of what’s booking the calls for a country per persona, per industry? And the insights that we uncovered were really interesting. Like, for example, certain interests in certain industries in the UK really prefer a softer call to action. They don’t like that aggressive, you know, Hey, can you talk to me at 10:00 on Monday? Right. These are kind of obvious, but we have a lot of insights that we uncover per persona, per industry, per employee size as well. They were like, this is super interesting. Like, I would have never thought that the manufacturing industry would really respond to this kind of subject line and tone. But really, based on our data, we could see that they do. So there is a lot of deep diving that we did to uncover how do we group these together, how do we weight the different signals? And for us the signals are the opens, the replies, the positive replies. Right? What are people saying at the end? And using semantic as well to like real semantics to understand Is this a positive? Because many of the tools that we use to send emails like are not really good at that. So let’s say that this was an interested reply and really it was like stop bothering me and it was a negative. So really like deep diving into the interest of replies is real and why are they interested? Why are they saying yes? I was just looking for this or my boss just told me to start exploring this. Or why are they saying no? You know what, we don’t have budget, right? And that helps us kind of form that. Maybe there too, maybe it’s too extensive for them, right? So all of these data points, we we we really dug very deep and the system continuously does that. And I would say also what’s super interesting is that we started doing this and we realized like the economy is changing, the world is changing. And what used to work three years ago doesn’t necessarily mean that it’s going to work now. So the other thing that we did is we built this learning engine as well that will track in real time and tell you real time what is actually converting now, what is giving the best reply, you know, interested reply rate, the best conversion rates now in this moment versus three years ago and it’s constantly learning and optimizing based on that.

John Gauntt [00:15:44] Well, without giving away the secret sauce, I mean, what is your fundamental AI tech stack?

Shira Simmonds [00:15:50] We do use Chat GPT. That is our main AI tool. Right now we are on Azure. We’re Microsoft Stack and we have built our own proprietary technology on top of that. Okay, so all it’s like pages and pages of prompts. And if this, then this and if that, then that. So it was a lot of writing our own code and figuring out what really is the best way to, to manipulate everything. And then we’re also building out which hopefully will be it will be live by this podcast, Smart Signals, which is what I mentioned to earlier, really finding people based on signals that they’re showing, whether they commented on a post, posted something or following a competitor or a lookalike company that looks like one of your customers as an example. So all these different have visited your website, all these different intent signals that we’re building right now that will also be couples in with with Smart Reach.

John Gauntt [00:16:51] Let’s unpack this learning process with AI mean, we’ve been talking about all these messages you’re sending the human beings. Well, you got to send prompts and messages to chat group as well. So walk me through when you first start said, okay, we’re going to go look, we’re going to work this strategy and you start prompting and you’re getting back results as you’re developing kind of the equivalent of your style guide. How are you training the people in your company to work with the AI to get the results that you’re looking for?

Shira Simmonds [00:17:23] So interesting you say that I actually hired a separate team that was working and special AI engineers because we came through a service based company and we built a tech company. And so I actually hired a whole new department that was focused on and experts in in AI engineering and in Azure and in all the different areas that we’re that we’re building. And then I train my team on how to leverage the tool and how to respond, because we also have a team that’s responding and booking the meetings. So that was a lot of training on, okay, if they actually, you know, read the email and now how do you use AI to respond and really personalize that email? So we train them on how to do that. And that was about a few months process, but they caught on very, very quickly. And I would say also now we’re going through a process where we’re also leveraging AI for our data and we just revamped our whole data team and they’re going through a whole training process right now on how to leverage this AI. So there is training definitely, but my team are smart cookies. They’re picking up on it pretty quickly.

John Gauntt [00:18:34] Yeah, I mean, that’s one of the things I still I still run across with interviewing people is that sometimes you get people who take the approach of AI. It’s an answer machine. I pull the crank, I get the answer I want. Well, you better have a simple question, but it seems that it’s not so much that cost and investment disappears. It shifts. So would you say in in your investment profile of how you’ve been building your company, you’re shifting more towards training a smaller team at a higher level?

Shira Simmonds [00:19:11] Yes and no. I would say we’re shifting definitely towards training a smaller team, but we’re shifting the budget towards engineers and developers, right, to do more of the automation and to build it out so that it’s scalable. And then we’re definitely training a smaller team. But the larger team is going to be the front end developer that we have, the UX, UI, the back end developer, the developer. So that’s kind of a whole new area for the company. So I would say budget has shifted there and we need less human interaction. Now on the data side, for example, because a lot of that is just being automated and built. But yes, they definitely need the proper training. And I would say also the transition period is super important. So not just to say, hey, this is launching tomorrow, this is what you need to do. When we do the transition, which we’ve done several iterations of this and we’re actually going through one right now. Every morning our head engineer is sitting with the data team and going through the process with them and checking that everything was working properly. And we’re not launching it till we go through two weeks of doing that every single morning so that they really understand it. So he can find and see are there any problems with this automation that it’s not working properly or we’re missing something or they’re missing something and they need further training. So it is a process where you need to go through that together between your people and your engineers and make sure that they can communicate to each other as well. Because they talk engineer. They don’t talk into your group, right. So it’s just making sure that they can communicate and really express the problems and that the engineers can really understand the manual tasks that they used to be doing to make their lives easier. And the way that I presented to the team is like, this is to make your job easier. We don’t need as many of you, but you’re going to be managing a lot more now because we can scale this, but you need to share with us where the challenges are so that we can make your lives easier and automated even more.

John Gauntt [00:21:16] So now let’s flip over to the customer side, because you can’t have just a sophisticated supply side without a sophisticated demand side. So let’s look on the demand side. How have the conversations with your customers evolved since you first introduced this capability and now you are wanting to scale this capability?

Shira Simmonds [00:21:38] Yeah, I mean, it’s really interesting. I’d say that our customers went through a panic stage because the emails that we were basically their growth, you know, we were their growth partner and all of a sudden emails, we’re not converting as well. Right? And all of a sudden everyone’s coming in saying AI, AI. And they got really confused and really overwhelmed. But they’re also booking less calls. And so we had to kind of go through a just the same type of training transition with our clients and show them, hey, we’re building this right now from the beginning. And the advantage I think we had and building Smart Reach that we had SSC. So we had a lot of loyal clients that really believe in us and trusted us. And so we were able to say, we’d love for you guys to, you know, at no cost, just run with this, give us your feedback, and we’re able to do a ton of beta testing on our own internal clients first and teach them what we’re doing, how we’re doing it. And the truth is they don’t really care. At the end of the day, they’re like, great, you’re booking us calls and then they’re looking at the emails and like, Yeah, people are commenting about what a great personalized email we sent. And then they started realizing, wait, there’s something here, right? So that that’s kind of the evolution of the client side.

John Gauntt [00:22:51] Well, fundamentally, I mean, even if you change your your tech stack and your whole organization as a customer, I’m not buying your process. I’m buying my outcome. You know, when we’re talking not only about ROI, but also in email marketing and particular ethics and transparency and how you’re doing, this is equally important as what you’re doing because as you can appreciate, there can be a lot of potential blowback. And everybody’s run that gamut from, Wow, that’s interesting all the way to the extreme annoyance. Why are you sending me this? So what are the ways that you’re baking into your processes, the, you know, the the ethical dimension that will that will help you actually do better business?

Shira Simmonds [00:23:38] Well, first of all, we are fully GDPR compliant. One of the resources that we hired was a data processing officer that ensures that we are fully compliant and following all the regulations. I think, to be honest with you, the most important thing is that there is some type of intent that you’re not just sending an email to someone that has nothing to do with what you’re offering. My goal here in this email is to help you to make you reach, you know, to help you reach your goals. Whatever email I’m sending, whatever tool or service I’m promoting for my clients. It’s always to help them either increase their ROI, grow as a company, whatever it is, the service or product is. And it to take that mindset is before I send this email, is this person in need? Is this a problem that they’re having that we can solve? And that’s how we look at it. And if you if you run your advertising and your marketing with that in mind, you’re going to really have, first of all, a higher reply rate, but you’re also going to have really more of an ethical type of approach because you’re really only sending messages to people who you feel have a problem that you can help. And there’s really intent there. And if and also obviously following all the regulations about opting out and unsubscribing and not sending them any further emails and removing them, there’s a lot of processes as the processor that we have to follow in terms of the compliance. So we we follow all of that.

John Gauntt [00:25:04] Right now. We’ve been talking about email as just as natural as the air and breathing. And yet if you go back in your time machine, the idea of think of where how we’re pulling these two things together, electronic mail as as this AI revolution gains scale, I mean, how long do you think we’ll be looking at email as a particular form of communication and even a particular technology? I mean, what kind of communication do you see evolving out of new AI capabilities?

Shira Simmonds [00:25:37] I don’t even know in a decade if there will be emails anymore or if the emails will take the same format. I feel like we’re going to go into more of an immersive interactive environments, and we have several clients that are also in the virtual reality space as well. So really to be able to go in and immerse and interact with someone and feel as if you’re in front of them, I feel like that’s where it’s going to be evolving. I also think that AI is really going to take over a lot of the, you know, I would say receptionist roles where they can I actually have another client that’s building this out as well, where they can answer phone calls, answer questions, direct them to the right person. So I think that email is going to shift into more of like an immersive interactive experience. And I don’t know what form or shift that will take, but I definitely see it evolving.

John Gauntt [00:26:30] So looking into your crystal ball, crystal ball, let’s say the next year or two, what are some things we should be looking for in the news cycle that are indicating that the email lead generation industry is integrating AI and in a successful way or not?

Shira Simmonds [00:26:49] No, I definitely think you’re going to see a lot of buzz around hyper personalization. That’s going to be a big one is how do you really personalize it in a way that’s going to get people to read it and cut through the clutter? I think also that there’s going to be companies that are going to either merge together or partner together that are going to stand together in terms of offering a full service type of solution, whether it’s through LinkedIn, you know, email, website, visitors chat bots on your website, who’s Googling and searching for you. So all of those components are going to be coming together to create like one amazing solution for you to to do outreach. I do think it’s going to get more expensive over time because these tools are quite pricey. But I do think also that, you know, now is the hype. So the cost is there. And I think as Chat GPT costs go down and other tools, other A.I. tools, costs go down, the pricing also will be more affordable for small and medium sized businesses.

John Gauntt [00:27:50] What is the best way for people to find Smart Reach AI and find you?

Shira Simmonds [00:27:55] Sure. So it’s smartreachai.com and we actually do offer a free trial. So whoever is interested can can log into smartreachai.com. And within that we also have a chat so you guys can chat with my team. And happy to you can ask for me Shira and they’ll connect you to me or you can speak to my amazing team as well. I’m on LinkedIn. Yes, Shira Simmonds And my LinkedIn profile is Shira Simmonds I have a very strong presence on LinkedIn. I talk to a lot of people on LinkedIn, so feel free to connect to me.

John Gauntt [00:28:30] So Shira Simmons, founder of Smart Reach AI and the CEO of SSC Digital, Thank you so much for speaking with the Culture and Code podcast.

Shira Simmonds [00:28:38] My pleasure. Thank you so much.

John Gauntt [00:28:43] You’ve been listening to the Culture and Code podcast, Creativity and Artificial Intelligence. You can find us on all major podcasting platforms and our website culture and code.io. That’s one word culture and code.io. To support this podcast, subscribe to our email newsletter for a weekly round up of analysis news plus AI training and growth opportunities for creative professionals. It’s all there at Culture and Code .io. Culture and Code is a creative studio and professional education provider that’s part of the Augmented City LLC. I’m John Gauntt. Inviting you to the next episode of the Culture and Code Podcast. Thanks for listening.