Arlen: Welcome to the eCommerce marketing podcast, everyone, I am your host, Arlen Robinson, and today we have a very special guest, Maddie Martin, who is the head of growth and education at, which provides integrated phone and web chat services for solo and small-firm attorneys, including their virtual receptionist & intake service, live website chat, and Keypad cloud phone system. She has spent the last decade growing tech startups from New York to California, and has expertise in digital marketing, small business communications, lead conversion, email marketing, SEO, and event marketing.

 Maddy: Thanks for having me.

Arlen: I’m super excited to talk to you because today we’re going to be diving into some areas that we may have banished around. A little bit with on some other podcasts, but not really in depth. But we’re going to be talking about live chat, chat bots, and lead conversions, and you know how you optimize all these things to drive sales and pull customers in.

So really excited because I know that you’re. Your bread and butter and the things that you’re doing, and you know a lot about that. But before we get into that subject of today, if you can let us know a little bit about, a little bit more about your background and specifically how you got into what you’re doing today.

Maddy: Sure. Well, I have a pretty varied background. I actually graduated with an economics degree. Then I moved . Along the Eastern seaboard. Uh, and I was working remotely from home for a company called food 52 where I ran their, their audience development. And basically what that meant at the time when you could still sort of email the food editor at Yahoo and get on the Yahoo homepage with a good recipe events, a lot of partnerships and relationships.

And we did a lot with . Affiliate marketing and you know, the sheriff sales of the world and things like that. Like back then when we were building this program, it was a lot of food bloggers. You know, Gorman and Bon Appetit were gone at the time and they were sort of going by the wayside when all the food bloggers and the home cooks were getting the attention that they deserved.

And I sort of got interested in this online community and this like sort of micro community. Engagement that was happening with practically strangers who are engaging on this online food community, which was food 52 and what was interesting was working to elevate their recipes and giving them a voice that they had never had at such a level before.

And sort of creating actually real. Value out of those recipes. They would be published in a cookbook. You know, these people would get book deals themselves sometimes because of the recognition through the platform. And then from there, I actually moved to California. I started working for another company, which is your mechanic, and they sent.

Mechanics, your home or office to fix your car. So yet another like really core life service. We went from food to automobiles and everyone needs a car to get to work. Maybe not so much anymore, but that was the case, right? And run and growth for them. And we had a very tech enabled business as well.

Elevating again, these like sort of. Smaller players in the market. They weren’t working for the dealerships. They were working for themselves and fixing cars, but needed the warranty, the backing, the logistical capabilities of a bigger business. They wanted to build up their reviews. They didn’t have their own, you know, review site or their own Yelp page.

And then from there. Move to where we are now. It’s myth AI, which is again, elevating the smaller businesses, giving them the tools they need to succeed and taking those things off their plate so that they can do just like the home cook, just like the car mechanic, the lawyers, financial advisors, professional services providers of the world, they can focus on their core competency.

And that’s really what inspires me as a marketing professional to bring attention and support. To the small business owners who are really the backbone of the economy. That’s 

Arlen: awesome. And I appreciate you sharing that. It sounds like you definitely have a diverse kind of set of, uh. Experiences that you’ve, you know, you’ve been associated with a number of different companies running growth.

And one of the things I kind of laughed about as you mentioned, you know, getting on the homepage of Yahoo by just emailing the editor a recipe. Those were real doors. Yeah. That is real. Those were the good old days, man. 

Maddy: Yeah. Those were the good old days, you know, and you never know how good it was until you’re out of it.

But everything, and it’s funny, everything is relationship driven. And. I think that we talk about sentiment a lot around even the chat bot topic, so we can get into that today. 

Arlen: Okay. That’s awesome. I don’t think that strategy will work today. I don’t think you should email the editor will get in that home page, unfortunately.

Maddy: Quite short lived thing. 

Arlen: Yeah. Not quite that easy these days, but uh, you know, for, of course, all of our eCommerce businesses and e-commerce marketers that are listening.  kind of want to hear you dive in. What do you think are, you know, there are really many options with regards to getting leads now as far as all of these options from getting leads, from live chat, to chat bots, to leave pages, all of these different things to convert leads into actual paying customers.

How does an eCommerce business determine which particular method or strategy is going to be best for them? 

Maddy: Yeah. So I mean it really, there are a few factors here, right? Like, are you delivering a digital product? Are you delivering a physical good? What information do you need to determine if the person is needing a live staff or a chat bot?

How programmatic can your answers be and how complex is the product that you’re selling or maybe even service that you’re selling versus. What information is also displayed on the page? How robust is your website and can you link to things or do you really need to be able to describe everything within a chat?

For example, if you have an eCommerce business that requires, you know, a log in to access or is behind some sort of wall, then chat may serve a sort of peak through. However, if you have something that, you know, there’s a ton of content in the website and people are using chat. As a search function to sort of navigate and quickly get answers.

Then oftentimes you can leverage chat to, you know, give people the right information or the link to the page where that exists. In addition to using those questions to identify where they are in the buying process, like you’ll know from. The questions that are asked on chat, how much they already know about your product, how serious they are, if they’re, you know, new or existing client for example.

But some of the interesting things are to really programmatically build the chat so that you have as much control over the conversation as possible. Like the open ended. Chats where there’s just only free text fields are really hard to predict and program. Whereas if you have close ended questions like, hi, thanks for visiting myth AI, are you a returning client or a new business looking for services?

Right? And that could apply to stores selling shoes, right? Are you an existing customer or are you looking for shoes today? And then. They have to pick one of those options and you go there into the more targeted conversation. 

Arlen: That’s awesome. And it really almost seems like these days, it’s from the fact that people are so comfortable chatting because you know, everyone has a text message, but most people of course have text messaging.

People are familiar with Skype and it’s just become something that they’re comfortable with. Do you think these chat. Tools and bots and things that are they becoming a replacement for people picking up the phone and trying to reach someone? What do you see as far as kind of stats are concerned with that?

Or is it a replacement? 

Maddy: So what we’re seeing is that people of all ages are going to the website first. We know that already, and they, if they can communicate by chat. Or even by text, clicking the phone number instead of calling, right? Typing in the chat when you visit the website, that is going to reduce your call volume, which can be very cost effective and also get the answers that are needed.

That just can’t be found because someone can’t navigate your website, but the preference is visit the website first and then if you can get that chat. What we typically see is for every four calls you can expect one net new lead from chat, and then you can also for every, I think. Nine web form fills, like if you have a contact us form about five chats.

So what we’re seeing is that it’s increasing the speed of communication because there’s not then a ticket request or like an email to get back to from that form fill, the phone doesn’t ring and we’re seeing a preference for chat and we’re also seeing that that has a cost effective benefit. Now, one thing I’ll say is that if you use a solution like Smith AI, then you’ve got the omnichannel approach already.

So the text messages that come in, the Facebook messages that come in are all coming into a single stream channel for our agents or the chat bot to respond to. Right now. Our chat is either, just so that we sort of pull back for a second on, there are different forms of chat, right? There’s the chat bot.

That’s AI only. There’s the live staffed version, and that can be either staffed and outsourced, which is we’re doing. Or it can be self-serve, which means like someone on your team is using chat software to respond themselves internally. And what we find is that that is actually sometimes. The most challenging approach because it’s interrupting your team on their computers during the day, pinging them round Robin maybe, but what I typically see is it interrupts the person with the lowest skillset and they get them many interruptions to the point where it almost becomes like a full time job for some business.

Arlen: Right. That makes a lot of sense, and I can definitely see that. I’m familiar with that on internally, on our end here with it at OSI fully software, we do live chat, not only in our front end site, but in our, in our backend, and I, I see different waves in the . Chat requests that we get. You know, there’s some wait days or weeks where we have a high influx of them.

And like you said, it definitely does interrupt our support staff that does have to demand these and it can become a full time job. But then there’s other times words, there’s a slow point, you know, just as any businesses, website traffic is gonna have its fluctuations. So I can definitely see how that.

Power that can be very demanding. 

Maddy: It can be risky. And the thing is, so with chat, the important thing is that if you put it up, it sort of has to be interactive. That’s my like one warning is that if you have chat already, these are sort of too, like don’t do this warnings. One is like if you have chat and you’re staffing it.

You have to have the backup plan for after hours when the staff goes home, right? So if you don’t have the 24 seven live chat and you’re doing it, there’s, it’s not so great to have just leave your message. It’s better to at least put a bot in place so that basic questions can be answered. And secondarily is the second point.

Make sure that anyone who engages with the chat, whether it’s live staffed, or whether it’s AI. That you, you enforce capturing name, email, and optionally phone number. Before a chat begins, because what we know is that if someone’s on their phone or if someone is texting, for example, it’s really important that you capture that information so that, let’s say you’re on a website and you lose wifi, and then the person really wanting to stay connected to you, but you lost them.

Well, how do you get back in touch. Being on a website doesn’t give you the call back number the way that a phone or text does. Right, right. 

Arlen: Yeah. I’m glad you mentioned that cause I was just kind of brings me to my next point. And I think the reason why these tools, the chat tools, the live chat and the chat box and we consume, have become so popular is because usually these days when people are on.

Line. They’re going from site to site. Maybe they’re researching a product or service. They’ve got multiple things going on. Everyone is multitasking these days. They probably got like five or 10 different browser tabs open. They’re flipping back and forth at the same time. Maybe they’re. Yeah, maybe they have a day job and they’re also trying to do that 

Maddy: they shouldn’t be on or whatever.


Arlen: Exactly. And so, you know, it wouldn’t be convenient for them to actually pick up the phone. And so that’s why the chat things are in place. So I think, yeah, you’re right. It’s very important that you capture that information. 

Maddy: Let me tell you something else. Our lens, so this is just to jump in on that one point in particular.

Like you know, it’s important that you capture that info, but also you touch on something that leads me to another point, which is just like being discreet. The tech space, communication versus phone is super important. If you’re in any commerce business, that may be. And intimate product or something like really personal or something and you’re getting a gift for someone else.

You don’t want to overhear it for some reason, or you’re buying something that is just feeling personal, private, sensitive for whatever reason, right? It’s a really nice thing is that there’s no phone call to overhear. There’s no need to step away from your desk. The chat allows you to actually engage with a business from the end user’s perspective, from the consumer perspective, to engage with the business without.

Voicing whatever it is that you want to buy or discuss. 

Arlen: Right. I can definitely see how that’s applicable for those types of businesses that are, you know, have those discreet type products where somebody is not gonna to call. You know, where they are if they are in a public place or, you know, even if they’re at home, they’re, you know, they’re not, they may not want to voice that out loud.

That totally makes sense. Now, of course, these chat tools, the live chats, the chat box, and at the end of the day they all kind of fall into the category of helping convert leads are becoming part of the whole lead funnel. What do you think are some best practices for the actual lead intake and lead conversions.

Maddy: So I think that there needs to be oftentimes a multichannel approach to determine how the lead wants to engage. And there’s a lot of sensitivity here with business, but what we know is that yes, landing pages can be very effective. We know that this sort of organic looking or content. Driven native approach to user acquisition.

Customer acquisition is, is quite effective, right? Like get someone to make a download or engage or find something funny or share an organic sort of post or something helpful already. And then how does that relate to the product? Great. And there’s social proof, there’s testimonials, there’s case studies, right?

There’s how did this product change my life sort of thing. Stories. The storytelling often is what can bring them in. If it’s not a referral or affiliate or just you know, ad that they’ve been displaying and seeing for a while because they’ve abandoned their cart. That’s a different story. Now they come to your site.

There are a lot of really interesting tools that you can use. To make sure that the follow up is really well targeted. So yeah, you can have a chat and you’ll see the entire chat transcript and that can help you follow up. You’ll know what page they were on. There’s a lot of metadata that you can see within a chat, but there are layered on services.

You can also add. I recently found out about a company called lead forensics, and they actually are able to bring in a lot of metadata on who that visitor is and a lot about their persona and who they work for, the business where they’re based. Like maybe, maybe there is a B2B play there. And you want that data that they’re not likely to share with you during that conversation or when they do click into and buy something in the cart.

So that can be put just the same way as the conversation, as a log into your Salesforce, into your HubSpot. So you’re capturing that information passively, and that informs your approach for them to follow up. Because what happens is. Some of them will have a chat. They say, Oh, can you answer this question for me?

Sure. Does that help you? Are you ready to buy? You know, that’s sort of like the next step, and then that person may say yes or no. Well, if they say yes, then you facilitate it. If they say no, then you’ve at least captured that name and email, right? Maybe even the phone number. And you know, too, in your system, whether it’s, you know, HubSpot to then start that follow up, well, what does the followup look like?

Because traditionally it was email marketing and merchandising, right? Maybe it was a phone call, depending on if your cost of product is actually warranting the cost of making that phone call right. Higher value products may warrant that lower cost products may not, how time-sensitive is it, et cetera.

Now what we’re seeing is when those conversations end, if the buy didn’t happen, then you can send maybe an SMS follow up. Here’s the link to buy, here’s a little bit of a guide on the product to help understand how it will impact your life or whatever the case is, and those things can indicate. Where they respond.

If you send out an email and then later an SMS and then make a phone call. And you’re maybe remarketing to them on Facebook or wherever. Then you’ll see over time, does that text message get responded to? Is the email opened? Where do they end up converting from? And that will tell you a lot about your multichannel funnel, right?

Because these people are not just sitting in a computer and that’s their only way to access your brand. But what you get is the preference. Based on what they do next. So if you send them those things and then they text you back, or they convert from the text, then you sort of know, okay, well that worked.

Who did it work for? Who was that customer? Do they share characteristics of other customers who also seem to respond to SMS? 

Arlen: That’s some really powerful stuff. And we’re really at a, at an age now where all of that data is available. Like you said, you mentioned the tool, the lead forensics, and I know there’s a lot of other tools that are tied into some of these chat products that are, that will give your live chat systems in your life set agents.

The information up front where it can do some querying based on, you know, the location of that visitor, the browser that they’re on, if they’re on a mobile device, all those types of things can be pulled. Anything, you know, they can even scrub other databases to even look them up via social media, see what their social media accounts are.

And so yeah, it is amazing how all of that can, then you can take that initial upfront information and then based on what the person does from there, then further. Categorize them or segment them in your other marketing approaches. So yeah, that’s some powerful stuff that I think all businesses should definitely take advantage of because it is all out there and there’s a number of tools for doing that.

Now, you mentioned the lead forensics and some other tools, and the main thing of course is, is the follow up. A lot of these. Chat tools also are used to help grow, you know, email lists. That’s kind of one of the things that you can kind of get people into, you know, an email funnel where you’re maybe educating them a little bit about your particular niche, not necessarily doing a hard sell.

Are there any other particular tools that you’ve worked with that tie well into live chat systems? 

Maddy: So I would say there are a few tools that tie really into the live chat systems. It is imperative that you’ve got your CRM integrated, right? It’s also something that we’ve done, which is to have chat to call.

So if you’re on a chat and the conversation is going to a point where they’re like, Oh, I just need. A live person. Maybe it’s support. I mean, we’re talking a lot about sales and maybe it’s support or maybe it’s like just a little bit more of a handheld sale. It’s really important that you have the call, but then also that that call gets

Pushed into your call system or rings to someone or prompts someone on the team or outsource, can you make a call back to this person? They’re expecting a call because some of the conversations just require a little bit of live help, so, and that, that’s product dependent. So that’s something that’s important.

All the transcripts and conversations in context that are made. Yes, it’s good to get that email drip. And that sort of implies that you’re putting it into a system to drip emails. So when you want to have happen is that the conversation and the contact are added, if it’s a conversation from a repeat contact that that’s logged in their existing record, and then.

Someone is making sure that based on that conversation, they go into the right drip. You know, you don’t want it to be that, Oh, every new chat initiates like a a welcome email. Right. Because that may not be appropriate, but so that these people are properly like funneled. And, and followed up with in the way that it’s appropriate to how, you know your sales funnel goes.

You know, there’s not one sales funnel for everything, but there is an understanding that it often takes more than one touch point to make a sale. 

Arlen: Yeah, that’s definitely so true. Especially these days. Are you going to have to make multiple points of contact usually before somebody makes that, that ultimate decision to purchase and then pull the trigger.

So Maddie, as we prepare to wrap things up, what are some top brands that do a great job with lead conversion, live chat, chat bots, and conversions with these tools that we can all learn from? 

Maddy: So, to be honest, I have been very impressed with. MailChimp, I often as a MailChimp user myself need to get in touch with their chat, and I find that it is extremely effective.

Um, I also have found that very highly reliant on chat brands, like, you know, to be honest, ring central, which is a very complex or can be complex phone system even, you know, Amazon. They are doing incredibly well with chat and they obviously have large teams that can staff that, but if you look at the way that they interact and the way that they seek to deliver an answer and close that ticket, so to speak, that to me is the best experience.

What you don’t want to do is what a lot of. Sort of poor players in the chat industry do, which is chat is just a self development sort of death. And there’s never an answer or real content provided and they just want to get you on the phone. If that is your intended approach, I would really like encourage you to rethink that because for the end user, just because we see both sides being the platform, they don’t prefer to.

Have to wait for that answer. The whole point is they’re looking for steering and guidance and at least some sort of directional approach rather than, Oh, let me get on the phone with, let me schedule a meeting with you so that you can talk to someone about it. That lead blocker approach is often not that welcome, not that well saved.

Arlen: I understand. And I’ve been to those sites before where, you know, you just have a basic question and they’re just. Immediately just trying to get you to call where it just kind of seems like in those cases, the person Manning the chat is just kind of one of their lower, lower level customer service.

People that aren’t that knowledgeable about the product or service, and then their goal is to just try to funnel the customer over to more of a higher level. Support 

Maddy: or they’re being paid by leads, right? So if your company that you’re working for is incentivized to do something that is maybe not aligned with the incentives you want to give to your business growth.

So if you say, Oh, we’re paying this company too. Only get paid if they have a relevant lead and the lead is defined as you got the name, email and phone number, then that’s all they’re going to do and they’re going to pass it off like as soon as they’re done with their job because it’s cheaper for them.

So you have to think about what incentives people are playing with based on what you’re paying for with that model. And then I would also say like if someone is asking you questions, why not answer them? Because you don’t want to schedule a phone call if the person is asking those questions to sort of self screen themselves.

If you give that answer and they say, you know what, that means I don’t need a phone call. Then you’ve saved yourself time and money so it moves you to deliver that answer. 

Arlen: Yeah, for sure. For sure. Yeah. The main thing is it’s definitely less costly to be able to solve that. Problem or answer that question initially right there in the live chat, rather than to, you know, have somebody call type of phone line and then, you know, utilize the time of maybe another higher level person.

So all around, it’s, um, it’s definitely imperative that you try to get the right things in place so that you can answer those questions directly, you know, via the live chat. Well, Maddie, this has been awesome. I’ve definitely learned a lot. And like I said earlier, we’ve . Touched on a variety of things that I don’t think we’ve ever talked about on the podcast before.

So I’m super excited for our listeners to absorb all of this and uh, and definitely take, put these things into action. But what I like to always do is I close things out here, is just to switch gears, just to pick your brain a little bit more and on some other subjects, just so our audience can get to know you a little bit better.

What is one fun fact that you think our audience would be interested to know about you. 

Maddy: I went to culinary school. So I graduated early from Hamilton college, which is in New York state, and I had extra credits from this IB international baccalaureate program. So I got to do that. And I, in January of what would’ve been my senior spring semester, uh, went to culinary school in New York city.

And that was a really enriching experience. 

Arlen: Oh, wow. That’s awesome. Yeah, I know you learned a lot. I do a little cooking and myself and you know, at some point I think I would have loved to take some, well maybe I will still do take some type of cooking classes and 

Maddy: it’s wonderful. And if you ever get the chance, I mean, I’ll tell you, the Institute for culinary education in New York, it’s right near Madison square park.

And I highly recommend it. They do recreational classes with the professional chefs who teach there their career program. 

Arlen: Oh, wow. That’s awesome. Well, I definitely will take note of that for sure. Anybody else listening that’s interested in to kind of dabbling a little bit more in the kitchen? I think that would be a something pretty fun to get into.

Well, uh, you know, like I said, thanks again for joining us today on the eCommerce marketing podcast, Maddie, but before we let you go, if any of the listeners out there. We’d like to pick your brain anymore about live chat, chat bots and conversions through those mediums. What is the best way from them to get in contact with you?

Maddy: So you can reach me at Natty, at Smith dot. AI. That’s mad D [email protected], and you can also get a free trial. I’m even for use of our AI chat bot with the code Arlen 100 that’s Arlen one zero zero you’ll get $100 off our live services. So for calls, for real live staff chat, in addition to our 20 call, 20 chat free trial.

We also have a 24 seven AI only chat bot that is completely free and unlimited conversations on your website. So that’s pretty cool. If you’re on the fence, you can visit or email [email protected] and we will help you get started. And, uh, we would be happy to help install that on your website as well.

If that’s a concern of yours, we will make it as easy as we possibly can and just have those conversations come through so you can see what people are, are looking and exploring out on your website. 

Arlen: All right, great. Well, that’s awesome and I appreciate you sharing and I appreciate you offering that discount.

That definitely seems like a good deal. So, uh, yeah, definitely encourage people to take advantage of that. Well. Great. Well, um, thank you again, Maddie, for joining us today and sharing your knowledge with us. We really appreciate it. And, uh, we wish everyone well in their quest for, you know, getting these leads through live chat components.

Maddy: Wonderful. Thanks so much for having me. 

Podcast Guest Info

Maddy Martin
Head of growth and education at