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In this episode, we sit down with Brian Malkerson, also known as Malky, the Chief Revenue Officer at Attentive, the SMS marketing platform revolutionizing how brands connect with customers. Brian has led Attentive's revenue team through massive growth, scaling to over 8,000 brands and powering billions of messages annually.
Join us as we dive into Brian's journey from being the first salesperson at Attentive to becoming the CRO. We explore the intricacies of product-led growth, building high-performing revenue teams, and why Brian believes SMS is the future of e-commerce.
Key Topics Discussed:
- The challenges and strategies of transitioning to a multi-product company
- The importance of focusing on a specific vertical for initial growth
- Effective sales cycles and the importance of understanding customer pain points
- The role of discovery in a multi-product sales approach
- The impact of incentivizing sales teams and the debate on separate teams for different products
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Brian: When you grow as fast as we did and add a number of people and a lot of people just saw a lot of success, getting the people to shift and buy in to all these changes that you need to do to successfully do multi-product as an example. And I think you had a number of people who just embraced it and saw, wow, once you really figure this out, you can be way more successful because you now just have a lot of different ways to help drive value for customers. And then some people are just like, no, like they got really comfortable with what they knew. And right, we've got to put more work in kind of getting them to kind of learn and adapt. You go from being the expert in what you do and just really focusing on that to having to kind of evolve a little bit. And that that takes a different skill set.
Andy: Today, I'm talking with Brian Malkerson, also known as Malky, who is a CRO at Attentive, which is the SMS marketing platform that is changing how brands connect with customers. Brian has led Attentive's revenue team through massive growth, scaling to over 8000 brands and powering billions of messages annually. Yes, billions with a B, y'all. What's fascinating about Brian's story is how he's helped take SMS from a nice to have into a must have channel that's driving millions in revenue for companies. Also, he started as the VP of sales at Attentive, really as the first salesperson and grew all the way to the CRO, which is just amazing. So we dive into product-led growth, building high-performing revenue teams, and why he believes SMS is the future of e-commerce. We'll cover a ton of tactical advice that you can apply immediately if you're thinking of starting your own sales team or if you already have a sales team and are looking to scale. I learned a lot from this conversation, and I know you will too. Let's go ahead and dive in. And as usual, go ahead and hit subscribe in your favorite podcasting app, whether that's YouTube, Spotify, or Apple Podcasts, so that you're notified as soon as we drop a new episode. Let's dive in.
Brian: Hey, sorry, I had to download the app and set everything up. I didn't.
Andy: Oh, really? Didn't let you join online, huh?
Brian: Um, you know, I'm doing it on my iPad for some reason, my computer, which I just restarted. It's like just having some, it was having some, some struggles. Um, not like last time when literally wifi and the whole neighborhood went out, but I was like, so I just quickly pivoted to my iPad. So then it had moved on the, uh, the app.
Andy: No worries. Well, um, is everything good for you now? Everything.
Brian: Yeah. Thanks for the flexibility. Sorry for the last minute change. Uh, last time too, by the way.
Andy: Oh no, no, no worries. No worries. Well, you know what I have pulled up here on my computer right now is a Malcherson Island. I don't know if you've ever heard of it.
Brian: Uh, I, I have, I have been, been, been there many times.
Andy: What's the story on Malcherson Island here? Like, has this, is this one of those islands that you just had for like 300 years? Or is this just, yeah, this is part of the pod, right? This is part of the pod. Yeah.
Brian: I don't know. I just jumped right into this. Um, yeah. Uh, so, um, it's been in the extended family for God, probably 80 years. I want to say, um, it's uh i mean one thing to know about minnesota there's 20 000 lakes and so yeah like it's almost everyone goes like a cabin it's just kind of a very minnesota thing and so um you know having lived a long time in other cities and areas which i think that's kind of a I don't know, something people get a kick out of or surprised by. But for us, it was really great just because on my dad's side of the family, he had four siblings. And so they would all have cabins up there and we'd all go up almost like every weekend in the summers. And so it was really just got to know my extended family really well and had a lot of really good memories from that. In fact, my dad almost skipped my college graduation because he didn't want to miss a weekend up there. So it was like a very like… Memories of Going up and in order to get there obviously in the ice had the thought my dad You know wanted to get as many weekends as he could and so Maybe I got a pontoon boat with an oar trying to break through the ice Yeah, it's uh, it was a you know a big part of kind of a family life growing up
Andy: install it. Yeah. What's the, is there like a, you know, to get on the island, you guys got like a password and you have to have like the Malcherson Island or, you know, Malcherson last name, or how's the exclusivity to get on this island there?
Brian: Yeah, definitely no passwords involved. Eugene needs some sort of boat or transportation or be a pretty strong swimmer to get there.
Andy: But yeah, that's about it.
Brian: I don't know if there's a lot of people trying to get ashore. I don't want to be there, to be honest. It's two hours in northern Minnesota. But it's beautiful up there, and it's great. And I try and get back there every year, even though I don't live in Minnesota.
Andy: Nice, nice. Well, let's talk about today what I want to get through. So just a little bit of context here. This goes out to like 32,000 people. It's all go to market people that it goes out to. And so I think what would be great to chat with today is like, how do we build a world class sales org, right? Coming from outreach to go to market background. I get lots of questions like this. And so we're bringing on, uh, zeros like yourself and we're, we're asking them, like, how do you think about the market today? Building a sales team, how has changed all that fun stuff. So, um, I know I sent you some kind of questions ahead of time, but man, we're just kind of like loving your thoughts on, on, you know, you joined attentive, remind me you were the first account executive at attentive, right. And you started as a sales rep when you got there.
Brian: I mean, yes and no. So I'd had the pleasure of working with the founders. Well, I actually went to business school with Brian, the CEO and co-founder. So yeah, we've had the two Brian thing for a while. And I had worked with him and Andrew Jones at Tap Commerce, which is the previous startup that Twitter had acquired, and then worked with them at Twitter. And so when they had started Attentive, it was actually originally called Franklin, and it had a little bit of different focus. They decided to pivot to marketing. Yeah, it was originally like shift scheduling software and then a way for like the people to communicate via text with employees. And then, you know, people started, you know, a couple brands asked like, hey, can we actually use this for customers? And so they kind of pivoted and renamed it attentive. Um, and so, you know, Brian, you know, I kept in touch with them and reached out to me. So I joined to come in and be VP of sales. So like to run, um, build a quote unquote sales organization, but obviously we don't have any customers pre-revenue. Um, so I was kind of the acting AE, uh, working with SDRs trying to, you know, sell the first 50 deals, um, and find that product fit, um, working very closely with Brian and the team. Um, And so, yeah, that's where I started, you know, kind of that axiom, you know, do the dishes leader or don't do things you're not supposed to be able to do. Yeah. I feel like I've done a lot of the different roles, uh, at attentive through the seven and a half years that I've been here.
Andy: Yeah. And, and how, okay, this is good. This, you just gave me a softball. Like how did you get into selling the first 50 deals? If you remember, cause I'm sure that was ages ago, right? It was about six, seven, eight years ago. Like what, what, how, what did you do to get the first 50 deals in that time?
Brian: Yeah, I mean, it was a combination of things. You know, we did everything from, you know, because our last company was a mobile app retargeting platform. And so reaching out to people, you know, in the mobile marketing space that we knew, trying to get intros through investors. We had kind of an initial advisory board. We had a handful of SDRs that I was working very closely with that were doing a lot of like outreach and a few different verticals because, you know, at the time we weren't 100% sure which Verticals or sub verticals were going to be the right fit. Um, and yeah, that I was doing outreach myself on LinkedIn, obviously, Brian and the exact, you know, the rest of the leadership team, we were all kind of. Utilizing our network to basically anything we could to get in and. get those initial customers. It's a little bit of a double-edged sword, I found, because I'd have relationships with people and a lot of times they'd be like, sure, we'd love to try something. And they weren't always necessarily the right fit. And so you could end up spending a bunch of time because, and not really getting the idea validated, but more of just the relationship validated. And so, yeah, I remember, there was a ticketing company, SeatGeek, and I'd reached out to them and I had a really good relationship and worked with them a long time. And so they said, sure, we'll give a test, we can pay for it. And we did all of this work, but they didn't want to use it the way that we had kind of built it. And so it was like, they were just gonna send like an email blast out. And we built like this huge, like two months of calendars, because we have this SMS marketing platform, so those people don't know, and did all of this work. And then it was like, It was like 40 users, right? And so, um, you know, that was kind of my first initial learning of like, okay, like it's good to utilize networks and relationships, but you can get a lot of false signals, like false positive signals and, or, um, you know, end up spending a lot of energy and stuff that may not be the right fit for your, um, for the platform and where you're trying to take it. So, um, but look, the other thing I would add is that. Um, early on for us, a lot of times either coming into a very mature existing space. And you're trying to just build that better mousetrap. Maybe you're focusing on a specific. Industry or area, um, and. You know, trying to really kind of focus kind of evolve there, but people already have very set. buying processes, they have budget, all of those stuff is figured out. Or you have like a very new hot space, right, where everyone is looking to do something, but there's tons of startups and stuff rushing into the space, and they're not really quite sure what the right model is and value for the business. That was like chatbots at the time. Everyone was like interested in that. For SMS, it had been kind of around for 20 years, but no one really used it. And It was very much text to join in store, very much analog. And so people had a very negative conception. So no one was really trying to sell it. The biggest issue was no one wanted to buy it. Right. And so that's why a lot of those early things trying to find people, hey, give us a chance. Because we saw early on, even with the first couple like small customers, like we could just tell from a data perspective, wow, this really works. But then the big challenge was like going out there and like getting enough champions and kind of convincing the industry that this is something that people should actually invest in. So very different than obviously where the SMS space is today, where you have almost all econ retail companies, at least in the US, you know, utilizing SMS in some fashion.
Andy: Yeah. And when did you decide, well, when did you decide like, Hey, we're just going to go in on like e-commerce companies. Cause that's pretty much like the niche now. Right? Like you guys, you probably do a couple other things, but like e-commerce is just. Right. The, the main market that you go after, when did you kind of like decide that that was the way that you were going to go? And, and was it scary? Because I think a lot of people get scared about, Ooh, if we go to this one ICP, we're rolling out a bunch of other ones. Right. And, you know, tell us about that and kind of what that moment was like.
Brian: Yeah, well, I'd say first off, e-commerce retail was definitely our big initial focus, and it's still a big core part of our business. We've expanded a lot beyond that. We do entertainment, food and beverage, travel, a bunch of other ones. I mean, we work with NFL, Major League Baseball, Live Nation. So that team has really kind of grown the new verticals a lot over the last few years. But I'd say early on, I think it's very important to focus. I think you know, the more you try and do is the more complexity you're going to add with anything sales process. And I had a mentor, this guy called Eschenbach, who told me that complexity kind of compounds simplicity scales was like a line that I really liked that he used. And so the more verticals, let's say you do, then the more product changes, the more from marketing, the more positioning, the more integrations. And when you're a small company, all of that will slow you down. You're really trying to get that motion and quickly test and learn and experiment. That's what makes the small company so powerful. And why we try and create that within attentive at this stage for new areas that we go into. And so what we did was we had 3 and then we had a number of different sub verticals that we want to look at and test. We tried to briefly map out why we think it might be a good fit or not to the budgeting. Is it going to align with kind of the performance? like element. But, uh, then we gave them all, it was like, one was like on a channel retailers, like one was like e-commerce and then one was media and they each had territory and then throw a bunch of demos. And, uh, I was doing a bunch of calls, you know, and our CEO and some other people would do some as well. I remember one day, I think I did 13 or 14 sales calls and it was like, we only had this one really hot booth. And so it was, you know, you're just going through tons of them at the time. Um, and we just realized, yeah, like the propensity to buy, like the, It was just very challenging, for example, on the media side, because it weren't really necessarily, unless they were driving subscription or something like that, they were making all their money off ad revenue. And because SMS is a more expensive channel than email and other channels, the math didn't really work. Budgets were less. So we learned through doing a bunch of different calls and trial and error of like, okay, e-commerce, retail, Was a good fit for our products, um, as well as kind of the value proposition that we had. And then, so we kind of. Decided after, I think it was like two to four weeks and like looking at the data from our ability to generate meetings and then kind of that sales velocity of like, um, you know, who's actually going to sign up, launch and see success that it made sense to kind of double down on e-commerce retail or the e-commerce retail vertical.
Andy: Yeah. Yeah. And then when you, when you double down on that vertical. Did you, did you like tell people to just stop going after the other verticals? Or was it like, Hey, if they come inbound, great, but like, we're not going to spend our time focusing and going outbound to those people. Like, you know, how did you treat that?
Brian: Yeah, that's a good question. Um, we didn't have a lot of inbound because again, people weren't looking for SMS at the time. So a lot of our marketing focus and Brooker led our marketing team was great. It was just around more of the positioning and a lot of the product marketing and that kind of stuff. And so we didn't have a lot of inbound. Um, and that was part of the challenge. Like you see a lot of companies, particularly like the Shopify eCommerce space, they start almost all partnership and agency driven, but none of those partners wanted to do SMS cause there was no demand or pull for it at the time. Um, so it kind of, necessitated us to be very outbound focused. So we could be very specific and say, look, only reach out to this ICP or these customers and be very targeted. When they did come in, we'd obviously evaluate it. And I think that's where, you know, because you always want to be just in case. Yeah, somebody comes in and maybe you kind of learn and evolve, like looking backwards, it seems obvious what the right path was. But at the time, yeah, you didn't really know. So of course, we were having these conversations, referrals would come in inbound. And, you know, we would try and then put that through a similar process of A lot of people say, oh, this seems great. But then, is there a real signal? Are they willing to go live? Because you have to put our tag on the website. Are you willing to actually put budget towards this? Is there certain goals that if we hit, will you actually commit to paying for this? And so, yeah, we kind of put them through that cycle to try and really see where there was strong signal versus noise, if you will.
Andy: Yeah. And we had Brian Long on the pod around a couple months ago, or maybe more than a couple months ago now. When I asked him about the, you know, from a founder perspective, the, the, the outbound motion. And I go, what's like the one thing that you would recommend people do? And Brian was huge on the gift card play. Right. Brian was like, Hey, He's like the gift card play. He's like, people want to be compensated for their, for their time. Right. And so, um, I know you guys, I think you're still using the gift card play till actually started with AirPods.
Brian: Um, Oh, was it a couple of letters that would give us a hard time, like on social. And then we saw them adopting very soon. I mean, look to me, um, when you start like one, just getting people on the phone, we didn't incentivize tell people like, as far as buying, you just wanted to get in front of them. Because again, getting people to actually get on the phone and listen. And it's like this, that was the original intention, right? We wanted to remove all friction in the, in like the process. Hey, we'll make it super easy. All you have to do is drop this like snippet of JavaScript. And it wasn't even like integrated into like e-commerce platforms at the time. Like you just put it, drop our tag, any site, we'll make it work. We'll help with the copy. We'll copy, we'll do everything. Um, because, again, people didn't want to do this. It was extra work. It was taking risks. It was SMS. So that's where it all started. And I think for me, as we thought about it as it evolved, you know, it's just an acquisition cost, right? Different companies will have different approaches to driving acquisition, whether they're paying lots of brand marketing for things, or a lot of people will buy ads, they'll pay influencers, right? You see a lot of PR space like you know, paying kind of like a lot of influencers and stuff behind the scenes. All that is to me is acquisition cost. At the end of the day, you want to make sure that you're acquiring customers in a way that the math works so that LTV to kind of CAC ratio is something that makes sense and can scale and that you're acquiring the right customers, right? And so we always said, look, this is just to get on the phone for your time. There's never any strings attached and we don't want strings attached because um you know all customers go month to month they can kind of do whatever they want and so if we bring in the wrong customers if they sign up for the wrong reason they're just going to churn out and that was like kind of an important thing um when we almost had every customer in the early days like just doing month to month we would know if they didn't convert or if they did and then dropped off after a month something was wrong so we could It was a very early signal to go back and like, are we positioning this wrong? Are we going to the wrong customer? Do they buy for the wrong reason? So we felt as long as we had the right incentives, and those acquisition costs made sense, we were just going to stick with what worked. And we do a lot of testing and learning, we do like little holdouts. And we'd say, it was funny, I remember at one point, we're like, We wanted to drive a little revenue curve of like, what is the right amount of like, you know, like say gift card or something like that to get people to engage. And it was funny, I remember thinking it wasn't like the largest number. And I get tons of asks like for gift cards and stuff. And sometimes you'll see like $48. And I'm like, all I think about is, I wonder if someone was just testing and they're like, hey, if I do kind of a weird number, it's more likely to get noticed, I'm gonna do it. So for us, it was a lot of quick testing and learning, but all trying to go back to those principles.
Andy: Yeah. Well, what's funny, I started doing that after Brian was like, Hey, yeah, this is the, he's like, this works like a charm. And I would ask some friends, you know, and they, and some people have all their hot, you know, high horse and they're like, no, you don't do the gift cards. That's not real outbound. And they're not pushing the value and blah, blah, blah, blah, blah. And then, and then you go and you ask, well, how would it, how much are you paying for a meeting right now with your cold outbound ads? And they're like 400 and something bucks. And you're like, well, what if I could do it for a hundred?
Brian: Yeah, I mean, again, that's why and look, I think there is. I mean, I remember I was playing tennis with like a friend a few years ago and he's like, by the way, I reached out and with AirPods and like, I was like, wow, maybe we really have scaled this quite a bit if I have friends randomly telling me to speak out. And then I've had some cases where you'd have people multiple times in a year taking meetings. And I do think there is a fair feedback and a fair like, For us, once we kind of got that value proposition and that we just want to focus on customers having great experiences to create that flywheel. So they would basically be our advocates. Then it was so much about just getting out there, getting in front of people, making it really easy. I think that value selling component. it's important to make sure you go back and kind of reinforce that. Otherwise, I do think, you know, it can be kind of too transactional. Otherwise, if you do too much of this as it scales up, and those are some areas that we've had to dial back on and kind of make some adjustments. So I won't say like, yeah, you know, you just offer a gift card and then a free trial and it's kind of off you go. And so, yeah, you know, you have to kind of evolve as you go, like with, you know, with any journey for a startup.
Andy: Yeah. Yeah. And, and so you've seen from what zero to, I don't know if you can say the number now, hundreds of millions of dollars in revenue, let's just say, right. And so with that, how, how do you think about expanding a sales team? Right. And this is a question that I get a lot from, you know, in different stages call for different maybe motions, but. Let's talk about from the zero to one, one to a hundred, hundred plus, how have you thought about expanding the sales team from there? Because this is a common question that I get.
Brian: Yeah. I mean, look, I think the process, the zero to one, I assume you mean like ARR.
Andy: Yeah, exactly. Yeah.
Brian: It's all about finding products market fit and in the zero to one stage, whether it's a CEO founder doing it or like a head of sales acting as like an AE for us, it was both. Brian Long, our CEO came from a sales background and was great at that. So I learned a lot from him and he did like a ton on that front. But that's, I think, really your job. You need to figure out what does that process look like? Where does that product market fit? What's that ICP? What's that motion? And look, I think bringing on SDRs, whatever you can do to be efficient in doing that makes sense. But I think a lot of times people make the mistake, they start trying to hire a bunch of reps and like that without really knowing that. And then I think that can just lead to really bad outcomes, right? Frustration, because people aren't ramping up and then you're trying to like focus and think of that. Like, my view is like, you need to figure that out. Once you figure that out, then yeah, then it's just like finding the right and, you know, and that's through just like relentless experimentation and pivoting until you identify kind of that product market fit and process. And then from there, it is finding what are the right kind of early reps. Right? Who are the ones that, and sometimes it could be, maybe if you have SDRs at that point and they've got enough experience, depending if you're selling more down market or up market. And so I think there's a number of different factors, but for me, the nature of the rep's really important. I think sometimes, you know, people either make the mistake of like, oh, they just have to be in that industry or space, or they want to pull them from some company like a, like Google or Salesforce. And you're just like, That is, and there's so many talented people at those companies. And so I get it. Um, but the challenges and what makes those people successful and or happy on their role is so different than at the early stage. And so to me, we look at like coachability, adaptability, like, are they just like tenacious, right? Like, because they are, regardless of you trying to figure out that part of my initial process, it is going to change a ton. Right. And you need people. who are excited to help build the plane and want a lot of that greenfield and stuff opportunity. And finding those people, whether it's a combination of internal and external, I think is really important. And yeah, so like initially it's going in and then depending on your market size, hopefully you have a big enough market where you can kind of hire and scale like an initial team. But yeah, so then you get a certain number of reps and kind of show that Yes, you can actually scale it. You aren't just selling this because of the founder or yourself or the relationships. You can actually bring people in. You can identify the right people. You can enable them and make them successful. Once you start seeing that, then you kind of get to that next phase or scaling of growth. And I think part of the challenge is Especially people doing for the first time, you almost wait too long. You want to be like overly comfortable, right? That's the other thing you have to worry about. That's why it's tough. Because if you wait till it's so obvious and everyone's in their quota, it takes a while to like hire and then ramp up and get people at capacity, especially if you're adding other lines of management. So you almost have to be comfortable kind of doing that ahead of time. And that's where it can get, you know, obviously a little bit tricky.
Andy: Yeah. And I called it. So, you know, it was early at outreach. So outreach scale from zero to whatever, right. Hundreds of millions.
Brian: And yeah, you guys have an amazing run and we're a happy outreach customer.
Andy: So nice, nice, nice, nice. Yeah. Now I'm building distribute, which I like a few people on your 40 people on your team are using. We'll talk about that later, but, um, well, you know, one thing when we were scaling outreach was, um, I think a mistake that we made, I hope no one over there kills me for this, but like, When we were like scaling our team, you can imagine there was a lot of mistakes that we made as every team does. But I think a few that stick out to me that were interesting were like, we were hiring based on spreadsheet math and not common sense on what was happening, like where people's calendars full. Right. And so like you from a CRO perspective, how do you look at that in expansion of the sales team? Right. Are you, combining the data with the common sense? What are you looking at to do that?
Brian: That's a great call out. I mean, my background, I have a non-traditional early background. I did start out in management consulting and then private equity, worked a little bit in early stage venture. And so I think I almost swung in the early days. The other side, I'm like, I don't want to operate like that. Because to your point, I think you can if you get too much into the spreadsheets you can kind of miss a lot of that but look at the end of the day it's an art and a science and i think you need to in my view know both i kind of start with like at least know the napkin math right um so for a rep like What is the rough territory size? What is the penetration rate for driving pipeline or demos? What is the assumptive close? What do you think the ACV is? So that kind of sales velocity equation, you should generally know that. And then And yeah, to your point, from a capacity or how much meeting, stuff like that. But then also compare, yeah, are they super busy? Then use that to kind of test back and forth. Like, wow, the sales cycle may be a lot more involved than we initially thought. Why is that? Do we expect that to continue or is that because it's just very early and we expect that to improve and get a lot better very quickly? So I think it's both, right? You kind of want to go in, so you kind of know what to look for. And then once you see stuff on the ground, you can kind of make those adjustments, or at least you can contextualize the assumptions you made that went into those spreadsheets, so to speak.
Andy: And yeah, and I'm glad you say that, because I think now people are learning. Don't just rely on the spreadsheet math, you know. With that, you said an important point as well, which is like, you got to look at like what's happening in the sales process. Is it more involved than we thought it was going to be? Right. Like, um, which is a good call out too. And that makes me think, and want to ask you this is like, what makes an effective sales cycle from first meeting a close for you? Like, how do you, how do you think about that at a high level? Right. Um, and you know, we can go through like stages, but. for people just starting their sales cycles, what do you look at to make sure it's effective from first meeting to close?
Brian: Yeah. I mean, it's very different, I feel like, depending on stages. Early on, it's obviously much harder, I think, versus once later when you get a system and you kind of really know what to look for and you have a much more thought out process. I think for us, Well, it's a good sales cycle is yeah. One, you got to make sure, um, you really understand the pain points and what they care about. Are we asking the right questions? Are we getting in front of the right people? Depends if we know the right ICP or not. Um, we're, uh, we're a med pick place, but like early on, we weren't like, you know, We weren't really utilizing anything. Yeah. It was more of like, because we reduce so much friction is like, could we get them to commit to at least doing a free trial? Right. Cause we, again, we're like, we're not going to charge for it. We'll do all the work. And so that to us was like a very like, okay, well, why, why not? Right. Like, and we were just trying to find really champions of the business at that time and doing a lot of creative things. We were hand making. lots of stuff and going to the offices and like we have like photos from the early days where and now you have like Sendosa wasn't really that big then either so we were like hand making a lot of stuff and so um you know for us it was just we were very involved in those early day sales cycles um yeah now you know we're using a variety of different tools um you know uh you know like like gong and clary and we're you know you know use medpick and we're you know uh i think it's still more work to do, but a lot more thoughtful from that perspective. But yeah, but at the end of the day, you know, do we understand, or like the three whys is like a big thing that we've always liked. Do we understand, you know, kind of the key parts of that deal cycle and can the rep speak to that? And then that to me, I think are like usually end up being the core things. There's always going to be stuff that comes up that's out of your control, you know, especially in e-com, retail, you know, There's been a lot of shifts and changes in that business and that's going to happen. But when we focus on stuff that is in our control and make sure we really dig in and understand that and are in a good spot has been, I'd say, the core focus.
Andy: Yeah. And I think from the outside perspective, well, kind of on the inside perspective, because I know y'all's business pretty well, but I think what you do well is You know, a lot of people talk of time to value, right? Like when you sign a new customer, how fast can we get them value? Well, you guys get people like in a trial as fast as you can, and you get them like ROI within a week, which is, which is crazy, right? Like, this is what I've noticed. And so it makes the deal a no brainer from that perspective. If you can get them in a trial, you know, you're probably conversion rates are insane because you're like, Hey, why wouldn't you do this? You send a, you know, you send a text to your list. You make X amount of money. and this is a channel you weren't using before.
Brian: Yeah, we give a projection. We'd be like, here's how much you're going to make. We'd often like blow that on the water and they thought the projection was crazy. So yeah, I mean, our trial conversion rates, I think we're like mid nineties into paying customers. It was funny because a lot of people would ask me and they're like, oh, should we do a trial? But it depends on the business, right? For us, we were able to do it where we could get going very quickly and we knew We had our eyes to be just very focused on the point where we were like, we knew we were going to drive a lot of new. So we were just very confident. And so. You know, for us, that made sense. It's interesting. Now, as the space has matured and what is in the right approach, but also we have new products and we have, like. a couple of really like great AI products, which you might be aware of. But for there, you can almost need a month or two months of data to really optimize and make it work well versus like when you're SMS, especially early days, you're right, you just get the tag live and you're like, boom, you can literally see in a few days. And so how we kind of position and show that value is kind of shifted a little bit. But for us, a lot of our principles all about, yeah, if we're very much performance driven and we want to show our value and we're willing to kind of put our money where our mouth is. And that's kind of what we'd always say is like, look, Cause again, there was so much reticence around SMS as a channel back then. It's like, we are doing all this work for you. It's free. Like, yes, this may, this projection that we're showing you may look unrealistic. Well, look, happy to have you chat with other people at a similar experience, but like, here's the math, here's what you're going to see and all the investments on our side. So like, you know, if it doesn't work, it's, you know, it's really going to be on us. And I think we've tried, we've kept a lot of that mentality through the years.
Andy: Yeah. And, and, and something, okay, this is another question that I think a lot of people want to know about, which is, you know, you have these products that came up during the Zerp era, they, they, you know, investors told them, Hey, you need to do multi product, you need to do another product, another revenue stream, all that fun stuff. And And I know intensive is going all in on doing some email as well as a, as a separate product now going against Klaviyo, which is, you know, behemoth. So, um, you guys have been doing that maybe what for a year now or something, you know, going multi-product trying to sell more email. What is changed in your beliefs from before when you started doing this multi-product approach to app to now, right? Like what, what has changed and kind of your mindset there?
Brian: Um, yeah, no, that's a great question. I'd say the beginning of, um, our revenue kickoff into this year, kind of walked through something. Um, that I believe the folks over at HubSpot had kind of used like this, you know, the idea of like the S-curve, but like these like stacked S-curves, right, where, you know, you kind of go through this initial, like for us, phase, right, where it's like this very kind of flat, difficult part, you're trying to find product-to-market fit, and then it kind of scales up, and then it kind of matures, right, where everyone's kind of competing, coming in. For us, going from single to multi-product, You know, 1, I'd say some businesses don't need to go and say, need to go multi product. If you just have a massive. Like, addressable market, like, maybe like a snowflake or something like that. Most kind of world class. B2B software companies that want to go, you know, 5, 10 billion of revenue need to go multi-product. And I think, so I was kind of knew it was probably going to be some sort of necessity, but for us, it just came from my customers asking. They just really loved our CS team. They loved our product and asked if we could build something like Gmail. So we started building it, you know, five plus years ago. We've been more, you know, it's probably been, you know, more recently started commercializing it for sure. And yeah, I mean, it is a very different motion. And now we have a, especially with our AI products, a number of different products. So we also, one of the things I didn't mention before, Most people will focus on a specific segment like SMB and then go upmarket. We kind of started large mid-market small enterprise and went upmarket and downmarket at the same time, which was very challenging at the time because it's just such different motions, everything from partnerships to sales to support to the ecosystems that we would play in. For us, when you go multi-product, very similar, right? But the biggest change, I think for me, is it comes down to discovery, right? When you come in and you kind of know your ICP and you're like, look, they're either, it was almost all Greenfield. So it's just trying to evangelize SMS, get them excited. Here's why you should care about it. It'll be 20% of your revenue within three to six months. And, you know, that focus and evangelizing it was like the big focus and then kind of as it got more of a mature space, more competitive, rip and replace like that evolution. And then yeah, now it's like multi-product, you know, how do you then go in? You don't just go in with like this mindset of like either doing SMS or not, you have to kind of evangelize it or hey, why we're the better mousetrap and you should, you know, work with attentive, you know, hey, maybe you've already appreciate SMS and now you can show what additional things you can do in attentive. Now, yeah, it's like, well, are you looking at SMS email together? Why is that? Or what is the timing, right? And they could have contractually, you know, different things you have to deal with in deal cycles, or people sharing the RFP, both of them together. And so, you know, your approach really needs to be grounded and like in your, your that initial phase, you have to like slow down and do a lot more of that, I think discovery. And so that's probably been one of the biggest changes, transitions for us. I also just think, you know, when you grow as fast as we did and add a number of people and a lot of people just saw a lot of success, getting the people to shift and buy in to all these changes that you need to do to successfully do multi-product as an example, or any big transition as you grow, that's the other big challenge, right? And I think you had a number of people who just embraced it and saw, wow, you really figure this out, you can be way more successful because you now just have a lot of different ways to help drive value for customers and even that time to value. And then some people are just like, no, they got really comfortable with what they knew. And we've had to put more work in getting them to kind of uh learn and adapt because it's always harder at first right like you know there'll be other sms only companies that will try and say oh they're not focused on sms like we have a massive team like innovating and building sms stuff but they'll try and portray it like that right and then uh you'll go in and communicate with people that are maybe saying email and sms And they've been selling email and SMS together for a long period of time. So you go from being the expert in what you do and just really focusing on that to having to kind of evolve a little bit. And that takes a different skill set. It takes some time and learning and then positioning everything in the market. All of that changes. So that's almost like that flat part of the S-curve. And that's what we've been going through the last year or two. And so we've been putting a lot of work in, but it's been exciting as we start seeing all that be like a lot more and more successful, but it was definitely a lot of work and still a lot of work in the road ahead.
Andy: Yeah. And I saw someone said something, I think it was Jason Lemkin, who was like, hey, if you launch a second product, You need to have a completely separate team to do it because this is his thought, right? I don't actually agree with it, but you need a second whole team to do it because reps are going to do what's easy, right? Which I kind of agree in some cases, but in others spinning up a whole new team is just, you know, nightmare in my case, right? And from what I've seen. So. What are your thoughts on that from separating a team that just sells one product, product A, and a team that sells product B versus a team that sells both? What are your thoughts on that?
Brian: Yeah, that tends to be one of those things people feel very passionately about. We had a similar conversation around new verticals, having a new verticals team. Not everyone agreed with my approach even internally, so I totally respect there's different ways, I think, to be successful or different viewpoints for these things. Again, why I love like stuff like sales velocity, because I think it kind of touches on, I think what Jason gets at, which is, I think, to be honest, good reps will go where it's easiest place to make money, right? And so I think you can address that in different ways. You can do SPFs or compensate or, you know, do different things to kind of help push new products, right? Or incentivize different behavior that you want. Um, you know, I think really leaning in, I try to just like, I enforce and everything I do, I reach out to me for help. I'm like, what have you done with email lately? What do you need help there? And I make them answer that question first, like my skip levels of people. I make them also, when we talk about review deals, they have to have at least one with email. And I talk about it, my memo, like. almost every single week we highlight wins. So I'm like, my view is, I know it's going to be hard emails, like a competitive mature space. Like it just has to be ingrained in everything we do and are pushing and trying to reward that. And then also, you know, I think your top reps making sure that they're bought in on board because they'll do it. They'll figure it out and I'll show a lot of success. And then people will see that and they'll be like, ah, okay, I want that. Or I just had a rep say to me for the first time. So he's like, wow, like more than half my paycheck was from email. And Those eyes lit up and they start seeing that and they're like, wow, this is great. And especially now that the product's gotten to a point where we get a lot of great feedback on the product, all that kind of comes together. But early on, it's just tough because there's a lot of that feedback. For us, I actually did build a separate team initially for email because we just started by signing into our existing base. And so that was really the only people that we targeted early on for email. Um, for a variety of reasons, part of it was like we had to redo our whole sales person since it was like a 12 month project. And there was just those logistics stuff. Um, but also those are the customers that we're kind of asking for. And we wanted to like, say like, look early on, it's an alpha, it's a beta. Uh, we don't want to rush it out because I think for us, um, again, like, I think we're known for having a really good product and service for SMS. We didn't want to be like, just trying to rush on some sort of like, Look like some sort of cash or revenue grab and we're just trying to like tack on some like check the box products. Like if we're gonna do another project, we want to do it really well. But look, it's not going to be perfect out of the box. So how do we then have that right process? So I actually wanted to hire people and my view was We tend to be the experts in SMS because that's what we've done and learned. We show up on a call, and especially when the space wasn't as mature, we're going to know more than the customer on the other side. It's the opposite for email, right? So if our product was less mature when we initially rolled this out a few years ago, and customers have been doing email for a long time, you're just at a big disadvantage. There's less trust because the product is newer. And then they can easily tell if they know more than kind of the rep. So it's going to make the rep less comfortable and less confident. And it's also going to have less confidence in the brand. So I said, look, I want to get, um, a small team, hire people with lots of email experience. So they understand our product. They know what to answer the questions and they saw that comfort level. And then also more importantly, make sure to align incentives. We didn't want to just sell any deal. Like we wanted the right deals and feedback. So it was like, Hey, We want to be very open about what we can and can't do as the product is evolving and building because the last thing we want is an existing customer to take something on because they have trust and attentive and then have a bad experience. And for me, a product like email, rolling into a mature market, something like this, I take a very medium and more long-term approach to success and try and work backwards. What do I think this can be over what period of time? And if you do that, you're gonna have a very different approach, right? you have to build that good flywheel, you have to be in front of the right customers, get the right feedback, evolve and kind of more build slowly and then scale very quickly, versus when we went into SMS, or even with our AI products, where it's like all greenfield, and you kind of build like your initial product drives a lot of it, it's great, you get it out there. And then you're like 10 and growing. One of them, I think we had like six or 700 customers live within a month using it. It was like the fastest growing thing we've ever done. For email, we didn't even want that. We wanted the right customers and then we like trying to be very intentional. Now, we've expanded to more of an account, like a fuller account management team that can all sell email. And like our new business teams are doing it. We started with our mid-market team and they've been great. They've been testing and learning. And like their approach for how they do it is very different than upmarket for new business or existing teams. So they all like, you know, are kind of testing and learning and kind of adapting a little bit how they want to position these new products. Is it a land and quickly expand? Is it trying to sell them together or a combination? And what are the right things to look for to take one strategy versus the other?
Andy: Yeah and you know something you mentioned I think this is a big mistake in this multi-product game that people make is they They released the MVP of the, of the multi-product that, you know, Oh, you know, at outreach, we would have some competitors say like, we have sequences now we, we bolted it on and then people go try it. And they're like, yeah, this is nowhere close to like what the company does. It like relies on this. And then, but you need promise. You're like, yeah, we're the same thing. We have the sequences. And then you're right. You wrote that trust, which is kind of like hard to gain back. We're actually experiencing this now with, with a distribute my company. where we build digital sales rooms, right? But like with mutual action plans and all that stuff, but like, that's what we do and what we focus on. And you have some of these other companies seeing like, this is where the world is going and they're trying to bolt it on. And now we have, and I tell everyone, I'm like, you'll be back in three to six months. I promise you, it's not going to work for you. And it's like clockwork, right?
Brian: They're like, Oh, it's already bundled. And we're like, that was part of our playbook there. It was like, just, okay, here's what's probably gonna happen. Let's keep in touch. And like, um, but yeah, it's funny you say that because what ends up adding to is a lot of times the employees at those companies, like we would talk even like sales tech that we use, that we'd reach out, get a really good pitch for someone to expand to some new product. And then, you know, we'd either hired someone from there or someone knew someone there and they'd be like, yeah, it's actually not a great product yet right now. So like, Work gets out. It's either customers that use it that have a bad experience, employees themselves. I know we have competitors. We've all done it where it's like, okay, you have to start with that initial belief internally and externally before you really try and focus and scale. And there's just a lot of pressure from exec team, from investors, from board. They're like, they wanna see it just go up into the right. And I think a lot of times it can, if you try and go up like this, then it leads going sideways or like this, because then you're dealing with internally and externally this really, they all remember the really bad experiences. And then it's that much harder to get past that, right? And so getting that right balance of like, hey, I love being aggressive. I wanna like go in, I wanna win, I wanna go fast. But like, you have to think about it over what's the right timeframe that you're being aggressive. And I think being aggressive, for going to a mature space like let's say email versus like AI, to me how I define being aggressive is very different, right? It's going to be much more intentionally on and try to learn and get feedback and the right focus and then we can go and be very like okay great now that we've like feel really good about this, we're going to do it versus again, if it's like a brand new space or something where, Hey, you're just trying to get it out there so you can test and learn. And you already know it's going to like, they're not doing anything or don't have a, there's no complimentary product, um, that they're comparing it against.
Andy: Yeah. And, and you, you describe something very interesting too, which I think people need to realize, which is like the maturity of a market that you're going into. Right. Cause I think a lot of people will build, um, you know, new products, and there might be a new hot space, right, kind of like where my company's at right now, like, you know, it's embryonic, but it's growing. And it's starting, we're starting to feel like a lot of people like, Oh, yeah, this is how we should run a great process in one system. And then, you know, so it's great. So we can test a lot of things, we can do that. But if I was selling another sequencing tool, you better believe that if I better come into that market, and like, have it dialed, because that market is so mature, right. And so I think when building people forget about that, like the market maturity and the market.
Brian: And how important it is like sequencing, like for us so much of our pipeline is through outbound. And so if you're going to mess with that engine, like you better, better be like pretty buttoned up. Now, maybe not all companies are like that, and maybe they don't care as much, and that's easy, but that's what email is for us. People really care about email. It's a very important marketing channel for them, even though a lot of people are like, yeah, email doesn't mean people read them. It's still a very important channel for marketing. So that is very important to know. So when that is the case, you have to approach that very differently than, again, a different space or one that's kind of more of an evolving space, if you will.
Andy: Yeah, absolutely. Well, Maki, this has been great, my friend. Thank you so much for coming on.
