88: Kyle Porter Salesloft CEO

Hey listeners, this is a special episode of Make It Happen Mondays. This week's guest is Kyle Porter, CEO and co-founder of SalesLoft. I've become good friends with Kyle over the years, and we're going to be talking about his journey with SalesLoft, doing sales right, and a preview of Rainmaker 2019. I'm not sure when you're listening to this, but at the time this podcast goes live, the promo code JBVIP is still good for 50% off tickets. I hope you enjoy the episode as much as I did, and I hope to see you at Rainmaker March 11th through the 13th. Good afternoon everybody, this is John Barrows with Make It Happen Monday. And I can't tell you how excited I am for today's guest, because I've been working with this gentleman for the past eight or nine years or so.

And the alignment between what we've been doing has been fantastic, and also he's become a very good friend of mine. So I'd like to introduce you all to my good friend Kyle Porter over at SalesLoft. Hey Kyle, how are you doing today, man? I'm doing very well. Hey everybody, excited to be here. John, thanks so much for having me on. We always have a blast getting together, but I haven't had the opportunity to be on a Make It Happen Monday yet, so this is an honor for me. And my goal today is to share transparently, maybe drop a few pieces of information that can hopefully be helpful to the audience. If you get one thing out of it, I'll be happy, and let's dive right in, man. I'm excited. Yeah, this has been a long time coming, I think.

I've been trying to get us to the point where I think it was worth you and I having this conversation, and now it's ready for a couple of reasons. One is where we are in the marketplace right now, and two is what we have coming up here in the next couple of weeks, which I am fired up about, which is Rainmaker 19, right? That's right. Rainmaker March 11th, 12th, and 13th in Atlanta, Georgia. We'll have 1,500 modern sales professionals here, the best of the best, and there's a lot of things going on that will make this really valuable and relevant. I know a lot of your audience is already going to be here, but we'd love to see more people sign up and get down here for Rainmaker. The list is getting closer and closer to the date where my marketing team turns off the ticket sales.

Yeah, and trust me, I know those sales are going well, too, because I've actually put together, me and my team, my whole team is going to be there. This is the first time the whole Jay Barrows team, and not just me, are going to be down there, so we're fired up for this. And also some of the stuff that we're going to be talking about in our conversation, which is the difference between sales-ready messaging versus marketing messaging, where things are going, and what we need to be paying attention to, which is really what I want to dive into here. But just some quick context for everybody out there, how Kyle and I know each other. So I want to say about eight or nine years ago, I did a training, right?

And, you know, everybody knows that, you know, well, people who follow me know, like the why you, why you now, you know, like the Jeff Hoffman, the one that he came up with, right? And it's all about doing some personalization, right? Going on somebody's website, being like, hey, what's up? I was researching, I saw this, let's talk about it, boom, right? Sending it out to an executive. And we do these live application in class. And one kid actually sent you an email during class. And do you remember what you did with it? Well, I remember I had received a lot of terrible sales emails. And we weren't in the sales engagement category yet as a company. But we were thinking a lot about how to deliver a customer with a better experience.

And I got this guy's email, and I remember being blown away at the quality of it. And so I turned around and wrote a blog post and included the email in the blog post. And that's how we got to know each other. Yeah, and actually, that kid was so fired up, he actually sent me your blog post. It was like, dude, check this out. I sent it to a CEO. You know, and he actually wrote a blog post about it. So then I kind of pinged you. I was like, yo, what's up? I trained that kid. You want to talk? And that's what kind of started us along the path. And then, like I said, I think you and I are in violent agreement about a lot of different stuff, personally and professionally. And like I said, I appreciate our friendship.

We only disagree when it comes to professional sports teams. But you seem to win that one pretty frequently. Yeah, we're in the golden age right now in New England sports. So I won't run that, too. And again, for those people who don't remember who weren't there, two years ago, Kyle and I had a bet about the Atlanta Super Bowl. And I will say, actually, I still got it right here, as a matter of fact. Oh, are you kidding me? I'm going to bring it up, man. Kyle had to wear a Tom Brady jersey up on stage at Rainmaker in front of like... I put that down now. So anyways, but one of the things I've always... I took a shower right after. Hey, you're lucky, by the way, because that was... I've never even worn that jersey.

That was a signed autographed by Tom Brady game day jersey. I've never even worn it. So you're the only one who's ever worn it. So if that makes you feel any better. Greatness, recognize greatness, right? So, but it kind of leads to... One of the things I've always said and admired about you is the ability for you to evolve, right? I mean, when you said you were just thinking about the sales engagement when that email hits you, right? I remember the first time we got together, or the first time I noticed what you were doing and what you had put together, it was like giving alerts off of LinkedIn, right? Like when somebody moved a job, it would be like, oh, Kyle just went from X to Y company, right?

And that to me, and that was before LinkedIn could do it. And that to me was like, holy shit, this is fantastic. And then I remember you shutting it down. And I'm like, dude, what the hell are you doing? Like I'm telling all my clients about this. I think this is fantastic. But what were you seeing, right? Because there's another step and then another step. And you kept shutting things down and reinventing yourself. Could you give the team a little bit of context on that? Because I think that evolution is going to feed well into our conversation here. Yeah. So short stories, I've been a salesperson my entire life, going back to childhood, where I was selling beanie babies, baseball cards, comic books, figurines, Olympic pins, you know, 1996.

And what I did is I just love the look on someone's eyes when you could deliver them something that they couldn't get anywhere else, that they really, really wanted, that they were struggling to find on their own. And that just invigorated me. And as I got into professional selling, what I recognized is that I was doing really well selling. I was making six figures first year out of school, selling in the corporate environment, and doing it by understanding my customer, by being able to lead with understanding their challenges and problems and connecting with them authentically. And I called it at the time just relationship selling, right? And then later, you know, I realized that not everyone in sales really, you know, behaved that way.

And the sales profession had this other reputation, and I was disgusted by it. And so when I started Sales Loft, I had one mission was to bring sincerity into the profession of sales. And that led us to try a lot of different things in order to identify products that would help sellers connect more authentically and deliver more value to their customers. And we'd try something, and we'd spin it up, and we'd see where the problems and the difficulties were. You know, that was one of the products. But another one was a data service that we built, and it would let individuals create or companies create these accurate and targeted lists of leads. And what I realized is that, you know, this thing took off, by the way.

It went from $0 million to $7 million in a two-year period of time. But I canceled that product because it didn't match with our values. And what I recognized is that these companies were buying this service to generate this long list of leads, and then they were dropping it in the marketing automation spam blaster or some of these mail merge, you know, automation engines. And they were just turning the wheel, and it disgusted me. And so what we wanted to do is identify what are the best sellers in the world doing. And they are understanding who their buyers are. They're targeting the right accounts. They're finding the personas in those accounts. And then they're tailoring the messaging over a series of communications, phone calls, and emails over periods of time.

And we said, well, let's build this, man. Let's build something that helps this workflow so that reps can deliver a better experience as sellers. So it's always been the same North Star, but just trying different ways to get there. But would you skip there, which I think is important for any entrepreneur out there who's listening. And so, you know, a lot about this podcast is a lot about tactical execution things. But it's also about kind of aspirations, right? Like a lot of people that listen here, they want to be an entrepreneur. They want to start their own business, but they might be afraid to, or they might be holding on to something that they don't think is, that they know could be better, but they're afraid because they might have gotten some money.

I mean, you had investors that got you from zero to seven million, and you had a legit company going, and you just shut it down, right? Like, and you went back to them and said, yeah, sorry, I know I have a super successful company. I'm going to bail on that and start a different one. Is that cool with you? Is that pretty much what you did? I mean, give or take. Yeah, you know, what we also did at the same time is we went on a whiteboard and drew out the future for the sales engagement market. And this was in 2014. And one of the biggest investors that I know in Atlanta, he came in, saw that presentation, and wanted to invest in the future of that product. So we had this lifeline into the future, you know, the backs of our investors.

And they were long-term believers in the vision as well. So it wasn't a super hard sell. It was a hard sell internally to the staff, especially the reps who were crushing it, selling that old product and making a ton of money with something that was easy to sell, that the customer understood, that they were getting paid well on. I mean, that was the difficulty. And we had a tombstone in the corner of the office, RIP Sales Loft Prospector. We played that song, and I sung a dust in the wind. You know, we had to memorialize the moment. And it was harder internally than anywhere else. And some customers didn't like it also. But, you know, we've since shown those customers a better way. And that, again, from a business building business standpoint, one of the other things I have always admired is the culture that you've created at Sales Loft.

You know, I've said this before, and I'll say it again. If there's one company that I would ever work for ever again in my life, and I won't because I'm a pain in the ass to work for and with, but if there was, it'd be Sales Loft. And it's because of that culture that you've created there. Thank you. That's an honor. And I'm dead serious about that, you know, for anybody listening out there. So, and one of the things that I think you do a really good job of, and I try to do as a leader myself, is paint the vision, right? You talk about that vision. Because I always say you can't get people to do more than what you're asking for from them unless they understand the vision of where you're going and how they fit into that.

So, how do you constantly live? You know, I want to get into the future where sales engagement is going. But a nice little sidebar here on culture. How do you live your values, if you will, and make sure that people are bought into this? Because you've done some stuff at Sales Loft from a cultural standpoint that I rarely see in most organizations. You know, I think I got lucky. I had a crazy childhood, early past, and we can get into that later or maybe another day. But what happened was is I started to find myself being real transparent and vulnerable and authentic in my life. And what happened was the ROI on that authenticity was through the roof. And so, I just kept doing it and doing it and doing it.

It felt good. And so, for me, this business is a direct reflection of who I am, what I believe, and what I believe that others should believe. And so, from the very beginning, it was how do we bring a level of sincerity to sales? How do we activate the authentic seller in everyone, right? And so, I wake up with that mission and passion. And then the other thing I wanted to do is I wanted to create an environment where others could come to learn more, do more, and become more, to take the talents and skills that they had been given and that they had earned and use those to make the world a different place, to make it a better place, to find fulfillment. And so, that's what this company is all about.

And I wanted to do that even before I knew it was going to be called Sales Loft, even before I had the domain, right? And so, that was where it all began. And so, we just, you know, we work really hard to make sure everyone is on board with the North Star here, that the values and the shared behaviors are behaviors that they hold deep in their heart and that they want to get better and better and better at. And then we, you know, we create an environment for where if that's not the case, then you're going to not want to be here. And if it is, you're going to find tons of, you're going to thrive in this environment if you do. And so, we wake up every day with our people, you know, loving our people so they can turn around and love on our customers.

And it's worked out so far. It's difficult. It's, you know, it's actually not complex, but it's very, very, very hard is the best way I would describe it. You know, to live a values-oriented, purpose-driven, mission-led company, it's just, it's kind of blocking and tackling, but it's really hard blocking and tackling. Well, especially as you grow. Like, I mean, how many employees are you up to now? We're 360 today. Shit, man. 360? Oh, shit. So, I mean, you know, I have, like, 20, 30, 40, 50 people, no problem, right? All of a sudden, you break into 100, and now you've got problems, right? More money, more problems. So, how do you, let me ask you my own genuine curiosity here. Like, what is your approach to, like, mission statements and those type of things?

And do you have one in the why, right? Unfortunately, what I see a lot of companies is they come up, like, the founders come up with some mission statement with some consultant or whatever it is that they beat each up over a couple of words, and then they throw it up on a board, but they don't live it. So, do you guys have a defined mission statement, or is it constantly evolving? And what's that North Star for you? We absolutely do, and it does tweak from time to time as I get smarter about the language that would go into it, but the whole entire philosophy of it never changes. And so, from the beginning, I used to use those words, sincerity in sales. I don't use that as much. What we say is the purpose of the business is to activate the authentic seller in everyone, right?

And so, it starts right there. What's the reason this business even exists? Because if it was to make money, there's 100 different things I could go do to make money, right? And I've already made money, and, you know, that's fine, but that's not enough. That's not what it's all about. And so, I believe a company's purpose should really – you can kind of ask the question, like, why five times to get to the real, real, real why behind it. And it should be something that's one stop short of saving the world, you know, making the world a better place. And for us, activating the authentic seller in everyone does make the world a better place. So, that's our purpose as a business. And if you're about to be hired, whether you're a QA engineer or an accountant, a salesperson, an executive, if you don't believe that that's a worthwhile cause, then there's no reason to be here.

You know what I'm saying? And so, it starts there. And then the mission is a little more concrete about what the business does every day. And so, our mission is to empower our customers to enable their reps to deliver the best sales experience in a way that generates the most revenue for their companies. So, that's the mission of the company. And then we have our values, which are service and customer first. That's number one. Team over self, which is like Michael Jordan in the championship days before Michael Jordan in the scoring leader days. It's bias to action. I think you know a little bit about that. It is focus on results. Focus on the results is a formula that we have that is be authentic and transparent and admit mistakes and weaknesses so that we can dive in together and solve problems with conflict.

So, we can make commitments to each other. So, we can hold each other accountable. And when we do that, we have a focus on results. And what did I say? I said, biased action, team over self. I said, which one? Oh, glass half full is the fifth one. And glass half full is, it's not like everything's wine and roses. You know me. I'm a realist. I'm not thinking like everything's sunshine. But what I do is I recognize the whole situation for everything that it is. And that's what us as lofters do. We recognize the good, the bad, the ugly. But we select the positive path forward. So, we make that decision to go forward positively. And those make up the values. And we're looking for those to live in your heart before you join the company.

But you don't need to be tens on all of them. You might be a seven on one. You might be a nine and a half on the other. And what we want is for you to come in hoping that you can take that seven and turn it into an eight. Right? And it's been cool for me because, you know, just even just speaking about them over and over and over again, hiring on them, reprimands, praises, promotions, everything on these values. It's caught me in a situation where I found myself taking kind of that negative step. And I go, oh, whoops, turn back this way. Right? So, I caught myself in course correcting the moment. And a great mentor told me that leadership is when you can make great course corrections. And the ultimate leadership is when you can make a great course correction without having to make the mistake first.

Nice. I love that. And for those of you listening out there, I can't tell you how important this is as far as what Kyle just mapped out there. And because I went, I actually went through that process at the Gary Vee 4D session where you go to Gary Vee's office and really what they focus on is the why. Right? Like, why are you doing what you're doing? And, you know, ours is sales done right. Right? I actually have it, you know, sales done right. And then, you know, our values too. And I actually, a long time ago, I put together, I don't know where I got, this was literally like 20 years ago when I first started, when I was a first VP and my first startup. You know, I came up with my 12 guiding principles, right, of how I live my life.

And it was work hard and smart, you know, always ask for feedback, you know, find your passion or find something else to do, like all those things. And I remember using, and I still have it to this day, it's right there. And I would, anytime I would hire a rep, I would say, look, these are my values. This is where I'm coming from. I just want to let you know when my feet, when you get feedback from me, this is where it comes from. Now, at the time, I didn't say you had to live these values too, because they were just mine, right? But at least you understood where I was coming from. And so everybody knew exactly when I said work hard and smart, and you went home at 4.30 in the afternoon, and I was a little bit annoyed with you because I was at the clock at night.

You kind of knew where that was coming from, right? Yeah. I love it. Understanding your values is critical to success in business. I mean, if you're building a business, but also if you're looking for a job, right? Because if I'm looking for a job, and I look at, the first thing I'm going to look at, first of all, can I believe in the product? But then I cannot believe in the company. Yeah. And what is their mission? What is their purpose? Do they give back? And do their values align with mine? Because if they don't, I'm not going to be successful there, right? That's right. I love it, man. And actually, small sidebar on this one, leadership. Did you see what happened? So I don't want to go into too much sports here, but I'm curious on your perspective on this one.

When the Patriots, like this past Super Bowl, the coach on the Rams, did you see what he said at the end of the game? Did he say something about getting beat? He said something about, but it's the way he said it that I'm actually kind of curious. I'm genuinely curious about your position on this. Because what he said, I mean, he was a Bill, I forget what his name is, but he's like a Bill Belichick, like, oh, my God, like, I love you, Bill Belichick, right? And he even, you saw him before the game being like, man, I appreciate everything you've done for the game and everything. And afterwards, he said, I flat out got outcoached. And it was an emotional thing, and it was a transparent thing, and it was, I mean, you could tell.

It was right, I was like, I got smoked. I got outcoached by Bill Belichick. Now, my question for you is the nuances matter on this one, right? Because I was curious on how that affected his team. Because Bill Belichick never says, I got outcoached. He always says, I could have coached better. So their coach, like, literally admitting defeat, my question is, and saying, like, straight up, I got coached. Fast forward next year, the Patriots are in the Super Bowl with the Rams again. If you're on his team, are you walking in there being like, we're going to win one for our team because our coach, because, you know, he's better this year and that type of thing, and he was transparent with us? Or are you walking into that game going, man, Belichick's in our coach's head, and we're already lost here because Belichick is still better than our coach.

You see what I'm saying? Yeah, I mean, I think it all depends on what happens after this in those rooms that we won't see. You know, when he addresses the team after the game, what are the addendums that he throws on that, right? Because if he says, I got outcoached, and I can do better, and I'm going to get him, you know, I mean, that's a different story, right? But, I mean, I can coach better is kind of the same thing as I got outcoached also, right? I mean, to me, it feels like, at the end of the day, it is actually the same thing. If you didn't get coached well enough, then you got outcoached. It is, but I do think nuances matter. Like, I got smoked versus I could get better. It's kind of glass half empty, glass half full approach, right?

But it's also, if it's not the final statement, right, the declarative statement is the follow-up. And if that's all he said on this camera, then he left an opportunity behind to say, you know, hey, reality is X, future is Y, right? I guess that's your philosophy on, because you said transparency has helped you throughout your, and I'm the same way, man. I always tell people, I'm the worst liar you'll ever come across. I just suck at lying. So, I guess, is there a threshold for transparency? As a business leader, is there a threshold of transparency that you have to be wary of? I mean, I've told my staff about my childhood insecurities in the time I got arrested. I mean, you know, like, where's the line?

I don't know. Well, I guess from a business standpoint, you know what I mean? Because there's investors, there's money involved in what you're doing. Well, there's things you can't do. Like, you can't share salaries and things like that. And if there's lawsuits or, you know, anything like, there's things that you just can't do fiscally or through corporate responsibility. But, you know, for me, I always play the game of, you know, here's who I am. Here's what happened. Here's the situation. And here's what's going to happen going forward. That's the piece. You know, that's where I'm aggressive. That's the piece. And I think that's the piece that I thought that the coach missed a little bit there, which is, you know what?

I got smoked, Belichick killed, but man, I can't wait for next year type of smoke, right? So, let's talk about next year. He's not going to get me again. Yeah, exactly. So, let's talk about next year as far as future and evolution because we've set the stage here, you know, evolving businesses, having a vision, those type of things. Sales engagement right now, all right? I personally think we're in this transition phase right now of sales in general. And I'm going to put a couple of benchmarks here. Generationally, right? When I grew up, you know, Gen Xer, right? It was a numbers game. It was a pure numbers game. So, it was like, hey, make a $50, make $100, whatever it was, right? We've now evolved into a world where we understand quality matters, right?

Account-based marketing, you know, buyer intent, those type of things. But, because Gen Xers right now are the leaders, if you will, it's really hard to coach against quality. It's hard to coach quality, right? It's easy to coach against numbers. So, as much as a manager wants to coach, you know, hell, let me show you how to be authentic and all this other stuff. It's a lot easier for me to admit, hey, Kyle, did you make your $50 today? So, I think we're in this weird world where everybody understands quality is the answer, but we're still cranking on numbers, right? Yeah. And, you know, we're short-term, it's monthly quotas for reps, you know, Wall Street's beating up these publicly traded companies, go, go, go at all costs, right?

So, we're in, I think, understand, you know, future is important and all that other stuff, but short-term, I've got to hit my numbers and I've got to do my thing and I get managed that way. So, I think we're in a transition. And, I think a lot of technology, a lot of people right now are teaching the technology on how to do our jobs that eventually is going to come and replace a lot of what we're doing. And, that's where I see sales engagement right now is a lot of these reps are using these sales engagement tools as sales automation tools. So, with that, where do you see this going? And, let's focus on just, I know the vision of Sales Loft is to really get all aspects of a business from a sales engagement, customer success, account managers, account executives, and SDRs and BDRs.

But, let's focus specifically right now on the outbound engagement. Yeah, prospecting, account development. Because, you are actually in this more than I am from a tech standpoint. So, where do you see this two, three, four, five years out going? Well, the first thing you said, it reminded me of a quote from Danny Meyer. Danny Meyer is the founder of Union Square Restaurant Group and Shake Shack. It's a $4 billion burger joint, right? He's going to be coming to Rainmaker. He's one of the keynotes. And, what he says is he says, because he owns this fine dining white tablecloth, number one restaurant in New York, and says, you know, it's easy to coach someone on how to set a table beautifully.

It's impossible to coach them to want to set the table beautifully. And, so, that goes into selection on the front end. In leadership, the first step in leadership is attracting the right talent. The second step is inspiring that talent, right? Fueling the flame. And, then the third step is developing that talent. So, that's what leadership is all about. And, I totally agree that we are walking this thin line with our account development practices, with our prospecting practices. Because, on one hand, we know that customers demand and desire and deserve an authentic, relevant, engaging, human, one-to-one, sincere, problem-solving experience, right? They demand that. But, companies, their organizations, they want predictable, scalable, repeatable, steeped-in process, forecastable.

You know, they have to have that in order to get the financing, in order to get the growth, in order to get the budget, in order to get the hires, right? So, sales becomes this harmonious blend of these two things that are really in conflict with each other, right? And, what happens is a lot of technology is saying, taking this side of the automated, scalable, predictable, and they're saying, let's speed it up. Let's accelerate it. More activities. More, you know, crush your sales. Crush your calls. Crush this. Crush that. And, what's happening is, they're losing that actual part that matters the most of this human engagement component of sales. And so, a lot of these sales engagement companies, you know, their billboard would read, you know, make thousands of phone, crush the phone calls, you know, and like that kind of thing.

And, what ours would read is, deliver a better sales experience. Because, at the end of the day, the customer gives zero shits about your process. Like, oh, you got automation? Don't give a shit. Oh, you got some scalable things? I don't care. What am I going to get out of this? And, I better get solutions to my problems, right? So, I think that's the biggest thing that you have to think about when you come into this market. Now, the next thing is, is that in order to provide that authentic service, it is very, very, very difficult to do it with any sort of speed, with any sort of volume, with any sort of coverage amongst your accounts. So, the goal of sales engagement should be to eliminate the routine tasks and free the rep up to better understand their buyer.

To better be educated in business concepts so that they can consult and serve and solve for their customers, right? So, I think that's the way we look at it. And then the big, big, big thing down the road is, okay, and it's happening now, you know, with our company and what we do in sales engagement, we provide phone solutions, email solutions, social, LinkedIn solutions, and other types of offline communications. And we get to see all of those activities, all of them. And then we get to see which ones worked and which ones didn't, for which personas, in which industries, at what ACVs, at what rep types, at what buyer profile. And then what happens is, now we've got this machine learning that can guide these sellers.

And it can guide them in the moment, educating them real time as they're acting. And it's not based on all the knowledge we know across all the users. It's based on their specific situation. So, each person gets their own ad hoc or bespoke sales engagement coaching. But at the end of the day, they're still the ones connecting. They're still the ones asking those difficult questions, making those difficult challenges to the buyers, bringing the right people into the mix. So, I believe that's the future of sales engagement. Do you think that the SDR role, because I'm curious here. So, here's what my thought is. I'd love to get, if you think I'm right, or what your thoughts are on it, which is the SDR role right now, right?

The ones that do the outbounds, okay? Yep. I personally think that's going to turn a little bit more, a lot more, and shift under the marketing operations side than it is the sales side. Because historically, it's been the feeder system, right? Ever since Predictable Revenue came out and all that other stuff, it was, all right, come in here, do some inbounds, right? Now, go graduate to outbounds, then go graduate to AE, right, or inside sales, and then close SMD mid-market and enterprise. And now, that's the journey of a sales rep. I fundamentally believe, because of solutions like yours, that the SDR role is going to become, first of all, I think it's going to become its own pillar, if you will, in the sales process.

In a sense, it's not going to be a feeder system. It's going to be, I'm going to be an SDR, I'm going to be an SDR manager, I'm going to be an SDR VP. But I think it's going to align with the sales, with marketing and operations, because it's going to be so much more, to your point, using the data, using the insights, leveraging the messaging and all that, and putting it together to engage with that specific prospect, and then analyzing the results. And let's be just very clear on this. That is not a, currently, that is not a sales rep skill, as far as looking at data, analyzing results, and that's usually more under marketing and operations. So, that's my belief, is that the skill set is going to need to change from being a sales superstar, and knowing how to have a conversation with somebody, and that type of thing, and relationship developers, to somebody who can analyze and put the pieces together, and then look at the results.

So, A, what do you think of that? B, if that is true, what's now the new entree into sales, if you will, like a full cycle sales rep? Is it going to go back to what you and I started with, which is, here's your territory, good luck. You have to prospect, you know, yeah, you're going to get inbounds, and you're going to get leads given to you, but you still have to go out there and close your own? Where do you see that? Yeah, so I do agree that sales development sits square, sits between sales and marketing. I may have some disagreement on how close it gets to marketing, because sales development has two components to it. It has the operational component to it, which is content, templates, snippets, automation rules, distribution of accounts, you know, filling in personas.

It's all those things that are very operational, but then it requires the rep to make a tweak at the last minute of all of these communications. There's really two types of cadences. There's a straight automated one, and then there's a teed up one. And the teed up one is beautiful, because what it does is it can take all the different industries of your buyer, all the different personas of your buyer, all the different things that are happening in the market, all the different matchups with your solution, and it can deliver the rep right before they hit send an email that looks pretty damn good, right? But what the rep has the opportunity to do is turn that from an email template that looks pretty damn good to being an email that the owner, that the receiver of that email will know was sent authentically.

And my best example for this is I woke up at 4 a.m. on Thanksgiving morning with about 20 people in my farmhouse in Central Florida. Before I woke up, I went to the computer and I opened up SalesLoft, and I had a cadence that I had built, and it had at the time about 330 employees of SalesLoft, and it had a single template thanking them for being part of this mission and helping us achieve everything that we have, because I was really grateful to the staff, and I wanted to share that with them. What I did is I tweaked every single one of those emails before I hit send, so that when they received it, they know that I put thought into that, and that I cared about them specifically, and the difference is just that much work for that much impact.

And so what happened was I got about 70 emails back by noon that day, and they said things like, I just showed your email to my grandmother to show her how proud I am of the company I work with. That's awesome. And that's the difference, right, because they all would have been able to sniff it out if it had just been, hey, name. Yeah. You know who you've been at the company for? Increase, insert tenure, right? And I'm glad you're working in, insert department, right? And I just wanted to say I'm so grateful for you to be part of this journey, versus, hey, it was great to see you in the hallway on Thursday. Yeah. Hey, I saw that you just launched this awesome campaign. I was really proud. Or, hey, we haven't even met yet, but I know Brian's really excited to bring you on the team, and I heard him say something about it when he hired you, right?

And, like, those are some of those emails, and it was just, it was a difference maker. And so that's what we want to do, empowering salespeople, is give them the opportunity to make that difference in the last moment. And that's why, as long as they have operational support, that that's the on-road to being a closer, because you're starting to know how to connect in a way that allows you to persuade. Okay. So I see that the nuance there makes a difference, right? But it's the challenges is, to your point, of the hiring of that person that does give a shit about making that, setting the table that right, it was a way of showing them how to do it, right? Right? And because I think, you know, that was funny.

One of the things, when I go back to Gary Vee and I went to his 4D session, I asked him, because I was a little bit, this was about three years ago. I will say I was, to a certain degree, freaking out about the old artificial intelligence thing. I'm like, holy shit, because I'm seeing emails that were more personalized than I could write. And I'm like, what the fuck? And I asked him, I go, where does that leave us? And he goes, don't fight it. You know, you're not going to fight it. It's coming, and it's coming strong. But he said exactly what you just said there, which is, be the rep that, before the AI email goes out, because there's always going to be something that a human can sniff out that says, that wasn't written by a human.

You know what I mean? Like, you know, it uses first name, last name, you know, those type of things, as opposed to just the first name. Or, you know, it says something that's, yeah, but that's not how a normal person talks, right? So be that last mile. And I think that's the key, is be that last mile. And your data even proves that. One of the things that shocked me, you have that new sales development report that you just posted recently. You know what, like, is, was surprising and a little frustrating to me, but also, but also a little encouraging, was the 20%, right? The optimal sales email is 20% personalized, which I'm like, okay, but what, in contrast to 100% personalized. Yeah. Like, 100% personalized was, was, was, like, the graph was, yeah, the graph was like, all right, from zero to 20%, it's not that great.

But then from 20% to 80%, 20% to 90%, it's actually, you know, pretty equal. And then it fell off the map at 100%. Yeah. Why do you think that is? Why do you think a 20% personalized email, I get the scale version of that. Yeah, yeah, yeah. Hit load more at that point. But why do you think the 20% personalization was so much more effective than 100%? I mean, I am genuinely curious on that right there. So, what we're looking, we've looked into that, and what we've identified is that the team is writing decent templates. The teams are writing decent templates. And those may match up with the, the, the need in the market with the solution that they solve for it. People are getting better and better and better at writing the templates.

You're helping them do that, right? And, but when you go all the way off the deep end, now you're going completely rogue and you've got these junior people that may not understand these value props the same way. And they're rewriting the value prop of their organization. And so, what we found is, is that taking the, the, the tried and true principles of the proposition and the need and the problem in the market, but then throwing that twist in there that shows the buyer, I'm tuned into you. I'm paying attention, I care about your business, I've got some intelligence, and I'm here to serve and solve your problems. That opens the door for that interaction to happen. And so, I think that's why that, that early, you know, personalization is making an impact and the latter is falling off.

Yeah, and I think that it kind of goes all into, you know, my whole riff on context content, right? And this is where sales and marketing, right? Marketing is content, sales is context. If we're sales professionals, we're not putting any context around our content, we're no different than marketing, and I have no idea why we're getting paid to do what we do. And the only thing that works if it's robotic sales engagement or robotic automation, and the only thing that works is if you just happen to land on, you know, demand that was there and it matches the value prop. So, the demand has to be there and if the demand's already there, they probably already started down the path. If they've already started down the path, then you're an also-ran, right?

You're not shaping the vision for them. And so, I think that's a really important concept as well. Awesome, man. We see a lot of times companies with, you know, attractive products in the market that resort to more robotic approaches. Yeah. And it's really weird because what happens is they see early success. Yeah. Because they target those customers that kind of know or want, are they a good, good fit, and they get great responses. And then they decide they want to move upstream or stop selling to venture-backed SaaS companies, right? And they send those emails to manufacturing companies and financial services companies and healthcare companies. And those guys are just like delete, delete, delete, spam, spam, spam.

And then the companies are shocked and they're like, we have to go and really sell, you know? And then rewind all those old habits to get better at going to market. Yeah. And they probably abused, you know, the conversion ratios matter, right? Because I've had this, and I'm not going to bring up another trainer, but, you know, we have different philosophies. There's this one trainer out there that, like, literally litters the C-suite with very templated emails and asks for, hey, who can I talk to about this? And gets the referral down and focuses on that. And I'm like, no, no, no, no, no, no, no. You want to be thoughtful if you're going to do that. You want to, and he's like, yeah, but I, you know, I can send out 500 emails in 10 minutes and get five responses where you're going to take two or three hours to send 20 emails that get five responses.

So I'm better than you. And I go, no, no, no, no, you're not, right? Because you just probably pissed off 995 people that you're not going to be able to go back to, right? And we all know the quality of your responses are going to be higher too. A response is not a response is not a response. Exactly. So, you know, I think that's something for, for reps to pay attention to is that. When you got 495 bad tastes in mouths. Exactly. And then all of a sudden it's just going to be like, okay, take me off your list. And even if you become authentic, they're like, oh yeah, you're the guy that sent me that BS. Right. And that actually leads me to kind of, I mean, you and I could talk all day, but, but one of my last topics I want to hit on with you here is the difference between sales engagements and marketing automation and how can they play together?

Cause I keep hearing account-based marketing and all this other shit. And it's just like, really, I have, I really have yet to see a company crush account-based marketing the way it's supposed, like the way it's painted on a, on a picture. Right. You know, being super authentic, being very direct, only serving up information that's direct. I mean, the only, the only people that do true account-based marketing, Facebook, Google, Amazon, right. Because they know everything that I do and they're serving me up shit. And I'm like, yeah, actually I want that. I didn't even know that was a thing. Give me that. Right. That's account-based marketing that I've seen, but I haven't seen a B2B do it really well.

So how do you see the intersection of, of sales engagement tools and marketing automation working together in the, in the world moving forward? Yeah. I mean, quite frankly, I, I'm a big, I was a big early fan of marketing automation. I started sales off in the part on offices. Um, but I will say that my personal and our business use of marketing automation has just gone like this. Um, to where now it is relegated to, um, some landing pages, some, um, opt in subscriber communities that receive a newsletter and that's it. That's marketing automation. Now account-based a little different, uh, account-based is interesting because it's like, it's a way of life, but it's not a category of, of products or have you looked at the account-based marketing quadrant and you're like, hold on, that's apples and trucks and rocket ships and chairs.

You know, they don't do the same thing, but what we've done from an account-based perspective and it's all mapped out in our personal sales loft account is we, first we say, okay, who are the targets? Who are the target accounts? And we use all sorts of data and intelligence and information to say, here they are, you know, here's the, here's the, um, commercial market accounts. Here's the enterprise accounts. Then what we do is we say, okay, here's how we're going to distribute those to all of the AEs, not just the SDRs, the AEs first. And then SDRs are assigned to those accounts as well. So now you've got teams working accounts with playbooks and game plans of how they're communicating with them.

And then marketing is bucketing those accounts in certain segments so they can run campaigns to them. And so that's the way it works. And, and we, we home grew some software, you know, Jeremy Donovan, uh, that name he's, he's with us and he runs our New York office and our sales strategy. He built software from scratch that looks at every target account in the universe and identifies the ones that are right for us with like this 27 point inspection. And then it distributes all of those to each and every rep so that each rep gets an equal opportunity in their target account list. And, uh, and then we just monitor it as it goes through sales loft. Awesome. Awesome, man. Well, like I said, I think you and I could have this conversation for, for, and we do when we get together.

So we're going to cut it off a little bit. That's true. And, uh, three weeks and counting, man. Can't wait to have, see, see your sessions and have you in town. Me too. And so actually that was, that was my question. That was my final question. Like, what are you most fired up for about Rainmaker? Colin O'Brady. Colin O'Brady. Yeah. This guy, I mean, he, he, he was in Thailand, um, had a bad fire incident, burned up his legs. The doctors told him he never would walk two and a half years later. He won the Chicago triathlon. A few years after that, he became the first human being to scale the top peak in every single continent in the fastest period of time. And then two years after that, he just got back from Antarctica where he went coast to coast, Antarctica, 53 days, unaided, unassisted solo, dragging a 350 pound sled of his food and, uh, in this minus 60 degree blizzards.

And on the very last 80 miles of this trip, he'd been doing about 20 miles a day. And the last 80 miles, he decided to pack it all in and 48 hours straight finished just one straight run, uh, 80 miles and got to the finish line. There's no one there and celebrating because it's Antarctica. Oh yeah. I mean, shit, you know, to a certain degree, that makes me feel bad about myself. It's like a loser compared to somebody like that, like shit. But, but I think it does go to, to the, you know, the mental toughness. And, and so I'm assuming that's the connection here. Like you just got through, right? Well, believe it in yourself is everything, right? So sales is all about a fundamental belief in yourself and your offering and your company and transferring that belief to someone else.

I know you and I talk about that. And, and, uh, you know, if you believe that you can make it across the Antarctic, you got to have it. And by the way, right after I talked to Colin, I was in the kitchen at sales loft and some guy came in and someone asked him how he's doing it. He's like, uh, a little tired. And then he goes, well, what's happening? He's like, man, I've been working. We had partners in town for two days straight and I worked late. And I'm like, really? Well, it's funny you say that. Cause I was just at a sales kickoff recently where the guy ahead of me. So it was a two day thing. I came into my training on day two, day one was motivational speaker. And it was a, it was a Navy seal who had literally gotten his face blown off.

Like I did, boom, blew his face off and they reconstructed it and everything else. And he's up there and he's like, so, and he starts, he goes like this. He goes, who in here has had a bad day? And you know, everybody raises their hand. Yeah, we've all had bad days. Like I'm calling bullshit on every single one of you. And he was like, you want to hear bad day? And he goes ahead and explains like what happens to him. And afterwards you're like, yeah, okay. All right. Like the worst day of my life is it doesn't hold a candle to something. It's like 30 seconds of his day. I think that, you know, just gets all in perspective. Right. So anyways, Kyle, awesome, man. Good times as always. And I can't wait for Rainmaker, man.

It's going to be fire. So again, we're going to put this out there. I'll put a discount code that everybody can jump on board. I'm going to put some resources as far as your sales development study that you put out there as well. But anything else you want people to know about before we take off here? Hey, you know, just keep watching this podcast and stay in tune to John Barrows. You know, I've learned a ton of skills from you, John. And if it wasn't for the things you've been doing in the market, we wouldn't have built this company how it is. So I'm just so appreciative and deeply grateful for you and grateful for this audience for hearing us out. Awesome, brother. I appreciate it. Well, I will see you.

And by the way, thanks for that. By the way, my wife's still those tangerines, man. Bananas. And thank you for helping out my daughter with her Girl Scout cookie sales, man. I really appreciate it. Oh, awesome. Well, it's our pleasure. See you, John. Good to see you in a couple of weeks. I hope you enjoyed that episode as much as I did. And I really hope to see you at Rainmaker March 11th through the 13th. Get 50% off your tickets with VIP code JBVIP. Make it happen. Bye. Bye. Bye. Bye. Bye.