133: Barriers To Successful Prospecting With Matt Green

Thank you to our sponsors, LeadIQ, Costello, SalesLoft, WorkRamp, and Dialpad for helping us produce this podcast. Head over to jbarrows.com slash blog for the highlights of this episode and explore resources you can use right away. Let's make it happen. Good afternoon, everybody. This is John Barrows. Make it happen Mondays. Hopefully you all had a fantastic weekend. I am here with an awesome guest. He's a great partner I've been working with for a while, and he's got a really interesting perspective because he's working with a whole bunch of cool companies that we're working with as well and actually introducing us to a lot of them, so I want to thank him for that. But Matt Green, CRO over at SalesAssembly.

How are you doing today, buddy? You know, I'm good. My 2020 resolution was to be on this podcast, so I made it in 11 months early, so I'm living the dream right now. There you go. You can pack it up now, right? Yeah. I wish I had achieved all my goals in the first month. I've been looking forward to this conversation for a lot of reasons. First of all, our partnership, like we just talked about, has been huge for us as an organization, and watching the Chicago scene explode from a tech standpoint has just been pretty impressive. So do you want to give people some insights on what is SalesAssembly? Why did you start it and all that other stuff, and what's going on with it? Yeah, absolutely. So SalesAssembly, we are just about to turn three years old.

Based here in Chicago, what we are is we're a community of, as of this morning, around 126 Chicago's most prominent B2B technology companies. And the way that we work is we're kind of like an association. So we have companies that are all B2B tech. We don't with B2C or service providers, companies that are born and bred here in Chicago, such as Sprout Social, G2, ActiveCampaign, but also larger companies that might be based elsewhere, but have a big sales and marketing presence here in Chicago, such as LinkedIn, Upwork, Glassdoor, Intercom, so on and so forth. And what we provide to these organizations is we built a really strong community between the VPNC-level sales leaders, VPNC-level marketing leaders, and the VPNC-level customer success leaders.

We built a community for them where they could get together both in person and virtually and exchange best practices, compensation plans, ideas, simply because they're all building the same thing right next to each other. And we've also built communities for their respective teams. And we provide, through 70 in-person events throughout the course of the year, we provide ongoing training, education, and development for the sales, marketing, and customer success teams of all these companies. And the reason why we launched Sales Assembly a little less than three years ago is we saw this need. We ran into all these VPNC-level sales leaders that were all selling different products to different people.

But we all understood that if you're building a fast-growing B2B tech sales organization, you may be selling different products to different people. But when you check under the hood and you look at how you do it, a whole ton of consistencies. And nobody was sort of mixing and matching this crowd and providing them a forum to collaborate on all these shared consistencies. And that's what we did. And we're three years into it. And we're fortunate enough to have great partnerships with folks and organizations like yourself. And things are going really well. I love it, man. Yeah, it's funny. You know, everybody says, oh, we're different, right? But when you peel back, it's the same shit. And a lot of the fundamentals, too, are I don't care what you sell.

The fundamentals and the structure are pretty similar across the board, at least I've seen. I mean, yes, there's tweaks and there's nuances of ICPs and all that other stuff. But at the end of the day, a lot of blocking and tackling is pretty similar across industries, right? Exactly. And, you know, that is a lot of what we focus on. If you're a BDR, SDR in any organization, being great at developing buyer personas and effective negotiation tactics, that's going to be essential. If you are a VP-level customer success leader at any one of these organizations, knowing how to onboard CSMs more effectively, knowing how to forecast churn, that's going to be important. Whether you're selling into HR, whether you're selling into finance, regardless of what you sell, who you sell it to, all that good stuff is critical to building one of these fast-growing B2B sales organizations.

And that is the kind of stuff that Sales Assembly focuses on from day to day. And I think, in large part, one of the reasons why we've had so much success over the past three years is because we've been maniacally focused on only serving this niche, which is Chicago, B2B, Texas. And actually, I know kind of the topic we're going to talk about today is removing barriers for successful prospecting. But I did want to chime in on this community thing first because we're seeing – my eyes got opened when Outreach bought Sales Hacker, right? Because Sales Hacker was doing a really good job building a community and all of a sudden – and all of a sudden, Outreach purchased them. I was like, whoa, whoa, whoa, whoa, what?

And my perception of that – and I've talked to a few people – my perception was I think Outreach looked at it and said, hey, let's look at our marketing budget over the next five or six years and see if we can build a community. And we're not going to be able to build something like Sales Hacker built, so why don't we just buy it, right? Which really highlighted to me the importance of communities. And now we're seeing a whole host of organizations, organizations and companies specifically, trying to create this community because once they create a community, they can obviously have influence on that community. But I'm seeing so many of them fail so hard. Like they're saying, okay, we're going to build this platform and we're going to get all this content in there.

And John, we want your content in there. And we're going to do all this other stuff. And nobody comes. You know, the whole build it and they will come thing isn't happening with these communities. So I'm going to dovetail into prospecting for a second on this community piece because I do think there's a big piece of prospecting as it relates to this. But what do you think is – why do you think so many people are failing at creating communities? And what are the key components of a successful, engaged community? Yeah, that is – that's a fantastic question. From my perspective, if I could pinpoint one reason why communities fail, it is more often than not following the money rather than following the intention behind the community in the first place.

And unless, of course, you are running a nonprofit, which to be clear, Sales Assembly is not, it's easy to get sucked into, okay, well, this sponsor wants to talk about. This, this funder wants to talk about that. They're writing the checks. So we need to make sure that we're accommodating them. You know, again, I think where that, you know, not only do you have a good amount of issues that come along with that, but it ends up in this weird sort of split focus. You know, where I think organizations have had success and, you know, I'm proud to, you know, to say that Sales Assembly is – at least so far in the past three years, one of these organizations is, as I mentioned before, not deviating from our niche.

You know, we have had opportunities over the past three years to begin accepting service providers in our community. You know, we get reached out to every week by law firms, by consulting firms and say, hey, you know, we'd love it if you could teach our business development reps how to sell. And on the one hand, sure, sales is sales, but one of the reasons why Sales Assembly in and of itself has become so effective, the fact that we only allow B2B tech organizations that have a presence here in Chicago to become members and participate is because, number one, we want everybody to make sure that they're all speaking the same language, right? And, number two, an extension of that, we are extremely diligent in not only making sure that we're curating specific types of rooms.

If we do 70 events throughout the course of any given year, and again, all these events are done live and in person, each event is targeted to a very specific role or responsibility within the revenue organization. So, if we say we are filling a room with VPNC-level marketing leaders, that's what that room is going to be filled with, and that's who the content that we're presenting in that room is going to be relevant to, and that's going to apply to any other job description, role, or responsibility within the revenue organizations. And then, you know, the third thing I think is just the, you know, the tendency to let content become stale. Where my partner Jeff and I, where we spend more time than we probably care to admit, is making sure that we are keeping our ear to the ground in the community, meeting with our members, digesting problems and issues that they're facing, and then synthesizing those issues across the entire community, and turning that into new resources, content, and in many cases, event series, that we begin to roll out to the community.

Because our presumption is, is that if we talk to 10 VPs of sales, and we get the inclination that eight out of 10 of them are struggling with one thing, if eight of them are struggling with one thing, it's probably 80 of them, you know, if we're going to peel the onion back. So, that's really, again, that maniacal focus on targeting our niche, not deviating from that, and making sure that the content is always one or two steps ahead of the game, essentially. I love it. Yeah, and I think that the focus factor, I don't think could, could be understated. You know, I see these communities like, oh, here's a, we're building a community for sales reps to share best practices. It's like, really? You know what I mean?

Like, but if, but if it's like, no, for this specific niche, this is where, because that's where the engagement happens, right? Because if I don't come in, and I don't, and, and, and to a community, and it doesn't speak my language right out of the gate, as far as what my challenges are, I might sign up for it. But the likelihood of me actually engaging with it and coming back to it is not high at all, right? Exactly. All right. So, so, so let's talk, you know, about, let's, because we're going to talk about prospecting here is like kind of trying to stay that one step ahead, right? I always, we were talking before we got on here, it's like, that's all what I'm trying to do is I'm, I'm just trying to stay literally like a half a step ahead of what's going on right now to share that with other people, to help other people out.

That's why I'm constantly trying out new things. Um, and community is an interesting angle on that, right? Which is there, there's a, there's a way to leverage kind of this multi-channel approach, email, phone, obviously social selling and all those other different things and, and networking, but also engaging with communities. I'm seeing a lot of, you know, we used to have the LinkedIn communities where you could kind of go in and, and at least get the pulse of what's happening for, for that specific niche or whatever it was. Um, I always did, I always recommend against like prospecting into those communities, you know, when somebody posts a question and being like, oh, I can solve that and I can sell you something.

I think that's a super cheesy way to destroy a community. Um, but, but there's a lot of Intel there and now I'm seeing Slack, right? So there's these Slack communities for VPs of sales, Slack communities for CIOs and that type of stuff and getting engaged with those. How, if you're a, let's talk about it from a sales rep standpoint, right? Cause I think we can take the leadership approach to this or, and both, and the, and the executioner approach to this. If, if you're a sales rep right now trying to figure out like how to, you know, obviously you're doing your cadences, you're, you're, you're banging that stuff out. But you're looking at this community thing saying, man, there's a, look at sales, like look at sales assembly, for instance, holy shit.

Like there's some tech companies in there that I would love to sell to. And I want to get involved in this community. What would be the approach that they, they would take to that community or even an executive take in that community to get, to get value out of it, obviously to learn, but also to, to find ways of engaging and hopefully finding business. Yeah, that, that's a great question. If I'm looking to, for the lack of a better term, and I mean this in the best way possible, exploit a community that, that already exists. My, my thought process in this, you know, extends not only to how I would engage with a community, but how I engage with anybody that I meet throughout the course of any given day is always leading with, okay, what, what kind of value.

Am I going to be able to provide here, right? If this is a community of HR leaders, and I happen to be a sales rep at a company that happens to sell a product into HR, to your point a moment ago, I mean, the absolute last thing that you want to do is just occasionally pop your head up and say, hey, I saw someone mention this problem. Just so happens my, my product solves it. That's not, that's not, that's not what's interesting to the community itself that's, you know, not going to lead to any level of success at all. But if you, as let's say a sales rep, join a community, and focus on providing value, whether that's content or white papers, I mean, any sort of thought leadership that it might not even be your firm, your company is generating.

But you know, if you have a handle on this audience, and you're able to say, hey, I noticed you're talking about this, has nothing to do with, you know, my particular product or service. But I noticed this white paper over here, I think that this really answers your question. I think that's, I'm sorry to interrupt, but I think that's the thing that a lot of kids struggle with, especially younger ones, right? And I'm trying to think back, like, when I was first, you know, 20, whatever years ago, I'm not going to admit it, but, you know, the whole social selling and thought leader thing, like, that wasn't, that wasn't a thing, right? It was just know your product, go out there, sell it, have a conversation with people about it.

But now this whole idea of thought leaders, right, and adding value to a community or even adding value to a client, right? You know, I talk a lot about when you put together your cadences, think about not just all, you know, the Gary Vee book, right? Jab, jab, jab, right hook, like add value, add value, add value, then ask. And so, but then like, you know, who am I as a 23-year-old kid to add value, you know, and how do I add value, right? Because I think that's the thing I, a lot of kids are struggling with the most, which is, I don't want to come off as a pompous ass saying, I know something that I don't, right? So, so what would your approach be to a kid who's like, yeah, look, I get it.

I need to be a thought leader. I want to add value to these communities. I want to add value to my prospects that I'm reaching out to, but I'm 22 years old, I'm 23 years, I'm fresh out of college, or I've been in an industry for a while, and I don't really know a ton of stuff, because I've really just been focused on selling for the majority of my career. Like, how do you start making that switch to adding value in a way that is substantive and isn't thinly veiled, I'm trying to add value so I get noticed, so I can actually end up selling you something? Yeah, you know, of course, to answer this question, let's all operate under the presumption that every sales rep is going to be fortunate enough to work within a company where, let's say, they have one or even a staff of people that's generating good content and good thought leadership that could be disseminated on a day-to-day basis.

You know, I would recommend, you know, this theoretical sales rep not getting caught in the trap that it has to be their opinion, that they have to be, you know, the de facto subject matter expert, especially with, you know, if we're going back to the sense of community, I mean, a big part of what makes a community successful is oftentimes can't just be pointing people in the right direction, right? So as long as you are taking an active interest in the industry that you're selling into and the personas that you are spending your days reaching out to and having a conversation with, which, in my opinion, and we could talk about the differences and the nuances between if you're selling in a mid-market enterprise and SMB and the length of the sales cycles and the length of, or I'm sorry, I should say the amount of effort, if you want to call it that, that goes into building and maintaining and managing those types of prospect and client relationships, there's absolutely no reason whatsoever why a junior sales rep, the moment that he or she starts within their organization, and they shouldn't do whatever they can to get immersed, get immersed in the language, get immersed into communities that they exist if they do, and then leverage that immersement to say, hey, you know what, it's not going to take you long to realize, here's our, here are a couple outlets that, as it relates to questions that may come up around HR and benefits, and I'm selling into HR going back to that example, you know, here is the Sherm website, here are companies like Bravely or Blueboard or Jellyvision that are selling into this space that I know are generating really great content.

And if I see questions come up that are in any way halfway relevant, just pointing people in the right direction, and not, you know, not presenting as though this opinion is of, is your own, but just calling it out like, hey, I saw this, I thought of you. Simple as that. You know, I think that this might be helpful. Yeah, and I think, you know, I also think that asking the right question adds value in the sense that when somebody else posts a question, or when there's a thread going on there, and you can chime in on that, I mean, I just look at that from my perspective is when, you know, there's, there's when I post something on LinkedIn, obviously, there's a bunch of people come in, and they give their comments and their feedback or whatever.

But then there's, you know, I actually the ones I pay attention to the most are that kid who reads it, and has a an insightful, thoughtful follow up question on it, to say, john, I appreciate what you said here. But here's the scenario I'm faced with. And what about that? Like, do you have? Because that is like, yeah, like, I want to help that, you know, I want to help that kid, like all the other feedback. And you know, those are all good tips for people to learn and get themselves educated from. But the engagement factor, I think is the highest. And I translate that also to, you know, it's kind of like challenger sale, right? I got myself in trouble a while back, because I stood up on a stage.

And, and I was like, could y'all do me a favor and stop teaching 22 year old kids how to be a challenger, please? You know what I mean? Like, shit, I mean, you have to have some sort of business acumen to be able to put, you know, legitimately challenge, you know what I mean? Like, I think you and I after doing this for I mean, selling you and I selling to VPs of sales or CROs, you know what I mean? Like, I think if there was an uneducated CRO or VP of sales out there, both of us after 20 some odd years of selling, we could push back and I could say, hey, Matt, look, I appreciate the way you're looking at that man. But here's, here's what I'm thinking, you know what I mean? And it can come off.

But if you're 22, like cut the shit, right? But the way I think you can challenge as a kid, if you will, is by asking very thoughtful questions, like very, like impact oriented and thoughtful questions to get me to pause and think for a second. Because if you can get me to pause and think, here's my whole philosophy, or at least my experience is, if I can get you to think like if you and I are having a sales, if you're in my sales cycle right now, or I'm prospecting into you, and I fire you off an email, or I leave you a voicemail or something like that with a, instead of my awesome value proposition of how great I am, I ask you a very pointed question of, hey, Matt, as a CRO, you know what, one of the questions I'm asking is, is how do, how do you combine sales, marketing and customer success right now to really hit the revenue numbers?

And how do you make sure that they're all aligned? So they're all speaking the same language as you move into the new year with the challenges that you're faced with, like something like that. To get you to like, or have you been doing like, to get you to think for a second? So I think that's a, like some, it's an underrated thing that I don't think most reps take advantage of. Yeah. And I mean, it ties into something that, that personally, I still don't see. And, you know, you could offer your perspective, of course, a lot of reps taking advantage of in general, which is, you know, just to that point, I mean, doing what, before you make that type of outreach, doing the research. And, you know, finding, you know, comments or finding blog posts, you know, if you are going back to that VP of sales or CRO example, finding something meaningful of content that they've distributed that you could not necessarily push back on, but again, ask one of those types of meaningful questions, right?

And even if it's at a very high sort of tertiary level, you know, I had somebody in my network, the sales rep had success the other week reaching out to the president of a company that's high on his prospect list. And, you know, honest to God, all it took him was seven minutes of looking through his LinkedIn profile. Like, hey, I saw that he started here, that the president of the company started here X many years ago as an account manager, right? I'm an account executive, I want to grow my career, would love to talk to this guy about what that journey was. I mean, what did that look like? I mean, is there anything that I as someone who, you know, is him if you hit the rewind button 20 years, what am I going to be able to learn from that?

Here's what I'm doing now to your point, asking some of those tactical questions. Do you think I'm on the right track or am I thinking about this a different way? So, yeah, I completely agree and sorry to go off on a tangent, which I've been known. A lot of it does come back to just, especially in this age where you do have automation, where you do have, you know, a limitless number of technology tools that can alleviate the bandwidth of doing all these manual tasks that folks like you and I, when we were, you know, coming up in the business, you know, you mentioned 20 years ago, you must have started when you were 10 because you look great, John, all that stuff. You know, we don't have to do anymore.

The sales reps of today don't have to do anymore, which just frees up so much more time to be a little bit more thoughtful and intentional in their outreach approach. You'd think and you'd hope, but unfortunately, it's not the case, right? So let's transition because I think that's a good transition in automation, right? And where, in your opinion, do you see automation fitting for sales, not for marketing, for sales, like for those sales reps? And let's talk SDRs, BDRs, but I also want to talk AEs because I'm seeing, you know, the cadence tools, right? The outreaches, the sales lofts, all that stuff. Like, look, when those tools are used the right way, I think they're fantastic, okay? But most reps are using them as automation tools.

And so I'm wondering, from your perspective on the companies that you work with, as a sales rep, where does automation, like, let's talk SDR, BDR, the prospecting component of this. Where does automation fit, in your opinion? Where does it make sense? And where is it misused? Yeah, and I always look at this and I hit the rewind button in my mind about 18 months when there were a lot of discussions around, is automation going to replace sales? And, you know, maybe, you know, people are, or sales people, I should say. And I'm sure that there are probably still some conversations along those lines going on on the fringes today. But I think that we've all agreed that, you know, that that is not going to happen, especially as the sales, sales has evolved to a point where, you know, you do need more and more of this human interaction, this intentional interaction that you mentioned before.

So, you know, where I see automation having the most success is, as I alluded to a couple moments ago, is really just clearing the playing field, you know, opening up all these swaths of time that the sales reps of five to 10 years ago did not have. And the question is, okay, well, what are you going to do with that time? You know, are you going to leverage this? Well, like what? But like what? Like, what are the things that are automated? Like, what are the things that are automated that are supposedly giving me this time back? Because everybody's saying, I'm so busy. But I think you're right. I think there's a component of this that, yeah, like we didn't have, you know, there's tools today that do address a lot of things that you and I used to do manually.

But what are some of those things that they should be doing to give me back that time? Yeah, I mean, a lot of it could be doing A-B testing at scale, for instance, you know, from an outreach and a messaging perspective. You know, if I'm, you know, if I'm sitting at a desk and, you know, a big part of my responsibility is sending, you know, cadence of, you know, dozens, if not hundreds of emails throughout the course of the day to a very specific ICP, leveraging automation to do that type of A-B testing at scale so that we can improve efficiencies in our outreach process. So this would be one example. Should you do that, though? So let's kind of take that as a good example, right? I mean, because I think obviously that's what's happening, right?

These kids are taking these tools and they're sending them out there and they're getting this volume up there. And unfortunately, I'm seeing some companies actually ratchet up the volume on outreach as opposed to come back down to, like, more quality side of the house. So I guess with that approach, like, where I think there's, to me, there's a certain ICP that makes sense for that. But should reps be automating that that much as far as the outreach is concerned? Because I'm starting to come back to, I'm starting to come back to, I don't know. I don't know where, and I think the answer is, yeah, it all depends on your ICP, right? But I'm looking at it saying, part of me says, you know what, screw all the automation, be personalized with everything you do and all that other stuff.

But the other part of me says, personalization isn't really the key anymore, like we were talking about. I think it's relevance. So yeah, maybe if you come up with a kick-ass relevant email and you can send it out to a bunch of people, but I guess, how does that differentiate us from marketing? Yeah, you know, that is a fantastic question. And I appreciate you trying to, or now trying to actually inserting a delineation between personalization and relevance. You know, maybe that's going to be one of the blockers on mine is I sort of, and I'm not saying it's the right way to look at it, but I sort of look at those two as, as one of the same, right? I mean, you can't be personal. See, I actually disagree.

I think it's, I think it's because, and here's, here's what I'm seeing. So, so you're seeing these, you know, I'm on the same page with you with, with AI, right? Like I legit, like five years ago, I was freaking the fuck out about it. I'm like, holy shit, Skynet is here. We're all screwed. Like what the world? You, John, though, you know that. Shit, man. I mean, I'd like, I don't want to be ignorant enough to think I'm that good to be replaced by something if I'm not paying attention, right? But, but that said, like, but now that, and, but now that I'm seeing these automation tools, these AI tools that are sending out these emails, what they're doing is they're personalizing. But they, they personalize and, you know, the stats of sales loft has, you know, the optimum on a personalization is 20%, blah, blah, blah.

And it's that first line, right? So it's that it's because I go by the AIDA attention, interest, desire, action. And if we just shred an email here, the subject line gets your attention. The first sentence tells me whether or not I'm interested and, and what am I interested in? I'm interested in me, right? So that then gets me to read the rest of your email where create desire. And that's where you can give me your value proposition. So that I factor, that first sentence, and what I'm seeing is these AI tools, what they'll go out, they'll, they'll grab something personalized about me, right? And, and they'll send me an email and say, Hey, John, I, uh, I see you're, you're in Boston. Uh, you, you've been to legal seafood recently.

And then they do this hard cut to this bullshit pitch that has nothing to do with what that personalization was. And to me, that's fake personalization. I'd rather get an automated email from somebody based on a timeliness event of, Hey, John, we're working with other, uh, uh, uh, CEOs of training organizations who are trying to figure out how to engage with their audience more effectively and re, you know, and get more dah, dah, dah, dah. Even though that's not a timely personalized thing, it's a targeted thing based on my persona, but it's not personalized. Cause they weren't like, John, I was on your website and I did a shitload of research. I'd rather have that email from a fucking automated robot all day long.

That is, Oh shit, that's relevant to me. Cause that's my role. Then some kid who's like, John, I see you went to the university of Maryland. Like, yay, let's go Terps. It's like, dude, fuck you. I've been, that was 25 years ago that I went to fucking college. And that has, that you actually hurt your chances of, of getting a call with me. If you do this bullshit, fake personalization stuff. Yeah. Yeah. No, I, and yeah, I, I have absolutely zero challenge to, to what you just said. I think that, you know, at least in my mind, it was sort of just a, a mixing or, or a, yeah, I'd say a, a mixing of the nomenclature. I mean, relevance, of course, at least in my opinion, in this day and age is always going to be key.

And I think that does tie back to, to some of the community components that we were talking about before. I mean, looking at the example that you just threw out, like, Hey, you know, we work with a lot of X, Y, Z, uh, professionals like yourself. And, you know, therefore here is something that, that we're confident is going to be relevant to you. I mean, I've actually, and again, not to take a step back to, to the community side, you know, I've seen a couple of companies, um, doing this really effectively from all different types of demographics. You know, there's a company that is based out of Indianapolis, uh, Meta CX, that that's building a really great rockstar community, uh, customer success leaders, uh, happens to be, you know, their, their ICP.

Um, but as opposed to going in there and as we're talking about before hitting them with, Hey, here's this messaging about why our product works. And Hey, uh, we have four LinkedIn connections. I'd love to connect it and learn more about your business. Um, they are hitting them with much more relevant messaging, but they're able to do so because they have invested the time to build and manage a community of CS leaders. And taking that a step further, I met with the CEO of a company, they do crisis management company based here in, uh, Chicago, I should say based in, uh, Belgium, I believe, but I have a big office here in Chicago. You know, they've been able to build a rockstar community, uh, chief communication officers of fortune 250, fortune 500 clients, right.

Um, to your point about not only Slack channels, they do have a dedicated Slack channel buildup where the CCOs, uh, brands such as coach and Ford motor company and Tesla are on there chatting with each other day to day about, Hey, here's how we handle these problems. Um, and as you could imagine folks from that particular company. Yeah, of course that they're hanging out in there. I mean, they are gathering all, all the relevant information that they will be able to, to leverage, uh, uh, appropriately when the time comes. But, um, you know, and I think this touches back on how leaders can support this community building that, that we touched on really briefly early in the conversation is, you know, just being supportive of whether it's them as their, as the organization as a whole, um, or the folks, the account executives, you know, the salespeople on the front lines themselves.

Of investing the time and the resources, which can be relatively minimal. It doesn't cost anything to, uh, to, to put together Slack group. Or if you know that a number of your prospects or clients live in the same geographical area to get their buy-in and send an email with five or six of them CC'd and saying, Hey, you all know each other. I know you all love trading best practices with each other. You probably don't know each other yet. Now you do really encourage. I encourage you to, to buy a cup of coffee and sit down and chat with each other. Right. Um, going back to the relevance and the intentionality, you know, I think that's something where. When we talk about what automation and AI now afford sales reps, the opportunity to do, it's going to be to spend more time doing that.

Yeah. And I, and I think that's where if, if, if done right, you know what I mean? With the right intention and with the right knowledge. Right. And I think this is, this goes back to where I don't think too many companies spend enough time educating sales reps on, on that real ICP. That ideal, that true. I think most of them, you know, the basic demographic stuff. They run a list on zoom info of like, Hey, I want to see every company in these industries, this size. And you know, this title go right. And there's your list where, where the nuances of the ICP matter so much. And, and I, and I see, I see the, and that to me, to me, that's where I think everybody needs to spend more time is what does a really good client?

What are the characteristics of what a really good client looks like for us? Because then once you figure out the client and then the persona within that client that really gets the most value out of your solutions, then you can start to educate yourself on those, those true personas in those two industries by reading, you know, by joining groups that are specific to them and just listening to their, what they're saying. By reading job descriptions of those people and looking at the KPIs that they're being held accountable to by simply doing a Google search for like thought leaders, you know, CIOs, healthcare, you know, priorities, thought leaders, whatever, and following some of them and just, just literally just consuming the content.

And, and you don't need to know everything. Like I look, is this like, for instance, CIO, right? I didn't go to school to be a CIO. I don't understand the day to day life of a CIO, but I want it. If I'm reaching out to CIOs, I want to know enough to be able to ask and not just say, tell me about your priorities, like something dumb like that, but being like, Hey, you know what? I was reading this article the other day. I was in this, I was in this chat group the other day with CIOs and one of the major themes of some of the challenges that they're dealing with in 2020 or X, Y, and Z. Are you facing the same challenges right there? Like that, just that slight shift in context around a question makes all the difference in the world when engaging with somebody.

Yeah. I mean, it's just like, um, you know, the, the similar thought process that we adhere towards asking for referrals. It's not that open-ended question. What is troubling you? Uh, but getting super, super specific about, Hey, you know, I know that this is troubling a lot of people like you. Um, what say you, you know, yay or nay? I mean, you know, is this pretty consistent with you? I mean, it's just about, you know, sort of closing the funnel down and not giving them too much room to have to maneuver within their mind. Like, okay. I mean, this is where talk, it's like, Oh no, you, you have actually done your research. I appreciate that to your point before. Um, and yeah, to answer your question, this is troubling me, but I, you know, also I'm also dealing with this, right?

And that may open up the opportunity. It sounds like you've been talking to a lot of people like me. I'm dealing with this right now. Have you heard that from anyone else? Or is it just me? Um, that's where you, as a, um, as a salesperson are put in a really powerful position where it's like, great. Now I know immediately I'm going to be able to add value to this prospect. And again, it may not have anything to do with, with the product or service that I'm selling. Um, but just them telling you, here is the, here's the chink in my armor. You know, here is what I need immediately right now. If you're able to deliver on that, which again, if you spend at least a half decent, halfway decent amount of time immersing yourself in the business, in the industry, uh, surrounding yourself with people that are probably a little bit smarter than you when it comes to, uh, the particulars of what demographic is dealing with, it should be relatively easy, uh, to pick up on that and deliver something that is going to provide immediately immediate value in a way that that person's going to remember.

Yeah. And, and you know, it, it drives me crazy. You know, I train a lot of companies who, you know, and the, and the proof that this is an issue, by the way, um, is that I train a ton of companies that sell technical solutions to technical people. Right. So CIOs, CTOs, that type of thing. And every time I sit in a class and I'm talking even with senior reps, I ask them, okay. And we start talking about this business acumen and understanding the personas that you're going after and all that other stuff. And I'll stop. I'll be like, yeah, just to kind of prove a point here. Uh, who in here knows the difference between a CTO and a CIO and it's crickets and I'm like, yeah. And like, you could tell everybody's like, uh, and I'm like, hold still, you all sell to CIOs, right?

You all sell to CTOs and you don't know the fucking difference between the two roles. Like, are you out of your fucking mind right now? And it's like, that just screams to me that, that business acumen is sorely lacking within organizations, with individuals. And I think it's, it's incumbent upon the organizations out there to help the reps, you know, learn about what these people get, like bring some customers in that, you know, are your persona talk, ask them questions, right. And, and, and share information with your employees about, Hey, by the way, here's a new article that just came out about what CIOs in healthcare right now are really dealing with in 2020. And, and some of the challenges that they're addressed with, you might want to read that article, uh, so that your next conversation with the CIO can be a little bit more pointed, right?

Yeah. And, you know, that brings up some, it's weird that we see it, you know, as companies continue to, to scale, you know, they go from C to series A, A to B, B to C, and they're staffing up, you know, dozens, if not hundreds of people, um, you know, when, when they're, when they have that opportunity at scale to serve a much larger swath of the population, at least from what I've noticed, um, not just here in Chicago, but in general, you sort of have this, uh, inverted curve where, uh, the, the more opportunity that the company has, the less and less time they spend on actual research and due diligence and intentionality behind the outreach, right? You know, if you're a CEO of a, of a Cedar series A stage company, you better believe that, that you're just consuming that type of knowledge, uh, about your industry, um, speaking the language all day long and like, yeah, you're bringing in customer stories.

You're staying close to, uh, to the customer. Um, I've seen a number of CEOs of again, A and B stage companies who have a lot of respect for flying around the country, doing nothing other than just chatting with customers, you know, Hey, how's it going? You know, I'm not trying to upsell you on anything. Just what are we doing? Right. What can we do? What can we be doing better? Um, and you know, not, not keeping that type of scrappy mentality, you know, just because you've hired 10, 15, uh, sales reps, you know, BDRs and AEs, okay, well, yeah, I mean the, the customer feedback and staying close to what they're saying and what they're troubled with, uh, what they're dealing with, what they're struggling with, suggesting that that is not important or critical to the future success of your business anymore.

Personally, I think that's a, that's a big mess. Yeah. It's a huge mess is to get away from, from the client and the feedback and those type of thing. I mean, that's why I'm, I'm super psyched. You know, we, we hired a director of customer success, uh, in December and I couldn't be more thrilled to, cause she's now I'm introducing to her, all our clients and she's to get up to speed. She's talking to them about why they purchased our training, what they do with it. What do they like about it? What do they not like about it? You know, what would they have liked to see different from us? And I mean, the insight that she's gaining from these conversations is bananas and it's, it's reshaping our approach.

I mean, it really is. It's like, okay, cool. This is what our clients are telling us. And, and if you are not listening to that as a leader, uh, and, and you, and as a sales rep, I mean, I, I think, I think it to onboarding, I think onboarding for reps should be so much more customer centric than, than product centric as far as, you know, interviewing customers, reading through case studies, understanding why people bought from them, uh, you know, learning those stories, because that is such an easier conversation. Like once you, once you have the, first of all, that gets you to believe in your company, right? Like if you really start to dig into your customers and why they bought from you and the value they get out of it, that internalizes a lot of, wow, holy shit, we make a real good, you know, we make a real difference for the right client.

So that transfers that enthusiasm when you start talking, but then it just leads to better stories, better conversations, better questions. So I just, I don't know, you know, why more, more companies don't focus on, on that piece of the equation as opposed to product dump, memorize all this shit and go and learn how to pitch the slide deck, which nobody cares about. I, you know, unfortunately not everyone's as smart as you, so we've got to change that. We've got to get you in front of more and more of these companies and the, you can get them up to speed. Yeah. I always tell you, man, I'm a state school kid. I drank my way through college. I'm just, uh, I, I, I think the, I think the lack of being, uh, you know, knowing that I wasn't the smartest kid in the room is actually, uh, served me quite well over the years.

Right. Because I'm, I'm always genuinely curious about stuff to your point of people who are smarter than me. You know what I mean? Like I never pretend like I know what the fuck I'm talking about. I just want to ask you some questions and learn. I mean, that's actually one of the reasons I started this podcast, um, is because this is how I learn, you know what I mean? Like different people learn different ways. Like a lot of people are all books and yay and all that other, like I, I honestly, and I say this all the time, I've read less than 10 books in my life, like cover to cover. I've read less than 10 books in my life because when I read, I genuinely fall asleep. I literally like, it's something in my brain, five pages in, it says, see you later.

Good night. This is how I learned. I learned by getting people who are smarter than me on and having a conversation with them. And, and I think if more people kind of took that approach of the genuine curiosity to their clients, to their clients with some context, right? Not just saying, Hey, tell me about your business or tell me about your priorities. Right. But doing a little bit of homework beforehand would, would serve them a lot better than learning how to pitch their shit. Yeah. Yeah. No, I, uh, yeah, we, we could, we could go down a whole other rabbit hole about that. It's our particular mode of thinking. I agree. You know, I'm fortunate enough to, you know, built in and continuing to build a rockstar community here in Chicago with some really phenomenal sales, marketing, customer success leaders.

And, um, that is my excuse for when people ask me what I'm reading. I mean, it's always, you know, history in some way, shape or form, but, you know, I try to explain to people when, when they ask, well, how, you know, how come you haven't read, you know, this sales book or that sales book and I'm reading every day. I mean, I, you know, I do 20 meetings a week with heads of sales, heads of marketing, heads of CS here in Chicago. Um, and to your point, I'm just in there, I'm like, what are you doing? I, I, I ask questions and, you know, from that, whether it's through osmosis or, you know, just, um, you know, just the sheer volume of feedback that I get from these leaders in the community. I mean, that is at least in my mind, the equivalent of reading a book a day.

Last question for you. Cause I, I did, like you said, I think we could go down 50 different rabbit holes with this conversation, but the, the, I'm always interested in this one. Like, do you think you can teach genuine curiosity or do you think that's something that, that you just, that, that you, because, cause I, cause I, I've just been, and the reason I ask is because I, like, I've always been a, just a genuinely curious person. Um, and I've never, again, I, and again, think because I, I know I'm not the smartest kid that I've never felt like, Oh, let me tell you how smart I am and tell you I'm more of the, Hey, let me ask like, that seems interesting. Tell me more about that. Do you, can you teach that?

Or is that an inherent trait? I, if I had a gun to my head, which, um, uh, fortunately you're, you're not pointing at anything at me right now, at least through the video. Um, I would opt to say that, that you have to be born with that level of curiosity. Now that being said, I think that people can be motivated to be curious enough within a specific, um, you know, realm or idea of something that they know is going to be relevant to their success. But I think that's going to be inherently motivated by, well, Hey, unless I'm curious about this, I'm not going to be financially successful. I'm not going to be successful in my marriage, my relationship, you know, being a good parent. But I, I think, you know, and what I presume is that the type and the level and the intensity of curiosity that you're dealing with right now, or not dealing with it, that I would say you're, you're, you're blessed with, you're born with, um, it is something that, that you are truly born with.

I mean, there are people that, that are naturally curious and some people, I know a lot of them that, uh, don't really care about what anybody else has to say. Yeah. The me tours, right? Like the ones who are like, Oh yeah. The, or the one I call them the one uppers, right? Like, you know, somebody is telling you a story and you could just tell their itching to interrupt you and be like, well, you know, that's an interesting one. Cause about my story. And it's like, Oh, shut the fuck up. Let me tell you what that story that you're trying to explain to me. Let me tell you what that means about me personally. I mean, yeah, but that's a, that happens, uh, occasionally. Yeah. Occasionally shit that happened to you go to a social setting.

Yeah. Good to be, you're gonna be nice about it. I go into social settings all the time and I, I purposely sit back and watch interactions between people and how, because I've really started to pay attention to this. It's funny because I mean, everybody talks about storytelling, but if you really start to sit down and just get a group of your friends together and count next time you get a group of your friends together, okay, just, I'm talking, forget about business for a second, right? Count within an hour at dinner or something like that. Count the amount of stories that people tell. It is absolutely bananas that I'm, I'm finding that legitimately 75 to 80% of the conversation in general is about, it is somebody telling a story about something that has happened.

And, and it's, and there's, and, and then I watch the people who are telling the stories genuine and then the people who want to tell their stories on top of it and what that does to the dynamic of the person that told the first story, right? Cause the person tells the first story about, Oh, you know, check this out the other day. I was doing this and they were really hyped up about it. And then somebody jumps on top of it with another story. That's just that better than theirs or whatever it is. You can watch that person kind of seep back into their chair and remove themselves from the conversation because they're just like, okay, you know, apparently nobody gives a shit. Apparently your story is better than mine.

So I guess I'll shut up now. And it's, it's, it's a really interesting dynamic to watch. Yeah. That's funny. I mean, not, not to, you know, get too much into the realm of the personal, but, um, you know, my better half, my wife, she would tell you that, you know, when, when we go to, to social events, I mean, I'm, um, I've never been a big talker. I don't like talking about myself. Um, and, you know, at least in her mind, there's always this disconnect. I've never in my life worked in a job that was where my compensation in some way wasn't based on performance commission, um, you know, 99% of the time through, through sales. Um, but when we go to social events, I mean, I, I talk the least and it's just in my nature to, to your point, to sit back in and listen.

Um, and you know, I, you know, my wife sometimes can't wrap her head around, um, you know, how can you be sales, do sales all your life. But, you know, when people are trying to like, Hey Matt, you know, how's business going? I was like, yeah, it's going well, you know, we're, we're having fun. I mean, I don't want to like, Oh yeah. I mean, you know, here's all, all the cool things that we're doing. Let's make this conversation about me. I'm perfectly content more than content. I'm happy sitting back and listening, uh, to what is going on with everybody else. And I think that, you know, to the crux of your point in doing so and having been in a sense built that way, um, has made me, um, I'm not going to say a good sales person.

My partner, Jeff would say a terrible sales person, uh, but it's made me at least a marginally better sales person than it would have if I was built otherwise. Yeah. I'm the same way. Like people think I'm a massive extrovert because of, I stand up on stage and, you know, do these presentations. And it was funny, my wife, I brought her to a dream force one year and, you know, all the, you know, and I've trained, you know, thousands of people, right. And all these kids are coming up to my wife being like, Oh man, like, how do you deal, you know, you're John's wife. Like, how do you deal with his energy and dah, dah, dah, dah. And she's, she literally just starts laughing. She's like, excuse me.

She's like his energy. Uh, he's a, like, I'm, I'm, I'm about as mellow as it gets. Right. I'm a stoner. I sit on my couch at home. You know what I mean? I kind of, I sit back in the corner for events if I, if I really don't have to, right. And she's the butterfly. She's the one who's running around talking to literally every single person at the party. And I'm, and she's got, she's, I mean, her passion is the 10 X times mine. And so she, she always finds it hysterical that everybody thinks I'm this like gregarious, like open, like in your face, you're like, dah, dah, dah, dah. And I'm like, nah, I'd rather be the guy in the corner. That's kind of observing what's going on right now, as opposed to the center of attention in any way, shape or form.

Yeah, no, you're, yeah, you're, you're, you're, you're describing a my life to T, but at least now, I mean, nothing else at the end of this podcast. I know that, uh, that John bears is a potential Netflix and show partner with, uh, with me on a Friday night all day, man, all day, all day is usually Friday afternoons or I go on Snapchat. If anybody ever wants to see it, they go on Snapchat or Instagram and I do the it's Friday. You ain't got no job. You ain't got shit to do. Light up the spliff and sit down and watch a movie. So, but, uh, awesome. Well, Matt, let's, let's finish it there. Um, look, how can people find out more about, uh, sales assembly and what you're doing? What's the, what's the best way to get in touch?

Yeah. Best way is, uh, sales assembly.com. Um, and I'm perfectly happy. I'm the type of person that, uh, I love connecting with pretty much everybody. I'm happy to share my, my email at sales assembly.com. Uh, would love to, uh, connect with anyone that wants to learn about all the good things that, uh, that we're doing here in Chicago. Perfect. I think there was a little blip there. Is it Matt at sales assembly.com? Oh yeah. So I'm sorry. Yeah. It's Matt M A T T at sales assembly.com. Cool. And you can find Matt on LinkedIn too at Matthew green. So M A T T H E W green. Right. Yeah. Um, and, uh, cool. All right, Matt. Well, thank you so much. Hopefully everybody got as much value out of this conversation as I did.

Um, you know, I, again, really appreciate the partnership and the intel out there. So, uh, as always, everybody, thank you for listening. Uh, have a great day. And like I always say, if, uh, if you, uh, no matter what you do today, if you can make somebody smile, you know, you had a good day. So go make somebody smile today. Cause there needs to be a little bit more positivity in this world. All right. So make it a great day. Let's make it happen. Everybody. Thank you all very much. Nice job. Nice job.