Founding Sales Assembly

Alex Kracov: So I'd love to start today's conversation with the founding story of Sales Assembly. I'd love to kind of start maybe with, like, what were you doing before Sales Assembly that led you to starting this company?

Matt Green: Yeah, well, thanks for asking. I mean, God, where to begin? Like a lot of things in a lot of people's lives, I presume, when you look back, there was just a lot of happenstance and a lot of coincidences that happened to bring you to where you are today. So I started my career in finance and wealth management. I worked for a little over a decade at big companies like JP Morgan, managing money for rich people. Eventually pivoted into working with small merchant banks and investment banks raising money for early-stage companies. In doing that, I met the CEO of an early-stage company here in Chicago. Long story short, I started doing business with them. I did enough business with them where I was one of their biggest clients during their early year after inception, and got to know the business so well and got to build such great relationships with the CEO after they raised their A round said, "Hey, why don't you come on board and lead sales over here?" So I did that. And one of the first things that I did is I hired a gentleman named Jeff, who I'd met serving on the board of the same charity, maybe about three or four years prior, to work on my team. So we were there building a sales teams cross country for this organization. Fast forward a year and a half, got impacted by a riff. We're like, crap, what do we do now? Right? So we were sort of faced with a decision point of, okay, do we go and find W2 roles for ourselves, or do we maybe see if we could kick around a few ideas and get something off the ground? So sort of on our own.

One of the things that have been happening over the past year or so throughout that time is, we have put together a really informal monthly coffee meeting that consisted of what at the time were the heads of sales of really early-stage Chicago tech companies. This was back in like 2015, 2016. Companies like G2 and SpotHero and Sprout Social and ActiveCampaign. We would come together as a group, because we're all building early-stage companies. We would chat with each other regarding what we're working on, what we're struggling with. It didn't take us long to realize that regardless of the products that these companies sold or who they were selling them to, all these leaders were always complaining about the exact same stuff. So my partner, Jeff, he had the idea of saying like, "Hey, why don't we start offering solutions to all these things that all these leaders and all these different companies keep complaining about?" And that eventually became what Sales Assembly is today. So we launched back in 2017. We've been doing this for a little bit over seven years now. So again, to my point before, just really sort of happenstance, coincidence, fell into something like this and just happened to hit on the right idea at the right time here in the Chicago tech community.

Alex Kracov: It's amazing how most careers turn out like that. I look back even on my own career, and it's hard. It's like when looking back, it all makes sense how it fits together. But when you're beginning your career, you think it's going to be this linear path, and this is going to perfectly lead to that. It's like this magical kind of coincidences that lead to things, especially when you're doing more entrepreneurial stuff like we are.

Matt Green: Yeah, or even taking a step further back, I studied criminal justice in school with the goal of going into the FBI when I graduated. You know, like a lot of other people, I presume, the day I graduated, I woke up, I'm like, "Well, crap. I don't really feel like doing this anymore." And again, I just happen to find myself in a completely different industry.

Alex Kracov: Totally. I thought I'd be a lawyer. My parents are lawyers, and I was going to go do that and, you know. I was like, "Wait. I don't actually want to be a lawyer. I want to do stuff online. That seems more fun and more interesting." So yeah. Alright. Going back to Sales Assembly, so you're doing these groups, these coffee meetups with the sales leaders in Chicago. Then you're like, you come with this idea of, "All right. I'm going to sell some solution towards them." What was that v1 solution, that kind of product, that you first went to market with?

Matt Green: Yeah, it was the epitome of the idea on the back of a napkin. The product that we were selling was, okay, we will still come together every month rather than just chat with each other. But what we'll also do is, we'll put together a quarterly breakfast exclusively for the VP and C-level sales leaders of Chicago B2B tech companies. We'll all come together for a nice breakfast, and we'll bring in a heavy-hitting speaker. Is it an entrepreneur, a VC, someone else from within the ecosystem that could provide some guidance and leadership? And that, in and of itself, would be our product. So what my partner, Jeff, did - again, he had the great idea. He was just putting this down on paper - he would be going around to sales leaders here in the Chicago tech community and saying like, "Hey, if we did this, would you pay for it?" Enough of them said yes. Where we said, "Okay. Great. There is something here." But it did really start out just as a community for collaboration for executive-level sales leaders of B2B software companies specifically that were here in Chicago. From there, it evolved into providing training for the BDRs, training for the AEs, and training for the post-sales teams over the next few years.

Alex Kracov: When you were still in that community, like that early community phase, and you launched it and you get some of these sales leaders, did it feel like there was immediate product market fit? Did it feel like it was immediately working, or was that a struggle to kind of figure out what do we want the content to be about? Yeah, what was that part of the journey like?

Matt Green: Fortunately, for us, at that time, there was this really significant need. There was this gap here in Chicago, where the Chicago tech ecosystem had had some recent successes. You know, Groupon being the biggest example. Right? So, you know, around that time, about a decade ago, outside of Silicon Valley, there were all these cities - New York, Chicago, Atlanta, Denver - that were all kind of vying for like, okay, well, who's going to be like the next sort of tier two tech ecosystem? There was a lot happening here in Chicago. We have a really amazing School of Engineering at the University of Illinois, which a lot of people don't know this, there are more engineers in Silicon Valley that have graduated from U of I than any other school in the US.

Alex Kracov: Marc Andreessen is one of them, right?

Matt Green: Exactly, yeah. So we had really great talent here. They traditionally would go elsewhere, but then they started saying like, okay, well, let's launch companies here in Chicago. So we were able to come up with this idea and market this idea just at this really amazing time where the ecosystem was on an upswing. But there was still no community or connectivity whatsoever within the ecosystem. So we did see a sort of immediate product-market fit. And enough so that we're able to take, what was at the time, a small collection of clients, maybe about 10 to 12. We actually go out to companies like Outreach and Gong and gather sponsorship dollars by saying, like, "Hey, look at this really cool community of revenue leaders that are your buyers that we're forming here in Chicago. Do you want to be a part of this?"

Alex Kracov: Makes sense. Then what was the decision like to kind of expand beyond just meetups, community and speaker, to do more formal training and workshops for not just the leaders themselves but I guess more of the end users, the people on the front lines: the BDRs, the AEs, the managers? What was that decision like, and what was that program like in the early days?

Matt Green: Yeah, it was all really just dependent on market feedback. Not only did we have the opportunity to sort of gather signals around what these leaders were struggling with via the monthly coffees or the quarterly breakfasts that we would do, but we also made it a point just to consistently ask. What else could we do to be helpful? What else could we do to add value? And there were enough leaders again that early on said, "Hey, I don't know if you could do this. But if you want to be helpful, my BDRs, they're really terrible about objection handling." It's like, "Okay. Well, what if we put together a training session just on this topic for BDRs?" So we started doing a monthly cadence, where every month we would go to Sprout Social's office, or LinkedIn's office, or Deloitte's office. They would offer up space for us, and we would just bring in, "Hey, every Sales Assembly member as part of the membership, now you could send two individuals from your teams every training session that we do." That's now an additional part of the product and service that we're offering. And it started with just training BDRs on objection handling, qualification, cold call openers, things like that. Once we were doing that for about six months, we started getting more feedback like, "Hey, can you do this for AEs and teach them some of the closing competencies." And again, it just continued to snowball. From there, more and more leaders saying, "Well, what about this job persona? What about this skill or competency?" And we just continued to react to what the market was asking for.

Alex Kracov: Were you and Jeff just doing these trainings yourself, or would you bring in other speakers? Were you kind of just making it up on the fly based off your own sales experience? How did that look?

Matt Green: God, no. I mean, we're not that evil that we would subject people to training delivered via Jeff or myself. No, we were fortunate enough to be able to develop relationships with other, if you want to call them partners or service providers in the space. So, for example, a really great partner for us and till this day remains so is a gentleman named Brian Bar that runs an organization called Victory Lap. What Victory Lap does is they take individuals maybe just out of school, have no sales experience, puts them through a three-month boot camp, teaches them how to be an effective BDR and then places them at tech companies across the ecosystem. So we would leverage our partnership with him. He would come in, and he would teach these BDRs around objection handling and things like that. Then from there, we started training more personas, whether it's AES, CSMs or frontline sales leaders. This is something that continues to this day. We were able to leverage just the relationships that we have with other revenue leaders from across the ecosystem. So a leader at Sprout Social would donate his or her time to lead a training session on a specific topic. A leader at LinkedIn would do the same thing, really just to be generous and to be a good contributor to this really tight-knit community that we had built here in the city.

Alex Kracov: I think that's what makes you so unique is that you have these real, true relationships with sales leaders and then bring them in to lead the trainings and the workshops and stuff. It's not just some, I don't know, random thought leader who thinks they know about sales, but it's like real practitioners who are actually helping leading the trainings. That's such a unique differentiator.

Matt Green: Yeah, thank you for saying that. I mean, we've always made it a point. And not that there is anything wrong with leveraging consultants or thought leaders to facilitate trainings. We've always found more success of leveraging and partnering with, to your point, existing operators - not only people that could say, "Hey, I did the job before and this is what I did," but more importantly could say, "I'm still doing the job today. I'm still leading a team today." And this is how we negotiate with procurement teams in Q3 of 2024 compared to Q3 of 2022. Wildly different. So it does give us the opportunity to instill more credibility and shows us importantly more relevance into the content that we're providing week in and week out throughout the year.

How to Build a Business off Relationships

Alex Kracov: It seems like you've built this whole business off of relationships. I mean, you've just been able to build really strong relationships within the sales community. What's the secret to doing that? How have you been able to go out in this community and just build such strong relationships with so many important people?

Matt Green: You know, it's an interesting question. I always feel uncomfortable saying anything relatively positive about myself. So I'm going to step outside of my comfort zone. You know, I think that as the person who's been primarily responsible for the business development and the sales over the past seven years, yeah, I like to think that I've done relatively well from a relationship building and expansion perspective, if you want to call it that. The secret, if there is one, as hokey as it sounds, is just caring, caring about the relationship. To that point, what I mean is everyone, including Sales Assembly. We have a CRM. We have HubSpot. It's not only gathering information around the traditional information that you might want about a deal or a prospect. But also, what are their kids' names? Where's the last place they went on vacation? What kind of wine do they like to drink? That is stuff that I am legitimately interested in. When I'm having a conversation with someone, these are going to be the types of things that I want to talk about.

I think, or I like to think, I hope, that my genuine interest in building a legitimate relationship with someone comes out and is apparent. Therefore, it makes it easier to build relationships with people. Especially, sales leaders, they could sort of smell through bullshit a mile away though. It's like, okay, well, yeah, I'm actually going to engage in a genuine relationship with this person. The downside, however, is that that's not super scalable. But for very relationship-driven sale organizations, we still are, even seven years after forming the company. To your point, how we've continued to grow has been predominantly based off relationships that we are able to form, rather than cold outbound or getting a whole lot of inbound and sort of the traditional go-to-market methods.

Alex Kracov: And your answer, I mean, it shines through. We've known each other for maybe a year or so. And I think, yeah, it's just like you come across as very authentic and you care. Not just come across. You are. You're authentic. You care. You're responsive. I can see how you've been able to kind of build all these relationships. I think one funny thing is me and Joey - like your LinkedIn profile picture is so different than, I think, your actual persona, which is very funny. I think of you as just a good salt to the earth, like good guy. Not that that picture is not, but it's more goofy, right? It's funny. So when I reached out to you - I think that's how we met. I forgot who reached out to who - I was like, oh, this is not exactly the person that I thought I'd be meeting with. It was honestly like a good, not a bait-and-switch, but a really good surprise. I think it was like, oh, this is not just an annoying sales bro. It's like, no, this is somebody who actually cares, wants to build relationship, wants to kind of go deep. I think, yeah, that's, I don't know, the funny thing about you.

Matt Green: Oh, thanks for saying that. I mean, they're full transparent. There is a bait-and-switch element to it. Mainly, it's because that picture was taken in 2015. You know, I've been on this earth 42 years. There's maybe three halfway decent photos of me in existence. That's one of them. So I'll be using that until I'm 65.

Alex Kracov: No, it's good for LinkedIn too. Yeah.

Matt Green: Yeah, exactly.

Monetizing a Community

Alex Kracov: So you're the CRO for Sales Assembly. How do you think about driving revenue growth for the business, monetizing the community? How do you think about your different revenue streams? Can you kind of walk us through that? And is it just you doing all of the revenue stuff? Do you have a team around you? Yeah, what does it look like to grow Sales Assembly?

Matt Green: So from a revenue team perspective on the new business side, it's primarily myself. My partner Jeff will chip in occasionally. We do have a dedicated CS team that, of course, does a great job managing all the client relationships once they become client relationships. Our revenue streams, fortunately, we run a very simple business. It's twofold. It is memberships, which is our core product. That is just the annual subscription in the Sales Assembly. And what they're getting in exchange - companies like G2 and ShipBob and Jellyvision and SpotHero - is predominantly the consistent access to the 300 to 400 live training programs that we're facilitating every year for their go-to-market team. Then layered on top of that is this community component that's kind of stayed with us throughout the seven years. The other channel, as alluded to earlier, is going to be sponsorships. We do have big companies like Gong, like Vidyard, like 6sense, whatever the case may be, that look at the demographic that we cater to and say like, "Hey, there's a great demographic. We want to make sure that we have visibility in front of." So we do have an additional revenue stream of sponsor dollars coming in that way. But it is predominantly, the core of our business is going to be the annual membership subscriptions that we provide to B2B software companies.

Building a Sales Training Program

Alex Kracov: I'd love to switch gears and talk a little bit about the actual content in the training programs. I'm sure it's evolved quite a bit from seven years ago. Can you talk about that evolution? Has it just been, okay, we're going to cover more and more topics that cover more and more parts of the sales process, or have the actual topics changed? Can you take us through kind of the content and sales training programming evolution over the last couple years?

Matt Green: Yeah, so up until about a year and a half ago, it was the very epitome of building the plane while it's in flight. We put on content that we thought at the time sounded good. It was like, "This would be useful. We're hearing enough people talking about this. And if our members are asking for it, let's go ahead and try to provide it." What that led to was us doing a whole lot of stuff for a whole lot of people. Some of it was really good. A lot of it wasn't really that great. But the good news is, we were caught in this upswing from 2020 to 2022 when, admittedly, like a lot of companies, didn't really matter the quality of our product to an extent. Because the ecosystem itself was grown so fast, we were able to kind of ride that wave. Enter 2023, little bit of a pullback. Then we were actually like, "Oh, crap. Our product is not nearly as good as we thought it was." We could see that because these companies that were long-time members are now starting to churn. And what's the reason that they're churning? You know, your content is good. It's not great. So we're like, okay, well, we got to really hunker down and start creating really amazing content.

The first thing that we did is, we got very narrow on our focus. Pre-2023 we provided training to not only AEs and BDRs but marketing leaders, RevOps, partnerships. Everybody that touched revenue, we're like, "Hey, we're going to provide some type of training for you." We realized pretty quickly that anything outside of individual contributors and frontline sales leadership wasn't really within our strike zone. So we got rid of all the training for marketing, RevOps, partnerships, all those other sort of tertiary job titles, if you want to call it that. And we got very narrowly focused again on providing training for BDRs, SDRs, AEs, CSMs, account managers, frontline sales leadership. And rather than providing what we would normally consider training for roles - here's an AE training. Here's a BDR training - we decided to make a big pivot and focus on training for skills, training for negotiation, training for value articulation, training for qualification, these skills and competencies that sometimes transcend role and job responsibility but, again, at the same time, are still going to be sort of required if you're in a go-to-market position in any B2B software company.

So when you take a look at the Sales Assembly product today, the curriculum that we're providing is, we provide certifications across two dozen different skills. How we're providing that is, five to seven times per week, we're facilitating live collaborative training sessions that tie in to be skills on things like discovery, or team selling, or driving urgency, or multithreading, just really tactical, actionable content that ICs can take and start implementing in their business straight away. So the way that we partner now with organizations is, if they have an enablement team, we just act as an extension of the enablement team so that the enablement team could focus on product training and product marketing. We could provide all the day-to-day skills training. If you're a smaller company that maybe doesn't have enablement infrastructure, then, essentially, we are your defacto enablement team until you're able to build one.

Alex Kracov: That is such an interesting and smart pivot into skills-based training. Because as you're talking about it, it's like it's so clear that these skills, like negotiation and multi-threading, it doesn't matter whether you're an AE, or a manager, or a CSM, or I'll say a even a founder. You got to get good at these things, right? I think even as I'm building Dock, I don't know, I always think of multithreading as, all right, I got to do it in the sales process and get to win the deal. But honestly, multithreading doesn't stop there. It's still happening as we want to make sure we have multiple champions at a company that we close and things like that. So yeah, it's a really smart positioning for your training and I think, very, very, very, very needed. Especially, if you make it to a role-based, then it can get too generic. And what am I actually learning? But the way you set it up is like a manager can be like, "Hey, one of my AEs is really bad at qualifying or really bad at negotiation. Go do one of those skill-based trainings." So, yeah, it's very, very smart how you've done that.

Matt Green: And to that point, that is how we do tend to work with our member companies. It's starting with the overarching business metrics that they want to impact. So if they're looking at their team of AEs, they're saying like, "Hey, we got these three AEs where sales cycle length is good, ACV is solid. But man, they're losing more deals than they should right now. We need to improve their win rates." Great. We have entire curriculums that are going to be built specifically to help them improve their win rates. That's how we're going to differ from a methodology, right? We're not here to institute a methodology or compete with Challenger or Sandler, or we're not even here to institute the sales process. We're just here to make your team more effective at executing whatever the sales process or methodology might be.

Alex Kracov: Yeah, that answered one of my questions. I was curious how you differentiate versus Sandler, winning by design, all these things. But yeah, it is very different. And at Lattice, yeah, I think what do we bring in? I think Sandler, yeah. I kind of keep track. Sandler, Medic, all these things. It's like, yeah, it was useful and it helped set us in a ready foot. But I don't know. I think you win deals by having good sales skills, to be honest. You're really good at qualifying. You're really good at building a business case with somebody, different things like that. That's ultimately what gets you across the line. Of course, you need to follow some of the things that those methodologies teach. But ultimately, it comes down to how good of a salesperson are you and so.

Matt Green: I mean, I completely agree of course. An analogy that I would pause it is, you know, think of if Dock is a basketball team. The methodology that you might adhere to is going to be part of the team's playbook. Where Sales Assembly comes in? We're the trainers. We're just making sure that people on your team are doing their push ups, their sit ups, running their laps day to day. Again, necessary regardless of whatever the playbook is. I'm probably going to make them more effective at executing whatever that playbook is anyway. So that's how we sort of operate in tandem, right? Sort of at a lower level than a methodology.

The Biggest Skill Gaps in Today's Sales Teams

Alex Kracov: Super complimentary to the methodologies as well. That's a great pitch, obviously. For enablement, it's like, oh, go do Sandler. Go do Medic, whatever. But we're going to come in here and be the trainers to make sure you actually execute on it. Smart. When you look at sales teams today in 2024, what are the biggest skill gaps that you see? Because, I mean, I think sales has obviously gone through this big transition over the last couple of years. There was the whole run up during Zurp in 2021, and I do think sales teams lost a little bit of their skills in kind of when it was easy to sell. And today there's a huge pressure on sales teams to deliver more with less. And so like, yeah, what are those big skill gaps that you're seeing on most sales teams today?

Matt Green: Two big ones that come up a lot. First and foremost is being able to sell through your champion or writer, or being able to sell through who might actually be the decision maker but not necessarily the economic buyer, right? I mean, we all know that most purchasing decisions right now are going to be made by committee. For instance, taking Sales Assembly, we sell to VPs of sales and CROs. In some cases, those individuals are going to be both the decision maker and the economic buyer. In a lot of cases, they're not. Economic buyer is going to be the CFO, that we're never going to even have the opportunity to get on a call with. So it's about having sort of two different conversations at the same time and prepping our champion, the decision maker - in this case, the VP of sales and CRO - to sell Sales Assembly when we're not in the room to do so. And do so in a way where we're still speaking to the needs and the pain points of our champion, but at the same time speaking to the larger business case that the CFO is going to need to justify in order to approve spend on this. So that type of sales approach. And if you want to consider the type of multithreading, you can. But I think it's about more selling through the decision maker. That's something that we see a lot of reps struggling with.

Another thing that we see a good amount of reps struggling with, and you sort of alluded to it a few moments ago as far as 2021 versus now or even taking a step a few years back to pre-COVID versus now. We're seeing that more and more organizations are finding value in getting their sales teams meeting the prospects in person. But at the same time, what we're seeing is that the sales reps have no experience doing things in person and, therefore, they're not equipped for it. I mean, there's a story that we heard earlier this year from one of our member companies that will forever stick with me. They were making a big push for their AEs and their CSMs to travel, get on site with their clients, build relationships in person. They weren't getting a whole lot of adoption, even though they're thrown a lot of budget and incentives and all that good stuff in order to try to push these folks to do so. At first, they thought like, okay, well, maybe our team is worried about work-life balance. They don't want to travel too much, all those standard things. But once they really drove a little bit deeper, they found out that there was just all of this anxiety amongst the ICs about just the idea of going out and trying to meet people in person. You want me to sit down at a dinner for 90 minutes with three or four people I've never met before? I mean, no, I'd do 25-minute Zoom conversations. Right? The not knowing that if you're going on site to a client meeting and the meeting is at 10 o'clock at the client's office, and you pull up Uber, you don't arrive at 9:55. You got to arrive like 20, 25 minutes early because there might be security, you got to check in, you got to get it up to the office. Be a few minutes early.

As weird as it might sound to people like you and me that have been selling for a long time, when you think of sales reps that started their career as SDRs or BDRs in 2018, 2019 and then started selling all throughout being AEs in 2020 up until now, it never had to do this kind of stuff in person, right? So it's like asking you to play a game of basketball. To use that as an analogy before, when you've never picked up a ball before, I mean, you're not going to be that great at it. And if we put you on the court against a whole lot of college players that have been doing this for 10, 15, 20 years, you're not going to fare that well. There's going to be a whole lot of anxiety about even stepping onto that court. So we have seen, as weird as it might sound, a pretty big gap there that a lot of organizations are looking to fill.

Alex Kracov: So interesting. I'm definitely out of practice of it, too, the in-person meeting. I mean, when I first moved to San Francisco, that's all I did. I would go down to Google and spend - I was a consultant for them, and I would spend all day in meetings and talking to customers and working on different projects and trying to sell and all these different things. Yeah, I mean, now we've just all spent so much time from the comfort behind our computer. And it's like, yeah, there is that anxiety that I still honestly have, where I'm like, oh, god. Okay. In person, this means a little bit different. I guess we're actually making the same push. It's funny I was laughing as you're talking. We want to go do more road shows, lunch and learns, both with our customers and prospects. Besides the logistics of - I totally agree with you - you got to show up early and be prepared and dress a little nicer, maybe show up with some pastries or something, what does it take to command the room? When you're in the room with a prospect, what makes that meeting different than when you're doing a Zoom meeting? Do you have any advice for sellers or CSMs?

Matt Green: Yeah, if I could recommend that they hone in and try to improve on one skill, it would be storytelling. When you talk about commanding a room, whoever is going to be the best storyteller in that room, he or she, they're going to have the greatest opportunity to command the attention in that room. I think that the storytelling just in general for - I like that you made that point for either AEs or CSMs. Just as critical for post-sales teams as well to be upskilled on a lot of these competencies, that might seem to them kind of salesy but are going to be effective, especially as organizations are asking their CSMs to become more commercially-minded. Or just think of how they engage with our clients in that way, definitely improving their storytelling and public-speaking abilities would be at the very top of the list.

Alex Kracov: And so is that just, alright, the confidence to not just - I guess maybe it's a combination of confidence and then not getting in the weeds around the tactics of why ever you're there, but it's more about the why this matters. Is that sort of what you mean by the storytelling and painting the picture of, okay, why, whatever you're trying to sell actually matters, going to make an impact on the organization? Is that kind of the way to think about it?

Matt Green: Yeah, that's part of the way. I think that like a lot of other things in life, confidence will come through experience. Because you'd build up the muscle memory. I think that it is more about, okay, here's how you effectively structure a story. Because it sounds easy intuitively. Like, okay, go in and tell a story. But in order to tell an effective story, there are some components of how you structure, how you deliver that story, right? That's going to make it more effective. So really honing in on, if you want to consider the science of storytelling, what captures people's attention, how you can position yourself as just a magnetic human being while telling the story so that people want to engage, they want to listen with you. Be really honing in on that kind of stuff outside of just building the confidence, which, again, would come through experience.

Alex Kracov: Going back to the first skill gap you mentioned, like selling through a champion, when you're doing trainings, talking about that topic, how do people actually get better at that? What are the tactics or things that you can do to better sell through a champion?

Matt Green: Yeah, two big things come to mind. Number one, it is understanding the concept of value articulation, how to articulate value to two different audiences with two different motivations, two different sets of priorities. So being able to develop talk tracks again for two, if not more, different audiences. The other skill set - and I love what people like Jen-Allen and Nate Nasralla are evangelizing around this topic - is writing. How do you become a more effective and simultaneously eloquent but succinct writer? How can you put together, how can you arm your champion with a business case that a CFO is actually going to read?

One of the things that we did maybe about a year ago is, we sent out a survey to the CFOs of all the companies that we work with. We just asked them a series of like seven or eight questions. Like, "Hey, how do you all buy stuff?" We're able to capture some really good data. Again, regardless of the size of the company or, again, industry vertical, whatever the case may be, all the CFOs pretty much said the exact same thing. Which is, if they're going to look at something when making a purchasing decision, they don't want it to be more than one or two pages max, right? They don't want detail on like, "Hey, here's all the features and functionality." They just want to say like, "Hey, how is this going to drive more revenue or reduce risk within the organization at a grand strategic level? Not just within this team but at the larger company level. So being able to deliver that message to the CFO through your champion, when your champion may want to say, well, no, tell me more about the features and how this is going to impact just my team and the ROI versus the cost of inaction, that right there is a skill set that does need to be developed and honed in this day and age, just like the concept of being able to write for different audiences.

Alex Kracov: The other thing I will add to that is, Joey, who's our head of sales, he had something he really preaches. It's like the calls between the calls. You have your standard intro in your demo call. I give these big moments. But where the deal is really won is these little prep calls with your champion. And on those calls, you can ask the real questions that actually get to the real pain. Then that's where you can get the information to actually build the business case that's eventually going to get to the CFO. That's something that he is constantly preaching to our sales team. It's, okay, what's our next step? When are we getting on a prep call with them, talk about it? How do we kind of angle our solution to them? I think that's something - I've learned so much about sales just from watching him do that. Because kind of the way I was trying to work with champions before was just through those big calls. And I don't think I did a good enough job of like, okay, really buddying up to them to kind of turn them into a true champion.

Matt Green: Yeah, that was a big learning for us over the past year as well. Because, again, in the Zurp area, any VP of sales, CRO here, she'd be like, "Yeah, sure. Send it my way. I own the P&L. I own the budget. Sure. We'll get it set up." But then, come into the realization post, SVB collapsed, if we want to call that the tipping point. That every purchasing decision that's going to be made is going to be made when I'm not in the room. Just always keeping that in mind where you mentioned that the calls between the calls, I would go a step further and say the conversations between the calls, between the calls. That are only happening internally, that you're not privy to, you're only getting a heads up afterwards. How can you put yourself in the best position to make sure that those conversations between the calls, between the calls, are going to position you in the best way to make that sale?

Alex Kracov: So Sales Assembly is doing hundreds of these trainings every year, and I'm curious what is the right - what's a successful training look like? Is it more lecture format? Is it interactive? Do you give homework? What is the secret to putting on a really good training for a sales or a customer success team?

Matt Green: Two big things. Number one, while we do have an on-demand library which is useful, we're big believers in live training. Live training, all the research shows, tends to lead to better learning outcomes. And that's what's most important, right? Whether we're talking about building a business or just building effective training, if live training is going to lead to better learning outcomes, we need to make sure that we're honing in on that. Downside for Sales Assembly is that if you're not managing or leading go-to-market teams in North America and Western Europe, we're not going to be in the best position to support you right now. But again, for those that do have teams in those time zones, we are going to be in a good position to have a big impact. So number one, live training.

Number two, make sure it's collaborative. It cannot just be lecture-based. Specially, we like to think with sales professionals especially, if we're being honest with ourselves, the more cynical tenured sales professionals. I've been doing this for 10, 15, years. I've been around the block. I've been to all of the trainings. I know everything. When you put those folks in a room with 50, 60, 100 other people that have all been in the business for 10 to 15 years and have all been around the block and were all not only learning from the facilitator but having the opportunity to learn from each other, that is only going to do not only enhance the learning outcomes but just, as importantly, it creates this really cool gravitational pull effect where the individual contributors that go to our programs want to keep going to more of them. Because they look and feel different than the traditional training where they're learning within the four walls of their organization or maybe just consuming stuff on demand. It's like no, I'm hobnobbing with my peers at all these big B2B tech brands that I recognize. So that's what happens during the day of. Then from there, what Sales Assembly does is we do provide reinforcement at day 7 and day 30 after every training is completed. There's this concept called the 'forgetting curve,' where if you don't put something that you learned into action within specific amount of time, you forget - again, I forget what the percentage is, ironically enough. But it's a substantial portion if you actually don't put in the action. So we do provide a good amount of reinforcement at day seven, reminding them, "Hey, here are the big takeaways. Share with us how you put this into place." Then again, at day 30, all the while providing resources to the frontline leadership of these organizations so they could take what we've taught their team and reinforce it, push it down internally, to sort of add that two-pronged approach.

Alex Kracov: Yeah, I think the continuous education that you all are providing is so important. And as you talk about like the jaded sales rep who knows everything, I think our industry has changed so much. It's just constantly evolving. My background is even more in marketing, which evolves so much, like the trends of what works and what doesn't. And so it's like, I think there's just so much alpha to be gained by going to talk to peers and seeing what works at other companies and figuring out those little tidbits of what's working for them. I love this idea of relying on your peers to kind of help with the training and to make you better. Because I don't know. That really resonates with, I think, how I keep getting better. I think one thing that's scary for me is, I'm a founder of a company I own in theory. I'm the guy at the top. I should know everything. It's like, I still feel early in my career, and I'm still learning. I want to get better, and so I'm trying to seek other ways where I can keep learning. I rely on different trainings and podcasts and different things like that. But it's like, I think the best people have that growth mindset and just want to keep getting better every day.

Matt Green: Yeah, especially at the leadership level, one of the things that we do here is those monthly coffee meetings that I mentioned a few times earlier. We still do Zoom versions of that every month for the VP and C-level revenue leaders of the companies that we work with. Unlike everything else that we do, it's not training. There's no structure. There's no content or agenda. It's just an opportunity. Joey has been involved in this pretty consistently this year. It's just an opportunity for executive level revenue leaders like Joey to show up same time, same place every month, have a room full of between 30 to 50 of their peers, raise their hand and say like, "Hey, I'm kind of struggling with this. How would you all handle this? This, that, the other thing?" Just exchange ideas and best practices. What you learn when you get involved in a community like that is, there are companies that are in there that are doing 10 million in revenue. There are companies that are doing 3 billion in revenue. No one knows what they're doing to an extent. Everybody is trying to figure stuff out as they go along. It is really cool that you will see the head of sales of, again, this billion-plus-dollar company asking a question to the head of sales at a 5-million-dollar company or a 20-million-dollar company. It was like, hey, we had that challenge and we solved it this way. So again, just having that learner mindset, which, I think to the point that you're kind of alluding to, not only is it critical in leadership. But by and large, you're probably not going to get to be an effective leader unless you have that type of learner mindset.

Alex Kracov: Totally. I found that the people at the smaller companies are often doing the more scrappier, innovative things that the big companies will be doing eventually just a few years down the line. And so, yeah, because they're just more willing to buy that new technology or to take that risk. And so, yeah, that's exactly what should be happening. It's, okay, the billion dollar-company people should be talking to the 10-million-dollar company people and figuring out, okay, what the difference is. Then the 10-million people get a lot of value from seeing, okay, how do I scale and how do I grow? Where does this kind of go from there? So, yeah, super, super interesting. Actually, while we're talking about sales leaders in particular, we talked a little bit about kind of the frontline skill gaps that are there. But are there any trends you noticed as AEs become managers, and managers become directors, and then VPs and CROs? How does that skill evolve? Are there any common pitfalls that you see as you kind of go from the people leading the deal yourself to actually running a sales team?

Matt Green: Yeah, you know, a big one - and I'm sure it's going to sound familiar to you and maybe a lot of people listening - is especially when you take that first step from IC into leader. Realizing that like, hey, at the end of the day, you're not everyone's buddy anymore. I mean, there is a responsibility, a higher responsibility, that you have not only to yourself, not only to the team, but to the organization as a whole. I think that a lot of people, when they take that first step into leadership, they don't truly internalize this. They try to lock this line where it's like, yeah, sure, I got to hold you accountable. But we're still bugs and this and that. I'm not saying that it's not important to have great personal relationships with your team. But those are always going to be trumped by the greater good of the organization as a whole and, therefore, by the responsibility that you have to, again, do effective deal coaching, to provide an accurate forecast, that you roll up to the leader above you. So I think it is just really stepping out of that friend zone type of mindset and saying like, "Okay. I'm a leader. Here's the enormous sense of responsibility and therefore accountability that I have right now." That's going to be again sort of the intrinsic things.

Another thing that we see some especially new leaders struggle with is having difficult conversations. If two people on your team are up for promotion, only one of them is going to get it. How do you have that conversation with the second person? You know, if there has to unfortunately be tough conversations around performance or even a reduction in force, how do you navigate those conversations in an effect of an appropriate manner? All too often, IC is making the jump into leadership. They're not provided nearly enough support by the organization to do these types of soft skill kind of things. They instead focus on accuracy forecast, deal coaching, again, some of those hard skills. But the soft skills tend to fall by the wayside, and that usually results in much more ineffective leaders than they could have potentially been otherwise.

Alex Kracov: I find being a people manager is so uncomfortable. I mean, at Lattice, it was kind of my first time really being a manager, the manager managers, you know. You have to have to hold people accountable, have those tough conversations. And it feels like against your human nature, unless you're maybe a sociopath who really enjoys it. It's mostly against your human nature, and it just feels weird and uncomfortable. I only got better at it by just at bats and trying and being put in those tough conversations. But it's really hard. It's easy to procrastinate. It's really easy to avoid those conversations. People, too often, do the shit sandwich. They want to say how they really feel. Then it's like, all right, let's cover them what's going well. It's like, no, you just got to be really direct and honest. Honestly, that helps whoever you're talking to in the end. At the end of the day, you're not leading them on. You're telling them how they can actually get better. I think just being direct as a manager, you can be direct without being an asshole, I think, is also really important.

Matt Green: Yeah, as someone who, as we spoke about earlier, likes to think of myself like, hey, I'm all about relationships, let's build good relationships with people, what you just said not only has been but to an extent is still a struggle for me, a big area of opportunity of improvement for me. And yeah, just to that point about not providing shit sandwiches, providing that direct feedback, for anyone who might be listening that, like myself, does struggle with this, think of it this way. Even say these words out loud when you are about to deliver direct feedback to someone is, "I owe it to you to be honest about this." Just start every feedback conversation that way. Because you do. It is legitimate. You do owe it to them to provide them that direct and sometimes might be tough-to-hear feedback.

What Today's Sales Leaders are Talking About

Alex Kracov: I'd love to end today's conversation with your perspective on, what are the biggest topics that are happening among sales leaders today? I mean, you all host dinners every month with 30 plus sales leaders. What are people talking about at these dinners? Is it all just like AI SDRs and things like that? What are people talking about?

Matt Green: For better, for worse, we still have the hangover of the AI SDR conversation. But it has, fortunately, in my mind, moved away from binary replacing - will AIs replace a SDRs - and more about like, okay, how do we repurpose the SDR function, and how do we make them more efficient by maybe layering some AI on top? So we're having much more nuanced conversations just around team structure now. But yeah, to be clear, specifically around the SDR function, how are they going to be the most effective in this new selling motion, this selling environment, that we're involved in? Outside of that, I mean, the other big topic that comes up very often, which is tangentially related, is just different and creative ways to drive pipeline. We're seeing a big shift, as we spoke about before, back to in-person stuff, whether it's trade shows, road shows or, again, just small experiences with prospects, with people that, at least on paper, fit your ICP, seen bigger investments into that. Just as a way to break through the noise, as you alluded to before, which is all this AI-powered SDR nonsense where everybody's inbox is littered. Everyone is getting cold calls. Again, that's another big resurgence that we're seeing right now. Is cold calling actually becoming in vogue again and sort of becoming much more effective than maybe it was previously? Those are maybe the two or three big things that we're hearing consistently these days.

Alex Kracov: Well, thank you so much for the time today, Matt. If anyone is interested in checking out Sales Assembly, where's the best place for them to find the organization or you?

Matt Green: Yeah, thank you so much for having me. If anyone's interested in checking out Sales Assembly, salesassembly.com is our website. If anyone wants to connect with me, I'm heavily on LinkedIn, so you can feel free to find me on LinkedIn. I would love to connect with you there and hopefully start a conversation.

Alex Kracov: Right on. Thank you, Matt.

Matt Green: Yeah, thank you, Alex.