Why the Sales Rep Matters More Than Ever in the AI Era with Brian Benfer

Hey, everyone. Welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Today's guest is Brian Benfer, who is the CRO over at Sales Loft. And if you've been following me for a while now, you know that I've got a long history with Sales Loft going way back to the early days with Kyle Porter. So watching it go through the acquisition and now the merger with Clary has been fun to track from the outside and knowing the people that were involved as well. Brian's the guy on the inside of all of it right now. But here's what I didn't expect.

Brian spent almost a decade as a swim coach, not a side gig, a career. He ran a year-round program at Wilmington, North Carolina, paid his way through school coaching. And when he finally decided to try something else and started interviewing for tech jobs, he was so bad at explaining what he did and what he learned that one interview even asked him if his job was putting swimmies on kids. He got his first SDR job on a coin flip at a company barred by Citrix. And a few years later, he was running 300 sales reps. Now he's going to tell you it was about luck. But listen to the way he describes managing swimmers, parents, and a board of directors who all want the same outcome and disagree on how to get there.

And you'll hear exactly why I don't think it was. And that's the through line through this whole conversation. We get into leading through a merger when the reps didn't sign up for one, why he thinks anyone who tells you what the market's going to look like in 24 months is absolutely lying to you. And how Salesforce runs what they call an AI ops factory to crowdsource what's working from the field instead of pushing it from the top down. Then we get into the stuff I really wanted to argue about where the rep fits when the tool can automate the whole outbound motion, the three skills he thinks every seller needs to know now that weren't required five years ago, and whether the buyers are 70% through the sales journey before they even talk to you stat matches what they actually see.

Spoiler, it doesn't. He's living in analysis paralysis like the rest of us. Oh, and his five-year-old made 250 bucks at the lemonade stand in two hours. So there's a future entrepreneur here in the mix. So anyways, I hope you enjoy this conversation as much as I did. Let's make it happen. Brian Benfer, welcome to the Make It Happen Monday podcast, my friend. How are you doing? Good to be here. Good to be. I'm great, man. Summer's over, but it doesn't feel like it. It's a beautiful day outside. It's a beautiful day at work. It's a beautiful day to be on the pot. Thanks for having me. Yeah, thanks for coming on, man. This is going to be a fun conversation. I mean, you know, Sales Loft, Clary, like we just talked right before I get on here, I got a real rich history with Sales Loft from the early days of Kyle Porter.

So to see the journey of Sales Loft and through the acquisition and then the merger and everything else has been fun to watch. And it's a whole new world right now. So we're going to get into that with the revenue intelligence and all that fun stuff. But on the podcast, I always love starting with the origin stories here, the stuff that we can't learn on LinkedIn. And Hugh, we got to get into the swimming factor here and how you went from like that for eight years and then all of a sudden started at 30 years old in tech. So we'll get into that. But let's back up a little bit further. Let's get back up further from that. Like growing up, your influences, your parents, like what they do, like kind of what, where'd you get your values from?

Where'd you get your work ethic from? Talk to me a little bit about growing up here. Yeah, for sure. Look, I mean, I think one thing my parents definitely instilled in me was a, was a strong work ethic. You know, I think, I think everybody's smart, you know, so I don't think you become successful just because like, oh, I'm so much smarter than everybody. Usually people who think they're so much smarter than everybody, by the way, nobody likes that guy. You know what I mean? But like, so like to me, it is like work hard and there's a certain amount of luck. Like, I feel like I heard this quote the other day. It's like J. Paul Getty quotes, like, hey, how do you, how do you get rich? Like wake up early, work hard and strike oil.

Yeah, exactly. You know? And so, yeah, we'll talk about the career journey. I certainly, you know, had some lucky breaks along the way and that had something to do with it. But, but work ethic, super critical. My mom was an emergency room nurse for a long time. Not an easy gig, 12 hour shifts, you know, seeing all, seeing all the things. And my dad was a career sales executive. So carrier corporation and kind of in that whole, you know, air conditioning HVAC world. So in sales his whole life. Interestingly enough, I didn't actually think I'd want to do sales. My dad's in sales. Well, he's retired now. Both my brothers are in sales. Everybody told me when I was growing up that I should be a lawyer.

I now realize, I don't think that was a compliment. I was going to say, what is, you know, like what's the underlying thing there? But that's what I thought I would do. And, and, and, you know, quickly I did end up taking that track, fell in love with sales in, in my first sales role for, for like the number one cliched reason. And it was very SMB sales. So you're talking to a business owner, but like literally first day I got the phone call with the prospect and I was like, we're going to change this guy's business. And like, to me, like that impact. And I know it sounds cliche and corny, you know, would your sales didn't help people, but like, I felt that. And I was, and I was hooked. I was hooked.

Was that Citrix? That was, I was at Sharefile. It was acquired by Citrix. Yeah. Okay. Yeah. So, so what made you make the switch? Cause again, you, what was the, uh, talk to me about the, it was like a, you had like a 7% attrition rate with this whole swim club and everything like that actually non-traditional path for sure. So, so I was, I was a swimmer growing up, you know, got athlete, got into coaching, uh, after I had an injury in college that took me out of the pool for a while, really loved coaching. Um, ended up using that to actually pay my way through school. Uh, and so after school worked for USA swimming and ran a year round swim program, uh, called the waves of Wilmington down here in Wilmington, North Carolina.

If you know anything about swimming, it's, it's very competitive. There's a ton of commitment that goes into it. And so I ran this big program. I love doing it. And it's funny, John, like they, you talk about impact on people's lives, you know, now that the athletes that I coached are, you know, grownups are married, they have kids. And I bumped into one actually at her wedding, you know, like a year or so ago. And like, she's, you know, telling me like this thing I said one day that had a big impact on her life. And it's like, you know, you don't real, and so it's just incredibly rewarding career. Um, and you know, where it ended up helping me and I never realized it at the time is you just learn so much about building teams.

You know, you've got, you've got athletes that, you know, basically like I want to swim faster in the pool, right? Like basically, right. Uh, but they have a way of, of thinking that they're going to achieve that, you know, in certain, uh, organizations and you've got their parents also want them to swim faster in the pool, but have a different idea. You have a board of director, same, same outcome, different, but you have a university, right? And, and so it, what does that end up sounds like? Well, I got a sales team. I got a marketing team. I got a product team. I got a people team. I got a legal team. I got a board of directors. I got investors. They all in theory want the same thing, right?

The business to grow faster always, right? And they almost always have different points of view for how you get it done. And so what does the coach do? He learns how to bring all these disparate groups together to pursue that one thing that they know is the outcome that they want. I didn't realize I was like learning that while I went on this almost long career in coaching. Um, and so I did like the worst job of articulating that as I was interviewed. Like I decided, I was like, Hey, you know, I want to, I want to try something different. I don't know if I want to be a swim coach my whole life. Maybe I can make some more money, yada, yada, yada. So I interviewed for all these positions and like, I don't know.

I feel like at one, even somebody was like, we don't understand. And so you put like swimmies on kids. I'm like, no, I didn't realize what I was learning. So I couldn't articulate it. Um, and, and it was just, it was honestly, it was luck that landed me in my first sales job for better or worse entry-level sales. And we're talking about a sales development rep, an SDR position or require a lot of experience, you know, and a college degree and some professional history. And so I get a job and there's a coin flip decision to take this position with a company called ShareFile competitor in the Dropbox and box space when that was all still brand new, you know, uh, and was acquired by Citrix. And so, you know, we had a lot of funding and we were growing rapidly.

I mean, you're talking about doubling, tripling the business quarter on quarter. So it's an amazing kind of like, you know, pressure cooker of growth. Um, and like I mentioned in, in that, you know, kind of fell in love with sales, but all these things that I had learned, you know, kind of bringing these disparate groups together towards a common objective, I think really helped me, you know, as my career advanced, be able to pull sales team together, you know, go over time, be able to pull, you know, companies together, you know, in pursuit of doing things that are really hard because they're really hard. Um, so tremendous payoff. And, and I, and I give that, you know, aside from hard work and luck, you know, that background, I think fueled any modicum of success that I could claim I've had.

Love it. Love it. And so you, you went through that acquisition with Citrix and then you went to dude, well, dude, that was then named, what was it renamed as I forget? Well, so I went from, I was at Citrix for about six years. Um, and, and honestly, the work experience was like 20 years of compressed into six, just so fast moving, so high growth, you know, new markets every other quarter. Um, and if I was giving advice to anybody, the only advice I'd have to give is if a leader taps you on the shoulder and says, Hey, I want you to go lead this new thing or try this new thing. Just say yes. So much of our growth was like, Hey, we think we should go on this market. Why? Well, we're not sure, but maybe it's this, this, and this, it never ends up being this, this, and this, you know, but if you can be the person to figure it out, then it leads to the next one and the next one and the next one.

Oh, you got my shirt now. It's called what it's all about. You know, like everybody's so wired to say no, or if you're messing up and I understand all that stuff. But if you're in a high IQ, high EQ environment, I golly, you know, if you work hard, the odds are pretty good for you. I feel like, um, so anyhow, that was a great experience. And, you know, before it was over, I was, you know, I don't know, a few, a few years removed from coaching swimming and running a, a sales team of 300, 300 reps, 150 SDRs, 150 closers is just ginormous outbound machine in the early days of SAS. Um, loved every minute of it, went over to solar winds, had a, had a stint there, uh, in their MSP division, which has now been spun out as a naval for a couple of years.

Um, and, uh, and then went over to dude, I knew the CMO there, uh, and she had called me up one day and said, Hey, you know, we've got this kind of, kind of similar to Citrix, you know, verticalized, highly outbound, go to market. We're looking for somebody to lead global sales, you know? And I was like, I don't know if things are going good. Ended up taking it. And, and again, another kind of just lucky decision. What an incredible experience. Uh, we were dude solution to, you know, a very U S oriented company, um, you know, uh, transform that into brightly software through acquisitions and just global growth. You know, we found ourselves in Australia and in the UK and in India and Canada, really professionalized, globalized that business, ended up exiting that, uh, to Siemens a few years back and, uh, and stayed along during the, during the course of, you know, post Siemens acquisition for another three and a half, four years, um, before Clary came knocking on the door.

And, you know, I was a long time user of sales loft, long time user of Clary. Clary's the cockpit as a CRO for how I run my business. Uh, and so you talk about something that sounded, you know, I, I, I loved what I was doing at Siemens, loved it. Asset management is such a cool field. And like, once you get behind the curtain of how the world works, right. Which is like all this stuff behind me, the roads you drive on, you know, the widgets that are manufactured, the, the air conditioning units that are in my kids' building, how you maintain the right temperature and pressure in an, in an operating room. This is, this is all stuff that, you know, these are assets that may have to be maintained and operate the world we live in.

You never think about it. And then once you're in that world, oh my God, this is so cool. You can tell I'm still very passionate about that space, but I'm equally passionate about go to market. And, uh, and so the opportunity to come here and get to do this and, and, and talk to other revenue leaders, you know, about how they grow their business and, and what the latest, you know, techniques and tricks and strategies are, um, is, it's just, it's the coolest job. It's the coolest job. It's the tip of the spear too. And I think, you know, talking to clients right now, I mean, the, the challenges I think have never been greater, but the opportunities I don't think have ever been greater either.

So, uh, working people through this and being part of it, I think is, is fascinating. And I'm curious on your, your, you know, you say luck, right. But I, I believe, yes in luck, but I also believe that you make your own luck in a lot of ways. And also just from a, from your standpoint, like decision made, I'm curious how you, how you look at making decisions. The reason I asked that is because I think for me, I've always been a, yep, that looks good, but I'm not like a major risk take, like a, like the ultimate risk taker of like drop everything, you know, live in my parents' basement type of scenario. But, um, but I'm, I've always said I'm, I'm like an opportunist, right? Like I, I usually can look at two or three kind of data points and be like, yep, that makes sense.

Let's do this. And I don't overanalyze. I just kind of usually say, yep, let's go. Now it's burned me a few times, but the most part has worked out in my career. So do you have a way of looking at opportunities that you kind of break down or is that more of like, just kind of your feel for where you are at the time? Yeah. Yeah. Well, if you're thinking about, you know, opportunities and like, Hey, how I scale, like what I want to do next with my career, and am I going to go work with this company, et cetera? Look, let's, let's call a spade a spade. Like that first decision on ShareFile, like pure luck. Cause I knew nothing. Like I, I was like, what's the clouds? No, like nothing, literally nothing.

Right. But then, and this is why I think that you can kind of trust your gut or only have maybe three vectors you're looking at. You do develop pattern recognition over time. You know, you kind of understand how to, you know, look at a business's financials and, and, and get, and understand the direction that it's going. You, you know, you learn how to meet a room and understand, you know, like, is this high IQ and high EQ? And, and, and I brought that up twice now because I think it's genuinely important, right? Business, particularly software business, like our main assets are our people. Everything else is ones and zeros, you know? So it really comes down to like, are these really intelligent people that, you know, I can learn from that are going to help us see around corners that collaboratively, like we're going to figure this thing out because just like your shirt says, that's all business is.

If they gave us a playbook, we just execute the playbook, do this on Monday, this on Tuesday, this on, and then we'd all be gajillionaires. You know what I mean? Right. Yeah. You know, so, so it's all about figuring it out. So you want to do that with smart people, but, but, but like, here's the catch, right? It's gotta be high EQ in the leadership. And this is really, really important because we're monkey see monkey do animals. And I don't know why this is the case, but just like everybody asks, acts how the leadership acts, you know? And if this boss is a jerk, it just has the weirdest way of jerkifying everybody else. And, and that leads to lack of trust. And in a lack of trust environment, it's really hard to say, oh, you tapped me on the shoulder to take this risk in my career.

I'm going to follow your lead. But if you have those two things, high IQ, high EQ, you're probably in a fast growth environment. If you're excelling in what you're doing today, somebody is going to tap you on the shoulder and that's the environment you can say yes in. And that to me, like, that's where you have like these non-traditional kind of career growth journeys. And that's what mine has been. It was not just like this new year thing. It was these sort of step function leaps. And really just because of that. So you talked about trust and leadership and leader. I mean, right now, I don't think I've ever been in a, in a, an environment that is changing so fast, right? With AI and everything else.

So leading through change, the acquisition, the merger with Clary, you've been through a bunch of mergers or acquisitions. How do you build trust in a scenario where a company like the reps didn't sign up for being acquired? You know what I mean? I remember when I was my little $10 million company got bought by a $20 billion organ, you know, by Staples. And I was the point person going through that, you know, at the time, the CEO was, was almost still trying to pretend like, like, oh, we're still this company, right? We're still this little $10 million company when we were obviously had to be assimilated into the mothership. And there was that path and it broke a lot of trust because it was almost speaking out of two sides of his mouth when it came to the message that he was delivering to the team and then the conversations he was having on the back end.

And so I think it really didn't do a lot of favors for the organization. How do you approach change right now and leading through change and, and building trust and, and, and trying to reduce any type of anxiety that might be happening? Because I, because the more people I talk to right now, almost everybody's anxious and almost everybody's just exhausted too, because of the pace of what's going on right now. So how do you kind of bottom up, if you will, build the team, you know, and, and get them rallying around this constant change that we're all going through right now? Yeah. Authenticity. I, I really think that it's as simple as that. You know, I think that, you know, folks that claim to understand exactly where the market is going to be, what the North star is, what the product's going to look like 24 months from now, they're liars.

You know, it is, you know, you don't know that, you know, and, and so, you know, whether you're bringing two companies together and, you know, maybe they have legacy, you know, juxtaposed cultures or, or just things that are different. Right. And it's not, you know, the thing about a merger that's different is like all companies, culture changes over time, if only because of time, but usually also because of growth and complexity and other things. And I've always correlated that with like, you know, I'm a different person at 45 than I was at 35 than I was at 25 than I was when I was five. But I'm the same person. And in fact, I don't know if this is your experience, John, I'm more like my five-year-old self.

And I don't necessarily mean that from an immaturity, but I find like the older I get, like the more I am, like I was when I was a kid, like there's a certain phase in your life or you need to try to be somebody you aren't, you know, and then you just kind of learn. And so to me, culture and a natural evolution is a lot like that. Yes, you're fundamentally different, but at your core, the values are still the same. And that to me is like most, most culture where I think a merger is a little, is a little different is it can be more inorganic because you take in like two totally different things. And on Monday, they were on Tuesday, they're that, and that's not the change and sort of organic growth and cultural change.

Right. And so, and so with that, again, I think authenticity is really, really critical. Because I think you have to give people that, you know, hey, this is who we are. This is what we believe. This is where we're going. This is why we're going there. This is how we're going to get there. These are the things that we're not sure on. These are the things that could go wrong. This is how we're going to manage it. Lay it all out. Be open, be honest, be direct. Like nothing I said in there is like confidential IP that you can't share with people. You know what I mean? And then allow people to choose. And by the way, like also nothing wrong with, you know, hey, I was part of the organization for the last 10 years.

And like, I correlate it back to the share file experience. I have extreme nostalgia for that experience. Extreme. It exists as a piece of my mind or something. And guess what, John? It doesn't exist anymore today. You know, it's still like, this is a great organization. They're part of progress software. There's a lot of people that I worked with that are still there. They're doing wonderful things, but like, it's not the same thing. You couldn't convince me to go back there and have it be the same thing. That there's a lot of people that post-merger, I'm not necessarily speaking specifically to sales loft and Clary and whatnot, but like, hey, the new thing is not the nostalgia of my own thing.

And it all sounds good, but I'm ready to do something different. And that's great. And I actually think like we should just make those decisions really, really quickly so that like the core business can thrive and you get people on and you keep on trucking. I think you just had to be authentic with people and, you know, it works itself out. Yeah. So, so leading through, you know, kind of being an open book as far as what's, you know, where we're going and all that other stuff. But with this change, like with AI right now, yeah. Um, you know, and the adoption of AI, you know, you got the spectrum of people. Some people are scared to death of it and want nothing to do with it. Others are all in on it and everybody else is kind of in the middle.

And I think these days, the, the kind of top down decision making from an executive standpoint, it, I don't think it's the best way to make decisions anymore. Right. Because by the time you make that decision and then train the team and then, you know, all that stuff, you're probably six to nine months out of anything of meaning. And then to your point, like, I don't know what six months is. I don't even know what six weeks from now it's going to look like. So, so this bottom up approach of involving the organization in the change is where I try to, you know, at least coach the, the, the teams that I work with. If almost you want to turn your sales org into a sales lab where you get together once a week, you pick a topic, you nerd out on it for a little bit, you come up with a solution, you implement it, you iterate to your point, like making fast decisions.

Right. So how are you, um, kind of involving the organization in this change? So it's not just, Hey, CEO makes a decision, CRO makes a decision, that type of stuff. And you guys are now doing it because not only are we in a different, um, uh, environment from a business standpoint, but also culturally, I mean, this, this generation just doesn't, you know, I mean, I'm a Gen Xer, right? I just hit 50. And, you know, for me back in those days, it was like, give me my territory, give me my quota and get the hell out of my way, please. Like, I don't need any of this fluffy stuff. I don't need any games. I don't need any of that crap. We were over the moon when we got click the dial. I remember. Yeah, exactly.

It was like, okay, cool. So, and you, you know, boss, tell me what to do. Fine. I'll go do it. I don't care. Right. But now it's, it's like the, you know, the involvement in the, in the, uh, retention of employees and everything is critical here to build this culture. So how do you, how do you do that over at sales loft these days? Yeah. And it's not dissimilar to the approach that you were talking about. And by the way, like, I would like to think that's the way that I've always run my organizations, like going, going back to the high EQ and figure it out. You know, if all of the ideas are coming from me, watch out first of all, and secondly, I'm not the guy that is the closest to the client.

I'm not the guy that's closest to the cold call. I'm not the guy that's on the, like, there's no way that I have the breadth and depth of information that the folks, you know, running the business, you know, executing the business do what I can do is make the entire organization move really, really fast. You know what I mean? And so, and so we crowdsource a lot, you know, and, and then once we latch on to things that we see working, we push that and AI is a great example. We have this thing called the AI ops factory. And so, you know, if somebody comes up with a new way of, of, you know, how they're automating some of the account research we do for EBRs or how they're doing account planning or call planning or cockpit they're living in, you know, day to day, like we, we train a bunch on Claude and other tools so that folks are prepared to do this, give guidance, push out skills so that we're not a burning tokens on just like five coding my way to success and be just like coding my way to a non-productive day.

Right. But, you know, taking what works and pushing it through AI ops factory so that we can scale it out because one of the downsides of, of kind of just allowing everybody to go buck wild and do their own thing is, and you'll know this if you've ever played along with an LLM long enough, it's like, you can just go down a rabbit hole, try to perfect it, make sure you're looking at the right source data. Oh, this piece doesn't match this piece. Oh, I was looked up to the wrong field in Salesforce. So standardization and being able to push that out becomes really critical and sort of just limiting that because at the end of the day, I think like the, if we think about all the productivity levers that we can drive in sales with AI, we, maybe we'll come back to that.

So I don't, I don't take us too far off track, but like, look, the big one is giving time back, which it should improve like capacity to be able to talk to more clients. It should be used capacity and opportunities. And so like, if we're just spending all of our day vibe coding new tools because it's only bottoms up, we're, we're also going to fail. Yeah. So let's talk about this change that I, and I think sales loft is a great example of, you know, a company who's been there through this change and stewarded a lot of this change, especially specifically from an outbound standpoint. I know we're going all the way through and have the system of record for the call recordings and deal management and everything else.

But let's talk about outbound for a minute here, based on what you used to do with sales loft, kind of the early days. I remember Kyle and I used to get into arguments because the, you know, sales loft was like a personalization at scale. I'm like, could you please stop with this? Because just because you change the name, the title in the industry doesn't mean this email is personalized. Okay. Um, you know, it's, it's better than, than not, than spam, but now we're in a, in a world where we can personalize really at scale. We can look for that information. So how, you know, we, I think we got a little ahead of ourselves in the SAS days of the, you know, just blasting out, you know, when money was free, grow at all costs, who cares?

Right. It didn't matter as much that we, we littered our audience with, uh, messages because, you know, 16, 17 touches, whatever we're getting meetings now, you know, there's a backlash to, to the spam. It's not, there's some stats out there that I was looking at that people don't just, you know, um, ignore bad outreach. They, they actively avoid it and they actively avoid the companies that do it to them. So how have you seen outbound from your perspective, change, uh, over the course of using sales loft early days to what you're seeing now? Yeah, for sure. It's a great question. And then look, I think like going along with that, like everybody talks about, you know, connect rates dropping.

And so then, you know, is your SDR engine still efficient and, uh, getting less efficient. So now I need to put my SDRs up market, but all the model wasn't built for that. And so now I have this whole cost constraint problem. And then people are, you know, making drastic decisions around this when like, we actually just need to pause and think about, okay, how do we get more targeted in our outreach? At the end of the day, there's a heck of a lot more information available to us. And I think the difference between now and even a year ago is how quickly this stuff is moving is we can contextualize so much of that information so that we can say specifically what we should be doing in an account, specifically what we should do in an opportunity.

And that's telemetry based on our conversations, our emails, our product usage, signal data from, you know, websites, et cetera, et cetera, right? Like kind of list goes on. If you're doing that in a really, really narrowly defined ICP, and I think like real coordination between sales and marketing, I'm one of those guys that have always said, like, I don't know where demand gen ends and sales begins. Like, I think if it's done really well, it doesn't, right? It's like this, you know, do I always want more leads? Sure. Like, yeah, but like, but you know, but like to really run this and run this efficiently, like, that's that, that's the level that it takes because, you know, I, I agree with you.

Like, somebody is just going to spam me with a whole bunch of emails. Like I'm not too interested in, but there is this interesting net psychological effect. At least I noticed on me where like, and I am probably just in somebody's like ABM algorithm or whatnot. But if I, if I just feel like I started seeing them all the time, you know, and then I get, I get a pointed message. I'm like, I'm way more, I'm more engaged. I'm like, these guys are everywhere. Like what's going on? You know? So that one is still working on me. And, but again, I think it goes back to just being really calculated, really targeted, really data driven and, and having a tool set that can texture, can contextualize all this information relevant to your business.

And that's, that's where sales off is today. So where does the sales rep fit into this equation and like, and moving forward, specifically on outbound, we're going to get to the rest of the, the, this process, but you know, it's, it's, it's realistic to extrapolate the fact that we're, we have now such powerful tools, such good insight, such ability to contextualize this information that sales loft could fully automate the outbound component to this. Um, maybe not the phone call. Right. But, but the research sequence, like all that stuff all the way forward. Sure. Right. So, so where in your view with all that information with, uh, you know, uh, a tool that can, that can deliver this stuff, where is the sales reps value in that equation?

More important than ever. More important. Um, you ever chatted with, I don't know your soup du jour LLM. I used, I use chat GPT more for personal and Claude more for probably a lot of people like that. You ever like pursued a buying process with chat GPT? Okay. Great. Do, do you think it shortened or did it lengthen the buying process for you? And in particularly like the evaluation criteria? I think upfront, it shortened it. Um, the validating it, I think is where, you know, the trust factor of that. Um, and there's, there's, you know, I've been looking at this too. There's stats right now that, that people don't trust, you know, the output of AI, like 50% don't trust it, but 50% also don't trust us.

We're coming out of the mouth of a sales rep. So we're almost on a dead heat tie with, with trust, which is the, the, which is, I think everything moving forward here. So yes. And you know, people say, oh, well, you know, people are always going to want to talk to people. Yes. And if that conversation is valuable. Yeah. And my thought is, is my experience is, is that AI is getting more and more valuable the way I get to learn, like the more I use it and the more I understand how to use it. Cause my fear isn't necessarily all these tools that are automating sales. My fear is that when the sale, when the client starts to really lean in and go so far with their evaluation that the set and the sales rep starts, and we've all heard that stat by the time somebody comes to us, they're already 60 to 70% of those blah, blah, blah.

But those are usually, that was a misappropriated stat because that was all inbound hand raisers who had done the homework and said, yeah, now I want to talk to somebody, but now any idiot five minutes before a call can run a prompt and get pretty damn far as of whether this is something and what questions should I ask. So if the sales rep isn't meeting them with value in that moment, they, they, they become an irrelevant part of the equation. Yeah, definitely a risk. I don't know. And so to your, to your point on the, Hey, 60, 70% of buyers are kind of already self-qualified along the way. My, my experience has been maybe a little different and maybe I'm just like an obsessive person. I almost always end up in analysis, paralysis.

It's so much information that you can rabbit hole that then it makes it become like, you just know way too much about the topic, but it's all kind of feature related. And then the problem that you thought you were solving in the beginning, now you're not sure if you just have a different problem, but that other problem costs more money. And so now it's not apples to apples compared like this, these are like the rabbit holes that I ended up going down. And I think it's the same for a lot of people. And I think the proof in that is, you know, people talk about like the martini funnel now, which is there's like, there's big thing and it's all up here. We don't have visibility into it. There's so much swirl going on here.

Cause they're getting so educated, but that would imply that by the time they get to us sales, that ain't my experience, man. You know? And, and, and so like, and then part of that is, yeah, like buying committees are just as big as they've always been, but, but the regular evaluation cycle just as longer or longer than it was before. So something's not, not clicking there. And, and to me then the value of the seller is, it goes like, it's like, it's back to the future. You know, do I understand your business problems? Am I able to align my portfolio with them? Am I able to provide you any value, whether or not, you know, that's, that's the case or not, because that's ultimately how I build trust.

I talked to our sales team a bunch about this, particularly our account directors who work with current clients. There's stuff on the self that of course that you want to sell them, but you've got to show up and provide value every single time you have an interaction with them. Maybe they're hiring for a role and, you know, somebody who could be good or, you know, a recruiter where they need help with some other portion of their business. And there's a partner that, you know, from a prior life, like the list goes on like a million different ways to work our network. This is how you build trust over time with folks. And I think with everything that's out there now, you said it already, trust is paramount, absolutely paramount.

And, and the way that you do that, which was kind of a conversation like this, you talk, you get to know one another, like you fully engage with somebody. And I've always coach sellers. And it's, it's weird that you would have to coach this, but it, well, maybe not, but you know, I think your base, maybe it goes back to your, your 10, 60, 30 thing, your base case, like the 30% for sure, but definitely not the 10%. They get on a call. They have a goal. I'm going to get you to the next step. I'm going to get you to buy. I have my blinders on. I'm going to ask all of my spin, spice, med pick, whatever my criteria is. I'm going to do them all. You know what I mean? And I'm going to stick to the script because I'm talking to the CFO persona.

This is what I say. And this is the most, you know, straight line way to get, but the reality of the deal is everything that's out here. And I've always coached my sellers to be curious and, and let it wander way out here. Who knows what you're going to learn along the way, you know, that eventually like the, the gates will close in and either you'll have something or you won't, but either way, it'll be the truth. And most sellers keep their blinders on. They never get trust and they rarely actually get the truth. So the deal they could have won, they lost it. This seller, if they lost it, we just weren't a fit and that can be okay. You know? Um, so, so to me, like the, the, the seller, the seller value is paramount.

The seller's skillset has probably got to have all to meet the moment. I was, and so that's what I was going to ask is what are you training the teams on these days? Cause it used to be, we would train them how to do the research, how to, you know, come up with their point of view and those types of things. But now all that stuff's a click of a button and, and, and let's bring this to the merger. And I use this example a lot, right? Where, you know, the merger and acquisition example, and, you know, as a trigger event, right. And, and, and AI is going to write a absolutely glorious email that, that sounds to the uneducated, somebody who's never been through a merger and acquisition, it's going to sound fantastic.

Right. And so the kid, the 22 year old kid's going to take that trigger event. They're going to look, copy paste, cause that's better than what I could send. And it's going to send to somebody like you or me, who's been through one and it's either a going to land like a fart in church because like at that moment, I'm like trying to figure out when am I going to get fired and what I'm going to do. Right. And so you missed or even worse B it's going to land and it's going to get me the meeting. And then when I get on the phone with the kid who's, who has no context around really what happens to a VP of sales going through a merger and acquisition, they're not going to be able to get any value and they're going to lose the credibility there.

So how does that in this world where information is a commodity? Basically knowledge is a commodity in a lot of ways. How do you, how are you teaching kids coming out of school, the context that the acumen to be able to use that information the right way in a conversation like this? Yeah. Yeah. I mean, absolutely critical. And to me, like there's, there's, there's probably like three, like beyond just the typical, like, you don't know, like you hire a seller, we're going to teach you our baseline sales methodology. You understand the science. We're going to teach you our vertical. You understand who we sell to, the problems that we solve. We're going to layer on top of that, the comp, the competition we have, you're going to learn how to handle the objections.

You still get to do all that stuff. I don't think any of that's changed, but like, what are the competencies that lead to success today? And to me, like there's, there's just like three really big things. Uh, first of all, like it's a little bit back to the future in turn. Like you, you're, you, you said it earlier, you're 50, so I'm not calling you out on it. You said, yeah, no, I'm an old man here, man. We're six in a few weeks. I'm catching up, man. Um, uh, but if you remember the move from perpetual to sass, right, this was, this was a thing, right? And, and this was ended up the challenger sale really kind of rose to prominence during this time, right? Cause we were kind of challenging the status quo and doing things.

What's that? No, I just, I have my own opinion as a challenger. So yes, we could rip on that all day, but, but, you know, as an, as an aside, but, but the other piece was, is like, this also became very much a CFO sale because we were converting traditional CapEx, you know, purchase into OpEx to purchase and given, you know, providing this season. So you can put the CapEx dollars elsewhere. We're going to solve your business problem with, then you do other jobs, OpEx, and you print money. That's just, you know, the net, right. Um, not said with a high degree of business acumen in the way that I have summarized it, but I need to do it quickly, but that level of business acumen to be able to talk to CFOs and CIOs really, really critical because what's happening now today is another sort of challenger moment, right?

We're challenging the way that we're thinking about software. We're challenging the way we think about how many vendors we have in, in tech consolidation. We're challenging the way that we think about how we deploy our spend, because I haven't heard of too many, you know, software AI OpEx budgets really going up. What I've heard about is dollars shifting from one over into the other. And so how do we have this business level conversation beyond the point level, right? The point level conversation where I trained you on the market and the competitor and I'm selling to the VP of sales, all status quo stuff. Our sellers now have to be able to have a CFO, CIO level conversation because of how quickly the market is moving.

So business acumen is, is to me, I think a really critical one and probably under taught. Um, love to get our CFOs. I've done this over time, get CFOs with the sales team, do regular sessions, have them in same thing with CIOs and selling to CIOs, and then just imbue. Technical acumen, I think increasingly important. You were also from a certain time where we did our own demos, you know, like I didn't have it, but over time, SAS has evolved. And by the way, our sales engineers are our secret sauce. They're amazing. This is not an argument against sales engine. But over time, we had the SDRs, they do just this. Yeah. The AE that just did this thing. SEA just did this, right? And we were going to scale businesses this way.

And as a result of that, there's a whole generation of AEs that have no idea how to use their own software. Now we're showing up in customer, you know, and we're lucky because like, we can literally just flip the screen around because we're using this stuff to run our business and then we're going to show you how to do it. But, but, but like you have a whole generation of AEs that like never learned how to use the software they were selling. Now you got to show up and it's not, you're not just selling configurable SaaS anymore. You're probably showing somebody a solution that's going to get deeply ingrained in other agentic workflows they have in their business and probably customized if they're not building their own agentic workflows from your own tool.

It's very technical. And if your AE can't have a level of technical depth, not necessarily SE level, I don't know how you gain trust, you know? So business acumen, technical acumen. And then the last piece, which I just think really, really important, kind of ties back to analysis paralysis, but that it is, I already mentioned in this, you got a VP of sales, you got a CFO, you got a CIO. Let's not forget, you got the VP of BDRs, you got the CRO, you might have your CSM side that's doing some sort of stuff. You're going to have procurement at some point, you got legal. And this is for a small deal. This is for a large deal. Sales reps have to be better than ever at maintaining momentum in basically a large project management exercise.

The best enterprise sellers I've ever met, they know how to read a room and be great sellers, but they're fantastic project managers and can maintain momentum through a difficult project or not difficult, it's not the right word, but you know, longer stage project. And by the way, like those don't show any sign of getting smaller or slowing down at all. I think you got to nail those three things on top of the 101 stuff to be successful in today's environment. Do you think we're headed back to full cycle sales? I think the opportunity is there. I think it depends on the company. I think it depends on your go to market, the own unit economics that you're trying to pursue. I think that the, you know, the piece that that potentially opens it up if it's, if that's the right, you know, pursuit for your business is AI.

Because I think that AI should improve most of the baseline sales KPIs, but I only think they provide a step function improvement on one of them, right? I think that, I think that, you know, stage velocity, which is basically like your sales cycle should get a little bit better. You know, maybe it's 10% better, 20% better, but I don't know that it's step function because we're doing meeting prep and meeting follow up in this. I think conversion rate probably gets a little bit better again because you have more velocity. Okay, cool. I don't know that you can, you're not going to impact your average deal size, right? Like that's a price book or market targeting thing. And so the only other lever and sort of a rep productivity equation is opportunity volume.

And opportunity volume is tied to my ability to generate pipe at pace and how many hours I have in the day. And that's the one where you could have a step function improvement because all of the other work that you were doing pre post meeting is now automate automated and the pipe gen efficiency should get to a place where it's much more automated. The actions you're taking are actually the next best actions within an opportunity, with an account, within a prospecting set. And this is the piece that I think can double. And now you actually have step function improvement, doubling the, are basically my capacity in terms of my opportunity volume and through our account volume, if you manage your account, whatever.

Right. And then, you know, relatively like marginal, but meaningful improvements in the other three KPIs. I like that. That makes sense. Let me, I'm going to shift gears a little bit here. How did, how is sales loft looking at the presentation layer at this point? Because, you know, the announcement last week or whenever it was, Claude Force with Salesforce, you know, Benioff was basically waving the white flag saying, look, we're giving up on the UI. Right. And thankfully, right. Anyways, that's a different conversation. Uh, and they're saying, look, we want to be the, we want to be the system of record, but you can now do everything in Claude. You can tell Claude to run, you know, an analysis for you, give me my top five deals and all this other stuff.

So where, you know, in a world where, where you see the MCP connectors and, and the things that are, that, you know, and most people wanting to kind of stay in one platform. And in, and sales loft is a great example of that, like point solution towards a platform solution. So that you can get more people just staying in one platform, as opposed to just going from here to here to here in the glory days of SAS. So how is sales loft right now looking at that, that dynamic there of being a platform that you want to, because it was almost like sales loft tried to be that for Salesforce, right? It's like, yeah, yeah, you can have all your records down there, but we want you to live in sales for sales loft because of all the, you know, different value that it brings.

Now you cut Claude. Now you got, you know, ChatGPT and people saying, I like, I'd like to stay in here. So how, how are you strategy? How are you thinking about that? You know, as things scale here? Yeah, we look, we embrace it, first of all. And, and, and maybe I should back up a little bit to talk about, you know, why, why we think that is the case and, and, and more importantly, you know, how we, how we help support clients in that journey. Because I, and I talked to the, you know, the entirety, I don't want to call it the maturity curve. Maybe I'll call it the spectrum of, you know, folks that say, we want to be headless. Now there's even fewer that know specifically down to the use case, what that's going to be.

And I'm not knocking them. Like, I don't know. It sounds cool. I kind of want to do it too. I think I kind of know what the agentic workflow is, but like everybody's in the kind of space, but again, it's moving fast. Three months from now, we could have really well-documented job to be done of headless. All that, all that said, I'm a cloud power user. We've talked to a number of folks that are, or have, you know, individual record. We want to, we want to, you know, meet you where you're working because, you know, we fundamentally believe that, look, one of the, one of the, we saw this during SAS, you had this explosion of applications and then pandemic hit, and we tried to kind of reel it all back in.

We're seeing it again with AI explosion of, and now every, and the ultimately it's creating the same problem we had before, which is silos of data, silos of signal, therefore inability to act, rep swivel chairing, right? And so our point of view, and what we want to, what we want to, you know, provide for our customers is a single data layer to which we apply a context engine. And that context engine is really the most important piece, because that kind of what the context engine is doing is, again, it's going back. This is looking at your organization's calls, email, emails, CRM data, you know, data that lives outside of that in terms of a product telemetry. Maybe you care about billing, you care about, you know, usage, just tracking another source, you know, if you're interested in the prospect market and you want to know, you know, who's coming to your website or doing other sort of searches, you know, what have you, aggregating that data against the context of your own business.

Again, tons of data that we pull together to be able to say, here's the next best thing that we should do in this account. Here's the risk that exists in the pipeline in the, over the course of the next quarter. Here's where your deals are not multi-threaded enough. Here's where these competitive scenarios are coming up and here's what you should do about it. And by the way, like these scenarios vary, whether you're the CRO, the VP of sales, the leader of the BDRs, the SDRs, or the individual sales rep themselves. The important piece is that it becomes autonomous. And so it's no longer, I listen, I diagnose, I say to do an action, we watch the action, maybe the action has an impact. We're not really sure.

And we repeat the cycle. And this becomes measurable and always measurable and always on. And, and, and that's the direction we're heading. And so from a UI experience, this will become more unified over time. We're already taking steps to do that. And we'll also allow folks are allowing folks to be able to, you know, pull that information out via MCP. And I think over time, again, we talked about like, where is this going to be 24 months from now? I'm not one of the liars that's going to tell you explicitly, but I'm more than sure that, you know, there'll be folks that have specific agentic workflows that are unique to their enterprise, that they'll need to surface via MCP to both write back to our, you know, to our software and our data layer and to extract that data for their own unique workflows.

And so we may see a world where folks are in our UI for XYZ use case within their business and within, you know, their MCP enabled UI for things that are very, very unique to their enterprise. Cool. The, I want to touch on this on the kind of one of the last points here is, you know, I was reading a couple of the articles that sales loft had put out recently and there was one announcement that said 67% of revenue leaders don't trust the data their AI relies on. So how do you balance that sales loft with the fact that you got AI agents monitoring and telling me what to do with these deals? This is like, this is my hang up a little bit. I don't trust AI on my deals personally, because I know my deals and I've been in sales for 30 years.

And so when I'm like, Nope, I'm not going to send that email today because I know that this, and I'm going to do it this way instead. And I'll take some advice, but I'm not going to have any, I'm not going to have an AI agent tell me what to do with my deals personally. Um, so how do you, cause you know, I thought AI was going to solve the garbage in garbage out problem. It's made it exponentially worse, right? It just, it just amplifies whatever, if you have shitty data, it's going to amplify shitty data. If you have shitty messaging, it's going to amplify shitty messaging. And so, so, so how does, how do, how do you, um, deal with that? Right. Where the distrust in the data, but yet you're now saying AI is now has to, is going to tell you what to do with your deals.

Yeah, no, no, no. It's an excellent point. I guess, you know, I, I would say two things. One is, and I get to sit with, with a lot of clients and review their usage of value they're getting through the tools. And I mentioned, I was a long-term Clary customer and, you know, what Clary has done for the last several years, just myopically focusing on, like, how do we leverage AI to improve forecast accuracy? It's pretty darn good. Pretty darn good at, at, at an aggregate level. So a number of, a number of sales leaders that, you know, run their business off of that. And we pretty much consistently beat, beat what the leaders are forecasting because they're usually a little pie in the sky. That's a start, right?

But I think that, you know, the crux of your point is where we really want this to get to it, to make like this, the productivity piece scale is at a rep level. I, as a sales leader, am assured that they are doing the very best possible thing that they could do next. And this is always on and it's autonomous and I trust it. And, and the proof to me in that, and these are some of the things that we'll instrument for our clients over time is, and I don't think that they've really seen this elsewhere in the market is the ability, not just to suggest that this much should happen, but log it and measure it because the, because the impact is going to show up, right? That deal either accelerated, you know, close at a higher clip than it typically would based on the, you know, persona or the segment or, or what have you.

And then that teaches the model with your business and your data to successively get better over time. To me, that's really critical to be able to show these are the outcomes that were achieved and be honest about them and the value that you're creating. And that's, and that's the path that we're on. Cool. Yeah. I mean, I think that, that kind of the data, the proof, right. As far as what's working, what's not in the iteration of it. I think that's the whole thing with, I think the failure of CRM in the early days and still quite frankly is it was always a stick, not a carrot when it came to the rep, right? It was, I had to track this stuff so I didn't get yelled at. And if I, you know, so I, you know, where's your forecast, how many activities, but it was never brought back to the rep that if you track it this way, we're going to be able to come back to you with insights to improve your skill, whatever it might be and bring that insights.

And so I think that's the hope for AI is that it can iterate and learn and then self improve and then give the coaching on the back end to say, okay, yeah, you did it that way. But this time based on that close loss, close one, these are the accelerators. So this is what you should do. And I think if we can get to that point where it's, it's, you know, the trusted next step is, you know, and that's the balance, right? With the, with the senior reps who doubt it, like, because I've been doing this for 30 years, like me versus the junior reps who don't have the context and just say, yes, yes, okay, that's what I should do. And so there's this, you know, weird kind of transition phase that we're in right now, trying to, to give these kids the context to be able to question and use it the right way and then give the trust to the senior reps to trust what it's telling it.

Yeah, you know, maybe you're never going to change the rep that like always wears that same left sock on the last day of the quarter, you know, like, I totally get that. But this is what I think is actually really cool about, you know, the pace of innovation with AI is that we are now all naturally incented to prove value really, really quickly. People will adopt and go back to like the people who fear AI and who like it. People who like AI are just they're getting benefit from it. You know what I mean? And so like, I think with all of this, if you're able to prove value, you're going to get adoption and then even you know, your, your, your left foot wearing sock guy, you know, is going to use it and you're going to learn really quick.

And we're in this awesome space where it's like, if it's not working or it's not meeting the benchmark, we want to know, we, we know why, and we can do something about it really quickly. It's no longer, we're going to build a product and we're going to launch it in 12 months and we're going to use six squads and no, no, no, no, like we're moving very fast, which just creates its own challenges, but pretty cool time to be alive. Yeah, I love it. All right, let's finish it. What's, what's, what's the top on your list right now, as far as priorities and things you're excited about, like what you personally, what are you working on right now? Yeah, yeah, yeah. Look, I mean, I think, I think I kind of already hit it right there.

Like I am excited about the pace of innovation. I'm excited about the value that we can bring to the market. And, and quite honestly, like, it's just been such a, like an intellectually stimulating role to be able to talk to other go to market leaders that, you know, whether they're part of the SaaS apocalypse, which is overblown. And so I think we're starting to see a little bit for the AI natives, which has its own set of challenges, you know, really getting to hear from everybody about how we're to your t-shirt, figuring it out as we go. It's, it's just been, it's been a ton of fun for me, but, you know, with, with our team, you know, we're really, really focused on how do we provide incremental value to clients, not only through products, but through the service we provide.

And it's like, how do we do that at increasingly fast pace? It's a lot to keep up with. So we keep a really high bar and, and we're learning as we go. Love it. Awesome, Brian. Well, I appreciate the conversation, man. Where can people find out more about what you're working on, what sales loft is doing these days and where you want to point them? Yeah, of course. Well, you can always come to salesloft.com. We just launched a brand new website that like I got tranced out on the other day. It's awesome. So you can check out everything that we're up to, the direction we're heading. You can find us on LinkedIn. You can find me, shoot me an email or friend me on LinkedIn, like, and subscribe. I feel like one of my kids, uh, I've got a five year old, eight year old son, and they like, they, they're not allowed to do YouTube, but they like pretend like they're YouTubers and like, and subscribe.

Anyhow, uh, Brian.com. You can find me. Love it, man. Actually as a sidebar, before we finish up, uh, send me your, after this, send me your, if you're comfortable with, send me your address and your, your kids' names. Cause I wrote a book with my daughter. I don't know if you, it's called, I want to be in sales when I grow up. And, uh, yeah, it's, it's, uh, she was six years old. So it's, uh, it's, uh, it's, uh, it's her journey of selling Girl Scout cookies and what she learned along the way. And then, uh, and we put all money to charity, but, but what we did recently, cause she's now 15, she was six when we wrote this. Um, what, what we're doing now is we have a whole bunch of extra boxes.

So if you're, if you're kids, you can sit, you got two boys. Yeah. Five and eight. Yeah. So, uh, perfect age range. We started another company called the future founder project because we have all these extra books cause the publisher went out of business. So I have all these boxes of books. So what we're doing is called the future founder project. People can sponsor a box for like 500 bucks cause there's 24 books in a box, 20 bucks a piece. Um, that box then goes to a kid between the ages of five and 15 and the kid gets a box of books for 20 that they can sell. They get a hundred dollars seed money to start their little entrepreneurial journey and a packet of different options to start their own little business.

So if you, if you, I'll send you one of these just so you can, you can have it, but also if you want, if, if they're kind of the entrepreneurial sales and want to make some money, have them, uh, I'll send you the link. They can actually register. Those punks in a lemonade stand the other weekend and made 250 bucks in like two hours. Crazy. That's one of, that's one of the entrepreneur things, right? Definitely going to be the entrepreneur. He has no shame. I'll send that over to you. So it's, yeah, it's a fun project, but I'll, if you send me your address, I'll, I'll put a, I'll put one of these books in the mail and have my daughter autographed for you. So, cause she's cool. She's way cooler than me anyways.

That's great. Cool. I appreciate it. I, I, I am a couple of minutes late for a five o'clock. Yeah. I got to bounce here. So everybody. So thank you, Brian, for coming on. I really appreciate it. And, uh, everybody else hopefully enjoyed the conversation as much as I did. And like I said, thank you to all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day's going or how bad you think it went, if you make somebody smile, you know, you had a good day and the world needs a lot more of that right now. So thank you all very much. And I will see you on the other side. Hey, thanks again for listening to the show and for all your support throughout the years.

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