The Exchanges

Q the best sales teams do to beat the others in a competitive space? What are just a couple of things that they do That you're like, crap, they want, they won that deal again and again, but their product actually isn't better. What are a couple quick insights that we can wrap that you see the best folks do that just the good or the mediocre don't do as well?

A Um, I think the best sales or in like competitive selling just have this Just crystal clear black and white understanding of why, you know, why, why do we, why should we win? What are the reasons that we should win and beat them in a deal? And what are the reasons that they, that they should beat us? Right. And, and so they know, you know, like, you know, what all the sort of You know what their playbook is, you know, what your playbook is, and then you sort of understand that it's going to be, it's a battle, you know, it's a battle for a mindset. Like, certainly at Ecosign who said, hey, we know if the deal's about this, we win, and we know if the deal's about these other 20 things, That it could be about, we know that they would, right? So we, we just said, we are going to make this entirely about this. Everything that happens in the sales cycle will be centered around this narrative, and we will not, we will not be pushed off that mark at any point. Um, and that, you know, and so the other guys were like, Hey, we have all this other stuff. And we're like, none of it matters. The only thing that matters is this. Um, and so I think that's the, I think realizing what your, not just what your strengths are, but what your weaknesses are, and then weaponizing that before your, your competitor exposes it as a liability, right? Taking, why do, why should we lose? Okay, we, if we kno…

AI assessment note: “just have this Just crystal clear black and white understanding of why”

Q No, it's almost always worse if they've, if they've done well and they leave, it's almost always worse, right?

A They've done well. If, if, if you're, yeah, if they've done well and you bring somebody in and they come in and they're like, yeah, I'm coming in here to basically tell this person that I'm better than he or she is and that I can get better people in here than he or she did. Yeah, then that's, that's over, right? Um, and by the way, they can't, right? The amount of like, you know, sort of sweat equity and intellectual capital that's been built there with that team is not replaceable most of the time. Um, and so, yeah, that, that would be one learning. I don't know that there's a massive sample size to support it, but like, you know, I, I think that's, I think it's real, you know?

AI assessment note: “The amount of like, you know, sort of sweat equity and intellectual capital”

Q you, how do you, and when and how do you have that conversation with your VPs of sales and others? Is it, is it a regular check-in? Do you spring it on them? That, that one, the springing on them, I think is always, is suboptimal than having had a check-in, right? Um, but folks also, folks, folks react to it. They have emotional reactions in many cases too, right?

A Yeah, I mean, it, it's, if I think If you're a founder or CEO that has some experience, right, because if you have no experience, it's probably going to be hard to know unless you have some really smart people around you with a lot of experience on how to handle it, but like, yeah, earlier, the earlier, the better. Like, I don't, you know, I feel like, you know, you can say, hey, like, I'm, you know, love everything you're doing, and I feel like, you know, we're on this great track to get to twenty million, and I feel like beyond that, here are the things that I think are things we need to, right? Like, these aren't things that I don't think you, that I don't think you can do. There are things I want to know that you can do. Um, and I think these are some of the areas that we, you know, we want to be prepared for at twenty million, right, that indicate that all of us can take the next step. Yeah. That's, that's how I'd have the conversation.

AI assessment note: “the earlier, the better. Like, I don't, you know, I feel like”

Q scenarios, both for an executive and this founders are when you have someone on your team and it's clear. You need someone above them. Uh, you have a VP of sales. You need a CRO. You need a CMO. We can talk about sales in particular, and you had an interesting insight about how that's changed and maybe what's your general advice on handling phase transitions, right? As you scale.

A I mean, yeah, I mean, there's obviously there's different scenarios of, of, When and why you're talking to somebody, right? Like sometimes it's because you guys have done incredibly well, right? And it's like, we want to go to the next step and we want to go public and, you know, we just think having somebody with more experience there, you know, will help us in those areas, but we don't want to really change almost anything we're doing kind of day to day. And I think in those scenarios, um, it's super important to keep, you know, keep your, keep the people there that did it, built it and happy. Um, so I'll use an example. So when the CRO for Gong went there, um, you know, uh, He came in, he would, he had been on LinkedIn and he's like, what one piece of advice would you give me? And I said, just make Jameson happy. That's the piece of advice. I mean, he's got this incredible team. They're incredibly loyal to him. Right. And like, just, you know, make him feel, you know, make him feel good, set up for success and all the rest, because there's, you know, there's not, you know, it's working really well. Right. And so you look at that team, they're all there. Right. That they're all that they're all there. All the people that built it, the sales worker there. And so I, I give that Ryan's CRO. I give a lot of credit. Uh, I would look at outreach was another example, right? It's all…

AI assessment note: “it's super important to keep, you know, keep your, keep the people there that did it”

Q So I think that's an interesting insight. You should be running, you got to run all these playbooks. You just have to add to the playbooks. Because their efficacy has decayed, right?

A Yeah, it's, there's sort of three, you know, three eras. I look at it, you have like, and they're all, they're all in parallel, really, but like, you have marketing, you have sort of the marketing demand era. You can't just do that. Now you need to do sort of outbound or brute force and our, and, you know, our belief is, and you know, that, that will, that, that will, That'll be proven right or wrong over time is that, you know, sort of referral selling is like the last, you know, referrals and introductions is sort of the last untapped channel there. Right. Um, and so that's, that's our belief, but like, yeah, I mean, it's certainly been the last five or six years. You know what, one thing I was saying to somebody the other day that they completely disagreed with me on by the way, and actually took personal, Took it personally and like got upset at me about it.

AI assessment note: “referral selling is like the last, you know, referrals and introductions is sort of”

Q Yeah, that maybe that's the meta point. I was initially teasing on inflation and maybe higher OT expectations for the same attainment, but the meta issue is with so many SaaS startups that are successful, the best folks are more risk averse, right, in many cases, right, or they're just, they're delaying. I think ten million is the new one million in terms of risk for many folks, isn't it?

A For sure. And like, you know, there's a lot of people doing now what I was doing like four years ago, right, five years ago, right, which was like, You know, you can, you can have a sort of, a sort of part, part-time or sort of advisory or consulting role with a lot of different companies. Um, and, and first off, do really well and not have a lot of risk, professional risk in that. Um, a lot of people are doing that. Um, hopefully I, I don't want to be a, Hey, Brendan start. I don't, I don't know, I don't know that I started that trend, but there's a lot of people doing it. There's a lot less, I'd say a lot more people who are less experienced that you can say, Hey, like, huh? You know, like, usually it's somebody that's had like, you know, some sort of big exit or win or multiple wins or whatever it is, but. You know, the, their, you know, brand is currency, and like, you know, there's a lot of people that have, have created really strong brands as like, you know, thought leaders, but yeah, so those people, you know, there's a lot of opportunity for those people. They're super risk averse, um, and it's, if they were to ask me, hey, should I be risk averse? I'd say, yeah, you should. Generally, right?

AI assessment note: “They're super risk averse, um, and it's, if they were to ask me... I'd say, yeah”