The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Brendon Cassidy argument clarity score 3.8/5 from 25 exchanges on raw tape · average scores: directness 4 · coherence 3.8 · precision 3.7 · compression 3.1 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Should the founders be the one to do the playbook? Like, to create the first playbook?

A Yes, the, the principles of the playbook? Yeah, for sure. Like, the broad stroke, the outline, whatever you want to call it, right? With, but don't fill it in with, uh, with permanent eight. But sure, you should have a sketched out and say, hey, here are the things that's worked. Here are the plays that work. This is how we do it. This is how we run it. If you're going to be in as the first salesperson, you'll probably have seen it. You'll have seen them in action multiple times. Ultimately, the playbook, um, the in ink should probably be written by the VP of sales, but yeah, you should have a, you know, sort of a loosely built playbook as a founder. I mean, I'm a co-founder. We, we closed a hundred percent, you know, we just became profitable in my startup. We close all of our own deals, myself and the co-founder. We don't have any salespeople. Well, other than us.

AI assessment note: “Yes, the, the principles of the playbook? Yeah, for sure.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q So what do you do if you don't have a network? What if you do if you don't know the five?

A So if you have investors, quote, hypothetically, you have some access to some sort of network. So if you have investors, that's one place to start. Although investors are notoriously bad hiring recommenders. I'm sure I know you're different, but most, most investors and VCs like They make a recommendation, and my advice would be like, just, just, just, no. Like, it's great that they work, you know, that you were on the board of a company 15 years ago, and they were great then, and stuff, but like, um, so I would say, yeah, like, if, if you don't have investors that can recommend good people, and you don't have your own network, I would get Advisors or influencers in your space, right? Um, that have, you know, and make them partners, you know, give them equity and maybe pay them because their, their recommendation probably has more credibility than your own company, right? Um, their voice has more visibility than you. And so go out and create a five person advisory team. That's, you know, that's great.

AI assessment note: “I would get Advisors or influencers in your space... create a five person advisory team.”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q What are the biggest things we need to unlearn with sales teams?

A I think the, like, let's spend 10 dollars to make a dollar and how we go to market and how we build, go to market and sales organizations is over. Maybe that will be, maybe that will be a thing again someday, but it's no way to run a business anymore. And so you can't do it that way, right? And every single, I mean, as you know, right, you talk to startups every day. Every startup is, is laser focused on breakeven and profitability and long-term sustainability. And you can't, you know, the customer, the cat costs of five years ago are not, not even considerable, right? Um, the entire outbound go-to-market SDR model has collapsed in the last five years, three years, um, and it doesn't work anymore. Um, a lot of the ways that we have traditionally done sort of like mark sort of marketing demand generation have long since not worked. And so, yeah, it's, it's everyone's sort of in the, a lot of people are in the space of, okay, what now that's, that's my general state of the state. You, and so you have every, every hire has to be like a Ted X, you know, a Ted X scrapper.

AI assessment note: “the entire outbound go-to-market SDR model has collapsed in the last five years”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q Do you ever hire people who haven't been reps before where you can coach them and they have the aptitude and skills, but they haven't been reps before?

A Obviously I want to hire a network for my first three to five hires. Um, you know, people that are ideally someone, at least one that has worked for me before, where I know that whatever the conditions are on the ground, like they've seen it before and they can, they can live in that world. Like once you get beyond that, then, then I'm mostly focused on like aptitude and talent. You're trying to find talent and coachability and ambition and work ethic, um, versus like, oh, this guy was a sales force for 10 years. I, I won't ever hire that person in a startup generally, right? Because there's no, no comparable motion, right? Versus I, I'm selling for a Fortune 1000 tech company. Everyone knows who we are. Everybody has budget. Um, you know, versus you get on a call and there's no acknowledgement that there's even a problem. Like, the problem that you want to solve, there's no agreement or even understanding that that problem exists. Can you live in that world? Um, where you have to, you know, you have to convince them it's a, it's a legitimate problem. Um, to even examine, like, There's no comps there for like Salesforce or Oracle or Adobe or whatever, right? You don't ever have to make that kind of case there ever.

AI assessment note: “once you get beyond that, then, then I'm mostly focused on like aptitude and talent.”

Answered raw tape D 4 · C 4 · P 5 · Cm 4 4.25

Q How do you incentivize them financially and are sales reps coin operators?

A I think that's one of those, that's a super fluid concept, right? Because I think the way that we've compensated salespeople like five years ago is probably like null and void now. Um, obviously I don't, I'm not paying any salespeople right now. Like, um, we're, you know, we're founders. We close deals. We're not paying ourselves commission for those. Um, I would say the Echosign model. Is a great model for times like this, right? Which was pay of really high percentage after they paid for the, after they paid for themselves, essentially, right? Um, and so, um, every sales rep, that's how we did it. Every sales rep had a, like, full, full operational cost, you know, of like, this is what they, this is their salary and benefits, and this is what it costs. And so, if you closed a 100,000 dollar deal and your cost was 15 K a month, We just took 15 K off, so you paid for yourself. And then once you paid for yourself, we paid like, 15% after that. I mean, it probably averages out to something more normal, but like, that was the way we looked at it was, um, you know, because we were, we were not bootstrapped, but I mean, we only raised like, five million dollars, I think, in the lifetime of the company, so, and none after I joined. And so, like, every, you know, we wanted to make salespeople profitable as fast as possible, and one of the best ways to make them profitable was to Make …

AI assessment note: “pay of really high percentage after they paid for themselves”

Answered raw tape D 5 · C 5 · P 3 · Cm 3 4.20

Q Brendan, how do you analyze where we're at in the sales playing field today? We got on the call and you said, you know, ah, navigating today. How do you analyze where we're at today?

A I think the way I would analyze it is, you know, anything Anything, 24 months or older, right? That we're in a, it's, we're in a space of clay, you know, of putty, and, and basically most of what we knew is off the books, has no relevance anymore, um, to how we go to market, to how we build sales teams, um, SDR teams, everything is, we're very much in a place where it's like, the more you can unlearn You're, the more that you can walk away from bad habits and things that we thought were true that aren't anymore, the better off we're all going to be, um, which is not a, not a comfortable place to be for most.

AI assessment note: “most of what we knew is off the books, has no relevance anymore”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q What are the biggest things we need to unlearn with sales teams?

A I think the, like, let's spend 10 dollars to make a dollar and how we go to market and how we build, go to market and sales organizations is over. Maybe that will be, maybe that will be a thing again someday, but it's no way to run a business anymore. And so you can't do it that way, right? And every single, I mean, as you know, right, you talk to startups every day. Every startup is, is laser focused on breakeven and profitability and long-term sustainability. And you can't, you know, the customer, the cat costs of five years ago are not, not even considerable, right? Um, the entire outbound go-to-market SDR model has collapsed in the last five years, three years, um, and it doesn't work anymore. Um, a lot of the ways that we have traditionally done sort of like mark sort of marketing demand generation have long since not worked. And so, yeah, it's, it's everyone's sort of in the, a lot of people are in the space of, okay, what now that's, that's my general state of the state. You, and so you have every, every hire has to be like a Ted X, you know, a Ted X scrapper.

AI assessment note: “the entire outbound go-to-market SDR model has collapsed in the last five years”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q Should the founders be the one to do the playbook? Like, to create the first playbook?

A Yes, the, the principles of the playbook? Yeah, for sure. Like, the broad stroke, the outline, whatever you want to call it, right? With, but don't fill it in with, uh, with permanent eight. But sure, you should have a sketched out and say, hey, here are the things that's worked. Here are the plays that work. This is how we do it. This is how we run it. If you're going to be in as the first salesperson, you'll probably have seen it. You'll have seen them in action multiple times. Ultimately, the playbook, um, the in ink should probably be written by the VP of sales, but yeah, you should have a, you know, sort of a loosely built playbook as a founder. I mean, I'm a co-founder. We, we closed a hundred percent, you know, we just became profitable in my startup. We close all of our own deals, myself and the co-founder. We don't have any salespeople. Well, other than us.

AI assessment note: “Yes, the, the principles of the playbook? Yeah, for sure. Like, the broad stroke”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q Onboarding. You kind of need to give them time, and you need training. If I'm a founder, what's the right way to onboard new sales reps to ensure that I'm not jumping in? We can't expect them to hit the ground running from day one. How do we onboard reps the right way?

A If you're a founder, and you have a founder-led sales motion, you know, they need to just be at your hit at every turn, right? Every, you know, every sales call you're on, You know, probably for a few, like a couple weeks, right? Where there's not a lot of expectation put on them, but like, you know, I mean, there's in a startup osmosis is, is the best way to learn, right? So, you know, have them on your hip. Obviously you're using gong or something like that, right? So you have, you should have a bank of call recordings and demos and, you know, very easy way to like, Analyze and synthesize that data. You should, you know, have your salesperson listen to, like, every sales call, like, within reason, right, or that would be relevant to the type of sales cycles they'll be running. I mean, obviously, like, right now, sales training is not something that people are going to spend a lot of money on, I think, generally. Um, so, yeah, I would say osmosis. Um, you know, don't have them, you know, without it. You know, it's, they're almost certain to fail, certainly. And that's, you know, obviously I was involved in the very, in the early days of Gong. That is, that is something that's out there now. I think that's critical for onboarding new salespeople, right?

AI assessment note: “they need to just be at your hip at every turn, right?”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q What are the signs that it's not working out?

A I always felt like if I'm on calls with them and I feel like I have to take the call over, you know, and run it for them, you know, like at some point they should, that's what first step is like, can they run the call in the way that you want it done without where you can be involved and help in, in on the margins, but you don't have to run the call. That's pretty important. A lot of the sales hires I've had that didn't work out I felt like, I'm like, I have to jump in here, because it's going sideways a lot, and I have to take over and fix it, and it's just not, it doesn't seem to, you know, they don't seem to be getting better at it. Um, and then, you know, like, obviously, like, I've, you know, I believe in running, like, really, like, sort of a monthly, tight monthly, um, Sort of process. No, Matt, really quite frankly, no matter what your ASP is, that's just what I believe in the startup is the right thing to do because it, it's, it makes it really hard for them to push deals out and say, oh yeah, I got, that's a verbal commit for three months from now. Um, well that's not, that's not a verbal commit. It's just, that's a best case deal. And that's the timeframe. It's a best case deal. And but like, you know, when you in, uh, you know, you have, you run a, a tight sales process without Too many stages where deals can hide in.

AI assessment note: “if I'm on calls with them and I feel like I have to take the call over”

Answered raw tape D 4 · C 4 · P 4 · Cm 4 4.00

Q Do you agree with fire fast when it comes to raps?

A If that's your philosophy and everyone's getting fired fast or first or whatever, then there's probably something wrong that's maybe not all them. Um, and so, if you believe in the hire you made, I don't think you need, I don't think there needs to be a, like, artificial timeline on it. Um, but like, yeah, I'd say a quarter, you know, a quarter plus some change, you should start to see things going, you know, and like, we would always say by the second quarter, you wanna, you wanna, by the end of the second quarter, you wanna fully ramp salesperson. And if you don't see that, if you finish their first quarter, And they fall short, and you're in the second court, and you don't see them tracking towards that, then

AI assessment note: “I don't think there needs to be a, like, artificial timeline on it.”

Answered raw tape D 4 · C 4 · P 4 · Cm 4 4.00

Q Do you agree with fire fast when it comes to raps?

A If that's your philosophy and everyone's getting fired fast or first or whatever, then there's probably something wrong that's maybe not all them. Um, and so, if you believe in the hire you made, I don't think you need, I don't think there needs to be a, like, artificial timeline on it. Um, but like, yeah, I'd say a quarter, you know, a quarter plus some change, you should start to see things going, you know, and like, we would always say by the second quarter, you wanna, you wanna, by the end of the second quarter, you wanna fully ramp salesperson. And if you don't see that, if you finish their first quarter, And they fall short, and you're in the second court, and you don't see them tracking towards that, then

AI assessment note: “I don't think there needs to be a, like, artificial timeline on it.”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q Brendan, how do you analyze where we're at in the sales playing field today? We got on the call and you said, you know, ah, navigating today. How do you analyze where we're at today?

A I think the way I would analyze it is, you know, anything Anything, 24 months or older, right? That we're in a, it's, we're in a space of clay, you know, of putty, and, and basically most of what we knew is off the books, has no relevance anymore, um, to how we go to market, to how we build sales teams, um, SDR teams, everything is, we're very much in a place where it's like, the more you can unlearn You're, the more that you can walk away from bad habits and things that we thought were true that aren't anymore, the better off we're all going to be, um, which is not a, not a comfortable place to be for most.

AI assessment note: “most of what we knew is off the books, has no relevance anymore”

Answered raw tape D 4 · C 4 · P 4 · Cm 3 3.85

Q What are the signs that it's not working out?

A I always felt like if I'm on calls with them and I feel like I have to take the call over, you know, and run it for them, you know, like at some point they should, that's what first step is like, can they run the call in the way that you want it done without where you can be involved and help in, in on the margins, but you don't have to run the call. That's pretty important. A lot of the sales hires I've had that didn't work out I felt like, I'm like, I have to jump in here, because it's going sideways a lot, and I have to take over and fix it, and it's just not, it doesn't seem to, you know, they don't seem to be getting better at it. Um, and then, you know, like, obviously, like, I've, you know, I believe in running, like, really, like, sort of a monthly, tight monthly, um, Sort of process. No, Matt, really quite frankly, no matter what your ASP is, that's just what I believe in the startup is the right thing to do because it, it's, it makes it really hard for them to push deals out and say, oh yeah, I got, that's a verbal commit for three months from now. Um, well that's not, that's not a verbal commit. It's just, that's a best case deal. And that's the timeframe. It's a best case deal. And but like, you know, when you in, uh, you know, you have, you run a, a tight sales process without Too many stages where deals can hide in.

AI assessment note: “if I'm on calls with them and I feel like I have to take the call over”

Answered raw tape D 4 · C 4 · P 4 · Cm 3 3.85

Q So what do you do if you don't have a network? What if you do if you don't know the five?

A So if you have investors, quote, hypothetically, you have some access to some sort of network. So if you have investors, that's one place to start. Although investors are notoriously bad hiring recommenders. I'm sure I know you're different, but most, most investors and VCs like They make a recommendation, and my advice would be like, just, just, just, no. Like, it's great that they work, you know, that you were on the board of a company 15 years ago, and they were great then, and stuff, but like, um, so I would say, yeah, like, if, if you don't have investors that can recommend good people, and you don't have your own network, I would get Advisors or influencers in your space, right? Um, that have, you know, and make them partners, you know, give them equity and maybe pay them because their, their recommendation probably has more credibility than your own company, right? Um, their voice has more visibility than you. And so go out and create a five person advisory team. That's, you know, that's great.

AI assessment note: “go out and create a five person advisory team.”

Answered raw tape D 4 · C 4 · P 4 · Cm 3 3.85

Q Do you ever hire people who haven't been reps before where you can coach them and they have the aptitude and skills, but they haven't been reps before?

A Obviously I want to hire a network for my first three to five hires. Um, you know, people that are ideally someone, at least one that has worked for me before, where I know that whatever the conditions are on the ground, like they've seen it before and they can, they can live in that world. Like once you get beyond that, then, then I'm mostly focused on like aptitude and talent. You're trying to find talent and coachability and ambition and work ethic, um, versus like, oh, this guy was a sales force for 10 years. I, I won't ever hire that person in a startup generally, right? Because there's no, no comparable motion, right? Versus I, I'm selling for a Fortune 1000 tech company. Everyone knows who we are. Everybody has budget. Um, you know, versus you get on a call and there's no acknowledgement that there's even a problem. Like, the problem that you want to solve, there's no agreement or even understanding that that problem exists. Can you live in that world? Um, where you have to, you know, you have to convince them it's a, it's a legitimate problem. Um, to even examine, like, There's no comps there for like Salesforce or Oracle or Adobe or whatever, right? You don't ever have to make that kind of case there ever.

AI assessment note: “once you get beyond that, then, then I'm mostly focused on like aptitude and talent”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q An ultimate one. What would you most like to change about the world of sales?

A The stuff I'm working on is a passion project for me. Um, because I've just seen that the, that go to market model for startups is so daunting. There's just so much noise you're competing against that the traditional ways to Get in front of customers is changing and maybe change forever. And so, yeah, that's, you know, I just, yeah, the world I want to see is a world where you're starting out your sales process as close to the customer as possible as a way to sort of mitigate a lot of risk in how startups grow. That's the thing I believe most in, right, is that going to market on the backs of You know, like a sort of let's just go crank out a 100,000 emails and make a thousand calls. I never really believed in it. It was like one of those things that everyone just kind of had to like, okay, yeah, yeah, yeah, yeah, we'll do that.

AI assessment note: “the world I want to see is a world where you're starting out”

Answered raw tape D 5 · C 3 · P 3 · Cm 3 3.60

Q Do you agree with Jason in hiring two sales reps at a time?

A Generally, but again, it's, it's a case-by-case basis. If you hired I mean, that, the, the advantage, certainly echo sign did that back in the day, you know, back in the day, which I would say the climate echo sign was in much more like today than five years ago, right? Like we were, you know, just coming out of the subprime meltdown from an economic standpoint. Things weren't great. Um, we were definitely like, you know, trying, you know, we didn't want to raise another dime of funding. And so we were trying to grow or get, you know, we were trying to drive profitability through growth, right? Efficient growth. Ideally, I mean, one of the advantages of hiring two is you can hire two different types of people. Um, and you know, like, cause you don't know exactly like what kind of, and I mean, there's all sorts of, uh, sub various sub context to that, uh, that I think Change the equation a little bit. Like, are you hiring people, you know, right? Like, you know, like I believe personally, you know, for my first five sales hires, I would never hire somebody out of network ever. Um, I either like somebody that I know and someone that's worked for me or somebody that's vouched for by somebody I trust. Um, those would be because those are foundational hires. You really can't afford to get those wrong and you can't afford to compete against any other company that's Subscribing to Zip…

AI assessment note: “Generally, but again, it's, it's a case-by-case basis.”

Partly raw tape D 3 · C 4 · P 4 · Cm 3 3.55

Q Dude, I, I look like frickin' Benjamin Button, but tell me, how do you, how did you first make your way into the world of sales, and when did you realize you loved sales?

A I was sort of coming into the tech world, uh, around like, 1919 99. 2000 was the beginning of my career, which is hard to believe I've actually been around that long. I started my career as a recruiter, so this is before the dot-com bubble burst, which there's not a lot of people that have that as a reference point today. I was a recruiter, we worked with venture-backed companies, Sort of around sort of helping them build their leadership and management teams. That was really my first job out of college. Came in at sort of the height of it, and then the entire market collapsed. And then recruiting became literally the first thing, you know, that's the first, oh, recruiting fees? Yeah, that's just, yeah. That's not even, there's not, that's a five second discussion. And so, that became like, you know, an incredible career experience because it was like survive. Okay, how do we survive doing this? Because no one needs it. Certainly nobody wants to pay for it. Everyone's firing people. No one's hiring people. Um, what now? Um, and so that forced all of us. We're all really young and a lot of people, um, sort of didn't make it. Uh, but the, those of us that did, um, it's, you know, I can't imagine, you know, it's so foundational in my career, um, that it's, you know, I can't imagine not having gone through it.

AI assessment note: “I started my career as a recruiter, so this is before the dot-com bubble”

Answered raw tape D 3 · C 4 · P 4 · Cm 3 3.55

Q How do you incentivize them financially and are sales reps coin operators?

A I think that's one of those, that's a super fluid concept, right? Because I think the way that we've compensated salespeople like five years ago is probably like null and void now. Um, obviously I don't, I'm not paying any salespeople right now. Like, um, we're, you know, we're founders. We close deals. We're not paying ourselves commission for those. Um, I would say the Echosign model. Is a great model for times like this, right? Which was pay of really high percentage after they paid for the, after they paid for themselves, essentially, right? Um, and so, um, every sales rep, that's how we did it. Every sales rep had a, like, full, full operational cost, you know, of like, this is what they, this is their salary and benefits, and this is what it costs. And so, if you closed a 100,000 dollar deal and your cost was 15 K a month, We just took 15 K off, so you paid for yourself. And then once you paid for yourself, we paid like, 15% after that. I mean, it probably averages out to something more normal, but like, that was the way we looked at it was, um, you know, because we were, we were not bootstrapped, but I mean, we only raised like, five million dollars, I think, in the lifetime of the company, so, and none after I joined. And so, like, every, you know, we wanted to make salespeople profitable as fast as possible, and one of the best ways to make them profitable was to Make …

AI assessment note: “once you paid for yourself, we paid like, 15% after that.”

Partly raw tape D 3 · C 3 · P 3 · Cm 2 2.85

Q Final one for you. What one company sales strategy have you been most impressed by recently?

A Certainly rippling. I think pretty impressive what they've done. Um, you know, the CRO used to work on, was on our team at EchoSign back in the day. Matt Plank has done an amazing job there rippling. Um, so that would be the one number one, and certainly there's a lot of people on that rippling team I know, and there's a lot of talent on that rippling team. Um, which is one of the advantages, like, when you're the one company just crushing it in a down market. Is you can get, you can really just build super teams talent wise. And I think they have everyone else is like companies that have adjusted to, you know, the state of the state.

AI assessment note: “Certainly rippling. I think pretty impressive what they've done.”

Redirected raw tape D 2 · C 3 · P 3 · Cm 2 2.55

Q Is there a good reason to lose a deal in your mind?

A And usually when you lose deals, it's, it's, it's not about, it's what you didn't do, you know, five steps prior, right? Or what you didn't establish or, you know, There's all sorts of stuff when you try to do a post-mortem on it, where you can look back and you can say, here are the things, yeah, we really didn't solidify these things. There were stones unturned, um, is usually when you do, when you analyze why you lost a deal. And so, we were always, you know, our motto was always like, let's turn over every stone. We were so good at That we could walk into deals where we were basically, you know, given a blindfold and a cigarette at the beginning of the sales cycle, right? Where our competitor had us beat in 10 waves to Sunday. They were in the deal. They had vent, they had partner and vendor support. They had everything imaginable, um, where we could You know, we could undo it. Out of that, certainly that EchoSign team, one of the things that we did, I think at a, which was not the norm at that time, maybe it is now, is we were selling, we were in every layer of the deal, right? We were at this, we were in the C-suite, we were with the evaluators and decision makers, even users, right? If there was some sort of proof of concept or pilot. And we were going against DocuSign, and DocuSign was maybe at one level in a deal. One level, and we were at three levels, and we were, yo…

AI assessment note: “when you lose deals, it's, it's, it's not about, it's what you didn't do”

Answered raw tape D 3 · C 2 · P 3 · Cm 2 2.55

Q Do you agree with Jason in hiring two sales reps at a time?

A Generally, but again, it's, it's a case-by-case basis. If you hired I mean, that, the, the advantage, certainly echo sign did that back in the day, you know, back in the day, which I would say the climate echo sign was in much more like today than five years ago, right? Like we were, you know, just coming out of the subprime meltdown from an economic standpoint. Things weren't great. Um, we were definitely like, you know, trying, you know, we didn't want to raise another dime of funding. And so we were trying to grow or get, you know, we were trying to drive profitability through growth, right? Efficient growth. Ideally, I mean, one of the advantages of hiring two is you can hire two different types of people. Um, and you know, like, cause you don't know exactly like what kind of, and I mean, there's all sorts of, uh, sub various sub context to that, uh, that I think Change the equation a little bit. Like, are you hiring people, you know, right? Like, you know, like I believe personally, you know, for my first five sales hires, I would never hire somebody out of network ever. Um, I either like somebody that I know and someone that's worked for me or somebody that's vouched for by somebody I trust. Um, those would be because those are foundational hires. You really can't afford to get those wrong and you can't afford to compete against any other company that's Subscribing to Zip…

AI assessment note: “Generally, but again, it's, it's a case-by-case basis.”

Redirected raw tape D 3 · C 2 · P 3 · Cm 2 2.55

Q Does that not only worsen when you think about AI's impact on outbound?

A That's an extraordinarily fluid discussion. Um, I think ultimately what AI does is probably get put the SDR function back under marketing. Ultimately, when you can maybe accomplish the tasks of multiple in one with one, um, I think a lot of the problems we have today You can loosely trace back to, like, the total shift from demand gen being in the hands of marketing and, um, into sales from marketing, which has been a 10 plus year shift, and that's, I, I can tell you no great VP of sales is ever going to take a job with a company that's dependent on an outbound go-to-market model to grow. That's just, nope. Bye-bye. It's, it's, and they may be more, uh, circumspect with a founder and, And telling them why they're not coming, but behind the scenes with other sales leaders, they're going to be like, not even close because they know the, the, they know it's probably a fait accompli at that point. That company is probably not going to make it. And so more and more companies, right? Like I, I've, I talked to You know, I've probably advised 60 SaaS companies in the last 10 years. You talk to many, many founders, and the question I ask is like, why'd you start this company, right? What was the problem that you wanted to solve? And a lot of people can't answer, they can't, they can't answer the question. And to me, it's like, I can't even fathom anybody actually starting a software com…

AI assessment note: “I think ultimately what AI does is probably get put the SDR function back under marketing.”

Redirected raw tape D 2 · C 2 · P 3 · Cm 2 2.25

Q Does that not only worsen when you think about AI's impact on outbound?

A That's an extraordinarily fluid discussion. Um, I think ultimately what AI does is probably get put the SDR function back under marketing. Ultimately, when you can maybe accomplish the tasks of multiple in one with one, um, I think a lot of the problems we have today You can loosely trace back to, like, the total shift from demand gen being in the hands of marketing and, um, into sales from marketing, which has been a 10 plus year shift, and that's, I, I can tell you no great VP of sales is ever going to take a job with a company that's dependent on an outbound go-to-market model to grow. That's just, nope. Bye-bye. It's, it's, and they may be more, uh, circumspect with a founder and, And telling them why they're not coming, but behind the scenes with other sales leaders, they're going to be like, not even close because they know the, the, they know it's probably a fait accompli at that point. That company is probably not going to make it. And so more and more companies, right? Like I, I've, I talked to You know, I've probably advised 60 SaaS companies in the last 10 years. You talk to many, many founders, and the question I ask is like, why'd you start this company, right? What was the problem that you wanted to solve? And a lot of people can't answer, they can't, they can't answer the question. And to me, it's like, I can't even fathom anybody actually starting a software com…

AI assessment note: “what AI does is probably get put the SDR function back under marketing”

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