The Exchanges

Q All right. I can buy that. So then there's thousands of these people. It's bigger than we think. Great. What a relief. Uh, I was getting worried there. Um, so how do we source them? We get a G sheet out, and what does that look like?

A Yeah, so, so maybe, and I'll try and do this, um, throughout our conversation. Here's what I see most folks doing. What I see most folks doing, so Harry, you are an exceptional founder. Um, you were, uh, number one at your class, in your class at Stanford in computer science, and, uh, you, you maybe were like, you know, the, the CTO at a great startup prior to joining. Your background is not sales. Your personal network is not sales. It's engineering. You know, so you've got recruiting your first set of engineers became easy for you. It was just like your, your Stanford classmates that, uh, you were friends with and it was folks that you worked with that, uh, rippling prior to starting your company. Okay. But now it's time to hire salespeople. You, you, you aren't close with salespeople. This is not your personal network. What most or many folks do is they, they leverage something like an external recruiter and, you know, they have a recruiter send them Uh, candidates that they look at their resumes and then they interview them and they spend a bunch of time, uh, uh, on interviews with potential sales candidates. And the reality is that the best, these people that you were talking about, Ari, how many of these people do exist? Do they exist in the world? Most of them do not go through a third party recruiter. They want to go somewhere where their reputation precedes them a litt…

AI assessment note: “sourcing by leveraging your personal network is just of the utmost importance.”

Q ways. Um, so yes. Okay. So we're there. Um, any advice to me on, I'm, I'm loving kind of this chronology. So we, we've got these two. Um, we want to make them an offer. Any advice on sales comp, Sam? I've got no idea. I'm, I'm giving these two wraps. It's the first time I've hired them. What's the right way to approach sales comp for the first two?

A You know, I think for the, for the early ones, I think you probably just have a conversation around just like, what are your comp expectations? You're probably going in with an idea of what you believe is market rate for the hire that you are making. Let's just say like, you know, at maturity, you think this sales rep is going to be able to close something like a million dollars in ARR. We're a mid market sale. Um, you know, and we can, we can afford to pay somebody in this role. Let's call it 200 K. Uh, you know, we're early stage. Sorry to give a bit more equity. We think ballpark is going to be like a 160 K total comp. That's like, you know, where we think it is. Harry, you're the candidate. Um, you know, what are your comp expectations? Well, Sam, today I'm at one 80. My company is a little bit bigger. I would, um, You know, I, I would take a little bit of a hit there and he, you know, you go in at, at one 60 and you give them a bit more of the equity off the company, but I think, um, it's not one size fits all. You don't have an idea based off of how much revenue you think a sales rep could generate at maturity. AE range, 100 to two 50 is, is like the AC, uh, is the, um, uh, total comp, uh, for, uh, a sales rep. So wide range there based on a number of factors.

AI assessment note: “I think you probably just have a conversation around just like, what are your comp expectations?”

Q you mentioned like, oh, People get 10 emails a day, and I think they're about to get a hundred emails a day, and I think they're about to get a hundred text messages a day, and 50 WhatsApps. I see so many WhatsApp sales tools now as well. AI is gonna Massively increase the amount of outbound sent. Will we see the commoditization of outbound with the rise of AI?

A I think that what I'm seeing is the tools today are making, uh, the, the, the category of outbound or the function of SDR or AE more effective in the same way that something like, or, or they're streamlining. A lot of manual process. The same way that something like, you know, outreach did a number of years ago. Erie, when I joined, EchoSign is an SDR. Marketo existed, but I was manually sending all of these emails one at a time. I like copy it, paste it, and then I'd like put it in somebody's name, and then I'd hit send. Um, but it was a very manual process, and along comes outreach, And I'm able to send like a hundred at a time. And that allowed me to, you know, be far more efficient as an SDR, but it didn't get rid of the function of SDR. In fact, like maybe there are more SDRs in a world where outreach exists than there were before. And, you know, I think we're continuing down this path of automated, you know, now we can personalize emails. The, the AI is going to write me an email that knows things about Harry that I wouldn't even be able to find out if I spent a bunch of time researching it. So, you know, the AI is going to write me copy as well. I think what, at least today, AI does not accomplish that humans still do is this, this, um, aspect of being creative. You know, the, the AI isn't going to tell you here is your contrarian or unconventional outbound sales campaig…

AI assessment note: “AI does not accomplish that humans still do is this, this, um, aspect of being creative.”

Q Sam, what's your biggest hiring mistakes? Everyone makes mistakes. My mother always tells me I was one.

A Your brother has very high expectations because you're crushing it here. Okay. Um, I think my biggest hiring mistakes were pretending that concerns that I had in the interview, uh, uh, at hiring process didn't really exist in sales in particular. Uh, you know, it, it is performance based. Um, but it's also like the, the team dynamic is so important, like this concept of building a winning culture and, and having people that are positive influences on their peers. You cannot have folks that sort of sit around and complain about the product or complain about marketing Or whatever the, like, complaint of the day is. Because it rubs off on their peers, and before you know it, you have just, like, an unhappy sales floor where one person is negatively impacting the broader team. And I have probably rehired or hired people where, you know, this concern had been flagged, where it's like, you know, they hit quota, but there, there is some serious baggage, uh, that, that comes along with this person. It's like, oh, they hit quota. We need to hire 10 people. Come on, like join. And, and so, you know, that's one example, but I think it's, it's pretending That things that were concerns in the interview process didn't really exist because like, either they were coming from this place or I, I, I just put that again, be sort of blinded. And then those things oftentimes come to manifest, uh, an…

AI assessment note: “my biggest hiring mistakes were pretending that concerns that I had in the interview”

Q you mentioned like, oh, People get 10 emails a day, and I think they're about to get a hundred emails a day, and I think they're about to get a hundred text messages a day, and 50 WhatsApps. I see so many WhatsApp sales tools now as well. AI is gonna Massively increase the amount of outbound sent. Will we see the commoditization of outbound with the rise of AI?

A I think that what I'm seeing is the tools today are making, uh, the, the, the category of outbound or the function of SDR or AE more effective in the same way that something like, or, or they're streamlining. A lot of manual process. The same way that something like, you know, outreach did a number of years ago. Erie, when I joined, EchoSign is an SDR. Marketo existed, but I was manually sending all of these emails one at a time. I like copy it, paste it, and then I'd like put it in somebody's name, and then I'd hit send. Um, but it was a very manual process, and along comes outreach, And I'm able to send like a hundred at a time. And that allowed me to, you know, be far more efficient as an SDR, but it didn't get rid of the function of SDR. In fact, like maybe there are more SDRs in a world where outreach exists than there were before. And, you know, I think we're continuing down this path of automated, you know, now we can personalize emails. The, the AI is going to write me an email that knows things about Harry that I wouldn't even be able to find out if I spent a bunch of time researching it. So, you know, the AI is going to write me copy as well. I think what, at least today, AI does not accomplish that humans still do is this, this, um, aspect of being creative. You know, the, the AI isn't going to tell you here is your contrarian or unconventional outbound sales campaig…

AI assessment note: “AI does not accomplish that humans still do is this, this, um, aspect of being creative”

Q All right. I can buy that. So then there's thousands of these people. It's bigger than we think. Great. What a relief. Uh, I was getting worried there. Um, so how do we source them? We get a G sheet out, and what does that look like?

A Yeah, so, so maybe, and I'll try and do this, um, throughout our conversation. Here's what I see most folks doing. What I see most folks doing, so Harry, you are an exceptional founder. Um, you were, uh, number one at your class, in your class at Stanford in computer science, and, uh, you, you maybe were like, you know, the, the CTO at a great startup prior to joining. Your background is not sales. Your personal network is not sales. It's engineering. You know, so you've got recruiting your first set of engineers became easy for you. It was just like your, your Stanford classmates that, uh, you were friends with and it was folks that you worked with that, uh, rippling prior to starting your company. Okay. But now it's time to hire salespeople. You, you, you aren't close with salespeople. This is not your personal network. What most or many folks do is they, they leverage something like an external recruiter and, you know, they have a recruiter send them Uh, candidates that they look at their resumes and then they interview them and they spend a bunch of time, uh, uh, on interviews with potential sales candidates. And the reality is that the best, these people that you were talking about, Ari, how many of these people do exist? Do they exist in the world? Most of them do not go through a third party recruiter. They want to go somewhere where their reputation precedes them a litt…

AI assessment note: “sourcing by leveraging your personal network is just of the utmost importance.”