The Exchanges

Q Step one being that Who we sell to, what we're selling, and how we're selling it in terms of, like, the words that we use in articulation. That's founder, and then stage two, it's more plastic. Is that correct? Like, the head of sales can work on that?

A Yeah, so the second thing around the, basically, your selling process, the repeatable thing that everybody dreams about, like, I wanted to demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs, where you have the right to say this is a playbook. Any sales leader says, I got a playbook, I got five AEs, and look at them, like, they're just doing my repeatable process. Look, it is, it may be repeatable for the next month, it will not be scalable as you build more people, because you just don't know, you have to figure out a lot. That's why this, like, playbook word is one that I just think it has all these connotations associated with it, and I think, like, you just have to be practical. Like, the reality is in the first, your first two AEs, there is no playbook. You hire your first head of sales, you're piloting it. You may not even know, is your primary persona here the CIO? Or is it some functional leader, like a VP of HR? You don't know that, and if you don't know that, going after either of those requires a different play. And so, I think that's the danger. A lot of focus on the repeatability. I rather focus on agility.

AI assessment note: “You hire your first head of sales, you're piloting it.”

Q Step one being that Who we sell to, what we're selling, and how we're selling it in terms of, like, the words that we use in articulation. That's founder, and then stage two, it's more plastic. Is that correct? Like, the head of sales can work on that?

A Yeah, so the second thing around the, basically, your selling process, the repeatable thing that everybody dreams about, like, I wanted to demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs, where you have the right to say this is a playbook. Any sales leader says, I got a playbook, I got five AEs, and look at them, like, they're just doing my repeatable process. Look, it is, it may be repeatable for the next month, it will not be scalable as you build more people, because you just don't know, you have to figure out a lot. That's why this, like, playbook word is one that I just think it has all these connotations associated with it, and I think, like, you just have to be practical. Like, the reality is in the first, your first two AEs, there is no playbook. You hire your first head of sales, you're piloting it. You may not even know, is your primary persona here the CIO? Or is it some functional leader, like a VP of HR? You don't know that, and if you don't know that, going after either of those requires a different play. And so, I think that's the danger. A lot of focus on the repeatability. I rather focus on agility.

AI assessment note: “You hire your first head of sales, you're piloting it.”

Q So step one being that who we sell to, what we're selling and how we're selling it in terms of like the word That we use in articulation. That's founder, and then stage two is more plastic. Is that correct? Like the head of sales can work on that?

A Yeah, so the second, the second thing, right, around the basically your selling process, the repeatable thing that everybody dreams about, like I want to just demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs. Wow. Where you can, where you have the right to say, this is a playbook. Any sales leader says, I got a playbook, I got five AEs, and look at them, like, they're just doing my repeatable process. Look, it is, it may be repeatable for the next month. It will not be scalable as you build more people, because you're just not, you just don't know, you have to figure out a lot, right? And so, that's why this, like, playbook word is one that I just think it has all these connotations associated with it, and I think, like, you just have to be practical. Like, the reality is in the first, Your first two AEs, there is no playbook. If you hire your first head of sales, you're piloting it, right? Like, uh, you may not even know if your product really resonates with, I don't know, uh, is your primary persona here the CIO, or is it some functional leader, like a VP of HR, right? That You don't know that, and if you don't know that, the, going after either of those requires a different play, right? And, and so I, I think that's the, that's the danger. It's like a lot of focus on the repeatability. I rather focus on agility.

AI assessment note: “If you hire your first head of sales, you're piloting it, right?”

Q Ok, so like, on, and again, I'm asking dumb questions. How many interviews does it take? Who do I bring into the interviews from the wider team? How should I play those two?

A Yeah, so remember, like, my first step is I'm gonna map all the competencies, right? And so, generally speaking, you're not gonna be able to optimize for, like, 10. In fact, like, for me, like, I would optimize for, like, four to five, right? And each interview, Is designed, each interview slot, right, is designed to test for that specific competency. Now, you can merge it, you can do maybe two in the same one or something, but for, for, in my experience, I want four or five people to have been able to meet someone, and again, each person tests different competency. That's, that's, that's one dimension. Second dimension, um, is, uh, the, the final round for, for me has always been for someone to give a, a demo. I love people giving demos. You can tell so much about how they prepare asynchronous, right? Because here's the thing, like, especially when you're hiring young talent, like no one's super polished. Like there are some people who are super polished, but they may not actually be that good. And so I want to give people a chance and see what, how do they act if you give the time to prepare? Someone may bomb their on the fly interviews, but they may crush. Their prepared demo. All right, or presentation. It doesn't have to be demo. It could just be like a pitch, right? And that tells you that this is someone has potential. If you give them the time and space and training, th…

AI assessment note: “I want four or five people to have been able to meet someone”

Q So step one being that who we sell to, what we're selling and how we're selling it in terms of like the word That we use in articulation. That's founder, and then stage two is more plastic. Is that correct? Like the head of sales can work on that?

A Yeah, so the second, the second thing, right, around the basically your selling process, the repeatable thing that everybody dreams about, like I want to just demystify that first. I don't think you create that playbook until you have at least 20 ramped AEs. Wow. Where you can, where you have the right to say, this is a playbook. Any sales leader says, I got a playbook, I got five AEs, and look at them, like, they're just doing my repeatable process. Look, it is, it may be repeatable for the next month. It will not be scalable as you build more people, because you're just not, you just don't know, you have to figure out a lot, right? And so, that's why this, like, playbook word is one that I just think it has all these connotations associated with it, and I think, like, you just have to be practical. Like, the reality is in the first, Your first two AEs, there is no playbook. If you hire your first head of sales, you're piloting it, right? Like, uh, you may not even know if your product really resonates with, I don't know, uh, is your primary persona here the CIO, or is it some functional leader, like a VP of HR, right? That You don't know that, and if you don't know that, the, going after either of those requires a different play, right? And, and so I, I think that's the, that's the danger. It's like a lot of focus on the repeatability. I rather focus on agility.

AI assessment note: “If you hire your first head of sales, you're piloting it”

Q dive into the traits of those reps. Final impossible question, which will likely, uh, lead to it depends. Um, but, uh, if we think about timing, a lot of founders are like, when the fuck do I hire this head of sales or first sales reps in terms of timing? Again, take us back to that coffee shop. You advising me when, when do I hire? I'm, I don't know.

A Number one, I don't know if your first hiring needs to necessarily has to be sales, right? It can, I, I think a lot of times. I'm just going to say a customer facing person. Right. Could be, could be a little bit more CS than sales could be very sales and kind of, uh, you know, almost like a dev rel kind of a persona if, if you're selling a dev ops product. Uh, but, but I think that is, um. Uh, first clarification, right? It's like, I don't think your first person has to be sales. Just make them customer facing so they can get feedback, serve the customer, and help you make better decisions. Uh, in terms of timing, I think my answer is a little different today than it would have been two years ago. Because today, capital is not that big of an issue, right? Like, these seed rounds are massive. These Series A rounds are massive. And so are the valuations that you have to grow into. They're also massive. And so, like, I, I must, my answer is assuming that you're not that resource constraint. If you're not that resource constraint, spending that much money to hire, like, a junior customer-facing person as early as you can is actually would be my advice. Again, not necessarily drive those revenue, but to get those insights, right? The more customer reps you get and you talk to, the more you'll learn. Uh, and, um, and I think that should be the approach. If you're a project, I'm just…

AI assessment note: “hire, like, a junior customer-facing person as early as you can”

Q What's, what's the answer to that? Because I often, I often have this where it's like, oh yeah, they pushed it, not a priority, bad timing. How do you respond to that? What, why is it bad timing? Like, what would you respond?

A Why is it, why is it, why is it not urgent? And you normally, normally we just end there, because normally the, the, the rep may not actually have the answer. Right. Oh, why is it not urgent? Well, they think that it is the, it is the, uh, always the responsibility of the customer to, to, to make timing work, but hey, it's also part of our job to try to create that urgency. Right. And so you, it's five whys is really not about getting to the answer. I think it's about really like creating the right level of discussion. It's a framework to create the right Conversations. So that you will, through that process, find one or two big, like, core root problems that you can address.

AI assessment note: “it's also part of our job to try to create that urgency”

Q dive into the traits of those reps. Final impossible question, which will likely, uh, lead to it depends. Um, but, uh, if we think about timing, a lot of founders are like, when the fuck do I hire this head of sales or first sales reps in terms of timing? Again, take us back to that coffee shop. You advising me when, when do I hire? I'm, I don't know.

A Number one, I don't know if your first hiring needs to necessarily has to be sales, right? It can, I, I think a lot of times. I'm just going to say a customer facing person. Right. Could be, could be a little bit more CS than sales could be very sales and kind of, uh, you know, almost like a dev rel kind of a persona if, if you're selling a dev ops product. Uh, but, but I think that is, um. Uh, first clarification, right? It's like, I don't think your first person has to be sales. Just make them customer facing so they can get feedback, serve the customer, and help you make better decisions. Uh, in terms of timing, I think my answer is a little different today than it would have been two years ago. Because today, capital is not that big of an issue, right? Like, these seed rounds are massive. These Series A rounds are massive. And so are the valuations that you have to grow into. They're also massive. And so, like, I, I must, my answer is assuming that you're not that resource constraint. If you're not that resource constraint, spending that much money to hire, like, a junior customer-facing person as early as you can is actually would be my advice. Again, not necessarily drive those revenue, but to get those insights, right? The more customer reps you get and you talk to, the more you'll learn. Uh, and, um, and I think that should be the approach. If you're a project, I'm just…

AI assessment note: “hire a junior customer-facing person as early as you can is actually would be my advice”

Q think people consistently under, uh, underappreciate what it takes to go outbound effectively. I, I think, well, one area that I would love to dig into in particular, though, is, is really the relationship between head of sales and the CEO. For me, as the first time CEO, what should that ideal relationship look like, and what can I do to get the best out of my head of sales?

A Yeah, my relationship with CEOs is super important, and for me, it's, it's more a partnership, right? Like, I, my job is to bring in, I gotta bring in the, I gotta bring home the bacon. I gotta get, get the cash in, right? I get that. But there's a bigger play here, which, that I, I have in my head, which is, I see one of the, an equally important part of my responsibility as a CRO, head of sales, whatever, is to help my CEO make the best decisions that he or she can. And to do that, that means that I need to, I am responsible to bring back the right amount and type and in the right form of feedback, right, uh, to my CEO so that he or she can make the best decisions. It's my responsibility to make sure that I and my team don't have recency bias, right, based on the last deal that wasn't able to close. Like, it's my job to make sure that the CEO knows what's working and what's not working. For the purpose of his or her decision making. And so, uh, I think it's really important. I, and, and to do that.

AI assessment note: “for me, it's, it's more a partnership, right?”

Q Okay, so we're gonna hire someone really early. I, I embraced a chunky ass seed round at a ridiculous price, so I'm just like everyone else in market right now. Um, and, uh, I need to hire these first reps. How do I structure the process? What does the interview stage look like? Can you walk me through this?

A Uh, well, number one, right? You mentioned process. I think it's extremely important. I think, and the reason why is, um, Number one reason I think is actually, if you, over time, if you care about diversity on your team, you want to get your initial hires right. Because so much of hiring comes through referrals and such. And so, like, I think building the right, a process from the start is critical, so that you make sure that you iron out as many potential unbiased, uh, unconscious biases as possible. And through that process, I think number, number one, be really clear about what you're looking for. I'd be really clear about what are the competencies and the behavioral traits that I think the characteristics that you want to test for. Random number to make it really clear. What are the questions that we are using to assess them? And what does a great answer look like? What does a mediocre answer look like? Right?

AI assessment note: “be really clear about what are the competencies and the behavioral traits”

Q well. We're an early stage startup. We're sub a million in ARR. What, um, I know it's difficult because there's nuance, but if we think back to those, what are we looking for? What, what sort of things would you say we should all be looking for? And then what questions would you say are brilliant or you always like to really tease out whether that person has those characteristics?

A Yeah. So I'm not going to talk about like the obvious stuff. Right, which is, like, someone has to be, someone has to, you know, like, be, be converted and, you know, be hungry and all that. Oh, I think the things that I, like, I, I always look for in whether you're a leader or just any of my customer-facing folks. Number one, uh, reverence for the product. I, I think there's a, there's a, there's a, you can tell when someone really appreciates the product, the intricacies, what it can do. And I think nowadays, especially in a increasing, you know, PLG is on the rise. You want this, I want this person to convey this passion and this love for the product to their customers, as opposed to just following some playbook. And so that reference for your, your product or a, or for any kind of product is something I look for.

AI assessment note: “Number one, uh, reverence for the product.”

Q think people consistently under, uh, underappreciate what it takes to go outbound effectively. I, I think, well, one area that I would love to dig into in particular, though, is, is really the relationship between head of sales and the CEO. For me, as the first time CEO, what should that ideal relationship look like, and what can I do to get the best out of my head of sales?

A Yeah, my relationship with CEOs is super important, and for me, it's, it's more a partnership, right? Like, I, my job is to bring in, I gotta bring in the, I gotta bring home the bacon. I gotta get, get the cash in, right? I get that. But there's a bigger play here, which, that I, I have in my head, which is, I see one of the, an equally important part of my responsibility as a CRO, head of sales, whatever, is to help my CEO make the best decisions that he or she can. And to do that, that means that I need to, I am responsible to bring back the right amount and type and in the right form of feedback, right, uh, to my CEO so that he or she can make the best decisions. It's my responsibility to make sure that I and my team don't have recency bias, right, based on the last deal that wasn't able to close. Like, it's my job to make sure that the CEO knows what's working and what's not working. For the purpose of his or her decision making. And so, uh, I think it's really important. I, and, and to do that.

AI assessment note: “for me, it's, it's more a partnership... help my CEO make the best decisions”

Q well. We're an early stage startup. We're sub a million in ARR. What, um, I know it's difficult because there's nuance, but if we think back to those, what are we looking for? What, what sort of things would you say we should all be looking for? And then what questions would you say are brilliant or you always like to really tease out whether that person has those characteristics?

A Yeah. So I'm not going to talk about like the obvious stuff. Right, which is, like, someone has to be, someone has to, you know, like, be, be converted and, you know, be hungry and all that. Oh, I think the things that I, like, I, I always look for in whether you're a leader or just any of my customer-facing folks. Number one, uh, reverence for the product. I, I think there's a, there's a, there's a, you can tell when someone really appreciates the product, the intricacies, what it can do. And I think nowadays, especially in a increasing, you know, PLG is on the rise. You want this, I want this person to convey this passion and this love for the product to their customers, as opposed to just following some playbook. And so that reference for your, your product or a, or for any kind of product is something I look for.

AI assessment note: “Number one, uh, reverence for the product.”

Q Okay, so we're gonna hire someone really early. I, I embraced a chunky ass seed round at a ridiculous price, so I'm just like everyone else in market right now. Um, and, uh, I need to hire these first reps. How do I structure the process? What does the interview stage look like? Can you walk me through this?

A Uh, well, number one, right? You mentioned process. I think it's extremely important. I think, and the reason why is, um, Number one reason I think is actually, if you, over time, if you care about diversity on your team, you want to get your initial hires right. Because so much of hiring comes through referrals and such. And so, like, I think building the right, a process from the start is critical, so that you make sure that you iron out as many potential unbiased, uh, unconscious biases as possible. And through that process, I think number, number one, be really clear about what you're looking for. I'd be really clear about what are the competencies and the behavioral traits that I think the characteristics that you want to test for. Random number to make it really clear. What are the questions that we are using to assess them? And what does a great answer look like? What does a mediocre answer look like? Right?

AI assessment note: “be really clear about what are the competencies and the behavioral traits”

Q What's, what's the answer to that? Because I often, I often have this where it's like, oh yeah, they pushed it, not a priority, bad timing. How do you respond to that? What, why is it bad timing? Like, what would you respond?

A Why is it, why is it, why is it not urgent? And you normally, normally we just end there, because normally the, the, the rep may not actually have the answer. Right. Oh, why is it not urgent? Well, they think that it is the, it is the, uh, always the responsibility of the customer to, to, to make timing work, but hey, it's also part of our job to try to create that urgency. Right. And so you, it's five whys is really not about getting to the answer. I think it's about really like creating the right level of discussion. It's a framework to create the right Conversations. So that you will, through that process, find one or two big, like, core root problems that you can address.

AI assessment note: “It's a framework to create the right Conversations.”