The Exchanges

Q How long is this three-stage process number one, and when do we allow these new reps to speak to their first customers?

A I feel like two months is reasonable at this stage. To get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a reasonable flow of inbound, or you're an open source company where you can like start tapping to a community, I think within three weeks, they can start talking to customers. They may not need to be selling because again, I just want to hire some good customer facing people at first. So that in the beginning, they might just be talking to existing customers, just be like checking in. What do you love about the product? What do you like about the product? What's your issues? It's like, get more reps. I do think it's important to get reps, but just because you're telling the customers at that point doesn't mean you're truly ready yet. So this is the difference, one difference between a PLG company and non-PLG companies. You can actually start doing that, and it helps with accelerating their ramp.

AI assessment note: “I feel like two months is reasonable at this stage.”

Q Oliver Jay, one of the most successful sales leaders of the last decade. Most recently, OJ spent six years as CRO at Asana and grew the team from less than 20 to over 450. Before Asana, OJ spent four years at Dropbox, where he was head of APAC and LATAM. So Oliver, as a founder or a sales leader, how do I structure the onboarding for each new sales hire?

A We're talking about like you're still early stage. So I would do product first, market second, and sales last. Product first. In the beginning, you're not going to have a full-fledged sales team where you have SEs, sales engineers who can handle the technical things. You may not even know what gotchas you have in your, whatever data model your company was built on. In the beginning, I think it's super important that whatever customer facing people you hire, they have to play that role. They have to go Two orders of magnitude deeper on the technical side of the product, whether it's talking about the security, the infrastructure with like a CISO or CIO, then kind of your future A's. I think in the beginning, it's really important to build that product knowledge. A lot of times the best way to do that is actually get the team exposed to support because the tickets that you get coming in is basically a reflection of what you're likely sales obstacles that you're going to get. So you want to be able to talk about it, understand. Number one.

AI assessment note: “I would do product first, market second, and sales last.”

Q Oliver Jay, one of the most successful sales leaders of the last decade. Most recently, OJ spent six years as CRO at Asana and grew the team from less than 20 to over 450. Before Asana, OJ spent four years at Dropbox, where he was head of APAC and LATAM. So Oliver, as a founder or a sales leader, how do I structure the onboarding for each new sales hire?

A We're talking about like you're still early stage. So I would do product first, market second, and sales last. Product first. In the beginning, you're not going to have a full-fledged sales team where you have SEs, sales engineers who can handle the technical things. You may not even know what gotchas you have in your, whatever data model your company was built on. In the beginning, I think it's super important that whatever customer facing people you hire, they have to play that role. They have to go Two orders of magnitude deeper on the technical side of the product, whether it's talking about the security, the infrastructure with like a CISO or CIO, then kind of your future A's. I think in the beginning, it's really important to build that product knowledge. A lot of times the best way to do that is actually get the team exposed to support because the tickets that you get coming in is basically a reflection of what you're likely sales obstacles that you're going to get. So you want to be able to talk about it, understand. Number one.

AI assessment note: “I would do product first, market second, and sales last.”

Q That is very, very kind of you. I've been looking forward to this one, but I want to start with some context. So you've worked in some of the most incredible hypergrowth companies from Dropbox to Asana. Tell me, how did you make your way into sales and come to lead some of these incredible sales orgs?

A Well, you know, I first couple of years in my, in my career was in finance. I, I, I was in first starting equity research at Morgan Stanley at covering tech companies. That was my first exposure to how the sort of the intersection of tech and business. Uh, then I went over to venture, uh, and, and I worked at NEA for a bit, uh, love, love my time there. In that experience, I really saw how amazing some Uh, investors were basically sort of leveraging their operating background to help founders. So I got that curious about operating and all the GPs I really admired. They were like, hey, you should operate. And if you're going to operate, you either build product or you sell product. Everything else is supporting one of those two. And I was like, oh, interesting. And, and just one thing led to another. I just, it was like, 50, 50. I went down the sales path and that was the, that was the path I ended up on.

AI assessment note: “I went down the sales path and that was the path I ended up on.”

Q love that kind of simplicity of you either build or you sell. Um, I do want to ask that, you know, when we look back at the time, six years Asana, four years Dropbox at pivotal moments of scaling for both companies, when you think back to that, and if you isolate one or two key takeaways from each, what would you say they would be looking back and reflecting?

A So Dropbox, I think for me, number one is that, uh, technology is just fundamentally different, uh, adopted differently in businesses, B to B businesses, Uh, are no longer by the traditional top down way in terms of how technology is used in, in companies, uh, employees get to pick, right? And that started with Apple with the iPhone and probably around, what, 2000 and 2000 10, right? When people had this BYOD move and Dropbox was the, was the company that shattered and started the BYOA move. And so that, I think that's number one. And so that was the result. Number two is that You know, PLG is fundamentally is a very different kind of go to market than traditional BW sales. I think that's the main thing I took from Dropbox. Had the opportunity to then apply that to Asana. And I think what I learned at Asana was if I had to pick one thing, it would be this concept of prior to like growth sales and traditional enterprise sales. You know, when I first joined Asana, and even today, when I talk to a lot of people, I think there is this predominant view of that. You can, you have to pick one or the other. And at Asana, we pioneered and we, we, we try to do both at the same time. And, and I think the results were quite positive. And I think my takeaway is that it is possible. Uh, it's hard, but it's possible.

AI assessment note: “Dropbox, I think for me, number one is... what I learned at Asana was”

Q Okay, let's, let's, sorry, let's go down that then. I mean, I've got loads of questions for you, uh, but when you say you rather focus on agility, double down there, what do you mean about, by that?

A I'd rather focus on, instead of like, hey, trying to get people to, like, write up some playbook, uh, hey, actually be really nimble. This month, we're gonna focus, right, on answering these questions, right? Let's focus on which persona actually resonates most with our product. Does our product resonate with most, right? And let's, this month, let's do a deep dive and sprint and like really focus there. Take that learning. Alright, next month. Let's learn what does it take to engage with some of these people, right? Is it, is it through a referral, uh, uh, program that we should do this? Is it cold outbounding? Is it, um, you know, do we, do we can, can we cold email these people? Right? Like, because I'll tell you some personas you can't, some probably not so much, right? Okay. After you answer these questions, then you can piece it together. That is very, very obvious. Uh, so that's, that's what I mean by agility. When I'm hiring my first. Leader, first couple of people, I'm not telling them to come back with Uh, a playbook. I'm telling them to come back with learnings and insights.

AI assessment note: “I'm not telling them to come back with Uh, a playbook. I'm telling them to come back with learnings”

Q on the show who say, always start with a head of sales. They can then hire the team that they want and build their rep base. And then others say, hey, get jack of all trades reps in and roll with the first iteration of the playbook. Where do you advise me as a founder, Early stage seed series A. Do I hire wraps first or head of sales first?

A Depends. As you, like, most of my answers always depends. Sometimes that's what I'm like, OJ, what's your playbook? I'm like, well, it depends. Ok, so that's how I think about it. If you are, if your product and your business is going after an existing category and you're just a much better version of it, right? So there's already, sometimes already budget, but certainly it's pretty clear who the buyer is and what, what are you solving? I would lean towards hiring a head of sales. Because that tells me that you, you probably can, uh, grow faster. You're probably on the higher, fast hiring scaling path, like soon, in the near future, and so hire a good head of sales, like, can, can really accelerate things. On the other hand, if you're trying to actually create a new category, right, what you're selling is fundamentally the first piece of that kind of software solving that admit problem at a company, I think you're better off with hiring some, Hungry and smart customer facing people first. Why? Again, talk about that playbook thing. That you gotta learn. You gotta learn. Who are you actually selling to? What should be your motion? Like, are you, should you go enterprise? Should you go top down? Should you go bottoms down? Up? Should you go middle? Down? Up? You know? And so, uh, Only after that will you actually know what to look for in a head of sales, right? Uh, and so I think…

AI assessment note: “existing category... I would lean towards hiring a head of sales.”

Q a playbook, they don't have anything to execute on, they don't hit numbers because they don't have a playbook to work against, they churn, and morale sucks, and that's very, very bad and toxic to get out of. How am I wrong, then, if the playbook isn't created till much later on? How would you change my advice? I actually need help here, because I use that advice a lot.

A Uh, I would say, look, you need to, you need to start with something, right? You need to, like, and the founder, for the founder have gotten enough traction to raise a seed or a round, they must have had some, enough traction, uh, to have something to start with, right? And so I think you can call that your first playbook. I think, I think playbooks should be dynamic. And so it should be something where. Okay, hey, I hired my first two, three AEs. They may be junior people. You're gonna, you're gonna start with this. Right, but I also expect you to make it better constantly. Right. Tell me how, how to actually be more effective. How do you improve this part of the funnel? How do you improve this messaging? Right. Go test out these different copies and you tell me what's, what makes better. And I think that playbook, instead of thinking about it as a V two or V three, it's just, it's constantly improving. It should be improving every single week. And so I would rather make, as a founder, I would say, Hey, Like, I want you to close with, you know, drive revenue, drive logos. I also want you to bring me insights. Every week, how can we make, kind of, the V-one playbook better?

AI assessment note: “you need to start with something... call that your first playbook”

Q difference there between PLG and non-PLG, you know, in terms of for new reps, um, often when it's PLG, they just have a lot of inbound to, to service and it's, it's, It's a lot more on a plate bluntly. When that plateaus, you said before to me that you can't just kind of go outbound. What did you mean by this, like not being able to just go outbound?

A Yeah, yeah, I see this pattern everywhere. Uh, so let me just start by saying it's like. I love PLG. I breathe and bleed PLG. At the same time, I love outbound. Outbound's way easier. It's like, it's like, I, I love going outbound, ok? But I think going out, for outbound to be successful, generally speaking, you're selling to a different buyer. Probably a more senior persona. You're probably selling a different value. Uh, and so therefore you need different messaging. In terms of the sales process, absolutely, you'll have a much lower conversion rate. And to make it for that, your deal size needs to be commensurately bigger. And generally speaking, that will require a different type of talent to execute that. So what I see a lot happening is sometimes people's initial inbound thing goes, you hit that S curve. It's amazing. And then suddenly it just like starts plateauing. You're like, what the heck is going on? I don't know. The answer I always hear is, well, we're just going to start going outbound now. Again, outbound is fine. But if what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people. It won't gonna work because your entire conversion process is designed around a different buyer, articulating a different value, right? Converting at a higher speed and a smaller deals. So if you…

AI assessment note: “It won't gonna work because your entire conversion process is designed around a different buyer”

Q And then, so we've got, we've got the kind of first, they're in customer support and they're in support. Second, they're going through the decks, they're understanding the market, the competition. Third being sales, the last component. What, what is involved in that third component being the sales orientation?

A Yeah. My, my guess is if you're hiring your first couple of people, right. It is like you're, you're, you're shadowing the founder on a couple of conversations. I think absolutely. You go talk to your top 10 customers and you develop a relationship there. And these are probably pretty friendly customers and, and really ask like, Hey, you start asking like the questions around like, Hey, how you can even ask customer like, how, like, We haven't written case study yet, but like, how, how would you quantify the value that we provided to you, right? Uh, you probably have to do that because no one has done that yet. If it hasn't done that. So you basically shadow the founder for a little bit. Um, and then what I do is like, it culminates for me. This is where I mentioned a demo earlier. Like you may not need to do a demo during an interview process. Absolutely. I want someone to demo the product at the end of whatever onboarding period you designate as reasonable. Um, and it is in this, and like, this is kind of like a. The equivalent of a PhD defending their thesis. For me, you're coming in, you're gonna, you're, you're going to present your demo of our product. And we are going to actually role play and, and, and I invite, it would be like, you know, if I'm the founder, right, and we found one founder, it would be a. PM. Right. And like whatever the other people, the other two, th…

AI assessment note: “you're shadowing the founder on a couple of conversations”

Q to a lot of founders, and we're kind of diving straight in, kind of ignoring schedule, but I speak to a lot of founders today who are like, well, you know, if we have product-like growth, we, we don't need a sales team because the product sells itself. How do you respond and advise those founders? At what point does it asymptote or plateau? How do you think about that?

A Well, I think it depends a little bit on your product category and who you're trying to sell to, right? Uh, there are some categories where you can get really far with a self-serve only model. I'm thinking about Atlassian and how far they went in the sort of in that DevOps world. It makes total sense, right? No developer really wants to get on a phone or get cold call or whatever, even take, pick up a phone call from a random sales person. Makes a ton of sense. Almost every other persona. Sales make sense, right? To compliment, not to say that you have to lead with sales, but sales can really help you move up, uh, and get to the larger, more strategic conversations. So I think it depends on your product. Uh, but generally speaking, I think the decision to not have sales, you're just missing out on a lot of potential growth.

AI assessment note: “the decision to not have sales, you're just missing out on a lot of potential growth.”

Q How do you test that? And so are we going to do it one by one? So we're in the interview. What questions do you ask to tease out whether they have that reference product?

A Yeah, so what I'm looking for in most of my answers is not your answer, but how you answer. So in this case, I will ask you to tell me about your product. Tell me about your product. Very simple. And you will see, there's like, either it's like, oh my, it's amazing. Let me tell you all the amazing, like lives it has changed because it was able to do this and this and this. It is by far the best, right? Then you have the other ones. They just, they give you the playbook. They, they treat you like you are, you're in a, you know, they cold calls you and you're like, I accept. Tell me about your product, please. And then they go, okay, we are a platform for. Increasing the efficiency of your for logistics and it is just like, you'll see there's is your passion. For the product itself, or is there just passion for. Executing a generic thing you can, it's like, it's very obvious, right? Um, so it's the how it's not the, it's not the question.

AI assessment note: “I will ask you to tell me about your product.”

Q My final one, my favorite is, um, we lost our champion, so there was nothing that we could do internally. It's just that, you know, the person who wanted it left. How would you, like, analyze that with the five whys? Like, why didn't we have a broader base of supporters?

A Yeah. Well, exactly. Like, yeah, you know, start, I would start with like, why does person leave? Sometimes this person left, you know, and you realize that you were actually always talking to the wrong person. So when you, right. Okay. Why did we have more time? Why weren't we multi multi-threaded is the, is the lingo. Why weren't we multi-threaded in this account? Right? Uh, oh, usually it's like, oh, we just, you know, then we usually, it's just like, we didn't get to it. But then it stops there. But it's interesting to be like, why didn't we get through it? It could be like, oh, well, we didn't get through because we have so many freaking accounts. Right? And so what you realize that, oh, you need to actually work on a prioritization system. As opposed to being, oh, well, we didn't do it. Okay, we should do it next time.

AI assessment note: “I would start with like, why does person leave?”

Q Okay, let's, let's, sorry, let's go down that then. I mean, I've got loads of questions for you, uh, but when you say you rather focus on agility, double down there, what do you mean about, by that?

A I'd rather focus on, instead of like, hey, trying to get people to, like, write up some playbook, uh, hey, actually be really nimble. This month, we're gonna focus, right, on answering these questions, right? Let's focus on which persona actually resonates most with our product. Does our product resonate with most, right? And let's, this month, let's do a deep dive and sprint and like really focus there. Take that learning. Alright, next month. Let's learn what does it take to engage with some of these people, right? Is it, is it through a referral, uh, uh, program that we should do this? Is it cold outbounding? Is it, um, you know, do we, do we can, can we cold email these people? Right? Like, because I'll tell you some personas you can't, some probably not so much, right? Okay. After you answer these questions, then you can piece it together. That is very, very obvious. Uh, so that's, that's what I mean by agility. When I'm hiring my first. Leader, first couple of people, I'm not telling them to come back with Uh, a playbook. I'm telling them to come back with learnings and insights.

AI assessment note: “I'm telling them to come back with learnings and insights.”

Q a playbook, they don't have anything to execute on, they don't hit numbers because they don't have a playbook to work against, they churn, and morale sucks, and that's very, very bad and toxic to get out of. How am I wrong, then, if the playbook isn't created till much later on? How would you change my advice? I actually need help here, because I use that advice a lot.

A Uh, I would say, look, you need to, you need to start with something, right? You need to, like, and the founder, for the founder have gotten enough traction to raise a seed or a round, they must have had some, enough traction, uh, to have something to start with, right? And so I think you can call that your first playbook. I think, I think playbooks should be dynamic. And so it should be something where. Okay, hey, I hired my first two, three AEs. They may be junior people. You're gonna, you're gonna start with this. Right, but I also expect you to make it better constantly. Right. Tell me how, how to actually be more effective. How do you improve this part of the funnel? How do you improve this messaging? Right. Go test out these different copies and you tell me what's, what makes better. And I think that playbook, instead of thinking about it as a V two or V three, it's just, it's constantly improving. It should be improving every single week. And so I would rather make, as a founder, I would say, Hey, Like, I want you to close with, you know, drive revenue, drive logos. I also want you to bring me insights. Every week, how can we make, kind of, the V-one playbook better?

AI assessment note: “I think playbooks should be dynamic... it's just, it's constantly improving.”

Q on the show who say, always start with a head of sales. They can then hire the team that they want and build their rep base. And then others say, hey, get jack of all trades reps in and roll with the first iteration of the playbook. Where do you advise me as a founder, Early stage seed series A. Do I hire wraps first or head of sales first?

A Depends. As you, like, most of my answers always depends. Sometimes that's what I'm like, OJ, what's your playbook? I'm like, well, it depends. Ok, so that's how I think about it. If you are, if your product and your business is going after an existing category and you're just a much better version of it, right? So there's already, sometimes already budget, but certainly it's pretty clear who the buyer is and what, what are you solving? I would lean towards hiring a head of sales. Because that tells me that you, you probably can, uh, grow faster. You're probably on the higher, fast hiring scaling path, like soon, in the near future, and so hire a good head of sales, like, can, can really accelerate things. On the other hand, if you're trying to actually create a new category, right, what you're selling is fundamentally the first piece of that kind of software solving that admit problem at a company, I think you're better off with hiring some, Hungry and smart customer facing people first. Why? Again, talk about that playbook thing. That you gotta learn. You gotta learn. Who are you actually selling to? What should be your motion? Like, are you, should you go enterprise? Should you go top down? Should you go bottoms down? Up? Should you go middle? Down? Up? You know? And so, uh, Only after that will you actually know what to look for in a head of sales, right? Uh, and so I think…

AI assessment note: “existing category... I would lean towards hiring a head of sales”

Q when it's less, um, solid in terms of its packaging, that may be the rep route. On the rep route, Jason Lampkin always says, hey, hire two reps at a time, kind of, Pit them against each other, kind of, um, Hunger Games style. Um, do you agree with that suggestion, and how do you think about creating competition and urgency in those first reps that you bring on board?

A Yeah. I don't, is, uh, gosh, I would love to talk to Jason live about this and can understand exactly what, what, what, what he had in mind. I, you know, for me, there are elements I like that. I agree there are elements that I would not agree, like based on, you know, the, the snippet, right. Um, that you just mentioned, I agree you should hire in batches. If you have the privilege to be able to time your hiring in this environment that where it's so hard to hire, uh, good people. If you can bash them, great, right? Lots of benefits, onboarding, you know, right? You can actually like, kind of, uh, uh, have a basic AP test. Uh, I, I think though, a couple of things around competition. I think if you really need to rely on sort of like having people with the same cohort to drive competition, I think you may have hired the wrong people in my opinion, right? Uh, because in that early stage, I'm actually trying to foster more than anything, a culture of collaboration. I want us to learn. I want us to co-create that playbook together. And so if I hire the right people, I will hire people who are intrinsically competitive and hate being, not being number one, that I don't need to manufacture that environment. Everyone should want to intrinsically want to be number one. I don't need to overtly make it even more so. If anything, I want people to actually come together and, uh, and work…

AI assessment note: “in that early stage, I'm actually trying to foster more than anything, a culture of collaboration.”

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 Any other big mistakes? Any other big nudges or pieces of advice?

A Specifically on sales comp. Well, I think it would be a mistake not to, not to give equity. I think sometimes it's, I don't know why, but sometimes I talk to founders and I feel like they treat sales people as second class citizens because they feel like the product can sell itself. And so, you know, why should sales and they're just like so incredibly cheap on the equity part. Um, huge mistake. And it may sound obvious, but like, Let me explain a little bit more why it's a big mistake. Over time, many companies will want to build sales teams that scale and you need that customer relationship, right? Uh, that, that sales and CS team, you know, personnel can help you drive. In my experience, your first 20 people you hire, they are the heart and soul of the team. These are the people who understand the intricacies of the product, they understand who to go to on the product team, on the engineering team, if things are off, they understand how things are done. And these are also the people who you will end up sending as ambassadors around the world. To start local offices, right? Because you want to keep a cohesive culture and such. And so these initial people, like I I've seen, I've seen situations where there it's a, it's more of a transactional relationship between the company and the initial salespeople. So people do well, I mean, as well, that's great. And then they, and then …

AI assessment note: “I think it would be a mistake not to, not to give equity.”

Q And then, so we've got, we've got the kind of first, they're in customer support and they're in support. Second, they're going through the decks, they're understanding the market, the competition. Third being sales, the last component. What, what is involved in that third component being the sales orientation?

A Yeah. My, my guess is if you're hiring your first couple of people, right. It is like you're, you're, you're shadowing the founder on a couple of conversations. I think absolutely. You go talk to your top 10 customers and you develop a relationship there. And these are probably pretty friendly customers and, and really ask like, Hey, you start asking like the questions around like, Hey, how you can even ask customer like, how, like, We haven't written case study yet, but like, how, how would you quantify the value that we provided to you, right? Uh, you probably have to do that because no one has done that yet. If it hasn't done that. So you basically shadow the founder for a little bit. Um, and then what I do is like, it culminates for me. This is where I mentioned a demo earlier. Like you may not need to do a demo during an interview process. Absolutely. I want someone to demo the product at the end of whatever onboarding period you designate as reasonable. Um, and it is in this, and like, this is kind of like a. The equivalent of a PhD defending their thesis. For me, you're coming in, you're gonna, you're, you're going to present your demo of our product. And we are going to actually role play and, and, and I invite, it would be like, you know, if I'm the founder, right, and we found one founder, it would be a. PM. Right. And like whatever the other people, the other two, th…

AI assessment note: “shadowing the founder on a couple of conversations... talk to your top 10 customers”

Q How long is this three-stage process number one, and when do we allow these new reps to speak to their first customers?

A I'm just like, I have to, like, go back in time to think about this super early stage, right? I feel like two months. Is reasonable, uh, at this stage to, to get to a, to get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a good flow of reasonable flow of inbound, or you're an open source company where you can like sort of tap into a community. I, I think, I think within, within Within three weeks, they can start talking to customers. They may not, they may not need to be selling, right? Because like, again, I just want to hire some good customer facing people at first, so that in the beginning, they might just be talking to existing customers. Just be like checking in. What do you love about the product? What do you like about the product? What's your issues? Right? Just like get more reps. I do think it's important to get, get reps, but just because you're talking to customers at that point doesn't mean you're truly ready yet. So this is the diff one difference between PLG company and non-PLG companies. You can actually start doing that. Uh, and it helps with accelerating the ramp.

AI assessment note: “I feel like two months... Within three weeks, they can start talking to customers.”

Q difference there between PLG and non-PLG, you know, in terms of for new reps, um, often when it's PLG, they just have a lot of inbound to, to service and it's, it's, It's a lot more on a plate bluntly. When that plateaus, you said before to me that you can't just kind of go outbound. What did you mean by this, like not being able to just go outbound?

A Yeah, yeah, I see this pattern everywhere. Uh, so let me just start by saying it's like. I love PLG. I breathe and bleed PLG. At the same time, I love outbound. Outbound's way easier. It's like, it's like, I, I love going outbound, ok? But I think going out, for outbound to be successful, generally speaking, you're selling to a different buyer. Probably a more senior persona. You're probably selling a different value. Uh, and so therefore you need different messaging. In terms of the sales process, absolutely, you'll have a much lower conversion rate. And to make it for that, your deal size needs to be commensurately bigger. And generally speaking, that will require a different type of talent to execute that. So what I see a lot happening is sometimes people's initial inbound thing goes, you hit that S curve. It's amazing. And then suddenly it just like starts plateauing. You're like, what the heck is going on? I don't know. The answer I always hear is, well, we're just going to start going outbound now. Again, outbound is fine. But if what you mean by going outbound is you're just going to get some salespeople to go buy some lists and just start cold emailing, LinkedIn bombing people. It won't gonna work because your entire conversion process is designed around a different buyer, articulating a different value, right? Converting at a higher speed and a smaller deals. So if you…

AI assessment note: “It won't gonna work because your entire conversion process is designed around a different buyer”

Q to a lot of founders, and we're kind of diving straight in, kind of ignoring schedule, but I speak to a lot of founders today who are like, well, you know, if we have product-like growth, we, we don't need a sales team because the product sells itself. How do you respond and advise those founders? At what point does it asymptote or plateau? How do you think about that?

A Well, I think it depends a little bit on your product category and who you're trying to sell to, right? Uh, there are some categories where you can get really far with a self-serve only model. I'm thinking about Atlassian and how far they went in the sort of in that DevOps world. It makes total sense, right? No developer really wants to get on a phone or get cold call or whatever, even take, pick up a phone call from a random sales person. Makes a ton of sense. Almost every other persona. Sales make sense, right? To compliment, not to say that you have to lead with sales, but sales can really help you move up, uh, and get to the larger, more strategic conversations. So I think it depends on your product. Uh, but generally speaking, I think the decision to not have sales, you're just missing out on a lot of potential growth.

AI assessment note: “the decision to not have sales, you're just missing out on a lot of potential growth.”

Q How long is this three-stage process number one, and when do we allow these new reps to speak to their first customers?

A I feel like two months is reasonable at this stage. To get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a reasonable flow of inbound, or you're an open source company where you can like start tapping to a community, I think within three weeks, they can start talking to customers. They may not need to be selling because again, I just want to hire some good customer facing people at first. So that in the beginning, they might just be talking to existing customers, just be like checking in. What do you love about the product? What do you like about the product? What's your issues? It's like, get more reps. I do think it's important to get reps, but just because you're telling the customers at that point doesn't mean you're truly ready yet. So this is the difference, one difference between a PLG company and non-PLG companies. You can actually start doing that, and it helps with accelerating their ramp.

AI assessment note: “two months is reasonable... within three weeks, they can start talking to customers.”

Q How do you test that? And so are we going to do it one by one? So we're in the interview. What questions do you ask to tease out whether they have that reference product?

A Yeah, so what I'm looking for in most of my answers is not your answer, but how you answer. So in this case, I will ask you to tell me about your product. Tell me about your product. Very simple. And you will see, there's like, either it's like, oh my, it's amazing. Let me tell you all the amazing, like lives it has changed because it was able to do this and this and this. It is by far the best, right? Then you have the other ones. They just, they give you the playbook. They, they treat you like you are, you're in a, you know, they cold calls you and you're like, I accept. Tell me about your product, please. And then they go, okay, we are a platform for. Increasing the efficiency of your for logistics and it is just like, you'll see there's is your passion. For the product itself, or is there just passion for. Executing a generic thing you can, it's like, it's very obvious, right? Um, so it's the how it's not the, it's not the question.

AI assessment note: “I will ask you to tell me about your product.”

Q We can switch it up for a different one, which is what would you most like to change about the world of sales?

A Uh, what would I change? I think sales Still today, when people think of sales, they still have this picture of some, some used car salesman image. And I think. Sales people, what sales people do at the core is. They help customers solve their problems. They happen to do that sometimes because. Your product actually does that really well, right? But that is what sales is about. You're solving problems for customers. It's not that different than that of a product manager. It's just how you do about it differently. And so I think a lot of times in tech, frankly, I think sales people are second class citizens. Uh, because they're not building a product and all that, and I think I would love to change that, because I think the best companies are, are, are the ones where sales, collecting customer feedback, working with customers directly, are on equal footing with the, uh, with product.

AI assessment note: “I think sales people are second class citizens... I would love to change that”

Q How do we test that in the interview?

A So I asked for real examples. So if you're a leader, I'll give me, I'll give you an example. So if you're a leader, I'll always ask, I'd like to know, like, give me an example, right? Give me an example of someone whose career you impacted personally, right? And, and you kind of like hear it, and usually everybody has one or two examples, or they're able to, like, Manufacture something. Okay, that seems okay. But again, this is one where, again, you can tell by the passion, right? Someone talking about, oh, my God, Harry. Harry was a disaster when I met him, but, you know, like, he has so much potential. We worked on it, right? Or someone, someone would just like talk more factually. So that's already one, one read. And then I asked another one, which is. And this is the key one, which is, hey, what is, um, uh, uh, and I, I learned this from probably the best interviewer I know, which is this guy called Tony Huey when we were working at Dropbox together. And it was, hey, tell me about someone who you were not able to get, to get them to reach their fullest potential. And again, it's about how they answer for me, right? In terms of reading it, uh, and the people you want are people who take it personally. It's like, it's a personal failure of mine that Harry, I wasn't get, I wasn't able to get Harry to reach so much potential. I saw so much potential, but I wasn't able to get th…

AI assessment note: “give me an example of someone whose career you impacted personally”

Q How long is this three-stage process number one, and when do we allow these new reps to speak to their first customers?

A I'm just like, I have to, like, go back in time to think about this super early stage, right? I feel like two months. Is reasonable, uh, at this stage to, to get to a, to get to a point where like they're really, really solid with like a great demo. They have acquired all this knowledge. That doesn't mean that they can't talk to customers earlier. If you're a PLG company where you have a good flow of reasonable flow of inbound, or you're an open source company where you can like sort of tap into a community. I, I think, I think within, within Within three weeks, they can start talking to customers. They may not, they may not need to be selling, right? Because like, again, I just want to hire some good customer facing people at first, so that in the beginning, they might just be talking to existing customers. Just be like checking in. What do you love about the product? What do you like about the product? What's your issues? Right? Just like get more reps. I do think it's important to get, get reps, but just because you're talking to customers at that point doesn't mean you're truly ready yet. So this is the diff one difference between PLG company and non-PLG companies. You can actually start doing that. Uh, and it helps with accelerating the ramp.

AI assessment note: “I feel like two months. Is reasonable... within three weeks, they can start talking to customers.”

Q My final one, my favorite is, um, we lost our champion, so there was nothing that we could do internally. It's just that, you know, the person who wanted it left. How would you, like, analyze that with the five whys? Like, why didn't we have a broader base of supporters?

A Yeah. Well, exactly. Like, yeah, you know, start, I would start with like, why does person leave? Sometimes this person left, you know, and you realize that you were actually always talking to the wrong person. So when you, right. Okay. Why did we have more time? Why weren't we multi multi-threaded is the, is the lingo. Why weren't we multi-threaded in this account? Right? Uh, oh, usually it's like, oh, we just, you know, then we usually, it's just like, we didn't get to it. But then it stops there. But it's interesting to be like, why didn't we get through it? It could be like, oh, well, we didn't get through because we have so many freaking accounts. Right? And so what you realize that, oh, you need to actually work on a prioritization system. As opposed to being, oh, well, we didn't do it. Okay, we should do it next time.

AI assessment note: “Why weren't we multi-threaded in this account?”

Q How do we test that in the interview?

A So I asked for real examples. So if you're a leader, I'll give me, I'll give you an example. So if you're a leader, I'll always ask, I'd like to know, like, give me an example, right? Give me an example of someone whose career you impacted personally, right? And, and you kind of like hear it, and usually everybody has one or two examples, or they're able to, like, Manufacture something. Okay, that seems okay. But again, this is one where, again, you can tell by the passion, right? Someone talking about, oh, my God, Harry. Harry was a disaster when I met him, but, you know, like, he has so much potential. We worked on it, right? Or someone, someone would just like talk more factually. So that's already one, one read. And then I asked another one, which is. And this is the key one, which is, hey, what is, um, uh, uh, and I, I learned this from probably the best interviewer I know, which is this guy called Tony Huey when we were working at Dropbox together. And it was, hey, tell me about someone who you were not able to get, to get them to reach their fullest potential. And again, it's about how they answer for me, right? In terms of reading it, uh, and the people you want are people who take it personally. It's like, it's a personal failure of mine that Harry, I wasn't get, I wasn't able to get Harry to reach so much potential. I saw so much potential, but I wasn't able to get th…

AI assessment note: “give me an example of someone whose career you impacted personally”