The Exchanges

Q When we sit down and we do postmortems and we do like collaborative forecasting on what we've done and what we've got ahead of us, how often do we do that?

A Uh, every, every week on Thursdays, every one of my frontline managers goes and does a forecast call with their team, and they either do it as a team, they do it individually. I actually don't care how it gets done, but I do care that you're sitting down with your rep and saying, okay, walk me through what's the pain we're solving, right? And then it's like, okay, what metric is attached to that pain? And then who gives a shit about that metric? Are we talking to them, Right? Like these types of questions that help us understand, do you have control of the deal? Is the deal in the right stage? Right? Are we, are we making assumptions? Do we need to go back and actually you get to the end and something happens and you're like, I have a bad champion. Well, actually you're back here and you skipped a couple steps, right? Let's just be real and move it back there now and go do the work to actually build the right deal. So we do that once a week. I do that with my frontline leaders on Fridays. And the way that I do it is I just model the behavior that I want them to be doing in their forecast calls, and I expect that they're in the deals in the same way that, like, I'm running a couple deals with reps, and it's a lot of fun.

AI assessment note: “every week on Thursdays, every one of my frontline managers goes and does a forecast”

Q When we sit down and we do postmortems and we do like collaborative forecasting on what we've done and what we've got ahead of us, how often do we do that?

A Uh, every, every week on Thursdays, every one of my frontline managers goes and does a forecast call with their team, and they either do it as a team, they do it individually. I actually don't care how it gets done, but I do care that you're sitting down with your rep and saying, okay, walk me through what's the pain we're solving, right? And then it's like, okay, what metric is attached to that pain? And then who gives a shit about that metric? Are we talking to them, Right? Like these types of questions that help us understand, do you have control of the deal? Is the deal in the right stage? Right? Are we, are we making assumptions? Do we need to go back and actually you get to the end and something happens and you're like, I have a bad champion. Well, actually you're back here and you skipped a couple steps, right? Let's just be real and move it back there now and go do the work to actually build the right deal. So we do that once a week. I do that with my frontline leaders on Fridays. And the way that I do it is I just model the behavior that I want them to be doing in their forecast calls, and I expect that they're in the deals in the same way that, like, I'm running a couple deals with reps, and it's a lot of fun.

AI assessment note: “every week on Thursdays, every one of my frontline managers goes and does a forecast call”

Q You said AI doesn't change SDRs. It doesn't change Outbound. What does it change?

A Well, I wouldn't say that it doesn't, I, I didn't say it doesn't change it. I just said it doesn't replace it, right? I think about this, like, if I can, and, and this is like my thesis with the ClayDR team is like, let's say, uh, let's say, uh, uh, let's say, uh, uh, let's say, uh, uh, uh, an SDR can book, I don't know, in a, in a given month, say they're booking 15 meetings, right? say, uh, say, uh, If I can arm that rep with Clay And a, you know, a clod seat, maybe a lovable seat, I don't know. I can tool them with some sort of AI stack, right? And now they can book 40 meetings a month. I'm going to say, yes, please, thank you, okay? Now I want to grow my team of SDRs from eight to fucking infinity, right? Because I see a ton more productivity. Anybody that's like, oh, well, you know, we're just going to cut our SDR team in half, I'm like, hmm, okay. That's an interesting move, right? That's a, that's a scared play that you're making because you're saying I can get the same productivity for half versus saying I can get this productivity and now I'm going to go multiply that into infinity and take all the space, all the oxygen out of these accounts.

AI assessment note: “I didn't say it doesn't change it. I just said it doesn't replace it”

Q And inferences their kind of sales and marketing costs in some ways. How does your job change when kind of people have tried the product already, uh, they've got usage already, and it's not the SDR outbound that it used to be?

A Well, I think, I think if you, you're talking about like a PLG motion, right? Um, and if you have usage, your, your job then becomes, what are the next use cases? What are the next teams? You're fighting over like workloads, right? Rather than going and landing a logo. Because if you think about, think about, um, I don't know, think about Salesforce, right? How many places, how many entrances are there for different AI tools, right? And then how much market share internally at Salesforce Do they have? So like, if you go land a logo, let's say Salesforce is on, is on a PLG motion for your company, your AI widget, right? And then, you know, you got like, I don't know, three people in the marketing team using it, three people in the sales team, whatever, right? Your job then as the rep becomes, how do I go take that market share in that company faster than any other AI company or any of our competitors can come in and take some of that? Because once they're in, then you're fighting with them over workloads versus fighting with inertia. So it's almost like, can you go into an account and suck the oxygen out, right? And that's actually how I think PLG businesses do really, really well, right? Someone comes in, they, you know, they're dabbling in the product, right? And you as a seller, you're like, I'm going to go market that internally at that account to all of the other people and…

AI assessment note: “your job then becomes, what are the next use cases? What are the next teams?”

Q So this is feedback in the job interview?

A Yeah, I'll say, like, I'll give an example. I hired, I hired a guy in San Francisco who I'm really excited about. He went on a walk with Varun, Bruin called me after, gave me a voice note, and gave me, gave me, like, some feedback. So I just called him, and I was like, hey, how do you think it went? Like, you know, okay, great, great, great. Hey, this is something that, like, this is something that I got. Like, this was part of the feedback that I got. What do you think about that? And you just listen, and it tells you everything that you need to know about what it's going to be like to work with that person, right? If they're like, oh, well, like, oh, I mean, he didn't really say that. Oh, interesting. Okay, but if they're like, ah, Okay, yeah, that's fair. How do I go, how do I go and overcome that? And they're like, yo, what do I do? That's actually very interesting, especially in a company like Clay, where we're like, I don't know, building something new. There's a lot of like open white space, right? If someone's really defensive, that's actually the biggest red flag. And I, we need to incorporate it into the, into the rep interview. Um, but like that's, I, I made a hire one time and, and Ever since I've kind of just said, okay, I'm going to give you the feedback and let's see how you react. And actually it's even better if the recruiter gives them the feedback. It's sort …

AI assessment note: “Yeah, I'll say, like, I'll give an example.”

Q And inferences their kind of sales and marketing costs in some ways. How does your job change when kind of people have tried the product already, uh, they've got usage already, and it's not the SDR outbound that it used to be?

A Well, I think, I think if you, you're talking about like a PLG motion, right? Um, and if you have usage, your, your job then becomes, what are the next use cases? What are the next teams? You're fighting over like workloads, right? Rather than going and landing a logo. Because if you think about, think about, um, I don't know, think about Salesforce, right? How many places, how many entrances are there for different AI tools, right? And then how much market share internally at Salesforce Do they have? So like, if you go land a logo, let's say Salesforce is on, is on a PLG motion for your company, your AI widget, right? And then, you know, you got like, I don't know, three people in the marketing team using it, three people in the sales team, whatever, right? Your job then as the rep becomes, how do I go take that market share in that company faster than any other AI company or any of our competitors can come in and take some of that? Because once they're in, then you're fighting with them over workloads versus fighting with inertia. So it's almost like, can you go into an account and suck the oxygen out, right? And that's actually how I think PLG businesses do really, really well, right? Someone comes in, they, you know, they're dabbling in the product, right? And you as a seller, you're like, I'm going to go market that internally at that account to all of the other people and…

AI assessment note: “your job then becomes, what are the next use cases? What are the next teams?”

Q Like, fuck, I don't need them. I'm doing, I'm doing more, I'm doing better with less. How does the world change with AISDRs? Are SDRs dead? Is outbound dead?

A Absolutely not. No way. So, so it's funny, people, people ask this question, uh, when I first started Clay, they were like, oh, SDRs, what's your perspective? And I was like, I'm building an SDR team. I'm building a ClayDR team, right? Because outbound will never be dead. You can't reach every single company and every single buyer with whatever marketing you're doing. Or if you do, it's less efficient, right? It might be efficient when you're, you know, when you're trying to generate forty million dollars a pipeline, Because you have a, I don't know, 10 or fifteen million dollar revenue target, but like when you get into having to build, you know, a quarter billion dollars of pipeline, like it's actually probably a little bit more efficient to just put some, you know, hungry, scrappy, 24 year old on the field, pay them, you know, a certain amount of money, and say, go run at these accounts, right? That's the first thing. The second thing is like, Hey, you don't have an SDR team. Who the hell are you going to promote into your, into your closing roles? It's really, it's, it's, it's completely de-risked if you have an SDR that you're promoting. Those are the best people.

AI assessment note: “Absolutely not. No way. [...] outbound will never be dead.”

Q What's your favorite win story of a deal?

A I worked on a deal with a rep at my last company, uh, it's a large bank in Australia, it's one of the big four banks, and they, one, we, we, we had a, we had an EB, she was the chief digital officer, chief data officer, um, and she just fucking got it, man, like, she was, she was, um, uh, maybe a little bit earlier in, in career for, for, like, a, a C-level role, um, Um, she was super innovative. She would come to us and she'd be like, yo, I'm checking out these other tools. What do you guys think? How did they play? Like, does this story make sense? So like, it was almost like working with a friend that was like really smart, that was putting together their data stack. The use case was the coolest though, which is they were using our product, uh, to basically create new derivatives, uh, that they were going to sell to my, my, my, my, my, my classification, um, poor rich people. People who had between ten million dollars and fifty million dollars of net worth, and they were gonna launch 10 of these products, and they were expecting each of those products to generate a hundred million dollars for them. And I was like, wow, like, you've critic, like, you've thought about, like, we kind of uncovered all that and helped them build the business case, but like, it was something that was like a very intricate use case that had a huge financial impact, and it was just, it was a fun tea…

AI assessment note: “I worked on a deal with a rep at my last company, uh, it's a large bank”

Q So how should early stage founders train reps?

A So here's, here's what we did at Heap. Um, basically Mateen and Ravi, it's like they showed, they did the thing, we rode along, and then that shift started to kind of like happen of like, okay, now we run the call and maybe you're on a few. Now you have gongs, so you can actually send the people that you hired all of your gong calls before. Like that's all the founders that I work with. I tell them like, You know, do you have Gong? And if they don't, I'm like, ooh, red flag, you gotta go, just go get, just buy it, right? Um, and then send whoever you hire all of the calls that you've done, because they're gonna, one, they're gonna give you feedback on like how to sell, but two, they'll hear how you talk about it, and that's actually the most, like, that's the most important thing to me, is like, how do I take what's in my brain and put it in your brain, right?

AI assessment note: “send whoever you hire all of the calls that you've done”

Q What's your favorite win story of a deal?

A I worked on a deal with a rep at my last company, uh, it's a large bank in Australia, it's one of the big four banks, and they, one, we, we, we had a, we had an EB, she was the chief digital officer, chief data officer, um, and she just fucking got it, man, like, she was, she was, um, uh, maybe a little bit earlier in, in career for, for, like, a, a C-level role, um, Um, she was super innovative. She would come to us and she'd be like, yo, I'm checking out these other tools. What do you guys think? How did they play? Like, does this story make sense? So like, it was almost like working with a friend that was like really smart, that was putting together their data stack. The use case was the coolest though, which is they were using our product, uh, to basically create new derivatives, uh, that they were going to sell to my, my, my, my, my, my classification, um, poor rich people. People who had between ten million dollars and fifty million dollars of net worth, and they were gonna launch 10 of these products, and they were expecting each of those products to generate a hundred million dollars for them. And I was like, wow, like, you've critic, like, you've thought about, like, we kind of uncovered all that and helped them build the business case, but like, it was something that was like a very intricate use case that had a huge financial impact, and it was just, it was a fun tea…

AI assessment note: “I worked on a deal with a rep at my last company”

Q So if I'm a founder hiring today, early stage company, under ten million in revenue, What should I look for in the people that I'm hiring? Just people that press send and have a lot of energy. And remember this really early stage, what is that profile?

A I keep coming back to like thinking critically about your customers. So like I'll give an example, maybe you're selling an AI widget, right? Does this person come in and talk about the widget or do they talk about how, I don't know, uh, JPMC would use it or the company that they're currently at, how they would use it and the impact that it has And like, what I, what I mean by impact is like, I give an example. Whenever we talk about AI tools, I feel like we talk about like the art of possible, like pie in the sky stuff. And I'm like, hey, hey, hey, we're, we're bringing it back here, right? Why don't you give me an AI tool that automatically tells my reps when they have a close date in the past, the basic shit when we're single threaded, let's start there. Let's help people do the basics. Well, before we get to like, oh, it, it automates, it automates the outbound and then it automates the first deck. And then, you know, it automates the rest of the sales process. I'm like, Okay. Great. Great. Great. We can get there. Let's start with the basics. So like do when they talk about your widget in the context of their company, are they talking about pie in the sky or are they like, this is actually the real problem that it's solving for us. And the impact of that real problem is that, I don't know, our forecast is, is, is screwed up or we miss our revenue target or like our rep prod…

AI assessment note: “Can they tie your thing To a real business problem that they are facing”

Q So how should early stage founders train reps?

A So here's, here's what we did at Heap. Um, basically Mateen and Ravi, it's like they showed, they did the thing, we rode along, and then that shift started to kind of like happen of like, okay, now we run the call and maybe you're on a few. Now you have gongs, so you can actually send the people that you hired all of your gong calls before. Like that's all the founders that I work with. I tell them like, You know, do you have Gong? And if they don't, I'm like, ooh, red flag, you gotta go, just go get, just buy it, right? Um, and then send whoever you hire all of the calls that you've done, because they're gonna, one, they're gonna give you feedback on like how to sell, but two, they'll hear how you talk about it, and that's actually the most, like, that's the most important thing to me, is like, how do I take what's in my brain and put it in your brain, right?

AI assessment note: “send whoever you hire all of the calls that you've done”

Q Like, fuck, I don't need them. I'm doing, I'm doing more, I'm doing better with less. How does the world change with AISDRs? Are SDRs dead? Is outbound dead?

A Absolutely not. No way. So, so it's funny, people, people ask this question, uh, when I first started Clay, they were like, oh, SDRs, what's your perspective? And I was like, I'm building an SDR team. I'm building a ClayDR team, right? Because outbound will never be dead. You can't reach every single company and every single buyer with whatever marketing you're doing. Or if you do, it's less efficient, right? It might be efficient when you're, you know, when you're trying to generate forty million dollars a pipeline, Because you have a, I don't know, 10 or fifteen million dollar revenue target, but like when you get into having to build, you know, a quarter billion dollars of pipeline, like it's actually probably a little bit more efficient to just put some, you know, hungry, scrappy, 24 year old on the field, pay them, you know, a certain amount of money, and say, go run at these accounts, right? That's the first thing. The second thing is like, Hey, you don't have an SDR team. Who the hell are you going to promote into your, into your closing roles? It's really, it's, it's, it's completely de-risked if you have an SDR that you're promoting. Those are the best people.

AI assessment note: “outbound will never be dead. You can't reach every single company”

Q Okay, so what's the worst hiring mistake sales leaders make?

A Uh, focusing on the last company that they were at and if it was a playbook company or not. So like, I'll give an example. It's actually interesting. You see, um, I don't know if you, if you saw, uh, Brian McCarthy just joined Cursor from Rubric, right? Um, and, and actually, you know, I, I was texting with a friend last night. Uh, a lot of people are now moving from Rubric to Cursor. Rubric, very playbook company. Cursor, AI first company. And I, I have a ton of respect for those guys and all, all the playbook folks. And like, I think what they've done and what they've taught the, the, You know, craft of sales is, is really, really valuable. It's going to be very interesting to see how they modify their playbook to be AI first, because I think there's a lot of parts that are still very relevant, right? But I think there's some parts that are going to be thrown out, right? Like, uh, I give an example, like, uh, understanding entire business case before you do anything in the product or you show any value, like you can't really sell that way in the AI space. So like, I'm very interested to see how that works. But like I've worked for leaders in the past that, that they, they have a certain hiring profile and they do not want to deviate from that even for high slope individuals. I think that that's, that's a mistake because then you just get the same, you get a hundred of the sam…

AI assessment note: “focusing on the last company that they were at and if it was a playbook”

Q What are the biggest mistakes sales leaders make in forecasting?

A I think at the front line, not being in the details, not being in the deals with the rep. So like, uh, I'll give an example. I talked about John Dalton earlier. John Dalton is like one of my favorite people. I, I would love to work with John Dalton for the rest of my life. Um, he also lives in Santa Barbara. He's very chill. John Dalton, if you asked him, hey, what's going on with the company? He knows because he's in the deal with the rep doing the work, showing the rep, here's how you do a good deal. Like, let me teach you how to run these types of deals. He's in the deal. So he doesn't need to look at his notes. He's like, yeah, this happened. This is the immediate next step that we're doing to get to the EB or to, you know, we have a call on Friday to talk about all the approval processes and the signing process versus, you know, you might ask, uh, you might ask Stacy, right? Hey, what's, hey, what's going on with company? And she's like, ah, let me check, let me check my notes. Ah, the last update. And I'm like, I can read the update in Salesforce. Right? This, the, the, the rep has specific, we have a specific, like, standardized way of writing your next steps. I can go read that too. But what are, what is your perspective on the deal? Are you in the deal? And like, not every frontline manager can be in every single deal, so you have to choose which ones are the most impo…

AI assessment note: “not being in the details, not being in the deals with the rep”

Q So this is feedback in the job interview?

A Yeah, I'll say, like, I'll give an example. I hired, I hired a guy in San Francisco who I'm really excited about. He went on a walk with Varun, Bruin called me after, gave me a voice note, and gave me, gave me, like, some feedback. So I just called him, and I was like, hey, how do you think it went? Like, you know, okay, great, great, great. Hey, this is something that, like, this is something that I got. Like, this was part of the feedback that I got. What do you think about that? And you just listen, and it tells you everything that you need to know about what it's going to be like to work with that person, right? If they're like, oh, well, like, oh, I mean, he didn't really say that. Oh, interesting. Okay, but if they're like, ah, Okay, yeah, that's fair. How do I go, how do I go and overcome that? And they're like, yo, what do I do? That's actually very interesting, especially in a company like Clay, where we're like, I don't know, building something new. There's a lot of like open white space, right? If someone's really defensive, that's actually the biggest red flag. And I, we need to incorporate it into the, into the rep interview. Um, but like that's, I, I made a hire one time and, and Ever since I've kind of just said, okay, I'm going to give you the feedback and let's see how you react. And actually it's even better if the recruiter gives them the feedback. It's sort …

AI assessment note: “I'm going to give you the feedback and let's see how you react.”

Q Okay, so what's the worst hiring mistake sales leaders make?

A Uh, focusing on the last company that they were at and if it was a playbook company or not. So like, I'll give an example. It's actually interesting. You see, um, I don't know if you, if you saw, uh, Brian McCarthy just joined Cursor from Rubric, right? Um, and, and actually, you know, I, I was texting with a friend last night. Uh, a lot of people are now moving from Rubric to Cursor. Rubric, very playbook company. Cursor, AI first company. And I, I have a ton of respect for those guys and all, all the playbook folks. And like, I think what they've done and what they've taught the, the, You know, craft of sales is, is really, really valuable. It's going to be very interesting to see how they modify their playbook to be AI first, because I think there's a lot of parts that are still very relevant, right? But I think there's some parts that are going to be thrown out, right? Like, uh, I give an example, like, uh, understanding entire business case before you do anything in the product or you show any value, like you can't really sell that way in the AI space. So like, I'm very interested to see how that works. But like I've worked for leaders in the past that, that they, they have a certain hiring profile and they do not want to deviate from that even for high slope individuals. I think that that's, that's a mistake because then you just get the same, you get a hundred of the sam…

AI assessment note: “focusing on the last company that they were at and if it was a playbook company”

Q So yes, a hundred percent. You said about, really interesting, everyone at Clay is a social media star. Do you encourage your reps to be public online? We had the head of growth at Lovable on, and she's like, the best form of marketing Is employee-led marketing?

A Yeah, yeah. I, I think, uh, we, uh, I, I tell people, I need to be better at this, like, I need to follow my own advice, like, we do really cool shit at Clay, so like, I'll give an example, um, you can, if you work at Clay, and you want to try out a new AI tool, you can just go into a channel and say, can I have a ramp card to try this tool out? And they'll give you a ramp card. Like, no questions asked. They're like, I want to try this AI widget, can I do it? And they're like, Yeah, get after it. Right? Versus like a lot of other companies are like, ooh, that needs to go through our, oh, it needs to go through our AI council, and they need to evaluate it, and we'll get back to you never, how's that, right? And so, like, things like that, I'm like, whoa, hey, you should actually post about that, because one, that's something that no other company is doing, and anybody who's out there and sees that and is currently rotting at their company, they're like, holy shit, I want to do that, right? Um, we do a lot of, you know, we talked a lot about, like, the cultural things that we do that are That are fun, right? I think that it should have some sort of learning or training. Hey, I'm getting better at my job, right? Like, I think, I think that's a great way. Like, that's kind of modern marketing.

AI assessment note: “you should actually post about that, because one, that's something that no other company”

Q So if I'm a founder hiring today, early stage company, under ten million in revenue, What should I look for in the people that I'm hiring? Just people that press send and have a lot of energy. And remember this really early stage, what is that profile?

A I keep coming back to like thinking critically about your customers. So like I'll give an example, maybe you're selling an AI widget, right? Does this person come in and talk about the widget or do they talk about how, I don't know, uh, JPMC would use it or the company that they're currently at, how they would use it and the impact that it has And like, what I, what I mean by impact is like, I give an example. Whenever we talk about AI tools, I feel like we talk about like the art of possible, like pie in the sky stuff. And I'm like, hey, hey, hey, we're, we're bringing it back here, right? Why don't you give me an AI tool that automatically tells my reps when they have a close date in the past, the basic shit when we're single threaded, let's start there. Let's help people do the basics. Well, before we get to like, oh, it, it automates, it automates the outbound and then it automates the first deck. And then, you know, it automates the rest of the sales process. I'm like, Okay. Great. Great. Great. We can get there. Let's start with the basics. So like do when they talk about your widget in the context of their company, are they talking about pie in the sky or are they like, this is actually the real problem that it's solving for us. And the impact of that real problem is that, I don't know, our forecast is, is, is screwed up or we miss our revenue target or like our rep prod…

AI assessment note: “Can they tie your, your thing To a real business problem that they are facing”

Q What are the biggest mistakes sales leaders make in forecasting?

A I think at the front line, not being in the details, not being in the deals with the rep. So like, uh, I'll give an example. I talked about John Dalton earlier. John Dalton is like one of my favorite people. I, I would love to work with John Dalton for the rest of my life. Um, he also lives in Santa Barbara. He's very chill. John Dalton, if you asked him, hey, what's going on with the company? He knows because he's in the deal with the rep doing the work, showing the rep, here's how you do a good deal. Like, let me teach you how to run these types of deals. He's in the deal. So he doesn't need to look at his notes. He's like, yeah, this happened. This is the immediate next step that we're doing to get to the EB or to, you know, we have a call on Friday to talk about all the approval processes and the signing process versus, you know, you might ask, uh, you might ask Stacy, right? Hey, what's, hey, what's going on with company? And she's like, ah, let me check, let me check my notes. Ah, the last update. And I'm like, I can read the update in Salesforce. Right? This, the, the, the rep has specific, we have a specific, like, standardized way of writing your next steps. I can go read that too. But what are, what is your perspective on the deal? Are you in the deal? And like, not every frontline manager can be in every single deal, so you have to choose which ones are the most impo…

AI assessment note: “I think at the front line, not being in the details, not being in the deals”

Q So yes, a hundred percent. You said about, really interesting, everyone at Clay is a social media star. Do you encourage your reps to be public online? We had the head of growth at Lovable on, and she's like, the best form of marketing Is employee-led marketing?

A Yeah, yeah. I, I think, uh, we, uh, I, I tell people, I need to be better at this, like, I need to follow my own advice, like, we do really cool shit at Clay, so like, I'll give an example, um, you can, if you work at Clay, and you want to try out a new AI tool, you can just go into a channel and say, can I have a ramp card to try this tool out? And they'll give you a ramp card. Like, no questions asked. They're like, I want to try this AI widget, can I do it? And they're like, Yeah, get after it. Right? Versus like a lot of other companies are like, ooh, that needs to go through our, oh, it needs to go through our AI council, and they need to evaluate it, and we'll get back to you never, how's that, right? And so, like, things like that, I'm like, whoa, hey, you should actually post about that, because one, that's something that no other company is doing, and anybody who's out there and sees that and is currently rotting at their company, they're like, holy shit, I want to do that, right? Um, we do a lot of, you know, we talked a lot about, like, the cultural things that we do that are That are fun, right? I think that it should have some sort of learning or training. Hey, I'm getting better at my job, right? Like, I think, I think that's a great way. Like, that's kind of modern marketing.

AI assessment note: “I'm like, whoa, hey, you should actually post about that”

Q You said AI doesn't change SDRs. It doesn't change Outbound. What does it change?

A Well, I wouldn't say that it doesn't, I, I didn't say it doesn't change it. I just said it doesn't replace it, right? I think about this, like, if I can, and, and this is like my thesis with the ClayDR team is like, let's say, uh, let's say, uh, uh, let's say, uh, uh, let's say, uh, uh, uh, an SDR can book, I don't know, in a, in a given month, say they're booking 15 meetings, right? say, uh, say, uh, If I can arm that rep with Clay And a, you know, a clod seat, maybe a lovable seat, I don't know. I can tool them with some sort of AI stack, right? And now they can book 40 meetings a month. I'm going to say, yes, please, thank you, okay? Now I want to grow my team of SDRs from eight to fucking infinity, right? Because I see a ton more productivity. Anybody that's like, oh, well, you know, we're just going to cut our SDR team in half, I'm like, hmm, okay. That's an interesting move, right? That's a, that's a scared play that you're making because you're saying I can get the same productivity for half versus saying I can get this productivity and now I'm going to go multiply that into infinity and take all the space, all the oxygen out of these accounts.

AI assessment note: “I didn't say it doesn't change it. I just said it doesn't replace it”

Q How do you know when you are setting the wrong goals versus have a shit team? Because two different people could go, ah, we've got two high expectations, or it could be you're just ownership people.

A Yeah, I, and, and usually, uh, you can tell by the reaction, right? Uh, so actually, coming back to Heap, they hired both Todd and I at roughly the same time, I think Todd was like three, maybe three, four months before me, and they told us like a year later, they were like, we hired you two at a time. I tell every founder this, I'm like, hire two at a time, because then you'll actually see Is one, you hire one, you're like, is it good? Is it not good? I don't know. If you hire two, it's pretty clear whether one's good and one's bad. They told us like a year later, they were like, yeah, we hired both of you, and we were like, we're probably gonna have to fire one and keep the better one, but you both were really good, so we kept you both, and I was like, oh, ok, well thanks, but like, that's, that's how you do it, right? You have, let's say you have a hundred reps, there's gonna be five that just bitch about quota and blah blah blah, but if you, if you dig under the covers, they're probably not doing the work to go and be successful. Right? And those are the people that you probably don't want on the team.

AI assessment note: “hire two at a time, because then you'll actually see”

Q Why did it at Heap and not at Clay?

A Uh, I mean, we did it at Heap because we were the first two reps, and they were like, just go fucking close as much. I think it, I think it depends on the economics of your business. So like if you think about clay, right? Like we pay for the data that we sell, right? So like we pay per credit in the same way that like we charge for a credit of, of data. Um, and, and actually our, our, our economics are very, very good. Our, our head of finance is really smart about, about all that type of stuff. But like in some businesses you have shit margins and I've worked for companies that have, you know, less, less than ideal margins. And it kind of puts, it kind of compresses what you can actually pay. So like maybe that's something that you look for in the AI era, right? Is, is good margins. I don't actually know why, why we can't do that. Like there's, there's, there's a flat, there's some sort of flat pay that you have a base commission rate. And then on top of that, you get accelerators, right? All that Heap did was just jump straight to the accelerators and say, you have an artificially low base, right? Now go, now go work your ass off.

AI assessment note: “we did it at Heap because we were the first two reps”

Q leaders and salespeople are looking at themselves, saying, am I in the right place? You're in a SaaS company, and you're like, well, it's not an AI company, and you're seeing a load of friends make a lot of money at AI companies. How should people actually think about the decision of, should I leave my SaaS company and join a hot AI company? Or should I actually just stay?

A So I have a lot of these types of conversations, both with like peers and, and with, uh, folks that are having this like kind of evaluation. And I think there's, there's two ways to approach it, right? A lot of folks that I talk to are at software companies. They've been there for like four years, five years. The learning curve is kind of flattened out. And like the, the phrase that I use to describe how they might feel is like, Hey, do you feel like you're kind of like rotting? Right? Like you're, you're not, you're not learning a ton more. The, the, the learning curve is flattened for you. You're not in an AI space, which like, I think is like the next, uh, the next phase of things to learn. And actually almost every time they're like, yeah, that's exactly how I feel. And I'm like, okay, let's, let's fix that then. Because that once you stop learning, like you actually, as, as a person, I think start to settle And then it's just a, um, like a process of settling all the way down to the bottom.

AI assessment note: “do you feel like you're kind of like rotting?”

Q And they will have shiny VCs, and they will have people who are pronouncing themselves to be replacing work for every large profession. What would you advise those sales reps who feel like they've plateaued, rotting, as you put it nicely, um, which one should I choose?

A Honestly, it's, it's really tough, and, like, I obviously, like, uh, I, I hadn't intended to leave DBT, if I'm, if I'm honest, like, I was like, I'm gonna finish out the fiscal year, and then maybe I'll start to think about what's next, um, and I, I met Varun, and you know Varun. We went for multiple walks around, he lives around the corner from me in Brooklyn, and so I, I, I feel like I got a little bit of the cheat code, because I, I do think that Clay is, like, the most compelling company on the planet right now, and, like, when you think about AI companies. A lot of people have, we just hired a RevOps guy. He's fantastic. He has this phrase. He's like, everybody has the Claude spookies. And I'm like, that's a really good way to describe it. The feeling of like, well, why wouldn't Claude just do this? Is Claude going to overtake this market? Is Claude going to put you out of business? Right? And it's like, there it's, there's a lot of companies out there that I look at and I'm like, I got the, I, yeah, I think that that could be a thing for you. And so like, The real answer is I don't, I don't really know, but I think about is there something that's not just AI that's defensible, right? Like Clay has this data marketplace. It's really, it's tough to build that. Like you could go, yeah, you could go do that. You could go buy a 180 different data providers and build your own, …

AI assessment note: “I would look for some sort of other defensibility outside of just we're automating this”

Q How do you know when you are setting the wrong goals versus have a shit team? Because two different people could go, ah, we've got two high expectations, or it could be you're just ownership people.

A Yeah, I, and, and usually, uh, you can tell by the reaction, right? Uh, so actually, coming back to Heap, they hired both Todd and I at roughly the same time, I think Todd was like three, maybe three, four months before me, and they told us like a year later, they were like, we hired you two at a time. I tell every founder this, I'm like, hire two at a time, because then you'll actually see Is one, you hire one, you're like, is it good? Is it not good? I don't know. If you hire two, it's pretty clear whether one's good and one's bad. They told us like a year later, they were like, yeah, we hired both of you, and we were like, we're probably gonna have to fire one and keep the better one, but you both were really good, so we kept you both, and I was like, oh, ok, well thanks, but like, that's, that's how you do it, right? You have, let's say you have a hundred reps, there's gonna be five that just bitch about quota and blah blah blah, but if you, if you dig under the covers, they're probably not doing the work to go and be successful. Right? And those are the people that you probably don't want on the team.

AI assessment note: “If you hire two, it's pretty clear whether one's good and one's bad.”

Q Why did it at Heap and not at Clay?

A Uh, I mean, we did it at Heap because we were the first two reps, and they were like, just go fucking close as much. I think it, I think it depends on the economics of your business. So like if you think about clay, right? Like we pay for the data that we sell, right? So like we pay per credit in the same way that like we charge for a credit of, of data. Um, and, and actually our, our, our economics are very, very good. Our, our head of finance is really smart about, about all that type of stuff. But like in some businesses you have shit margins and I've worked for companies that have, you know, less, less than ideal margins. And it kind of puts, it kind of compresses what you can actually pay. So like maybe that's something that you look for in the AI era, right? Is, is good margins. I don't actually know why, why we can't do that. Like there's, there's, there's a flat, there's some sort of flat pay that you have a base commission rate. And then on top of that, you get accelerators, right? All that Heap did was just jump straight to the accelerators and say, you have an artificially low base, right? Now go, now go work your ass off.

AI assessment note: “I don't actually know why, why we can't do that.”

Q And they will have shiny VCs, and they will have people who are pronouncing themselves to be replacing work for every large profession. What would you advise those sales reps who feel like they've plateaued, rotting, as you put it nicely, um, which one should I choose?

A Honestly, it's, it's really tough, and, like, I obviously, like, uh, I, I hadn't intended to leave DBT, if I'm, if I'm honest, like, I was like, I'm gonna finish out the fiscal year, and then maybe I'll start to think about what's next, um, and I, I met Varun, and you know Varun. We went for multiple walks around, he lives around the corner from me in Brooklyn, and so I, I, I feel like I got a little bit of the cheat code, because I, I do think that Clay is, like, the most compelling company on the planet right now, and, like, when you think about AI companies. A lot of people have, we just hired a RevOps guy. He's fantastic. He has this phrase. He's like, everybody has the Claude spookies. And I'm like, that's a really good way to describe it. The feeling of like, well, why wouldn't Claude just do this? Is Claude going to overtake this market? Is Claude going to put you out of business? Right? And it's like, there it's, there's a lot of companies out there that I look at and I'm like, I got the, I, yeah, I think that that could be a thing for you. And so like, The real answer is I don't, I don't really know, but I think about is there something that's not just AI that's defensible, right? Like Clay has this data marketplace. It's really, it's tough to build that. Like you could go, yeah, you could go do that. You could go buy a 180 different data providers and build your own, …

AI assessment note: “I would look for some sort of other defensibility outside of just we're automating this.”