The Exchanges

Q Okay, so we have head of revenue. That's one nomenclature relatively solved in a very unclear way. Thanks for that, Jordan. Um, but my next one is sales playbook. Love the word sales playbook. How do you define what actually is a sales playbook, Jordan?

A So sales playbook is, uh, it's like five, it's discrete steps that you take to accomplish five things. Um, one is to help the customer understand what you do. Um, the second is to evaluate whether or not your solution is going to drive, you know, some sort of critical business outcome for that customer. Uh, the third is to gain consensus across who members involved in that decision-making process. The fourth is to agree and formalize their relationship. And most importantly, the fifth one is that sales process and that sales playbook should create a blueprint for a customer to be really successful and for you to make good on those promises that were made in the cycle. So that's all a sales playbook is.

AI assessment note: “sales playbook is, uh, it's like five, it's discrete steps that you take”

Q Uh, final one for you, my friend. What one company sales strategy have you been most impressed by recently?

A Yeah, recently, um, I think about the ones that have, like, really hard problems to solve. Um, you talked to Eleanor, I think Retool's a really interesting one. Like, they're selling all things to all people. They have no, like, clear buyer or person that owns that problem. Yet they still like grow incredibly fast. And I think that they, um, they've created like a very nuanced, um, product led, but also sales assisted growth model, which I think is, is really interesting. Um, I think the second one that impresses me, so that's like in the startup world, um, MongoDB has always impressed me, but it, to go from, um, tops down enterprise led to product led sales, uh, you know, in the last couple of years, that's a really hard transition. I don't think I've ever seen anybody do it and they've done it really well. So I think those two are really great companies to look at.

AI assessment note: “Retool's a really interesting one. Like, they're selling all things to all people.”

Q Well, I mean, I think what problem you're trying to solve might lead into this question, which is like, how do I know whether to get a head of sales, who's probably more experienced, or whether to get young sales reps to really just feed the sales machine? How do I know which one's the right sales hire to make first?

A Yes. So three variables to that. I'm not going to give you any like black and white answers. I'm sorry. That's like the, one of my worst personal qualities, Harry. Uh, so there's three variables. One is the complexity of your sale. Two is the degree of confidence you have in your go to market motion. And then third is, uh, you know, the level of involvement that you want. So like, Um, maybe to get to dive a little bit deeper, if you have really transactional deals, your ASPs are, let's say sub-twelve K, for example, a year, um, you know, it's low and it's simple, then you could probably go higher. Uh, it's based on how many reps can actually handle the, the transactions. If you only have enough transactions to support one rep, then you just hire a junior rep. If you feel like you have enough where like three or four reps can go get transactions, um, then you hire a head of sales, right?

AI assessment note: “If you only have enough transactions to support one rep, then you just hire a junior rep.”

Q Okay, so we have head of revenue. That's one nomenclature relatively solved in a very unclear way. Thanks for that, Jordan. Um, but my next one is sales playbook. Love the word sales playbook. How do you define what actually is a sales playbook, Jordan?

A So sales playbook is, uh, it's like five, it's discrete steps that you take to accomplish five things. Um, one is to help the customer understand what you do. Um, the second is to evaluate whether or not your solution is going to drive, you know, some sort of critical business outcome for that customer. Uh, the third is to gain consensus across who members involved in that decision-making process. The fourth is to agree and formalize their relationship. And most importantly, the fifth one is that sales process and that sales playbook should create a blueprint for a customer to be really successful and for you to make good on those promises that were made in the cycle. So that's all a sales playbook is.

AI assessment note: “sales playbook is, uh, it's like five, it's discrete steps that you take”

Q Respectfully, your title is like revenue leader. Um, what does that mean? How is it different from head of sales or I was looking at it and I was like, uh, What does that mean? No offense.

A Yeah, I don't, I don't know what it means either. I'm with you. Um, it's not different than a CRO. Um, so my remit is, you know, sales development, uh, sales, CS, partnership, customer success, partnerships, uh, you know, a bunch of, uh, broad functions. And, uh, but one funny thing about Monte Carlo is we, we managed to get to like a billion plus valuation. We managed to get to an 80 person go to market team, and we still hadn't hired a recruiter or a head of HR. And so we don't have any formal titling or levels at Monte Carlo. And I think, um, you know, to your question, uh, what we don't know yet about what, what, what to call me is, uh, whether it's CRO or COO. And I think that there's, um, you know, a question in terms of, of remit and like how we want to, uh, our sales team to be oriented. Um, but you know, it just hasn't been a really core focus to figure out what to call me. And so, uh, so head of revenue is fine for now.

AI assessment note: “it's not different than a CRO. Um, so my remit is”

Q Segment and Dropbox, two phenomenal institutions. If you were to take away one or two things that really shaped how you think from each, what would they be, Jordan?

A Yeah, the first one is, um, from Dropbox. I think startups live and die by simplicity and clarity of thought. And so Dropbox is an amazing company with an amazing outcome, and it built one of the best teams I've ever been a part of. But I would say that Dropbox did struggle at times with a core identity of whether it was a consumer company or whether it was an enterprise sales company. And so I think that we spent a lot of cycles and we missed a lot of opportunities because we didn't have that clarity Uh, of conviction and segment was really different. I think, um, that was a career changing experience for me as well. And at the risk of sounding trite, I think I learned in that role, the importance of becoming really great at hiring. So I worked for Genia and I hired a hundred people plus just reporting to Genia. And he actually interviewed every single person and just like rode me so hard, um, on keeping the talent bar super high. And what you realize is you realize that a company is, Really just a combination of people, um, and the way you do things. And so it's your culture and it's the people that you have. And it's very simple. And as a leader, um, you're not gonna have every single skill set. You're not gonna be great at everything. You just can't. And so you get to a point where your only leverage is the people that you're able to, to bring in. So how you evaluate talent…

AI assessment note: “from Dropbox. I think startups live and die by simplicity and clarity of thought.”

Q Respectfully, your title is like revenue leader. Um, what does that mean? How is it different from head of sales or I was looking at it and I was like, uh, What does that mean? No offense.

A Yeah, I don't, I don't know what it means either. I'm with you. Um, it's not different than a CRO. Um, so my remit is, you know, sales development, uh, sales, CS, partnership, customer success, partnerships, uh, you know, a bunch of, uh, broad functions. And, uh, but one funny thing about Monte Carlo is we, we managed to get to like a billion plus valuation. We managed to get to an 80 person go to market team, and we still hadn't hired a recruiter or a head of HR. And so we don't have any formal titling or levels at Monte Carlo. And I think, um, you know, to your question, uh, what we don't know yet about what, what, what to call me is, uh, whether it's CRO or COO. And I think that there's, um, you know, a question in terms of, of remit and like how we want to, uh, our sales team to be oriented. Um, but you know, it just hasn't been a really core focus to figure out what to call me. And so, uh, so head of revenue is fine for now.

AI assessment note: “it's not different than a CRO. Um, so my remit is”

Q move to Jordan Van Horn, revenue leader at Monte Carlo. Now prior to this role, Jordan spent four years at Segment as VP of Sales, leading a sales team of over 50 account executives. Before Segment, Jordan was at Dropbox for four years, including leading enterprise sales for Dropbox Business. What does an ideal onboarding process look like for you with new sales hires, and how should we stage it?

A I always think that onboarding should reflect the stage and maturity of your company. I didn't create a super structured, rigorous onboarding program when we had five employees. Because it's not like you're gonna be in this thirty-day onboarding season, then you're gonna move out. And like, everything's going to be hunky dory. You're walking into like a disaster and you're going to continue to be in a disaster. So you got to figure it out. Early days, the onboarding was, Hey, here's the information that you need. Go figure it out. I ain't got time. And then I'm going to give you a ton of feedback. I'm going to shout at you. I'm going to put time into you, but there's nothing structured. That works with like your first couple of sales hires. It needs to work with your first couple of sales hires because that's the reality of the company. Later on, as you're trying to go onboard, like what we're in right now, we're trying to onboard and hire People in the borders of magnitude of tens and twenties, you have to get really, really disciplined and structured.

AI assessment note: “onboarding should reflect the stage and maturity of your company.”

Q What are the biggest mistakes that managers make onboarding from your perspective, do you think?

A First one is proximity. They're not close enough to the person's work, and they don't know how to break out whether the person actually has a weakness or they're new. Managers need to get really adept Of what are the signals that someone just doesn't know something because they're new or what is the, Hey, there's like an actual skill gap here. Maybe this person doesn't move fast enough. They struggle to actually like parse out those things. Unfortunately, the best way to solve it is through pattern matching and pattern recognition, but you don't necessarily have a lot of that. What I always say to managers is like pick out one or two people that you think had the best onboarding, get really disciplined about those two or three things that that person needs to have and know that inside and out and watch that person like a hawk and support the heck out of them until they get there. And then you should know within 30 days about whether someone's gonna be a fit or not.

AI assessment note: “First one is proximity. They're not close enough to the person's work”

Q move to Jordan Van Horn, revenue leader at Monte Carlo. Now prior to this role, Jordan spent four years at Segment as VP of Sales, leading a sales team of over 50 account executives. Before Segment, Jordan was at Dropbox for four years, including leading enterprise sales for Dropbox Business. What does an ideal onboarding process look like for you with new sales hires, and how should we stage it?

A I always think that onboarding should reflect the stage and maturity of your company. I didn't create a super structured, rigorous onboarding program when we had five employees. Because it's not like you're gonna be in this thirty-day onboarding season, then you're gonna move out. And like, everything's going to be hunky dory. You're walking into like a disaster and you're going to continue to be in a disaster. So you got to figure it out. Early days, the onboarding was, Hey, here's the information that you need. Go figure it out. I ain't got time. And then I'm going to give you a ton of feedback. I'm going to shout at you. I'm going to put time into you, but there's nothing structured. That works with like your first couple of sales hires. It needs to work with your first couple of sales hires because that's the reality of the company. Later on, as you're trying to go onboard, like what we're in right now, we're trying to onboard and hire People in the borders of magnitude of tens and twenties, you have to get really, really disciplined and structured.

AI assessment note: “I always think that onboarding should reflect the stage and maturity of your company.”

Q What are the biggest mistakes that managers make onboarding from your perspective, do you think?

A First one is proximity. They're not close enough to the person's work, and they don't know how to break out whether the person actually has a weakness or they're new. Managers need to get really adept Of what are the signals that someone just doesn't know something because they're new or what is the, Hey, there's like an actual skill gap here. Maybe this person doesn't move fast enough. They struggle to actually like parse out those things. Unfortunately, the best way to solve it is through pattern matching and pattern recognition, but you don't necessarily have a lot of that. What I always say to managers is like pick out one or two people that you think had the best onboarding, get really disciplined about those two or three things that that person needs to have and know that inside and out and watch that person like a hawk and support the heck out of them until they get there. And then you should know within 30 days about whether someone's gonna be a fit or not.

AI assessment note: “First one is proximity. They're not close enough to the person's work”

Q Can I ask, what are the biggest or most common red flags you see when someone's not working out? What are the reasons it's obvious early?

A Impact. Everyone can make an impact in 30 days. Now impact doesn't mean that I'm closing a six-figure deal with like JPMorgan Chase in my first month, but they're actually having an impact. Impact might look like they're on customer calls and they're having an impact on that customer. Or they're looking at the sales process and they're having an impact on that sales process. Or they're raising the bar on the onboarding process and they're getting there faster than the people before them. If you're not seeing that, but you're seeing maybe people are like, oh, I developed the five X pipeline coverage where all of these like very soft things that TBD about whether they're high impact or not, or I put together like my book strategy. Ain't nobody got time for that. You need to come in and you have an impact immediately. And I think that you can tell pretty quickly whether or not someone's like actually jumping in and going in the right direction. Or they're flailing in the organization.

AI assessment note: “Impact. Everyone can make an impact in 30 days.”

Q Yes. It's what matters. Go long. I spoke to, I spoke to Xenia before this episode, who you obviously worked with at Dropbox, and he's now at Miro, but he asked the question of, what did you learn from your job at the winery?

A Oh yeah. Um, well, it's a really amazing first year out of school job because like, you know, one day you're, you're selling to grocery store managers and the next day, you know, I had this job where I was, um, you know, selling to us senators about the importance of like white farmers are the most like environmentally conscious people on earth. And so you get this like insanely wide ranging, uh, group of people that you sell to. And so, um, you know, you, it, it humbles you a lot and it gives you a perspective on how to connect to people in different, um, Different walks of life and be able to understand what's really important to people. And so, and that skill is something that has served me throughout my career.

AI assessment note: “it gives you a perspective on how to connect to people in different”

Q Segment and Dropbox, two phenomenal institutions. If you were to take away one or two things that really shaped how you think from each, what would they be, Jordan?

A Yeah, the first one is, um, from Dropbox. I think startups live and die by simplicity and clarity of thought. And so Dropbox is an amazing company with an amazing outcome, and it built one of the best teams I've ever been a part of. But I would say that Dropbox did struggle at times with a core identity of whether it was a consumer company or whether it was an enterprise sales company. And so I think that we spent a lot of cycles and we missed a lot of opportunities because we didn't have that clarity Uh, of conviction and segment was really different. I think, um, that was a career changing experience for me as well. And at the risk of sounding trite, I think I learned in that role, the importance of becoming really great at hiring. So I worked for Genia and I hired a hundred people plus just reporting to Genia. And he actually interviewed every single person and just like rode me so hard, um, on keeping the talent bar super high. And what you realize is you realize that a company is, Really just a combination of people, um, and the way you do things. And so it's your culture and it's the people that you have. And it's very simple. And as a leader, um, you're not gonna have every single skill set. You're not gonna be great at everything. You just can't. And so you get to a point where your only leverage is the people that you're able to, to bring in. So how you evaluate talent…

AI assessment note: “from Dropbox. I think startups live and die by simplicity and clarity of thought.”

Q I'm on many boards. I, I seem, obviously I'm invested in, I don't know, AC SaaS companies. The most common thing that I hear from founders and sales leaders is, ah, we didn't hit quota or target because they didn't feel it was urgent and it slipped into next quarter. What do you as a sales leader respond to that? I'm sure you see that a lot as an explanation.

A Well, at the end of our quarter, so I might be trying to make that excuse in a couple of weeks. We'll see how it goes. Um, but, uh, you know, urgency or, um, you know, it just wasn't important to them. All of those are subsets of pain, right? Like if you deeply understand a customer's pain, Then you know why they have to solve it. What happens if they don't solve it and why do they need to solve it right now? And if you can't get to that pain for the person that actually is going to make the decision, if you can't make that pain real for that customer and help them understand the consequences of not doing it, um, yeah, your deal is going to slip every single time.

AI assessment note: “if you can't make that pain real for that customer... your deal is going to slip”

Q It, it totally is. You mentioned the exploding discounting. Um, I, I totally get you not being a great customer experience. How do you advise sales leaders on using discounting? There's different views and takes on it. How do you feel about discounting?

A Um, early days, I don't care at all about what price people pay. ARR doesn't matter at all. There's a hot take from a sales leader, uh, early days. I think the only thing that matters is that you're learning and that you have good customers who are good fits that are going to drive your product forward. So they're either going to like say really good things about you in the market, talk to other customers, uh, or they're going to give you really good feedback and your product's going to be, be better because of it. But man, whether they give you 50 K or a million dollars, that doesn't matter. You know, in the grand scheme of things, if you're going to be a big company, that doesn't really matter. So like the way I think about discounting is, um, To answer your question in the early days is, um, I don't care that much about it. I care about aligning price to value and helping them and communicating upfront that, Hey, we're an early product and like pricing is going to change over time. I just need to make sure that you understand that. And I might put something in the order form to reflect that later on. And at the phase where like Monte Carlo's at, for example, now, Um, let's say you're at a hundred customers, um, pricing discipline becomes so important because customers talk to each other and customers don't want, they don't want to not pay a lot of money. They don't want to n…

AI assessment note: “the way I think about discounting is, um, To answer your question in the early days”

Q Yeah. In the interview process, how do you break it down and say, say you're potentially hiring me. Is it number one interview culture fit? Seeing if Harry's a good human, ambitious fit in that way to dig deep three, me pitched a team. How does it break down on an interview by interview? How many interviews does it take? When do you bring in different people?

A Yeah. Good question. So, um, maybe going back to that framework of, um, of culture fit skills and motivation. Um, so the first, the first interview, the screen is the motivation. Like, do you want to do this? Because this thing is hard. Um, like there's a lot of easy ways to make money. And so that's kind of my, like, I'm going to try to scare you off and see if you want to keep talking to us and if you're still excited. So that's the first thing of like, is there motivation aligned to come to Monte Carlo? Do we make sense for their career as much as they make sense for our career? Cause if you don't have motivation, this job sucks. Like just point blank, right? If you don't want to do it, it's not fun. Um, so I think that's like the first interview. The second interview is, um, is, is there historical track record? Is it a track record of excellence? Now I said attribution is really hard in sales and marketing, but you still aren't probably aren't going to hire someone who is middle of the pack or low performing historically throughout their career.

AI assessment note: “the first interview, the screen is the motivation... The second interview is”

Q Um, you learn from fuck ups. Um, when you review your hiring decisions, what are the biggest mistakes you made hiring?

A Yeah, definitely. Um, so there's probably two or three. Um, the first one is Veering from a higher, like a very structured hiring process and letting bias creep into the process is always number one. And that can happen. Like, um, I'll pick on you. Like a board member says, Hey, I heard this person's like the best person in the company. And I'm like, I'm like a first time head of sales hire and I'm like, okay, well I want my board member to be happy and I want to show that I can go get this person. So I'm going to go just like skip a few steps in the interview process and like try to try to win them.

AI assessment note: “the first one is Veering from a higher, like a very structured hiring process”

Q Um, what are the biggest mistakes that managers make onboarding from your perspective, do you think?

A Uh, well, first one is, uh, first one is proximity. They're not close enough to the person's work and they don't know how to break out whether the person actually has a weakness or they're new. And so managers need to get really adept of what are the signals that someone just doesn't know something because they're new or what is it? What is the, Hey, there's like an actual skill gap here. Maybe this person doesn't move fast enough. Maybe they are shocked by our environment and they don't know what to do with it. They struggle to actually like parse out those things. And so, um, unfortunately the best way to solve it is through pattern matching and pattern recognition, but you know, you don't necessarily have a lot of that. And so what I always say to managers is like pick out one or two people that you think had the best onboarding, get really disciplined about those two or three things that that person needs to have and know that inside and out and watch that person like a hawk and support the heck out of them until they get there. Um, and you should know within 30 days about whether someone's going to be a fit or not.

AI assessment note: “first one is proximity. They're not close enough to the person's work”

Q you. The challenge I have here is, and this is relevant for you with, you know, the go to market with Monte Carlo. When it's enterprise, these are long sales cycles. It takes time to develop the relationships. It's harder to know sales efficiency of new reps. How do you, how do you determine quality when sales efficiency is so difficult to manage with such long enterprise deals taking place?

A It's super fair. First of all, um, I think that like, I think we focus in sales too much on the lagging indicator, uh, is my comment to that. And the lagging indicator is revenue. And of course we're going to focus on revenue. Like at the end of the day, that's, um, why everyone gets hired, fired or promoted. But like a ton of stuff happens up until that revenue point. Um, and the better you can build out your sales process and your gas sales playbook, um, to have discrete measurable events. You can get signal on day one of a sales cycle. That deal may or may, like, 10% likelihood or five percent likelihood that it converts into anything that matters, and maybe it's a year from now, but you can know what, what are they doing with those first interactions, um, whether or not they're actually a fit for the organization or whether they're doing well. And that comes down to how well you have designed and structured the sales process, um, and how discreet and measurable each of those steps are. You want me to give you like a tangible example? Or is that too fluffy?

AI assessment note: “build out your sales process... to have discrete measurable events”

Q Well, I mean, I think what problem you're trying to solve might lead into this question, which is like, how do I know whether to get a head of sales, who's probably more experienced, or whether to get young sales reps to really just feed the sales machine? How do I know which one's the right sales hire to make first?

A Yes. So three variables to that. I'm not going to give you any like black and white answers. I'm sorry. That's like the, one of my worst personal qualities, Harry. Uh, so there's three variables. One is the complexity of your sale. Two is the degree of confidence you have in your go to market motion. And then third is, uh, you know, the level of involvement that you want. So like, Um, maybe to get to dive a little bit deeper, if you have really transactional deals, your ASPs are, let's say sub-twelve K, for example, a year, um, you know, it's low and it's simple, then you could probably go higher. Uh, it's based on how many reps can actually handle the, the transactions. If you only have enough transactions to support one rep, then you just hire a junior rep. If you feel like you have enough where like three or four reps can go get transactions, um, then you hire a head of sales, right?

AI assessment note: “If you only have enough transactions to support one rep, then you just hire a junior”

Q you. The challenge I have here is, and this is relevant for you with, you know, the go to market with Monte Carlo. When it's enterprise, these are long sales cycles. It takes time to develop the relationships. It's harder to know sales efficiency of new reps. How do you, how do you determine quality when sales efficiency is so difficult to manage with such long enterprise deals taking place?

A It's super fair. First of all, um, I think that like, I think we focus in sales too much on the lagging indicator, uh, is my comment to that. And the lagging indicator is revenue. And of course we're going to focus on revenue. Like at the end of the day, that's, um, why everyone gets hired, fired or promoted. But like a ton of stuff happens up until that revenue point. Um, and the better you can build out your sales process and your gas sales playbook, um, to have discrete measurable events. You can get signal on day one of a sales cycle. That deal may or may, like, 10% likelihood or five percent likelihood that it converts into anything that matters, and maybe it's a year from now, but you can know what, what are they doing with those first interactions, um, whether or not they're actually a fit for the organization or whether they're doing well. And that comes down to how well you have designed and structured the sales process, um, and how discreet and measurable each of those steps are. You want me to give you like a tangible example? Or is that too fluffy?

AI assessment note: “build out your sales process and your gas sales playbook, to have discrete measurable events”

Q I'm on many boards. I, I seem, obviously I'm invested in, I don't know, AC SaaS companies. The most common thing that I hear from founders and sales leaders is, ah, we didn't hit quota or target because they didn't feel it was urgent and it slipped into next quarter. What do you as a sales leader respond to that? I'm sure you see that a lot as an explanation.

A Well, at the end of our quarter, so I might be trying to make that excuse in a couple of weeks. We'll see how it goes. Um, but, uh, you know, urgency or, um, you know, it just wasn't important to them. All of those are subsets of pain, right? Like if you deeply understand a customer's pain, Then you know why they have to solve it. What happens if they don't solve it and why do they need to solve it right now? And if you can't get to that pain for the person that actually is going to make the decision, if you can't make that pain real for that customer and help them understand the consequences of not doing it, um, yeah, your deal is going to slip every single time.

AI assessment note: “urgency or, um, you know, it just wasn't important to them. All of those are subsets of pain”

Q It, it totally is. You mentioned the exploding discounting. Um, I, I totally get you not being a great customer experience. How do you advise sales leaders on using discounting? There's different views and takes on it. How do you feel about discounting?

A Um, early days, I don't care at all about what price people pay. ARR doesn't matter at all. There's a hot take from a sales leader, uh, early days. I think the only thing that matters is that you're learning and that you have good customers who are good fits that are going to drive your product forward. So they're either going to like say really good things about you in the market, talk to other customers, uh, or they're going to give you really good feedback and your product's going to be, be better because of it. But man, whether they give you 50 K or a million dollars, that doesn't matter. You know, in the grand scheme of things, if you're going to be a big company, that doesn't really matter. So like the way I think about discounting is, um, To answer your question in the early days is, um, I don't care that much about it. I care about aligning price to value and helping them and communicating upfront that, Hey, we're an early product and like pricing is going to change over time. I just need to make sure that you understand that. And I might put something in the order form to reflect that later on. And at the phase where like Monte Carlo's at, for example, now, Um, let's say you're at a hundred customers, um, pricing discipline becomes so important because customers talk to each other and customers don't want, they don't want to not pay a lot of money. They don't want to n…

AI assessment note: “the way I think about discounting is, um, To answer your question in the early days”

Q Yeah. In the interview process, how do you break it down and say, say you're potentially hiring me. Is it number one interview culture fit? Seeing if Harry's a good human, ambitious fit in that way to dig deep three, me pitched a team. How does it break down on an interview by interview? How many interviews does it take? When do you bring in different people?

A Yeah. Good question. So, um, maybe going back to that framework of, um, of culture fit skills and motivation. Um, so the first, the first interview, the screen is the motivation. Like, do you want to do this? Because this thing is hard. Um, like there's a lot of easy ways to make money. And so that's kind of my, like, I'm going to try to scare you off and see if you want to keep talking to us and if you're still excited. So that's the first thing of like, is there motivation aligned to come to Monte Carlo? Do we make sense for their career as much as they make sense for our career? Cause if you don't have motivation, this job sucks. Like just point blank, right? If you don't want to do it, it's not fun. Um, so I think that's like the first interview. The second interview is, um, is, is there historical track record? Is it a track record of excellence? Now I said attribution is really hard in sales and marketing, but you still aren't probably aren't going to hire someone who is middle of the pack or low performing historically throughout their career.

AI assessment note: “the first interview, the screen is the motivation... The second interview is”

Q What would you say are the biggest mistakes that founders you see make when it comes to specifically the timing and the type of first hires they make in sales?

A Um, I alluded to it earlier. I think it's, um, one is you're trying to solve a product market fit problem by hiring a salesperson. And so I, and I don't think that, you know, a founder would go into that hire and say like, I have a product market fit problem. I'm going to go hire a salesperson, right? They're going to say like revenue stalling or leads aren't progressing. Maybe if I go hire a salesperson that will solve that problem. Um, I think, so I think that like critical thinking of what problem you're trying to solve is probably the biggest one. I think the second biggest is, um, and I, and that informs like You know, the seniority and the type of person that you go and hire. Um, but I think the second biggest one is I don't think founders who I think sales and marketing are the two toughest groups of people to evaluate. It's so hard to attribute excellence to individuals. And like, let me give you like a dumb example. So, um, let's say this is not, this is not a real story, but I'll just make it, let's say I was the first sales rep at Twilio in like nine or whatever.

AI assessment note: “one is you're trying to solve a product market fit problem by hiring a salesperson”

Q Can I ask, what are the biggest or most common red flags you see when someone's not working out? What are the reasons it's obvious early?

A Impact. Everyone can make an impact in 30 days. Now impact doesn't mean that I'm closing a six-figure deal with like JPMorgan Chase in my first month, but they're actually having an impact. Impact might look like they're on customer calls and they're having an impact on that customer. Or they're looking at the sales process and they're having an impact on that sales process. Or they're raising the bar on the onboarding process and they're getting there faster than the people before them. If you're not seeing that, but you're seeing maybe people are like, oh, I developed the five X pipeline coverage where all of these like very soft things that TBD about whether they're high impact or not, or I put together like my book strategy. Ain't nobody got time for that. You need to come in and you have an impact immediately. And I think that you can tell pretty quickly whether or not someone's like actually jumping in and going in the right direction. Or they're flailing in the organization.

AI assessment note: “all of these like very soft things that TBD about whether they're high impact”

Q What would you say are the biggest mistakes that founders you see make when it comes to specifically the timing and the type of first hires they make in sales?

A Um, I alluded to it earlier. I think it's, um, one is you're trying to solve a product market fit problem by hiring a salesperson. And so I, and I don't think that, you know, a founder would go into that hire and say like, I have a product market fit problem. I'm going to go hire a salesperson, right? They're going to say like revenue stalling or leads aren't progressing. Maybe if I go hire a salesperson that will solve that problem. Um, I think, so I think that like critical thinking of what problem you're trying to solve is probably the biggest one. I think the second biggest is, um, and I, and that informs like You know, the seniority and the type of person that you go and hire. Um, but I think the second biggest one is I don't think founders who I think sales and marketing are the two toughest groups of people to evaluate. It's so hard to attribute excellence to individuals. And like, let me give you like a dumb example. So, um, let's say this is not, this is not a real story, but I'll just make it, let's say I was the first sales rep at Twilio in like nine or whatever.

AI assessment note: “one is you're trying to solve a product market fit problem by hiring a salesperson.”

Q Can I ask what are the biggest or most common red flags you see when someone's not working out? What are the reasons it's obvious early?

A Impact. Impact. It's all about it. Like everyone can make an impact in 30 days. Now impact doesn't mean that I'm closing a six figure deal with like JPMorgan Chase in my first month. Like don't mishear me here, but they're actually having an impact. Impact might look like, um, you know, they're, they're on customer calls and they're having an impact on that customer. Um, or they're looking at the sales process and they're having an impact on that sales process. Um, or, you know, they, they're raising the bar on the onboarding process and they're getting there faster than the people before them. So like, if you're not seeing that, but you're seeing maybe people are like, oh, you know, I, um, I developed like five X pipeline coverage, um, or all of these like very soft things that like TBD about whether they're like high, high impact or not, or I put together like my book strategy, like ain't nobody got time for that. Right? Like you need to come in and you have an impact immediately. And I think that you, you can tell pretty quickly, um, whether or not someone's like actually jumping in and going in the right direction, um, or they're like flailing in the organization.

AI assessment note: “all of these like very soft things that like TBD about whether they're”

Q Um, tell me, I, I spoke to, you know, incredible people on your team who, everyone agreed that actually it's your people management and the way that you make people feel was one of your really special points. When we moved to the post-hiring process, I heard that you have a Jordan Van Horn user guide. What the fuck is that, and what's in it?

A I'll send it to you after this. Um, it's, it's a public notion doc. So, um, yeah. So what, what I found is two things like one, um, working remotely and then having larger teams, it's harder and harder for people to understand my motivations and why I do what I do. Um, and this isn't, this is going to sound trite, but like I work because I love working with people and I love the relationships that will come out of it. Um, and I love being proud of something that we've built and, But like you tell that to a sales rep on their first day, they're like, okay, yeah, right. But like what happens when I don't have my quota?

AI assessment note: “it's a public notion doc... for people to understand my motivations”