Jordan Van Horn: 3 Reasons Salespeople Fail; How to Make a Sales Playbook | 20VC #918

1. 0:00 – 1:50

   Jordan’s Background

   1. HSHarry Stebbings0:00

      Three, two, one, zero. You have now arrived at your destination. Jordan, this is such a joy to do. As I said, I've heard so many things from so many different people, so I know a lot about you. And thank you so much for joining me today.

   2. JHJordan Van Horn0:19

      Yeah, it's a pleasure to be here. Thanks for having me, Harry.

   3. HSHarry Stebbings0:21

      Not at all, but I would love to start with a little on you, because, you know, we look at the LinkedIn CV and we see some incredible names of past institutions. So talk to me, how did you make your way into the world of sales? And then how did you come to join Monte Carlo most recently?

   4. JHJordan Van Horn0:36

      Yeah, I just kinda wandered into it, to be honest. Um, probably not too dissimilar from some of the other folks that, that you talked to that, that ended up at Dropbox at some point. Uh, I actually started in the wine industry. So I grew up in the middle of nowhere, um, and I was able to go to college because, uh, I got a scholarship at a winery called Gallo Winery, which you might've heard of. Um, and so they offered me a scholarship and I had to work there for a year outta school, and I ended up working there for three years. Um, and now it's just kind of like a party trick that I know a little bit about wine. But, uh, but back then it was a great, a great place to start my career. Um, my wife told me there was no way she wanted to live in the country with me, and so she made me move to San Francisco, and it's hard to be in San Francisco and not be in tech. And so, uh, so I ended up at Dropbox, uh, maybe back in the early 2010s. Uh, and from there, it's just been, uh, it's just been an amazing experience.

   5. HSHarry Stebbings1:23

      I mean, uh, you are now living in the country. And so I think you won that battle with your wife in the end I did win. 　 ... because you live in California. Yes, that's what matters. Go long.

   6. JHJordan Van Horn1:32

      (laughs)

   7. HSHarry Stebbings1:32

      Um, but I, I sp- I spoke to, I spoke to Zhenya before this episode, who you obviously worked with at Dropbox, and he's now at Miro.

   8. JHJordan Van Horn1:38

      Mm-hmm.

   9. HSHarry Stebbings1:39

      But he asked the question of, what did you learn from your job at the winery?

   10. JHJordan Van Horn1:45

       Oh, yeah. Um, well, it was a really amazing first year outta, outta school job because, like,

2. 1:50 – 4:00

   What Jordan Learned Working at a Winery

   1. JHJordan Van Horn1:50

      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, why 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 j- It, it humbles you a lot, and it gives you a perspective on how to connect to people in different, um, in 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.

   2. HSHarry Stebbings2:20

      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?

   3. JHJordan Van Horn2:31

      Yeah. Uh, the first one is, um, from Dropbox, I think startups live and die, uh, by simplicity and clarity of thought. And so, uh, Dropbox is this amazing company with an amazing outcome, and it built one of the best teams I've ever been a part of. Um, but I would say that Dropbox did struggle at times with their core identity of whether it was a consumer company, uh, or whether it was an enterprise sales company. And so I, I think that we spent a lot of cycles, um, and we missed a lot of opportunities because we didn't have that clarity, uh, of conviction. And, and, and Segment was, was really different. I think, um, you know, that was a career-changing experience for me as well. A- and at the risk of sounding trite, I think I learned in that role the importance of, um, becoming really great at hiring. So I worked for Zhenya, and I hired 100 people plus just reporting to Zhenya, and he actually interviewed every single person and just, like, rode me so hard, um, on keeping the talent bar super high. And, 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. As a leader, um, you're not gonna have every single skillset, and you're not gonna be great at everything. You, 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. And, and Segment taught me to do that. Um, you know, I learned that from Peter, I learned that from Zhenya. And, and a lot of these folks, actually, you know, I work with today still at Monte Carlo, and they're some of the most talented folks that I've ever worked with.

   4. HSHarry Stebbings3:51

      I mean, Zhenya is just a machine. I loved it when he talked about the hiring panel that he assembles for each hire. I thought that was-

   5. JHJordan Van Horn3:57

      Mm-hmm.

   6. HSHarry Stebbings3:58

      ... really terrific. We're gonna get onto talent

3. 4:00 – 5:18

   What is a “Revenue Leader”?

   1. HSHarry Stebbings4:00

      evaluation. I do wanna start on just some nomenclature though, because I think it's helpful to really just get a foundation.

   2. JHJordan Van Horn4:06

      Yeah.

   3. HSHarry Stebbings4:07

      Res- respectfully, your title is, like, revenue leader. Um, what does that mean? How is it different from-

   4. JHJordan Van Horn4:13

      (laughs)

   5. HSHarry Stebbings4:13

      ... a head of sales or a CRO? I was looking at it, and I was like, "Uh, what does that mean?" No offense. (laughs)

   6. JHJordan Van Horn4:20

      Yeah, I don't, I don't know what it means either. I'm with you. Um, it, 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, 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, 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 wanna, 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-

   7. HSHarry Stebbings5:06

      (laughs)

   8. JHJordan Van Horn5:07

      ... so head of revenue i- is fine for now.

   9. HSHarry Stebbings5:09

      Okay. So we have head of revenue. That's one nomenclature relatively solved in a very unclear way. Thanks for that, Jordan. Um, (laughs) -

   10. JHJordan Van Horn5:16

       My pleasure.

   11. HSHarry Stebbings5:16

       ... uh, uh, but my next one is

4. 5:18 – 6:10

   What is a Sales Playbook?

   1. HSHarry Stebbings5:18

      sales playbook. Love the word sales playbook. How do you define ... What actually is a sales playbook, Jordan?

   2. JHJordan Van Horn5:25

      So a 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 gonna drive, you know, some sort of critical business outcome for that customer. Uh, the third s- is to gain consensus across team members involved in that decision-making process. The fourth is to agree and formalize a 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.

   3. HSHarry Stebbings6:00

      Okay. So that's a sales playbook. Should that be created by the founder, or can this be created by an early sales team instead?

5. 6:10 – 8:23

   Who should create the Sales Playbook?

   1. JHJordan Van Horn6:10

      So, I think that you're gonna have dozens of versions of a playbook over time. And so, um, I think there's a V0 and I think there's a V20, right? And so in the early days, you know, those playbooks need to be really open-ended and they need to make space for all the things that you don't know. I- in the later days when you're prom- the problem that you're trying to solve is, "I need to go hire and onboard 25 AEs, and they need to know specifically what to do," you're getting very, very, um, prescriptive around, like, what are scripts that you use? What specific questions do you ask? And you're trying to, um, you know, grow the company through, uh, making sure that people onboard really quickly. So, to answer your question, I think 100%, a leader of an organization, a founder is accountable for that V0 of that playbook. And that V0 should really only clearly document three things. Uh, they're just the foundational go-to-market pillars. They are, what problem are you trying to solve, and who are you trying to solve it for? And also, by the way, it's really important for that founder to document who you're not trying to solve the problem for, because that's gonna be a direction of how you actually focus the sales team that you go and hire. Um, two, what are the wins, losses, points of resonance with the customer? What are the key things that are factors for success in your sales process? You should have a very clear point of view of what that is, the founder, and you should know it better than your sales team. Uh, and then the third thing is, what are the two or three reasons why people, uh, wanna focus on that- solving that problem with your solution right now? Um, why not do it in six months? What are the reasons they came in? And so like, it doesn't have to be pretty, it doesn't have to be precise, it doesn't have to be formal. Um, but I'd argue that no matter how successful a company is, the best founders in the world are accountable to s- to answering those three questions in perpetuity. Not at, just at seed stage, but at series A, series B, series C, as a public company. Now, eventually your sales leader's gonna come in and they're gonna be focused on, "Okay, how do I make this like AV1, AV2? How do we get more detailed and more dynamic? How do I ask better discovery questions?" You don't need to do all that stuff as a founder. That stuff, like, someone else can do that, and they'll do things better than you are. Um, but those foundational things, I think you owe that, um, what- you owe that to a sales team from a founder-led sales standpoint.

   2. HSHarry Stebbings8:16

      I was writing on my hand. I don't know if you can see. I was writing on my hand follow-up questions.

   3. JHJordan Van Horn8:21

      (laughs)

   4. HSHarry Stebbings8:21

      The- my, my, my first follow-up question to

6. 8:23 – 10:12

   Is it OK to have your product be for everyone?

   1. HSHarry Stebbings8:23

      you is... You said about the understanding the who, who it's for. My challenge here is a lot of products that we see today, it could be your Notions of the world as a great example-

   2. JHJordan Van Horn8:33

      Right.

   3. HSHarry Stebbings8:33

      ... are incredibly horizontal. Is it acceptable-

   4. JHJordan Van Horn8:36

      Mm-hmm.

   5. HSHarry Stebbings8:36

      ... to say everyone, Dropbox, I mean, storage? How do you think about how precise and clear the who needs to be, especially when it could be horizontal?

   6. JHJordan Van Horn8:48

      Yeah, great, great question. So, a- and, you know, I think the, the context, the lens that I'm looking through today at Monte Carlo is a very specific enterprise tops-down sales motion that's focusing on one specific team, right? And that's why we don't have, um, you know, a product-led growth model. It's like all 100% sales-led growth. Um, and so just by going back to your question, you know, who doesn't necessarily need to mean who are the users within an organization? Who is, who is the person that actually makes the decision, uh, from a monetization standpoint? Because we're talking about sales, we're not talking about like, product adoption or usage. And who are the companies that are early adopters or the adopters at that stage of the product? So for example, if you don't have a clear point of view, if your Notion, you know, three or four or five years ago, whenever they started growing, you probably weren't jumping out of the gate selling to banks, right? Like, you probably didn't have single sign-on. You probably didn't have all those things that like, a Notion needs to go sell to those companies. And so y- the first reps that you come in probably shouldn't be talking about million dollar deals with like, HSBC, right? And so like, I think who can be, who can be loosely defined, but you do have to focus people down. I think that's the point of who. It's like you have limited hours in a day and you can only talk to so many people. Who are the highest value people that you should talk to? And so I would divorce that out from your c- like, the question, like, who gets value from the tool? Um, because a lot of times it is different, right?

   7. HSHarry Stebbings10:09

      I totally get you. The next, next very

7. 10:12 – 12:18

   How to document what resonates

   1. HSHarry Stebbings10:12

      intellectual and strategic question that I have for you is, you said about points of resonance. Um, what are the best ways for me to document this? I'm a founder building the first three step V- V0 playbook. How do I document the things that resonate? Is it by doing like, memo notes post-calls? Is it by recording sales calls? For you as a sales leader coming into hopefully my company, what would make you go, "Ah, fantastic. He's documented what resonates and what doesn't"?

   2. JHJordan Van Horn10:41

      Yeah. The, the best gift you can give to a salesperson coming in, uh, is a subset of recorded calls. Um, the second best gift is for you to continue to take calls and have that person shadow you. Um, and so, and I think those points of resonance, they, they come out consistency and you're looking for, for- consistently and you're looking for themes. Uh, so the, the few things that I would document is, one, for every call that someone takes, a simple question is, "Hey, why'd you take this call?" Right? Like, you, you have a million people reaching out to you. Like, why, why are you talking to me right now? Like, what did I say in my messaging that was resonant for you? Um, and what you'll find is, by the way, you'll find like, everyone takes calls for a subset of reasons. So Monte Carlo has like, three reasons why people like, even just got on the phone with us, right? And those thing- those three reasons why they got on the phone with us are eventually the three reasons they end up buying the tool. And those things actually go back and they, if you, you can map those things back to the problem that you're actually solving for a customer. "Hey, I took your call because boom, this made sense. This is something I'm thinking about right now." Tell me more about that, right? Like, and just open-ended questions. And the more that you can document that and the more you can, like, put them into broad categories, like, rules of three are very simple. Salespeople are very simple people, don't give 'em 50. If you can give us like, three categories of like, "Hey, this is like, archetype one, archetype two, archetype three, and here's like, 20 th- 20 companies that prove that archetype," that's amazing for salespeople, right? They can like, run with that and figure out, okay, who am I talking to? And now I can ask this line of disc- discovery questions or, you know, go down this path.

   3. HSHarry Stebbings12:13

      I totally get you. The third and final element that I wanted to discuss on this core point was,

8. 12:18 – 14:00

   Most common excuse for not hitting quota

   1. HSHarry Stebbings12:18

      you mentioned kind of like why buy it now? Why the urgency? I'm on many boards. I, I see Obviously, I'm invested in, I don't know, 80 SaaS companies.

   2. JHJordan Van Horn12:26

      Mm-hmm.

   3. HSHarry Stebbings12:26

      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.

   4. JHJordan Van Horn12:38

      Right.

   5. HSHarry Stebbings12:38

      What do you as a sales leader respond to that? I'm sure you see that a lot as an explanation slash-

   6. JHJordan Van Horn12:43

      (laughs) Well, it's 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, uh, 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's gonna slip every single time, right? And so, the, the backup plan is always, okay, I will either give you an exploding discount, it's 50% if you sign today, and it's like no discount if you sign tomorrow. That's a horrible customer experience. Um, or your option is to lean on your relationship. "Hey, listen, this is really important to me. This matters to me." Um, and, and you know what? That, that second one is not to be underestimated, right? Like, people buy from people. And I think at the end of the day, uh, you know, customers, if they value your product, they wanna start the partnership off on a good foot. And so, um... But I would say that if you don't have that reason that someone's gonna make money, save money, reduce risk, or go to market faster, if you don't have that thing, it's gonna be hard to push

9. 14:00 – 16:10

   How do you advice sales leaders on discounting?

   1. JHJordan Van Horn14:00

      a compelling event on someone.

   2. HSHarry Stebbings14:02

      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?

   3. JHJordan Van Horn14:14

      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 gonna drive your product forward. So, they're either gonna, like say really good things about you in the market, talk to other customers, uh, or they're gonna give you really good feedback and your product's gonna be, be better because of it. But man, whether they give you 50K or a million dollars, that doesn't matter. You know, in the grand scheme of things, if you're gonna 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 pr- aligning price to value and helping them un- and, uh, communicating upfront that, "Hey, we're an early product, and like, pricing's gonna 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, and at the phase we're like Monte Carlo's at, for example, now, um, let's say you're at 100 customers, um, pricing discipline becomes so important because customers talk to each other. And customers don't want, they don't wanna not pay a lot of money. They don't wanna not pay you 100K. They wanna know that you're not fleecing them, right? They wanna know they're getting a fair price. And so, as, as disciplined as you can be around discounting, um, I think that actually leads to a better customer experience. Like, you can have two customers, one gets a 20K discount and one gets no discount. Like, that doesn't mean the person with the 20K discount's gonna get a better experience or be happier with you, right? If they don't feel like they got a good deal. Um, and so I think aligning price to value is really critical. Um, you have to get to a point at some point where you're okay with the fact that some customers, based on their business models, might not see value from your product, and it might not be at that price. And so, that's a price and a packaging problem. But solving it through just, like excessive and, and wanton discounting, like that, that's super problematic from a customer experience standpoint.

   4. HSHarry Stebbings16:06

      You... I, I totally agree with you. I mean, God, that, it's a challenge, especially as you scale and-

10. 16:10 – 18:00

    What do you do when your champion leaves? Multithreading?

    1. HSHarry Stebbings16:10

    2. JHJordan Van Horn16:10

       Right.

    3. HSHarry Stebbings16:10

       ... customers become more significant. Question, you said about leaning on the relationship. The other big excuse I hear is, "Ah, we would have signed it, but our champion left." Um, how do you approach and feel about multi-threading, in other words having, you know, many champions within an org, um, to prevent that churn when the champion leaves?

    4. JHJordan Van Horn16:30

       Ch- champion left is brutal. Um, it, it really is. So, I, I think that it, first of all, it depends on the size of deals that you're, and the complexity of deals that you're operating on. Uh, it doesn't make sense to build like this multi-threaded, overly engineered, um, you know, go-to-market motion when you have a $4,000 ASP, right? And so for those, for those lower end of the markets, be single threaded, that's fine, but just move quickly, 'cause time kills all deals, right? And so, like compress those, compressing those deal cycles down is actually far more important than multi-threading, now, uh, so that you're basically minimizing the window for something to go wrong. And so, on the upper end, like you have to multi-thread. You have to have multiple stakeholders. You have to have a person. Even if you get the deal and the champion leaves, you're still screwed, by the way. You still have to go roll out that product and get it adopted and used. And if your adaf- and if your champion's gone, like guess what? You got churn risk on day one of the contract. So, I think it is really critical to, um, to have a champion, to have a, uh, practitioner who's going to deploy it, and to have an economic buyer in the organization, and have access to all three of those parties and make sure that they are all on the same page. I think that's ge- quickly becoming the role of an enterprise sales rep, like the, the pure role. And insofar as you can get multiple champions or, uh, you know, even like a department being a champion for something, uh, that's, that's a significant backup plan.

    5. HSHarry Stebbings17:49

       I think you're so right there. I think that's the common notion that once the deal's signed, it doesn't matter. It's fine. We don't need, we don't need to worry about it. You're so right. If your champion-

    6. JHJordan Van Horn17:57

       Yeah.

    7. HSHarry Stebbings17:57

       ... leaves, you are fucked.

    8. JHJordan Van Horn17:58

       Right.

    9. HSHarry Stebbings17:58

       Um, (laughs)

11. 18:00 – 22:30

    When is the right time to hire first Sales hire?

    1. HSHarry Stebbings18:00

       but I, I, I wanna ask, like pretend that I'm a, a angel investment of yours and I'm a first-time founder building my sales team. When is the right time to hire our first sales hire? What are the core signs that now is the right time?

    2. JHJordan Van Horn18:15

       (laughs) Yeah, um, and, and I've listened to the answer from other folks on, on this and they're all, like, like, slightly different, right? And so it's like I think we're all looking for a formula, and I wish there was one. I'd love to give it to you. Um, but I think, like, so much of hiring any sales leader, uh, it comes down to, to, like, two things, like luck and timing, uh, and two, like, what your business needs. And so, like, I would always ask you if I was your angel investor, um, I would ask you, "Hey, what problem are you trying to solve with hiring a sales... Why do you wanna hire a salesperson?" Right? I think that's-

    3. HSHarry Stebbings18:42

       Yeah.

    4. JHJordan Van Horn18:42

       ... like the first really critical question of what are you trying to solve. Because, okay, if it's product market fit you don't have and you think hiring a salesperson is gonna help, it ain't. Like, it's not gonna help you, right? Don't hire a salesperson. If it's you're in a competitive market scenario, you're a fast-moving market and you have, like, all these free signups and you wanna amplify the number of conversations and learning, um, or, or you wanna bring in an expert and that you hope that expertise could come in and increase, like, your revenue per lead, um, it's probably time, right? And so, like, um, you know, the first thing that I would say is if you know you-

    5. HSHarry Stebbings19:14

       It's very, very simple for me. I'll... On, on this one here, the most common one for me is I'm doing product, I'm doing fundraising, I'm doing engineering-

    6. JHJordan Van Horn19:22

       Right.

    7. HSHarry Stebbings19:22

       ... I'm doing marketing. Like, managing sales pipe and managing the inbound and managing the sales process is just too much. It's almost-

    8. JHJordan Van Horn19:31

       That was the-

    9. HSHarry Stebbings19:32

       ... like flying without a map.

    10. JHJordan Van Horn19:32

        ... that was the, that was the third one. That was the third one I was gonna get to.

    11. HSHarry Stebbings19:35

        Yeah.

    12. JHJordan Van Horn19:36

        Uh, yeah, that's the, that's the other one. So let, let's go straight to that one, since that's the one you hear the most. Um, so I think that that's, like, that's a you question not a sales question. Right? That has nothing to do with go-to-market. Uh, that's where you wanna spend your time. And do you wanna spend your time building a product or, or in front of customers? Now, now I'd argue that they don't think that you're gonna hire a salesperson and go save a bunch of time instantly. Right? Um, maybe you have, like, a fast transactional deal and a bunch of inbound volume and you need someone who's just gonna process and transact. Okay. Go hire sales p- Hire a sales leader, right, that's gonna build out a junior sales team, if that's the case. Um, but if you're just trying to, like, step away from it because you have other things you wanna worry on, like, hiring people doesn't make your life easier. Right? We had a saying at Monte Carlo in the early days, like, "Every time you hire someone, you failed." Right? Like, because you, like, couldn't solve the problem with the people that you had on the boat, so you had to go hire another person. And that, I think, shifts people's thinking in terms of how you think about solving that problem. So I would say, you know, for that founder who's like, "I've got a million things. I just need help," if you have a transactional business, yeah, you're probably ready. Um, you could probably go hire a, a senior or, like, a mid-level head of sales that can go build out a team really quickly. Um, or if you're, like, an enterprise in motion, you could probably go hire a person that, that needs, like, minimal supervision. Um, but you're still gonna spend 25% of your time with customers, right, or prospects. Like, that's not gonna change. That's not gonna change for six or nine months. So, um, just to set expectations, like, good luck walking away from sales.

    13. HSHarry Stebbings21:00

        What, what are the other two? You mentioned that was the third and-

    14. JHJordan Van Horn21:03

        Mm-hmm.

    15. HSHarry Stebbings21:03

        ... I jumped straight to it. What were the other two?

    16. JHJordan Van Horn21:04

        No, no. It, it's fair. Uh, yeah, so the other two are, one, um, you actually believe that by bringing in a professional salesperson, um, you're gonna get more revenue per lead. Right? Um, I have a subset of leads. I know because of-

    17. HSHarry Stebbings21:17

        Wow. Very cool.

    18. JHJordan Van Horn21:17

        ... there, there's a person because they're gonna process it better. They're gonna- you're gonna get better results. Um, and that one is a, a clear... Like, you have to, one, I think there's three things that you need. You need, one, like, four or five customers that you've made successful, that have paid you and said, like, "Yeah, it was worth the money," even if it's $500. Right? Doesn't matter. Um, the second thing you need is you need to be able to repeatedly generate, uh, you know, call it five to ten leads a le- leads a week. I don't know. I'm, I'm estimating here. And then the third thing that you actually need is you need to make sure that those leads are actually progressing from the discovery phase to the evaluation phase, um, and that... those early leading indicators. If you have those things, you can probably hire, hire someone and they are gonna actually do better than you're doing as a seller. Now, if the fir- the other one that, you know, people, uh, will typically hire salespeople are in is, like, you have a competitive market scenario, it's a fast-moving market. Um, you might have things where, where you wanna, where you just, like, need to transact or you just want, like, a lot of conversation to start happening. You wanna, like, amplify, uh, your message. Uh, y- That person's gonna be, like, kind of a marketer. Right? And that's okay. That's okay. Just, like, have the expectation that person's a marketer. Right? Um, and, but, like, what problem are you trying to solve?

    19. HSHarry Stebbings22:28

        Well, I mean, I think what problem you're trying to solve

12. 22:30 – 24:16

    How to know whether to hire experienced or junior?

    1. HSHarry Stebbings22:30

       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?

    2. JHJordan Van Horn22:46

       Yes. So three variables to that. I'm not gonna 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, y- the level of involvement that you want. So, like-

    3. HSHarry Stebbings23:04

       Mm-hmm.

    4. JHJordan Van Horn23:04

       ... um, to maybe to g- to dive a little bit deeper, if you have really transactional deals, your ASPs are, let's say, sub 12K, 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? Like, it's, it's fairly simple. Um, so it's really the degree... it's, it's your willingness and readiness to go and hire people because, like, honestly, heads of sales, if you go too senior on a head of sales, they don't know how to sell anymore. I haven't carried a bag since, like, 2012. Like, it's been 10 years since I had, like, a individual quota on me. Right? Like, everyone on my team is better at selling than me. And I j- I just wanna, like, call that out of, like, hiring that head of sales, there's some benefits to it, and it's if you want to grow a team really quickly, um, and you want to attract talent, that, that's the right time to do it. But if you just want a really good salesperson, don't just think you're getting a head of sales because it's gonna be easy to manage. Like, they're gonna do things that don't matter. They're gonna, like, implement Salesforce or something stupid that you don't need when you're a five-person

13. 24:16 – 26:30

    Biggest mistake founders make with their first sales hire

    1. JHJordan Van Horn24:16

       company.

    2. HSHarry Stebbings24:17

       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?

    3. JHJordan Van Horn24:27

       (smacks lips) 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 gonna go hire a salesperson." Right? They're gonna say, like, "Revenue's stalling," or, "Leads aren't progressing. Maybe if I go b- hire a salesperson, that will solve that problem." Um, I think... So, they think that, like, critical thinking of what problem you're trying to solve i- is probably the biggest one. I think the second-biggest is, um... And I... And that in- 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, 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 up. Let's say I was the first sales rep at Twilio in two thousand, like, nine or whatever, right? And I go close, uh... What do I do if I'm the first rep at Twilio? Well, I go close, like, Uber and Lyft and Airbnb when they're 15-person companies and they just need, like, a messaging service, right? And it's, like, a transaction on the credit card or whatever. And then I ride that wave for the next six years, right? And those com- those customers turns in, into $10 million, $20 million, $40 million customers, right? Like, if you look at my resume, you'll say, "Okay, this person's been at a great company and they've been the number one sales rep for six years consecutively. Uh, clearly, it would be a major coup d'etat if I could get this person to join my team." That person might not have done anything at all, right? And I think that is so true in a product-led, especially in a product-led sales era of, like, understanding how someone actually got to the results that they did, um, is a really critical thing. And I think it's really hard for founders to decouple the brand names on, um, on someone's resume versus what that person actually did at that company.

    4. HSHarry Stebbings26:20

       I mean, I, I wanna kind of dive into that a little bit, 'cause I wanna get into the hiring process with you-

    5. JHJordan Van Horn26:24

       Mm-hmm.

    6. HSHarry Stebbings26:24

       ... 'cause it's really fucking hard, especially if you've-

    7. JHJordan Van Horn26:26

       It is.

    8. HSHarry Stebbings26:26

       ... never done it before. And so, if we think about the process itself

14. 26:30 – 35:34

    How to structure the hiring process for Sales

    1. HSHarry Stebbings26:30

       for adding new people to your sales teams, can you just break it down for me? Imagine, literally, the day dot I need to hire new sales hires. What... How do I structure this hiring process, Jordan?

    2. JHJordan Van Horn26:44

       Yes. So salespeople fail for three... So, I, I always approach things through the lens of failure. Um, it's what drives me. Um, so-

    3. HSHarry Stebbings26:52

       (laughs)

    4. JHJordan Van Horn26:53

       ... salespeople fa- (laughs) It's, it makes for a horrible night's sleep. Uh, salespeople fail for three reasons. They either, um... They don't fit within the organization. They d- they, uh, they maybe can do the work, um, but they might take the company in an entirely different direction than you want as a founder. Um, they have a motivation problem. They, they don't wanna do the work. They got there. Th- they, uh, it seemed cool to start a, join a startup. Then they came in, they're like, "Oh my gosh, I have to do everything," right? And the third thing is, they just... They're just not that good. Like, the skillset... Or, or the skillset isn't aligned with what you actually need from the organization, so you're not able to do the work. Cultural fit, um, and motivation. I think, um, those are actually definitional things that you need to have set out ahead of hiring any human being, much less sales, right? Like, you need to do the work upfront to define how you do things, and you need to care enough about what your culture is to see how, like, a person is gonna positively or negatively impact that culture. And so, like, starting with a clear understanding of who you are i- i- is paramount. Otherwise, this person's gonna drive you nuts and you're gonna have no idea why. And then, like, both of you will want that person to quit within three months. Uh, the second thing is motivation. And, and so, uh, you know, your question's like, how do you structure an interview process? I think early on in that interview process, the temptation is just to sell the dream of what the company could be, and I think that's important. Um, but you also have to sell the reality of, uh, of where you're at. You have to sell what's hard about it. So, like, I start every first interview, I don't know if this is a good iron fact or a bad one, but I say, like, "Oh man, we have problems." Like, "Let me walk you through all of the things that are wrong at Monte Carlo and all the things that we need to fix in the next six months." And I just, like, lay it out. And the person whose eyes light up and is excited about that, that person belongs at Monte Carlo. The per- the person who's like, "Well, yeah, like, tell me, like, how many leads I'm gonna get a month," I'm like, "You're not gonna, you're not gonna make it here." Like, you know what I mean? Like, leads might come, they might not come. We're two years old, I don't know. Uh, so I think that, like, that, like, telling people the truth and letting them self-select in and self-select out and using what we call in sales negative pressure, letting them sell you on why they still wanna be part of this thing even though it ain't perfect, um, is super critical. And then if you wanna get them pumped and excited, use board members like yourself to go sell them why this is gonna be the next, like, $40 billion company. But, like, early on, like, I want people to see the dumpster fire that, like, they're walking into. Uh, what?

    5. HSHarry Stebbings29:08

       I will be a closer for you, baby.

    6. JHJordan Van Horn29:10

       Yeah.

    7. HSHarry Stebbings29:10

       Bring me in. I'll, I'll close them.

    8. JHJordan Van Horn29:12

       Yeah.

    9. HSHarry Stebbings29:12

       Yeah, bring it in.

    10. JHJordan Van Horn29:12

        That's right. That's your job. That's, like, that's a great use of the board. Uh, and... But the third thing, then the third thing is the hardest one, uh, and so, um... And that's, like, the skillset misalignment. And I think that, you know, that Twilio example that I just gave, like, i- i- is, is the problem, right? Like, and so, um, what I think founders need to do is they need to make sure that they're going very, very deep on past experiences. Zhenya said this a few weeks ago, right? Like, he said, like, "I don't do, like, the forward-looking case studies anymore. I go really deep on a relevant experience." And what I mean by really deep is, like, you are asking fourth and fifth and sixth-level questions to that person. "Hey, I saw that you did 183% of your number in twenty- 2018. Tell me how you got to that number," right? "What did you do? What did other people on your team do? How is that relevant to what other people did in the organization? What were the deals that made that up, and what did you do on that deal? What's the deal that you're most proud of? What are the things that you could have, would have done different, you could have learned from? Well, then I saw you dip down to 175% of your number next month, next quarter. What happened there?" Right? Like, going like that in depth into what specifically they did, and then there, there's, like, a key question that I think gets to all skillset, um, that ha- has been the most powerful question that I ask. It's...... what was hard about it? Because that question gets to the root of what that person actually did and why their skills are relevant to your company. And so, like for example, the Twilio example I just gave, what's hard about it? Like, I don't know, I had to send a contract, and there were 20 people and there was no legal department. So like, in, and it was hard to tell them that they had to 10X their contract. Like, that was hard. That was a tough conversation. But the person that's like, "No, I had to go talk to, like, 15 different people, and I had to bring, like, engineering involved, and I had to get my CTO involved. And, like, there was this one person who was trying to buy a competitive scenario, like a competitive product, and there were 15 different companies popping up at the time. We had no idea what their differentiators were and how we were differentiated." That person is, like, your person that's made of gold. Like, they went through some hard things, and they're gonna come in and they're gonna really perform well for you.

    11. HSHarry Stebbings31:18

        Uh, I, I love those questions, and I think they're really granular and deep, and really pick at the heart of, like, what makes true quality salespeople. Do you use case studies? Do you use any form of tangible test which you give people to really determine their quality?

    12. JHJordan Van Horn31:36

        Not in sales. Um, candidly. I, we do a, um, we do a presentation, like a pitch at the end.

    13. HSHarry Stebbings31:45

        Yeah.

    14. JHJordan Van Horn31:45

        And I hate it. I've been trying to kill the pitch presentation interview for, like, seven years. And, uh, sa- my sales leaders just won't let me do it. So, like, that's the closest thing to it, but I'd say, like, 90% of our interview is looking back at relevant experiences and trying to find patterns in that person's background and how they perform, how they relate to others, and how they, like, use the experiences that they have to acquire the skills that we know that they need to be successful in our company. And case studies don't really-

    15. HSHarry Stebbings32:13

        Can I ask-

    16. JHJordan Van Horn32:13

        ... get that. Yeah?

    17. HSHarry Stebbings32:15

        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, g- fit in that way? Two, dig deep, three, me pitched to team? How does it break down on an interview by interview? How many interviews does it take?

    18. JHJordan Van Horn32:34

        Yup.

    19. HSHarry Stebbings32:35

        When do you bring in different people?

    20. JHJordan Van Horn32:37

        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 gonna try to scare you off and see if you wanna keep talking to us and if you're still excited. So, that's the first thing of, like, is their 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 wanna do it, it's not fun. Um, so I think that's, like, the first interview. The second interview is, um, is, is there a historical track record? Is it a track record of excellence? Now, I said attribution's really hard in sales and marketing, but you still aren't, probably aren't gonna hire someone who is middle of the pack or low performing historically throughout their career. Like, eventually, luck's gonna turn, right? And so, you're looking for p- someone who has ha- had susta- sustained success across their career and then they actually, you're going deep on that success. Did they actually do it? Were they just, like, on a rocket ship and on, on for a ride? That's the first interview. That happens with the hiring manager before they get to talk to anyone else. So ideally, when they go to our, it used to be an onsite, now it's not an onsite anymore, um, but, uh, when it goes to our onsite where they meet other people the manager has vetted, is this person a cultural and motivational fit, and do I believe that they have the, it's possible that they are excellent? Like, if you get tha- those two checked off, you're gonna, like, half the people that end up going to talk to the rest of the team will end up getting hired, because that's, like, that's the, the meat of it. Then the onsite is three interviews. Uh, it's typically with, um, you know, one person who's actually doing the job, um, a different manager who's not involved in the hiring process, and then, like, a cross-functional person. Um, and you're, and you've ideally identified two or three competencies that this person needs to have. And each of those interviews is focused on going really deep on one of those competencies. And so, I might say, "Okay, Liz, you need to be, you need to give me a high degree of confidence that this person has tolerance for ambiguity." Right? Like, let's just say, for example.

    21. HSHarry Stebbings34:41

        Mm-hmm.

    22. JHJordan Van Horn34:41

        And there's a structured interview in how she does it, and there's, there's a score, and then, uh, I stole this from Virginia, by the way. Um, and, uh, and so then when we all get together in that debrief, we're like, "Okay, this person has the skills and the competencies, they have the motivation, they have the cultural fit," um, you know, the, then that last step, if we give a go, then they go to the presentation. And, and ideally, the presentation is giving them a good experience of what it's like to work at our company. So, the presentations work for them. Uh, it's a final test on motivation. It's a final test on just, like, hard skills. Um, but most importantly, like, you know, we give them all the information. We say, "You can talk to anyone in the company you want. All the resources are yours." And they can see, they can, like, see what it's like to work with us. Like, I let any candidate call me and say, "Hey, what's the answer to the test?" Right? I'll give you the answer. Like, that, you get an A+ for asking the question. 'Cause it's not like I'm, I'm not gonna get hit by a bus the day you start. Like, I'm still gonna be here, and I'm gonna be part of you being successful. And so, that's th- and then

15. 35:34 – 36:37

    What makes the best presentations?

    1. JHJordan Van Horn35:34

       that, that's the last step of the interview process.

    2. HSHarry Stebbings35:36

       What makes the best presentations and what makes the worst, in your experience?

    3. JHJordan Van Horn35:41

       Um, discovery makes the best. Right? Conversational discovery. Like, someone's curiosity, ability to ask questions and hold cour- like, no one wants to sit around and listen to someone talk for an hour. Right? Like, so if you're able to ask, like, good questions and, and get to truth, and you demonstrate that you can do that in a presentation, I know that's, like, counterintuitive 'cause you're presenting something, um, that's the most important thing. Um, you know, I think that the worst ones are, I'm, this is like a book report and I wanna show you that I learned all the content. Right? I wanna show you that I know the answers to the test. And you're, you get this from all the, all, like, the Ivy League, and for you, our friends across the pond, the Oxford folks, so, like, those are the folks that got the A+'s all day. Uh, like, they're gonna give you the answers. And I want the answers. Right?

    4. HSHarry Stebbings36:28

       We'll get on. I would rock up hungover, say that we should all go for a tequila-

    5. JHJordan Van Horn36:32

       (laughs)

    6. HSHarry Stebbings36:32

       ... and sod off this presentation anyway. And I'll sell you over some tequila, baby.

    7. JHJordan Van Horn36:35

       There you go.

    8. HSHarry Stebbings36:36

       Let's put it that way.

16. 36:37 – 39:08

    Jordan’s Biggest Hiring Mistakes

    1. HSHarry Stebbings36:37

       (laughs)

    2. JHJordan Van Horn36:37

       There you go. All right.

    3. HSHarry Stebbings36:38

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

    4. JHJordan Van Horn36:47

       Yeah, definitely. Um, so there's probably two or three. Um, the first one is veering from a hir- 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 might ... 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 wanna show that I can go get this person." So I'm gonna go just, like, skip a few steps in the interview process, and, like, try to, try to win them, right, and just try to sell them. So that's one. And it happens all the time, right? Your founder is gonna say, like, "I think this person's world-class. We need to hire them." Like, every time I've, like, gone with that and veered off from my process, I have regretted it just deeply. So I think that's one of, like, sticking to your process no matter what people say. Um, that's the first one. The second one i- was I didn't adequately, uh, run reference checks, right? And so, um, you know, we're pretty good at getting to the truth in the interview process, um, but those reference checks are just so valuable. And so running, like, two or three references ... Like, at Monte Carlo, we reference everyone. It's, like, company policy. You have to do it. Uh, that's the second one. And the third one is, uh, not having a clear idea of what you want and not having conviction on what t- what makes the role. And then so what you do in those situations is you bring, okay, let's bring, like, 15 people into the hiring process and, like, by some consensus, we will find the best person. That always goes wrong too. So it's, like, slowing down on that one, getting really clear about what the person that you need in this organization, and then keeping that decision-making group to less than six, uh, i- is the third thing that's just so important.

    5. HSHarry Stebbings38:20

       Do you know what's funny? I would say the biggest mistakes that I've made in investing are the exact same ones-

    6. JHJordan Van Horn38:25

       Really?

    7. HSHarry Stebbings38:26

       ... as you're just saying. Yeah, pretty much.

    8. JHJordan Van Horn38:28

       Interesting.

    9. HSHarry Stebbings38:28

       Skip a step. You skip a step because it was sent by x, you know, domain expert, and they say it's fantastic. You skip a step-

    10. JHJordan Van Horn38:35

        Right.

    11. HSHarry Stebbings38:35

        ... on referencing for sure. Absolutely, very, very much aligned. Um, or, or the final one is-

    12. JHJordan Van Horn38:41

        Yeah.

    13. HSHarry Stebbings38:41

        ... that you, you just ... You're not confident enough, and so you bring loads of other people in 'cause you need to get the confidence. And actually, if you're looking for confidence in someone else's answer, you're probably saying a lot about yourself.

    14. JHJordan Van Horn38:52

        Yeah. That's a really good point. Well, I imagine it's even harder in, in your world because, you know, you also have the FoMO factor of investing, right? You've got, like, four other VCs that are pitching this person. You don't want to be the skeptical one that's telling them, "Your baby looks a little ugly over here." Uh, so i- i- I can imagine that's

17. 39:08 – 42:12

    The Jordan Van Horn User Guide

    1. JHJordan Van Horn39:08

       a, that's a hard skill. I couldn't do that.

    2. HSHarry Stebbings39:10

       Um, tell me. I, I spoke to, you know, incredible people on your team who all ... Everyone agreed that actually it's your people management and the way that you make people feel-

    3. JHJordan Van Horn39:18

       Hmm.

    4. HSHarry Stebbings39:18

       ... 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?

    5. JHJordan Van Horn39:30

       (laughs) I'll send it to you after this. Um, it, it's, it's a public Notion doc actually.

    6. HSHarry Stebbings39:36

       Please do.

    7. JHJordan Van Horn39:37

       So, uh, 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, and why I do what I do. Um, and this isn't ... This is gonna 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?" Right? Um, and so what I've, what I've tried to t- take painstakingly detailed effort on is to clearly document, like, who I am, how I work, and what I do. So, like, one, I set really clear boundaries at work. Like, I do work a ton, but from 5:00 PM to 7:00 PM, you will never find me. I sit and I have dinner with my wife and my three daughters, right? And so ... And I tell them, like, "If you try to find me in those two hours, I will not show up. So just so you have an expectation, this is, this is me. You will never get ... Don't ever set a meeting for me from 5:00 to 7:00. I won't ... I, I won't e- decline it. I won't show up." Um, so it's like expectation-setting on how to interact with me. Um, "This is how long you can expect me to respond to something. Here's my phone number if you really need something." You're, you're getting out ahead of those, like, "Jordan isn't responsive," or, "He doesn't care about me," or, "He doesn't, like, um, you know, think that my problems are the biggest problems in the world." I'm giving them a framework for how to communicate with me. Um, that's the first thing. Uh, the second thing is I'm telling them what's important to me. Um, and so the user guide is there's, there's seven things on the user guide that are really critical to me. Um, they're criti- they- they're the things I care the most about, and they're the things that I reinforce every single day. So when everyone starts, I give them my user guide. I say, "Let me know if you have any questions." And s- for some folks, for direct reports, I'll actually walk through it with them. Um, and then I also put in, "Hey, these are the five things that are just most important to me in life." Right? Like, this is, like, how I make decisions in my life. This is who I ... This is, like, kind of core identity stuff of who I am. Um, and so, like, people ... What I found is, for most people, it, it basically, like, shortcuts the trust process. Like, especially when you're in an interview and you're trying ... Like, someone's like, "Well, hey, how do I know that, like, you're not gonna, like, ask me to fly to San Francisco in the middle of a pandemic and work till 9:00 for two weeks when I have a brand-new ... like, a newborn?" That's what people expect from startups, right? And I can say, "Let me show you my user guide that I put together not just to convince you to come work at our company, but this is, like, how I operate and what I care about." And so, um, it's been a good shortcut for me to, like, put that, like, have that identity of who I am and to give to people outside of the context of whenever that inevitable conflict is going to arise.

    8. HSHarry Stebbings42:07

       So that's how they interact and can expect to interact with you, which I love. Um,

18. 42:12 – 46:13

    How do you nurture and invest in talent?

    1. HSHarry Stebbings42:12

       in terms of, like, how you interact with them, I spoke to Eleanor on your team, and she said that you are the best at nurturing and investing in talent-

    2. JHJordan Van Horn42:20

       Hmm.

    3. HSHarry Stebbings42:20

       ... within your teams. Sounds super nice. Great.

    4. JHJordan Van Horn42:24

       (laughs)

    5. HSHarry Stebbings42:24

       But, like, what does it actually mean in practice? How does ... How do you nurture and invest in talent specifically? What works and what doesn't?

    6. JHJordan Van Horn42:32

       Yeah. Good question. Well, it starts in the hiring. Like, just, like ...Um, customer success starts in the sales process. Employee success starts in the interview process, right? And so deeply understanding what someone cares about and what their motivations are and making sure there's a motivational fit for why Monte Carlo makes sense for them, that's the why. We just don't hire people that, like, aren't gonna be happy. So, like, there's a bit of selection bias. I appreciate what Eleanor said, but there's, like, a little bit of selection bias that, like, I hire a very specific type of person that I know will be successful in our organization and, and will, you know, tolerate me as a manager. Um, but so, like, one, knowing what they care about. On their first day, I tell them all the reasons why I hired them and all the reasons they are going to fail. And so I, and I lay it out on day one. And the, as much as you can, like, take all that conflict and pull it out of the heat of a moment and set that, set them right on the first day, like, that just makes such a difference, um, right? And so I sit down with each person, "Here are the things that your superpowers, this is why you're gonna be my boss someday. Here are the things that are major derailers for you that came up in the interview process, and I want you to be aware of them and I'm gonna be watching them." Like, what does that do? That exposes someone's blind spots on their very first day. Um, and it can be, like, a little bit rattling, but it sets this tone of like, okay, we're gonna have a very direct and honest convers- like, relationship from day one. Um, and then I revisit those things every week, I revisit them. Um, now obviously, like, uh, Monte Carlo's been an interesting experience because we're growing so fast and it's hard to make time for those things. Um, and there's been seasons where I haven't been as good at that, uh, as I would like. But generally, that's what I, um, that's how I approach nurturing talent.

    7. HSHarry Stebbings44:09

       I love that, and I also love the, I mean, quite tough conversations from day one, which I think just engenders greater trust that, you know-

    8. JHJordan Van Horn44:16

       Mm-hmm.

    9. HSHarry Stebbings44:16

       ... I know where you doubt me and that's okay as long as I know it. What I don't wanna know is that Jordan doubts me and I'm not sure where or why. And that's-

    10. JHJordan Van Horn44:24

        Right.

    11. HSHarry Stebbings44:24

        ... where insecurity, I think, creeps in. So I, I, I love that.

    12. JHJordan Van Horn44:27

        Zhenya-

    13. HSHarry Stebbings44:27

        Okay, so-

    14. JHJordan Van Horn44:28

        M- my first one, well, I, I learned that from someone, from Zhenya. So my first one when I was with Zhenya, he said to me, he goes, "Jordan," (laughs) what was it? "You have a low hiring bar and you have bad judgment." And I was like-

    15. HSHarry Stebbings44:38

        (laughs)

    16. JHJordan Van Horn44:39

        ... "Oh my gosh, I'm getting fired and I'm five days in." And he's like, "This is not a problem. We will, we will fix it." (laughs) I was like, "Oh my god." And that was, like, the most powerful, like, that got me to change, like, really quickly and it helped me focus. It, like, um, it, like, changed my trajectory at Segment for sure.

    17. HSHarry Stebbings44:54

        No, actually, Zhenya... (laughs) I don't know if I'm allowed to say this, but fuck it. Uh-

    18. JHJordan Van Horn44:59

        (laughs)

    19. HSHarry Stebbings44:59

        ... Zhenya told me that you, Zhenya told me that your weakness is you actually care too much about your team members, in particular, AEs, reps.

    20. JHJordan Van Horn45:07

        Yeah.

    21. HSHarry Stebbings45:07

        And the challenge that you now have is, as a sales leader, you have to slightly extrapolate yourself out of that and you're not middle management anymore-

    22. JHJordan Van Horn45:14

        He's right, yeah.

    23. HSHarry Stebbings45:14

        ... where you can have that, and you have to detach yourself and be a lot more objective. Do you think that's fair?

    24. JHJordan Van Horn45:20

        That's very fair. That's very fair. Yeah. I'm working on it. Uh-

    25. HSHarry Stebbings45:25

        (laughs) Yep, that's true. Yep, yep. Okay, so-

    26. JHJordan Van Horn45:27

        I think, uh, yeah, I think, um, the comment that I'd make i- in reaction to that is I used to think that people just wanted to be supported and they, like, knew exactly what they needed to be supported and they just need, like, a cheerleader, right? And I think that's, like, the version of me that worked for Zhenya, um, that he kinda, like, beat out of me over three years. Uh, what I've learned is people need, like, a really clear understanding of what great looks like and they need to be told how they're progressing towards great. And I think that's how you, um, you walk that path of, like, deeply caring for people, but being able to be objective and doing what's best for them. And so, like, um, you know, learning that hard lesson I think everyone learns, which is, like, caring is, does not mean nice. They're not the same thing. You can be, like, very uncaring and very nice, right? And so, um, so that's been the, the fun

19. 46:13 – 49:08

    The Ideal Onboarding Process for New Sales Hires

    1. JHJordan Van Horn46:13

       one to learn for sure.

    2. HSHarry Stebbings46:14

       I, I totally agree with you there. I, I, I do want to touch on the onboarding process 'cause it's a very difficult one where most people fuck up. Um, what, h- h- okay, I come in first day. What does an ideal onboarding process look like for you with new sales hires and how should we stage it?

    3. JHJordan Van Horn46:33

       Well, you know, I mean, in the early days, um... I, I always think that onboarding should reflect the stage and maturity of your company. So, like, I don't want, 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 30-day onboarding season then you're gonna move out and, like, everything's gonna be hunky dory. Like, no, you're walking into, like, a disaster and you're gonna continue to be in a disaster, right? And so you gotta figure it out. So, like, early days, um, the onboarding was, "Hey, here's the information that you need. Go figure it out. I ain't got time," right? "And then I'm gonna give you a ton of feedback. I'm gonna shout at you. I'm gonna put time into you, but there's nothing structured," right? Um, th- that works with, like, your first couple sales hires and it n- it needs to work with your first couple of sales hires, right? Um, because, like, that's the reality of the company. Um, later on as you're trying to go onboard, like what we're in right now, we're trying to on- onboard and hire, you know, people in the, the orders of magnitude of 10s and 20s, um, you have to get really, really disciplined and structured. "Okay, what are the things that you need to know? When do you k- need to know them by and how do we demonstrate that you've actually known them?" And so, um, you know, we've put together a very rigorous onboarding program, um, that checks off those competencies. "And what are the levels associated with those competencies and how do we know that that person's achieved those levels?" Um, and the ma- I, I put onboarding at this phase into the hands of those frontline sales managers, um, because it's their job to onboard and enable their people. Someday when we have a thousand reps, there will be a field enablement or a field productivity function that will own that. But in the early days, it's your managers, right? And I think that's true for every function for what it's worth. And so, um, you know, it's incumbent on the manager to go spend, you know, a third of their time with new hires, um, in the first month. Um, and it, it, it j-

    4. HSHarry Stebbings48:12

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

    5. JHJordan Van Horn48:18

       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, what is the, "Hey, there's, like, a 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

20. 49:08 – 50:25

    Most Common Red Flags that a New Sales Hire Won’t Work Out

    1. JHJordan Van Horn49:08

       30 days about whether someone's gonna be a fit or not.

    2. HSHarry Stebbings49:12

       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?

    3. JHJordan Van Horn49:21

       Impact. Impact. It's all about im- 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 a, 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, 5X pipeline coverage," um, or all of these, like, very soft things that, like, TBD about whether they're, like, high i- 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 need to have an impact immediately. And I think that you, you could 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.

    4. HSHarry Stebbings50:22

       I get you. The challenge I have here is... and this is relevant

21. 50:25 – 53:07

    How do you determine quality of Sales Reps?

    1. HSHarry Stebbings50:25

       for you with, you know, the go-to-market with, uh, 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?

    2. JHJordan Van Horn50:47

       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 gonna 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, th- the better you can build out your sales process and your gas sales playbook, um, to have discreet, measurable events, you can get signal on day one of a sales cycle. That deal may or may not... 10% likelihood or 5% 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.

    3. HSHarry Stebbings51:39

       Hmm.

    4. JHJordan Van Horn51:41

       You want me to give you, like, a tangible example or is that too fluffy?

    5. HSHarry Stebbings51:44

       Give me a tangible example.

    6. JHJordan Van Horn51:46

       Okay. So, um, all right. Person XYZ, um, enterprise rep, uh, they get throu- they, they have two weeks where they learn the product and they go through, um, pitch presentation, right? This is a person with 10 years of experience. So, they go to that pitch, pitch presentation and they just, like, flop horribly, right? Like, there's a very clear indicator that something's not going right in the onboarding with a person at that level of experience, and you have to understand what's going on there. So, that's your first red flag. I wouldn't fire someone 'cause they missed a, uh... like, didn't do well on a presentation. But then, so they pass the pitch presentation, maybe they do really well, and then maybe in the... the... you release them into the wild and they go set up three or four calls. Good. Um, if all three or four of those calls don't have next steps set with them, um, or don't go anywhere, um, or don't have that person, you know, um, you know, talking to other people in the organization asking for introductions, uh, nothing comes out of them, y- you have a potential red flag on your hand, right? 'Cause what that, what that person's gonna say is like, "Hey, it takes a while to build pipeline." But, like, again, ain't nobody got time for that. Like, you know, for our company, we're two years old. Like, uh, you can't, you can't ask me to worry about Q1 of next year next year. Like, that is not guaranteed. It is not guaranteed that we're gonna survive for that long, right? Um, so, like, what are the things you're doing right now to actually progress the company? And if that person has nothing, nothing to show for those first

22. 53:07 – 54:20

    How soon do you let new Sales Reps meet customers?

    1. JHJordan Van Horn53:07

       calls, then there's, there's something not right there.

    2. HSHarry Stebbings53:11

       How soon do you let reps meet customers?

    3. JHJordan Van Horn53:16

       Um, we've been doing it too soon lately. So, like, our entire team has been ramping, like, our entire (laughs) team's, like, ramped because we've gone from, like, zero to 80 people, uh, in a year and a half, right? And so, like, I think just, like, uh, so we had just, actually needed people on the, on the phones, like, in week, week one, uh, and it's been too soon. Um, so I think though, the right thing is, I think people should, um, meet a few customers in their first month on the job under close supervision from a buddy or a manager, and I think th- that's more for their learning. And you have to expect that customer is not gonna turn in the c- to... or that prospect is not gonna turn into a customer, right? You just have to, like, accept that that's a potential outcome. It's more about that person's growth and development. Um, so I need them to be in front of customers pretty early on, but in terms of when they're running a deal cycle, I think you need to wait, like... We've been doing it 14 days in. I think the right answer's probably, like, 30 to 60, um, and we're trying to figure out how to, how to make it faster, but, um, but I think it's starting to hurt us a little bit.

    4. HSHarry Stebbings54:15

       You mentioned churn customers there. The final thing I do just wanna touch on before we go into a quick fire,

23. 54:20 – 56:34

    How to Structure a Deal Review

    1. HSHarry Stebbings54:20

       uh, postmortems. Uh, we hear about them a lot on kind of deal reviews. How do you think about structuring deal reviews? How often do you do them? Who sets the agenda? How do you think about making a really good deal review?

    2. JHJordan Van Horn54:32

       Yeah, we postmortem everything, so, uh, deals, POCs, uh, top of funnel. Like, everything gets postmortemed, because the only thing that matters early on in your company's life is, is how quickly you learn. Right? I told you revenue doesn't matter. What matters, how quickly you learn and how quickly you put it into action. So, um, so we do deal reviews. We do forward-looking deal reviews once a week, where we take our key deals and we actually go really, really deep on them. Uh, but we do retro- we do retrospectives on every single deal, um, where we invested significant resources and we didn't get a- an outcome. Right? And so typically that's when something gets to POC, um, and if for some reason that POC doesn't convert to a paid customer or it takes too long, we'll do a postmortem. I do postmortems on deals that we've won that I don't think we did a very good job on. Like, um, you know, I think what you're looking for is you're looking for cracks in the sales foundation, um, and you're trying to extract all of the learnings from those. Um, and so I would say as many as possible. And I love if the rep can lead it, because making a safe space for them to lead with their failures and to own it creates such a great environment for learning, right? And so you just can't let those things turn into, "I'm gonna beat you over the head because you made these five mistakes."

    3. HSHarry Stebbings55:40

       How do you create the safe space? Tough to do.

    4. JHJordan Van Horn55:44

       Well, when you screw up as much as me, you have a lot of opportunities to demonstrate it. And so, you know, I- I- I try to be really open about my failures because... And a lot of the mistakes that these reps are making are, are mistakes that I made when I was trying to figure out the sales motion, right? Um, like a- like two years ago. So, um, so like I get it. And so I- I think one is I- I try to communicate to people that, like, sharing your failures and your mistakes is a sign of strength and not a sign of weakness. And I actually don't trust you if you're perfect. And so I say that like maybe on a monthly basis, right? Um, and so like people know if they have nothing to work on that like I'm kinda giving them the side eye because I'm a little suspicious about like what they're actually doing.

    5. HSHarry Stebbings56:22

       I love that, "I don't trust you if you're perfect."

    6. JHJordan Van Horn56:25

       (laughs)

    7. HSHarry Stebbings56:25

       You would n- You- you- you would trust me implicitly then.

    8. JHJordan Van Horn56:28

       (laughs)

    9. HSHarry Stebbings56:29

       That's what makes sense. Uh, but listen, Drew. I love doing this. I wanna move into

24. 56:34 – 57:41

    Which sales tactics haven’t changed the past 5 years?

    1. HSHarry Stebbings56:34

       a quick fire round. So I-

    2. JHJordan Van Horn56:35

       Go for it.

    3. HSHarry Stebbings56:35

       ... said a short statement. Okay. So let's do, what sales tactics have not changed over the last five years?

    4. JHJordan Van Horn56:41

       Hm. Discovering qualification. I can go deeper if you want me to.

    5. HSHarry Stebbings56:47

       'Kay. All right.

    6. JHJordan Van Horn56:47

       Um, look, at the end of the day-

    7. HSHarry Stebbings56:49

       Okay.

    8. JHJordan Van Horn56:50

       ... understanding your customer will always be the most important component of sales. If you don't understand your customer or what problem you're trying to solve, you shouldn't sell them anything. Just bar none. Don't do it. It's not how you build a company. Two, qualification. I- if you can get sales to a point where it's actually like an engine, where you're thinking about where I spend my time is the most important and most valuable thing, uh, and where I focus, like actually knowing who's gonna buy and who's not gonna buy early on and s- putting all of your chips and resources towards the ones that are gonna buy is really critical. And so what sellers can do is they can really take your company for a ride if they're like, "Trust me, this- this person just lo- Like, this person's gonna do a deal. Like, I just know it. Like, I know it. Like, they've never bought software before, but like they just have this pain that's so big, so let's go like build this integration that's gonna take us like two engineering sprints." Right? Like, that happens all the time. And so discipline around qualification is I think something that, um, that has actually like ramped

25. 57:41 – 58:23

    Which sales tactics have died in the past 5 years?

    1. JHJordan Van Horn57:41

       up probably in the last 15 years, um, and I think will stay for a long time.

    2. HSHarry Stebbings57:45

       What sales tactics have died a death over the last five years?

    3. JHJordan Van Horn57:49

       Hmm. Pure tops-down, pure tops-down sale. Uh, I- I will never be able to go into a- a CIO's office and show them a really spiffy deck and give them a customer reference, um, and get a deal. Right? Like, CIOs, CTOs, VPs of engineering, they need to see that their teams are using and adopting the product because they're r- actually realizing that getting humans to change behavior is as hard as evaluating software. And so that- that CIO making a unilateral decision, they c- they obviously are really important to the deal cycle. Like,

26. 58:23 – 1:00:30

    What advice would you give to a Sales Leader starting today?

    1. JHJordan Van Horn58:23

       they're critical. Um, but they're not the only piece. You have to make practitioners happy at the bottom.

    2. HSHarry Stebbings58:27

       What one piece of advice would you give to a sales or a revenue leader starting a new role today?

    3. JHJordan Van Horn58:34

       Uh, it's all about your founder. Um, you're picking a partner, right? You're picking a partner ideally for the next four to six years. And so, um, how do you work together? How do you give feedback? How do your strengths and weaknesses complement each other? Having that open, uh, dialogue really early on i- is critical. Um, and, you know, just a personal example, I... Y- there's p- like four pillars of great sales leadership. Uh, the one that I really suck at... Like, I'm not a product marketer. I don't tell a story. I don't create a neat analogy. Like, I can't like help anyone understand what this thing is. Like, I'm a systems and I'm a process and I'm a people and I'm an execution person, right? Um, so I needed Bar, who like created this entire category and who understood how to tell, like, an entire story of the problem that we're trying to solve. I needed someone who was an A++ in that because I'm like a D-. Right? And so I think that like... A- and setting that expectation with her of like, "Hey, this is what I am and if you're not ex- if you're expecting this out of me, don't, 'cause I am not good at it and I'm not gonna get good at it." Um, I think that's like a really important early conversation between a founder and a sales leader because, um, even just... The reason you're doing this podcast is because I think founders don't necessarily know what to expect out of sales leaders. They don't know what they're supposed to be doing, right? And so they-

    4. HSHarry Stebbings59:41

       They-

    5. JHJordan Van Horn59:42

       ... they fill that void with assumptions.

    6. HSHarry Stebbings59:45

       They don't, and then also bluntly, they don't know what truly great looks like, you know?

    7. JHJordan Van Horn59:49

       Right.

    8. HSHarry Stebbings59:49

       I- I find it very interesting when I meet amazing companies and then I meet the sales leaders and I'm like, "What? What is going on?"

    9. JHJordan Van Horn59:57

       Right. Right.

    10. HSHarry Stebbings59:57

        And, and it's because they don't know. Because like, you know, the- the canonical advice is interview 10 of the best in the world and then-

    11. JHJordan Van Horn1:00:03

        Mm-hmm.

    12. HSHarry Stebbings1:00:03

        ... find what truly great looks like. Well, are you gonna respond to random founder in Bumfuck, Nowhere who wants to pick your brains for half an hour just so they can hire someone half as... like half a percent-

    13. JHJordan Van Horn1:00:15

        Right.

    14. HSHarry Stebbings1:00:15

        ... as good as you in Bumfuck, Nowhere?

    15. JHJordan Van Horn1:00:17

        Right.

    16. HSHarry Stebbings1:00:17

        No.

    17. JHJordan Van Horn1:00:18

        (laughs)

    18. HSHarry Stebbings1:00:18

        And so this... Yeah. I'm passionate about this.

    19. JHJordan Van Horn1:00:20

        That's not, that's not-

    20. HSHarry Stebbings1:00:21

        Um-

    21. JHJordan Van Horn1:00:21

        ... a shot at Merced, California, is it?

    22. HSHarry Stebbings1:00:24

        Bumfuck, Nowhere. No. (laughs)

    23. JHJordan Van Horn1:00:27

        (laughs)

    24. HSHarry Stebbings1:00:28

        Man, I am in the middle of London,

27. 1:00:30 – 1:00:58

    What would you most like to change about Sales?

    1. HSHarry Stebbings1:00:30

       the metropolis of the world, so I, um, I- I have a high horse here. Uh, what would you-

    2. JHJordan Van Horn1:00:34

       Great.

    3. HSHarry Stebbings1:00:34

       ... most like to change about the world of sales?

    4. JHJordan Van Horn1:00:37

       Uh, I'd like to see custom- customer-oriented sales win out. Um, I think that there's too much distrust between sellers and buyers, um, and I... but I think the best sellers and the best companies in the world are always trying to drive business impact for their customers. Um, and I think, um... and they just care a ton about their customers, uh, who put their names and their reputation on the line in buying this software. Like, those are the companies

28. 1:00:58 – 1:01:24

    Hardest Thing about Jordan’s Role at Monto Carlo

    1. JHJordan Van Horn1:00:58

       that matter. You know, Snowflake's a great example of this, right?

    2. HSHarry Stebbings1:01:02

       What is the hardest thing about your role with Monte Carlo today?

    3. JHJordan Van Horn1:01:06

       Oh. Uh, I mean, growing from, like, no revenue to, like, eight figures in revenue in 18 months is really freaking hard. Uh, growing a team from zero to 80 is really hard. And so, um, maintaining simplicity and focus when an organization is becoming much more complex

29. 1:01:24 – 1:02:30

    First Thing to Break When Scaling

    1. JHJordan Van Horn1:01:24

       is a huge challenge. Um, and it's something that I wake up and think about every day.

    2. HSHarry Stebbings1:01:28

       What's the first thing to break in such scaling?

    3. JHJordan Van Horn1:01:33

       Hmm. Communication is the obvious one, right? And that's a company problem. I think, like, uh, 150 people is, like, a great number where just, like, everything breaks down, right, from a communication standpoint. Um, I think the second thing that, that breaks down, e- especially if you're growing really fast, if you have more new people than, uh, than, like, core nucleus, like, which is the situation that we're in at Monte Carlo right now... Like, if you were to have a pure democr- de- democracy, the people with, like, three to six months of tenure would actually win the vote, right? And so, like, the first thing to break is, like, what works and what has worked historically, and how do you empower and engage that nucleus to, like, basically overpower the new people to help them understand why we do the things that we do? That's a really, that's a really hard challenge that, um, that I think... also think about every day.

    4. HSHarry Stebbings1:02:19

       That's why I always run dictatorships in my companies (laughs) .

    5. JHJordan Van Horn1:02:22

       Right. Exactly. (laughs)

    6. HSHarry Stebbings1:02:24

       So d- d- yeah, democracy in my companies is not a thing. Um, fi-

    7. JHJordan Van Horn1:02:29

       Democracy's not going

30. 1:02:30 – 1:03:46

    Which company’s sales strategy have you been most impressed by?

    1. JHJordan Van Horn1:02:30

       well right now. Let's be real. (laughs)

    2. HSHarry Stebbings1:02:33

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

    3. JHJordan Van Horn1:02:40

       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. Uh, 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've, 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, 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, are really great companies to look at.

    4. HSHarry Stebbings1:03:24

       Jordan, I, I cannot thank you enough for this. The best shows for me are when there's actually a clear structure and breakdown to answers, like the three things, like the structure that you provided today. Honestly, man, uh, it's shows like this that make me so happy to do what I do. So thank you so much for joining me, and I love doing this.

    5. JHJordan Van Horn1:03:41

       Thanks, Harry. It's been a pleasure, man. I really enjoyed it. And thanks for wearing the cowboy hat for me. Means a lot.

Episode duration: 1:03:46