← The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency
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- [00:00]
A
This is 20 sales with me, Harry Stebbings. Now 20 sales is the monthly show where we sit down with the best sales leaders to unpack how they hire, train and retain the best sales teams. Joining me is a legend, John McMahon, widely regarded as one of the greatest enterprise software sales leaders of all time. He's the only person to have served as Chief Revenue Officer at five public software companies today. He sits on the board of companies such as Snowflake and MongoDB and also mentors and influences a who's who of mo modern SaaS sales leaders. This was one of my favorites to do in a long time. He's just the sage of our business and has taught so many of the great sales leaders today. But before we dive into the show today, is your finance team a cost center tied up in enforcing policies, bogged down by cumbersome processes and drowning in operational busy work? Well, what if you could unlock seamless strategic finance that actually fuels your business growth? This is why leading global growth companies use payhawk, the finance orchestration platform that unifies, simplifies global spend management with conversational AI to deliver best user experience for everybody dealing with company spending, finance teams using payhawk report a major shift from operational to strategic work. New AI agents for each finance role handle the busy work, acting with the same governance as your finance team. Like having a small team of expert assistants that work 24 7, but also providing an exceptional user experience to your employees. Payhawk is built for growth and enterprise businesses that operate globally. No six month implementations, no consultant dependencies, just immediate finance transformation that scales with your business. Leading growth companies like Vinted, Wallbox and Hundreds more across 32 countries use Payhawk to move finance forward, not just keep up ready to turn your finance processes into a competitive advantage. Payhawk is offering a staggering 30% discount to everybody switching from a qualifying expense management or company card provider. Who mentioned the 20 VC podc.
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To.
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A
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C
To to win deals.
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C
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Help your teams get great work done with miro. Check out miro.com to find out how. That's miro.m I r o dot com.
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C
You have now arrived at your destination. John, I am so excited to have you on the show because all of the greatest shows that I have done with sales leaders, they were all your proteges to some extent, and they all cited you like explicitly in the shows as being the reason why they are the sales leaders. They are.
- [03:52]
B
That's nice, which is amazing.
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C
So thank you so much for joining me.
- [03:55]
B
You're welcome. Harry, good to see you. Glad you got dressed up for me.
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C
Thank you.
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A
I'm glad that you appreciate my short shorts. If you also knew the temperature outside.
- [04:04]
C
It'S like freezing in London. My question to you is you have now been a sales leader for. For what, 30 years? 35 years?
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B
Well, I'm not a sales leader now, but I was for about 30 years. Yeah.
- [04:15]
C
So tell me, how has the art of sales changed?
- [04:20]
B
I don't think that the art of the sale has really changed much because there's an art to it and then there's a science to it. So the art hasn't really changed because you're dealing with people and that can be, you know, depending upon your style and whether or not you can have like a rubber band effect to reach out to different types of people because you're going to run into analytical people, you're going to run into draw drivers, you're going to run into expressives, you're going to run into amiable people and sure ability to. To deal with people. That's the art part of it. I think what's probably changed a lot and it's become a lot more formal is the discipline around the sales process that I think has changed, become a lot more regimented. People have really figured out, you know, what is the sales process for my product and what's the right messaging and then even on top of that, what's the right ideal customer profile that I should go after.
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C
Do you think that regimented sales playbook structure holds true in a very new world of AI and revenue scaling that we're seeing today?
- [05:20]
B
It should. Why it should still hold true. No different than, like I think about a sports team. Sports team has a playbook and the players have to know the playbook, so they have to have the knowledge, and then they have to have the skill set to execute the play. And a sales process is no different. I can train you on the knowledge, but you still have to have the same discipline around the skill set to be able to execute the play. And when you execute the play, you might execute the play because you have the same skill that I do. But there's the art part that the way in which you execute that play might be a little bit different than the way in which I execute that play. But we both have the same skill set.
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C
But if we look at the domination of PLG products that are now pervading their way into enterprise like a cursor or like an OpenAI and ChatGPT, which obviously have enterprise editions, does that not fundamentally change the way that we sell and the playbook to sell?
- [06:17]
B
What does change? So if you really think about the essence of the license agreement in software, it used to be a perpetual license. So I sold you some software, you signed a license agreement, you own the software. So if you're complaining to me about the software not working, I have a pretty long time to come back and try to fix it. Not that I don't want to do customer support, but I can also run someplace else and buy myself some time before I fix your problem. Then we move to subscription software. And now we were on annual subscriptions, so now I basically have like six to nine months. If you're not getting value out of my software to go ahead and fix your problem, make sure that you get value out of it. Otherwise you're not going to renew and you're going to churn. Okay, now we've moved to not so much the PLG world, but really to consumption software. So now basically I might have a week. You might turn it on with plg. You might turn it on because I gave you the, the ability to download it and you start to consume. And now maybe a week later you decide that you're not getting value out of it and you churn on me. So I have to pay so much more attention to value realization for you than I ever did, you know, 25 years ago.
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C
And surely that if it is consumption based in that way, where the initial ACV is so much smaller. Because of that I am not able to invest in the outbound reps, in the sales teams and infrastructure. Given that my reward is this smaller ACV consumption based ticket. So it does change the whole sales. Org.
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B
No, it does change it because you're probably going to get originally going to get much smaller deal sizes and then you have to count on going back and getting the renewal and a much bigger upsell.
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C
Yeah.
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B
And that's why net dollar retention has become such a critical factor when people are looking at companies. Okay, you are booking deals, you're getting a lot of new logos, but what's your net dollar retention?
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C
I spoke to Dev at MongoDB.
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B
Dev. Well, I just spoke to him like two days ago.
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C
He said that you are world class when it comes to separating signal from noise and focusing on the right problem to solve. He said, I want you to really start on that. Harry, what is your approach to separating noise and signal and that focus? How do you do qualifying?
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B
Qualifying a deal? Usually you know, I use and start with a framework that you've probably heard of like medic or med pick and then I'll start to go there. And what you're really doing is you're thinking about where is the person in the sales process. So they think about like Google Maps as your sales process. So if I'm going to drive from Boston to New York and I go to Google Maps, it tells me the turn by turn directions. No different than a sales process. That tells you here's the different steps you have to take in each stage of the sales processes in order to get an order in the shortest distance of time. And now you know you're driving for an hour and then you think, hey, I'm 20 miles before Hartford, Connecticut and you pull off for some gas. And now you're like, how do I get back on the highway? And now you use your GPS to tell you where you are. And GPS says, Harry, you're already 10 miles past Hartford, Connecticut and here's how to get back on the highway. So the way that I think about it is you stand up to tell me about a deal. The first thing I'm thinking about is where does Harry think he is? Harry thinks he's 20 miles before Hartford. I'm going to qualify you to figure out, hey, Harry really is 10 miles past Hartford, Connecticut. And the way I'm going to do that is start to ask you a bunch of qualifying questions to figure out precisely where you are. So let's say you have A five step sales process or stages in the sales process. And you have different steps in that sales process. I'm going to figure out exactly what step you're at in what stage. So now I can coach you, I can tell, Harry, Harry, here's where you think you are, but let me tell you where you really are and what you need to do next and what information you have that tells me where you are and what information you don't have that you have to get in order to move the sales process forward.
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C
What single question is most revealing in where someone actually is not where they think they are in that?
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B
There's a lot of revealing questions, but one of the most powerful ones is someone's standing up there and saying they're going to get a half a million dollar deal this quarter. And you say, well, that's interesting. Do you have a champion? Yes, I have a champion. Okay, and how long have you been calling on this account? Six months. Have you met the economic buyer? No, I have not met the economic buyer. You don't have a champion and you're not getting the deal. Because if you really truly have been in that account for six months and you truly had a champion and you think you're going to get a half a million dollar deal, you already probably met the economic buyer. That one's so revealing.
- [11:04]
C
You said you're not going to get the deal there. When have you not got a deal that most sticks to your memory? When I say a lost deal, which one first comes to mind and what do you take away from that loss?
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B
Well, when I was selling myself, I just used to beat myself up about what did I do wrong? You know, what did I do wrong in the sales process. And typically when people lose a deal, they skipped a step in the sales process process. And typically when you diagnose why they didn't get the deal and you go back through everything that they did, they skip the step.
- [11:41]
C
And that step is I didn't have a champion, I didn't do qualifying correctly.
- [11:45]
B
I didn't, I didn't really under that step could be. I didn't understand their process. So if somebody has a business problem, think about the fact that that probably is created these days by a technical problem. And a technical problem typically has a process that they go through to enable something or do something. So I didn't understand all the different steps in that process. And for those different steps, I didn't understand the pains that they have in that process. And I didn't understand and quantify the pains in that process and how my differentiators might align to the pains in that process. So I can get my differentiators and my capabilities for my product that are different than the competitions in the decision criteria so that the customer tests to my differentiators and therefore I win. Because whoever locks down the decision criteria is going to lock down the deal.
- [12:40]
C
What do you mean, locking down the decision criteria? Sorry?
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B
When you lock down the decision criteria. So first you might think about the process again, the pains in the process, the quantification of the pains, who's involved for each different step in the process, the technical process, plus the decision process itself. And what you're trying to do is find a champion that can help you lock down the criteria. The worst thing that you want to have happening in a sales process is you show up and things are moving around on you. I talked to Harry and he says, yeah, John, we're thinking about these three or four things are in the decision process that we're going to test. I come back the next week and things have changed. Then I come back the next week and things have changed. I'm constantly getting surprised I'm not in control. My sales process is very unpredictable. All of a sudden, I make Harry a champion. He buys into the fact that my product can solve the problem better than anyone else's product. Now Harry starts to take control of and understand why I need these differentiators in the decision criteria because it solves Harry's pain. And now Harry starts to say to the organization, because he has influence. That's why he's a champion. We're going to lock down this criteria and here's what it's going to have in it. Now my sale moves from unpredictable and surprises every time I walk in to very predictable because Harry's now helped me take control. Because when you think about a sales process, who are the three people that could be in control? One, the customer. In the beginning, I need information from the customer, so the customer is in control. Eventually, the customer buys into the fact that they have a problem and they want to buy software. Now they need information from one of the salespeople. So either I'm going to get control or my competition is going to get control. So when I'm walking into sales meetings and people are still surprising me, I don't have a champion. I'm not in control. Maybe my competition's in control because every time I show up, something new is getting inserted into the decision criteria. The people I'm talking to didn't do it. So that Means the competition is doing it. I'm not in control and I need a champion to help me lock down that criteria.
- [14:54]
C
You said about pain there. One of the biggest pains that I see enterprise sales leaders have is urgency.
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A
It's the, how do I get it done?
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C
How do I get it over the line? When you think about biggest lessons on how to instill a sense of urgency in a conversation as part of that process, what works and what doesn't and how do you advise those sales leaders.
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B
Listening to drive urgency? What a lot of people are really good at is they're really the greatest sales reps even are great at finding the pain, quantifying the pain, inserting their, you know, differentiators in the decision criteria. But they never ask, hey, Harry, when you have these pains, if you don't do anything, you don't try to solve these pains, who suffers and what suffers? And then Harry says, well, I would suffer because my job measure is tied to these pains. And if I leave it the way that it is, I'm going to suffer in my job measure. I'm also getting website outages all the time, so that suffers and maybe we don't get the, the company doesn't get the revenue that they need to get. When you ask those questions of who suffers and what suffers and there's different ways of asking if that's essentially what you ask, I've now have implicated the pain. So now when I call Harry back next week, he says, oh, John. Oh, it's, Yeah, I, it's good to talk to you, but look, I'm really busy, I don't have any time. Well, Harry, hold on a second. Last time we spoke, you told me that if you don't solve the pain, here's what happens to your job measure and here's what suffers in the company. Harry all of a sudden says to me, I got five minutes, what do you got? Next thing you know, I got, he's got 30 minutes. So if you don't implicate pain, you can't drive urgency, you can't make it up, you can't create it. It has to come from the customer telling you that.
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C
Will you discount to drive urgency?
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B
No. You might discount at 1159 in the quarter to get a deal across the line, but it's a deal you're going to get anyway. It's a matter of whether or not you really need it in the quarter or don't need it in the quarter.
- [16:57]
C
When have you had an inferior product to your customer and how do you manage Your sales process, when you know you have a worse product, you manage.
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B
It the same way. You have to lock down that decision criteria. If you don't do that, you're not going to win. And you can only lock it down with a champion.
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C
What happens when there's multiple champions?
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B
Then you're even more powerful.
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C
Why?
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B
Sometimes one thing you want to ask yourself in a sales process is, is my champion stronger than the competition's champion? Because at some point there's going to be a meeting, you won't be there. And you might have a champion, they might want you to win, they might have a personal win. That personal win could be approval, recognition, control, promotion. But is the competition's champion stronger? That's the question. And you have to ask yourself that. Now if you ask yourself that and you think, well, Joe is stronger than Harry and Harry's my champion, I have to go out and find another couple champions or at least another champion to help Harry plow through Joe when I'm not there. And I have to prep Harry for that meeting.
- [18:05]
C
How do you do that? How do you actively prep Harry for that meeting? Because they won't always tell you, hey, there's a meeting coming up where X or Y is happening. How do you prep them so that they are weaponized for that internal conversation?
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B
Well, really good sales reps do this for a living. So they kind of know what's happening next. And a lot of times you can predict the future. You can predict that. Here's Joe's. Joe's the enemy. And you're going into a meeting. I know it's going to happen in the next couple days or so. And here's the questions that Joe's going to ask you. Are you prepared to answer these questions? A lot of times they'll just say, yeah, John, you know, I'm ready for the meeting. Are you sure you're ready? Because let me just ask you one question. And you ask them one question that stops them in their tracks. Or the same when they say, I'm just going to go talk to the economic buyer about this, but they're not prepared you. They don't really understand all the pains yet. You haven't quantified the pains. You haven't quantified the as is process to the to be process and understand what value you're going to derive by them changing to your product and changing the process. And then if you go to the economic buyer without those answers, you're going to get shot down. And then I lose a champion. So sometimes it's a matter of one, predicting the future and two, making sure that you're preparing your champion for what's, what's to come.
- [19:21]
C
Predicting the future and preparing your champion both take time. And Degnan, who I know is obviously one of your proteges and a friend, always says that really you can only have like six to seven really good meetings a week if you want to be prepped and ready for them.
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A
Do you agree with that?
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C
And how do you find the best sales reps and operators spend their time most effectively.
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B
The best reps spend their time most effectively preparing for the meeting with the customer. So most of them understand, you know, what the use case is. So they understand the process because they've sold the software a number of times, right? It's not like they're selling it brand new. The really good people have been around a year or two years, have sold many deals, multimillion dollar deals. It's almost like now they're great lawyers that are leading the witness. And what I mean by that is they already understand that the customer has these pains in their process. So now they're starting to ask Harry leading questions. Harry, have you ever experienced anything like this before? And Harry says, yes, I definitely have that pain. And now they can say, that's interesting because we've helped ABC Company resolve that pain. In fact, ABC company also had this other pain in their process. Have you ever experienced anything like that? Right. But they know it so well that they're not asking a question that they almost don't know the answer to.
- [20:48]
C
Do you need vertical sales teams sooner than you think when you look at that pain, acknowledgement, knowledge, very specific knowledge there that you will get that much faster if you have verticalized sales teams. Do we need vertical sales teams with domain specific knowledge much sooner than we think?
- [21:06]
B
I think it depends upon your ICP or ideal customer profile and how fast you're expanding your salesforce. So you have to as a CRO, constantly look into the future of saying, okay, you know, I have 50 reps now, I'm going to have 100 next year. And you have to think about what is my organization look like, where am I going to put 50 more sales reps in the country or maybe go to Europe, go to Asia, okay, now I'm starting to stuff them in the United States too fast. Maybe now I need to verticalize or is there another vertical that I can go into where I don't need to verticalize yet? Right.
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C
When you're bringing people to a team that you said they're about CRO going from 50 to 101 that always strikes me is would you rather have someone with experience in a domain or would you rather have someone with experience selling a ticket size that you are selling?
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B
I would much rather have the athlete over the domain person every time. In fact, at PTC we sold mechanical computer aided design software and we did not want anyone that had sold mechanical computer aided design software before. And ever since then, I've always hired people that did not understand almost anything about the domain. I want the athlete, so I want somebody that's super intelligent, super driven. I say that they have a PhD, persistence, heart and desire. And the reason those two things are important I'll get to the other things are one, if someone's really smart, they're going to pick up the knowledge of your playbook and the customer and the problem and the competition and the market. And if they have a PhD, persistence, heart and desire, then they're going to have the desire and the persistence to pick up the skills to execute the play, which really takes a lot of time. If I want to be a great dart thrower, I'm going to have to commit to throwing the dart a thousand times a day. If I want to be a great salesperson, I'm going to have to commit to certain skills that you that aren't going to come naturally to me and I'm going to have to do that after that. I'm looking for people that are very coachable. So do you want to be coached? But more importantly, can you adapt? Are you adaptable? Because a lot of people will get coached but they won't truly adapt or as time moves on in your startup, you'll see people that are really good. When you were let's say 3 million, 20 million, 50 million and then all of a sudden they hit a wall. And that's because the product changed, the market changed, competition changed, the messaging change, who you call ons change. You might have to go higher up the ladder and those people have an adapt, they're coachable. They say yeah John, yeah, that sounds good. Yeah, let's go talk about that. But they don't adapt, they don't actually change. And what you have to change is the skill set. They might have the knowledge, but they can, they don't, they don't want to develop the skills.
- [23:50]
C
If we just unpack that you said there can it skills that are required but not natural. What are the not natural skills that are required to be successful?
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B
Do you think the biggest one listening. Most sales reps are Horrible, horrible listeners.
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C
How do you train someone to listen?
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B
I always say that you need to listen with the intent to understand, not the intent to reply.
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C
What's the difference?
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B
Because then I'll probably ask you another question. I won't actually sit there thinking about what I have to. What I want to tell Harry. What I'll do is I'll sit there and understand what is Harry really saying to me. Have I asked enough questions? The second, the third, the fourth, the fifth, the sixth question to get down to the bottom of what Harry's asking me before I'm going to start talking about my product and what my company does and all that bullshit. John Kaplan always says that the customer doesn't care how much you know until they know how much you care. And you can't care if you're talking all the time. You can only care if you're listening and you're questioning and you're understanding. And there's a big difference between those.
- [24:58]
C
When we look at the other element, which you said there was coachable and adaptable, and people are sometimes coachable, but rarely adaptable. Those that want to be who are listening to this as sales reps or leaders, what would you say to them in terms of how they can show an ability to be coachable and adaptable?
- [25:17]
B
Well, you can be coachable because, yeah, you want to go through the training or the coaching that your manager or leader is giving you. But then you have to go and look in the mirror and you have to say, now I'm going to change. I'm going to adapt. And that's tough because maybe you're being told that you can't exit just like a sports team, Harry, you can't execute this certain play. And Harry's like, yeah, I know what I'm supposed to do, but I don't know how to do it. Okay, well, we have to work on the how to do it and that skill. And that's why the skills are the hardest thing to pick up. And now Harry has to go out there and train himself on those skills.
- [25:54]
C
Which leader now, today, who worked underneath you adapted the most, do you think? And what was that change? We've mentioned some of the amazing people.
- [26:03]
B
I mean, the greatest salesperson that I've ever seen in my life, that's Carlo Carpinelli, who was out of Italy. He's no longer alive. He died in a plane crash.
- [26:13]
C
But what made him special? That name was unwaveringly quick for me.
- [26:17]
B
Yeah.
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C
Why. Why was Carlo so good?
- [26:19]
B
Carlo was in the, I think it's the Emilia, Romania section of Italy. He was living in the Bologna area and he'd call in the biggest companies, Ferrari, gd, Ducati. And while everyone else was calling really low in organizations, we're meeting with Piero Ferrari, we're meeting with the CEO of Ducati, we're meeting those types of people selling, you know, mechanical computer aided design software. So one, Carlo was fearless. Two, he was an amazing listener. And three, he was completely and totally secure in himself. When someone like would attack him or attack his product, he would look at you with such confusion and ask, but why? Why? And it would really disarm people because he was so genuine about it. It would disarm people and they'd have to explain themselves. And now he disarmed them and now he had them. And I'm telling you, he sold multi million dollar deals, you know, all the time at the top of those organizations. He was phenomenal. Someone else that was trained underneath Carlos, that is a phenomenal person that you should have on your podcast, it's Cedric. Pash.
- [27:34]
C
Why is Cedric so good?
- [27:35]
B
Cedric inhabits a lot of the same qualities and characteristics of Carlo. He was trained underneath Carlos. So Cedric is French. He was a very good athlete. He was on the French national downhill ski team. But he decided when he joined ptc, he told the person running Europe at that time that he wanted to only work for the best sales leader in Europe. And the guy said, well, the best one we have is this guy Carlo Carpinelli in Italy. And he goes, okay, I'm moving to Italy. And he didn't speak a word of Italian, he didn't speak English. And he went down there and learned under the tutelage of, of Carlo. So he's a great listener, very patient, very secure, and he can get to the bottom of the issue or what's going on very quickly.
- [28:21]
C
I want to be a great sales leader today. And I'm listening to you and I'm listening to this conversation. Having worked with your Carlos, having seen your Cedrics, having seen your Dagnan's, what would you advise me and what it will take for me to be a world class sales leader?
- [28:37]
B
Well, I think you have to have a great mentor. You have to have somebody that's going to teach you and coach you. And you have to be coachable, you have to be intelligent, you have to be driven, you have to be coachable, you have to be adaptable and you're going to have to work. It takes a lot of discipline. So get a great mentor and have those Characteristics.
- [28:56]
C
When have you been least disciplined in your career and why was that? When did you just feel off?
- [29:01]
B
Always when the company that I was at got acquired because now we got acquired by a much bigger company. Those sales leaders typically aren't sales leaders that really want to know what's going on at the street level. They're more bureaucratic, they're more enthusiastic, internal politicians. And that always like really frustrated me and wanted me to get out of those organizations as quickly as possible. I'll try not. If you look at my track record, you'll see which companies I got acquired by.
- [29:30]
C
Dude, I've got all of the companies written down here one by one. But there's quite a few is the challenge. It's like five public companies.
- [29:38]
B
Well, we went public and then got acquired a number of times.
- [29:40]
C
Yeah, yeah. So I mean it's, it's not exactly like an easy multiple choice.
- [29:44]
B
But I always thought the best CROs actually know. Like when I was coming up, what I realized is that I would look at the second line and third line leaders when I was a first line leader and say I don't really respect any of those guys because all we talk about in these meetings is internal politics and internal bullshit. And I'm not interested in that. Let's talk about what we have to do to help my sales guys sell more software. Then I'll get excited. So I always told myself when I'm at that level, I'm going to know exactly what's going on at the street level level.
- [30:14]
C
How do you structure meetings to get that conversation? What do we have to do to sell more software? Like literally. Can you advise me? I've got a meeting tomorrow with my sales team and I'm the sales leader. How do I change the meeting to get. What do we have to do to.
- [30:29]
B
Sell our more sales calls yourself? Go try to sell some software yourself. You should have the answers. You shouldn't be asking your sales reps, why are you asking your sales reps? They should be asking you. You got to flip the round. You got to go make more sales calls yourself with those sales guys and see where they're making mistakes. Hear what the customer's saying, see what the competition's doing. That's what you have to do. And then go try to sell a software yourself. Then you'll understand what they go through.
- [30:55]
C
How do sales leaders fuck up comms with their reps most I think because.
- [31:01]
B
They don't truly understand what the sales reps are going through and they're more desk jockeys. They're not really making sales calls with the sales reps, so they don't really know what's going on. And the, and the reps know that they don't know what's going on so they don't respect them.
- [31:15]
C
How quickly do I put a rep on a call with prospect? You're a prospect in my enterprise sales team. Well done, John. How quickly do I put you on a call with a potential customer?
- [31:26]
B
You mean if I just started? Yeah, right away.
- [31:29]
C
Right away?
- [31:30]
B
Yeah.
- [31:30]
C
I could burn a lead for an enterprise contract.
- [31:33]
B
Oh, okay. He might be on a, he might be on a call. He should be on a call listening and monitoring to someone else. Right, but he's on a call.
- [31:40]
C
When do I let you lead?
- [31:42]
B
Pretty quickly. So I believed in bringing people in, you know, giving them prerequisites of what they have to know when they show up for the training so that the training isn't, they're not learning information. You know, when they first get there, they've already gained a lot of the knowledge and now I'm going to test them on some prerequisites and then we're going to have, you know, like a week or two week long training course.
- [32:06]
C
Okay. Just so I know again, people love the granularity.
- [32:09]
A
The prerequisites are a G doc of.
- [32:12]
C
Links are an onboarding PDF. What are the prerequisites that I should be sending? So when you come in on day one, we're going to have a good informed discussion.
- [32:22]
B
Yeah. Different product case studies, the product differentiators, the competition, who's our, you know, ideal customer profile, all the information that you probably have at your disposal and making sure that they understand a lot of that before they come to training. And then when they come to training, I've always believed in, you know, giving them a little test to see what they know.
- [32:41]
C
What's that test?
- [32:43]
B
Tell me about our product differentiators. Tell me some of the stuff that was in the, in the material that I sent them. And then from that it tells me a couple things. One, if you did not prepare and you fail the test, it tells me really two things. One, Harry hasn't really taken the time. He told me he was enthusiastic about joining the company, but Harry hasn't taken the time to really understand this material. That's number one. Number two, I got a problem with Harry's manager because Harry's manager hired Harry and now he knows Harry's going to this training course, he knows Harry's going to be tested and Harry failed. I got a Problem with the second line man or the first line manager. So I give him a call and I say, hey, Harry failed. He's going to come back again to the training. And if he comes back again and he fails again, I got a really big problem with you.
- [33:32]
C
How often does that happen?
- [33:34]
B
Well, if you instill the right discipline, it probably doesn't happen a lot.
- [33:38]
C
Were people scared of you, John?
- [33:40]
B
There might be some people that were scared of me, but I think a lot of people, especially when you are stern, that's one way of interpreting it.
- [33:49]
C
Yeah.
- [33:50]
B
But if you have those characteristics that we talked about, you know, brains, drive, coachability, adaptability, at first you're going to look at me and say, wow, this, this guy's driving some discipline. He's doing a lot of training of me and helping to develop my skills. And you'll still want to buy in. And then once you buy in and see that your world has changed, you're selling bigger deals, you're making money, you could get promoted, you're never leaving. You know, a lot of the people that used to work for me, they used to work for me three times, four times, five times. But if you're not driven and you're not really coachable and adaptable, you don't want to change, then there's not much I can really do. And you probably think that I'm really tough and stern.
- [34:31]
C
When did you have to change most as a sales leader? How did you have to change and what did you learn?
- [34:37]
B
It's kind of interesting. Early on, when I first became a manager, it's going to date me, but I was at a company called hp and it was early on in HP and there wasn't any Internet yet, right? So you had a desk and you had an inbox and an outbox. It was two trays, like a tray on top of a tray. I got the cubicle of the manager that had left. So I go into the cubicle and in the cubicle is like three bookshelves, all full of these loose leaf binders. You've seen those loose leaf binders all full of paper. And then there were two big horizontal drawers of files and stacked with files. And I closed those up and I went two floors down to shipping and I used to play softball with a guy that ran shipping, a guy named John Wagner. I said, john, grab your guys and hand trucks come on up to my office. They come up and we're standing in front of the cubicle and I said, you see all those and see everything in this files Throw them out. Said, you really want me to throw it all out? I said, yeah, I want you to throw it all out. Okay, come on boys, let's go. They threw out all the papers, all I had nothing on the shelves and nothing in the file cabinets. I go make sales calls every day and I'd come back to the office, you know, with the sales rep, take all the papers that were in the inbox. And I had moved my trash can close to the side of my desk and I threw them all in the trash can because my comp plan said when my sales guys sell, I get paid. I said, simple enough. And then went from there. What would happen is people would come by and say, hey John, I sent you this thing three times and you haven't responded yet. Tell me why it's important. Tell me why it's urgent. Tell me why I have to do it. Tell me how it's going to help me sell my sales guys sell more stuff. And what I learned very quickly is what was really important, what really was urgent and really what was just a bunch of bureaucratic bullshit.
- [36:30]
C
Do you think that would still work today?
- [36:32]
B
Yes.
- [36:33]
A
Really?
- [36:34]
B
When I went to BMC after Blade Logic, I got a call from Bob Beacham. He probably remembers if he's listening. And he said, John, people keep telling me that they're sending you win loss reports, they're sending you other types of documentation and you're not answering their calls. And I said, Bob, why would I care as an example about somebody's win loss reports when your sales force sucks? I'm trying to change your sales force. Why would I look at the win loss reports and people really don't know why they won and certainly don't know why they lost. What am I going to learn from that?
- [37:08]
C
Do you think the state of sales leaders today is very good? If I'm honest, when I look at you and then there's slight. You look phenomenally young, but slightly younger. Your dagnan's and your friends that we mentioned before of the world. But you are hard. You have a cold harshness that respectfully the younger generation that I See also of 35 to 40 year old Selsie just don't have have. You are more blunt, you are more direct. It's different. How do you feel when I say that?
- [37:37]
B
Yeah, I'm okay with it because I think once people start to, you know, listen to me and, and hear me, I do have some art of the sale too. So I do know who's sitting in front of me and I can reach out to them at their level and the pace in which they want to learn. And I can help coach them and mentor them and help them grow. So it doesn't really bother me.
- [37:59]
C
One of the most challenging things is when it's not working in a sales team. When you're missing your numbers, what do you do as a sales leader, what do you say to the team?
- [38:09]
B
Well, I've done everything I can not to miss numbers. So I can't really remember like the last time I missed a number.
- [38:15]
C
Are you serious?
- [38:16]
B
Yeah.
- [38:17]
C
You never missed a number.
- [38:18]
B
I can't remember when I missed. I missed a number. We missed a number like after nine years at ptc, we missed a number after we did the acquisition at Computer Vision. So when we missed the number, but we didn't really miss numbers. So part of missing a number is have you and the CEO and the CFO sat down and actually planned and actually looked at numbers. So here's where a lot of CROs get themselves into trouble, especially first time CROs. There's a six month ramp time. You see this all the time. Let's say they're on a calendar fiscal year. There's a six month ramp time and it's November and there's a board meeting and the CEO comes out and tells the CRO, hey, you did 10 million this year with 10 sales reps, you got to do 20 million next year. He still only has 10 sales reps that did the 10 million, but he has to do 20. But he has a six month ramp time. And the sales guy says, that's great, but I need 10 more sales guys. Okay, we'll go hire the 10 sales guys. Well, when you hire 10 sales guys in a really quick period of time, chances are you're not getting A's, you're getting B's and C's. Your managers are taking the quotas. Even though the reps have quotas, the managers have the aggregation of that quota. There's not enough time for them to ramp. The managers start to beat on the salespeople, create a really bad culture. They miss the number, costs went up, they missed the number. You have a really bad board meeting.
- [39:43]
C
And then the board say fire the head of sales.
- [39:45]
B
Fire the head of sales. When really at the end of the day, the problem was the CEO didn't sit back and plan and didn't say, hey, we have a six month ramp time and we think we'll do 10 million this year based upon 1 million per guy. Then in June, we have to start hiring people, one of those 20 people for next year in order to do 20 million. Now you took the ownership of that because you planned as a CEO and you gave it to the CRO and said, okay, now hire them. And he has the time to hire them, the time to ramp them, the time to train them, create the right culture and not miss the number.
- [40:19]
C
I just raised a big round of funding and I need to have 20 more reps. What do I do? Can I hire fast and well or do I just have to acknowledge, you should have got ahead of this buddy, and now you're going to have to pay for it with a delayed hiring process.
- [40:36]
B
You should have got ahead of it. And I would say take your time and hire only eight people, otherwise it's going to come and get you at a certain point where again, you created a bad culture. You took the quota, you create a bad culture because the managers are taking the aggregation of that quota, remember? And they're not making their numbers. So managers are not making numbers. A lot of sales reps aren't making numbers. The sales managers are horse whipping the sales reps because they need to make the number. You're trying to pick up deals, you're discounting deals, you're doing all this weird shit in order to make the number. Instead of selling the right way, training your people the right way, going back to customers and upselling the right way. You just taken a lot of shortcuts because you just didn't plan right.
- [41:17]
C
How quickly do you know when someone is not very good?
- [41:20]
B
That's a good question. It's actually a tough question. Here's what I look for as a CRO. What happens with a lot of managers is let's say there is a six month ramp time. The managers feel like they're under pressure to pull a trigger on a rep when it gets close to that six month time period period. Because they feel like, hey, he really hasn't ramped. Maybe the CRO thinks that I should fire the guy because he hasn't sold anything and he's not ramping the right way in the first six months. I don't really believe in that. I think people progress at different speeds. I'll give you an example. I had a guy, can't name his name, but he's even been a CRO a couple times now. But he worked for me at a company called Blade Logic. He went and went nine months without selling a deal and Dev, David Acharya and the chairman of the board told me I would fire him and I said no, I'm not going to fire him. 10 months, 11 months, 12 months. They were really on me to fire the guy, and I said, I'm not going to fire the guy. 13 months and he sells a $1.1 million deal and a $1.2 million deal. No kidding, no exaggeration. And the reason I wouldn't fire him is because I would go and make sales calls with him just to see. And every time I was on sales calls with him or he was in internal meetings, you know, with the whole group, all the salesforce, he was always making these incremental jumps in his skill set and his knowledge because he would, he was unafraid of standing up in front of everybody and showing that he had the knowledge and the skill when we would role play. So I didn't, I didn't let him go. Now there's other people where you can see that they're not making any incremental jumps and you start to question them and then you also have to start to question the leader. Do you know specifically why Harry isn't advancing? A lot of times they give you these weird answers like he doesn't have grit. They're very, the generalizations. They haven't put their fingerprint on the fact that maybe Harry has a hard time developing a champion or obtaining metrics for, you know, a cost justification. They haven't really put their finger on the. It's this step in the sales process where Harry's getting stuck and that we, if we can get him past that, he can get, he can go the rest of the way. And that's kind of the way that I look at it, is like I'm a giant ice hockey fanatic. I don't know if you know this, but in ice hockey there's only 20 players. There's 12 forwards, a center and two wings, a left wing and a right wing, and then two defensemen and a goalie. Okay? Now if you look at those forwards, they call them the, the, the center and the two wings. They come over the bench every 45 seconds to a minute, a minute max, because the game is just, you're just doing intervals literally non stop on the ice. And I think most people don't know that that occurs. Now, a hockey coach has to be so good that he could see when Harry jumps onto the ice, he's supposed to execute that play. And I know he has the knowledge, but he didn't have the skill set to do that. Now what he does, of those 12 forwards, each line is three people. So there's four lines. I might take Harry, and he knows. Harry knows he didn't do it the right way either. And I know, but I'm going to make sure Harry really knows. And Harry was on the first line. I demote him to the third line. I say, Harry, you're on the third line for the next shift. Joe, you just got promoted to the first line. Now everybody on the bench knows Harry did something wrong. Now Harry's got a lot of time to think about what he did wrong. And now Harry may want to develop his skill, you know, next time when there's practice. And that's no different than with salespeople, you could see what they're doing wrong. As a good coach, is it knowledge on that play or is it a skill on that play? And what do I need to do to coach Harry to get him so that he can execute that flawlessly?
- [45:06]
C
Carrying this team analogy and this ice hockey team analogy, often when you win a title, win several titles, you can become arrogant, you become complacent. How do you prevent complacency and arrogance when to your point, you forgot the last time you missed a number? When your team has hit every number, how do you prevent complacency in sales teams?
- [45:28]
B
Like I said, sometimes it's driving discipline and making sure that the players are always getting trained on the right stuff. So in software, no matter what company you're at, especially any of these startups, things are constantly changing right in front of you. When products, you know, when I sold the ptc, we do a release every six months of a major release. Now you're doing releases every day, sometimes couple releases during the day. So the software's changing, competition's changing, the market's changing, your customers are getting more educated on what you sell. They're asking different questions. And you have to constantly train your salespeople. It never stops.
- [46:04]
C
Is it okay if your salespeople is super money motivated?
- [46:08]
B
Yes, sure, totally fine. But they're not all money motivated. And you can't make the mistake that they all are. You have to sit down and understand what motivates someone. So if you're driving to an account with them, used to call it windshield time. You don't look at your phone and check your Instagram. What you're doing is trying to find out if I'm driving with you. Harry, where'd you grow up? How big of a family would your dad do? What'd your mom do? I'm trying to figure out kind of what motivates Harry. Where did he come from what? What does he want to be? Why is he here? How much money does he want to make? Is that what drives him or something else? Drive, Harry. And when you understand somebody's motivation, it's a little easier to train them and coach them and motivate them as a leader.
- [46:46]
C
Did you have a number growing up, a number that you wanted to make?
- [46:51]
B
Oh, Harry, I was lucky if I even thought I'd make, you know, a million dollars. I was a poor kid.
- [46:56]
C
So did you not always know you were going to be successful?
- [46:59]
B
If there's one thing that I have, I won't say that I'm the smartest guy. I won't say I'm best presenter, any of those things. But when you talk about persistence, heart and determination, mine's off the charts. Like, if you're going to beat me in a cell, you better get up really early and go to bed really fucking late because I'm going to beat your ass.
- [47:19]
C
Why does that come from?
- [47:20]
B
Comes from my, my childhood and you know, my dad. My parents didn't even go to high school, my dad didn't even go to junior high school.
- [47:28]
C
And so how did that impact your.
- [47:30]
B
Persistency that if you want something, you have to go and go and get it and it's not going to come easy, it's going to come through a lot of hard work. It sounds like a cliche, but you're going to get your ass kicked a number of times. You got to keep just getting up and going again.
- [47:43]
C
When did you get your ass kicked most?
- [47:45]
B
So when I just got out of college, my best friend died of drugs and alcohol. Well, drugs. And then my dad died a couple months later and then my second best friend died of alcohol. It was a really year, but it set me straight, you know, when a lot of people were still going out and saying, you know, let's go party because, you know, our buddies would still want us to do that. I was like, nah, just didn't seem right to me. So it set me on a different, different trend at that time. I would, you know, go to work and then just go to the gym and until the gym closed. So I'd, whatever I could do racquetball, lifting, you know, anything like that.
- [48:23]
C
Funny, I'm an investor for a living as well as obviously doing the media side. And I love athletes and I love investing in athletes. And the reason I do is because you are willing to sacrifice time and yourself for no immediate reward or gratification. It comes in the future and you have to have this continuing belief that if you do do this, you will see the gains in the future without promise of them.
- [48:45]
B
Hey, there was a lot of times I was coming back on airplanes or coming back from sales calls and wondering, you know, what am I doing? Am I. Is this ever going to go anywhere? Am I ever going to make any real money?
- [48:58]
C
Do you remember when you made your first real money?
- [49:00]
B
Yeah. Well, it depends upon what you qualify as real. But, yeah, for me, it happened at ptc. I made a little bit of money.
- [49:07]
C
What was real money? I mean, back then, like 100 grand or.
- [49:10]
B
No, I made, like, you know, a couple million bucks.
- [49:13]
C
Yeah, that is real money.
- [49:14]
B
Yeah.
- [49:15]
C
You said you're a poor kid. Did that make you happy?
- [49:18]
B
It makes you happy, but at the same time, you have this giant fear of failure and giant fear that you could. That it could be all taken away pretty quickly. Does that make sense?
- [49:26]
C
It does.
- [49:27]
B
You have to get over that.
- [49:28]
C
Were you closer to your mother or your father growing up?
- [49:31]
B
My father, even though he was not someone that was going to share, like, feelings or anything.
- [49:36]
C
And so you desperately wanted to prove yourself to him.
- [49:39]
B
Yeah, I guess you could say that. And then if we're getting into a therapy session, which isn't too bad, it's also, you know, he grew up, never went to junior high school. His mom died when he was born. His dad was alcoholic and left him and his brother on the streets of New York to fend for themselves. You know, as an example, I asked my uncle. My dad died at 48. My uncle lived to 93. But I asked him, like, they really didn't want to tell stories. But he told me that, you know, when they were 13 or 14, they got sent to a. A farm out in Long island, and the woman who was hosting them lost the farm and then went to the neighbor next door, farmer next to us, asked if you could take these kids in. He said, yeah, I could take them in, but they have to live in the chicken coop. And they lived in a chicken coop for two years in the harsh winters and summers. Then I think about my father and think the way in which he suffered, at least for me to have a decent childhood, that I wasn't going to let that, you know, go away without me trying to be somebody.
- [50:37]
C
Do you have children?
- [50:38]
B
Yeah, I have a son and a daughter.
- [50:40]
C
How did that. And seeing your father suffer in that way and hearing about that impact, how you think about bringing up your children?
- [50:47]
B
I bring them up differently than I was brought up. I probably lived in a. More of A violent household, dysfunctional household. And I wanted to make sure that my household was not dysfunctional. So I brought up my kids to, you know, get the best education and not have to ever deal with any type of, you know, household violence.
- [51:07]
C
Do you struggle with the realization that you are, this is my words, the brilliant man that you are today because of the dysfunction and because of the suffering that you had in childhood, whether it was just being poor or seeing challenging times? And you almost want your children to suffer because it turns them into the sturdy, material man that you are today. And if you remove all of that and just put. Put them in this very isolated, warm, cozy environment, they won't be the man that you are today.
- [51:34]
B
That's something that you definitely think about. But, you know, how do you. How do you balance that? Like, both my kids are working. I don't give them any money. I don't give them really anything. They. They're. They're on their own. If they call me with a problem, I say, like, you got to figure it out.
- [51:48]
C
What would be your biggest parenting advice to me? You know, I. I care a lot about children. I want to have children very much.
- [51:55]
B
I'll tell you a story.
- [51:56]
C
Yeah.
- [51:57]
B
So when my son was young, I remember coming to my wife and saying, I can't remember specifically what it was, but I remember what I said. I said, you know, he's not like me. And she said, that's because he's not supposed to be like you. And I said, well, what do you mean? And she said, he's not supposed to be like you, because if he was like you, you wouldn't learn anything else on this earth. And he's not exactly like you. So you can learn through his eyes and through his experiences, new things. So as an example, then it opened my eyes, and I remember the first time that my son said, you know, I want to go fishing. And I was like, fishing? I've never fished in my life. Okay, off we go. Went to Walmart, bought a bunch of rods, opened up a book, how to, you know, how to put the line on a hook, what type of bait to use, all those types of things. So when you become a father, I think it's really important to look through the eyes of your child and say, like, this is a new experience for them, but it's a whole new experience for me. I'm going to learn so many more things in life through them. Dude.
- [53:04]
C
When you were saying about persistence, Jenny, anything that was in my head, I'd like to be against you. Because I'm as persistent as you are.
- [53:12]
B
Good, let's go.
- [53:13]
C
I'm as competitive as you are. And you know what scares the shit out of me? I don't know if I am, if I want to be there for bath time, I'm not. Dude, I'm gonna, I need to go to bath time. So I'm gonna lose an inch on this competitive Harry side because I want to get home for dinner with my kids.
- [53:30]
B
Yeah.
- [53:31]
C
How do you maintain the ruthless machine operator that you are sales leader and have kids.
- [53:38]
B
It's balance. So you can't decide that you're gonna come home on the weekends and then go out golfing with the guys for five, six hours. You got to get up early in the morning. So I used to get up, you know, if I was home and get up at 10 to 5, I do my workout and I'm showered and everything and ready for when those kids get up and just before they, you know, go off to school.
- [53:59]
C
10 to 5?
- [54:00]
B
Yeah. Every day.
- [54:01]
C
What time are you going to bed?
- [54:02]
B
It wouldn't really matter because also when.
- [54:04]
C
I'm in the morning, it does matter, John. I'm gonna be. I'm gonna be dead.
- [54:08]
B
When you travel, by God did and you're always in different time zones. You're basically in constant jet lag. Right. Like Boston to Tokyo's 12 hour time difference. So when you go to bed, you're supposed to wake up. When you wake up, you're supposed to go to bed. So you're in, you're in constant jet lag. So you have to force yourself to do what you need to do for your family and for your job.
- [54:29]
C
Working out is a clear part of your life. I can tell.
- [54:33]
B
Yeah.
- [54:33]
C
You work out even when you're traveling.
- [54:35]
B
Yeah.
- [54:35]
C
How do you do that?
- [54:36]
B
In gyms and hotels or find a local gym? Yeah. Or when I do look for a hotel, I'll go to sites and say, you know what's the best gym hotel in London, in Boston, in New York, in Tokyo. And that's the hotel I go to.
- [54:50]
C
Is that your non negotiable?
- [54:52]
B
That's pretty much a non negotiable. Yeah. I feel like I'm a lot calmer, I'm a better listener, a more patient. When I've worked out and you need it, I mean more and more they're proving that there's two things to longevity, right. Muscle mass and VO2 max. And that's a. There's a balance to those too.
- [55:11]
C
Do you find the best sales leaders.
- [55:13]
B
Are also athletes not all the time. And they don't have to always be guys. I've had some women work for me, which is phenomenal. Salespeople blow you away.
- [55:23]
C
Who's the best female sales leader you've ever worked with?
- [55:25]
B
A woman named Anne Gary. She's phenomenal. Now she works with John Kaplan at Force Management. She's amazing.
- [55:33]
C
What do you know now that you wish you'd known when you started?
- [55:37]
B
I'm going to go back to listening. Like, I had to learn how to be a great listener. And I think that is the number one skill of a leader, Number one skill of a recruiter, number one skill of a salesperson is really learning how to listen. So a lot of times, as an example, if we tell stories, if somebody wants me to help them out with their company, say, they say, what's the best way to enter and understand the salesforce? Invite me to a QBR where they're going over the forecast. I'm hearing everything right there, right? A lot of times you'll see the CRO and maybe even the CEO ask questions and then they'll say, okay, how are you? Done? Yeah, he's done. I go, well, hold on a second. Do you mind if I ask a question? And then I'll say, hey, Harry, when you were up there, you said this. Tell me what you mean by that. And all of a sudden, here's come a can of worms. Sometimes people are just trying to get through the questions because they have an audience, especially the CRO or first or second line managers. They're more impressed with their position of power than they are of truly trying to coach and mentor the sales rep. It becomes a show instead of a true coaching and training session. Because if Harry's making a mistake and I have 200 salespeople in the room, another hundred of them have the same problem or they're going to see the same problem at some point in the sales process.
- [56:57]
C
John, what's the voice in your head when your alarm goes off at 10 to 5? When your alarm goes off at 10 to 5 and you're in Tokyo and you're tired as shit and you are going, I don't want to be here. I want to stay in bed. I want to be with my wife. Fuck this day that's about to happen. What do you tell yourself at 10 to 5?
- [57:16]
B
Dude, you haven't seen, I pop out of the bed all the time. I never lay in bed when the alarm goes off. Never actually have a rule. If I lay in bed four days in a row, which has happened. I quit the job. That's when I know I have to quit. I call the CEO up and I quit. Something's wrong. Because usually as soon as that alarm goes off, there's 10 things in my head. My feet hit the floor and there's now 15 things in my head.
- [57:40]
C
Were you always like that?
- [57:42]
B
Yeah.
- [57:42]
C
Yeah, that's what. We were different, my friend.
- [57:47]
B
What are you gonna have? A cup of coffee and a donut?
- [57:49]
A
Are you freaking kidding me?
- [57:50]
C
I've got an alarm. You're gonna hate me. I have an alarm at 8:15. At 8:20. At 8:25. And then my EA will call me at 8:30 and go, Harry, your meeting's at 8:30.
- [58:01]
B
I'll go. Fuck. Fuck. Fuck.
- [58:03]
C
Shit. Okay, message him. I'm giving me 10 minutes late.
- [58:06]
B
That's not me. I'm out.
- [58:07]
C
Yeah, no, that's me. But I am up until 2:30, which is very bad.
- [58:13]
B
All the time.
- [58:14]
C
Yeah, Every night, sadly. I live in the UK and I work us.
- [58:18]
B
Oh, right.
- [58:19]
C
That's difficult.
- [58:19]
B
Yeah.
- [58:20]
C
But you get credit because everyone's like, wow, you work so late. And you're like, no, I kind of work us days, but in the uk, so, like, you know, dude, I want to do a quick firearound with you. What's the biggest BS that you see in sales today?
- [58:32]
B
That everybody can sell their product through plg, and it's just not true. You can't sell every product can't be sold through plg.
- [58:39]
C
What product cannot be sold through plg?
- [58:42]
B
Ones that are really complex and need multiple stakeholders from multiple departments to buy into. I don't know how you get them to all agree.
- [58:50]
C
What's really interesting again, as a venture capitalist for a living, is we have changed what we expect companies to do in terms of revenue so dramatically. When I was growing up, 10 million in 18 months was amazing revenue scaling in the first 18 months. Now if you don't do that in the first place, four months, you're not very good. You're not top tier. And in enterprise sales, obviously you ramp time and you know, it takes time.
- [59:14]
B
But also people get caught in that, what I call PLG trap too. Right? They come out quickly. They only sell through plg. They build their cost model around plg. They build the whole culture around plg. All of a sudden, and you've probably seen these companies, all of a sudden, they realize, oh my gosh, we need bigger deals. We need to go to the enterprise. Then you tell them that they have to hire $300,000 sales guys at OTE and change their cost model and change the people that they have in the company and the way in which they go to market and think about it, and they just can't do it. And a lot of them go way up really quickly and boom, they hit a wall.
- [59:49]
C
I literally have goosebumps. Because PLG works when expansion happens, and when expansion doesn't happen and you have the cost structure to expect expansion to happen. Ouch.
- [59:59]
B
Yes. Yes.
- [60:00]
C
That is a real pain.
- [60:01]
B
Okay, so you've seen the same thing.
- [60:02]
C
What have you changed your mind on in the last 12 months?
- [60:05]
B
That if the CEOs that I am on the board with, if they really don't want to change, then there's no reason for me to be on their board anymore.
- [60:16]
C
Which board has been the hardest one to leave?
- [60:18]
B
Hardest one to leave was probably Snowflake and Mongodb.
- [60:22]
C
Why?
- [60:23]
B
Well, Snowflake, I was there two years before they had a product, so I was there very early. And Mongo, I was there when Dave went in. So when he went in, he asked me to come down to New York and he'd give me access to all the people and any information I wanted. He wanted me to look at the company without him and then tell him, this is what I found. This is what I see. And then he wanted to see if that matched with what he was seeing, what he found. So I was in both those companies, you know, really early, build some good relationships with people, and it's kind of difficult to leave, but eight to 10 years, you have to let somebody else.
- [61:00]
C
Do this remote work. Total bullshit. For sales teams or a new generation of how sales teams work, I think.
- [61:08]
B
It still has to be a combination. I understand that there's times when you can get access to people and even people at higher levels through remote work, which I didn't think was possible years ago, but it is possible. So that's a benefit of it. I think the downside of it is what I loved is one of the powers that I thought I had is I had really good intuition. So I would go in a room and walk around the table to introduce myself, and I'd try to say, okay, this person's a gatekeeper. This person was told to be here, but they don't give a shit. This person could be a champion. This person, the way they looked at me and. Or didn't look at me and shook my hand, their potential enemy. So I would do that, and then I'd match it against what was happening in the meeting so that I could see whether or not my gut was right or my gut was wrong. And constantly adjusting my gut and gut feel is something that's really difficult to do, at least for me to do over zoom. But if I'm in a room with you, I can feel you. And I can feel like whether or not you're resisting me or you're the.
- [62:12]
C
Charisma, the eye contact, all of that stuff.
- [62:14]
B
And I think intuition for a salesperson is something that is super powerful because then you have two processing engines. You have your own, your brain that's processing information, but you also have your gut that's processing information. And I like to know that they ring true, that my brain is ringing with my gut. And when my brain's not ringing with my gut, something's wrong. Then it makes me go try to figure out what's wrong, what are you doing? What are you seeing and hearing and feeling? That's wrong. And I think that's essential for a salesperson. It's something that they lack. When you do remote work, the worst.
- [62:50]
C
Deals were all in 2021 when we did remote investing. And you didn't see the material of the founder, the substance of what it's like to look in their eyes and how they open the door and how they carry themselves. Always the worst. Who's the best CEO that you've worked with?
- [63:05]
B
The single best, early on it was Steve Walsky at ptc. He was super smart and could see, see a lot of things happening before they happened. And then I'm going to name a couple of people, right? Brian Halligan's really frickin smart.
- [63:19]
C
Also charming and funny.
- [63:21]
B
Charming, funny and adaptable, you know, And Brian's another one of those that doesn't. If you say something that's like against what Brian thinks, he does, ponder it, he does consider it. He's not offended by it. He's, he's, he's pretty secure in the way in which he hears you. And then he goes and considers changing or adapting. Brian's very, very smart. And then I'd say David Acharya too, he's better. Brian or Dave, they both have different styles. Dave is very intimidating to a lot of people. Really intimidating. Even if you tell Dave that, he's still sometimes intimidating to people. But, and, and Brian has a different type of style. So Brian can get, get probably more information out of you. Whereas I think that some people, if they're intimidated by Dave, they don't give him the information that he should get as a CEO because they're almost, they're a little afraid.
- [64:17]
C
You know, the joy of what I do is you don't see what someone is often quite like behind, you know, closed doors, and they show you a very nice facade. And very often I will see people like Dave, who I've known now through the show for many years, and he's always just wonderfully nice and charming and brilliant with me. And then people like, oh, he's terrifying. I'm like, dave, Davey's a little sweetie.
- [64:36]
B
Like, we're masterful. He's not. But I've seen him in meetings where he does intimidate people. I don't even, I don't know if he knows that he intimidates some people.
- [64:44]
C
But final one for you. If I were to summarize all of your podcasts, conversations, advice, guidance to the many people that we've had on the show and to everyone listening, and you could only leave them with 60 seconds worth of content or advice, what would that 60 seconds be?
- [65:03]
B
Become a great listener. It's not about you, it's about the customer. Understand as much about the customer as you possibly can by prepping and doing your homework. And be very reluctant to talk about your product capabilities until it's. Until it's the right time.
- [65:21]
C
John, I owe you so many thanks for passing so much wisdom on to so many of the people who I've interviewed before. This was such a joy to do. And I love conversations which go in very strange and circuitous routes. So thank you for being so patient with me.
- [65:36]
B
You're welcome. It was easy, Harry. It's easy.
- [65:40]
A
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- [67:37]
C
To to win deals.
- [67:39]
A
Then we started using Miro's Innovation workspace and honestly, it changed how we operate. So here's what clicked. Miro AI doesn't just give you a blank canvas to do dump ideas, it actively helps you structure your thinking. We used it to synthesize founder interviews and diligence notes, pull out key patterns and turn them into an actual investment memo in hours, not days. And speed is really important. Miro's AI sidekicks review your work like a seasoned GP would, pointing out gaps in your thesis and suggesting what to.
- [68:10]
C
Dig into next and when.
- [68:11]
A
We needed to map out portfolio strategy, Miro generated frameworks and visual roadmaps right from our board.
- [68:18]
C
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- [68:20]
A
Help your teams get great work done with miro. Check out miro.com to find out how. That's miro m I r o dot com.