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

28:21I 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 Dagnans, what would you advise me and what it will take for me to be a world-class sales leader? 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.

28:55When have you been least disciplined in your career? And why was that? When did you just feel off? 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 internal politicians. And that always really frustrated me and wanted me to get out of those organizations as quickly as possible. If you look at my track record, you'll see which companies I got acquired by. Dude, I've got all of the companies written down here one by one.

29:33But there's quite a few. Is the challenge just like five public companies? Well, we went public and then got acquired a number of times, yeah. Yeah. So, I mean, it's not exactly like an easy multiple choice. 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.

30:08Then I'll get excited So I always told myself when I'm at that level I'm gonna know exactly what's going on at the street level. 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 sell 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 How do sales leaders fuck up comms with their reps most?

31:00I think because 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 reps know that they don't know what's going on. So they don't respect them. How quickly do I put a rep on a call with Prospect? You're a prospect in my enterprise sales team. Well done, John. John, how quickly do I put you on a call with a potential customer? You mean if I just started? Yeah. Right away. Right away? Yeah. I could burn a lead for an enterprise contract. Oh, okay.

31:33He might be on a call. He should be on a call listening and monitoring to someone else, right? But he's on a call. When do I let you lead? 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. Okay, just so I know, again, people love the granularity.

32:09The prerequisites are a GDOC of links, 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. Yeah. Different product case studies, the product differentiators, the competition, who's our 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. What's that test? Tell me about our product differentiators.

32:45tell me some of the stuff that was in the material that I sent them. And then from that, it tells me a couple of things. One, if you did not prepare and you failed 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 or the first line manager.

33:21So 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. How often did that happen? Well, if you instill the right discipline, it probably doesn't happen a lot. Were people scared of you, John? 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. Yeah. But if you have those characteristics that we talked about, brains, drive, coachability, adaptability, at first you're going to look at me and say, wow, this guy's driving some discipline.

34:00He'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 that 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. When did you have to change most as a sales leader?

34:33How did you have to change? And what did you learn? 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.

35:28Come 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. He 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. I had nothing on the shelves and nothing in the file cabinets. I'd 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 what 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.

36:19Tell me how it's going to help 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. Do you think that would still work today? Yes. Really? When I went to BMC after BladeLogic, I got a call from Bob Beecham. 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?

36:58I'm trying to change your sales force. Why would I look at the win-loss reports when people really don't know why they won and certainly don't know why they lost? What am I going to learn from that? 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 slightly you look phenomenally young but slightly younger your Dagnans and your friends that we mentioned before of the world but you're hard you have a cold harshness that respectfully the younger generation that I see also of 35 to 40 year olds that you just don't have you are more blunt you are more direct it's different how do you feel when I say that yeah I'm okay with it because I think once people start to listen to me and hear me, I do have some art of the sale too.

37:46So 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. 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 well i've done everything i can not to miss numbers so i can't really remember like the last time like i missed a number are you serious yeah you never missed a number i can't remember when i missed i missed the number we missed the number like after nine years at ptc we missed the number after we did the acquisition at computer vision that's 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.

38:40So 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, oh, 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, well, go hire the 10 sales guys.

39:16Well, 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, managers have the aggregation of that quota there's not enough time for them to ramp the managers start to beat on the sales people create a really bad culture they missed the number costs went up they missed the number you have a really bad board meeting and then the board say fire the head of sales 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 i just raised a big round of funding and i need to have 20 more reps what do i do can i hire fast am 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 the delayed hiring process 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.

40:53So 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're just taking a lot of shortcuts because you just didn't plan right. How quickly do you know when someone is not very good? That's a good question. It's actually a tough question. Here's what I look for.

41:25As 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 the trigger on a rep when it gets close to that six-month time 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.

42:01He went and went nine months without selling a deal. And Dev, David Echaria, 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 with the whole group, all the sales force, he was always making these incremental jumps in his skillset and his knowledge because 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.

42:50So 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 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 generalizations. They haven't put their fingerprint on the fact that maybe Harry has a hard time developing a champion or obtaining metrics for a cost justification. They haven't really put their finger on it's this step in the sales process where Harry's getting stuck.

43:28And if we can get him past that, 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 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.

44:06Now, 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.

44:43Now, Harry's got a lot of time to think about what he did wrong. And now, Harry may want to develop his skill 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. 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?

45:23When your team has hit every number, how do you prevent complacency in sales teams? 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 a couple of 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.

45:58They're asking different questions and you have to constantly train your salespeople. It never stops. Is it okay if your salespeople are super money motivated? 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, you 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? A big of a family? What'd your dad do?

46:29What'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 did you have a number growing up a number that you wanted to make oh harry i was lucky if i even thought i'd make you know a million dollars i was a poor kid so did you not always know you're going to be successful 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 sale you better get up really early and go to bed really fucking late because i'm gonna beat your ass where does that come from it comes from my my childhood and you know my dad my parents didn't even go to high school.

47:25My dad didn't even go to junior high school. So how did that impact your persistence? And if you want something, you have to 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. When did you get your ass kicked most? 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 shit 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.

48:07I was like, nah, just didn't seem right to me. So it set me on a different trend. At that time, I would, you know, go to work and then just go to the gym until the gym closed. So whatever I could do, racquetball, lifting, you know, anything like that. It's 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.

48:44hey 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 do you remember when you made your first real money 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 what was real money i mean back then like 100 grand or no i made like you know a couple million bucks yeah that is real money yeah you said you're a poor kid did that make you happy 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 it does you have to get over that were you closer to your mother or your father growing up my father even though he was not someone that was going to share like feelings or anything and so you desperately wanted to prove yourself to him.

49:38Yeah, I guess you could say that. And then if we're getting into 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

50:07farm out in Long Island. And the woman who was hosting them lost the farm and then went to the neighbor next door, farmer next door, asked if you could take these kids in. And he said, yeah, I could take them in, but they have to live in the chicken coop. And they lived in the 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. Do you have children? Yeah, I have a son and a daughter. How did that and seeing your father suffering that way and hearing about that impact how you think about bringing up your children?

50:46I 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 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 them in this very isolated warm cozy environment they won't be the man that you are today 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're they're on their own if they call me with a problem i say like you got to figure it out what would be your biggest parenting advice to me you know i care a lot about children I want to have children very much.

51:54I'll tell you a story. 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.

52:47So 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. When you were saying about persistence, do you know anything that was in my head i'd like to be against you because i'm as persistent as you are and 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 yeah how do you maintain the ruthless machine operator that you are a sales leader and have kids it's balanced so you can't decide that you're going to 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 i 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 10 to 5 yeah every day what time you gonna bet it wouldn't really matter it's also in the morning it does matter john i'm gonna be i'm gonna be dead when you travel like i 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 working out is a clear part of your life i can tell yeah you work out even when you're traveling yeah how do you do that 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 is that your non-negotiable that's pretty much a non-negotiable.

54:53Yeah, I feel like I'm a lot calmer. I'm a better listener. I'm 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 there's a balance to those too. Do you find the best sales leaders are also athletes? Not all the time. And they don't have to always be guys. I've had some women work for me with just phenomenal salespeople blow you away. Who's the best female sales leader you've ever worked with? A woman named Anne Gary. She's phenomenal. Now she works with John Kaplan at force management.

55:31She's amazing. What do you know now that you wish you'd known when you started? I'm going to go back to listening. 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, 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, Harry, you done?

56:13Yeah, 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.

56:57John, what's the voice in your head when your alarm goes off at 10 to 5? When the 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? 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, I 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.

57:32Because 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. were you always like that yeah yeah that's what we were different my friend what are you gonna have a cup of coffee and a donut are you freaking kidding me i've got an alarm dude you're gonna you're gonna hate me i have an alarm at 8 15 yeah at 8 20 at 8 25 oh no and then my ea will call me at 8 30 and go harry your meeting is at 8 30 i go fuck fuck fuck shit okay i messaged him i'm gonna give me 10 minutes late no that's not me i'm out yeah no that's me but I am up until 2 30 which is very bad yeah all the time yeah every night sadly I live in the UK and I work US oh right that's difficult yeah 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 fire around with you what's the biggest BS that you see in sales today 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.

58:38What product cannot be sold through PLG? One's at a really complex and need like multiple stakeholders from multiple departments to buy into. I don't know how you get them to all agree. 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 like 10 million in 18 months was amazing revenue scaling in the first 18 months. Now I mean, if you don't do that in the first four months, you're not very good. You're not top tier. And in enterprise sales, obviously, you ramp time and it takes time.

59:14But 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.

59:48I 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. Yes, yes. That is a real pain. Okay, so you've seen the same thing. What have you changed your mind on in the last 12 months? 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. Which board has been the hardest one to leave? Hardest one to leave was probably Snowflake and MongoDB. Why? Well, Snowflake, I was there two years before they had a product.

1:00:25So 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 ten years you have to let somebody else do this. Remote work, total bullshit for sales teams or a new generation of how sales teams work?

1:01:07I think 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 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, they're a potential enemy.

1:01:48So 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 with me. The charisma, the eye contact. All of that stuff. And I think intuition for a salesperson is something that is super powerful because then you have two processing engines. You have your own brain that's processing information, but you also have your gut that's processing information.

1:02:27And 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 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 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?

1:03:04The single best. Early on, it was Steve Walski at PTC. He was super smart and could 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 freaking smart also charming and funny 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 in the way in which he hears you and then he goes and considers changing or adapting. Brian's very, very smart.

1:03:45And then I'd say David Acharya too. Who'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. And Brian has a different type of style, so Brian can 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 uh afraid 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 he's a little sweetie like we're to me 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, but.

1:04:44Final 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? 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 the right time. John, I owe you so many thanks for passing so much wisdom on to so many of the people who I've interviewed before.

1:05:28This was such a joy to do. And I love conversations which go in very strange and secure to truth. So thank you for being so patient with me. You're welcome. It was easy, Harry. It was easy. but before we leave you 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 global spend management with conversational AI to deliver best user experience for everybody dealing with company spending.

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