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John McMahon

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2025-11-28
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2025-11-28
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  1. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. He's not, but I've seen him in meetings where he does intimidate people. I don't even know if he knows that he intimidates some people.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. 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 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 a little afraid.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. 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 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 Acharia, too.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. 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 people, right? Brian Halligan's really freaking smart.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. 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, 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 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. 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 pressing me.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. 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 really good intuition. So I would go in a room and walk around the table to introduce myself and I 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 or didn't look at me and shook my hand, they're 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. Hardest one to leave Probably Snowflake and MongoDB Well, Snowflake, I was there two years before they had a product, so I was there very early. And Mongo, I was there when... 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 was kind of difficult to leave, but eight to ten years you have to let somebody else do this.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Also, people get caught in that what I call PLG trap, too, right? They come out quickly, they only sell through PLG, they build a 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Once had 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. You haven't seen, I pop out of the bed all the time. I never lay in bed when the alarm goes off. Never. I 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. 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, they say, what's the best way to enter and understand the sales force, 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 you hear come a can of worms. Sometimes people are just trying to get through the questions because they have an audience, especially the

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. Not all the time, and they don't have to always be guys. I've had some women work for me, we're just phenomenal salespeople, blow you away.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. That's pretty much a non negotiable. Yeah, 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. When you traveled 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 constant jet lag. So you have to force yourself to do what you need to do for your family and for your job

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. 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 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. Yeah, every day

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. 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 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. That's something that you definitely think about. But, you know, 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 on their own. If they call me with a problem, I say, like, you got to figure it out.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. 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 household violence.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. 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 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 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 a check-in 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. It makes you happy, but at the same time you have this giant fear of failure and giant fear that it could be all taken away pretty quickly. Does that make sense?

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. 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? Is this ever going to go anywhere? Am I ever going to make any real money?

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. 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. I was like, nah, just didn't seem right to me. So it set me on a different trend. At that time, I would 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. 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

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. Comes from my childhood and my dad. My parents didn't even go to high school. My dad didn't even go to junior high school.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. 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 sal, you better get up really early and go to bed really fucking late because I'm going to beat your ass.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. 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? What'd 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 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. 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 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?

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. 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 a cost justification. They haven't really put their finger on. It's this step in the sales process where Harry's getting stuck. And 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. Now, if you look at those forwards, they call them 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...

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. 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 dollar deal and a 1.2 million dollar deal. No kidding. No exaggeration. And the reason I wouldn't fire him is because I would go and make sales calls with them just to see. And every time I was on sales calls with them or he was in internal meetings, you know, with the whole group, all the sales force, he was always making these incremental jumps in his skill set 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. So 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. 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 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 Acheria, 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. Should have got ahead of it. And I would say take your time and hire only A 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 have taken a lot of shortcuts because you just didn't plan right.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. Fired 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. 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 and 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 miss the number, you have a really bad board meeting.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. I can't remember when I missed it. I missed the number. We missed the number 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. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. 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. 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 doesn't really bother me.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. 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 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?

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. See all those and see everything in this file, throw them out. Say, Do you really want me to throw it all out? And 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 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...

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  46. 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 the 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,

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  47. 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 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 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  48. Tell me about our product differentiators. Tell me some of the stuff that was 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 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  49. 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 giving them a little test to see what they know.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  50. 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.

    2025-11-28 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source