


25 Oct 2026 · 1h 14m · 30 chapters
John McMahon (Topline) discusses the “PTC lineage” of CRO leaders, how revenue teams should be built, and how to determine whether someone is truly ready to be a CRO. He also covers CEO/CRO dynamics, commission incentives, AI’s impact on sales research vs. qualification, and why sales craft can’t be reduced to scripts.
John McMahon is a five-time CRO at publicly traded companies; his team at PTC created Medic, a widely used sales methodology. He helped develop OpenAI’s new CRO role (Dali Rajic). He’s the author of The Qualified Sales Leader and Proven Lessons from a Five-Time CRO. Hosts: Sam Jacobs (Topline), Asad Zaman (CEO, Sales Talent Agency), A.J. Bruno (CEO, Quotopath).
CRO success is driven by recruiting, onboarding, coaching, and leadership—not forecasting alone. “Opportunity, not title.” Don’t hire CROs who haven’t carried a bag/been an IC for enterprise complexity. CEOs can “ruin companies” if the CRO isn’t strong enough to challenge them. AI tools that only verify calls are “garbage” without true qualification.
Dali Rajic brought people from Whiz into OpenAI; Brian McCarthy moved from working with Dali to CRO roles and then into Etsy AI/Cursor (acquired by Etsy AI). He cites Anthropic vs OpenAI competition and commission plan caps.
Written by AI. May contain mistakes.
Discussion on John McMahon's influence and the importance of strong sales leadership.
“I'm joined by my co-hosts, as you know, Asad Zaman, the CEO of Sales Talent Agency, and A.J.”
Exploration of the lineage from PTC and its impact on sales success.
“We're excited to have this conversation.”
John discusses the importance of hiring for characteristics rather than just experience.
“And they've seen themselves do things that they never thought they were capable of, get promoted, make money, and have real positive outcomes.”
Insights into how sales professionals should evaluate job opportunities and career moves.
“And you're going to be working around great people.”
Discussion on whether prior sales experience is essential for CRO positions.
“How do these next bunch of companies get this sort of approach to go to market if all these leaders are already in seat?”
Learn the complexities of transitioning from transactional to enterprise sales and the skills required.
“Okay, I got to call on the GEs of the world where I have divisional CIOs and then I have corporate CIOs, and I have to get a common decision criteria in order to jam this deal through.”
Explore the dynamics of sales commissions in fast-growing companies and their implications.
“And it's becoming more and more competitive.”
Understand the signs and personal readiness for taking on a CRO role.
“John, I've been thinking about age a lot.”
Learn how CROs should assess potential employers and the types of CEOs they may encounter.
“When you hear, why did Sam not make that, oh, he doesn't have grid or they make up some characteristic thing that Sam is lacking.”
Discover the strategic role of CROs in relaying product issues and understanding market needs.
“So then they I can actually almost kill their own company, the CEOs.”
Discussion about the challenges of demand generation and marketing.
“what do you think about compound growth marketing and why do you love them?”
Hosts discuss methods to keep track of deals and sales processes.
“Well, Sam, I have a call with Apollo from DevRev next week to do exactly that.”
Discussion on how buyer information access is changing sales strategies.
“We're in this shift now where you've got these AI companies that have really shown us a whole new way of building, the speed at which they are scaling, the speed at which they're shipping product.”
Exploring how AI changes the sales landscape and the importance of human sales tactics.
“And then the customers heard that point of view three times already because that's all the lazy salesperson did.”
Delving into the need for building consensus within organizations during sales.
“Oh, we're going to go see your champion?”
Learn about the evolving nature of sales and the balance between formulaic selling and creativity.
“Why don't we go over and talk to AJ and find out what the paper process is and all the different people that were involved in that approval process.”
Discover the importance of being authentic and in the moment in sales conversations.
“I haven't really seen it, but I don't believe in it.”
Explore the key skills that differentiate great sales leaders beyond mere forecasting.
“And some of these other guys, Mahomes and some of these other guys, it just doesn't make any sense.”
Understand the differences and challenges in transitioning to SMB sales from enterprise sales.
“And for$10,$15,$30 million, good luck selling a deal like that with Mindy.”
Learn the characteristics to look for when assessing potential sales hires.
“It doesn't matter if it's SMB or enterprise, you know, it can't be cookie cutter.”
Insights into Mark Roberge's development as a CRO and the importance of adaptability.
“And when you dig in deep, you find out their character.”
Discover insights on effective coaching and collaboration with CROs.
“but the second part which is the talking about roberge again for a second he didn't carry a bag before he was a CRO.”
Explore the value of go-to-market experts in board-level decisions.
“But what I have seen from the best CEOs like Frank Slootman, David Acharya, some of those people that what they did with their board is they probably figured out.”
Learn how leadership styles and accountability evolve with experience.
“I got to the point where I figured, you know, in sales, no one's going to throw a fastball past me.”
Examine how the fundamentals of sales have remained constant over two decades.
“Like, where am I going to put heads and when is this guy not going to make it and puts them over here?”
Understand the challenges of hiring and the importance of sales manager training.
“that is optimized for this environment would be a different kind of person than maybe 20 years ago?”
Discover how a strategic approach to hiring impacts sales productivity.
“Like, especially did it a lot to Dave in a chair.”
Discuss the importance of P&L fluency for CROs and their teams.
“the P &L fluency, not just the CRO, but the executive team has needed to be up-leveled.”
Learn about the characteristics that set exceptional leaders apart.
“So a couple of famous people that have reported into you or come out of your lineage and get your like quick take on what made them special, what made them different.”
Learn about the characteristics that make successful Chief Revenue Officers.
“Like what made some special, what made some different?”

Get the gist, explore an idea or ask about something said.
On Topline, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00John McMahon may be the greatest CRO of all time. He played a key role in the development of the new CRO at OpenAI, Dali Rajic. He's also been the CRO at no less than five different publicly traded companies. And one of the most widely used sales methodologies, Medic, was developed by his team at PTC. In sales, no one's going to throw a fastball past me. No spitballs, no curveballs. I'm knocking the thing out of the park, right? In today's episode, John shares how the best revenue leaders build their teams. Plus, how to tell whether somebody is truly ready for the CRO seat, and what he checks before he'd hand anyone the job.
0:35You're not ready. You're going to fail. Your ego's not going to be able to take it. You're going to blame it on... Also, he shares how sales leaders must navigate their relationship with CEOs if they want to survive in the business. They think they know sales. So sometimes they can ruin companies, especially if the CRO's not strong enough to say... If you're building a revenue team that's going to stand the test of time, This episode is for you. Welcome to Topline. Hey, everybody. It's Sam Jacobs. Welcome to Topline. I'm joined by my co-hosts, as you know, Asad Zaman, the CEO of Sales Talent Agency, and A.J.
1:10Bruno, the CEO of Quotopath. And we, this is a special show, we've got perhaps the most famous sales leader in technology history on the show, the legendary John McMahon. From what we know, the only human to have been the CRO of five different public companies Under his watch, Medic was created and implemented at PTC, now the most widely used sales methodology in tech. Over 100 CROs today were part of his teams at some point, including the current CRO of OpenAI. And he's also, of course, the author of The Qualified Sales Leader, one of my favorite books about sales, Proven Lessons from a Five-Time CRO.
1:48John, we're really, really excited to have you on the show today. Welcome to Topline. Thank you, Sam. Appreciate it. Great introduction. I hope I can live up to it. We hope so too. We're confident that you can, but you know, he used the qualifier, perhaps the greatest sales leader. So you have to elevate to the greatest sales leader in this conversation. The next 60 minutes will tell us whether it's true or false. That's right. Well, Asit's going to kick us off. We're excited to have this conversation. The place we wanted to start, John, is the lineage of PTC. I think in terms of go-to-market, it's the strongest, most popular lineage of go-to-market professionals.
2:33And as Sam said, 100 CROs, probably more, right, have come through. How many is it? I don't know. Somebody once counted up like over 300, but you know. Oh my God. In fact, you know, and I still get calls. Like last week I got a call. I won't say what company, but it's a red hot startup in the Bay Area. It's got name recognition already. And the president and co-founder called me and said, I said, why are we talking? And he said, because everyone I'm talking to comes from your tree. that's crazy i am i got a call from a hedge fund about a year and a half ago and they'd made a billion dollar investment in the software company that wasn't doing well it was a publicly traded company and they realized that go to markets their biggest issue and so they reached out and they're like we want to figure out how to convince john mcmahon to come back and be a cro and you'd just done the grit episode where he'd like been trying to convince you to become an operator again and you're like, no, I like giving back this way.
3:33I was like, guys, there's no world. Then they started throwing out crazy numbers. They're like, what if we structure the equity this way? And he makes a hundred million. I was like, just call him, man. Like, why are you calling me? I don't even know, John. Well, they could always make an offer.
3:48So I think the place to start is, what does this lineage, how does it actually work? Because I think from the outside, people think it's like this one big happy family and everybody's friends and all of this. But right now, we're seeing this boom for enterprise sales. You've got AI companies that have mid-market sales cycles and almost like expanded enterprise deal sizes at the onset and then so much room to run. So everybody wants these enterprise sellers, a lot of your people. How does it work? Like, if you get Dali, so OpenAI has him, does he get the best sellers now and then the second person in line gets the second best etc like how does this actually work i don't know that it works like that yeah everybody has a treat or people that they brought along so dolly certainly has you know people that he's brought along through whiz and now into open ai um you know i had people that worked for me three four or five times um and then so i think every all of those people have branched off and they have their own set of disciples, followers, I don't know what you want to call it, that believe in their leadership and believe in their methodologies.
5:06And they've seen themselves do things that they never thought they were capable of, get promoted, make money, and have real positive outcomes. And when you do that with anyone, no matter who the person is, certainly they're going to start to follow you again, right? Because the flip side of it is you always hear people don't leave companies, they leave managers, right? So if you have a really good manager that has invested in you, has pushed you to maybe areas you didn't think you could get to, and then you got to them because they saw your potential, and then you made more money and got promoted, and now you have a great opportunity on your own, you're going to keep coming back.
5:48And then they know how to do that with other people, right? They've seen people do it to them, and now they do it to other people, and it just keeps feeding itself. Brian McCarthy was the CRO rubric, and then he became the head of Etsy AI, Cursor, and then they got acquired by Etsy AI. And it was really interesting to see. He used to work for Dali. And so when Dali took over OpenAI, he left that CRO role to come be the VP of Worldwide Sales for him. So what you're saying about they've had a certain experience with a certain person, and they like working with that person, they'll follow that person.
6:20In some cases, they'll give up seniority to be with that person as well. It's really interesting. Yes, absolutely. Because they know it's a good opportunity. Those types of people don't confuse position with opportunity. Many people, when they're looking at new job opportunities, confuse position with opportunity. So they'll tell me like, here's the couple of companies I'm looking at and I listen, I go, okay, well, that's a really good opportunity. And what's your title going to be there? well, director level, okay. Tell me about the other one. Well, this one, I'm going to be a CRO. And the way they even explain it, it's not going to be a good opportunity.
6:55But their ego can't let them make the decision for the good opportunity. And they go to the, they chase the position. And three years later, they come back to me and say, it never went anywhere. You were right. And I said, I'm not trying to be right, buddy. It's trying to help you out. Right opportunity. Because if you're in the opportunity with a lower level position, But you're in a great company three years from now. You're going to be in a higher level position if you prove yourself, right? And you're going to be working around great people. It's a great opportunity, a real positive outcome monetarily and experience-wise.
7:30We talk a lot in Pavilion about the average tenure for a B2B CRO being 17 months, a lot of job instability, sort of to the point of the opportunity versus the title. When you look and reflect on your success and the lineage of the tree, the nature versus nurture question, to what extent is it the individual's capability perhaps coming from the training that you helped develop and the tutelage and the mentorship that you develop when you're a PTC? And to what extent is it, listen, the Warren Buffett phrase of a management team in a bad company, the reputation of the company is left intact. When you think about like the quality of the opportunity, the quality of the company versus the person themselves, how do you think about where the greater impact and greater resonance is?
8:18It's all about the person, right? I mean, when you're recruiting, I always think that there's four categories. There's the person's skills, there's the person's knowledge, there's the person's experience or their track record, their, you know, their resonate. And then there's the characteristics. And I've always hired on characteristics. So I'll take someone with less experience, but great characteristics. One is super intelligent, so they can pick up all the knowledge I'm going to try to give them and train them with. They're super driven, super competitive. I call it a PhD, you know, persistence, heart and desire.
8:51Those people are going to pick up the skills because the skills take a long time to pick up. You know, it's repetition after repetition after repetition. And if you're not driven, you're not going to pick up those skills. so I'll always take somebody with those characteristics and they're coachable and adaptable meaning you know in startups you always see it where one year you're one company the next year a completely different company different messaging different products different capabilities different competition different personas you're trying to call on and the people that are not adaptable they get left behind and they look like a dinosaur so I always think it's about the characteristics and and those types of people you can because they're so driven you can push them into certain areas and if you see their potential that they don't see you can push them and help them it's not just them doing it on their own help them get to places they couldn't get to before didn't even see themselves there and then when they get there they're not leaving you You got somebody for life.
9:55When you look at the notable CROs that have come out of this lineage, they've all kind of made a bunch of their bets now, right? They're in seat. They're operating. You've got Chris at Cognition. You've got Dali at OpenAI. Carlos is happy at Harness. And so how does the next AI company that is growing at an astronomical rate, how do they go about getting the PTC approach in place where you've got these SVPs or second in commands that are very happy? You know, Brian is very happy working with Dolly. So he doesn't want to leave Gobi a CRO. He knows this is his best bet. So now what happens? How do these next bunch of companies get this sort of approach to go to market if all these leaders are already in seat?
10:46Yeah, they're not all in Cito. There's some that are like looking around. And to your point, it's got to be the people, not only like to say the Cedric Pesce of the world, who's, you know, at MongoDB for 10 years, but there's people underneath him that are fully capable of taking these CRO positions. And there's also people that were running, you know, North America or Europe or even, let's say, the East for a company that went from like zero to three or four billion. And the movie that that person saw underneath someone like a Cedric Pesce, I mean, those people could easily take the CRO job. The thing is, let's back up.
11:27Our sales industry has been completely diluted. You know, if you think back just 20 years, you could probably count 100 or 200 enterprise software sales companies. Now there's thousands. There's a couple hundred in a 10-square block area of San Francisco. So I've seen it where there's CROs that I know that were running customer support, never carried a bag. CRO. People that were running rebops never carried a bag. CRO. Oh, so these two, by the way, these two are those two who think that RevOps people can become CROs. If you want to know why some companies are now going to make it and some aren't, I can just say, go look at the top, go look at the leader.
12:10Do you think not having carried it back is a disqualifier to be a CRO? A hundred percent. Oh, interesting. How can I possibly go into a sales call with a sales rep and follow their sales process through this account that they're calling on and understand the subtleties, the idiosyncrasies of what they're going through and why they can't do certain things or can do other things? you just can't understand it if you haven't been so intimate in sales just don't understand how you can do that the only thing i would push back on that is that if the ceo i'm just taking my case where my cro was our rev ops leader uh and when he stepped into it he ran account management first and i told him similarly i was like look i've carried a bag you haven't but let's do this together i'm going to have you close individual deals to go through this because you have to lead by example and he was like okay totally fine and the first 10 deals he did completely by himself to really work through that you think that's a situation or no you need to be an ic and move up through management to become a cro the way that i look at it any really good sales rep or sales leader is going to look at the person that they're going to work for and they're going to ask themselves two questions one is this person going anywhere and two am i going to learn anything from this person?
13:37If the answer is no, they're not going anywhere and no, I'm not going to learn anything from them or either or I'm out. I'm not going to work for that person. I think this also matters more and more as you grow up in complexity, right? So if you think of mid-market and enterprise, I think it's impossible for a person to be a CRO of those sort of motions without having actually been an IC, not just close deals, AJ, but like had it. I agree with that. right like get kicked in the face like lose a year because that deal that you were relying on and that you over i think in that stone fell apart like you have to just learn the lessons over five six seven year period transactional sales is different than the enterprise sales it's like you're hiring kids like they don't even know what to look for you process oriented yeah yeah it's also the same when you move somebody from a sale where it's a single functional organization structure straight up and down and then you move them to okay go call on a major account where they have to go into multiple disciplines in the account, multiple stakeholders, each with their separate decision criteria, and you have to herd cats.
14:41Then it goes to the next level. Okay, I got to call on the GEs of the world where I have divisional CIOs and then I have corporate CIOs, and I have to get a common decision criteria in order to jam this deal through. The amount of politics and experience you have to have to be able to do that versus a low-level transactional sale, the skill set is way beyond what most people do. Would you say that's true, though, even though enterprises are more willing, the sales cycles have been shortened at the enterprise when it comes to AI. It really feels like they're like, look, the demand has changed. We have to be doing something with this.
15:17We will shortcut procurement. We will shortcut our legal and red tape to do these things. It does feel like that's changed a little bit where these enterprise-level deals are, I don't say becoming easier to sell, but they are reversing where companies are more willing to just figure it out without having to multi-thread at the level we used to see previously. I think, AJ, I think that's because we're in the early stages of AI and there is like what you said, a great demand. So these people, when you talk to them at these different startups that are taking off and doing 1 million the first year and 100 million the second year or more, those reps are just fulfilling demand.
15:55Yeah, they're taking orders, order takers. Yes, they're not creating demand. So when you really talk to the VPs or the CEO and you say, tell me about your sales force. Well, John, I actually don't know who's good and who's bad because everybody's selling something. So I know I'm going to get to the point where they actually have to create demand because the competition is going to start to run into each other. Then I then I'll know who's good and who's bad. Like right now, the deals between Anthropic and OpenAI are very competitive. So like the customer, if you're JP Morgan, you're going to spend on AI.
16:30You're going to spend a bunch of money with, you might do business with both, but with one, you're going to have an outsized spend. Winning that is actually very, very competitive, which is why OpenAI has a great CRO and Anthropic has a great, like it's actually more competitive now than it was a year ago. And it's becoming more and more competitive. So this sort of thing matters. Do you, related to that exact point, I'm curious what this group thinks, obviously, John, especially you. So I was with Anthropic last week, or, you know, one of the people that runs a big chunk of business for them.
17:01And they were talking about how they have a floor and a cap on their commission plans. And they also have constrained hiring plan. And they're worried, I think a year ago or a year and a half ago, when OpenAI was putting out, what was the short video thing, Sona, or whatever it is. and it didn't feel like OpenAI was as focused on the enterprise. I don't think Anthropic was as worried, but now as they look ahead to their IPO, OpenAI is hiring very aggressively and does not have any cap on commission plans and people can make as much money as however many orders they can take. How do you feel about a sales organization that has capped commissions, I guess is one of the way to ask that question.
17:37I don't like it. But maybe right now in these early stages, they have to do something because, like I said, it's a land grab and they don't actually know who's good and who's bad. And they're trying to, you know, fix their gross margins. I know one seller whose million-dollar equity grant, Adanthropid, became worth$50 million in two years. So you don't need commissions then, right? Like it used to take multiple CRO exits that were successful to make$50 million. You used to need the commissions to go pay the mortgage. Now you take the stock and you buy a much bigger house. And they're doing tenders.
18:16So you actually like liquid more than you were before. So it's not just on paper, like you can actually sell some of it and make some money. So Asad, do you think that's an irrelevant distinction in terms of the commission plans? I think if your growth is as astronomical as Anthropics was during those two years, you can get away without commissions. And the minute you hit some sort of like stable growth, you need commissions. Why would a salesperson come work for you? Not that cool, right? Like A salesperson needs commissions to be able to make the total income and for it to make sense for them.
18:46And then it becomes an immediate counter position for your competitor to take. Like, hey, we're both comparable companies. Just come work here. We take care of you. We treat you with respect. We give you what you deserve rather than force you to have no commissions. If your stock equity cannot rise at that rate, then you have no justification for no commissions. It will bite you. John, I've been thinking about age a lot. So we're talking about, you know, the low tenure of CROs. and I've been thinking, what's the right point in your career to decide to become a CRO? Because the minute you start gaining some sort of momentum, right, like you enter your 30s and you start getting these opportunities presented to yourself, and you see some people can take that opportunity, go kill it and have a wonderful career, but I sometimes meet people who I feel like you just took it a little bit too early.
19:34You could have been a great CRO, but you just took it a bit early. You weren't well-rounded enough. You didn't pick the right company. You didn't have enough quality opportunities to look at. What's your advice to people when they come to you and they say, hey, I've started getting these CRO opportunities. When do you think is the right time? How does a person go about making that decision? Well, you can tell them that they're not ready, but you have to be intimate with them and their capabilities. Even Dolly, I had him on my podcast and he admitted on the podcast how he pushed me one time hard.
20:06like he wanted a position at the next level. And I told him, I'm not going to do that to you because you're not ready. And when you're not ready, you're going to get in that position. You're going to fail. Your ego is not going to be able to take it. You're going to blame it on me or somebody else and not yourself. Eventually, you'll come to the conclusion that you weren't ready for it. And it's going to hurt you in your career. And I don't think anybody can just say that to anyone else. They have to be fairly intimate with their skills and capabilities and whether or not they're really ready for the job.
20:38What do you think makes somebody ready for the job? Like in that situation, what was, if there's a consistent set of qualities that are the gap between those two levels? Well, I'm a fundamentalist, so I always go back to, you know, do you really know how to recruit? You know, do you know how to interview and do you know how to sell candidates? And can you recruit the types of people that want to work for you, right? Right. That's big because, you know, you need A players to recruit A players. If B's are recruiting C's, you're not going anywhere. And then you need the person to understand how to truly onboard these people and coach them.
21:21So can they assess? So you might ask him questions about people that work for them now. Okay, explain to me why you think Joe as a sales rep is not making it right now. Now tell me what strengths and weaknesses he has, meaning what skills is he lacking or what knowledge do they lack? So to me, I always think about sports and I think about plays. And in any play, a great coach is only looking at the player saying, you know, does Sam, he failed at that play. Why did he fail? did he not know what to do meaning he didn't have the knowledge or did he know what to do but he couldn't execute it because he didn't have the skills and that's the same for really good sales leaders can look at a person and understand in different steps of the sales process specifically what knowledge they're supposed to have and what skill they're supposed to have to execute that play and assess them that quickly.
22:19When you hear, why did Sam not make that, oh, he doesn't have grid or they make up some characteristic thing that Sam is lacking. I'm like, you just don't know what you're talking about right now. And then can they lead? Do people want to follow them? When some people say, we're going through that wall and we're going through that door right now and they turn and gut walk, everybody's behind them. And there's other people when they say, hey, we're turning, we're going through that wall right now. They turn around and only two people are moving. You're going through that wall. Yeah, you are, not me.
22:56John, to the point you made earlier, around 250 enterprises previously, and now there's thousands. So there's thousands of CROs, but there's also thousands of CEOs. And so everything you're saying around the CRO of like how they have to recruit, how do you talk to CROs about how to evaluate companies and the CEOs, which probably is just as important as some of the things that you're discussing. Really difficult because there's different types of CEOs in the startup world, right? There's the CEOs that think that they're way smarter than anybody else. You know, they were really smart through college and everybody told them how smart they were.
23:33Then they went into business and everybody told them how smart they were. You don't belong here. You need to get out of here and start your own company. They start their own company. They got an idea. VCs are throwing 50, 100 million dollars at them. Now they think they know everything. The smartest guy in the room, they think they know sales. And they're also actually pissed off that they got to pay salespeople three or four hundred thousand dollars at OTE to sell their product because they think everybody can sell my baby. And we're going to sell my baby right now to everybody, which is also a problem because in the early days of a startup, maybe not with these AI companies right now, but you typically couldn't go straight to the Morgan Stanley's of the world, right?
24:15You had to figure out what's my ICP, what's my competitive advantage, what pains do I solve, who am I going to sell to, put together a really good ICP and go sell to those companies, go down that bowling alley and then start to expand from there. So sometimes they can ruin companies, especially if the CRO is not strong enough to say, that's the wrong way to do it and let me tell you the reasons why. So then they I can actually almost kill their own company, the CEOs. And I've seen the movie before. So AJ, it's really, I think if they don't, if the CRO is not strong enough. The second thing I see with a lot of first time CROs is they, they know they have a C level title, but they don't see themselves on the same level as a CEO.
25:02Yeah. So I, so then they'll come to me and say, well, this isn't working and that's not working. I said, well, did you tell the CEO? No. Why not? well that means and i have to coach them and say look he or she's the ceo you're the cro you have a fiduciary responsibility tell the ceo specifically what you think is wrong with the business and have a solution for what they need to correct now you get to discuss that partner to partner on business terms and at the end of the day the ceo gets to make the decision and you got to live with it. But if you don't bring it to them, that's a problem. This is advice that is very different to a lot of very common advice.
25:45Sam, you've heard, like, I think Jason Lemkin even said this on one of our podcasts where, or I think he was with Kyle, where he said, a CRO talking about the product just doesn't work. Like, as soon as you start talking about the product, we start thinking that you're scared, you're weak. It shows weakness, don't do it. There's very controlled settings in which a CRO should be bringing up product deficiencies. Whereas on the other side, like it's the thing, you're the tip of the spear, you're in market, you're seeing what's resonating, what's not. If you see a gap that we can address from a product perspective, and we take that insight to the product team and they can fix it, we can unlock velocity.
26:21But a lot of the advice in the market is don't do that. Very rarely should you be able to do that. Well, I'm not saying that you have to talk about the product, just there's something else wrong in the company. But, you know, To your point, having a CRO blame revenue problem on the product is a non-starter. But there's a whole bunch of other go-to-market issues that can be affected by if you can get the rest of the company to come along. Those are the types of issues I'm mainly talking about. And is that because the product is always going to have gaps and holes? And so pointing those out is like just pointing out the fact that the star is blue.
26:55Like, yes, we will have holes and we will plug them as we go forward. You have to, first of all, as a CRO, you have to be a business owner. You can't come across like every time I bring something up, it's always about sales. It has to be because you're a C-level, you have a C-level position, and you're talking from the standpoint of a business owner. That resonates a lot more than just always complaining about how the company is affecting sales. This episode of Topline is brought to you by Compound Growth Marketing. The way your customers buy has shifted. Before they ever reach a rep, they're asking an LLM who to trust, who to shortlist, and why.
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28:12Mention Pavilion. AJ, what do you think about compound growth marketing and why do you love them? Sam, I was just looking at our last set of texts from, and we have lots of texts. We text, we text a lot. How many of those texts are about challenges and tribulations around demand gen and marketing and figuring out how marketing works in today's world? I mean, a very large percentage. All of them. Very large percentage. Because we have one-dimensional conversations.
28:40When we text about compound growth marketing, we're often texting about demand gen. That's true. Yes. My point is, Sam, that this is top of mind of every business leader out there and trying to solve this problem. I get it 100 % all in on compound growth marketing. I would say that AEO leads are super high quality. It's way better than like SEO leads used to be. Because they're so persuasive. That's why you got to check out compoundgrowthmarketing.com. Thanks, compound growth marketing. I want to talk to you about something I've been really excited about lately, everybody. It's called Computer, and it's by DevRev.
29:18Listen, if you work in GTM, you know what it's like. You're doing a million things. You're running a dozen deals, and you have to remember every single detail and who can do that, what the customer said, what you promised, what needs to happen next. Things slipped, follow-up gets missed, a deal goes quiet, and you know what happens then? You lose money. Computer by DevRev is an AI teammate that fixes that. Computer uses something called shared memory. It just remembers everything across all of your different stuff, you know, Granola, Slack, Salesforce, whatever. It remembers it so that nothing falls through the cracks and you know exactly where to go and you know where the account stands and you close more deals and you make more money.
29:53And that's what we're all in the business of here in GTM is making more money. Take a look at computer.io forward slash top line. That's computer.io forward slash top line. AJ, how do you keep track of all of the different stuff with all the different pieces and everything going hither and yon? Well, Sam, I have a call with Apollo from DevRev next week to do exactly that. So that's great. You've been thinking about it so much that I was like, you know what? I'm doing it. And so we keep talking about it. And here we are. So I'm going to figure this out next week, Sam. I love it. Asid, how do you keep track of all the different deals?
30:29I tend to use post-its.
30:35Well, again, just one more example of do the opposite of whatever Asid says. We don't want to, we're not in the Post-it world, people. We're in the computer by devrefs world. Check it out. The website that you need to go to to avoid being us, it is computer.io forward slash topline, computer.io forward slash topline. Thank you. This episode of Topline is brought to you by Pavilion. I want to tell you about Pavilion Gold. It's so exciting. Pavilion Gold is an invitation-only community for senior go-to-market leaders at many of the world's leading B2B companies, CROs, CMOs, presidents, and executives navigating scale growth and transformation in real time.
31:21Pavilion Gold is about a year and a half old, but our first group of 24 Pavilion Gold members came up for renewal on October 1st. I want to ask Asit, how many of those 24 people renewed their Pavilion Gold membership, which by the way is not insignificant. It is an investment. I think I did my talk right before, and so I would imagine close to 100 % after this only on stage. Your talk. I was also there, Asad. Your talk. It was around. It was around. I would imagine, just from the conversations I've actually had with people that are in it, I would imagine this has one of the highest renewal rates you've ever seen in your lives.
32:00100%. It is. 24. It is 100%. 24 out of 24 people. 100%. 100%. And then there's a few people that came up for renewal through October and into November. Again, so far, the renewal rate is 100%. That's crazy. And in fact, my favorite, so here's one of the, Matt Thompson was the president of this cyber company called SoCure. And he got recruited away to be CEO of a new company called Transmit Security. we get an email from him it says may every day be day one that's the subject on his first day as ceo of this new company we don't normally let ceos join but we're not going to kick you out if you were previously an operator and then you get promoted to ceo and so the first thing he did literally this is not a joke the first thing he did was re-sign up for pavilion gold and he gave his old uh membership to uh his cmo at the departing company let's talk about this so for a second because I, and this is no BS.
33:01I think Pavilion Gold is awesome. Like legitimately the best conversations I've ever had as a part of a community member at Pavilion have happened at Pavilion Gold events. The dinner in New York was amazing. When are you going to let CEOs in and why can't we be in? Seriously, I'm honestly frustrated about this. We're, AJ, you are well served, sir. You are well served. I know. You got Pablo. I know. You got Insight. I know. You got Hubbot Ventures. you're being whined you're being i'm asking for the world though i'm asking you are you were an early investor in spacex you're doing just fine you don't need us you know who needs us operators operators need us so the answer is we tried a ceo group and sadly besides aj and asid who i love besides those two people i can't say that it was the top brass of ceos that we were getting we were getting a lot of rev ops consulting firms trying to sell into the go-to-market community and that's because, you know, we're not pavilions for operators.
34:02Yeah, we're a go-to-market community. So I really liked that in the event that I attended, I even felt for myself that we were able to be far more open because you trust, it was a smaller room of people that had come in. The bar is higher. Yeah, the bar is much higher. Trusting that we're not going to let this information out. We're going to use it for ourselves, but we're not just going to like, you know, quote this person on social media said this. And so it actually allows real conversations. And that's very rare. It's very hard to have real conversations. It's our highest performing program.
34:35It's really, really powerful. If you're interested, please reach out to me. You can email me, sam at joinpavilion.com. You have to report to the CEO and you have to be either super fast growing AI or at 100 million plus. But otherwise, we'd love to talk to you. Thanks, everybody. We're in this shift now where you've got these AI companies that have really shown us a whole new way of building, the speed at which they are scaling, the speed at which they're shipping product. Like so much has changed even in these early years of platform shift. And one of the questions when we mentioned to our group, Slack group of top liners that we're having you on, there was a lot of excitement.
35:17And one of the questions that came up is, what changes from a methodology perspective now that you've got this dynamic where buyers have so much more information before they enter a call. Like this shift has been happening for some time. You know, in the SaaS era, you could go to the website and do a bunch of research, read a bunch of reports, etc. But now the level of information you can get about a particular company before talking to them is orders of magnitude more. How do we adjust from a sales perspective or from a methodology perspective to address this sort of shift in market dynamics?
35:53Well, it's the same. I mean, the buyer can learn a lot more about me and my product, and I can learn a lot more about the buyer and their pains and issues, right? So I think it's AI right now just helps with research. And I think it makes the really good sales reps better, and it makes the lazy sales reps lazier. Because the lazy sales reps show up by typing in, I'm going to go call an XYZ company, and here's the person I'm calling on. Here's the use case. Tell me what my opening point of view should be. And then the customers heard that point of view three times already because that's all the lazy salesperson did.
36:29But the really great salesperson is going to use it to discover their business risks, their threats, the competition, their persona, how they're measured, the competition, all of that stuff they're going to figure out before they go in. They're certainly going to have an opening point of view, but then they're going to differentiate themselves because of their characteristics. They're truly curious. They're truly asking the right discovery questions. They're listening. You know, those types of things that differentiate yourself. So you can use AI to do the research just like a buyer can, but at the end of the day, it's always about how do I differentiate myself from the competition as a salesperson.
37:12One of your predictions was that a lot of companies are going to use AI to A, understand what customers want to hear, and then just like flood the market with all this information about themselves positioned against what customers are looking for in a way that almost makes every company in that category look the same. Everybody kind of looks a certain way. And what it's going to do is it's going to make the job of the seller even more important. So I think at the time, there was this argument of sales will go away. You know, every time there's a platform ship, people make that argument. And yours was actually, no, the way that this is going to confuse the customer will increase the need of the salesperson, the really good salespeople to create differentiation.
37:53How do you feel about that prediction of yours a few years in? I think it's still right. I mean, I don't think anything's changed from a sales methodology. I don't think anything's changed from a qualification methodology. All it's changed is I can do a lot more research on the buyer and they can do a lot more research on me. What you said about the laziness is just, it's so true. But I think we're seeing this even more at the management level where you can just have the gong read out and say, here's the coaching. It doesn't feel like we're doing the work to actually listen to those calls and really, really take what the buyer's working and work through that on a weekly basis.
38:32Like, you know, you can do two to three call coaching sessions a week and it can take you 10 minutes now because you're listening at two and a half X. And I have no issue with listening at a faster, but it also just feels like the amount of velocity that we're just trying to like check off the things that we're doing, especially if we're not in person or in office, is at an all time high, unfortunately. So like what you're saying definitely resonates and I feel like it's at all levels of the business if it's not built foundationally correct. It does drive me a little crazy, these conversational intelligence tools, because all they're doing is verifying that something was said, but there's no true qualification.
39:12Okay, so you come to me and you say, stand up in front of me in front of a QBR and you say, I got a$2 million deal, John. I go, great. You got a champion? You go, yeah. What do you think I'm going to do next? I'm going to ask you 24 questions to see if you truly have a champion coach. You're going to sweat pouring down your forehead by the time I get done with you. But by the end, I'm going to know if you have a coach or a champion, and I'm going to know whether or not what the next steps of that deal should be. That's not happening with conversational intelligence. They're just giving you some proposed insights from what they heard, but who said it?
39:48Was that a coach? Was it a champion? Was it the gatekeeper? Was it recommender? Was it a user buyer? Was it the economic buyer? Who was it? And is that person an enemy? Because I've been on my fair share of sales calls where we're driving. Hey, who are we going to go see? We're going to go see my champion. Oh, we're going to go see your champion? Yes. Okay, great. How long have you been calling on the account? Six months. I go in there in five minutes. I know the guy's not a champion, right? or I go into the account and I figure out this is a fox in sheep's clothing. This person's wrapping my sales rep around their finger.
40:25They're the enemy. They're telling the sales guy anything that he wants to hear, they're sucking in all the information and giving it to the competition and they're making like they're going to take the person to the pot of gold. So these conversational listening tools and some of these other AI tools right now, the way they're built, a stupid clawed wrapper around the tool, it's meaningless. It's garbage. It's like - Tell us how you really feel. Laziness. Do you think anything's changed? I was doing, you know, there's that book, The Jolt Effect that came out. You know, it used to be maybe in 2014, they estimated there were five people involved in an enterprise purchasing decision.
41:02And now they estimate it's 13, sometimes as high as 22 people. So it feels like, but you can say that's BS. It feels like there's more people involved in purchasing decisions. And I always wonder if some of the phrasing, I think the ideas in Medic are obviously great, but thinking of it as one economic buyer sometimes feels like it distracts or confuses the salesperson from building enough organizational consensus. Or do you think it's just the same as it's always been? They got to find the champion, they got to find the buyer. Yeah, there's more people, but there's always one person whose budget you're tapping into and that's the person you got to find.
41:40Yeah. And you have to get to that person, Sam. So you need a champion to help you get there. Sometimes even the person that says they have the budget and you say, well, Sam, you know, Hey, have you actually ever bought anything before for$2 million? Okay. So why don't we know anybody in and around here that's bought something for$2 million? Yeah. AJ just bought something for$2 million. Why don't we go over and talk to AJ and find out what the paper process is and all the different people that were involved in that approval process. Right. So to your point, Sam, I think it's all about, you know, not checking boxes, but understanding like how are things done at this company is my champion, who's a good technical champion, but may not be the right business or financial champion to get this deal through.
42:32So they got me to the decision that they want to buy my product, But now there's a whole nother process and other champions. They got to help me get this thing out the door. Sounds like you've talked to Sam about his slack bill that he gets. He's spent$2 million on something. Oh, AJ, that hurts. I need to learn more about that later. I find that there is this shift that's happened over the last couple of years. If I think back to PTC, I've interacted with a lot of the sellers, a lot of the leaders that were part of that lineage. And one of the things that always stood out to me is that they had this discipline around the methodology.
43:16They had this clarity of thought around how to qualify a deal, how to move a deal forward, when to move it, when not to move it, all of those things. but they also seem to have been given the trust that in an enterprise deal there's going to be a bunch of game time decisions that I need to make and they had the skills and knowledge but also were trusted to use their creativity and their acumen and their insight of that situation to make the right calls and they loved that job because they didn't feel overly stifled they felt like there was a boundary within which they got to play but within that they got to be themselves and they got to discover parts of their own style and approach.
43:59And there were very different sorts of sellers that came out of that. Now, when you look at the other side, you see this huge shift towards trying to turn salespeople into these coin-operated machines. Everything is overly scripted. The amount of creativity that they're given is very limited. And all of this is in pursuit of predictability. If we want predictability, then we need to be very formulaic. we need to do the same thing over and over again. And on average, we'll win. And this is what it is. And it's really dulled, in my opinion, the craft of sales and the life of a salesperson. What are your thoughts on this dynamic?
44:38Have you seen this play out? I haven't really seen it, but I don't believe in it. I believe, you know, that there's an art and a science to selling and you have to be yourself. And, you know, just like any good sport. There's this knowledge and the skill to pull a playoff, but there's also the art of it, how you catch a ball, how you take a snapshot in hockey. Those things, there's a part art to that. Everybody's not going to be able to do it the same. And in sales, you have to be yourself. You have to be authentic or people can feel like you're not authentic. And in sales, you have to be here in the moment to be able to listen to be able to have intuition and if you're trying to be somebody else or you're not prepared it's very difficult to be in the customer conversation and be yourself be authentic be here be in the moment and that's what i find is when people good sales people sometimes they take a long time to just let go and not be somebody else just be yourself and just sit there listen to what the customer says stop thinking about what you're going to ask or what you're going to say because if you're really listening if you're really in a customer conversation you'll know what to say because you're reacting to what the person said you know you're in flow state just don't believe in that whole formulaic thing to try to say like you know tom brady should throw the ball the same way as you know holmes and And some of these other guys, Mahomes and some of these other guys, it just doesn't make any sense.
46:11When you sit down with like an amazing enterprise seller and you ask them to walk you through a deal that they close, the proudest deal that they have, you can tell that that person was in flow state over the course of a 12-month period on this deal. Like it is really hard to keep an enterprise deal alive over 12 months. You've got like dozens of people on both sides. You need to keep them engaged, incited, moving forward. You need to do the science, but there's also like the personalities and the art of it all. And these were people that were in flow state to close that deal. And then when you start looking at these teams where everything is so formulate, how do you find flow state when you're being stifled like that?
46:46It's impossible. Well, those are also the those are the probably the teams, Asad, to your point, that are more focused on hiring rev ops people to be the CRO versus the people. I was struck by your answer, John, because it wasn't about forecasting and it wasn't about predictability. when I asked you what are the key skills that separate the good from the great, you said recruiting, talent acquisition, and leadership. And it almost feels like your point is forecasting or hitting the quarter is really just aggregating all of these individual conversations I have with my team, leading them, coaching them, mentoring them.
47:23I can figure out the forecast, but if I have the wrong people and I'm not coaching them the right way, then nothing's gonna matter. Is that, because I think there's a bunch of people that don't think that. Yeah, I, you know, I, I'm not saying that you should be average, but if you, if you think about it, if you hire all B's and C's and do everything else perfect, you onboard perfect, you train perfect, you develop perfect, you're not going to the championship. But if I hire all A's and I did everything else average and I'm not advocating it should be average, you're going to the championship. Those people help you find a way.
47:58It sounds like you're probably pretty bearish then on, we've had a couple CEOs on that are automating some pieces of this, including, we'll say one mind, which is Avatar sales. And Amanda has stated directly that she doesn't believe sales will exist in 12 to 24 months. My opinion on that has evolved, to be fair. I know. We got in a big argument about this, but it's bogus. Like I said earlier, good luck selling to a multi-department, multi-divisional company. And for$10,$15,$30 million, good luck selling a deal like that with Mindy. Yeah. Clearly he's familiar with one mind. Clearly he is. One thing that I think people don't realize about your background, I think when they hear John McMahon, they hear PTC, they think enterprise sales, rightfully so, right?
48:59But I was talking to Mark Roberge, and he credits his time spent with you as an advisor at HubSpot as really, really formative in his development as a CRO. And I would say when it comes to the more transactional side of sales, probably the greatest CRO we've had over there, one of the greatest we've had. And I didn't know this. I didn't know you were a HubSpot advisor and worked that closely with him. And I haven't heard you talk about SMB sales all that much. And so maybe we spend a few minutes there. Was that the first time you were helping somebody on that side of the complexity spectrum? Well, I got in there.
49:43Brian Halligan, the CEO, used to work for me for nine years at PTC. So, yeah, we were good friends. And then when he started, you know, he said, Mark may need, you know, some help. So can you help him out? And that's what I did. And Mark is just super smart guy. So smart. How hard was it for you to adjust to SMB sales and the dynamics? Because they're so different. That's actually a little bit more formulaic and things move so quickly and the buyers are less astute. Like how was your adjustment period to be able to actually give advice to him? Or as a fundamentalist, it all was just the fundamentals.
50:19Get this right and it'll work in this side as well as that side. Well, it's always your approach, no matter whether it's enterprise, you know, you go from one enterprise company to another enterprise company. It doesn't matter if it's SMB or enterprise, you know, it can't be cookie cutter. Too many people think things are cookie cutter. And if that was the case, God, life would be pretty freaking boring, right? So, you know, certainly there's a Venn diagram. If you move from one company to another company, there's certain commonalities in the way you're going to do certain things. But there's all these other areas that are outside the main circle that are simply different for this company.
51:00And that's where you have to go and dig in when you're going and working with a new enterprise company or an SMB company. What's different here? What do I have to learn in order to help these people, right? The world of sales is, it's not cookie cutter, it's nuanced, right? And the go-to-market is then nuanced, right? And for those guys like with PLG, it might be more on a micro scale than a macro scale, but you still have to deliver value. You have to build a really easy on-ramp. You have to get the customer to test your product. You have to track the product and usage metrics, right? You have to find a way to differentiate your product.
51:39that's really no different than enterprise sales but it's truly understanding like how do i do that and do it effectively for their buyer right how does that customer want to buy was that the main difference with hubspot was it was the same things but just compressed in terms of speed and done in some cases not for through human interaction but through like product and web experiences like Was that the core difference? Well, they also, they had, you know, hundreds and hundreds of people that they hired out of like MIT, Harvard, you know, Northeastern, all the BU, BC, all the schools there. And they were all banging the phones, right?
52:19So, you know, the sales process might've been shorter. So the cycle time might've been, you know, 10 days instead of 10 months. But the types of things that you had to do with the customer was still no different. this this was interesting in terms of the educational background i'm working with one of sequoia's companies right now and they've gone from nothing to a couple hundred million in obviously five seconds and all of their sellers are from like these ivy lead schools like harvard and mit and stanford and and obviously the company is doing well but i look back to the teams that you built and the characters were far more interesting it wasn't like you were over indexing on like this one signal of, you know, caliber, like which school did you go to?
53:04There were some really interesting characters that you had hired all from really unconventional backgrounds. And you'd kind of seen their characteristics and thought that this could make sense. But you hadn't indexed towards education as much. Thoughts on that? It was all about personal characteristics. Like I said before, for me, it's all about their their intelligence you know their their drive their coachability their adaptability and their integrity if i could get those five things that person's going somewhere because the number one when you when you look back on any time that somebody didn't make it and that you did hire it never comes down to something they didn't know it's really like it was a characteristic flaw.
53:49We can say, oh my God, we hired this guy. We made a big mistake. And it's always a character flaw. They showed up great in the interview, but they're really lazy. They're not really driven, or they're really not as smart as you thought they were. So you have to figure out, are they truly smart, out of the womb smart? Are they truly driven? What's the toughest thing they've ever done in their entire life? Walk me through that. What's the most competitive situation you ever been in your whole life? Walk me through that, right? Walk me through how you rebounded from something horrible that happened in your life.
54:24Now you can't ask those questions and just let them give you one answer. You have to dig in deep. And when you dig in deep, you find out their character. I've had many people crying in my office when they relive what they went through in their life. But what I'm looking for is, okay, how did you get back on your feet? How did you now start to succeed i'm looking for that over somebody that was a brainiac and went to went to harvard or mit but they don't really they just were born that way but they don't have the drive because i've had guys that scored have scored you know perfect on their sats and never made it in 2007 when i started my sales career those were the exact questions that were asked i started a company called meltwater it was very cold call sales all the way through and but the question of like passions and talk about challenges very applicable then today it feels like well maybe not recently but we've gotten a little soft like we're afraid to ask these really tough questions in this process no you're not obviously not but this is this is clearly where the world's changed quite a bit just in the last six months so this this type of sales dna and driven is coming back uh two quick things one do you count i guess brian halligan definitely counts as your like coaching tree right so he does does mark roberge count in there too if you want well i'm saying that because he's on my board and so i'm counting myself then in the john mcmahon i'm taking it i don't know you're gonna bring down the average
56:01but the second part which is the talking about roberge again for a second he didn't carry a bag before he was a CRO. No. And so he's a good example of kind of like, there's always outliers, right? But he did, like, what did you see in working with him? It was like, okay. Wasn't it the early days like he was the salesperson? Yeah, super smart. Well, first of all, Halligan had put him in the job. So I was going to go talk with him, but he's super smart, super coachable and adaptable. So as soon as I would coach him like, hey, Mark, you know, let me give you some advice. I think this is something that you need to do.
56:37And I'd reason with him why and educate him why, because a guy like that's going to ask you 20 questions before he really buys in. So you have to explain the why. And then here's how you should do it. But once he bought in, boom, the dude would change the next day. That's incredible. One of the things we were looking at was how in the SaaS era, after you stopped operating, you became a board advisor. Snowflake, HubSpot, obviously, a number of other companies. And a question that came from our audience was the importance of having a go-to-market expert at the board level. When you're a CRO and you're picking a company, how important is it that they either have a person in that seat or are willing to put a person in that seat with a go-to-market background for you to decide to pick that company?
57:29I don't know if I can say that it's so important when there are startups, But what I have seen from the best CEOs like Frank Slootman, David Acharya, some of those people that what they did with their board is they probably figured out. So I'm not putting words in their mouth. They probably figured out that they don't need to be the smartest guy in the room. And they don't know every discipline inside their company because they never were operators in finance, operators in development, operators in sales, operators in marketing. So then they would put some operator or former operator, you know, on the board for marketing, for sales, for finance and development.
58:15And I think it really helped him and the board help develop his people, you know. And I think that's the smartest way for CEOs to go as they build their companies. Get a true or former operator that's lived, especially at that stage of your company and has seen the scale. Have those people on the board. Speaking of the CEO role, you've taken that role a couple of times. Is it once or twice you've had the CEO role? Once. Once. And that was earlier, not earlier in your career, but a little while ago. Is it something that you've looked at as an opportunity or just once was enough and you're not interested in the role again?
58:55Because you must have been offered CEO roles left, right, and center. Oh, yeah, sure. Yeah. I got to the point where I figured, you know, in sales, no one's going to throw a fastball past me. No spitballs, no curveballs. I'm knocking the thing out of the park, right? So why not go to work every day and you're super confident? Pick a good opportunity and you can take it places. If I go into the CEO job, could I do the job? Yeah, I could do the job. Because I had to, even along the way, help coach a bunch of CEOs. But at some point, I made the decision, I'll just stay as a CRO. You know, when we think of your career, everybody thinks PTC.
59:34And obviously, PTC was amazing. And it started all of this. But you were CRO many times after that. You're actually one of the rare people. I always look at the greatest CRO is how many times were there CRO and you have the record, it's an exhausting job, right? Like there's only so many times you can do this job before you step away. When you look at the last, the second last and the last time you were CRO, how were you better then than when you were CRO at PTC? Because you chose to go deep, right? You're like, okay, this is my thing. I'm going to master it. What was different in you towards the end versus at PTC.
1:00:11Yeah, even, I mean, you learn a lot about your leadership style and how it has an effect on people, positively or negatively, and how you have to adjust as a person. And some of the mistakes that you probably made, like I can remember like at PTC, in the last part of it, we had this way of like, if you didn't make it as a sales rep, we would just like put a bullet in you. And I started to realize, you know, that's just wrong, right? I have to start holding my managers accountable for losing a sales rep. So if you lose a sales rep, you as the manager have to be held accountable. You recruited the person, right?
1:00:50Okay. So if you recruited them, you either can't train them or you can't lead them. So you either recruited the wrong person or you recruited the right person and you can't train and lead them. I want you to go down to the bathroom, I want you to look in the mirror and I want you to come back and tell me what you did wrong because we can't do this again. So whereas a lot of companies still look at, oh, the sales people did something wrong and it's the sales people fault. Why do you have all these leaders? That's their job. Their job is to recruit the best people, develop them so they can take your place.
1:01:21That's where you have a growth company so you can hopefully promote mostly from within. so that was like one lesson that i learned there was a bunch of other lessons that i learned as far as like even where i'm gonna hire you know so there's the average productivity per rep let's say that's 1.2 million in a company so then i don't have unlimited heads you know for the next year but i'm going to give quota to all the managers as if they are supposed to hire the heads now if some managers are consistently doing 1.4 million they're getting more heads if some other managers doing 1 million but the average is one too they're not getting any heads when they come to me and say hey john why am i getting any heads because you can't make the people that you have as productive as the average at the company so why would i give you any more heads oh that's interesting you start to look at your investments that you make in heads almost like a bond portfolio.
1:02:21Like, where am I going to put heads and when is this guy not going to make it and puts them over here? So you're really almost like an investment advisor as far as where you're putting your money or putting your heads. So you start to become a lot more strategic about the business and where you're spending time, where your people are spending time, where the leaders are spending time, you know, where are you going to make investments? What do you think's the biggest thing that's changed about sales over the last 20 years? Is sales still fundamentally the same or has the craft of sales changed in some important or material way that whereby the seller that is optimized for this environment would be a different kind of person than maybe 20 years ago?
1:03:07For the best salespeople, Sam, and the best sales leaders, I don't think much has really changed. you still have to go do all the hard work to really go do the really big deals and that's why some people separate themselves like there's one guy that worked for me he was at with me at blade logic he did the biggest deals at blade logic he went to bmc did the biggest deals at bmc he's been at two other companies since and he's done absolutely the biggest deals in those companies it's not magic takes him a long time but he he sticks to the fundamentals things haven't changed. You were talking about hiring as we want to keep our managers accountable.
1:03:48The other side of that is hiring salespeople is really hard, which is the worst salesperson can sometimes be quite good at interviewing. They have more practice, they have all the right characteristics, kind of slip through the cracks. And so having a perfect batting average seems to be, you know, too much of an expectation. But then having a 50-50 seems like, you know, now it's just coin to us. That doesn't seem like good leadership. What sort of batting average are you willing to, like, what does good look like? If I'm making 10 hires, how many of them have to work out and be great hires? And how many, like, if out of every 10, one is in a fit, that's okay?
1:04:25Like, what does that look like? I'd like to say 10 out of 10. If I don't say 10 out of 10, you're not going to think there's something wrong, right? Aside from it, nine out of 10 would be good. But it's your, you know, you have to train your managers, especially your first line managers that are probably seeing the candidate before anyone else. You have to train them really well on what to look for. How do you read a resume? What questions do you ask? How do you uncover their strengths and their weaknesses and what they did in these jobs? Were they running from one job? running away from a job or they running towards an opportunity.
1:05:06There's a whole bunch of things where you just train and train and train. There's no training done on interviewing. Like if you look at the average frontline manager and say how much training were you given on how to interview a salesperson, it's negligible, like almost nothing. Well, if you were, you did tons and tons of training on recruiting and interviewing. And not only recruiting and interviewing, but then there's the selling part. so you tell your managers okay get up in front of us sell the opportunity of why i should work here that's interesting yeah because a lot of times you find your manager can't sell the opportunity don't sell so then the way i know is sometimes it's falling on my desk hey john we got this really good candidate you know can you sell can you sell them on the opportunity we just had to have this conversation last week with one of our clients we had to reach out and be like hey your VP of sales cannot sell this opportunity.
1:05:59This is a disaster. Like, no rep wants to work for this person. Like, this is an issue now. Like, you have to address it. But to me, it's like, what could be more important than the people you recruit on your team? What could be? But he's very good at this other thing. It's like, well, it doesn't matter. He's not good at the main thing. I did this so many times. Like, especially did it a lot to Dave in a chair. He'd allocate me a certain amount of heads and fill the heads. I would have guys start. the next quarter on the first day of the quarter, right? He'd say you have like 10 heads for next quarter.
1:06:34They'd start on that first day. Because I wasn't waiting for the quarter to start to recruit. Then I'd say to Dave, hey, Dave, I have this guy I want you to interview. John, what are you talking about? I've told you you don't have any more heads. Okay, Dave, I know I don't have any more heads, but here's what's going to happen. You're going to interview him, and then you're going to tell me whether or not I got any more heads. he'd interview the guy come out of the meeting and go we gotta hire this guy no so you know who are we gonna get rid of now Dave had to think through all the other departments like who are you gonna get rid of because we're hiring this person you also hired people for the next year like halfway into the previous year it was the thing that like most people don't understand is like if you're planning for next year hiring those people in January February and march is just ridiculous which is what 90 of the market does like you were hiring those people in two three you're up if you think about a productivity model there's ramp time it's productivity and then there's churn that ramp time is is like your enemy you're always trying to beat the clock right what we would do is lay out eight quarters and every time we finish a quarter you lay out the the next eight quarters now if we would beat the quarter let's just use conceptual numbers if we beat the quarter by a million then they would take half of the company and i take have to step on the gas ahead of the hiring plan because you always want to stay ahead of that hiring plan.
1:07:59Like, cause the worst that can happen. And this is, I've also seen this when I've advised some companies, the company misses by, let's say, let's make it again, conceptual. They miss, let's say their average productivity is 1.2 million. So they're doing a hundred thousand a month. They have 50 regions and they miss by 5 million. So you stand up and you say, okay, So, Asad, you're a first line manager. How late were you on recruiting? Oh, John, I was only a month late. Sam? Oh, John, I was only like a month and a half late. AJ? I was only like two months late. Okay. Now let's add that all up. Right.
1:08:34And aggregate it to the top where the CRO is. How much did he miss by it? Exactly how long it took you, you were delayed in hiring. That's how important it is. This all talks of the productivity, but what I've found, especially as of late, the P &L fluency, not just the CRO, but the executive team has needed to be up-leveled. And that's kind of been a lagging thing across the board. How much do you put emphasis on CROs having a strong P &L fluency across the org, not just sales? I mean, if they're smart enough, you can teach it to them. But I don't think a lot of them actually go into that role where they have a large fluency, AJ.
1:09:13In my experience, I don't think they do. Yeah. Do you think that that's important enough or that's secondary to everything else that comes to what we're talking about as long as they have a strong command of their own of the sales department i think it's secondary but it's something that they should understand if they want to be perceived as an owner of the business right like we talked about earlier it can't be perceived as like i'm only concerned about sales at this company i'm not concerned about the overall business this has been fantastic as we rack this up, I want to ask you a quick question.
1:09:46So a couple of famous people that have reported into you or come out of your lineage and get your like quick take on what made them special, what made them different. Are you sure I can answer that question? I might not want to. Well, as you said, you're not soft. You can skip one. You can skip one. Let's start with Dali at OpenAI. Like what made some special, what made some different? What can we all learn from them? Well, Dali's smart and he's super driven. Talk about, you know, those types of characteristics one he's smart two he's super driven and three he's got really good street smarts right his his intuition and stuff is very good so i don't again i go straight to his characteristics that's what i think that's exactly what i think about when i think about dolly what do you think about carlos at harness carlos really smart really took he took a little while to mature but right now carlos is like in you know how you know when somebody's like super comfortable in their own skin.
1:10:43Carlos is super comfortable in his own skin. He's looking good too. Stylish. He gets the s*** out of his people. He's fantastic. What about like from a CEO perspective? What made Dev so good at Mongo? You worked with him at Blade as well, right? Yeah. Again, the guy's really smart. He has a background in data centers and data centers because he did breakaway solutions before he did Blade Logic and BMC. So he has a lot of domain experience, you know, in there. And Dave's a driver. I mean, sometimes he can drive you in the right direction. Sometimes he can drive you crazy. Last one. Chris said...
1:11:25He'll probably hear that and he's going to want to get, he'll get pissed off at me. He's actually really smart though and super driven. what about Chris Snowflake now at Cognition back in the CRO seat he's a special man you know Chris is probably he's a smart kid but he's probably in the right place in the right time I mean those guys had lightning in the bottom right now he gets to see if he can do it again if he can do it again yeah you know Dali did you know AppDynamics and now open AI. That's when you know you can, when you can do it two or three times in two or three different disciplines, yeah, it's pretty hard for anybody to say you weren't good.
1:12:12Respect to Tris for like going back into the seat because you now get to learn that about yourself as well. And there's the risk in that. That's scary. There you go. That's the growth mindset, baby. You're welcome to a guy that did it five times. I know. John, thanks so much for being our guest on Topline and for taking time out of your schedule. It's great to talk to you. Thanks for creating this incredible family tree of great sales leaders and for writing the qualified sales leader and for being an inspiration for all of us. We really appreciate it. Thank you, Sam. Thank you, Saad. And thank you, AJ.
1:12:43This was fantastic. We'll talk to everybody next week.
1:12:52If you are looking for more Topline, Check out the Topline newsletter at toplinemedia.substack.com. That's toplinemedia.substack.com. Or if you're a video person, check us out on YouTube. Topline-media is what you want there. Have a delightful day, everybody.
1:13:25I love you.
John McMahon, a five-time public company CRO whose team at PTC created MEDDIC, joins Sam Jacobs, AJ Bruno, and Asad Zaman on building enterprise sales teams that last. Topics include the PTC lineage that has produced over 100 CROs, including OpenAI's Dali Rajic, why he hires on characteristics over resumes, whether a CRO who never carried a bag can lead, and how first-time CROs should work with their CEO. Plus, capped commissions at Anthropic, why AI makes lazy reps lazier, what conversational intelligence tools miss in deal qualification, and quick takes on Dali, Carlos at Harness, Dev Ittycheria, and Chris at Cognition.
Key Takeaways:
- Hire on characteristics, not resumes. John sorts candidates by skills, knowledge, experience and characteristics, and the last one is the hardest to teach: "I've always hired on characteristics. So I'll take someone with less experience but great characteristics." He looks for intelligence, drive, coachability, adaptability and integrity, because when a hire fails, "it's always a character flaw."
- Don't take the CRO seat before you're ready. John once refused a promotion Dali pushed him for: "I told him, I'm not gonna do that to you because you're not ready… you're gonna fail. Your ego's not gonna be able to take it." For John, readiness comes down to whether you can recruit, coach, and lead people who actually want to follow you.
- Talk to the CEO as a partner. Plenty of first-time CROs hold the C-level title without acting like the CEO's peer, and John coaches them to speak up: "You're the CRO. You have a fiduciary responsibility. Tell the CEO specifically what you think is wrong with the business." Blaming revenue problems on the product "is a non-starter," so come with a solution and talk like a business owner.
- AI hasn't changed the methodology. John sees AI mostly as a research tool, and "it makes the really good sales reps better, and it makes the lazy sales reps lazier." He is just as blunt about conversational intelligence: "All they're doing is verifying that something was said, but there's no true qualification." Qualifying still means knowing whether you're talking to a champion, a coach, or the enemy.
Connect with the Hosts & Guests:
Host: Sam Jacobs, CEO at Pavilion - https://www.linkedin.com/in/samfjacobs/
Host: AJ Bruno, CEO at QuotaPath - https://www.linkedin.com/in/ajbruno3/
Host: Asad Zaman, CEO at STA - https://www.linkedin.com/in/azaman1/
Guest: John McMahon, 5x Public Company CRO - https://www.linkedin.com/in/johnmcmahon1/
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Chapters:
00:00 Introducing John McMahon
02:18 The PTC Sales Leadership Tree
07:20 Hiring on Characteristics, Not Resumes
12:10 Should a CRO Have Carried a Bag?
16:50 Capped Commissions vs. Equity Upside
19:05 When Are You Ready to Be CRO?
22:56 How CROs Should Evaluate the CEO
34:52 AI and Sales Methodology
38:10 AI Call Tools Don't Qualify Deals
40:52 MEDDIC and Bigger Buying Groups
42:51 The Art and Science of Selling
48:47 Coaching Mark Roberge at HubSpot
59:31 Managing Heads Like a Bond Portfolio
01:03:42 Hiring Batting Average and Ramp Time
01:09:40 Rapid Fire: Dali, Carlos, Dev, Chris





