The Unwritten Rules of CRO Survival | with Rick Smolen, CRO @ ShipHero

0:00AI is a leverage tool. It's like debt can make performance exceptionally good or it can bankrupt you. That's Rick Smolen, CRO of ShipHero and advisor to Riverwood Capital's portfolio of more than two dozen enterprise software companies. He's seen what winning with AI looks like, including a play he calls an actual cheat code. But he's also a skeptic and he's seen revenue operators get burned by AI before. People are still doing work and now they can do really poor work at an exponential level. So in today's episode, we cover how to avoid obliterating your results with AI. But we also cover a lot more ground, how revenue leaders are really judged when their number goes sideways, Rick's scorecard for great revenue leadership, and a debate about when to stay with a struggling company versus when to leave for greener pastures.

0:47The reasons for your departure are not necessarily because... If you own a revenue number in the age of AI, this episode is for you. Welcome to Topline.

0:57Sam Jacobs: Welcome to Topline. I'm your host, Sam Jacobs. I'm joined by my co-hosts. I'm also a co-host. Let's not, and nobody get upset. I have two co-hosts, Asad Zaman, the CEO of Sales Talent Agency, and A.G. Brunner, the CEO of Quotapath Leaders in Incentive Compensation Management, or ICM, is the category. If you're not familiar. And we've got a great guest, a good friend of mine, a New York resident, and an incredible sales leader. His name's Rick Smolin, Richard Smolin, and he's from the Philadelphia area originally, but let me tell you a little bit more about him. He's passionate and he's a results-focused revenue leader with over 20 years of experience.

1:35Sam Jacobs: He's currently CRO of Ship Hero, where he oversees all go-to-market functions. He's also the sales advisor for the Riverwood Capital Portfolio. Riverwood has over two dozen investments in enterprise B2B SaaS companies. Rick teaches at Pavilion's CRO school and is also a facilitator for force management and their very famous command of the message training. Rick led sales at Lupio Greenhouse Software, and he spent 12 years growing up in sales at Intralinks, where he also lived in Hong Kong. Fun facts about Rick Smolin. Rick, welcome to Topline. It is great to be with you gentlemen. AJ, Asad, Sam, thank you for having me.

2:17Sam Jacobs: We're excited. We're going to dive right in. We're just diving. Let's dive. No small talk. No ditties. Remember when Sam used to do ditties, top line ditties? And they were just caught. Those are going to be fun. All right, Rick, the first topic is artificial intelligence, pro or con?

2:39AI, what a novel topic, Sam, a topic no one else is speaking about. We're going to take this from a tall angle. Everyone else is talking about other things, but we'll dive into AI. No, but for - What if I said that AI is not good or bad? It's not deterministic in it of itself, but it's what we do with it that is going to determine whether it's positive or negative for individuals, teams, companies, the whole thing. That's my take on it.

3:07Sam Jacobs: I think if you said that, you'd be right because you wouldn't be taking a very meaningful position. It would be hard to disprove it. But let's talk about AI and go-to-market and specifically in sales. You are a practitioner. As I mentioned, you teach building the inside sales machine at Pavilions University's CRO school, but you run a field team, you run a marketing organization, you have some perspectives. There's a lot of money flowing into go-to-market tech specifically around AI. Where are you seeing AI not work? When you think about use cases that are just a bunch of hullabaloo and a bunch of hoo-ha, what comes to mind for you?

3:45Sam Jacobs: What's overblown? And then we'll talk about what's actually working. I try not to be, but I'm a natural skeptic. So when I hear about like shortcuts or cheat codes that are going to all of a sudden like springboard revenue results or go to market for a particular team or organization, my first emotional response is like, that sounds amazing. And then the like cynic comes out and is like, yeah, I don't know about all that. And so what I see in all the noise surrounding AI, at least in the context to go to market, is this cheat code approach that like, hey, if you follow my prompts, all of a sudden you don't need to do your job anymore.

4:21AI is going to do it for you. And so the things that I see not working is like the same things that people that weren't doing particularly well, let's say note taking, let's say follow up, let's say positioning, they're now doing extremely not well by introducing AI into it. And so thinking that it's going to substitute your ability to do good work, your ability to understand your customer, your industry, your product, be able to say the right things at the right time, like it's not going to do all of that. And so like it can be a tool to help you if you know what you're doing, do things particularly well.

4:57But what I see not working is like, let's see, is the easiest example. What do you guys do when you get an email and you know the person didn't write it? You know that this is just AI slop text that just showed up in your inbox? Like, do you have the ability to see over that or through that and actually like try to judge it on its merits? Or you checked out right away?

5:20Sam Jacobs: I want to answer this because it was very interesting. So I got a follow up from, we had a great guest on the show and I'm becoming friends with that guest. And out of nowhere, I got this email from, I didn't, and this is the point. I still don't know if this was a real person because exactly your point, Rick, it was a blob of Claude because the other thing I noticed and I'd love for my co-host to chime in. I don't, I think my chat GPT is much better writer than Claude is at this point. Claude doesn't seem to be able to write very well for me and, or at least it all comes out the same. So literally I got this thing and it was just all of this junk.

5:59Sam Jacobs: You know, it was just, it was like, you said this and that really landed. I'm like, oh my God, I've seen that my own like programmed follow-ups from Claude that I never click send on and I wrote back to this person and I said listen it's okay either way but are you a real person that's just one question I have to know before I move forward and I have not received a response yet wait this wasn't the guest that was on top line though right the guest was on top line I'm not I'm not trying to call them out they're a nice person but and so I but they had this assistant or something I thought at first I thought it was like an agentic follow-up to the conversation but it was literally such slop and to your point Rick I didn't know what to think I don't I still don't know what to think about it but not a lot that's because you're a good person Sam you know you want to try to find the good what you really should be is like I'm done I'm done with this person I can't I can't life is too short I think that's the way to like so I'm an extremely judgmental person I've realized and it's done me well so far so I'm gonna stick with it you realize that I keep being told this I'm just gonna own it and so okay so if I'm judgmental like I'm looking for things to decide what to do what not to do and when I see this sort of stuff I have a really tough time getting past it and then I think of that as the implication in a sales team especially when you think of like mid-market and enterprise you have such few at-bats.

7:29Are you going to take this sort of risk? And I think maybe that's the big thing where if you're doing SMB stuff, your TAM is the world and you can like burn it and still edge out wins and be a good company, but you've done all sorts of things that on the other end of the spectrum just won't work because you're going to turn people off and there's only so many doors to go after. It's an extreme turnoff. AJ, what do you think? i mean i don't remember the last time i answered a cold email in the first place but yours sam it wasn't cold so that's interesting but it's a similar problem that we've had since the beginning of time with sales is you just you have slop whether it's copy and paste and now you have ai slop i don't really relevantly see a difference outside of it that the text is like 10 times longer than what we were getting 10 years ago that's a huge difference yeah i mean i think that that's what's going to reverse a little bit of shit versus a lot of shit which one would you rather step in so i mean so yeah so i mean that's so that's the first thing is like people are still doing work and now they can do really poor work and you know at an exponential level the other thing that has me concerned just as like a passionate person for sales and wanting sales to be an excellent profession i feel like the magic in sales is often happening between the meetings.

8:49And so, you know, when I hear the like, hey, we want our sellers to be on the phone with customers like 85 % of the time, I certainly don't. Like, that's way too much. You need time to think about what the next steps are to strategize. And so how do you do all of that? Well, the first thing is you make sure that when you're engaged with a customer, you're taking good notes. And so we have this world of AI note takers where we think we're going to outsource great note taking to the computer when the computer can't capture the tone, can't capture the nuance, can't capture the content, can't capture that little like look that one person gave another on there or the pause that was a little awkward there.

9:27The things that actually are going to matter to the emotional decision-making of how the buyer might actually act, but it's going to capture a bunch of like objective things that actually happened 80%, which might not be relevant at all. And when a seller is going to say, oh, cool, I don't have to do note-taking anymore. Their performance is going to go backwards. There was this old study, and I don't have the details of it, but when teachers used to grade tests manually versus then they would grade tests using a computer, the results would go down with a computer. Why? Because when they were doing it manually, they could actually see what's going on.

10:04Why is the student making this mistake? And then they could refine their teaching to be able to draw better outcomes. But if the computer just draws out an 80 and 90, whatever the score is, there's no context around like, what do I do about this? And I think the same thing applies for a seller in an engagement with a buyer, like you capturing what's going on and then being able to process it, add value to it, iterate on it, think about it, and then determine what the right next actions are. I'm sorry to like AI, I don't buy it, isn't going to do that for you. Although when I get on calls, I see the AI note takers everywhere.

10:38You know, that benefits and benefits the manager because you know in two seconds i can get the gist of what actually happened but i'm not taking that as like the final product i'm taking that as like okay i got like 80 of what i need now i need the real good stuff like how did the customer feel i fully agree with this piece of it i think the one thing that i will you use you use the no take yeah but i do it very specifically so i use granola and whisper whisper is the one that i will call out here because i don't use whisper all the time but if i'm talking about something very specific where i know i need to take notes and recall each point of like the next step there i'll i'll actually just enable whisper for that like three minute part of the conversation but ased you know me i like i'm i hand write everything down i'm like super old school with notes and like things to do like i definitely do all the things i think what rick is saying What Rick's really saying, though, and Rick, I actually want to hear from you just on it, is like the engagement piece of sales, the ability to multithread, to really like take pieces of it and say, I want to quarterback this situation has just gone downhill so much because sellers have become less just they're just like kind of letting it all rinse over them at one time versus taking the pieces of it and saying like, these are the four most important things, not whatever the note taker is going to tell me the most foremost important thing.

12:00and then running with it. I think you're wrong, actually. And I want to get, I want to see where it falls on this spectrum. I think the best are much better. Like, I think just like in every sport, the best of today are usually better than the best of many generations at all. The game advances. I think just like that, if you sit down with the very, very best enterprise sellers, if you look at somebody like Dali, who just became the opening ICRO, He was AppDynamic, Zscaler, and Wiz. If you take his three best enterprise reps, I think they'd be better than John McMahon's three best enterprise reps.

12:37That's how I think of it. The game has advanced and the best are better. The average is worse. And the worst people today are really bad. But I think the best of the best are much better than before. But that's like any athletics or any sports. The NBA from 40 years ago versus the NBA today. hey, game's advanced and that's just how it's played. But I think we're saying the same thing because ultimately you're leading to the similar spot that Rick is, which is the worst sellers are worse than they were probably 30 years ago and the best sellers are better than they were. Is that what you're saying, Rick?

13:10Yeah, that's exactly what I'm saying. I'm not against the idea of note takers. So like, it's not like the technology itself is useful. It has its purpose. It's just not a substitute. It's not a cheat code. And that's my fear is that folks think that they can, outsource critical parts of their role and their work to the AI. And that's, in my opinion, a mistake. And I do want to pull on that thread a little bit. My prediction of how does AI impact go to market, I do believe that the best will become 10x better and the average will become in relation worse. And the bad ones will be 10x. It'd be unmistakable and hard to hide.

13:50And so you have a pulling apart of performance because AI is a leverage tool. It's like debt, like debt is leverage. It can make performance exceptionally good or it can bankrupt you. And I feel like that's the analogy for how to use all of these tools within an entire go to market organization, not just an individual seller and how they perform, although it will impact that. And so that's the kind of thing I'm seeing. The best are like, oh, man, I can use these tools in partnership, not in substitute, to make me, you know, faster, smarter, more prepped for the call, targeting better customers, saying better words, following up in a more, you know, efficient manner.

14:33But I still own all of that. You know, this is just assisting me versus someone that thinks that, oh, I can make the AI kind of do everything for me. And then Sam gets an email and he's like, what? Is this a person? Um, so that's, that's just like my prediction or what I'm observing and, you know, seeing how this is going. One of the great mysteries of top line, who sent that email to Sam? We will never know. You don't know? We were going to find out. Some people know. Asad already knows. Sam's going to hunt this down. I used to watch Columbo when I was young, so I can, I'm well trained. What was Columbo's first name, Asad?

15:11Sam Jacobs: Isn't it Columbo? No, it's AJ Columbo, isn't it? I don't know. I'm pretty sure. Oh, wow. Yeah, it is AJ Colombo. All right, moving on. Not a memorable part of his name.

15:24Okay. I think some of this is because there's this misunderstanding of mid-market enterprise sales. I think people forget that so much of the time people are buying these things for less of like, oh, the product is the thing that they bought. It's like the product plus. And it's like on the other side, somebody is trying to get promoted. somebody is trying to get a win under their belt like there's these like the the soft part of sales which is where the enterprise seller or the mid-market seller has to catch the nuance has to figure out okay this is what this person is kind of solving for how do i help this person get the thing that they want so that they actually buy my thing like so much of enterprise sales is about that and it's not just like hey i'll take my product i'll put it in front of people it's so cool that people will just buy it.

16:12If it was that, then I think all these tools and efficiencies and all this stuff would work really well. But if it's more of what, hey, Bob wants to get promoted, I need to catch that. And I need to figure out how does Bob get promoted and who's Bob's boss and like, what's the really, that stuff, I think you need a human being who can catch nuance and who's looking for that nuance. And I think there's a lot of commentators that probably haven't done that sort of sales and so they don't understand it. Hence, they have these very dogmatic views on the future and it just doesn't make sense.

16:44Sam Jacobs: Rick, when you think about what is working, well, first let's go through some use cases and I'd love to hear your perspective on it because one of the things that you have a hot take on is in-call coaching. And there's still this belief that so content generation or sort of the avatar idea that we're going to use AI to project all of us as individuals out into the universe in ways that are clearly becoming, at least for now, they seem pretty inauthentic. That feels not great. And so is it fair to, oh, I just got a reply. Hey, Sam, I am indeed a real person, I promise. Literally, that just came in.

17:27Mystery solved. Also, it was Frank Columbo, not AJ Columbo. I looked that one up. Sorry.

17:35Sam Jacobs: all the colombo fans out there we're covering some real ground today i feel so in the category of like tools like email uh writing on behalf of people what do you what do you think rick are you pro are you bearable i think that these things can be a thought partner but you have to own your content you have to own if you're emailing somebody it's from you you need to be able to stand behind it so yes like there's nothing wrong with saying hey here's a draft like Like, help me become more, you know, have it have more empathy because I'm naturally a jerk. Like, that's very useful. Like, oh, yeah, that is more softer than like the jerk I was being.

18:12But it's still your content. Like, you have to be able to stand behind it. So for, you know, copy, I think it's useful in thought partnership, but not as a substitute. That's my main point around it. What do you think about productivity per person? So there's this idea that the average rep spends 20 to 30 percent of their time doing revenue generating activities. The rest of it is administrative. And so we're going to use all these technologies to give reps a lot of time back. And hence, they can be three, four, five, six times more productive. And the supporting proof is that if you look at some AI companies today, at this point in the cycle, you have many companies that have reps that have performed net two, three, four times what quotas used to be before.

18:59And so those two things are connected. The world has changed. This is a new world. But then you kind of think about enterprise sales, like your world, and you think about a person has to sit on the plane and go somewhere. And there's only so many trips you can take in a month. There's only so many people you can meet in person. So the counter argument is that that sort of sales, there's not much more that you can unlock. There isn't a world in which an enterprise seller can have a quota that is five times what the quotas are today because they will not have the human hours to do the heavy lifting that would enable that.

19:35They are constrained in a way that AI can't necessarily massively unlock. What do you think about this? I mean, I certainly think that productivity is improving in some respect. I mean, Asad, I listened to some of the past episodes where you were talking about OTEs for top sellers going up and folks trying to generate, you know, higher quotas per AE and things, you know, that used to be 1.5 million, you know, is it go up to two? I mean, I'm open to the idea that we can improve the productivity of an AE, especially if we have to pay them more. And so I don't want to maximize the size of the team.

20:11I want to maximize the productivity of the performer. And so I think the thing that I tend to look at is like, how many leads can a salesperson, I mean, this is the Sam Jacobs school of marketing demand funnel. How many leads can a person reasonably handle in a month? And so every sales cycle is different. If it's an enterprise one, you're getting on planes, it's going to be less than, you know, I can do five demos a day. and then what expected conversion rate should I, you know, do we close these things at? And again, tools can make us better or, you know, our product can make us better and so that can go up or down, you know, at what value and over what time period.

20:47And if I have a logic that says I can get someone to$2 million because I see evidence that we can handle that or our sales process is easier or PLG or whatever's going on, I'm totally, you know, open to whatever makes sense for the role but doubling and tripling and saying that like you know the things are going to sell themselves I mean the thing that as somebody that is an advocate for sellers and wants to live in a world where AI doesn't take over and to have all the sales happening and I know there's people out there that are trying to get the AI doing the selling and the AI doing the buying the thing that I believe is going to make sure the humans win here is how irrational we are we are emotional beings.

21:28We make our decisions incredibly emotionally driven and we'll rationalize them and put a logic behind afterwards. And I think AI is going to have a tough time with that aspect when it's all rational logic data driven. And I think that's what makes a great seller is being able to pick up on the cues. You get a feel. I mean, I've woken up on deals in the middle of the night and I'm like, oh my God, we're going to lose this deal. And I'm Like, yeah, like there's something there. Yeah. So, you know, I love AI and all these tools to help my team and me be more productive. I feels good. But I made this joke in a LinkedIn post in the past that actually resonated was like, nobody's as impressed with your AI project or your new AI tool more than you are.

22:11You know, at the end of the day, you still are like have to go do the thing and, you know, and do all of that. So I'm open to better productivity. if you ask a person to show you their thing, like, you know, somebody's so excited and they're like, let me show you this thing that I did. And it's like three steps and skill and this. And it's usually like the receiving end of it. Like when you see it, you're like, okay. So you get a notification every morning that your calendar has these five meetings in it, right? It's like something like that. And it's like, you could just open your calendar. Yeah, well, I was falling into that trap.

22:43I was so excited by some of the things that I was doing. And I went, I was out at a, you know, a pavilion happy hour and I'm talking to somebody and I was like, oh, I've been working on all these great things. And so before I shared it, you know, the individual I was speaking with was like, yeah, it's so funny. I was in the same boat and I had this realization. No one cares. Like they don't care. You know, you're the only one that cares. And I was like, oh, my God, this is so helpful. Have your quotas gone up at Shapiro at all in the last year? Actually, no. Like we already had pretty high quotas and had a really good rationalization around what the OTE multiple to quota is.

23:24We have not raised quotas on anybody on the team. Now we have expanded the team. So we've allocated more quota. but I haven't felt the need. And while AI is helping our team in very significant ways, the selling aspect is still, you know, those metrics and variables that I was talking about. And I don't believe that if I was to, you know, double somebody's quota, that I give them any chance to be successful. Now, I'm not, but AJ, just one other thing. It's so funny. I was just thinking about this before we started today. 10 years ago, it was like revenue, revenue, revenue, grow, grow, grow. Then it was like, you know, the Zerp kind of bubble popped.

24:04Then it was like, well, let's be efficient growth. Like we're going to have, you know, revenue's good, but also profitable, efficient growth. I've never heard of it. But now even that, now even that's kind of like, you know, so 2022, you know, now it's like you need AI to go rocket ship wise. So I, if you can be one of the few companies that are in full rocket ship mode and every company in the world is buying them, like more power to you, make the hay. But for us mortals, I'm still in a like, let's run a strong business. Let's grow very smartly. Let's make good investments. Let's get, hey, 50 % ARR growth.

24:38It used to be amazing. Now, like not too shabby, I say. But I think most CROs would probably really feel like that you're saying what every CRO either wants to say out loud or is saying out loud in some ways. But kind of curious on just like how you're reporting back to some of the AI metrics. We had Mark Roberge on a few months ago and he was talking about this idea of revenue velocity as a metric and something actually I took and we now share at the board level. But is there anything that you're doing that's showing productivity as it relates to AI? if you're like, you know what, we're going to let the team, they've just got to be really good at their jobs.

25:16They just need to knock it out of the park. But we will start to do some of these things. Are you actually then on the other side of it measuring this in any way? There's two things that I guess that we look at. And it's, by the way, it's harder to hide as a revenue leader than ever before, because every CEO has every system connected to Claude and then can say, oh, I went into HubSpot and I looked at, you know, the conversion rate and the team in Q2 and it went to this. So, you know, whereas the CRO might have historically been dependent upon to provide those numbers, like anyone that's, you know, plugged in would say has access.

25:53And I think transparency is a great thing, especially when it's accurate. So one of the things we're looking at is like, hey, is the conversion rate improving? You know, so that's maybe, you know, one. And then two, is our team using tools that might help us, you know, win more deals? Like, are we able to say yes? Are we qualifying more deals because we can say yes to more requirements, that type of thing. And so generally, like, I'm not trying to make it more complicated than that. And so the one good thing I'll note for 2026, and we have invested in AI and it has helped in go to market. And I can give you a couple examples, meaningful improvements in conversion rate from a qualified opportunity to close one.

26:38And I don't believe that's just because our sellers are saying better words. I believe that they've been equipped with our ability as a company to be able to go win more deals. And that's awesome. I've been keeping an eye on the go-to-market teams at the three, four, five leading AI companies. And what's fascinating is that these are the leaders that they brought in. So if you look at the CRO level, Dali is running OpenAI. He just replaced their old CRO, who used to be the CEO of Slack. He was the AppDynamic, ZZ dealer, and then WizJai. If you look at Cursor slash SpaceSets now, it is the rubric CRO that has been brought in over there.

27:25If you look at Factory, there's another one of these John McMahon lineage. And you have deeply connected to the lineage of John McMahon, right? You teach the program that is based upon his methodologies. And then I think at Anthropic, you have somebody from ServiceNow. So it's like the old classical enterprise sales leaders and coming in and rebuilding those teams. These teams don't look all that different from the leading sales teams of the previous generation. And there was a point a couple of years ago, maybe about a year and a half, two years ago, where people said, oh, sales is going to be completely different.

28:06These companies are going to do it differently. And there was a moment, right? There were no quotas and there was all this fancy shit. And we're back to like, let's just hire John McMahon's disciples and let them run at the market. Well, I mean, that doesn't surprise me because there's nothing magical about what John McMahon advocates or what the methodology that any of the leaders of the companies you mentioned focus on. There's nothing magic about it. All it does is puts the onus on creation of customer value. And instead of peddling, like, let me show you how awesome this stuff I have is to take a look.

28:43You want to buy it? What do you want here? It's let me uncover problems that are actually worth spending money to solve. Let me influence what the decision criteria should be on that, and I'll win at influencing what actually matters in your decision-making process. And then let me position my solution in a way that's relevant to solving your problem. So it goes from a world, and I talk about this at CRO school, sales used to be, it used to be you won if you were an expert in your product. Why? Because if you needed to get information as a buyer about a product, it wasn't ubiquitous all over the internet.

29:22It needed to be installed with servers and you needed to be educated by the vendor. That for 50, 100 years, the seller's success was about product expertise and maybe relationships. All right. So that was the world. And there's so much inertia on both the buyer and the seller of like, if I know my product really well, I can be successful. In today's world with information everywhere, switching costs incredibly low. The winner is in somebody that can actually diagnose the problem better than the actual buyer can do it themselves. So now you don't just need to be an expert in the product. You need to be an expert in the industry.

30:03You need to be an expert in the trends of where CFOs will spend money. And you need to align to outcomes for customers. So you're a lot more about the customer than you are about you. But we are all egotistical people and with social media and everything, it's all me, me, me, me, me. It's very easy to fall in the trap of, let me do the easy thing. I was trained on this product. I'm going to show you a product. And this is what these methodologies all teach. They're all anchored to, it's not all about you. Let's really understand the problem. Let's really make sure that we're aligned to it. And let's make sure we differentiate in what's important in your decision process.

30:40And it's easier said than done. It's actually like tough to execute that well. But the ones that do it well, they go on and do huge things. It doesn't surprise me at all. What about from a pipeline perspective? So you are running marketing now. And I think at least from you and I agree a lot on like the sales side of it, like how much has changed, how much hasn't changed and what the game is. I'm curious, as you're running marketing right now, what you're noticing on the top of the file, has anything changed there in terms of ages generally, how hard or easy is it to develop pipeline, number one?

31:20And number two, what's working for you? What's driving the majority of that pipeline? And there are some really interesting AI use cases over there that we're hearing about. Have you seen anything pop for you on that side of the equation? Well, you were talking about this with a past guest, but you were talking about how hard it is to build brand and how important brand is and how CEOs in the past will not necessarily fund brand type initiatives that they don't believe the work that's being done is actually going to enhance the brand. So I still think brand is incredibly important and very difficult to be good at.

31:55And so within your vertical or within your industry, if you can establish a differentiated brand that gets more attention, you know, hugely, hugely valuable to be able to do that. And I know, you know, Chip Hero, we spend a lot of energy and effort to be the thought leaders in our, you know, space as an example. And are you running the brand side as well of marketing? I mean, I have responsibility over at Asad, but that would be inaccurate to say that I'm running it. Like the team that does that is doing a far better job than I would. I do think it's positive that there's like oversight of the entire go-to-market at one level, but success there doesn't mean that I go run around and try to do those things.

32:35Like I'm, you know, I'm responsible to make sure that people are working in harmony and that we have the right people leading those functions. Are there other execs that are interested? I mean, typically with brand, everyone has like a fascination with it. CEOs sometimes get involved. Is there others that are just like really, really interested? If the CEO is not involved, that would be problematic, right? I mean, I would say that the two people that are leading the charge at brand at our company is our head of marketing, who is absolutely brilliant and has my complete trust. And our CEO, who lives, eats, breathes, sleeps.

33:07He's a founder-led CEO. I mean, he's focused on it all the time. And they come up with amazing ideas, experiences for our customers, content to be able to do that. So I think we actually do a good job in that area. But the area, to get back to your question, Asad, is like, okay, what are we doing differently now? Or where are we trying to focus energy? Or what does tools and AI unlock for us in that area? I think it's like this movement from Google paid ads, that's like all going away. Like all the budgets are moving away from doing that. We don't even do paid search anymore at all. to how do you show up in the LLMs?

33:46And so what do they call it? AXO or AEO or whatever. And no one knows the exact answer on how to do that. And everybody's experimenting or trying to figure out how to show up more within that context. And we're no different in terms of doing that. But the areas that I might get involved in are like, what are the controllables? Well, with Claude and other tools, I can build lead lists and Clay and the other data providers. I can build lead lists better, faster, deeper than ever before. It's a cheat code. Lead list building and ICP identification and contact identification, those are accelerated.

34:26You can build better target lists. Now you can now build better campaigns to go after. So ABM hasn't gone away, but it should be more effective. You can layer in intent, you can layer in signal. So your ability to do the things that marketers have been trying to do for the last 10 years has just been more enabled with this technology. And so we're investing to just try to be better at those sort of classic activities while brand and content and other things hopefully is, you know, driving just the general organic, you know, website direct traffic based, you know, lead flow. but my outbound should be better because I'm going after a better high fit ICP.

35:11You know, my, my campaigns and events and, you know, things that I'll experience that offer should be better because I can drive better attendance to my target audience. Cause I'm going after the right people, maybe LinkedIn ads or some of these other areas, like they should perform better because I'm know what I'm doing more. Does that make sense?

35:31Sam Jacobs: This episode of Topline is brought to you by Tourette. Every CRO is asking the same critical questions. Why are win rates dropping? What are my closers doing differently? How do we beat competitor X? Despite massive AI investment, sales teams still can't get complete answers or take action on partial insights. Tourette changes that. Tourette is the only answer to action engine that gets to the root of revenue issues, then executes with relentless precision. Tourette answers your questions with a complete revenue graph, operationalizes those answers for your teams through AI architects and deploys them to reps through AI agents.

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37:02Sam Jacobs: T-E-R-R-E-T dot A-I. This episode of Topline is brought to you by DevRev. Listen, I want to tell you something I've been really excited about lately. It's called Computer by DevRev. I know you might be using your own computer to do things that computers do, but this is different. Listen, we've all had this experience. You need the answer to a very simple question, but the information is buried across Slack, email, Granola, Salesforce, Jira, other tools that you might notion. So you spend 20 minutes hunting around instead of getting things done. And that's what computer by DevRev fixes. It uses shared memory to connect all of your data.

37:39Sam Jacobs: So your teams and your customers get precise answers they can act on in seconds. Shared memory means computer does it using just a fraction of the tokens leading frontier models burn. Take a look at devrev.ai. This is computerbydevrev.ai. Rick, people need that. They need the right answers. They don't want to spend an arm and a leg to do it. So computer by Devrev. The thing that I'm finding on their site is they have so many integrations. Figma, Jira, Notion you mentioned, Sam, Slack. I don't know if I've seen anything like this where they have so many integrations just to be able to find the answers.

38:17So agree with Rick on that. I love it.

38:18Sam Jacobs: And that's really the point of computer. by DevRev. So go over to devrev.ai, D-E-V-R-E-V.ai, and thank you, DevRev, for our sponsoring Topline, and thanks for building computer. Hey, everybody. This episode of Topline is brought to you by Pavilion. Join us beginning September 28th through October 2nd for a week in New York City for the annual go-to-market event through Pavilion. We're going to feature over 1 ,000 operators in the same room. we've got a dedicated day for CROs, CMOs, and CEOs and RevOps. We've even got a day just for guys like Rick in Pavilion Gold. Meanwhile, we've got Jeffrey Moore, author of Crossing the Chasm, giving a keynote.

39:03Sam Jacobs: And we've also got Nick Mehta coming. He's about to announce something brand new. And he'll announce his new company on stage at GTM. Maybe, or not sure. He didn't say that he would, but I'm saying that he might. Asad and AJ will be there as will Rick Asad, your favorite memory from going to GTM all of these years all of the times that you've gone to this conference every single year every single year he's been there Asad showed up live in person always I can't believe you've given rev-ups a whole day to themselves that's so cool that's a seat at the table, Sam that's a seat at the table I will tell you, Asad my favorite memory when we were wearing cowboy hats in Nashville, the three of us.

39:47Sam Jacobs: Yes, that was 2023. That was three years ago. AJ Bruno, favorite Pavilion memory doesn't have to be GTM. Well, the Pavilion Gold event in Mexico was a standout. I still talk about that event today. So that is definitely there. But Sam, I will be there. Is it at the end of the quarter, the last day of the quarter? Yes. Does that change anything? No, I'll still be there. Rick, will you be there? I will be there. I don't know if you remember this, AJ, but the first time I met AJ Bruno in person, I was excited because I've been listening to the Top Line podcast was just before Sam Jacobs did his keynote at last year in Washington, D.C.

40:26at the GTM. It was up on the second floor. Up on the second floor. I'm sitting in a chair and who pulls up in the chair next to me in the balcony? AJ Bruno. And I was like, this is a great moment. And I felt very good vibes. And then Sam came out and he did his thing. And he's going to do it again. A few weeks. I had to take a video of Sam. He announced Topline as a major initiative. And, you know, Asad was there. He just happened to be in the next room over. So I had to text him. In spirit.

40:53Sam Jacobs: Since that announcement, we've all gone to become the number one podcast in all of business. So it made a big splash. Honestly, everybody, GTM is going to be great. Attend GTM.com. All four of us are going to be there among a thousand other go-to-market operators. it does make sense one of the challenges that marketers have i'm sensing is that there's this impetus to be everywhere because everybody feels like well if ai is going to compound your leverage then you need to produce way more content you need a page for every possible iteration you need more ideas out there and and when that establishes the productivity threshold that's when i see people resorting to just letting the AI write everything.

41:41Sam Jacobs: And I think there's lots of people like, no, we have a skill. We trained it on our brand voice. It now sounds really human. And I have yet to see consistent output from an AI that actually does sound human. It always sounds the same, basically, and you can spot it pretty easily. And so it worries me a little bit to the point of brand that I think people think they've got productivity and leverage. And I don't know that they do because I think what they're doing is magnifying some level of mediocrity. I think to your point, Rick, the place where the game-changing things that I'm hearing from front lines are exactly what you said, which is you combine new mechanisms and tools around email deliverability in real time with list building.

42:30Sam Jacobs: So I know somebody that is building custom segments in real time before they send the email. They are checking to make sure that that is a real email so that they know it'll go through. They've optimized the ability to deliver that message to a very custom segment, which is, I agree with you, that is the power of a lot of AI is working within Claude and saying, build me a list of a thousand CROs that just got promoted. and if you have the right integrations that should be able to happen within about 10 minutes. Stan, your point around the role of marketing is to be everywhere all at once is so true and in the sense of like that's the area where I see marketing struggling the most which is we have these budgetary pieces where budgets have increased or at least from what I've seen budgets have increased to, okay, let's start to train on AEO or GEO stuff.

43:25Let's like actually test that out and that experimental, especially in competitive spaces, there's a lot of companies that are just lighting cash on fire in those areas. And then we just looked at our budgets, it's like, whoa, wait a second. We have increased our budgeting spend quite a bit going into this year. We knew what it was going to be. We're doing a lot of different events, doing a lot of different things on the GEO front. And when we look at it, it's like there's a lot. The ROI and the CAC to specific channels has gone way up. It does feel like where we are in 21 in some ways during the ZERP era.

43:56for some of this. And then on top of that, you add the fact that what you just said, which is like you just put content and you can spray and puree on any of these. It feels pretty messy overall.

44:08Sam Jacobs: Yeah. And I feel like the marketers feel like I'm expected to produce this level of output, you know, so I need to, I need to be able to generate 20 pieces of content by tomorrow. So this is the best I can do. And then you go through it and you're like, well, it feels like AI wrote all of this. And that's the point around the targets going up to my question to Rick earlier is like, well, if those targets are going up and pipeline targets have to be going up. I mean, I would just assume as a function of inbound as a part of your sales channel, you're not putting this all on the BDRs or even the salespeople themselves.

44:41Your marketing channels have to go up too. I think the conversation has to be, and this is something I've been thinking about recently, which is we can't talk about go to market and sales as one thing. Now there's two very different games. There's the inbound. Thanks, Paul Graham. PLG shit, you know, there's some version of like take PLG and SMB and bucket it together and there's that game. And then there's mid-market enterprise strategic. These are very different games. I don't think that there's a lot of reason to believe that people that have to travel to see customers and do dinners and do conferences can do three, four times their quotas.

45:18Maybe they can do a little bit more. there's a difference between we're in a hot market where there's a gold rush happening because of which people are performing at crazy levels because buyers are just throwing money to try that's word of mouth demand so that's different you can't really count that you'll have reps do crazy numbers but when this settles down do you think the enterprise seller at you know the mongodb equivalent has a quota of 10 million dollars like there's no world i just don't see it. How are they going to take more trips? How are they going to meet more people? And so I don't think their quotas go up that much.

45:55But they might need a little bit more pipeline than before to be able to hit those numbers if the market's more competitive. The pipeline will be driven by the competitive nature of the market and hence the win rates are going down. And so we need more pipeline. But it won't be like multiples more than before on this side. Whereas Kyle Norton did have reps performing at a much higher rate than SMB reps to perform before, like much higher. And that I think is very realistically possible today.

46:25Sam Jacobs: Yeah. And I think, but I think a lot of it to your point, Asad, I mean, he might, he might, you know, articulate a bevy of different tools, but a lot of it was the connect ratios that he had by building, you know, good data and good databases. Yeah. It was like, we had better connect rate. We found better data. We reached out to people, we actually were reaching out to the right people. Like that was the biggest difference maker. I hear good things about the enablement use case of role playing. I do hear really good feedback on that. And it made sense, right? Like it made sense that you can give a rep a lot more repetitions at role playing and a lot more flavors of role playing.

47:05That use case makes a lot of sense. And hence, people can get ramped up a little bit faster. They can probably round out their stills a little bit better and they're less reliant on the randomness of the market to give them all those repetitions that do you do you all use ai role-playing at all at shapiro we do not but i am a supporter of the concept i think like the concept makes sense to me have you tested anything it's been a year and so i'm sure it's come a long way but it didn't feel authentic enough in my initial piloting of it that i thought that like somebody would take it seriously. And so the concept remains good.

47:45I think like practice layups, free throws, like NBA players do that ahead of the game. Like it doesn't seem crazy to me that like sellers would practice in some way. My past review of the tools available was that with my particular team, adoption level would be really low. And do I have a major problem? I wasn't hiring a dozen salespeople. Like the landscape was such that even though I like the concept. It didn't make sense to invest in that for the particular team that I was responsible for. But I generally think that that will be a solid use case. Imagine hiring somebody and getting them up to speed a lot faster.

48:23Like that is very valuable. It takes a seller a long time and you don't want to waste leads, you know, in terms of their training. So I generally like the concept. But AJ, just getting back to real quick to close out on what you were asking about with like pipeline going up or what do you need to be able to do that? You know, and so on. I think that the key is around, you know, like your executive team, the communication that happens between the CEO, finance, you know, the CFO, your CRO, like, like finding the right balance of like, what is our posture around spend on marketing? And what do we expect on pipeline?

49:01Like, I think the downside is making these decisions in a vacuum. The positive view today is making this an aligned decision of what is our organizational posture around the bet we're making, the investment we're going to put there. And then what do we expect to achieve and getting multiple inputs on that on your particular business, which brings me back to like the humans would never been more important. Like the way we communicate, the way we work together as either an executive team or even within our cross departmental stuff is to me, what's really going to dictate the like ceiling of like how much success you can get to.

49:37Sam Jacobs: I love that, Rick. Let's transition to one last topic before we go for the next 15, 20 minutes. Because one of the things that you're passionate about is leadership in a confused world. And you have sort of pillars of leadership. I think it's so important right now because I think, you know, there's the nuts and bolts, there's the dollars and cents and the figures, but there's also the mindset and how people show up to work every day and how they should think about leading in a time as chaotic as the one that we're in. So talk to us a little bit about what you think are the key concepts that people need to show up to work with and lead with if they're going to be effective.

50:16Yeah. Well, I was starting to think about like, am I even good at my job or not? And back when I was in sales, it was pretty easy to know the answer to that. I could feel it. First of all, when I was winning deals and like winning competitive deals and, you know, like I still remember every like deal that had real meaning to it that wasn't a layup you know that wasn't an order taker type of thing and like what I call the magic moment where we like turn the tie so very easy as a seller to know like am I doing a good job then I got into leadership and man I had no idea you know like the idea of like what you expect that job to be versus the reality is like so different.

50:58And so after 15 years in a leadership role, I was trying to figure out, okay, what are the variables that one could look at other than business performance? Because I don't believe a sales leader or a CRO should be measured solely on business performance. There's a lot of bad CROs that are part of great products and companies. I bet you all can think of companies out there right now that are just rocket ships. And the leaders in those positions are just in fortunate positions. That thing's going to the moon with or without them. The CRO of OpenAI getting fired right when they reaccelerated in the enterprise is like, they reaccelerated at a staggering rate at the enterprise level once they refocused there, and then they fired it.

51:42So that's interesting, right? Yeah. So I was thinking about, okay, business performance is an indicator. It's not the indicator. So what are the things that actually matter? What would I evaluate the folks that report up to me on? First is absolutely no-brainer talent. So like the quality of the team that you build, the quality of the team that you manage is 80 % of the game. And so, you know, do you have the right individuals based on what the maturity of your company, how it's evolving? Is it a zero to one? Are you at product market fit? Are you at scaling? What do you need to do? That is a, easy to become biased and to rationalize a core performer or mediocre performance and try to rationalize the positives of that individual.

52:26But continuing to upskill that team, continuing to hold a high bar and bring in, attract and identify the right talent, that is a very, very tough skill to have and great leaders have it. So the first thing is, is it a leader building the caliber and quality of a team? Can they attract and identify that type of talent? So that's the first and probably the most important. But then there are other variables as well that I've sort of tried to hone in on, you know, to try to determine like, am I good at this? You know, I call it operating rhythm and that's probably too broad of a term, but I try to think about like, is the team motivated?

53:05Are they engaged? And is there accountability? Because some of these things can have a tension with it, right? Like motivating somebody and having accountability for performance can have tension between it. So how do you foster an environment, a set of rituals, meetings, clear expectations in such a way where you can have clarity and high motivation, high engagement from the team, have a high bar. There's this real skill in the caliber of that that exists or your sales team just running over you, which all these scenarios exist out there in the world. Can I click on that? I have a question on this because I think about this in relation to myself.

53:46When the market's down, if I'm doing the same set of things when the market is down versus when the market's good like today, the resulting motivation, engagement, et cetera, is very different from the team. And so in that moment, I'm like, you know, everything I'm doing is shit because like the thing is, the argument would be that when the market's down, a bunch of performance-minded people cannot be happy in that moment, right? If they're not performing, their morale is going to be down. They're going to be annoyed, all of that. And you want a little bit of that. I want that in my team. If we're not performing, there's like, let's get this shit going.

54:26And when the market's really good, like, you know, everything, everyone feels great. Am I that different in that moment? We're kind of doing the same things. And so how do you calibrate based on the state of the economy and hence how easy it is to perform and not perform? We have to adjust. There's the macro, right? This is the environment that we're in. And you just explained that perfectly. There's down markets, up markets. That's the macro environment, the context with which you have to work. And then there's the micro, the things that you can control as a team. So your motivation and how you are rallying the troops, so to speak, will differ based on what environment we're in.

55:02I mean, our theme at sales kickoff this year was catch the wave. Our company is going to be the leader in the space. The industry and market that we're in is growing meaningfully. The wind is in our sails. This is the year to catch the wave. The macro is perfect. Let's go make it happen because storms come in one of these days, but now is not the time. let's go maximize the outcomes that are possible within the world that we're in. And so I firmly believe that. And as somebody that's been around this game for a long time, I want the younger folks in the team to see that this won't always be this way.

55:38Make the hay while you can. Go make that money. Go perform. Go motivate because it might not be this easy in the future. And then, of course, there's been plenty of times, man, we can remember 2022 was a tough year to be in enterprise software when like the budget stopped. And so then it became about, you know, all right, like we have a difficult situation. It is our responsibility as the revenue team here to play the best hand possible and to come up with innovative and creative ways to maximize our outcomes within this difficult context. And maybe there's organizational things you would need to do to, you know, modify bonuses or have SPFs or, you know, have something to, you know, maybe motivate other than sort of thematically, maybe financially.

56:20But that's part of the like why there's no staticness in terms of leadership. You've got an ever-changing landscape with which to, you know, which to talk to the team on. And I do think like success is not sugarcoating it, but being authentic and real and giving a bunch of context and whys and, you know, motivate based on outcomes and what they can achieve for folks. On this, you can be a therapist to some of the CROs I've spoken to recently. Use Airtable as an example. There's many Airtables in the market today. You know, 20-ish percent of their reps were hitting target. They'd lost product market fit.

56:59No one was making money. All the reps were leaving. And you've got a bunch of CROs right now in these seats. And what they see is really high attrition of their good and great performers. and they see a market that's not responding to their product. And the questions they're asking themselves is, is it time for me to jump ship? Like, do I just, like, is this time to roll? Or are there a bunch of things I can do to, like, stabilize my sales team? Because once your sales team is, like, unstable, like the good ones are leaving and you aren't able to replace with good ones, like, what do you do at that point?

57:35So is it like, it's done. I see the sign. We've lost so much product market fit that I can't hold on to enough of a good team for us to fight a good fight. It's time for me to jump ship. What do you say to those people? Are you saying stick it out, find the product market fit, get the exit? Are you like, hey, this is time to make, hey, like go bounce, go somewhere where you can make real money. Why are you at this shitty company? They should definitely leave. No. You know, it's a great question. I think, look, this is what makes the market move is that there's different strokes for different folks and there's different things that motivate people.

58:10I think there are folks that have certain risk tolerances, like they'll go take a new job because they want to learn and go do different things. And there's folks that like, man, they do not, they'll go down with the ship because this is the devil they know. So, you know, your personality profile and your risk tolerance is going to have a factor in terms of what matters for you. But I think a CRO or even any executive, their performance should be measured as follows. based on what's going on right now, what is your plan moving forward? And do you have the right plan for where we're going from this moment in time?

58:45And not like rationalize why this was bad or make an excuse of why this is there or blame product for this or the competition for that. There's a lot of stuff going on and you need to have the plan. How many hacks do you think they get? As a CRO, you've been in this scene many times now. How many of those do you get? where like things aren't going well, what's your plan? Let's see if it's the right plan. Because you can, I imagine as a CEO, you hear that once and you're like, okay, here's the plan. I like that plan. Let's try it. And it doesn't work. Like, oh, it's not working. And then you get like plan number two.

59:20Like, is it like you have maybe two tries at this? And by the third one, they're like, yeah, what's your plan? But they're also running the search with SDA. It's three envelopes.

59:29Sam Jacobs: It's exactly what you said, Asad. I think it's three envelopes. You get two chances. Two chances. What do you think, Rick? Like, I'm going to only speak for, you know, my as an advocate for other CROs and revenue leaders out there in the world. My belief is as follows. You should hold yourself accountable to your plan. You should have a plan and not excuses. And the plan should maybe it needs to be bold. Maybe it needs to be incremental. But like you should be proud and feel good about your plan. And if you do and you did the work and there's no like, you know, shortcuts, then like no matter what happens, you should feel like, hey, I'm doing good work.

1:00:08I'm playing for the best result in the future. And you should be, you know, chest out, feeling good about it. that is not necessarily the same as how you are being judged. And whether you're being judged by a board or by a CEO or a combination therein, like I have been fired multiple times. So I can speak to this, Sam, you as well. The reasons for your departure are not necessarily because of your plan. There are a lot of factors at play in terms of why you will be at an organization or not. And so worrying too much about the politics of this is not something that I recommend. Can I ask you guys a personal question on this?

1:00:49I've never been fired. So let me, I'm curious. I'm a vindictive person. How much joy do you get from when you get fired and then things get worse? I would get joy from that, like being honest, like you get fired and then it gets worse for the company or for you? Yeah, like they fire me thinking that that's going to fit some shit and then it gets worse. I would be joyful at hearing that. I mean, I didn't get fired from the role at Meltwater, but I just went and started a competing company. Yours was like, at Quotapath there's a revenge company in a way. No, TrendKite was a revenge company. Quotapath is more for, because I wanted to be a CEO and wanted to be in the seat and figure it out.

1:01:32So there's the revenge chip on the shoulder there but trend kite was i had a terrible boss which i've talked about and it was awful and i was like i pitched the idea of trend kite to the ceo and he said no uh that doesn't make sense and then i was like okay i'm leaving and going to start this company thanks and then and they told you you can't do this well the boss that that like was awful and said you're you'll you'll make a business and it'll lose millions of dollars he ended up getting fired from Mount Water a year later. It is kind of true, though. You made a business that lost millions of dollars.

1:02:05You just sold it for a lot of money as well. Like, he didn't understand the game. Hey, those are details, Austin. Those are details. Don't worry about it. I've actually only been fired one time in my entire life, which was at a grocery store when I was in line to buy a can of Coke and a person, secret shopper, someone that was, like, working undercover for shrimp. I used to do that undercover job. They, like, they would walk up to me and said, asked me if I had a receipt while I was in line because I had opened the Coke and was drinking it. And I got fired from that job. Um, but I didn't say, like I said, there's a lot of random reasons why people lose their job.

1:02:39Yeah. Asad, I don't, I don't believe you. I don't think you would be vindictive. I think if you were in the actual situation, but you got to understand, like, and especially good, you're a good leader. Like you understand when you're in these situations, it's not personal. Like it feels very personal. Don't get me wrong, but it's not personal. It's business. I mean, I hate to be cliche around it, but it really is true. And you also learn when you go through these things, like, it's not all about you. It's just not. You're a player in the game. And it isn't all about you. For any organization that, you know, I parted ways with, for whatever that reason was, I've been rooting for them to succeed no matter what.

1:03:12And that's not me being glib or just trying to be political here. Like, it's just honestly true. I genuinely think you're like that, because I remember telling you once about one of these companies not doing as well after you left. And like, you didn't get any joy from that conversation. Yeah, it was very authentic. Like, I was very impressed because I would have gone joy. People you worked with for years, like to want them to not do well. I can't, I have a hard time imagining it. Now, don't get me wrong. Like, you know, it's not, I'm not trying to say it's cool to like get fired. Like, no, don't do that if you can help it.

1:03:44But I just don't think it's like, you know, you realize that it's just, there's a bigger game at play and you are just merely a piece in it. And you know what? That's a good way to live. You know, they can take things a little less seriously. I once told a guy that I was firing him that like, and he was awesome, but it just wasn't the right timing or fit. I was like, you're going to text me in a year time. And the text is just going to say, fuck you, AJ. And I cannot wait for that text. And he did. And he was, he became the CRO of Procore, actually. Oh my God. Like five years after. But he was awesome.

1:04:16And I knew he was awesome. We were just too late to the game to hire him. It was just a timing thing. and we became pretty good friends after that. We became the Seattle ProCore. That was, yeah.

1:04:28Sam Jacobs: There you go. I mean, when I've been fired, first of all, to Rick's point of view. You wouldn't be a more similar. Well, no, I mean, maybe a little. First of all, there's going to be a correlation between the company not doing well and you being fired. So it's more likely than not. If you believe that product market fits the thing and that you got to catch the wave, as Rick said, then it's more likely than not that the company probably is going to do worse for at least a little while after you leave. And there's one company that has objectively done really well after they fired me, the last place I worked.

1:05:07Sam Jacobs: And they're executing well, and they believed in a very young CRO that used to work for me that was basically like a co-founder of the business, and he's still there eight years later. So that company has done great. Most of the companies that fired me did not do great after. And even now, I don't know, my vindictiveness has really receded. I mean, each company that parted ways with me were right to do so. It's always the right decision because obviously if it's not working, it's not working. And it only needs to not work for one party to believe that. I've been expelled from every school I was in, and that's why I do feel like a vindictiveness.

1:05:45That's my only comparable. But we're only criminal? What did I do? Huh? Weren't we a criminal? No. I was now convicted, Sam.

1:05:59Sam Jacobs: It's like, I knew all the gangsters in Lahore and Islamabad. I could have people beat up. And it's like, okay, well, maybe you should be expelled.

1:06:12Sam Jacobs: Rick, we're almost at the end of our time together. Asa, do you have any bulls versus bears questions on top of your mind before we go? Bulls versus bears. Yeah, I keep thinking about getting people's opinions on Salesforce. We're using Salesforce. I imagine that you're using Salesforce, right? Like, are you bullish or bearish? You've seen the various implementations of AI within the product. Wait, you went back to Salesforce? We're HubSpot. You're HubSpot. We're on HubSpot. oh wow at that i just i don't know i assumed at your scale like it's like hubspot is never there that's hell that's interesting are you bullish or bearish on hubspot then i'm bullish i'm but what is what like yes somebody could create you know an in-house crm or whatever why would you like this these things aren't going away i'm i'm bullish i i actually you guys were debating this in the past and I'm more on AJ's side here where it's like, this is, I'm a buyer.

1:07:12Oh, my. HubSpot is a great business. I mean, yeah, the UI isn't fantastic, but like I would say our organization, more things are happening within HubSpot, not less things. That's interesting. And so Salesforce, HubSpot, like I'm in, I'm not, I'm bull. I like it. Asa, did you switch to Salesforce? No, I was on Salesforce before we churned on a bunch of, but we're on this shitty ATS we're about to churn from as well. If they had good customer research, they would get some. Hopefully their account manager is listening to the show and it's like, I hope they get this notification. We're about to churn and they don't think we're about to churn, which is weird.

1:07:55I was just going to say, I see all these postings on LinkedIn about people like, you know, saying I don't need HubSpot or things like, you know, it's like a three person company or like a solopreneur. Like, yeah, you don't need this. You need to add your company. If your company ever became like 50, 100 people, you're going to need something like that. I think that it is interesting to hear that from somebody that's using HubSpot, because most of the people that are using these platforms are not thrilled with the implementations of AI within them. But the truth is, like, what's the alternative?

1:08:24No rational person will ever build their own. And you don't hear that much about the day.ai's and all these like AI CRMs. Where are they at? We hear about all this massive acceleration of various application layer AI companies. We haven't had one of those zero to 50 in two years type of companies in go-to-market, and you really don't hear about the AI CRMs at all. In two years? What was the last zero to 50 you heard about in go-to-market? Ever? No, zero to 50 in its journey, like many, but I haven't heard of any of the go-to-market companies of this AI era having like crazy acceleration. Like one mine's done exceptionally well, but we haven't had a company that's shot from zero to a hundred million in 24 months.

1:09:10Like that hasn't happened in a go-to-market.

1:09:12Sam Jacobs: No, I don't know if it will. It won't. I will say I am bullish on SaaS. You know, I'm bullish on workflow tools that are going to use AI, but large enterprises still have a lot more than just the product features that they care about when it comes to using technology based on my experience. I want to shout out a couple of AI applications that I'm loving that go to market teams should be doing. Let's do it. I really do. Because there are things that we've been a little bit, you know, kind of like against a bunch of things here. Your sales demos should be amazing. Like think about if you build an application, okay, like you've seen these vibe coded projects.

1:09:54They're like 95 % good enough, but that last 5 % is really, really tough. So when you build an application and try to make it customer facing, you do need to support it, maintain it. There's bugs. There's all different types of things that become extremely difficult. But building a vibe coded, let's say application to do your sales demo, where it's like a captive audience, they kind of know the workarounds. It's not for like scale. Your demo should be incredible. I think one of the things I want to give a shout out to our team at ShipHero, we've like like Vibe Coded, the demo and something we call Sales Hub, it's unbelievable.

1:10:27It's like one of the best achievements I've seen the team do. And our demos are not only set up and personalized way faster, but they're excellent and they fit the flows of our prospective customers. Like that is an excellent use case because while it's customer facing, it's not being used by the customer. It doesn't need to match the rigor of performance capabilities of your core offering that's used by the customer. And then I think, you know, these FDE teams like that are coming up, like that is like, if you don't have FDE moving to go to market and being able to handle edge case requirements, then like that's the big miss.

1:11:05You now live in a world where edge case requirements, you should be able to say yes to more of them. But it does add complexity because now FDE teams and their relationship with core engineering, that's a communication thing, more humans interacting with each other. But the idea that your core offering can handle 90 % of what customers need and that you know how it is. Every business has all these edge case asks. To be able to say yes to them is an incredible unlock. And so each person, as you think about your org, what are the things that we're not going to build into our core offering, but we should be able to say yes to because we can put together an application that'll complement the core offering in some way.

1:11:49And then of course, like, like if people aren't prepared for calls now in a world where you can get all the information at your fingertips, your call prep, the research, like, like that's unacceptable now. Like we got to raise the bar on showing up to the call, having like done the right amount of research because it should be at your fingertips. And so orchestrating that research, like having a deal prep, having all that stuff. So, so these are just some of the examples that I've seen. And then use, of course, AI as a thought partner. Of course do that. But you own the output. Your name is behind it.

1:12:23It defines who you are. And when you send AI slop, I promise you, your recipient knows it.

1:12:29Sam Jacobs: I love that. That's a great ending point. Rick, thank you for being our guest. Thanks for teaching CRO school. We can't wait to see you at GTM in New York at the end of September. And AJ and Asit, it's wonderful to see you both. Folks, if you're listening, make sure you smash the subscribe button. Give us five stars wherever you rate your podcasts. And we hope to see you at Pavilion's GTM event in just over 40 days. Thanks, everybody.

1:13:03If 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.

1:13:35Thank you.