Speaker 1Cassie Young is a GP at Primary Venture Partners where she's helping direct investment for their new $625 million seed fund. After 15 years running GTM teams, she's now one of the sharpest operator turn investor voices in the go-to-market space.
Speaker 2There's actually like a reckoning coming for go-to-market leaders around we can't operate the way that we used to. The data that's really resonated with me is.
Speaker 1Cassie shares the most common gap she sees that undermines trust in a CRO and the exact framework you need to survive your next board meeting.
Speaker 2I think boards are done rewarding effort. You have to be able to articulate the direct hit of the piano.
Speaker 1Plus, Cassie issues a direct warning about the new technical baseline for the C-suite and outlines the new skill sets executives must have in 2026 and beyond.
Speaker 2I think that every executive needs to be able to. If there is any portfolio company that isn't taking. deeply seriously, we have a problem.
Speaker 1This episode is for you if you ever want to build a business. A more successful team, keep the trust of your investors, and outmaneuver your competition. Welcome to the Revenue Leadership Podcast. Today's guest is Cassie Young, who is a general partner at Primary Ventures Partners in New York. Cassie spent 15 years running go-to-market before becoming an investor. Most recently, she was the CRO at SailThru before its PE exit, then oversaw a $200 million MarTech roll-up at Marigold. Now, she is one of the sharpest operator turned investor voices in GTM strategy in the country. I'm sure you've seen a bunch of her writing and speaking around. And we're going to talk about a specific thesis of Cassie's today, which is the fact that GTM leaders need to become increasingly savvy about understanding and managing their P&L in a world where AI is significantly changing the economics of go-to-market. So tons and tons to dig into here. I'm really excited about this one. So thanks for joining,
Speaker 2Cassie. Thanks for having me, Kyle. I've, as you know, been a fan follower for a long time, so I'm thrilled to have the opportunity to come on and jam with you for a bit.
Speaker 1What did I miss in your background that is worth people knowing?
Speaker 2I think that summarized it well, but maybe one double-click I'll offer just sort of in the go-to-market background is that, you know, I've managed sales team, I've managed marketing teams, I've managed customer success teams, but I will be the first person to tell you that under no circumstances am I the best VP of sales, the best VP of marketing, the best VP of CS. But I think my operator career is that I had this exceptionally strong general manager brain. And it comes back to the central topic that we're going to talk about today around the P&L command, and that it was actually a superpower, right, in the ability to take on bigger roles, et cetera, combined, of course, with the ability to hire an amazing VP of sales, an amazing VP of CS, et cetera.
Speaker 1That is a profile we're going to see a lot more of over the next couple of years. Somebody who could think.
Speaker 2I mean, you and I, I think, have talked about this in the past, but, you know, as you see the convergence of these roles, I definitely think the generalist brain is having a moment. And that brain combined with the really strong business command will go a very, very long way.
Speaker 1You've talked about this thesis that the GTM bloat era is over. What do you mean by that? And how does it affect how CROs should be thinking about the world?
Speaker 2Sure. So the background on that statement was, if we think about traditional software, we were protected by rich gross margins, right? And so there was a lot of nonsense, for lack of a better word, that kind of happened in your operating expenses of the business, because you had that cushion and the float. In a world where companies have to invest in inference and compute because they're advancing their own products, we don't have that luxury anymore. And so my statement was that I think there's actually like a reckoning coming for go-to-market leaders around, we can't operate the way that we used to. The data that's really resonated with me is, if you look at the private company benchmarks around efficiency metrics, the one number that's gone up and to the right across every single revenue band over the past couple of years has been the ARR per employee number, right? But if you actually double-click, and I'm citing some of Iconic's most recent benchmarks just for reference for people on this, if you double-click into the go-to-market efficiency numbers, so specifically things like CAC payback, NetMagic number, they have been completely stagnant, if not, atrophying, you know what I mean, over the last couple of years. And so to me, I'm like, something's not lining up here where the organizations are expected to get more efficient on a headcount basis, but within go-to-market specifically, there actually haven't been, and I'm generalizing, of course, there are exceptions to this, right? There haven't been major structural gains on those metrics, and I just think that this is the time where there's going to be a reckoning between those two things. So when I say that I think the era of bloat is over, I think that we had a tolerance historically that our sellers weren't so spending all of their time selling, right? And the BDRs could do this many dials per week, et cetera, and that fundamentally we have to challenge all of those assumptions because I told a group of operators at an event on Monday, you're out of excuses. There's more creative ways to do this.
Speaker 1You're out of excuses is a popular refrain right now. Jason Lemkin's on our board, and I love the Thursday pod that it's Harry Stebbings, Jason, and Rory O'Driscoll, and he is beating this drum relentlessly. The Saster talk I did with him last year was in April, I think it was, and he said, you have until June. If your CRO is not AI-pilled by then, they got to go.
Speaker 2Well, I'll take it one step further for you. So I had mentioned to you earlier, I hosted this event for a bunch of senior women executives earlier this week with the Heavy Go-To-Market event, and I was once again preaching the gospel of how you have to be AI forward, and I started it by saying, this should be exciting to you because you get to tend to an ex yourself in a way that you never got to do before. This should be exciting. If I can't get you excited by the opportunity, I am totally cool resorting to scare tactics, and the scare tactics are, number one, you're out of excuses with your board, right, because it's the expectation. Number two, the example I gave them, which I think scared the crap out of everybody in the room, was I showed them this Claude prompt I had written, and this is an event series that more than 600 women have come to. I fed Claude the list of every woman who's ever attended the event. And I basically fed it a score that I called an elite score. And I said, I want you to rank these executives based on a number of criteria that I fed it around, the company profiles, the growth, the role, et cetera. And I said, that's what's happening in the market right now, right? And I said, I'm using this as an illustrative example of if companies have reputations for what they're doing. And I asked Claude to give me the logic, by the way, of why it rated every person, and it did. And I'm like, you're going to be exposed, you know what I mean, if you're not sort of leading in this. And I think that was sort of a shot heard around the world moment for people in that room.
Speaker 1I love that. You should open source that so people can score themselves. How elite am I? It's actually a great, yeah, it's a great lead gen, network lead gen for me, baby. Yeah, there you go. If you can vibe code it in the next week and a half, we'll put it in the show notes. Exactly, got it. Noted, yeah. One of these like scared straight tactics or frameworks that I share, and it applies to revenue leaders. I was just talking to RevOps consultant who's super sharp, and it's applicable to that space or like healthcare or hopefully education, is that AI is really going to be the death of the administrator and the rise of the orchestrator. And it's sort of a cliched saying, but I think it's a good framework to say like, if you're viewing your job and the tasks you do day to day are administrative in nature, if it's, you know, just like rolling up a forecast and taking information from one place to another, it's going to be a lot more complicated than if you're doing it from one place and giving it to another. Like if you're a middle manager, and a lot of your job is to just like manicure a forecast and then talk to a bunch of people, and then give that to somebody else. Or if your job is to make sure, like if you're standing in front of a customer, and you're just intaking information to put it into a system so that it could go somewhere else, like those jobs should go away. Because AI can do them so well. But you know, the people who should be excited and the people who will be successful can think systematically and orchestrate with all of these incredible new tools, and see their value go up 10x in the market.
Speaker 2Yeah, for sure. And there was an interesting piece, I don't know if you saw it by another New York VC at Slow Ventures a couple weeks ago, that was written a little bit satirically, but it went quite viral. Because he said, in the future, there's basically only going to be four jobs, right? Oh, yeah, I did see this. Basically, for people who didn't see it, number one, and he meant this in an endearing way, right? It was like the AI slop cannon, but he actually meant the people who are like building all these agents and very fluent in the tools. The second was, you know, the folks who are going to be responsible for all the fun, like cybersecurity, SRE, etc, that comes out of that. The third, where there's hope for all of us, right, is the adults, right? And you have this crystallized knowledge, you know what I mean, where you have taste, and you have judgment, and you can apply that. And then the fourth was like his very funny bucket, which he just called hot people, right? Where he said, you know, we're going to eat like these sales and customer facing people to make business happen. But that's a long winded way of kind of agreeing with what you're saying, right? Where there are these sort of core jobs to be done. And anything that kind of sits at the intersection or the connected tissue is just not going to be needed from humans.
Speaker 1And I, you know, it's satire, but there are a lot of kernels of truth in it.
Speaker 2And I think that's why it went viral, right? Because there are absolutely kernels of truth. And I had read this article, I don't know, a couple of months ago, it was actually specific to venture capital, but I actually think there's broad applications in other industries. It was a data-driven VC. And it was asking this question of what is the future of VC? see org chart look like. And really what they had put forward was you have these supercharged juniors, do you know what I mean, who are managing all of these agents, et cetera, but that you need junior people because it's an apprenticeship model and you need a bench for talent. And then you have dealmakers. And when I read that article, I actually think that's the same in many other industries because people talk about things like legal tech. And I think about large law firms. I have many friends who are partners at large law firms. Their job is to be dealmakers, right? You know, to go out and sort of go get these clients, et cetera. And so I do think you're seeing a convergence around a number of these key themes around where is human oversight actually quite beneficial and required when it comes to doing business.
Speaker 1The 20VC episode with Aaron Levy, I think it's really interesting on this. I actually haven't listened to that,
Speaker 2but that's good for work for me.
Speaker 1I listened to it in the gym this morning and that's where this like administrator versus orchestrator mental model came from because he was talking specifically about legal. That Aaron Levy is the founder and CEO of Box, super cracked and on the cutting edge of all things AI, really, really sharp thinker, especially when it comes to enterprise. And so what he was sharing is that he actually thinks there'll be more lawyers, not less. It's like if you give everybody a pocket AI lawyer that are producing all of these legal situations and questions, then you could argue that those people will need more human lawyers because there's more legal documents. Being produced and memos. But he did call out this apprenticeship model comes under fire because those apprentice level jobs, whether it's an analyst at a venture company or in a legal practice or wherever it might be, they will not be nearly as required because you can do so much of it with your AI tools.
Speaker 2And for what it's worth, I mean, I subscribe to all that. And I think that particular piece he mentioned around the expansion of supply that I can remember from past episodes, you've talked about like the Jevons paradox, but we massively subscribe to that at primary, right? Where it's like you look through history and as things have become more available, more efficient, right? More affordable, like it absolutely increases demand. I think this will be no exception to that.
Speaker 1And for listeners who maybe haven't read or heard me talk about this, Jevons paradox is basically the concept that as something becomes less expensive, it becomes more expensive. And so I think that's a really good point. I think that's a really good point. People don't spend the same, use the same and spend less. They actually up their spend. And so they might spend more than their original amount, which is like now considerably more because the cost has gone down. And I relate that back to engineering. And I think if you want to know where any job is going to go, just look at software engineering because that's the market that has been most touched by AI. And there are more engineering roles posted than ever. And it is harder than ever to hire engineers because if you're, you know, for us, we are shipping four times the number of PRs per engineer today than we were 12 months ago. And we're not saying, okay, great. Like, you know, we only need half the engineers and we'll accomplish the same. No, no, no.
Speaker 2It is such an important framing, Kyle, because I feel like the world has gone down this rabbit hole of like, we can cut all these roles, right? And I tend to come at it from the lens of like, undoubtedly there is bloat, as we talked about before. But I get very excited about thinking about what you just mentioned, which is what happens when we get to 10x every employee who's in this organization, right? That's like certainly how we think about it at primary. We're not an operating company, but we bring that same lens to the portfolio companies because it's ridiculously exciting, you know what I mean, in terms of the clip that you get. So it's, I think everyone kind of goes toward this, oh, you get like strip out 20% of the headcount, et cetera. And to be clear, there are places where that makes sense to go and do it. But I think we often don't spend enough time talking about the other side of that equation of what it does in terms of accelerating revenue, et cetera.
Speaker 1Yeah. Yeah. Even like our BDR organization has grown in efficiency and productivity like drastically over the last little while, thanks to AI. I'm pulling forward headcount now from like four, from our model four months out. I was like, well, the economics are incredible. Like, let's just do more of this. Let's just grow faster. And because our CAC payback pencils out, really nicely, like we can go do this. And I think this, this is the piece that people miss is that they just assume companies are going to pocket the difference, but there's also the competitive dynamic. If your competitors are the same amount, more effective, they're not, they're not going to ship the same with fewer people. They're going to ship more with more people. For sure.
Speaker 2For sure. And I'll even offer from like a venture lens, you know, a metric we pay a lot of attention to is burn multiple. So people are new to that, right? It's basically for, you know, every net dollar of cash burn, how many dollars of ARR do you bring into the business? And, you know, for scaled companies, there are very tried and true benchmarks around what you want to look for. Like obviously anything less than one is amazing. Like up to two is like fine. And when you're north of three, it's like, what's the, that's the kind of thing. But the exception, the reason I bring it up right now is, you know, our first check-in at primary is at seed. And so it is not uncommon at all that we would work with founders that have crazy looking burn multiples in year one, because it allows them to establish this early mover advantage. But the operative part of that is they have a plan to bring it down, but it's very common, you know what I mean? That they would be investing in R and D ahead of commercialization, right? Or even once they are selling that they really want to keep pace with the roadmap. And so there's so much nuance, you know what I mean? In all of these numbers, even in the AI or in terms of like the context is everything around them.
Speaker 1What stage do you think burn multiple starts to be like a more thoughtful heuristic? I
Speaker 2think, you know, historically I would have said like, we'd start looking with like a very, very solid eye at the series A. However, the series A's are happening like a lot sooner than ever before. So I would say we're looking at it, you know what I mean? Like I think it's in the series A portfolio company board meetings that I'm in, but I think there's a much more critical eye to it on the other side of the beat. Now the difference, that's burn multiple specifically, metrics that are happening earlier than they did show up are metrics like revenue per employee, right? When I started at primary, I never would have seen that metric in a series A board deck. And there's not necessarily an expectation around it right now, but it's like everyone has the efficiency of their build on their mind. So it's showing up earlier and earlier. I also think that investors are paying a little bit more due to some of the retention figures early, right? And we know that the companies you sell to in your early days of building eventually, like they're not going to be the perfect ICP that's going to evolve. It's in a later stage board meeting and see net retention broken out in two lines, right? Like current ICP of our legacy customers. Right now with all of this talk of experimental revenue, people definitely are looking at what's happening with like the growth in net retention early on, because you're alleging that this is your ICP right now, right? Do you have an ability to protect the base? Because usually what happens is people sign up as these early customers and it takes a little while for them to learn that they weren't the right customers. But in the end, it's just evidence, you know what I mean? That supports it that way.
Speaker 1How are you thinking about where do you invest today in a world where the foundation model keeps eating so much? Like Claude Design is the perfect example. Claude now chews into a bunch of, you know, what Figma is trying to do. And, you know, there's, I think Figma went, I think Figma lost like 7% of their market cap the day it was launched. And, you know, you see this every few months, like, you know, managed agents came out and killed a bunch of startups and dispatch, and like, you know, all of these, there's so many of these launches that kill a category, not kill a category, but impact a category. And so how do you think about where to invest the foundation model?
Speaker 2So first of all, this is like the question of the hour, do you know what I mean? So we're concentrating this with every new deal that we see, do you know what I mean? That's vertical specific in some ways. So I'm going to take the question in two different directions. So one is like the category, and then second is sort of what's sort of the product strategy, because, you know, at this point, this is probably, you know, well stood. When we hear about like the SaaSpocalypse and what's happening, I don't worry as much around the DIY vibe coding risks, do you know what I mean? For like the full platforms, like when people say they're going to vibe code their own CRM, I kind of roll my eyes and I'm like, that's going to work in mid market and enterprise until there's the first massive major security breach, do you know what I mean? Like, everyone wants a throat to choke. But where I think there's extreme risk in that category are like the classical point solutions. And where that gets messy for startups is everyone has to start for the most part, do you know what I mean? As like a point solution or a wedge. And so it's like, how do you earn the right that you're accelerating the product map, a roadmap quickly enough to make this compound startup view that you don't become at risk for that replacement. So I want to just make that comment. It's not specific to a category, but I think a lot around this, like, what is your point solution to platform playbook and plan? And like, how do we get highly in what that looks like? And what is your right to do it? On the category specific? I mean, I think the question we ask ourselves is, there are categories where people want things that are purpose built for their domains, right? And you hear a lot of this chatter around what's probabilistic versus deterministic. So I'll give you an example. We're investors in a company called Mayburn, now sort of a series B company in the fintech space. That's really challenging, you know, fund accounting and administration software. You cannot make a mistake in that business. Like you can't make a mistake with capital calls, right? And that's a business that's still managed in Excel, believe it or not, right? And there's solutions that do part of it, but they're underwhelming and have low NPS. And so that's a category where we're like, that needs to be taken down. Here's another one. I'm an investor in a company called Lyric that's in the enterprise supply chain AI world. That is a math game. So when you think about decision science for supply chain, 70% of the reasoning that goes into it is actually operations research expertise. And so yes, maybe at some point, you know what I mean? The horizontal players are going to go after it. But the way that I think about that is, okay, right now that company Lyric has access to all those same models and they've got 200 people working there, you know what I mean? With that expertise to go and do it. So that's type of the framing. I think the more interesting one in the world that you and I live in is like, we talk about businesses like OneMind. That's one, because people ask me about it all the time. I'm like, listen, revenue leaders want stuff that's built for that. Like at the end of the day for their job, the customer is really high stakes. And so to the naked eye, people are like, oh, I'm engaged with the customer. But when you know, like when your butt is on the line, you know what I mean? For sort of delivering, converting those leads, expanding them, you want something that's very trained. So that tends to be the framework for how we think about it is like, really, how do you get to know the buyer and the customer and really what the demands and the specificity are? We sort of get comfortable or don't get comfortable with it that way.
Speaker 1And so is this changing the way that you're thinking about investing or doing diligence? Or is it more of the same as maybe what you would have done pre-AI?
Speaker 2I'm going to give you like a very specific example. So I met this company a few months ago, and it was this like major eye-opening moment for me because it was the first time where I thought to myself, I probably would have invested in this company a year ago, and I'm passing on it now. And I'll walk you through kind of like, I'm not going to get into the specifics of the company, but the contours of the diligence process, because I think it'll be revealing. This was a company where the founders were. Just absolutely lovable. Do you know what I mean? Like just absolutely really, really fantastic team. My initial test with any business is like, one, do I like a problem statement? But then second, how quickly do my diligence nodes get back to me? Right? Because if I have to chase them for a second email, I'm like, this isn't a hair on fire problem. You know what I mean? Because if it is a hair on fire problem, they're going to be like, I want to learn more about this. And this was one where like, I went seven for seven on a Thursday night. Of getting people in my network to take the demos.
Speaker 1And diligence notes, just explain. For people, what you mean by diligence notes?
Speaker 2Yeah. So a diligence note is these are people in my network who are potential buyers of this solution. And we primary, you know, we use our own network and then we, of course, cast a wide net so that we have a balanced perspective. But this particular business was building in a category where I'm like, I know some really good buyers for this product, so I'm going to like use the backbone, right? I'm going to call them. And the feedback from almost unanimously from them was like, wow, this is really cool. And I would try this. I think this is probably something we could ultimately do with Claude. But, and I. I had this moment of like, this company is going to get ARR traction, but I don't know what's going to happen on the other side of it. Yeah. And I think that's the tension that we have to wrestle with right now is, and that's, I think, the question, like to your point about process, it's just going even deeper with the customers to understand like what's happening in their organizations and like what are their own roadmaps look like? How are they thinking of Dubai versus Build? But that was, I actually made a point of bringing that example up with my partners because I was like, guys, this is the first. This is the first time that I really had a stop in the tracks moment of, wow, like something has changed in terms of how we're evaluating things.
Speaker 1And is it a category that's close to engineering or, or like, why was it that you, that that felt like, oh, it's susceptible to.
Speaker 2It was, it felt like a problem that if you solved it, if you, if you solve the core business value proposition a few times, you could probably use a horizontal solution. To train it with your own sort of business. No, I'm on it.
Speaker 1Yeah. Okay. Momentum is a powerful tool for turning sales and customer conversations into go-to-market intelligence using gen AI. It extracts analyzes and automates customer intelligence across your GTM org. The best part, it's not a new platform for your team to adopt. It integrates seamlessly with your existing stack, or it can straight up replace your conversational intelligence tool at owner. We ripped out gong and one all in on momentum. It writes back to our Salesforce directly. Captures forecast. Insurance. Risk auto-fill CRM fields, shares, product signals, and tracks sentiment companies like cursor Z scaler ramp and 11 labs use it every day. Check it out with a free trial at momentum.io. I want to, I want to switch gears and now talk more about what CROs need to do in this world. So maybe just like lay out the thesis we touched, we touched on a little bit of the, this reckoning, but just touch on like how AI changes, how a CRO needs to operate from a macro perspective and this P and L through Lindsay, uh, idea. And then we are, I'm going to break it down.
Speaker 2Yeah, absolutely. So we'll let's start very, very macro. So, you know, at the end of the day, we talk about the board metrics that matter, right? We're always talking about growth, you know, for years, everyone was turning back the clock, the 2015 and the battery T two D three, the triple, triple, double, double, double. And now everyone's like, that doesn't even matter anymore. And you've got companies are actually growing at an even faster clip than that. I bring that up because at the end. Revenue leaders, that is still the tip of the spear for what they need to go and do, but it's not enough on its own anymore, right? Because as we said, in traditional software, you are protected right by these 80% gross margins. And when I say protected, let's like double click on an example. Let's use pricing. So then pricing is having a real moment right now in a role of 80% gross margins where it functionally meant like the cost of bringing on incremental customer just wasn't that material. If you messed up pricing, like. Look, it wasn't that consequential, do I mean for any particular what customer, if you do that today, do you know what I mean? In terms of what I tell people is, you know, you forget that every magical feature, every new agent has insane inference costs that come along. So if you charge too little, you are functionally paying customers to use your product. But on the flip side, if you charge too much in this extremely competitive environment, your competitors are going to eat your lunch, do you have any, because they're going to figure it out before you do. And so I think the first thing the CRO has to understand is like you're, suddenly your pricing is actually becoming a huge part of your business strategy, right? As you sort of work through that. And I think that's why you see the rise of sort of consumption based pricing, et cetera. That's more tightly aligned to that. But I think that the next thing we have to think about is what is the cascading effect on the metrics that matter? And I don't have perfect answers to this, but I'll tell you some of the questions that are on my mind. In a world historically where sales compensation. Is done on ARR and we have wildly different gross margin profiles for businesses. That suddenly doesn't feel so good anymore. Like in a business that's fundamentally like you're making 30% gross margins, like that mask going to break down. And so it's funny, Kyle Poyer put out a piece a couple of weeks ago around, he kind of came up with this set of like what he was positioning as the new AI native metrics where he talked about things like, you know, gross profit on token consumption and things like that. But I think there is this bigger question. The question of as you, as the revenue leader, do you need to sanity check the bath of the function? Because in a world where you're fully loaded commission expense was 25 or 30% of what you're bringing in, but what you're bringing in has now been watered down by 50%. That's going to get problematic very, very quickly. So that's my overall frame is like the contours of the P and L are changing drastically. And the CRO has to understand what that is and there aren't perfect solutions yet, but I think. Having that partnership with the CFO to be asking the intellectually honest questions around as the bath math is an incumbent on, on every great go to market leader.
Speaker 1We talked about the macro changing the board metrics that matter. And so the, the pressure that CROs will feel is what from the board.
Speaker 2So I think boards are done rewarding effort and want to see impact and let's go through some examples of that. I mean, I think when people talk about efforts, like these are the tools we're using. These are like the incremental gains where, you know, maybe this is, you know, what the coverage rate is of the BDR now is how many connects we're getting. Don't mishear me. Like those are fine leading indicators of where the business is going. But I think again, because of this pressure of like, we can't benefit on the margins that we have to get smarter around how we're managing our operating expenses. You have to be able to articulate the direct hit on the piano. So the example I give people, and I'm not trying to pick on like digital deal rooms, but I tend to always use this as fine example for better or for worse. It's like, okay, if you're the CRO and you're talking about invested in this digital deal room and it's great because now we kind of cut a couple of days off our sales cycle. And when we cut a couple of days off our sales cycle, now let me walk you through the three layers of math that work out to the incremental gain that I get per year. That's too much math for the board, right? I really believe that it has to be like, what are these direct line impacts? And so I, I tend to talk about it. I, I sort of coined this acronym that I call the prime framework and it's P is productivity. R is retention. We'll come back to these in a minute of what I specifically, I mean, I is investment efficiency. M is momentum and E is expense reduction. And I'm not saying you need to do all of them, but my hack for CROs is like, you got to be able to align what you're doing up and into one of those, right? When you're talking about this. So when I think about productivity, I do like revenue per employee is a good, that now, by the way, that's also a metric that we could question because ARR per employee, if you only have 30% gross margin, it's different than ARR per employee. and you have 80, but put that aside for a moment.
Speaker 1And employees have a very broad range of cost, you know, like ARR per, if you have an entire company of 500K a year, engineers is a little different than, oh, we've got some people in Latin America, we've got offshore, we've got some cheap EVRs.
Speaker 2Yeah. You'll like Kyle's piece because one of the metrics he talks about, I think, is ARR per headcount dollar. I can't remember if it was ARR or another metric, but he talks about normalizing it per headcount dollar, which I like.
Speaker 1We're talking about this internally right now, because close to half of my team is in LATAM, and then, you know, another 40% is in Canada, and so it's not like for like to a fully burdened U.S. headcount, like in many of the companies that investors may benchmark
Speaker 2us against. Yeah, that makes sense. That makes sense, yeah. So revenue per employee.
Speaker 1Yeah, revenue per employee.
Speaker 2On the retention side, I just mean net retention or gross retention. Nothing cute about like. Like the customer's happier. Like does it keep them and does it grow them? On the investment efficiency, that's when I start to think about metrics that I alluded to at the top of the hour around sort of net magic number, right? CAC payback, but like it's very evident in sort of the board flash metrics, right, as we see them. Momentum is where I talk about top line growth, right? Because that, of course, is very, very important. And then expense reduction is, you know, self-evident, right? And how do we take costs out? But as you and I said a bit ago, Kyle, like. To me, that's not the be all end all. That's one option of many different things you could do. And so when I'm looking at go-to-market solutions to invest in, I won't touch it if it's not obvious to me that it doesn't hit one of those five things like pretty immediately, if not multiple. And so as I think about that as an investor framework, my call to action for CROs has been I might think about that as a buyer framework, do you know what I mean, in terms of the things that are going to stick around. Because I do think it's like it's great that people are adopting stuff, but that's now. As we said, like everyone's had excuses. That's the baseline expectation. It's what are you doing with it? My experience with some exceptions, your present company included in those exceptions, has been not everyone is thinking that way. And for those folks who didn't read the top line piece that I put out about this, I asked Kyle to give me some data because I said, I'm going to go to some of the more AI native CROs that I know because I think that I appreciate that you guys are leading by example, right, in terms of this is how we're partnering with our CFO. And I think that needs to become the norm. But right now, I think those are more the exception cases.
Speaker 1Yeah, we are definitely hyper focused on because so we have an incredible AI leader for sales, YG, who, you know, when we talk through his projects, I'm going to just use Prime, I like it as a as a framework, we are constantly coming back to like, what is the thing that's going to bring in more dollars, it's really, it's really about growth. Yeah, we're trying to streamline stuff, but we're streamlining things so that reps can do more revenue generating activities, it's not really a cost reduction play.
Speaker 2I also think this education has to happen, like across companies, joy, but I really I'm a huge believer in sort of transparency and education. And, you know, I think it's a lot of times very easy for employees, particularly individual contributors to be like, why, you know, are the goalposts changing, etc. and understanding this context around the world of businesses change, like fundamentally, business models are not what they were is extremely important context. And I think it's incumbent on the leaders to make sure their teams understand that.
Speaker 1Something that I've, you know, my team is sick of me sick of me saying is like, there's a there's a gravitational force within quotas, they only go up, like that's the only direction and when quotas start going down, like that's when you should be worried. You know, we capture some of the efficiency in quota increases, but a lot of the efficiency we we share with the rep, and just let them smoke their number.
Speaker 2And it's funny you say that, because when I hear that, right, and I, you know, it's been now six and a half years since I've been on the operating side, but I'm always like, what a privilege that you get to work in a place, do you know what I mean? Where you have this ability to hit these crazy numbers, you know what I mean, because of the product, yeah.
Speaker 1I think our average outbound BDR last month produced 10k in close one ARR, or close one MRR. Wow. So like 120k in close one ARR per person. And it was, you know. You know, not too long ago, three and a half K and at three and a half K, the economics were fine, you know, like you, you could, you could make it work, but at, at one point it was six, then seven. And, and last month we, we, a lot of things went right, but this business is completely different because of, because of those AI investments. But why, why do you think that companies aren't getting the return though? So they're doing AI stuff. Is it, they're solving the wrong problems. It's the wrong tool. Like. What's the gap when, when you talk to people.
Speaker 2I mean, I think this is very organized organization dependent, but there's like a number of different patterns I've seen and, and some are all maybe true. Right. So, uh, the first is like, I think there's just insane sprawl around initiatives. So it's like, we're trying 50 things, maybe, or maybe not. There's a clear owner on what those are. There's clear objectives of what we're trying to achieve. And I think like one of the downsides of letting everybody experiment during minutes, you just end up with. You know, you're not going to be able to do it. You're not going to be able to do it. but they also sort of have a hue, right, of things they can look at and sort of assist it but your point on like how they coexist you know i tend to be like you know the the uh number one sort of fangirl the old charlie munger quote you know i mean like show me the incentive i'll show you the outcome and i go back to this like and i'm not talking about token maxing to be clear but i do think there it's like in the performance rubric there needs to be do you know i mean some assessment of what people are doing and what they're building but i when i hear about these like leaderboards of tokens i'm like you gotta be kidding me you know yeah it's like the classic right of like i'm just gonna like book a ton of meetings you know what i mean it doesn't matter what happens with them
Speaker 1yeah yeah so i i just want to uh keep picking it at like where companies are struggling so initiative sprawl not being clear maybe not picking the right things org design certainly is an issue any do you think there are any other drivers that are leading to people sort of like deploying ai stuff and just like having it fizzle or not get the results they want some of it
Speaker 2i mean i think there's a lot of people who invest in these tools but i look at when i was operating i always used to joke with my implementation team like phase two never happens you know i mean like just get over it so i think there's a lot of people who invest in these tools but i look at when i was operating i always used to joke with my implementation team like phase two never happens you know i mean like just get over it so i think there's a lot of people who invest in these tools it doesn't happen now it's not happening and we're going to turn the customer right so you have to kind of redefine the milestones of what this is but one trend i've observed in our portfolio companies on the vendor side so not as the buyers but i think it pertains to the buyers is some of them are moving implementation under product and i don't know if that's going to be like a long-term trend or it's a temporary thing while we navigate what's so the thing you and i are talking about which is the customers don't see the value it's so easy for the tool that's slightly better implemented that launches the new feature to come in and tangentially take that share of wallet and so i think there's a lot of that where you know you you end up buying a lot of stuff but you're it kind of goes back to the sprawl again like you're not fully invested in any one of those tools you know i mean as you as you go and do it but i'm going to be very blunt with you going back to this thesis like i will tell you like i meet a ton of sierras on like interviewing people for our portfolio companies and stuff like that a lot of them like don't understand the pnl like i i have gone on the record saying this like sam and i have been talking about it for for years at pavilion like and he now does the pnl like fluency command because i'm like people suck at this like it's actually really bad not to like make it an easy throwaway comment like i think a lot of people don't know how to articulate this story and so even in places where it may be happening so my number one hack for cro's is like you better be taking your cfo to lunch you know what i mean like you're not going to be taking your cfo to lunch you know what i mean because you need to understand where they're being pushed and how to speak their language i mean and how they're thinking about the function because i worry that even in places where maybe this is happening people just like fundamentally don't get how to tell that narrative arc do i mean around what's actually going
Speaker 1on beyond going to lunch like seeing your cfo as a partner and not the obstacle like so much of the time it's like okay my sierra my cfo is going to tell me no on the headcount i want and no on the the thing i want to buy and they're going to push back and you just get into it and you're going to be like oh my god i'm going to be like oh my god to this very like binary place as opposed to saying like all right i need to go make that person a partner and when they tell me no like okay why hey help me understand like why do you look at this and say no and not in the objection handling way which i know we do sometimes but in the like deeply inquisitive like walk me through like your logic to to say x y and z and that's you can start getting there yeah yeah and the
Speaker 2final point that i'd be remiss if we didn't hit on is i think elena vera at um lovable has done some good writing on this around how like executives need to be vibe coding do you mean they like need to be in the tools and i still think there's like wild dispersion in terms of what's actually happening right like you you and i are getting on and you're you're telling me you know what i mean like you've got all your agents running for you etc which is amazing i do still think there are people who are like removed from the work and you have to use the tools right because your imagination will run wild for your own team do you know i mean as you go and and do that and i i'll offer myself like as a personal example i mean i feel like for months i'm like i i have to carve out more space do you mean to like get into cloud code and i remember at one point i was like i'm just devoting a saturday to this because like i am not going to get better at it i mean that's why i go and do it i think again this is a place where every leader has to invest the time because it's going to open their aperture for what's possible how to storytell how to push etc
Speaker 1i want to start asking people to just show me their their cloud usage just like hey open up your cloud settings click on usage and i want to see how many tokens you've spent this this month and it's you know it's not to get to the token maxing thing or or or be reductive but if you are on the pro plan and you've spent 14 of your your monthly budget then it leads me to believe you're just in there asking for recipe ideas and having it rewrite your emails i mean
Speaker 2another way to flip that to definitely done for people is like what had been like the three most like transformational professional leverage things you've done in it you know what i mean because that you know i mean like i think that's like an interesting question of like different people push themselves in other ways of like where'd you get super creative right with the and again when i asked people that question i i get great ideas you know i mean in terms of like things i do and for me it's been like look i always deal with this example like i live and die now by this like daily briefing i get every morning at 9 15 that basically tells me all this stuff that i like said and i'm like i'm not in different channels i said i was gonna do it yeah like it was reminding me like i'm recruiting this speaker for an event in june this morning that on a zoom call we had last friday i said i was gonna send her the recording for like this back stuff and it's silly stuff like that where i'm like again it's it's i'm like 10xing myself where i'm like oh i look on my game do you know what i mean because it's like not and i think i was like pretty on top of not letting things like fall through the cracks to me it's like i'm picking on that as a very microcosmic example but when you think about you have 20 workflows like that that run every single day like you can imagine for me like portfolio company management you know it's all of the stuff that comes back to be relevant news around those industries like it's crazy like the ability to synthesize all this stuff in one
Speaker 1place yeah i have something similar and and honestly it's overwhelming i was like this is the amount of stuff that i've said i would do in you know in a in a day i was like that's why i have to run
Speaker 2it every day because i have every week i tell it was on friday so because the first time so i
Speaker 1rebuilt my open claw from scratch a couple weeks ago then it was so it updates my notion task list and so it ran it it ran it after this week and then i had like 40 tasks it's like oh something's broken it must be doing duplicate things and i started reading them it's like no like actually every single one of them was like either some slack message i had to send or i needed to do some email intro and then i've started to try to build now so kai is my ai chief of staff kai and kai has his own email and kai has is a slack bot as well and so i'm i'm now trying to build the second layer to for it to just go do like execute all those tasks and that has been shakier so you're gonna after the podcast you'll get a follow-up from kai that will have the episode a bunch of the a bunch of assets and it's gonna write it's gonna write uh five linkedin posts for you in your own voice so it'll go scrape what you've written and it'll my
Speaker 2linkedin post yeah i love that
Speaker 1linkedin's tougher i haven't been able to figure out how to scrape linkedin yeah um but but like your newsletter stuff and it'll take your tone of voice from this recording and write some stuff and send it so you'll you can give me some critiques on critique on it because it's only happened a couple times but i've similar
Speaker 2had that issue with linkedin by the way i think i saw you we jumped on i was just like um doing i write it for me and same thing but i'm like now i've just fed it like good old-fashioned like here's like the copy paste of like 20 things from the past just like use it you know what i mean and it's like it's pretty good yeah
Speaker 1so my open claw is in a virtual machine in digital ocean and so because i just don't want it on my like work computer yeah we
Speaker 2don't we we do not have that at primaries okay in any business i think it's hard like particularly with the sensitivity of all the portfolio companies it's like a little mind-boggling yeah
Speaker 1yeah yeah and so i'm still wading through how to build the right system of action and and um that's the next layer and i think like that will be the biggest unlock because then it's like getting actual things done like right now i'm still sort of the assistant to my chief of staff sometimes sending the slack messages and doing and doing whatever but this but this is the big architecture challenge going back to one of this this sort of central versus decentral conversation is in the conversation if somebody could build this shared infrastructure with you know the context graph and a baseline set of skills that then you could plug into and enough safety built around it so it's not going to like nuke a bunch of salesforce records or share stuff but um this is this is i think one of the questions that is still unanswered and unresolved uh that i'm eager to how are boards measuring cro's differently now so we talked about the p l fluency they want to see results not just like effort but are you you really are you measuring a cro on like whether or not they vibe coded their own their own thing or like how do you think about measuring a cro differently in this world i mean i think it's
Speaker 2about at the end of the day it's always going to be about outcomes during the business so the first thing is like nothing really matters if you aren't hitting a plan you know i mean so we're that that hasn't changed and that's not going to change right but i think what i'm listening for are are sort of the stories of what's happening in the business and where i lose interest is just like incremental anecdotes do you know what i mean versus these tales of like transformation in the function and and how it's working and what that's like right so when we like i always love hearing the examples of like the super creative go-to-market engineering unlocks that they've like figured out for their particular business so i'm i'm listening for those stories versus the like we tested these two things do you know what i mean we had a percent gain when we did blah blah it's the richness of the anecdotes and so what what's the difference between the two things that we're talking about and what's the difference between the two things that we're talking about and what's the difference between the two things that we're talking about and what's the difference between the two things and what's the difference between the two things that we're talking about and what's the difference between the two things that we're talking about and what's the difference between the two things that we're talking about and what's the difference between the two things that
Speaker 1we're talking about and what's the difference between the two things that
Speaker 2we're talking about and what's the difference between the two things that we're talking about and what's the difference between the two things that we're talking about and what's the difference repair?
Speaker 1between the two things that we're talking about and what's the difference between the two things that we're talking about?
Speaker 2I'm not saying that you need to go and run your whole life through agents, but I think that baseline, like you've been a consumer of the tools, you know where people get stuck, you know where things get rate limited, like that's not only important for setting an example for the team of what's possible. Again, every product has to think about this. So if you're in a sales role, you just have to understand it.
Speaker 1And I think it is such a different way of working and the assumptions are so different now that unless you're in it, I'll say day to day, like maybe you can get away. With like weekly, but you just won't build a native understanding of the of the primitives and of like the first principles, even just simple stuff like, you know, I was I've spent, I don't know, 10 to 15 hours building this XDR hiring analysis. And at one point, I was like getting stuck and I was spinning on it. And I was like, Okay, I just I need to start in a fresh context window, like I needed to move into a new terminal window and start again. Because like, you know, the context gets all garbled, and then you just can't make it. progress. But even that thing was built on enough understanding of the way these chats or these ways, the way these things, interactions work, it's like every single token above you in that conversation is pulled into the context window to answer your thing. So because I was I was like, first connecting data sources from a bunch of different places. And then I was having having to like groom the data. And we had to go through like this process. And so by the time I was having a do like a bunch of different types of analyses, it was like confusing them all. And, but starting fresh, as like, it really started working. And then I could run that I ran like the Carpathia auto research thing on it. And even that, like is because I'm on Twitter. And like, I was like, Ooh, auto research, because I have output data and input data, auto research could could do this sort of like synthetic analysis. And, and I just don't know how you make great decisions about how you build your go to market org, and be a good partner to your product teams, if you don't understand some of those primitives, and maybe you don't have to go as deep as I did. But like, I sort of think you do.
Speaker 2When I first started taking with it, I sucked at it. Yeah, I'm like, what is taking so long? You know, like, and I would actually ask why that takes so long. And it's like, well, these are five things you massively screwed up, you know, they want you just sit and even feedback mechanism, do you mean is I'm like, Oh, and it frames your way of thinking even around how like a customer would use your product. And I mean, like, I think there's just such a transitive properties, you know, I mean, of sort of being in the tools and how your customer would be using using these tools. But I agree with you, I think it's immensely powerful. And I do think you brought up an interesting point when you said like, on Twitter, I'm in these places. And I think like, it's always so important for executives to be sort of activating their networks. This is a time where that is like, so critically important, because that's where you get ideas. I mean, you're kind of out there talking to people, even if it's not like for like, for your business, you're going to say something that triggers something in my brain that even though I'm in a very different business, right, it's going to get me thinking about a problem in a different way. And so I think it's always been important that people are, you know, leveraging the professional networks that they have at their disposal. But I think it's especially important right now.
Speaker 1Like, I spent a lot of time with our product team here, and I'm constantly hitting them with questions. And I think I plug Lenny's podcast, like every three podcasts, but I'm going to do it again. Like, read Lenny's newsletter, like listen to that podcast, because he is so inquisitive and curious, like he makes it approachable. And not every episode, like some of the episodes are going to go way into product management. But there's a bunch of them where they talk about AI strategy and how it's transforming organizations that is the most readily applicable. And like I said, Yeah, like engineering and product are on the forefront of this. All of the things that are happening there, all the challenges, all the opportunities, they're going to be similar that we're going to be dealing with in, I don't know, quarters or years from now. How else does a CRO need to evolve this like P&L understanding? So we've talked generally about become friends with your CFO, get inquisitive about how they're operating. But like, what are the pillars or like foundations that a CRO or a CMO you know, need to go like add their toolkit? How would they think about building this new skill?
Speaker 2I have this framework that I use for every executive on the planet in terms of what I think separates the best from all of the rest. And I think the best are not, it's not a huge sample size, right? And I call it sort of the core four attributes, right? And the core four attributes, which are going to really reflect nicely on some of the stuff we've been talking about. The first is P&L, fluency, and command. We'll come back to that again in a minute. The second is this concept of first team thinking that I've borrowed from Pat Lencioni, who wrote books like Five Dysfunctions of a Team. If people are new to it, the idea is your first team is the most senior team you've sit on. It's your peers, not your direct reports, such that you always put the business above your swiveling. Go-to-market leaders are very, very bad at violating that. It's a reason we had the highest median executive turnover rates. Usually number two is heavy. Third is this pulse on macro. So you are constantly rewriting your own playbook and narrative based on what's happening in the market. And then fourth is the strategic network or your bad form, right? So we've kind of hit on all of these in different ways. My point would be like in the P&L bucket, the one thing we said in passing that I want to just like hammer home is when people hear P&L, they hear income statement, right? They're like revenue and cost. It's about so much more than that, right? It's about revenue versus cash, right? All of the nuance that's in the business and the full financial picture of what's going on. We talked about things like burn multiple, et cetera, but you have to have a full command for the financial health of the business. So when I say take the CFO to lunch, what I mean by that is you need to understand like truly the financial health and picture of the business. Like where is the board pressure testing the CFO? Because there are conversations that only the CEO and CFO are in, that the functional leaders are not. And that I think can really contextualize a lot of what's going on. That's probably the biggest thing that we haven't talked about yet today. But to me, those are like the four things that every leader has to prioritize and has to get right. And on number two with the first team, let's talk about what that looks like. That's the, hey, I actually had this major aha moment around AI where like I could cut 50% of my team, but no one's asking me to do it. The amazing CROs are going to the CEO and saying, I'm like putting my team up, you know what I mean? Based on what I've learned. And we don't see a ton of that yet.
Speaker 1If you're going to give executives a roadmap, where are you pointing? So I think about unit economics and some of the key metrics in there. So payback period, LTV CAC, the cost of sales. What else would you point them to, to be like, if you don't understand these things today, you got to go figure it out.
Speaker 2It's a two-part answer. For years, I had like one very simple answer for this, right? Where I said, I think Iconic in the software world has done a very good job of sort of crystallizing a framework for the metrics that matter, right? So they sort of have a set of metrics that matter, right? And I think that's a very good answer. I think they call it like the emerging growth index for companies that are less than 20 million in ARR than their enterprise five for companies that are north of 20 million in ARR. And I love those for a long time. And in the fall, in their state of software report, they actually said, hey guys, these metrics aren't changing. What's changing is how quickly and efficiently companies need to get there. Now, six months later, I don't buy that anymore, right? For all the reasons we talked about. And so now I think the challenge is no one knows with certainty what the new metrics are. And so I think that's a really good answer. And I think that's a really good answer. And I you just have to be intellectually honest enough to be challenging them. So we talked about like Kyle Poyer's piece. I'll give you another example. My friend, John Gleason, who runs a syndicate fund of customer success leaders called Success Venture Partners, who was the first CS hire at Motive, he put out this great piece that we can also link out to called Outcome Metrics 1.0 that he published maybe 10 days ago. And he took inspiration from like the SaaS Metrics 1.0 of however many years ago. And he put forward a list of metrics that he thinks are going to matter for CS more than anything else. And he talked about things. I'll give you one example. One example was something called outcome cost efficiency, right? And so the whole idea was if you pay an agent, you know, eight bucks, right, to resolve a ticket, but the human cost of doing that, do you know what I mean, was $24 of going to do it. You basically got $3 of labor value out of that investment. And his thing was to hire the OCE, the better, the stickier the company's going to be. And even if people like your product, if they don't have that high OCE, like you're kind of doomed. And that's the type of thinking that I think people have to be doing. I don't think there are perfect answers, but that's where I think the CRO and CFO can be sparring partners. I'm like, ah, like even though everyone said that was the right metric, because that didn't really pass the sniff test, you know, what we're seeing in our customer base and what makes sense for us based on the business model today. And actually one of my favorite newsletters is actually written for CFOs. It's called Mostly Metrics by C.J. Gustafson. Oh, awesome.
Speaker 1Austin is always telling me about this guy.
Speaker 2It's awesome. And C.J.'s a great guy and he like really is fluent on the business side of it. But that's like one of my favorite reads every single week is he really breaks it down. I think it's pretty brass tacks. The other one I'll mention that's not a business newsletter. It's more of an investor one, but I think it resonates is there's a newsletter from Altimeter Capital that comes out called Clouded Judgment every Friday. So good. It's so good, right? And he had a great one on like this whole question around pricing. And he gave this great example of like the GPU leasing distance and what happens when you go from per hour to consumption-based. So that's another good one for people to check out.
Speaker 1Okay. I want to move us into a quick fire to close out. The normal question is, what do you think separates a good CRO from a truly great one? But is that just your core four? Core four. Core four. So just explain Pulse on the Macro then. Let's do one click deeper. What did you mean by that?
Speaker 2So Pulse on the Macro is, I mean, I'm just going to put this very bluntly. You have to read the news. So all the stuff that we just talked about, I'm like, and it's not just reading the news for like, check, I get, you know, we always say like, congratulations, you got an A on the test, but you failed calculus. You need to read the news so that you're developing a perspective on what it means for your company. And I think that's where we're kind of missing that. Of like, oh, I'm like tracking all the stuff that's there, but you're not actually offering any perspective on like why what's changing in the world matters. And then really importantly for CROs, what does that mean you need to go and change? Because none of us have done this before, but like, what does it mean for your own playbook? And I think this is particularly important for people who are like in active interview cycles right now, where you're not going to be able to say at company X, I did blah, blah, blah, blah, blah with AI, because that's just not true. But you could say something like, man, based on what I've learned in the last six months, if I redid those four years at company X, I am super charged up about the fact that I could have done these five things completely differently. And here's my hypothesis for how it would have played out at the business. So I think it's the read the news, step one, synthesize into what that means for your customers, you, your team, and your company at large.
Speaker 1What is the most common advice you give to younger leaders, like first time VPs of sales?
Speaker 2First team thinking, always. It is always my number one thing. And I'll give you an example. I always share this example. It's sadly a real one from a couple of years ago, but I think brings this to light for people. A couple of summers ago, I was on vacation. I had this like, text me if it's urgent. This portfolio founder texts me. I'm like, is it urgent? He's like, no, actually it's not that urgent. But it's August, they're on a calendar fiscal. He was like, changing all of the quotas. So I just wanted to get your advice on how to roll that up. I'm like, it's August 30th. What, what, back the truck up. And basically what happened is that this was a business where a ton of the leads were generated by marketing or a high velocity sales cycle. And there was seasonality in the summer months. So what happened in July and August, right? The leads dried up. The reps were super pissy because they didn't have pipeline. And they're trying at this VP of sales and his solution is to go and change all the quotas. And I'm like, that is the most egregious opposite of first team thinking example. Like the question, the answer, as you know, would be like, well, what can I do to help dance the pipe from sales, right? Like, is there a spiff I can launch to kind of drive pipe between now and September 15th? What, what can I be doing? And so that is always the central piece of advice that I give new VPs of like, you, you have to play like there's a great, I'm a huge Duke basketball fan and shade daddy. I had this great lineup podcast a while ago where he's like, you got to play for the front of the jersey, not the back. That's just like, so, so well said. The one other thing I often tell them this sort of a BOGO is like, you can't build enterprise value without customer value. So like you, you just have to be like maniacally consumed with customers. And you look at the businesses that are enduring and really are set up for long-term success. It's because like that customer obsession is innate in every single function.
Speaker 1That's a good one. Yeah. The first team thinking is hard for so hard for VPs of sales, but often because of the comp plan. Like if you put 50% of their income on the line, like you are, you are driving them to think very, very clearly about one thing and one thing.
Speaker 2Here's my hot take on that. I mean, when I was the CRO at sale through my comp plan had, it was partially driven by like the commissions of the sales team, but I was also on a classic executive bonus plan. Right. And the classic executive bonus plan had every exec had three metrics that mattered. Right. And it changed from year to year, like a, you know, at what point? It was like exit error, NPS, and for like a cash target when we were profitable became deep at the target. And like, I was held accountable to those things, you know, and, and by the way, our head of product was held accountable. They sold same three metrics. You see real behavioral change in a product leader during the, when that's what's dictating the comp plan. So I think you're right, but I think it's companies miss an opportunity to like rethink how they should be doing comp for senior leaders specifically. To make sure that they're aligned to the first few metrics that matter.
Speaker 1I do think it's crazy that I know a lot of CROs that are on 50/50 plans. I think it's insane. I have very little variable in today and we've never missed a quarter in my history here. And we go at that with like the same maniacal focus that, that if I had, you know, more on the line on a month to month basis or quarter to quarter basis, but, uh, it still forces you to think about it. It, it means that you can be a much more holistic thinker. I learned this lesson at Shopify where I had no variable comp. It was just, it was just cash equity. And I thought it was insane at the time. I was like, what do you mean? Like, this is just fixed and I don't get it. But then there were like multiple decisions where I could be like, okay, like I know this is going to hurt the sales number, but it's good for a bunch of these other reasons. And I owned customer onboarding at the time, which I was had to take into consideration, but, um, it was very clarifying.
Speaker 2That's a great example, but the world just needs more Kyle's.
Speaker 1Yeah, exactly. what's the hardest lesson you've had to learn in your
Speaker 2career trust the process um and this this is advice i give people who are like very early in their career i think is you're like kind of making your way into the executive suite like you don't have all the context and you don't have all the perspective on why decisions get made and i think for me like when i was in my 20s i'm like that makes no sense like bullshit you know i mean they were doing like these things and it's and i think i can remember like the first time like i i had a bunch of friends in my company who are like let go by a riff and i like carried that for baggage for a while and then the first time i can remember i had to execute a riff i'm like oh shit we must have been terrible and so i think i that's advice i always give like younger people in their career like just trust the process like if you're working with the right people like at the end of the day if you trust the people you have to trust the process and if you don't trust the people you're in the wrong place
Speaker 1last question what's the best thing you've written the last like year or
Speaker 2so i mentioned jam and balls uh clouded judgment that is something that i quote in the office at least like five times a month like something that's going on in there and you know i like rode that ar versus err piece from two years ago i'm still talking about 25 months later right so in the last one month but i think in any given month there's something that i get like two years of mileage out of so i wouldn't say that's probably like the thing like if i think about like where i get the most sort of bang for my buck in terms of where i'm reading that probably is at the uh at the very top of the list
Speaker 1yeah all the altimeter people are so sharp like i love brad i was like i just really wish they did that podcast more like i know and
Speaker 2but it's um it's funny i um my husband is like a voracious reader he reads over a book a week and i'm like i'm a news industry junkie and so i'm like at some point it's i was like it's really that like i i do not read fiction you know i mean like it's not because i'm like if i'm reading it's about what's what's it's my pulse on macro i'm the same
Speaker 1way my wife's always telling me he's like give your brain a break like lead a read a fiction book it'd be good for you to i know around yourself
Speaker 2we had the same conversation in my household kyle so you and i are cut from a similar cloth
Speaker 1yeah yeah i read project hail mary or listened to project hail mary like a couple weeks ago
Speaker 2amazing i only
Speaker 1really want to read sci-fi if it's fiction and it was uh it was incredible so top top
Speaker 2marks you know what book i did reread actually recently you know what book i did reread actually recently and it was like a book that i was like oh my god and it's like an old one was ender's game oh just like it froze and all this because there's a book i had read like maybe it was in a college and it i was like i remember that being like an interesting read many 20 plus years ago you know now in this context so so i do think it's actually kind of cool to think about to your point you made me think of it with sci-fi with some of these books that seemed really out there a while ago and to reconsume that content now
Speaker 1yeah oh very much so well uh we will wrap it there with a minute to go uh i was excited for this one i knew i knew it would be good i was excited for this one i knew i knew it would be good i was excited for this one i knew
Speaker 2it would be good i knew it would be good yeah you and i could easily talk for hours but i'm glad we're sparing people and camping it here
Speaker 1yeah cassie thanks so much for joining and appreciate the talk thank you for listening to the revenue leadership podcast if you enjoyed it don't forget to subscribe and you can find a link in the show notes and be sure to leave a five-star review share it with your network and please join me next wednesday for another great conversation
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