Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

Brett: All right. Let's do it. Thank you for joining.

Stevie: Yeah, I'm excited to be here.

Brett: Why do you think that early revenue hires are some of the highest turnover people and roles in all of technology? It feels like a CEO goes out, they're hiring their first not necessarily GTM person but revenue leader and you follow up in six months and that person is no longer there. What's so thorny about the role?

Stevie: There are a couple of things that make those first hires very thorny. One is unrealistic expectations. The early sales pre-product market fit sales are truly coming from belief in a founder. Yes, there has to be excitement about the product, but there's a certain amount of trust and faith, and a founder tells a story in a way that builds trust and faith in where it's all headed. Often, that first sales hire is coming in or first leader is coming in and they're expected to replicate that same success. They don't have the authenticity of the origin story. They didn't build the product, so their ability to tell the story the same way just isn't there. So founders trying to pass that responsibility to somebody else is one of those original kind of thorny problems. The second is that a lot of founders don't love selling. I think that understandably it's uncomfortable, and so they bring somebody in to solve that problem for them. They're bringing people in too early to try to pass off figuring out product market fit. They're bringing them in to try to crack the nut on, "How do we sell this thing?" If you haven't figured that out as a founder, expecting somebody else who is not intimately involved in creating the product and the vision, try to solve that problem does not work. The third most common reason this is a problem is a lot of times founders are hiring for resume and they're looking at shiny logos. They're looking at somebody that's been at a big company and what they don't realize is the right profile for a first hire or a first sales leader in your company is probably not that big logo person. You need what we call a Renaissance rep, somebody that's much more creative. They're more entrepreneurial, and they're going to get out and be super curious and hustle. They're not necessarily going to have the prettiest resume.

Brett: What else can you share about that? So let's imagine a company's at five or 10 million in revenue. Maybe they have a couple of junior sellers that are supporting largely founder-led sales. What else can you say about who is ideal for that role and what would their background have been?

Stevie: Yeah, it really can vary. There's not necessarily a perfect recipe for who that person is, but what you want to look for is hunger and curiosity. Same kind of stuff you're going to look for in an entrepreneur or in a founder. You want somebody who is just deeply curious and can ask great questions. The counter-signals that you should be looking for when you're hiring somebody here are if you've got a sales interviewee or a leader interviewee who's asking you to give them some kind of confidence they're going to hit quota, that is a bad sign. You don't want somebody who's showing up looking for a guarantee of safety. You want somebody in that role who's going to swing for the fences. They may have no sales experience, but if they can ask great questions, I'm a big believer that everything really comes back to great discovery, they can probably figure out how to close deals for you. So you want somebody who's going to show up and be curious and hustle and build a business with you, not necessarily somebody who's got that shiny resume. The ideal combo is somebody that's been in a larger organization and seen what sales at scale looks like, somebody that's been early in an organization and knows what a startup looks like. If they've seen both, awesome, as long as they haven't had too much success. If you've had a salesperson who's had too much success, the chances they're going to want to start over in an early stage startup are actually really low because they've seen great success, they know what it looks like to make a lot of money in a sales org, and they don't typically have the passion and the hustle to do that first set of sales.

Brett: One of the interesting dynamics of a lot of great people in sales, people use it pejoratively, they are more coin-operated, and it's an interesting tension with what you're talking about because so much of an early-stage startup, if you go with the cliches, tend to be more mission-driven, but also most of the bestsellers actually do care about comp. Salespeople who are like, "Yeah, I don't really..." They don't perform either generally. So, how do you foot that with, again, this sort of revenues between five or 10 million, there's a little bit of repeatability type higher?

Stevie: I do think that there is a line after which you want those coin-operated sales folks, and I think that line is when you have very clear repeatable... You've got product market that you've got repeatable sales, then you just want somebody who's coin-operated, you know can give them a playbook, tell them what the ICP is and say, "Just go," and they will go repeat that at ad infinitum, and they will just make it happen and they'll hustle. Before you have that in that sort of like you've got some revenue, you've got some customers, but it's not quite repeatable yet, you want somebody thinking longer term who's going to help figure it out and they're going to do a different type of discovery. So yes, those people are somewhat coin-operated, but you want them to be a little bit more longer term incentivized. So ideally you're getting somebody in that seat, whether they are the salesperson or sales leader that is actually much more interested in equity. You want somebody who is going to be around to help build the company because you need them solving harder problems that are going to lead to repeatable success later.

Brett: So shifting gears just slightly, when you think about the role of a CRO in a business that's beginning to scale, so call it 30 to 50 million in revenue, what do you think excellence is? You take out a blank sheet of paper and it's like if this person is operating as a top 1% CRO of a business of that scale, this is sort of what they're doing.

Stevie: Yeah, it's tough because people don't necessarily mean the same thing when they say CRO. Some CROs are truly brought in as a head of sales. Others are brought in as these more generalist CROs that run all revenue. The end of the day, those top 1% CROs understand what the CEO and board are trying to achieve for the company and they are able to take that vision and those top level goals and translate it down into a go-to-market strategy that realizes those goals on a reasonable timeframe. That can mean a lot of things, and frankly, the role changes every few months because while those top level goals stay the same, market conditions change, the team changes, the competitive landscape changes. So you have to be able to distill those big visions and those big goals into something a team can actually operationalize, and that is really the job of a CRO and that could be everything from sales tactics and playbooks to a change to the ICP to a change to how we go to market to a systems design change. It is different every few months, but you have to be that translation layer between top level vision and goals and the real world, how we're making it happen.

Brett: What have you learned about metrics in the context of go-to-market and what are the parts that are very important but actually hard to get a precise metric, and then where are metrics so blatantly obvious that you should be running the business on?

Stevie: Yeah. I mean, everybody knows the top level metrics, right? Top-line growth, retention. There's this key set of eight to 10 metrics that everybody pays attention to and operates their business on. There is this next level of metrics under that that I think people pay attention to are important related to conversion and efficiency, and there's a whole set of metrics that matter there. The stuff that most people don't measure that I think actually very important are things like confidence, things like velocity. We often have a tendency in go-to-market to measure these point measure things. We measure time to close, for example, as a measure of speed, but there are other considerations that go into the velocity of the organization. I think you have to compound some of these different observations and metrics into a better sense of how much confidence does your team have in what they're doing. When they get on a call, are they opening that Zoom with confidence they can tell the story successfully and that they can win? When they do that, are they equipped with everything they need to generate the right amount of velocity to execute on the opportunity? Those aren't necessarily individual numbers. Those are a lot of things that you got to pull together to get a sense of how real that confidence is, how real the velocity is, but those are really the things that matter in go-to-market.

Brett: What is velocity in that context?

Stevie: In this case, velocity is going to be a measure of speed in some form. In simplistic terms, it's how long does it take to close a deal? How long does it take you to action a lead? It is also though how quickly can your team act on an opportunity once they see it. They have a great conversation with prospect. How quickly can they actually then close a deal there and get that customer not just signed but successful? So it's going to be the breakdown of how quickly can you get a contract out the door. Once you do that, how quickly can the prospect act on it? Once they sign, how quickly are you getting them into your product and getting them successful with your product and onboarded? So there's this whole customer experience that you've got to measure and there are point in time measures of speed within that, but it's more about reduction of friction than it is just going fast. You want to be able to reflect the urgency of your customer, of your prospect, not rush them, but execute on their timeline in a way that feels very natural and easy.

Brett: On the first point that you made about basically rep confidence, is that something that's a judgment call for you, or how do you know if there's sufficient or insufficient confidence at the rep level?

Stevie: It is more a judgment call to math. There's definitely math that matters here. Win rate is the most obvious place this shows up. Obviously, confidence is not the only factor there. It is a little bit of vibes and I do think it matters. I think that in the early days the way this shows up is when you bring in these early sales hires as a founder. There is this robotic thing that a lot of early sales hires do where they are articulating the story. They are saying the words, but they don't yet understand it. They don't yet believe it, and you can feel it, but you can't measure it. It'll show up in all your efficiency metrics, but it's hard to pin down that cause. The best way to get to the heart of that confidence and if it's there and the way you want it to be is just listening to live calls. I know early stage this can be uncomfortable. Recording calls and listening to those calls is really the only way to get to the heart of this and to coach people to confidence and get them to a place where they have that authenticity, they have that sense of belief in what they're selling because if they bring that, it's hard to lose.

Brett: What are your thoughts on the CRO role when most the customer experience or customer journey is housed underneath that role versus not and the trade-offs between those two?

Stevie: I think you just need to know what you're getting into. I think both models are valid. CRO as head of sales is a valid thing, but you need to be clear, and I don't think most CEOs or founders who go out to hire are clear about if they're hiring a head of sales or if they're truly hiring a CRO. I do think that that is one of the biggest misunderstandings of my current role is that I don't consider myself a sales leader. I hire sales leaders. In fact, that is a core part of my job is hiring great sales leaders. Leading sales is fundamentally not my job. My job is to achieve the top-line goals and sales is a contributor to that. So, you really need to understand deeply before you go out to hire somebody in a role like this, are you truly hiring this jack of all trades CRO who's going to help you achieve the top-line goals? And if so, that should guide the kind of profile that you're looking for. It is not just a VP sales plus plus, it is a different skill set. It is more analytical. It is more systems driven, and you need somebody who's going to be more strategic. You can't just take a VP sales and promote them into that role.

Brett: What's the reason why a founder and CEO would not want that shape of hire?

Stevie: I think that it is something that can be done much too early. You'll see this often when founders go out to hire somebody in this role and they start without a title or they start with a VP of sales hire and then they'll go out, they'll talk to candidates, they'll get really excited about somebody who they think is good and then that candidate will say, "This is great. I'm excited about your company, but I'm looking for a CRO title." A lot of candidates who haven't had the role yet are thinking about it as just a promotion. It is VP sales, but the next step. As a founder, I think you really want to peel apart their understanding of what they're asking for and does it align with the problems you are currently seeking to solve? So before you hire a CRO, I would not hire a CRO before you have great sales leadership, for example. So if you hire a CRO and then you say, "Okay. Now just go lead sales," you're going to have a mismatch in expectations. You could potentially have a mismatch in profile of who you've hired. You want to get super tight. It's much better to bring somebody in as a VP of sales and give them a path to becoming CRO over time as opposed to hiring them into that title just because they seem super great as a sales leader and they asked for the title. It just leads to mismatches and it ultimately sets everybody up for failure.

Brett: Were you someone that knew that eventually you want to be a CRO or were you trying on different things and here we are all these years later?

Stevie: I did not. 10 years ago, I did not know what a CRO was. My career has been very non-traditional. I happened into sales. It's not a career I ever thought that I would take on in the first place. That happened about 18 years ago, thanks to an incredible mentor who found me in a product role and said, "I need a junior salesperson. Think I can take you and teach you to sell?" That for me was a real inflection point. I thought, "I'll do it because it sounds uncomfortable," and I ended... I was terrible at it at first, but he was amazing and he modeled what great looked like. Back then, we were selling on the road. I was going meeting to meeting with him, so I saw he was great.

Brett: What did you see?

Stevie: I saw him sell the vision. I saw a very entrepreneurial seller and I saw him practice that over and over. One of the key lessons he taught me in that timeframe was... Because I was very shy. I was not a natural salesperson at all. I saw him be vulnerable in these human interactions and the point he made to me was, "You are going to have to push people harder than they're comfortable with. You're going to have to challenge people, ask for things they don't want to give you. The best way you can make other people comfortable is to be vulnerable and then you give them permission to be human. So if the meeting is tense and it's not going well, be vulnerable, poke fun at yourself, make yourself more accessible and then the other person will become more accessible." That lesson has stuck with me and it was like a big unlock for me in sales. I got a version of that later when I was in sales but still didn't know if CRO was an option or something I wanted to do. I was at Twilio for six years, had an incredible mentor there, George Hu, he was our COO. He had been the number two guy at Salesforce for a long time. George modeled for me what a CRO or a COO does. He taught me over the course of years that playbook.

Brett: Which is similar to what you were talking about in terms of how do you translate a goal to a strategy.

Stevie: Yes, he showed me how to build an operating model, what does it look like to hyperscale an organization when you've got product market fit and you've got this incredible opportunity. He showed me the math and analytical side of the business and how to build that strategy. I think the takeaway both from my time with Matt Golden and my time with George is the single most important thing you can do if you want to be a CRO, you want to grow in a revenue organization is be a part of a great organization when there's somebody you can learn from. I think the mistake a lot of people early in career make is, "I want to maximize my title. I want to prove I can be a VP sales," so they go to be a big fish in a little pond. Can't learn anything like that. Learning in an organization where you can grow under somebody great who can teach you how it's been done is the single best way to advance and really challenge yourself.

Brett: If a lot of the way that you have grown is through being around some extraordinary people, what about the opposite of that? What's the only stuff that you learned that you can't just do it by watching somebody that you just have to be in the seat and figure it out?

Stevie: There's a lot. I think that what has been shocking for me in a lot of ways with the CRO role is there is no playbook. I think because every business is so different. You get in a seat in a job like this and you will get lots of advice from lots of well-meaning people. You will get guidance from the board, the CEO, people outside the company and telling you where to focus or what to do, and the single thing I have learned is that every business is incredibly unique and you cannot apply somebody else's advice or playbook to your business in a meaningful way. It's really important to understand how everybody else is doing things and why. Ultimately, you need to divine the truth of your own business for yourself, trust your data and your instincts and then execute on that, because if you try to run somebody else's playbook in this job, it will always be not quite as good because you're replicating something that works somewhere else in a different business. So, there is some instinct. There's some gut feel. One of the big things that George had told me about being in a role like this, said, "The hardest thing when you get up every day is you could do anything and there's nobody to tell you what to do." So you have to develop a certain level of instinct and it does take time. I think that's why a lot of CROs don't make it that first 18 months because either they're not empowered to have that time to figure it out or they don't trust their instincts, so they try to run somebody else's playbook.

Brett: Explain this a little bit more in the sense of in the context of Vanta, it's not as if you are coming in knowing nothing about sales and customer success and on and on and you are going to start everything from a blank sheet of paper, but to your point, the inverse is also not true. You had an incredible career at Twilio. You're not taking that and just slamming it into Vanta. What does it actually look like to find what the path is when you bring those two things together, or what's an example of, "This is how we approached exit at Twilio because of Y and we had to approach it this way because of that," at Vanta?

Stevie: The underlying key with all these things is you need great data to understand your business... Okay. I'll give you an example from Vanta. I made a early mistake thinking I could take a playbook from Twilio and apply it here. I arrived at Vanta, incredible product market fit, tons of inbound interest, more interest than we could serve. One call closes, lots of excitement. The guidance I got from everyone was just hire, hire salespeople, and that resonated with me because that was the playbook at Twilio. We had all this great product market fit. It was like, "Okay. Go hire a bunch of salespeople to serve the demand. Scale that up." Well, I did that and what I learned about six to eight months later was that, well, maybe hiring might have been a solution. I hired the wrong kind of people and that was fundamentally because I did not have my data infrastructure appropriately set up. I didn't understand what kind of demand we had, so I assumed that all of our demand looked the same. It was all founders who wanted to do SOC2 compliance, like very simple entry-level stuff. Turned out it was much more complex than that. There was mid-market opportunity in there. There were more complex SMB use cases, so I hired a bunch of junior sellers thinking I could just throw them at the demand and up until the right we go and that is not what happened. Ultimately, that was a really painful lesson. The biggest takeaway for me was we did end up running that playbook later and hiring more salespeople to serve the demand, but we needed a very different kind of salesperson, a different kind of an enablement and an entirely different playbook. So the top-level assumption was not wrong, but all the details were wrong and that ultimately led to a lot of pain.

Brett: Maybe building on this, if I were to look at the way that you've assembled the whole customer experience from pre-sales to post-sales at your revenue scale today, and I took five other great businesses who are at the same revenue scale, what are the points that are most different? What are the things that you're doing in the most unique way that flows from the strategy of the business and how did you land on that?

Stevie: I would say one of the things that makes us incredibly unique is that Vanta remains 100% sales-led. That is unbelievably rare at our scale, especially for a business that is not a fully enterprise business. We do sell in the enterprise now, but we serve everyone from founders to CISOs of the Fortune 100 and we do that 100% through salespeople. Part of that has to do with the type of business we are and part of it has to do with the metrics. So we are a business that is very focused on trust, and therefore, humans talking to humans is how people generally want to buy our product because they want to know they can trust us. So trust being so fundamental makes us a little less of a PLG-friendly business. It's put humans at the center.

Brett: If someone were to watch how you spend your time in a given week, what's interesting about it?

Stevie: I think that the thing they might be surprised by is the diversity of types of problems I'm having to solve on a regular basis. I do think that part of the beauty of Vanta and part of why I love it is that our founder, Christina, is she's very in the detail. She is able to conceptualize the entire business in her head at any given time and that kind of leadership really attracts me because I like to be in the details as well. The diversity of types of problems we're solving on any given week is pretty intense. In some cases, I've got teams that operating relatively well without really any involvement from me, and in other cases, I'm extremely involved in the minutia of these teams work and defining what comes next. So I think that's one. I think the second that would surprise people is how far ahead I'm thinking. When I talk to my team, the vast majority of the time, I'm not even just talking about this year, I might be talking about this month or this quarter. On a daily basis, I'm thinking 24 to 36 months ahead, and most of my choices are predicated on what we are trying to achieve over the coming two to three years, not in the current period because everything you do in go-to-market has a long runway. One of the most common ways people go wrong in go-to-market is they think they're going to deploy a strategy immediately see if it works or not, and then-

Brett: You're talking like time-to-value.

Stevie: Yeah, it's time-to-value, but it's also just like time to get effective with something. You might deploy a team to sell a new product. Depending on the product, you could see six months where it might look like it's failing and then in month seven something starts to catch and that team learns because the heart of it, when you're trying to do something new, people have to learn a lot, so you want to give things sufficient runway so you can let them play out. That groundwork laying, I'm already thinking about next year I know what my two next big revenue drivers will be beyond the core product. In 12 months, those products probably aren't going to drive a lot of revenue. I'm building the teams now, so they will start to learn, they will build some muscle, they'll build some learnings and expertise so that base is there when we're ready to scale that I can build on top of. So it takes time. You can't just die with a team.

Brett: Why is that?

Stevie: Yes, because people are ultimately... Humans take time to learn and anytime you're doing something new, you got to see people... Especially if you're selling in the enterprise or something more complex, the typical ramp, even if you know the playbook, typical ramp for an enterprise seller can be six to 12 months. So, that's if you have it figured out. If you're putting them in a situation where it's a new product or it's not figured out yet, that ramp could be even longer than a year. So you have to seat people and let them figure it out for a period of time before you can expect something to take off, and if you don't, you're going to get early signal that you really cannot trust because there's so much human fallibility and learning tied up in the whole thing.

Brett: This blends over with a little bit about what we're talking about, but what do you think are the decisions that you singularly are responsible for and maybe what are some of the decisions that people might think you and your CRO role should make but you push down or give to someone else to make?

Stevie: I would say it's rare that I make decisions myself at this point. 98% of the decisions that are happening in my organization are either getting pushed to my leaders or they are a consensus in the C-suite among my first team about direction. The decisions that I make generally speaking are going to be... For example, if we're going to set a growth target for next year that we want to grow X percent year over year, I have to be the one to lock eyes with my first team with the C-suite and say, "Yes, I accept that target. I'm going to go make it happen." It doesn't really matter what anybody else's opinion on that is because ultimately I'm the one that's going to sign up for it and say, "Yes, my team is responsible for that. Let's go execute on it." Beyond that agreement, pretty much everything else gets pushed to somebody.

Brett: Why have you chosen to run the org that way?

Stevie: I think that decisions are best made by the people closest to the information and their unique insights guide us to better outcomes. At this point, with a 600-person organization, I am going to be more distant from the vast majority of the decisions that need to get made, and I believe I have hired extremely well. I have a very smart team and I trust them. I find that when you hire great people and you empower them, it doesn't mean that I'm expecting them to make the right decision or the perfect decision every time, but I owe them the opportunity to make those choices because that's the only way they're going to learn and grow. If they learn and grow faster, they will become better leaders more quickly.

Brett: How often do you disagree with the decision that a given leadership team member is making?

Stevie: 20 to 30% of the time.

Brett: Of those, let's say three out of 10, how often are you right and how often are they right?

Stevie: That's a great question. I'd say it's half and half.

Brett: In the situations where you are incorrect, is it normally that they understand something about the business from their vantage point that you don't?

Stevie: Yes, it's that they've got some unique insight. They are closer to it. They've seen it. They've got gut feel for what's going on in their part of the business, and those unique insights lead them to better decisions.

Brett: Have you found that your own intuition is generally off in a certain subset of areas? A lot of people say the best advice is trust your gut, trust your intuition, which I think is probably generally right. Is there a category of things like when you reflect on judgment calls that are very noisy for whatever reason?

Stevie: Yes, and I would say that those categories have shifted, but I think the area that was hardest for me was coming in as somebody with primarily a sales background. I think I came into this role believing I understand what motivates people, and I have found that I was wrong about that on a lot of occasions. My natural inclination is to motivate people and talk to my team in a way that motivates salespeople. It does not resonate with a broader base of people who might be serving customers, whether that's customer success or support or... I think that there's a bigger story and a broader set of things that motivate people in other roles and that's where I found my instincts were not nearly as good. So it's something I've had to intentionally develop and get much more thoughtful about.

Brett: Sort of on this set of themes around decision-making, what are the decisions that you still wrestle with and find very, very difficult to make or to figure out what the correct thing to do is?

Stevie: I think the hardest set of decisions at this point in time has to do with how many humans to add to the team. In a world where there are clearly AI solutions, technology solutions that on paper can do the jobs that humans are doing and there are... We don't have a lot of artificial limitations in our business. We got great gross margin. We are great from a cash position. So it's less about can we do it? But I know that the world is changing very quickly and I feel an intense responsibility when I bring humans into our business to set them up for success, and I want to bring them into roles that I can confidently tell them are going to continue to add value in our organization over the long term. So, wrestling with that idea of do we solve problems system first or human first or some combination thereof and can we really tell people with high trust that we're bringing them into a role that's going to continue to exist? Those are the hardest questions at this point. I don't think anybody has a clear answer to those things, so it really requires a lot of introspection and just thoughtfulness because it's cliché, but these are real human beings coming in to trust you with their career and their life and the weight of that is not lost on me.

Brett: What's an example of a role you were wrestling with and decided that people should be really doing this?

Stevie: SDR is a great example of this. I am so bullish on all the AI tooling. AI will continue to transform the way we go to market, but I have deeply come to believe that jobs like SDR for the foreseeable future should still be human first. The beauty of AI tooling is not to replace those humans, it is to elevate their work to allow them to do the higher value work, to be more thoughtful. There are solutions that will absolutely do big parts of the job that they do today. I believe the SDRs will continue to have tremendous value in our organization. So we've made a big bet on humans there. It's a little bit of a contrarian bet, but I'm finding it pays off because the thing that cuts through all of the AI-generated noise today is real humanity. So, human SDR is picking up a phone and having a meaningful conversation with someone actually cuts through when AI-generated email does not.

Brett: Switching gears just a little bit. When you think about your leadership team, the folks that report to you, what are the threads or attributes that regardless of if it's a customer success function or sales function are your non-negotiables maybe in the least generic sense, so not like honesty and those type of things, but the differential bits that are important for your specific team that you're building?

Stevie: There's a couple of things that for me are key with these leaders. One is just intense curiosity and it comes back to sales skills, customer skills. Without curiosity, we are getting nowhere. We have to change the business every few months, so I need people who have that growth mindset and the curiosity to drive it.

Brett: Do you think that is abundant or not abundant?

Stevie: It is not abundant. I think that there are a lot of people who come in with high confidence that they already know the right way to do things and they are not open to new ways. The curiosity has to be tied to a certain level of humility, which I do think is a bit contrarian. I think that a lot of folks in the Valley hire for confidence and ego. I'm hiring confident people and I'm hiring incredibly competitive people, but they are also people with very little ego. What defines the team I'm trying to build is a team that is intensely competitive with the outside world and inside the walls of Vanta is the most collaborative team that you could build. So it is people who absolutely live to get up and crush the competition, but then want to help their teammate hit quota or close the deal or win or whatever it is. So there's this balance of kind competition that I find differentiates who we are as a team and who my leaders are, and looking for a curiosity and growth mindset. When I interview and I find you can see when you ask these questions, I always love to ask people, "What is something that took you a very long time to accomplish in your life? Tell me about that journey and why'd you do it? What motivated you?" It does not have to be work-related. I'm looking for somebody that's passionate about achieving things, and as they tell that story, you can hear the humility. You can hear the hunger. We have a joke inside Vanta. At one point, somebody wrote a piece about Vanta and one of the subtitles on the article was Midwest Assassins, the Midwestern Assassins. We've got this Midwestern vibe of people who feel like they're outsiders to a certain extent and have this work ethic and have this hunger. When people tell you the story of something they had to really work hard to achieve, you either hear somebody who is ultra-confident and tells you how everything went right or somebody that can own the things they did wrong. In that slight part of how they tell their story, that's where you can find those people that are very hungry but can see their own failings and have the curiosity to continue to learn.

Brett: When you assemble all the more senior people that you've hired that you've had to let go, they did not work out, are there buckets of reasons of the things you got wrong?

Stevie: Yes, I learned a brutal lesson on this front and to the person. My hiring mistakes have been tied to the idea that I was hiring someone that knew something I didn't. So I made a few key hires where I was hiring someone because they came from a cybersecurity background or because they had 20-plus years running the function I was putting them on. In each of those cases, I was attributing to that candidate some magical knowledge that they were going to bring and they were going to figure everything out for me and they were going to solve all of my problems and it was always wrong. It was always wrong because what they did is exactly what you should not do. They brought a playbook and they tried to apply their known playbook to our very unique business and it didn't work. I didn't take into account how they would do with the unique people on my team. I didn't take into account how they fit into the culture. I just thought, "This person knows something I don't." I was wrong every time. Those people never worked out. The people who do work out are the ones that have that grit. It's like a personality type and it's not about some unique knowledge. They need to know basics, but when you're looking for some unique knowledge, it's just you're bound to go wrong because knowledge fades. Anybody can learn anything.

Brett: But haven't you found people with unique knowledge that also possessed what you're talking about in terms of curiosity, open-mindedness, et cetera, et cetera, and were successful or not really?

Stevie: Not really.

Brett: Why is that? You can have somebody that worked in cybersecurity and is curious and is not going to apply some generic playbook.

Stevie: I think it's because we are trying to do something different. We have built a product and a company that are trying to disrupt existing industry. So by and large, people that are going to come from that industry, they have a way of looking at the world. They have a way of thinking about things. There are people that have brought some subject matter expertise, but when they do that never ends up being the thing they bring that really has value.

Brett: But so then what's the role of experience? Why aren't all your direct reports three years of experience as a chef? Push it to the extreme. I assume if I were to look at your directs, there are people that have done variations of the thing that they're doing, so there is an experience component.

Stevie: There are in some cases. I will say my head of sales, Elliot Goldwater, he is amazing, comes from channel background, never ran direct sales in his life. He is running my entire global sales organization. He's one of the best sales leaders I've ever worked with. So, I do think I have found more success with people that don't necessarily have the experience. That said, it does play a role and I think the biggest role it plays... Kelly Bray is a great example of this running post-sales. She's got several years of experience running these post-sales teams and there she's gotten those at bat. So she's seen what worked and didn't work. She could learn from it, but she has seen enough different circumstances and she's open-minded enough that she didn't show up saying, "I have the answer and I'm going to roll that out on day two." Yeah. She showed up and she listened and she learned and there was that humility to be open to trying it in a new way.

Brett: How do you think about centralization versus decentralization in your 600-person org or where you want process and systems versus where you want it to be decentralized judgment at the edge of the org, sort of let people use their best judgment.

Stevie: I aspire to centralize the things where we've got localized product, market fit and repeatable playbooks. So my global sales org, I really don't want that decentralization. I want everybody singing from the same songbook. I want us telling the story of customer value the same way. For me, their centralization is key. That's where you get efficiency. That's where you get this consistency of experience. But there are lots of parts of the business where that's not the reality, whether that's places we're shipping new products, new geographies, a new segment we're entering. In all of those places, I aspire to almost the opposite on day one. I want them to have as much latitude and as much leeway to figure it out as possible. One of the hardest things in a big company is that if you've got this engine that's successful in a product with product market fit, it just has all this inertia and momentum, it becomes very hard to do something else. So what I've found is you have to separate those teams that are doing something new and give them the space to operate without getting sucked into the successful engine that is doing the thing you already know how to do.

Brett: What's a good example from the last year?

Stevie: So for us, the biggest one of these has been our move into serving enterprise customers because Vanta, historically when we started out selling 100% to founders automated compliance, first-time compliance use case and very short sales cycle. It was 100% inbound for a long time. So there is this engine of success and we are unbelievably good at that. When we first started trying to move up market, we had opportunity, we had pipeline, but what we did was just give those leads to our existing team and we just radically failed at it because they were so distracted by the thing that was easy that they knew how to do. So then step two was we created a separate team and said, "Okay. You're our mid-market team. You're going to start selling to a different set of customers." But we kept them as a part of the core sales team and still we found they were just so distracted by this transactional business that even though we were telling them, "You now are measured on a quarter, not a month and you have to operate differently," they just couldn't look away from the core of what was working. It wasn't until we hired a completely separate leadership team, we sectioned off our enterprise organization and we basically said, "You guys are completely separate and you're going to sit over here for a year." We actually ended up having them roll up to a GM who was in our engineering and product development team for a year. So we sat them closer to the product. We separated them from the core revenue engine of the business. It wasn't until we did that that we started to see them build momentum and success. They just had to get enough separation from the core.

Brett: When you think back to your own career up into the role of CRO, what were the few moments or actual conversations that have stuck with you that were formative in some way? You talked at the beginning one was when you were watching what it means to sell.

Stevie: That was definitely the first. I remember I stumbled through my first few years of sales and I was starting to figure out some of the mechanics. There was a point in time at which I got a sales leadership job at a startup that ended up getting acquired by Visa. In this, it's in payments and financial services. So at this time, I was in my mid-30s. I ended up having a team of sellers is a very deeply entrenched industry, team of sellers that were 15 to 20 years older than me. I remember talking with them early on and I could tell there that I was going to have to earn their trust. Over time I got in deep with them. I showed them how I could do discovery. I built credibility and I remember one of those very tenured sellers, a guy that had been selling for 30-plus years saying, "Man, I was skeptical at first, but you really know how to twist the knife." That stuck with me and in a way it was a nice compliment, but it also reassures-

Brett: Why is twisting the knife a compliment?

Stevie: It was just what he was trying to get to because I did inspect this with him. Think what he was really getting to was that ability to do deep discovery and to get to the heart of a problem or to the heart of what matters to a customer, and that for me was this eye-opening like, "Oh, that really does matter." To have somebody so much more tenured see that and encourage it, it made me just double-down on that skill in a meaningful way. Then along the way, I used that to start to get to know different types of people in a way I hadn't been able to before. I think the next big turning point for me was at Twilio where I got this opportunity to see people operate at a scale that I had never seen before. In that, George, our COO, it was funny because he never directly told me or taught me things. He would give me these haikus little riddles to go figure out and that alone his teaching approach.

Brett: What was a riddle?

Stevie: He would give me these fragments of sentences of like, "Go figure out this thing over here." At one point he told me, "There's this incredibly important meeting that happens once a month at this company, go find it and get into that meeting. That's where all the decisions get made." I later found out that I was a lowly senior director, this was like an SVP-plus, C-level meeting. It took me several months. I ended up being owed a favor by the CFO and he said, "What can I do to make it up to you?" I said, "You know what, you can invite me to this one meeting." I got myself into that meeting and it was... I learned so much in that meeting. It was a meeting where the leaders of the company and our finance team, StratFin team, talked about all of the core metrics of the business and it's where they were talking about what the strategy should be, so all the data, all the gnarly problems and what are we going to do about it? So just to hear the way they talked about the business, that exposure changed everything for me because then it was like this light bulb. It's like, "Oh, now I understand how they think about problems and how they think about what to do about them." Then I started trying to figure out how do I do that and just that one meeting was enough to unlock it.

Brett: When you think about the overall end-to-end customer journey, what part has the greatest hit in leverage, the thing that's when you invest in it, you get crazy returns and maybe most people don't?

Stevie: It is the first 30 days, and I think this is true for a lot of businesses, it is incredibly true in ours. There is this natural inclination, especially as a sales leader, to be so focused on the signature and then you're like, "Great. We've got a one-year term. We've got a whole year to make this customer successful." One of the big eye-opening moments in our business was we set out expectations. "It's a year term and over the course of the year, we are going to make you successful in accomplishing the mission." When we compressed that and said, "We are going to spend an intensive two weeks with you and we are going to get you successful in just a few days," it's like the customers all of a sudden were like, "Oh, great, that's the schedule. We're going to do that with you." When they see early value, you just build tremendous credibility and the chances that they are going to churn if you can make them successful early are just radically lower. So that first 30 days is to me the magic moment where if you can win them there, build trust and credibility, you've got them for good.

Brett: What does a perfect first sales call sound like?

Stevie: Perfect. First sales call is going to be about 60% discovery. Most salespeople that get that it's a first call and they desperately want to show the product or they want to get further, but you want to do majority discovery because the only way to run a sales cycle is to deeply understand the customer's pain and you can't do that without intense discovery. You also want to provide value because regardless of your solution, if they're going to buy or not, the thing that will guarantee a customer will spend more time with you is if you deliver some kind of value to them, and that value might be subject matter expertise. It might be access to something. Ultimately, you want them to view you as somebody who brings value. So if you can deliver 60 to 70% discovery and then spend that last 30 to 40% of the time, giving them something of value based on what you learned in discovery, you are nearly guaranteed that it gets a second call and that's got to be your goal.

Brett: So, you don't do a traditional demo and that type of thing on that first call?

Stevie: We really try to resist that. It is very tempting, especially in a space that is competitively noisy to go to that demo, and I think that that is the easy crutch because we have a great product. It's tempting to say, "Well, let me just show you." The reality if you're just going to show a customer a product is you don't understand what their pain is. Why are they even talking to you? Without that why and without implicating the pain, as we call it in sales, you don't even know what part of the product to show them. If you're going to give them we call it when you give a general demo, the harbor tour, and the harbor tour is generally a waste of everyone's time. It feels comforting. She's like, "Look, I have this beautiful product." But the reality may be there may be just one piece that is the magic piece that they care about that solves their problem and you could spend 30 seconds showing that and get more impact than the harbor tour the last 30 minutes.

Brett: How do you know if the problem with the broader company as a product problem or a go-to-market problem?

Stevie: I think that in the vast majority of cases, problems are a little bit of everybody's problem. It's rare that it's on just one side or the other. I think that you've got to get enough at bats at discovery to really peel that apart. We, of course, use Gong to record our calls. One way we get to the heart of that is if we start to pick up on a theme, we'll develop a hypothesis about is this a product problem potentially, or even if it might be a product problem, is there a way for us to work around that? So, we will test ways to address it. We'll see how that lands. Ultimately, if we find there is a real gap here we need to address, then we'll pass it over, but generally, we're trying to address things first without saying like, "Oh, this is a product problem. Let's go fix that."

Brett: Is it just how you're wired? Because I feel like in many companies you have go-to-market leadership blaming product leadership and product leadership blaming go-to-market leadership.

Stevie: That is very common. Yeah, I do think it is partly how I'm wired. I also am acutely aware of how toxic that dynamic can be and I don't think you end up achieving anybody's goals that way. One of the big inflection points for me and how to think about go-to-market was at Twilio, we had a specific QBR. This is not with product, but it was one of those typical dynamics where I came into the QBR and I had all these beautiful charts and graphs to basically show marketing is not giving us enough leads. I proved that out in triplicate, and George looked at me and said, "Okay. So, what can you do about it? What do you have control over? I don't care that marketing is not delivering. You can do something." I said, "Okay. We can outbound. Let's go." It was a great example of taking control and having that agency to control your own destiny. I would love to think that every product gap we uncover will get immediately addressed, that would be amazing, but in reality, you will get a better outcome if you as a team think about that question of what do we have control over? Is there something we could do differently to work around this issue and ensure we're going to give the feedback? We want to iterate on the product and we want to make sure our feedback is high quality, but in the meantime we're going to control the controllables and do what we can do.

Brett: What do you think is the difference between a top 1% CRO in 2026 and a top 1% CRO in 2028, if there is anything?

Stevie: I think there will be a huge difference. I think in 2028, everyone will need to be systems first instead of human capacity first. That's not to say we will not have large go-to-market teams, but I think in 2028 you're going to have to have CROs that know both sides of that equation. There's an interesting thing happening right now, and I think this is what's going to manifest in 2026, is you've got all these AI-native companies. They're growing up almost like prosumer PLG. They've got all this incredible off-the-charts growth, but what happens for the vast majority of them is they hit this point where they see an enterprise opportunity and it's very hard to capture the real enterprise opportunity without a classic go-to-market engine. Enterprise buyers are decades probably from self-service PLG acquisition of technology. They'll get there eventually. But if you even look back at how long it took enterprises to move to the cloud, there's still plenty of enterprise workloads not in the cloud, which seems completely insane, but they are slow to adopt because there's a huge amount of revenue at risk. They've got these massive multi-billion dollar established businesses. The level of risk in buying new technology is high. They expect to be sold to by humans and I do not think that will change by 2028, probably not even 2030. So you are going to have to have CROs who both understand a systems first AI-native way of going to market and know the enterprise sale and can build a real sales team to complement. Those things cannot be separate. They won't be exclusive of each other. If you can build a system and a human team that are really tightly intertwined and feeding off each other, that's what a top 1% CRO is going to be doing in 2028.

Brett: What percentage of CROs do you think are capable of making that transition?

Stevie: Less than 10%.

Brett: So, where do you think that next generation of CROs is going to come from?

Stevie: I think they are not going to be former salespeople. I think that they are going to be a different breed. I think they're going to be more technical. I think you're going to see people who potentially have a growth background, people who have enough exposure to sales, but also are technical and get systems. So it's like growth, rev ops, GTM engineering. That is the background that I think will grow into a CRO role and it will not be somebody who came up through 10-plus years of selling.

Brett: When you talk about the systems design, make that a little bit more tangible.

Stevie: Yeah. I mean, the system itself, there's a change we're going through now on this that historically go-to-market systems are very siloed, right? You buy 20 different pieces of SaaS and they all sort of integrate lightly. You've got your data in CRM. It is a very siloed world today. That will not work going forward. One way that I'm addressing this right now is I've actually instead of historically would have go-to-market systems live inside of DevOps, I think systems now is a top-level consideration. I actually just hired a systems architect reporting directly to me who lives outside of DevOps and owns go-to-market systems architecture.

Brett: Who their background is a DevOps background-

Stevie: No, he's background is-

Brett: ... or just an engineer?

Stevie: He's got an engineering background, but he has done GTM systems so he's got some familiarity, but he's ultimately an engineer and that design is going to be central to how we move forward. He today is a unicorn. There aren't a lot of people out there like him, but I think that that is going to be one of the most important roles in the org going forward.

Brett: Why do you think it's going to happen so quickly?

Stevie: I think it's going to happen quickly because if you look at the revenue growth from these AI-native companies, it's just a totally different universe. It used to be if you got to $100 million in less than five years, that was legendary, just unbelievably rare. Now you just see AI-native companies hitting 100 million in ARR in two years or less. So I think that everyone sees the opportunity. So there's this forcing function. Everybody wants to win and it's very clear that there's a way to win that's different and that way to win is systems forward, but it can't be exclusively systems. You've got to find that unique blend. I think right now we've got this crop of AI-native companies that are doing the systems forward thing and they are now hitting that, "Oh, wow, okay, we've got to actually figure out go-to-market. How do we even do enterprise sales?" That's a whole other thing they're not familiar with. Then you've got legacy SaaS companies that are watching that and realizing they have to do something differently that looks more like PLG or looks more like a systems-forward approach. So you're going to have to get that blend from both sides to get that next wave of what really is going to win.

Brett: Maybe this is obvious, but what does that mean for people who want to thrive in the next five years and do want to be a CRO and maybe did come up under sales? Is there ways they should be positioning themselves?

Stevie: Yes, and I think it starts with educating themselves. I think that you cannot just sit and watch this stuff happen or read about it. You have to participate. We're at the point you have to download Cursor, start coding something. You have to actually personally experience it. What I see a lot of senior leaders doing is watching it and speaking to it, but not participating. I think if you don't get your hands dirty and try it yourself, you're never going to really get it. If you want to come up through that traditional path, but you want to make this move, getting your hands dirty and actually building has to be the way. It's not an option to not be a builder.

Brett: When you think about being effective in running your function, how do you think about balancing, how demanding to be and hard-charging to be with helping or supporting or whatever other term you would use?

Stevie: You can push a lot harder and be more demanding than it probably seems. I default to pushing very hard and setting unrealistic goals and swinging really big because I consider one of my core responsibilities painting the picture of what's possible, and if I'm tempering expectations or saying like, "Oh, it's okay. We didn't quite hit," that becomes the culture. So I do think it is my job to set the bar for urgency and results unrealistically high. At the same time, I do recognize that there are humans working for me and I want them to be happy in their work. I want them to feel rewarded. I want them to feel seen. So for me, it's not necessarily a balance of supporting and helping versus setting the bar high. I think people get a tremendous amount of joy and enjoyment out of achieving hard things, so I will always push very hard. I think the thing I'm forever trying to balance with is seeing the people who work for me as humans and saying that out loud and making it sure that they understand how much I appreciate them. If you can find people who thrive in that sort of type two fun, really hard achievement environment and then back that up with real human connection, that's the win.

Brett: What about partially the inverse of this? What do you think a lot of people think it is to be an excellent CRO or to be a great C-suite exec that you think is misunderstood or wrong?

Stevie: I think that the expectation is people do think that you have to be kind of a jerk. I think that they think that you have to be aloof or perfectly buttoned up and maybe this is just bias that is very much not me. I actually think you're much more successful when you are real and you are vulnerable and you are honest. That's the way to build a real team and build loyalty is just be a real person and admit the things that you don't know the reality. I know a lot of CROs and to the person, none of us know the whole job. None of us know all the answers. Even if you've had the CRO job before, every one of these is so different. We all have blind spots. The more you actually own that, the more likely you are to be successful.

Brett: What can you share about the specific relationship or your perspective on the relationship between a CRO and a founder and CEO specifically?

Stevie: It is the most important relationship. Speaking from experience working with Christina at Vanta, she really won me over in our early days together because I felt that we were both values aligned. We approached the work in a similar way. We had sort of an unconventional journey of getting to know each other. It was a short period of time, but what I love about that working relationship is that it is high transparency and it is zero ego. There's just this very fast flow of information. We are super aligned around what we're trying to accomplish and I think that that's the most important thing at the heart of that relationship is, "Just tell me what you want from me." Where this can go wrong and where the relationship can struggle is when you've got a CEO who is maybe not giving you the why behind the goals and thinks that by holding that back somehow they're going to get more out of you. The reality is the better a CRO understands what you're trying to achieve over the longterm and why the better we can align the organization around that. So just brutal transparency and honesty about where you're trying to go and I will get you there. When we are at our best, it is when we've got that open free flow of information and just total transparency about what we're trying to do.

Brett: What else can you share about one big pieces that you two it sounds like just fit together from just a default values perspective? What about the specific effort or things that you put into the working dynamic that have yielded results?

Stevie: Yeah, this has been an interesting way we have grown together. Christina is a product person. She is heavy on written communication and there's a specific way that she processes her decisions and the way she thinks about the business. She also loves to be in the detail. It's so funny because anytime we get new leaders in the door, I think they're a little bit nervous because she'll show up on calls they don't expect and they're like, "Oh, my gosh, am I doing something wrong?" It's like, "No, she just really cares about the details." I think one of those keys in the unlock for us was getting super comfortable showing her everything. This is not a natural part of most CEO-CRO relationships. I think we want to report good news and we want to report up what's working. When I got comfortable showing her the entire organization warts and all and telling her what wasn't working, that was when we really started to succeed together and that was uncomfortable for a long time. Now, it's second nature because I trust her with it. I understand she just wants to be in it. That was one. Then really just trusting that when she has told me what she wants, that I don't need to triangulate the why or that there's more to it. We have come to this very high trust relationship than when she says something, I trust it completely and that allows me the freedom to then go execute on that.

Brett: Why do you think it's your job not to pressure test it or push it or-

Stevie: I do still pressure test it, but in a different way. It's not because I don't trust it. What I do now is I make sure I deeply understand it. I think early on I was maybe nervous to ask questions when she would give me a directive or give me some kind of guidance, and that nervousness led me to attribute all sorts of explanations to what she was asking for. Now, when I pressure test it, it's not because I question it or I disagree. I want to deeply understand how she's thinking about something so I can be sure I'm delivering what she actually wants. So I question now for deep understanding versus trying to figure out is there something more to this than I think there is. So it's like a higher trust inspection so I can calibrate what I'm delivering for her.

Brett: What do you two still disagree on or just can't quite see eye to eye on?

Stevie: I think that there is always a natural disagreement between a CEO and a CRO about speed and risk. I am very naturally inclined to both go fast and take bigger risks by the nature of my role. By the nature of her role, she wants us to be methodical. She wants to make sure we have fully thought things out end to end. So whether that is what markets to enter or how we should bring a specific product to market or how we want to message versus a competitor, she's always a little more risk-averse in those conversations. I really value it. We don't always agree on this stuff and I think that that is a good thing because in the talking that out, we typically come to a better solution than if we just went with my pedal to the metal risk answer.

Brett: How do you think about being a CRO in a market that's fiercely competitive? Is there any difference in how you go about your work in a very competitive market as opposed to more of a green field or-

Stevie: It's extremely different and it has really removed any ability to be lazy in any area. In the grand scheme of things, there are times I would've told you that the intense competitive nature of our market is painful or frustrating or there have been points when it has felt so hard. It has also made us infinitely better. I think the biggest lesson for me is that you need to find the sweet spot of not being overly focused on competitors, but also learning to respect them at such a level that you can see what's not working. You can see what they are doing that is working and have enough respect for it to recalibrate and learn and get better. So you don't want to obsess because I think that that is an easy way to go super wrong when everything you're doing is about what they're doing and how you respond to it, but you need to be open to it. You need to learn from it.

Brett: So I wanted to wrap up with asking you who would you say has had the biggest impact on you and your career? Maybe because you talked about two important folks, there's another one that comes to mind, but you can highlight one of them as well.

Stevie: I mean, definitely the true answer is George at Twilio. He just opened my eyes to a different way of thinking about how to scale a business. He gave me exposure to an analytical approach to go to market that I had never seen. So it's almost like that was the infancy of my understanding of how to go systems first was learning from him. He had a really unique journey in that he started at Salesforce as an intern, and 13 years later, he was the CMO of Salesforce and then the COO, and so his journey was really inspiring. So that was the most transformative mentor I have had. That said, when I go back to my early career, I started as... I had been a pro video gamer. My first sales job was selling to video game company. I was selling payments platforms to them, an there is a woman that was the COO of a company that was one of the early mobile games companies called JAMDAT. Her name is Nanea Reeves, and she at that time was one of the only C-suite women that I had ever met, and she was a leader in an industry that was like 99% male. She was smart and unapologetically herself. What she modeled in those early days made me realize that it was possible to get into a role like that. So for me, she was truly the first person that opened my eyes to a bigger career.

Brett: Great. Thanks, Pam. Thanks for spending the time.

Stevie: Thank you.