STEVIE CASE

>> Craig Gould: Stevie Case, you are the CRO, of Vanta. Vanta is a leader in automating, security and compliance, helping companies simplify governance, risk and compliance so they can scale with confidence. I want to learn so much about your role and how you got there and how you manage this organization, especially at scale, and how you have gone from product market fit to execute exponential growth as you guys have kind of navigated this path. But Stevie, I ask all of these C level executives the same first question, which is, what are your memories of your first job?

>> Stevie Case: Oh my gosh, I have a, a really fun first job. So I grew up with a dad who was a biologist and a teacher, public school teacher. And that was not just a job to him, it was very much an avocation. So we did all sorts of science stuff in free time and that included growing up on this 300 acre piece of land in the middle of rural Kansas. And it was this original tall grass prairie. And we lived there because my dad was both the caretaker for the land and he was helping fundraise to try to save it and preserve it permanently and as a state park. So he did succeed in doing that. But my first job was working for him on that land. And he ran a summer camp for kids there called Outdoor Education Laboratory. And so my first gig was, ah, was I was called a grub, which, you know, after the bug. So my job was essentially clean the cages of the animals. So clean out snake cages and clean up after prairie dogs and lizards and turtles and sweep out the barn. And then eventually they let me start talking to the kids and teaching the kids.

>> Craig Gould: It sounds like a very Laura Ingalls Wilder sort of upbringing. And do you find anything that you still take with you from that first job?

>> Stevie Case: Oh, yeah, yeah. I mean I very much grew up on the land and outside and I still find that very grounding. It was a great gig. I loved it. I made 50 bucks a week. I worked full time. And you know, that experience of, getting to go alongside the kids, you know, we would take them out on nature walks. And one of the most visceral memories from that experience was we would every day take them out on this nature walk. And one of the things we would do is sit them down next to a creek and make them be quiet for several minutes and try to listen and pick up what are the, how many different sounds they can hear and just have that moment of quietness. And I still have flashbacks to that experience all the time. I try to channel it when things feel daunting and, just that experience of, like, you can be working and you can be doing all kinds of active things, but you can still create that moment of quiet. Still really sticks with me.

>> Craig Gould: How do you do that in your current role? I mean, how do you carve out time for centering yourself in a day or in a week? That has to be really intentional, right?

>> Stevie Case: It does, yeah. I mean, part of it is the. The places I put myself. I really try to be thoughtful about creating that time and space intentionally in advance. I, do not always succeed at that. It’s. It’s aspirational a lot of the time, but, you know, I try to, like, really listen to the rhythm within the day, and if I really just have to take a moment, I. I try to honor that and do it, you know. I also find that, like, I have to travel a lot, and I’ve traveled a lot these last couple of years. I have really changed the way I do that. For example, I used to rush in. I would take Red Eyes. I would, you know, maximize my time. And I’ve really changed that to create some space for myself to enjoy where I’m going as well, because I find it’s the only thing that makes it sustainable. So I try to remind myself, like I’m trying to run a marathon, even though it feels like a sprint every day. So I go to Australia a lot, for example, and now what I find is I’ll leave on Thursday or Friday night so I can get there and enjoy the weekend. I try to take that lesson from early in life. And I’ll go outside, I’ll go walk around somewhere, and I’ll create. Even if I’m tired, I’ll create that unique experience for myself.

>> Craig Gould: Stevie.

>> Stevie Case: If.

>> Craig Gould: If I were to go to YouTube and search for Stevie Case, inside of the first five or six videos that would pop up would be a video from 1997 talking about Stevie Killer Creek Case, for those that don’t know. Can you talk about your second job?

>> Stevie Case: Absolutely. Yeah. Another unique one. So I was the world’s first female pro gamer. And this was in the early days of online gaming. I played first, person shooters. Quake was my primary game. And this was just really, at the advent of the Internet and, you know, games were just becoming multiplayer. So to compete, you would go into the console of a game and you would literally be typing the IP address of a server to connect to, and we could get online and compete against others. So I ended up doing a lot of that. I was in college at the time, living on the honors floor of a dorm and played Doom, got into Quake, got competitive, was on a team that won the first team tournament ever. And then I ended up playing the guy who made Quake, who designed it and I beat him at his own game. And that sort of snowballed into a career. And really if I look back, my intent at that time was to be a lawyer. I was going to go, I was poli sci, I was going to do pre law at the University of Kansas, but I ended up dropping out to do games and I played them professionally, I moved into making them and ultimately that was the detour that led me into tech.

>> Craig Gould: Do you think he would have been a good lawyer? Because I mean it’s a certain skill set and you’re probably at the point in your life where you now know a number of lawyers. Like do you, do you think, do you think it would have satisfied and checked all the boxes for you?

>> Stevie Case: I do, yeah. I still love to my legal team at work, hates it because I love to do my own red lines. Like I still get a lot of joy out of that idea of being a lawyer. I mean until just a few years ago I really entertained going back to school and getting my law degree and, and doing that. So I think I would love it. But truthfully, the direction I wanted to go there was not corporate law. It was my deep desire to go the path of constitutional law. And I had just like a lot of passion for political science and law and ah, service. You know, I grew up my dad being that teacher, my mom was a social worker and a nurse. So in my house growing up there was this deep idea of being of service. And when I thought about law, I didn’t think about corporate law and contracts. You know, I thought about it as a way to help people, a way to advocate for people. So I thought about you know, working with people who are victims of domestic violence or working in immigration law, those kind of areas. So I could still see being very passionate about that line of work.

>> Craig Gould: Tell me about Vanta. You know, you mentioned you went from gaming to the gaming industry into technology. Somewhere along the line someone said that you, you should be in cells, that you, you’ve got the personality to convince somebody to part with their money. And then you know, eventually there, there’s Twilio and, and now there’s Vanta. Tell me about what it was like stepping into the, the CRO shoes at Vanta and what you found when you got there.

>> Stevie Case: Yeah, so Vanta is a really unique company. And I had not been a, chief revenue officer before. This was my first role of that kind. I had had a long career in sales. Chief revenue officer means a lot of different things in different companies, but here it means sales, customer success, revenue operations, partnerships channel, all sorts of things. But when I arrived at Vanta three and a half years ago, it was a much smaller company. So I joined right around 150 employees. the company clearly had really strong product market fit. And that early product market fit looked like very high velocity inbound sales motion, a sales team that was just really taking orders. Things were flying off the shelf. And the use case at that point in time for Vanta was we had a platform that was helping automate compliance. And really what the heart of the work was was we were helping founders of B2B software companies achieve SOC2 compliance and get through a SOC2 audit successfully. And what Christina Cacioppo, our founder, identified at that time, she’s a product person, she had built software in the past, was that we had all these very tech forward software people building software and then to bring it to market they would go to sell it to other companies and the other company would say where’s your sock to. And so that happened to Christina and she went to go, you know, figure out how to get a, get a sock too. And she realized that the whole process was just so backwards manual. She was working with, you know, an auditor, a CPA who was non technical, didn’t understand software. She was taking screenshots of her AWS config. You know, it just did not make sense, sense in a tech forward world. So what I found was a team that had really unlocked this incredible need and this use case and was really helping drive a lot of revenue for founders by unlocking it. So lots of customer love, really powerful market fit, and a team that was excited and growing. But we were still early days. You know, I had a team of about 20 folks when I joined and we’re focused mostly here in the United States. It was a lot of inbound and a lot of excitement.

>> Craig Gould: I’ve tried to do my research on you and I hear you talk a lot about the math of it all, which is really about the metrics, the analytics, the things that you can track, looking at the data, trying to make sure in real time what the data is telling you. I’ve heard you say that when you showed up, you didn’t have a lot of data in front of you and you, you had to make decisions with what you had, what small dashboard you were given. Can you talk about some of the challenges there and what you’ve learned?

>> Stevie Case: Yeah. So those early days we were so fortunate that we had this incredible product market fit. But you’re right in that we really did not have any data at that time. You know, one of the foundational activities of a sales team is forecasting and being able to predict what the outcome will be within any given period of time. We weren’t doing any forecasting. We had no real insight into who we were selling to or why we were succeeding or at what rate. And that sets a number of really tough situations because, you know, coming in, the first thought and the first thing I was encouraged to do was hire because it was like, okay, demand is off the charts, there’s obviously a lot of opportunity here. Go grow the sales team so we can sell more. And you know, I went to do that, but there are a lot of really important decisions you make when you go to grow a sales team. You need to understand deeply who, who are we selling to? So where is more opportunity? what does that sales cycle look like, how long is it, how complicated is it? And then you want to bring in a team that can really serve that real opportunity. And one of the first things I learned in that process was I just hired a bunch of, junior salespeople who I thought could sell to startups. Well, it turned out our opportunity was actually a lot more than startups. And that was one of the first kind of foundational misses and, and things that I realized was, wow, there is actually a lot more complexity in the interest in this product. It’s not just startups. There’s an interesting set of SMBs in here. There are some mid market companies, there were even some very large enterprise logos in the mix. And when you hire a team that’s meant to sell to simple startups and you know, you put them against this much more complex funnel that can be really challenging. So that was one of the first eye opening things and it took me about a year to a year and a half to really get the right measurement in place to understand deeply what was going on and be able to make better informed decisions. And that’s when we really got to start to unlock that larger opportunity that was much more complex and robust than just SoC2 for startups.

>> Craig Gould: If you could do that over, how could you do it over? Is there, is there something you could have done differently or is there something you would do differently next time?

>> Stevie Case: Yes, multiple things I think Lesson number one for me was you really cannot just take others playbooks and apply them to your business. And I think that’s one of the most important role. It’s one of the most important things I’ve learned over and over in this role. Because when you’re in a role like the CRO role, you get advice from everyone. Everybody’s got an opinion about what you should do. Everybody wants to say, oh, well, XYZ company did it this way, therefore we should do it that way. If I’ve learned anything, it’s that every business is extremely unique and you do have to collect all those data points about what other companies do, but you’re always going to have to put your own spin on it. So taking another company’s playbook or somebody’s advice who is not in the business is usually a bad idea. You really have to develop your point of view. And that brings me to the foundational thing I would do differently, which is I didn’t fight hard enough to stand up that measurement infrastructure early. We did it, but we did it at a more measured pace. If I could go back, I would get all of that measurement in place much earlier as project number one, before I started adding other people into the business or making decisions about where to invest. I think that can be done very quickly, especially these days. There’s such great tools out there. You can stand up meaningful measurement in 30, 60 days. Doing that first and then coming with your unique perspective rather than somebody else’s playbook. If you do that, it’s kind of hard to go wrong. You’re making better decisions with more data, more informed decisions, rather than just trying to move fast because that’s what seems right on paper.

>> Craig Gould: What did you find to be the right variables? I mean, how do you. How do you even identify the right variables? I mean, it seems like, you know, when you don’t know what you don’t know, how do you even go about identifying that? do. Do you have to throw a lot of things up against the wall and see what sticks? Because I imagine you were trying to figure out if, if I concentrate on this thing this week, is this lever making a difference? Yes or no? It was just lots of a B testing. I mean, am I imagining correctly or that’s correct.

>> Stevie Case: That is act. It’s actually much simpler than I think it can be made out to seam from the outside. When you’re thinking about growing revenue, there are really only a few things that matter. And then there’s a lot of detail art, science that goes around it. But at the core it is, where do you drive pipeline and demand from? So can you find sources to create opportunity that are repeatable and that you can scale? That is foundational. That is kind of problem number one that everyone needs to solve. We without that, you’re kind of dead in the water and you’ll have a lot of people wasting a lot of time throwing things at a wall, trying to figure things out. But it really is that simple. So, you know, Vanta, in the early days, a lot of that was inbound interest driven by search engine marketing. That was really our first channel that scaled. And you know, that is something that plateaus after a while. There’s only so much search traffic in the world on, you know, your keywords. So then the next mission is, can we find another channel to drive inbound interest and to drive awareness? And for us, that, started to grow into things like podcasts and started to grow into other types of events. And so we started to see if we invested in these other areas, we could create more opportunity for the team. So that foundational problem was one of the big first ones to solve. The second is really, who are we selling to? Are there more of them in the world? And can I just keep getting better and better at identifying them, making sure they know what I have to offer, and then telling them a story that’s compelling? So, you know, you measure that in terms of conversion and win rate, but it’s kind of that simple. And when I go back to the early days of anta, you know, we had a couple of areas of opportunity that it took us a while to identify. And one of the biggest was that we weren’t just selling to founders, we were actually also selling to security and compliance professionals. And ultimately we were selling to CISOs. We were selling to these chief information security officers. And the entire way that those buyers perceive the value of a platform like Vanta is completely different. So while we were helping founders get SOC2 compliant, Aciso comes to Vanta. For them, we’re an AI trust management platform and they’re managing an entire, enterprise risk program on our platform. It’s very, it’s same technology underlying, but the paradigm is so different. So you got to suss that out to be able to get successful with each of those Personas.

>> Craig Gould: I imagine you’re really having to use that feedback to collaborate with the product team on specifics because, I mean, those are two drastically different customers. And I think of like something like accounting, you know, the company that is going to use QuickBooks isn’t the same company that is going to go to Anderson. It’s totally different. Right, but I mean, but the thing is like the underlying value proposition is the same. So is the delivery, is it the size? Is it how you plug into their systems? Is that where it winds up being different?

>> Stevie Case: There are product elements that are different. You know we, what we found in those early days is that the core platform that we had built actually could serve the needs of different sizes of organization with just a few small tweaks. It’s actually one of the things that I do think makes our business really special and unique. Is it, it’s rare that, you know, it’s, you usually see that QuickBooks use case that a piece of software is great for one size of business, but maybe not another. Vanta is kind of unique in that we can serve any size of business. So what we saw there was an opportunity and that original platform, that automated compliance, we started selling it across all of that spectrum to the different types of buyers. Then what we did, and this was kind of a big revelation and inflection point was it was really clear that we had this opportunity to work with CISOs upmarket in enterprises in mid market. And so, you know, anytime you’ve got a sales team and you put them against too many different things, they will gravitate towards the easier thing. So you know, we were looking at these enterprise opportunities but we weren’t doing particularly well at winning there. And that’s natural. So what we ended up doing was creating a team dedicated to pursuing those opportunities. And then we built a feedback loop so when they had conversations with CISOs or they had conversations with these much more complex companies and organizations, they, they could get this feedback loop back to product to say, here’s what we’re observing, here’s the opportunity we see. And that led us to an inflection point a couple of years ago where as an organization we all came together as a leadership team and said, okay, there’s clearly an opportunity here. Are we willing to put more resourcing in to go after that opportunity and create a version of the platform that deeply serves that need and starts to expand horizontally. And we made the decision to do that and it was because we had put this go to market team against the opportunity to learn. And they became that learning engine to teach us what really mattered. So the more we learned, we evolved the product, we put more resources on it and now although it is one platform, we really have these very different teams parts of the business that are serving founders and that are serving CISOs, all coming back to that one core trust management platform.

>> Craig Gould: Yeah. It reminds me, a long time ago I saw a sell sheet for this particular product. It was like a wood chipper, but it was the size, of a big rig. It was like two different sell sheets and one sell sheet it was talking about being a wood chipper and then an identical sales sheet that said it was for use in recycling. Right, right. And so it was like, I imagine you’ve segmented your sales guys so that your SMB folks aren’t the same guys that are dealing strictly with, with enterprise because I mean they’re, it’d be hard for them to kind of be switching back and forth. And I imagine that there’s probably a higher return on those enterprise clients. Right. Because they’re likely. I’m not sure how the pricing goes, but there are probably more licenses involved.

>> Stevie Case: Or it’s, I mean, it’s unique. Our business is unique this way. What we find is that in serving startup founders, we are unbelievably efficient. So while those are typically smaller contracts, you know, we find we can serve them really effectively. We get the use case, we get them through. We’ve automated more than 80% of the work for them to get compliant. So our efficiency in that part of the business is off the charts. And what we’ve really done is build an organization. It’s not just sales, it’s sales, customer success, account management. the way we talk about the customer journey, the way we measure everything is built for that startup founder journey. So we have something truly unique for them. In enterprise, they use us in much more complex ways. We have an entirely different set of teams that serve those folks. So it’s, the math is a bit different. Acquiring those customers is more complex, it is more expensive. But what we find is once you get enterprises to adopt, they do stick with you for a very long time. So it’s a longer. You have to think about the lifetime value of that customer. We also think a lot about how do we realize value for them. So this is one of the other big pieces of the transformation over the last few years is we went from a company that, you know, transactionally sort of took orders inbound to one that really thinks about value. So in enterprises you’re thinking about that like multi year, even decade plus value that they can derive from using a platform like ours. That takes a lot more people to realize it is a more complex sale, and then it’s more complex to serve those customers. As well. But once they’re in, you know, they’re asking us what else can we do together? And that’s where we started to expand horizontally. Now we do things like we help with third party and vendor risk, we help them automate security questionnaires. We built a trust center which is like a public facing page for showcasing how they manage security and compliance in their business. So we’ve built this suite of products to help solve more problems and deliver more value for those larger customers. So the startups that start with us in a simple way, the beauty of that is they often grow, they become those SMBs and then mid market companies and then enterprises over time and we want to be with them through that entire journey.

>> Craig Gould: So was creating a post sales organization kind of a logical next step when moving into enterprise in terms of creating that stickiness, Having those customers understand the full breadth of the feature set so that you can build those switching costs by coming alongside and kind of holding their hands?

>> Stevie Case: Yeah, that’s been critical. And we have always had a post sales team in some form that started as a customer success team. A lot of that has to do with the fact that compliance is complicated and even with technology, a lot of our customers want that support and the hand holding. So we’ve got a team that will help answer their questions, help them through audit. And, and that function really did have to grow and become much more complex and thoughtful over time. So the biggest change we made initially was we split that team into two. We kept the customer success function and instead of asking them to do everything, we asked them to focus on customer onboarding, adoption and health. And then ultimately they’re responsible for retention and making sure our customers stay with us. And if they’re successful, they typically do. And then we also built an account management function and that account management team was really focused on value realization, making sure that our customers understood once they got successful with the first use case, that we could then help them with these dozens of other use cases. So they do a lot of product education and ultimately they are the ones that expand our relationships with our existing customers. Now to that we’ve added everything from an implementation team to we’ve got a GRC subject matter expert team. This is another thing that’s unique to our business. Governance, risk and compliance is super complicated. So we have this team of folks who are like former auditors and former security practitioners and they support our customers as well because there’s all this unique regulatory knowledge and other compliance knowledge they need. So we’ve really staffed that team up to holistically support our customers and ensure that they are successful and they grow with us.

>> Craig Gould: I believe I’ve heard you say that you guys recently, started working with, helping people become kind of certified government contractors. Because there’s certain boxes you need to check on that side, right?

>> Stevie Case: Yeah. There are a couple of these specific regulatory frameworks if you want to sell to the government in any form. One of those is FedRamp, which, if you’ve ever been in a software company that tried to pursue Fedramp, it is incredibly complicated. It is one of those huge hurdles. and we now support that framework. So we help companies to become Fedramp compliant. We do automate a lot of that work. We also support this new standard, called cmmc. CMMC is an interesting one. It is a new framework that as of November 1, is going to be a requirement for basically everybody who sells to the government in every form, not just software companies. So if you’re Bob’s Metal Shop in Raleigh and you’re selling nuts and bolts to the government to make aircraft, you have to prove your CMMC compliant. And that’s really, you know, sweet spot for us to help small businesses succeed at doing this in a way that is less painful and more automated. So those are two areas that we’re helping. We’re also working directly, with government agencies now. So lots of growth in that part of our business. So, really interesting opportunity to help people modernize the government, modernize the way that the government serves citizens.

>> Craig Gould: How do you manage your sales organization? Because, I mean, I guess your responsibility isn’t strictly sales, but how do you run the revenue side of the house? What’s your mindset?

>> Stevie Case: Yeah, I mean, the single most important answer to that is I hire great leaders. And I’ve got an incredible team under me that are just so talented. And, you know, I believe in building an organization that is high urgency, high agency. So I really try to hire people that come in with the mindset of being a business builder. So we are, you know, not the place to come for folks who are just kind of looking for the playbook and kind of going to execute on what they’re told. I want every one of my leaders to have this mindset that they’re the general manager and owner of their part of the business. And I want them to have the creativity and the ownership to not just do the job, but drive innovation and help us learn what’s next. So, you know, we started with that base layer of, getting my leadership team set up across the sales organization. And then as we segmented that we needed leaders for each segment of that sales organization, we expanded internationally. We needed international leaders to lead the different geographies. We need leaders for customer success, for account management. I also have a really, rock star revenue operations team. So they run all of our operations, our systems, AI innovation as well, enablement and learning. So basically we’ve put together all of these key functions, each with great leaders. And my goal, the way I, the only way I’ve seen it work at scale is that I need those leaders to be so good that they can operate their team without me. And for me, one big green flag is if a team is running and they don’t need my input. Awesome. That’s a great sign. That is. I think some newer leaders get freaked out by that. They’re like scared when they’re like, oh, the team is not asking me for anything. That’s actually a great sign because that’s the only way you can build an organization that scales. You know, when I joined Vanta, My team was 20, I think I looked this morning, and I’ve got 550 people on my team. And that only works if most of that organization does not need my input on a daily basis. So having great leaders who know how to run, who have the empowerment and the agency to like get it done and to be creative, is the only way to make that scale work.

>> Craig Gould: So do you give them the autonomy to be creative and kind of skunk works of their, their own ideas? Or is there a point where they sort of need to raise their hand and say, I’m thinking about doing this. Are you okay with that or is it more? I’m going to try it. Hey, I, saw a marked increase. This is why we increased. If anybody else wants to implement it other, other places, like what do those conversations look like?

>> Stevie Case: I mean, it all starts with a framework around the expectations. So the thing that my leaders are all clear on is we have very specific targets for the year down to the penny. So every team understands their mission and they understand exactly their constraints. So they know what headcount they have, they know what budget they have. So everybody’ their constraints and their targets outside of that. I do want them to run those experiments. I really don’t want them to feel like they have to come to me to run experiments. You know, if it’s some kind of huge investment, we’ll have a, we’ll have a conversation about it. But all of those leaders have the autonomy to Go run. And then the way that I organize my teams is that we have this weekly inspection cadence and it’s organized around the set of forecast calls. And in those forecast calls we are talking about like, what is the forecast, what is the number we’re calling. But we’re also having the conversations that you describe, which are, here are the experiments we’re running, here’s something we’re trying right now, here’s the impact we saw. And on those forecast calls, I want my leaders listening to each other and sharing what’s working. And often those forecast calls drive an outcome that is, oh, this team in North America in the startup segment tried this and they saw win rates go up 10%. It’s like, great, okay, can you guys get some time with the other startup sellers globally and teach them that play? So there’s this opportunity once a week to do cross pollination of those ideas and the experiments and to learn from each other. And I like to describe my team as if it’s successful. We are like a learning machine. We’ve got the mechanisms to surface learnings, good and bad. What’s working, what’s not working on a regular basis with high transparency. And then we all address that together. We learn together. And if that team can learn without me, it can scale infinitely. So that’s really the magic.

>> Craig Gould: A lot of the conversations I, have on the podcast with C level executives, they attribute at least part of their success to what they discovered in terms of mentorship. I can’t tell you how many I’ve spoken to that have talked about creating their own personal advisory board. I would love to hear your perspective, like your relationship with George Hu. Can you talk about the notion of mentorship and being willing to have somebody to reach out to and bounce things off of or set you on the right course?

>> Stevie Case: Yeah, this has been critical and I was very lucky to be George. During my time at 20 Twilio, George was our COO there. He ran all things go to market and more. He had come from Salesforce. He had a really interesting journey at Salesforce. He started as an intern, he ended up as the CMO and then the COO and as really Mark Benioff’s right hand guy for a long time at Salesforce. So the beauty of George is that he had seen what hyper growth looked like and he had helped author that playbook. And so that’s what he brought to Twilio. And I had joined Twilio just before the ipo and George joined about six months later and when he got there, we really, you know, it was all plg. It was all like product led growth. And we were just at the early stages of building a sales team. Sales team then was 20 people globally. And, you know, George brought this incredible playbook there and he knew how to scale. And what I really liked about him is he was just very transparent. And I was lucky that we hit it off early. You know, I never asked George to be my mentor. That’s one of the things I think stands out among leaders I talk to. And it’s certainly been my experience. I don’t technically have anyone in my life that I’ve ever asked to be a mentor, but it’s these more organic relationships that have built. And that was very much the case with George. So I was actually a salesperson at Twilio at that time, carrying a bag. I decided to come in as an enterprise salesperson. And I got to know him because I was one of the only enterprise salespeople. And I brought him along to meet my customers. And like, we traveled together and we went to these customer on sites. We had a lot of car time driving customer site to customer site. And through that time, I kind of let him see the good, the bad and the ugly. Like, I didn’t try to keep everything too clean and buttoned up. I just sort of like led him along for the ride. And I think he really valued being able to see the reality of what was going on. And through that we built the relationship. And then, you know, over time, he became clearly my mentor. And, you know, he would show me always sort of like, what is the next thing I need to learn. And so he was challenging me in these ways to continue to level up. And so now, you know, he’s been fundamental to my learning. I would not be a Sierra, without George. And in this current role, I frequently text him and just sanity check stuff, ask him for feedback, ask him if this is normal. I also just text him as if he’s my proud dad and say, george, look what I did today. You know, like, I did this thing. It’s pretty cool. And so that’s been, a really neat relationship. But I’ve got this extended group of folks like that who have been amazing to just check facts with and get feedback. And like that network has been critical. Without it, I would be lost.

>> Craig Gould: My impression of you is you’re, you’re highly curious and I can imagine that you would have been kind of non stop picking his brain. Can you talk about the value of curiosity? Not Only in your career, but even just in the sales process. You know, curiosity and trust are two terms that just keep on coming up over and over and over again when I’m, I’m talking to CEO level executives. But let me ask you about curiosity.

>> Stevie Case: Yeah. It is the number one thing that I look for in people I hire and it is the number one characteristic I attribute my success to. I mean, you are very right in that the time I spent with George, I’m sure I drove him nuts with like a million questions. I, you know, he was so forthcoming though, and it was so helpful. You know, I would try to really just understand how he looked at the world and you know, what, how he thought about the job. One of the things I asked him at one point that stuck with me was he had been cmo, at Salesforce, and it was his first marketing job ever. And I asked him, like, how do you do that? Like what, how do you approach taking a job within a domain you have no experience at? like, what do you do? And he gave me some great advice about, like, the most important thing is setting priorities. And you’re never going to get those 100, 100. Right. So just give clear direction and learn more and then you can reset. But it was, it was that process of asking questions that allowed me to understand his mindset and how he ran his business and his life. And, you know, that curiosity, I. It’s what I look for in my team. Like the advice I give to leaders in my org who want to move up is. The most important thing you could do is seek to understand your boss’s job in their mindset. And if you can build empathy for that and, and help them be successful, you will be the obvious person to promote next. Because if you get what it takes to do the job at the next level, why wouldn’t you get promoted? And nobody’s going to hand that to you. It’s not like there’s a training school where somebody teaches you to be the manager of managers. Like, the only way is really to ask and to develop that understanding. And the curiosity’s got to be at the heart of it. So I will take somebody who is curious all day over somebody that’s got a great resume. Because I find that curiosity will always drive growth and improvement. Part of it comes from that sales background. You know, great discovery is the heart of great sales. So to me, that is sort of the whole ball game. And if you’ve got that, it’s hard to lose, I guess.

>> Craig Gould: I’m very curious But I’m also very empathetic and I’m, I’m just trying to put myself in your shoes, walking in as a CRO, having never had that title before. I know that we talk probably too much about imposter syndrome, but how did you gird yourself and encourage yourself and remind yourself that, you know, you were hired because you were the best person for the job?

>> Stevie Case: You know, I don’t even know if I believed that, like, honestly, like part of it is a recognition that everyone in these leadership roles is a human being and we all come with our unique quirks, strengths and weaknesses. And that a lot of driving success in these type of roles is confidence. It’s manifesting it. And if you spend your time questioning if you’re the right person and being unsure and holding back, you’re not going to manifest success in your organization. Half the battle is convincing people to go on that journey to put their time and energy into the, to the fight with you. And nobody wants to do that for a leader that’s hesitant or unsure themselves. So, look, I look back at that early part of my journey and I made so many mistakes, but I do have a lot of grace for myself in that because I think that’s the case with everyone who takes this job for the first time. I don’t think I’m unique in that. And all I can do is learn from those mistakes and try to do better and try to learn. And I do think that over that time I have gratefully developed a lot of confidence that I do think I know what I’m doing in the role, but that it takes years to build. And everybody who’s a first time CRO is going to have that experience of being unsure. So back to George’s advice. Sometimes the best thing you can do is just confidently pick a direction, get your team all pulling in that same direction, and then learn and course correct as you go.

>> Craig Gould: How do you get people to follow you? Is it authenticity? Is it vulnerability? But not vulnerability to the point that, that people think you’re not confident? I mean, is it that, you know, again, I think the word you use with George was transparency. How do you get people to follow you?

>> Stevie Case: For me, it is a combination of authenticity and vulnerability. You know, we, we recently had an offsite. And I think one of, one of the questions, we asked as an icebreaker is how are you different outside of work versus at work? And my answer was like, not. I’m not, like, I am very much. What you see is what you get. There’s no guile. I’m the exact same person, in my life as I am at work. And I think bringing that level of, authenticity is key. I do also think people love to be on a winning team, and I deeply believe in building a winning culture that celebrates people, that celebrates winning. People want to be on a winning team. And that doesn’t mean that you lie to people or you tell them you’re winning when you’re not. But it is about energy and momentum building and celebration and recognition. And for me, it’s not always win or lose. It’s like win or learn. You know, we’re winning a lot of the time, and I am very grateful for that. We’ve been doing incredibly well as a business, and that, that makes it a lot easier as a leader because people are excited to be a part of that. But we do have places where we don’t always win or things go wrong. And I think when that happens, being highly transparent, owning it and making a plan to get back to winning is the best path forward. And people want to be a part of that momentum and that energy and the acceptance that it’s not always perfect, but when we don’t win, we find a way back to that right path.

>> Craig Gould: Stevie, one of the fascinating things about your career is that you’re not only CRO at Vanta, but you’re also part of the 20 VC operator network. 20 cells. And, you know, 20 VC is kind of unusual in the space because it kind of grew out of media. Harry built a massive content platform before even launching the fund. And so I’m just wondering, that emphasis on storytelling and consistent content, it seems like that’s really influenced 20 VCs ability to attract founders and LPs. And, you know, what kind of impact does that visibility have on a younger fund trying to stand out in a crowded market?

>> Stevie Case: It’s been huge. I mean, Harry is incredible at that. He’s a great storyteller, but he’s also very curious, you know, the way he created these funds. So I’m a part of this 20 sales fund, which is, you, know, a seed stage fund that is, you know, group of operations operators. There are eight of us, eight really incredible women that are all go to market operators. And Harry had this concept of creating these smaller seed funds, one for sales, one for product, one for growth. And his idea behind it was just recruit incredible talent, set us free to go talk to founders and source deals and that just like that network. And the curiosity would drive these great outcomes. And I Think it’s a really cool model and it’s been incredible for us. I mean for me, the experience and the exposure to have this fund and be able to deploy capital to support great founders, you know, I really view it as an opportunity to educate myself. I think we found as an operating group too that as, as experienced go to market operators, we can add a huge amount of value for technical founders who don’t necessarily have go to market experience experience. So I think, Harry’s curiosity really drove so many of those key insights that led to the creation of these funds. And it’s been this amazing network effect. So I feel really grateful for that and to be a part of it.

>> Craig Gould: Well, do, do you think other mid sized funds will adopt that same playbook of investing in content and narrative to compete with the big guys? Because I mean it’s, it’s a crowded space and like how do you, if having $500 million is table stakes, how do you differentiate yourself?

>> Stevie Case: Yeah, I think they will have to because if you look at the landscape today, I mean there, there was big story online today about this whole dynamic shift between founders and venture capitalists and you know, VCs chasing these AI founders and saying please take my money. You know, it’s become incredible, incredibly competitive. So I do think that raising your profile, having that kind of brand, I think brand really matters because the truth is once you get into the journey, you know, like the fund is helpful, but a lot of it does have to do with brand and network and I think media has become a huge part of that value proposition. So when you’ve got great media to back up the fund, that’s a real value add for your fund founders and for everybody associated with it. So I do think that that is the direction in the future. And Carrie’s got a great head start, he’s done a beautiful job. But think like personal branding really matters.

>> Craig Gould: You.

>> Stevie Case: I spend a lot of time on LinkedIn and a lot of time building personal brand there and I have found that like really owning your own story is super valuable and just making yourself publicly available so people can know you. I think that’s kind of the type of attention economy that we’ve got at this point and it really does deliver value.

>> Craig Gould: Well, that sounds like the perfect segue to Stevie. If folks wanted to get hold of you, if people wanted to learn more about Vanta, if they wanted to reach out to Killer Creek, what’s the best way to find you and Vanta out there in the websphere?

>> Stevie Case: Yes, you can find me on LinkedIn. Stevie Case on LinkedIn. I post a lot. I’m really active there, so love to connect there. Vantavanta.com is where we’re at. We are also very public on, on social and all the places. We’re doing our user conference here coming up in, just a few weeks here in November. That’s going to be Vanticon. So we’re out there and easy to find. We’re at every cyber security event you could imagine and as well, so would love to connect.

>> Craig Gould: Awesome. Well, Stevie, I can’t say thank you enough today for being my guest. It’s really been a delight.

>> Stevie Case: Thank you so much for having me.

>> Craig Gould: Absolutely.