Manage Resources & Create Results! Vanta's Chief Revenue Officer, Stevie Case (Podcast 237)

Whether it's sales or being a CRO or being a gamer, it's really all about resource management and numbers and understanding the levers you can pull to get outcomes. It really does boil down to building that strategy and understanding how to influence people in a game. It's a very one person endeavor and you're driving those outcomes yourselves and making strategic decisions. When you get into sales, it becomes sort of two player. You have to start to think about the person you're trying to do business with, what matters to them, how do you create outcomes for them and your own company. And CRO just takes that to a next level of thinking about dozens or hundreds of people. How do you manage those resources in a way to create a certain outcome? So it all comes down to the same stuff, just curiosity, asking lots of questions, doing discovery and understanding where your levers are that you can pull to create the outcomes you're trying to create.

Today is Vanta's Chief Revenue Officer, Stevie Case. Stevie oversees Vanta's Go to Market team to support the company's rapid growth. She brings over 15 years of sales and business development experience to the new role, most recently serving as Vice President of mid market Sales at Twilio, a market leading cloud communications platform. Joining as one of the first account executives, Steve Stevie played a pivotal role in establishing Twilio's enterprise business with key Fortune 500 customers, generating more than 400 million in annual recurring revenue. She helped grow the sales team from a dozen to over a thousand team members. Stevie also supports startups, serving as an angel investor and an advisor for the past decade. So Stevie, welcome to the Second in Command podcast.

Thanks so much. It's great to be here.

Yeah, selfishly I want to like dive in about all this angel investing. So I'll just add that to the list of like topics to ask you about because I've got some, some super interesting questions hopefully and then I'd love to hear some of your advice but walk me through a little bit about kind of how you got into the role that you're in today. Kind of what, what got you in your career to being a CRO and, and really the second in command of Vanta.

Yeah, I, I had a very non traditional path to the role is the honest answer. I started at the University of Kansas thinking I was going to be a lawyer and was going down a pre law path. I ended up dropping out of school and starting my career as a professional video gamer and that is the thing that indirectly led me into tech. So I played video Games professionally. I ended up making video games for a living. And then I ended up sidestepping into mainstream tech. I was working at Warner Brothers producing mobile video games, and I had a vendor who approached me and said, I need a junior salesperson. I think I could teach you to sell. Like, what do you think? And the truth was, I thought it sounded really uncomfortable, and I had no idea what sales was. And so I thought that I've always been about a challenge, so I took that role. And I've been in sales ever since and worked my way up. Have had experience at small companies, big companies, and Twilio was the place that really taught me how to scale. So I went from being an individual contributor to running a $400 million business there, growing a huge team. And so when. When the opportunity came to come over and play that scale playbook at a growing startup at Vanta, I jumped on it.

Hey, so walk me through the logic or the mindset of. Of going into sales. Was it to get out of gaming? Did you not think gaming was professional or something back in the day and sales seemed like a career path or. Because you said junior sales role?

Yeah. I mean, the honest answer is I just didn't know what sales was. And gaming is one of those things. I had a really interesting path through gaming. There's actually. So I just had a story about my background in gaming come out in Vanity Fair yesterday.

Okay, we're asking about it. It's coming.

Yeah. Okay, good. We'll talk about that. And it's all I knew. You know, I was just. I'm a kid from Kansas. I dropped out of college. I had no sense of the world, no passport. Like, I really was not worldly and had not seen a lot. So I didn't have an idea of what sales was. It just seemed like a really good challenge. It sounded unfamiliar. I didn't know what it was or what it meant. And it was something I wanted to learn about. I was very. I was a shy kid. I was really shy. And so it felt like a big challenge. And I would. I love a challenge. And it felt like something I could learn.

Wow. Okay, tell me. Tell me about gaming. I mean, my kids are gonna lose their just finding out. I'm talking to a former professional gamer. That's kind of cool. Anyway, so how old were you when you were doing that? And. And what was that like? Like what? And what is it? What was it then? Because I guess we've had some exposure to it in the last 10 years.

Yeah, it's radically different today than it was then back then. So we're talking late 90s. And I was, I went off to University of Kansas when I was 17. It was quake and Doom. So early days, first person shooters. It was really early days of the Internet. And with Quake coming out, it was one of the first games that you could actually play competitively online. You were going into a console inside the game and typing the IP addresses of servers to connect and very basic text chat, but it was multiplayer and IRC was a thing. There was this like very beginning of the, the social aspects of the Internet and I formed a lot of friendships and I ended up joining a team. And you know, back in these days, what it looked like was typically land parties, it was actually some online play. But you know, we would have people drive from all over the country. I lived in this house with a bunch of friends in college and we'd have people drive from all over the country and bring their 21 inch CRT monitors and like sit in a room and play Quake together on a land, an actual physical land. So that's what it looked like back then. And I got sponsorships from joystick companies and I joined the very first league and was actually paid full time to play the game competitively.

Wow. Okay. So knowing what the space is today, is there not something pulling on your heartstrings to go back into that industry at all?

No, I will, I will say this, I will always be a gamer at heart. The industry itself, I think is a tough place. And it's a particularly tough place for women. Not to say mainstream tech isn't. It certainly is and can be. But I have managed to carve a path in traditional mainstream tech that I find much more hospitable. I'm 46 now. I'm a grown up now. And as a grown up adult woman, like mainstream tech has been much open to me than gaming. So as much as I love gaming, it is now a hobby as opposed to a profession.

And you haven't ruined your hobby, which is kind of cool too, right?

That is true.

Yeah. I remember my kids trying to explain that gaming was a thing and they were professional and I thought they were lying to me. I'm like, you guys are idiots. You're like 10 and 8. That's really funny. Like, is it? And then I started hearing about it. I'm like, what? This is like, it's a big deal.

You can make a huge amount of money. I mean, what I will tell you about that is we had this vision back then of Gaming being a real professional endeavor and having true competitions in arenas and having it on ESPN and in the Olympics, like that was the vision.

Oh, so you thought you talked about it too.

Oh yeah, oh yeah. That, that was, that was what we all believed would come to fruition and really work there in a lot of ways. There are people making hundreds of thousands, in some cases even millions of dollars as pro gamers. And it's a real profession for folks today and people do show up to Staples center in LA and watch professional video gamers battle it out.

Yeah. I spoke to the CEO of a professional gaming company in California. I remember his name. Steve I think. Was his name electronic or something. It had like something like lightning or something in my. Is what I'm remembering about the name anyway. Like a multi, multi, multi million dollar business. And he's not even the gamer, he's just like he owns teams and they have houses and trainers and anyway, blah blah blah.

It is a thing. There are gaming houses out there and you know, it's, it's also there are aspects of it that look a lot like real professional athletics in, that requires twitch reflexes. You really do have to practice. This is like eight hours a day. It's a full time job. And you also age out because your twitch reflexes fade at a certain age. In that sort of mid to early 20s, they, they fade and you cannot be competitive anymore.

And my eyesight. My eyesight, yeah.

Bad eyesight's another one.

All right. So then you drop into a junior sales role. Kind of brings you into the business world a little bit. Anything that you've pulled from sales that you still carry with you in your career today.

Yeah. And it's the same thread I pulled from gaming. Truthfully, I think that when it comes down to it, whether it's sales or being a CRO or being a gamer, it's really all about resource management and numbers and understanding the levers you can pull to get outcomes. It really does boil down to building that strategy and understanding how to influence people. You know, in a game it's a very like one person endeavor and you're driving those outcomes yourselves and making strategic decisions. When you get into sales, it becomes sort of two player. You have to start to think about the person you're trying to do business with, what matters to them. How do you create outcomes for them and your own company. And CRO just takes that to a next level of thinking about dozens or hundreds of people. How do you manage those resources in a way to create a certain outcome? So it all comes down to the same stuff. Just curiosity, asking lots of questions, doing discovery and understanding where your levers are that you can pull to create that create the outcomes you're trying to create.

Interesting. All right, I'm going to ask you about Vanity Fair because you kind of just odg shucks that in there that you were just covered in Vanity Fair about gaming. What, what were they writing about? How did they learn about you?

So there's a lot of backstory here. There was a book that came out in the early 2000s called Masters of Doom, and the author was wonderful guy, Dave Kushner, who wrote about those early days of first person shooters and Doom and Quake. And so I spent time with Dave way back, both in the writing of that book and even before he actually came to cover that sort of LAN party gaming culture in 1996 when I lived in Kansas. So that's first time I met him. He was doing a follow up on everybody who was in Masters of Doom.

That's cool.

So he called me up earlier this year and it was sort of a check in, like, hey, what's what? And in that conversation he said, wow, you have a story to tell. And I, I would really. He was writing blog posts and follow ups on everybody said, I want to, I want to do something bigger here, like give me a little bit. Came back a couple months later and said, vanity Fair wants to tell your story. Holy. So here we are. It's pretty mind blowing.

Pretty. Yeah. So. Well, so. So what did they identify? What did they find in you?

You know, I think that the way that I think Dave has described it in the past is that sort of Howard Zinn, the people's history. It's like the book Masters of Doom was about the two main designers of Doom and Quake, John and John. And I was an ancillary character in a lot of ways. Set dressing and the culture of gaming at that point was very different. There was a huge amount of sexism, not that there isn't today, which is kind of one of the themes, but it was very rare that there were any women around. I was one of the only women in the scene at that point. And really the story was about my experience through that time. So it was like retelling Masters of Doom in many ways, but through my eyes as somebody who was somewhat ancillary in the original story, but actually had a whole lot going on. And to go from that being this sort of set dressing extra character, the one token woman in the room back then to now. Having this very mainstream tech career running, you know, one of the fastest growing startups in, in, in the Silicon Valley. It's, that's the arc.

Well, there's something else there too, I think is that you've used the term set dressing a couple times. Have you ever heard of the book Fifth Business?

No.

Fifth Business is a book. Famous Canadian author, Robertson Davies, and the term fifth business is kind of like set dressing. You're kind of, you're kind of an insignificant character to the story. You, you kind of go through life and you end life and it doesn't really matter. But I don't see that at all as you being set dressing back then because I think in a way being one of the only women in tech and hosting some of these parties and being so early in, you were pretty much a trailblazer, like in a pretty big way. I think most of the guys that were there were set dressing because there were just a million of them. But it's like that was so early on that it was extraordinarily unique. Like, and I remember even the era, I don't know when the hell did I get my first email address? 97 probably. Like you were already.

Probably right. Yeah.

You know, yeah.

And we were already doing it at that point. And it is interesting because I think what it really, what it really boils down to is that at that time it was so rare that all people could see was that I was a woman and there was not a lot of deeper investigation into who I was as a human being or there was a lot of focus on John and John and like these gods of gaming and who they were and what they were about, but I was either viewed as the geeky gamer girl and that was it, or, or later on the, you know, much more glitzy video game Vixen, which was the latter day story, but it was very one dimensional. There was not really an appreciation for the fact that I was a whole human being and that I wasn't just there because of how I looked at the time, that I had my whole own arc and I was building something special. And I think that's over the course of the last 20 years, what's played out.

So we've had, I would guess about 30% of our guests on the Second Command podcast are women. 40% of the members of the CEO alliance are women. And I think if we think about who is the kind of most well known second in command probably in history, it's Sheryl Sandberg. We've, we've really broken through this, have we not? Or is it still. You mentioned that women in tech is still an issue. Is it still an issue or is it getting better?

It's absolutely still an issue. It is getting a bit better. I think that if you look deeply, gaming remains hugely problematic inside the culture. And unfortunately, I think things really have not changed inside gaming a lot. And gaming is big business. So easy to write that off as like, oh, it's just games, it's electronic entertainment, whatever. But it's actually a massive industry and women of my generation who have tried to stick in it have really struggled. And I think that's a, that's a big deal. And in mainstream tech, we really haven't gotten past it. I think that the good news is there are pockets where you can carve out a great career and you can experience less sexism, but it is not gone by any means. It is still very much a boys club in many ways. And I think I'm in a really unique situation because as a number two second in command, I'm second in command to a woman as well. We've got a really unique situation at Vanta. Were the only two C levels at the company. Christina, female founder, you know, just led $150 million Series B round from top tier VCs. It's a really unique story and situation.

Yep.

And I think both of us would love to be in a position where it was not notable that we are women. I think it's still very notable.

Yeah, I think we're moving more and more towards that. They asked Pierre Trudeau, the Canadian Prime Minister a few years ago, they said, you know, 50% of your cabinet is women. And he goes, well, it's, it's 2017. Like, can we move past this like it should? It shouldn't be a story. Right. I want to know about, I want to know about Vanta. I want to shift gears a little bit on this. But so what, what is Vanta do? What's the kind of core focus of the business? And then I want to talk through some of kind of what you've done to scale the company.

Yeah. So Vanta does automated compliance and our mission is to make more data on the Internet trustworthy, our customers, be trustworthy players in the market. And what we do at the most basic level is provide a platform that sets our customers and partners up to be able to prove their security posture, to automate their compliance efforts so they can show to their customers and the world that they can be trusted. And Christina really pioneered the market. You Know, back in the day, before the advent of Vanta, this was a very painful manual process. If a company wanted to get ready to go through the process of achieving SoC2 compliance, they would literally be working with the CPA auditor and taking screenshots inside their core systems and, you know, like, screen sharing to show who has access to things. It's just this wildly manual process to prove your systems are secure. And what she did is build technology in a process to automate a lot of that work. So not only are you showing that at a point in time you're secure, but that you are continuously proving that security posture and that you can be trusted to hold sensitive data. And, you know, things have only gotten wilder on that landscape. I think it's very hard to be a startup these days and think about securing customer data, and that's exactly what we help them do.

Okay, and you've been with the company for just under a year, correct?

Yeah, I'm just going on seven months.

Okay, and when did they complete the Series B? You said they just raised 150 million in series B?

Yep. So Christina closed the initial tranche of 110 million about three months ago and closed a $40 million extension about a week ago.

Okay, so how did that change? And what was. What had you raised as a company prior to that?

So prior to that, we had raised 50 million, and we're in a great cash position, but I think everybody sees the world changing, and Christina is extremely sharp and got a background in venture capital and saw the way that the world was shifting. And so we went out and landed some more cash and put us in a great position to be able to grow and build over the next few years.

I'll tell you, the world is changing rapid. I'm in Dubai right now. I spoke to an entrepreneur here the other day, and he said he has a friend in Saudi Arabia opening up a chain of pubs with like. I'm like, what? He's like, oh, no. They're going Western on everything because they know they can't rely on oil as their entire source of income. I'm like, when Saudi Arabia is opening up bars, like, with. With literally kegs. Yeah, yeah, the world's changing. Okay, so you'd raised 50, you've done another 110 with. With the second and 40 in the last three or four months. How does that change the organization? And how do you keep the blinders on and. And keep focused and not have that impact? You know, what are kind of the positive ripple effects and the negative ripple Effects of that kind of a raise.

Yeah, I think that there's always a temptation with a raise like that to go all out. And the, the honest answer is it doesn't change a lot. You know, Christina and part of what drew me to the organization, she's really got a very disciplined mindset. So we've got a very busy space. We've got 30 plus copycat competitors that have come on the market because Vanta had this huge rocket sh. Growth. We had all these copycat competitors come on the market to the point that if there was a typo on our website, there was a typo on their website because they copy pasted the text. That's how bad it's been. And so, you know, there's a temptation both with the macroeconomic climate and copycat competitors and the dynamics that are happening to shift. But the truth is our mission is to continue to do what we're doing. It's working. We are growing incredibly fast. And now this is about being able to make a couple of additional big bets, but really just grow the core, the fundamentals of the business and double down on what, what we know is good. You know, we'll move towards international markets, we'll move towards bigger customers, we'll make some, some big bets on the product side. But aside from that, it's really just keep on growing.

How do you keep your blinders on and keep focused when you have those competitors? How do you avoid, you know, getting distracted with them? Yeah, I guess. And at the same time, how do you keep your eye on them to see if they are doing something that you know is unique as well? Right. Like the, the Chinese kind of copied us in North America and then all of a sudden they can they kick our ass in a few areas too?

Yeah. It's really about deciding what's important. And it is a constant balance. You know, we do have to pay attention, but we've also had to get extremely disciplined in agreeing as a leadership team about what matters. And a lot of these copycat competitors have come with a lot of flash. So they're very marketing first. And the marketing has made it look from the outside that they are bigger than they actually are or they've got growth that isn't actually there. And it can be very tempting, particularly with a growing team to try to address that. They're also somewhat obsessed with us. They get out and first thing they do is talk about us and how they're different. And you know, we have really, as a leadership team, agreed that we are here to Run our own race. And that's a mantra we repeat frequently. We are running our own race. We are not reactive to the market, to any competitor. And we know what we're doing is working. And we also know what our growth looks like and we know what their growth looks like. So whatever it may look like on the shiny surface, continuing that focus on what we know matters and building our strategy around what we know to be true. I like that those have been the keys. And you know, Christina is, we're both Midwesterners. She's, she's from Ohio, I'm from Kansas. We, we've got Team Midwestern Assassins. We're, we're trying to stay extremely focused on that core and just executing on that machine and what we know works.

That even leads into my, my question I was going to ask you about what was it that you think she saw in you? Because you said, you mentioned to me earlier there's about 350 employees now at Vanta. How many approximately were there when you joined?

Probably like we've added about a hundred. So 250 or so.

Yeah. So 250 people. When you come in as the second in command, what did she see in you and what did you see in the company to come in. And then I've got a second layer of questions after that.

Yeah. So in terms of what I saw, that, that drew me in. I, I'm grateful to have run a process at that time when before the economy had shifted, I had great options and I looked at a lot of companies and there were really three things I was looking for. I was looking for a company with really obvious demonstrable product market fit. I was looking for a company that was ready for scale, where I could come play that scale playbook and really double down on growth. It's a playbook. I learned from an incredible mentor at Twilio who was the former COO of Salesforce. So I wanted to play that, that whole play. And then the third was I wanted an incredible leader. I wanted that top of the Christmas tree role to be somebody that I didn't just respect, but I really liked and felt had shared values and a shared approach to life. And I really found that at Vanta it was hitting all the metrics. Clear product market fit, killing it in the market. And Christina is a really thoughtful leader and I think what she saw in me was scrappiness, hustle, that Midwestern work ethic of not flashy and very focused on the core of what matters. And honestly, it's that the Gamer's heart. It's that like, let's get down to it and solve the problem. And she's a very smart, pragmatic person. And I think that we both, you know, we found that in each other that forget about the drama and forget about ego and flash and let's just execute. Let's just go crush it together.

Because when you've got 250 people and you're starting to really build out your first true leadership team, you know, you might have got a management team that have emerged into leadership roles, but now you're hiring these outside executives over top of a current group of people. That's a really big boulder to bring into a pond. Like you cause huge ripples. Right. Good and bad. Yeah, she must have. What did she see in you? Like, was it that scrappy work ethic, the values? Was it that she knew? Like, did she talk to you about that?

Yeah, I, I do think that that was, that was a big element of it, was that this whole. There's a very midwestern vibe in a lot of ways inside the company and that I think that our desire is to keep our head down and, and just execute. And she saw that in me. And there were also, she, she's very bright. She had a clear checklist. And there were elements of my experience that really resonated. So things like I had seen scale. So I had taken, you know, the team at Twilio from basically no sales team to a thousand person sales Org and I played a key role in that growth. I had endorsements from some mentors who clearly know their stuff and were able to articulate that they believed I could do the job. And I had done some key things. Like one of the things I did at Twilio was we started with a lot of inbound interest and way more than a sales team could handle. And over the course of a few years, I helped the organization transition to an almost entirely outbound motion. So like those fundamental elements of what it takes to scale a company, I had done them before. And I think that was really what she was seeking as somebody who had seen the scale and knew how to make the key transitions that build the machine under the business.

Okay, so then she's making the decision to hire you, you're joining the company and then, then you've got to walk into an organization where there's 250 people and there's got to be at least one who wanted your job.

Yes. Yeah. And it's a challenge.

How do you manage through that? How do you, what's your first 90 days like? How do you, how do you build that culture and the, the, the relationship with those people?

It was, that was one of the things I came in very mindful of in my run up to joining. I talked to other CROs and others who had come into similar positions. And one of the themes that came out of those conversations was that early days when they entered a company, many of them said the mistake they made first was not focusing enough on the people who are already there and sort of coming and thinking they're going to just start executing and doing the work rather than appreciating that there's a team that built the business to this point. So I came in with that mindset of people first. Let me really get a feel for who's who and what's what and also just be empathetic to that idea that nobody wants to get layered ever, anywhere. Nobody, nobody's ever happy to get layered. So really developing those relationships and understanding the people was my mission one. And then getting really honest with them about strengths and where I saw places for them in the business and what was working and what wasn't. But I had to put it first. It had to. It did mean that I started executing a little more slowly. So I picked a shorter list of things to focus on at the beginning so I can invest the time with those people.

How did you pick that, that shorter list? I was going to ask you about that. How did you pick the list of the, you know, the critical few projects to focus on?

Yeah, I mean my first 30 days I picked one thing and really it carried into 60 days and it was all about understanding the numbers behind the business and what was driving our biggest challenges. And at that point, the single biggest problem we had in the business was we did not have enough quota carrying capacity in the field. At this point in our evolution, we are a 100% direct sales organization. So every deal gets done by a human salesperson. There's no product led growth or anything else like that. So my number one thing, the one thing I did the first 30 to 60 days was bring in more salespeople, just literally get more bodies in the door so we can sell more. And I came to that by interviewing everybody on the leadership team, talking to the board, talking to folks that mattered and understanding that to hit our growth targets. If we didn't do that, it wouldn't happen. So that was mission one.

What kind of growth targets?

Significant. Very significant. You know, the mission, the mission is really, you know, continue to Double year over year over year. And you know, at least as a baseline and you know, Vanta had this incredible run of growth for very long. And so now it's about continuing that growth and even accelerating it and ensuring that we can continue to double that. But it's also about metrics that fall behind that, like efficiency. Can we get more productivity at a lower cost? Can we get more efficient? Can we reduce cogs? So I'm now beyond that. Like we've proven we have product market fit. We're now onto the second order goals of okay, how do we scale and do it in a way where we are hitting the key metrics that matter for a SaaS business of our size.

Yeah.

So got to do it smartly. It's not just growth at all costs. And that's true for everybody now with the climate shifting. Nobody's. Nobody should be in growth at all costs anymore.

Yeah. I think it's building better companies right now.

Yeah.

Are you, are you a hybrid organization? Are you all in office? Are you, where are you there?

We're remote first, so we are. Everybody on paper is a remote first employee. We do have offices, so we've got offices in San Francisco and New York. We've now just opened offices in Dublin and Sydney in the last 30 days, which I'm extremely excited about.

A terrible place to have to go visit.

I know, right? Yeah. The excuse is wonderful. But we're remote first company, which is, you know, given our target market, we're selling predominantly to SMBs today and we've got, you know, a team of more junior sellers. It's. It's a challenging environment to build in. So we're trying to get that balance right of how often we get people together. One of the first things we did after I joined was we had an all company retreat. We got everybody in the company together in person and we're trying to do that now more on a smaller scale regionally.

Were you, were you always an all remote company or was that something that happened with COVID It was.

There was more of a physical presence pre Covid, but the company was so much smaller then. So it was Covid that shifted it to a true remote first.

So in building a remote company, what are the things you have to do that are different in terms of building a strong company culture than when you're kind of in the physical space, in a physical office space?

You know, I think we're still learning and we're definitely post the world of COVID where it was like build culture by doing Zoom happy hours. You know, where we are light years beyond that now. And I think we're nobody's. Nobody's really got the answer to that question at this point is my honest assessment. I think the things that really matter are repetition. I think you have to repeat yourself a lot more. You have to invest the time to repeat what matters and the message not just in big team meetings and big group settings, but one on one. And you have to find some way to make a little space where people can be humans. I think especially with the junior team that the hardest thing is they just. Nobody's going to feel fulfilled just being on Zoom meetings all day. You've got to have that connective space in between where people get to know each other and whether that's getting them together in the physical world intermittently or creating a vibe on slack where people can be human and we celebrate each other. I think that's really the key. And I don't know that anybody has nailed that yet.

Yeah, we have heard of it.

Yeah, it's hard. It's hard to feel like a real human in a remote first world, I think.

Yeah, it's interesting in terms of hiring the, the sales people and CRO. Is CRO the head of sales or do you have marketing reporting into you? Do you have things other than sales reporting into as well or where. What's the typical title?

It varies. You know, CRO can really vary in what that means and sometimes CRO and COO can look very similar. In my world today I have sales which includes the core sales team and our sales development team, BDRs and all of that good stuff. I've got elements of operations and then I also have our onboarding and customer success team. So I have all the humans doing the work pre and post sale and that includes things like sales engineers and some subject matter experts and, and all of that. So that's my world today.

What do you think is some of the successes or some of the failures that, that we have between sales and operations? When I was building 1-800-got- junk, our franchise sales team said they would sign a franchise and they would throw it over the fence to operations. I'm like, whoa, we're not throwing a human over top of a fence to another human to catch anymore. We need to some better handoff. How do you make sure that like what have you done? Well, to make sure that sales and BDRs are handing over the new clients into the organization in the most successful way, like in communicating. It's not just filling out Fields in Salesforce, is it?

No. And that really has been a huge area of investment for us and one that we're continuing to double down on. I think that we started out with that idea as a team, like, okay, I've closed the deal, my work here is done and then we move to a. Well, there's got to be a better handoff. Fill out the fields in Salesforce with step two. Like at least we're sharing data now. But really that does not solve the problem. And at this point my honest assessment is, and this is, it comes back to the remote first culture. You've got to have those groups regularly talking to each other and regularly interacting in some kind of way that isn't just a handoff. They have to know each other, they have to understand each other's priorities and they have to work together as if they were one team. So one of the things I did early on seeing that division was we started building a mid market team which is as we move up market, which is dealing with bigger companies, I put the sales and the onboarding and CS folks into one team for mid market rather than having them be separate teams under one leader. And by doing that, it's like they suddenly have all this connective tissue and they're talking to each other and they've actually changed their emotions to reflect something that works better. So just like putting them together has been a big key and getting them talking about what matters.

I like that a lot. We've got our, our sales team now doing a video introduction to operations. So after they've signed the client, the salesperson actually needs to do a three minute loom video to hand over as well as fill out all the damn forms. But something's happening where they're doing a video and, and they don't get a commission until they send the video over to operations. So it's really forcing them. And then operations has to say, I know enough now about this client that I'm receiving them. But that doesn't scale. Like that's a small organization. I don't know how you do that with thousands of salespeople. Right.

But I think you nailed it with incentives though, because incentives matter too. You've got to keep folks on the hook for that correct behavior. And that's part of what makes it scale. You can talk about it all day, you can tell folks to do things, you can ask them to make the videos. But if you don't tie incentives to the behavior you need, it likely will not scale in a bigger org.

Yeah, it's something to think through it. So you mentioned selling into enterprise. I'd like to ask you a question about that. And then I've got two other kind of final questions to wrap up. But what do you think some of the successes are for companies? Selling into the, the larger corporations or selling into companies?

Oh, my gosh. Yeah. You know, I know this is probably like.

It's probably three books, right?

It is. And it's something I'm really passionate about. When I came into Twilio, we did not have an enterprise sales function in earnest. And I ended up in my first 12 months there doing 15 deals in the Fortune 500 at Twilio. And part of the battle was we were selling APIs. And enterprises are not used to buying APIs. It's just the style of technology, the way you have to contract it. It was very unfamiliar. And really, I think the heart of being successful at that is doing deep, deep discovery and understanding the problems that that enterprise is trying to solve. And you have to end up being a translator between the company trying to close the business and that enterprise. And there's no one right solution. But if you do great discovery, that that's going to get you closer to how you solve the problem for them. And if you can solve a real problem, they will help you get through the hoops of procurement and the mess it takes to do business with an enterprise.

It's really trying to understand them versus getting them to understand you.

Yeah, absolutely.

All right, how about you and your role? I mean, you know, you're, you're operating as a CRO, you're operating as a second command. You've got huge, huge numbers of people in growth. Where are you still growing your skills?

Everywhere. That's a long list. You know, I don't know. I'm a lifelong learner. I'm always, I want to always be challenged and pushing. And I think that there are a number of areas for me right now I'd say my top three demand and marketing is a subject matter area that I'm really deeply trying to learn right now. Key to scaling our business. And I don't own the function, but I play a critical role in setting the strategy. So that's my subject matter area that I am learning in terms of skill. You know, communication is probably the skill I'm most focused on now. I've got this very diverse org of folks from my leadership team and that's really my team at the end of the day, leaders at all levels and different functions, all of whom are new to me, I've got everything from very experienced VPs under me down to junior level sellers in their first closing role. Trying to get the style and the cadence of communication right is the single most important skill I'm hoping to nail in the next year. And it's tough. It's tough.

Yeah, it's, it's, it's tough when as you put it, you've got different, different styles of people, different levels of people. Then you're also dealing with the remote org, so you're not all in the same office. And are you dealing with multiple countries now as well? Well, you mentioned Australia and are you dealing with multiple languages as well? You probably are, right?

Not yet. Not yet. We're super close. We're on the edge of that right now. Everybody's, everybody's English speaking so that, that does make it a bit easier, but it's, it's only getting more complicated from here.

Yeah. Gets real real when all of a sudden you got esl. Because there's a, there's a, a sentence that I use all the time. It's a six word sentence. It's. Have you ever seen the word? The R? The phrase. I didn't say you were beautiful. And if you read that, you read that sentence and you put the emphasis on each of the six words, it means six different things. Like I didn't say you were beautiful. I didn't say you're beautiful. I didn't say you were. That like English is hard enough with English people. Then you add other language and then the fact that we're going so quickly. Yeah, all bets are off. Yeah, I piss off people with six word emails all the time and I'm just saying happy birthday to them. It's crazy, right?

All right.

I want to go Back to the 21, 22 year old Stevie Case. You're, you've already dropped out of school. But what would you tell yourself you're just starting your career. What advice would you give yourself that you know to be true today but you wish you'd known back then? I think I know what this might be.

I think the, the biggest thing I would impart on myself at that age is that there are no real limits in life. The, the limits are all perceived. They are all self inflicted based on perception. And these limitations that you grow up with in childhood, these ideas of who you are and what it takes to be successful, these are all fake. Like you, you can do anything. There are no doors that are truly closed. And once you give yourself that permission and stop being so afraid, all bets are off and, and you can really just go anywhere and do anything. And I think what coming to that realization, I wish I had come to that realization a lot earlier in life because you mentioned.

This is beautiful. You mentioned that you were kind of an insecure kid back then. Is that the being afraid, the insecurity, is that the tie in?

Absolutely, yeah. I mean, I was so shy and so unsure and I thought that there were just all of these things and structures in the world that I didn't have access to or didn't understand and I didn't have the magic code. And other people must know a lot more than me. And you know, the deeper I get into my career, the more I realize we're all just making this up as we go. We're all just learning.

Yeah.

Nobody's got the magic code. And sure, people know certain, certain things better than others, but it's all learnable.

Yeah. Okay, I want one more then. What advice would you give the insecure kids or, or youth that are 20, 21, 22 or even, you know, they're in their mid-20s, early-30s, that have still got that insecurity? How do you beat that? What do you do to beat that or to get better at it?

You just get. It's. Practice is, is the honest answer. It's, it's years of picking a mantra and I, I met somebody early in career who said something that really stuck with me, which was he, he looked at the landscape of, of the industry, in the world and what he wanted to do, and he thought, why not me? Why not me? And years of repeating that to yourself, why not me? Why can't that person be me? Why can't I be in that role? That practice over and over leads to actually believing it. It takes time, does not come naturally. You have to repeat it. And, and the more you repeat that to yourself, the more you realize, yeah, why not?

I love that. I've always felt like we're all 16 year olds trapped in adult bodies. And when you realize everybody else is a 16 year old trapped in an adult body, it just got easier, right?

A hundred percent. We're all on an even playing field. Everybody has the same feelings inside. You just gotta go for it. Stop asking for permission and, and just give that permission to yourself.

Well, I'll tell you, Christina made a huge hire, great hire in bringing you in as a CRO. Stevie Case CRO and Second Command for Vanta. Thank you so much for sharing with us on the Second Command podcast.

My pleasure. Thanks for having me. You're balancing centralization and decentralization. You're balancing the need to standardize specific processes and policies so that you can scale. And there is an amount of diversity that you want to retain because it's what gives the organization its lifeblood.