Ep. 237 – Vanta CRO, Stevie Case

Our guest 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 their first account executives, 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 to grow the sales team from a dozen to over 1,000 team members. Stevie also supports startups, serving as an angel investor and advisor for the past decade. 

In This Conversation We Discuss:

  • What gaming was like in the 90s and Stevie’s past career as a professional gamer
  • The effects of sexism in the workplace 
  • How to avoid getting distracted by competitors while avoiding copycats
  • How to build a culture with a remote company 


Vanta – https://www.vanta.com

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Our guest for this episode 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 several years of sales and business development experience to the new role and served as Vice President of Mid-Market Sales at Twilio, a market-leading cloud communications platform.

Joining as one of their first account executives, 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 to grow the sales team from 12 to over 1,000 team members. Stevie also supports startups, serving as an Angel investor and advisor for the past several years. Stevie, welcome to the show. 

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

Selfishly, I want to dive in about all this Angel investing and I’d love to hear some of your advice. Walk me through a little bit about how you got into the role that you’re in. What got you in your career to being a CRO and being the second command of Vanta? 

I had a very non-traditional path to the role is the honest answer. It started at the University of Kansas thinking I was going to be a lawyer. I was going down a pre-law path and ended up dropping out of school and starting my career as a professional video gamer. That is the thing that indirectly led me into tech. I played video games professionally. I ended up making video games for a living and then ended up sidestepping into mainstream tech.

I was working at Warner Brothers producing mobile video games. I had a vendor who approached me and said, “I need a junior salesperson. I could teach you to sell. What do you think?” The truth was I thought it sounded uncomfortable and I had no idea what sales were. I’ve always been about a challenge so I took that role and I’ve been in sales ever since.

I worked my way up and had experience at small companies and big companies. Twilio was the place that taught me how to scale. I went from being an individual contributor to running a $400 million business there and growing a huge team. When the opportunity came to come over and play that scale playbook at a growing startup at Vanta, I jumped on it.

Walk me through the logic or the mindset 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? You said junior sales role. 

The honest answer is I didn’t know what sales was. I had an interesting path through gaming. I had a story about my background in gaming come out in Vanity Fair. It’s all I knew. I’m a kid from Kansas. I dropped out of college. I had no sense of the world and no passport. I was not worldly and had not seen a lot so I didn’t have an idea of what sales was. It seemed like a good challenge. It sounded unfamiliar. I didn’t know what it was or what it meant. It was something I wanted to learn about. I was a shy kid. It felt like a big challenge. I love a challenge and it felt like something I could learn.

Tell me about gaming. My kids are going to lose their cool when they found out I’m talking to a former professional gamer. How old were you when you were doing that? What was that like? What was it then? We’ve had some exposure to it in the last several years. 

It’s radically different now than it was then. We’re talking about the late ’90s. I went off to the University of Kansas when I was seventeen. It was Quake and Doom. It’s the early days of first-person shooters and the internet. With Quake coming out, it was one of the first games that you could play competitively online. We were going into a console inside the game and typing the IP address as servers to connect with very basic text chat but it was multiplayer. IRC was a thing. This was the very beginning of the social aspects of the internet. I formed a lot of friendships and I ended up joining a team.

Back in these days what it looked like was typically LAN parties but still some play online. I lived in this house with a bunch of friends in college. We’d have people drive from all over the country and bring their 21-inch CRT monitors, sit in a room and play Quake together on LAN. That’s what it looked like back then and I got sponsorships from joystick companies. I joined the very first league and was paid full-time to play the game competitively.

Knowing what the space is now, is there something pulling on your heartstrings to go back into that industry at all? 

No. I will always be a gamer at heart. The industry itself 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 a grownup and as a grownup adult woman, mainstream tech has been much more open to me than gaming. As much as I love gaming, it is a hobby as opposed to a profession.

You haven’t ruined your hobby, which is cool too. I remember my kids trying to explain that gaming was a thing and they were professionals. I thought they were lying to me. I’m like, “You guys are idiots. You’re 10 and 8. That’s funny.” I then started hearing about it. It’s a big deal.

You can make a huge amount of money. 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 the Olympics. That was the vision.

You talked about it too? 

Yes. That was what we all believed would come to fruition and work there in a lot of ways. There are people making hundreds of thousands, in some cases even millions of dollars as pro gamers. It’s a real profession for folks and people do show up to Staples Center in LA and watch professional video gamers battle it out.

I spoke to the CEO of a professional gaming company in California. It’s a multimillion-dollar business and he’s not even a gamer. He just owns teams. They have houses and trainers.

It is a thing. There are gaming houses out there. There are aspects of it that look a lot like real professional athletics and it requires twitch reflexes. You do have to practice. This is eight hours a day. It’s a full-time job. You also age your hell because your twitch reflexes fade at a certain age. In that mid to early twenties, they fade and you cannot be competitive anymore. Bad eyesight is another one.

You got into a junior sales role which brings you into the business world a little bit. Is there anything that you’ve pulled from sales that you still carry with you in your career? 

It’s the same thread I pulled from gaming, truthfully. When it comes down to it, whether it’s sales, being a CRO or being a gamer, it’s all about resource management, numbers and understanding the levers you can pull to get outcomes. It does boil down to building that strategy and understanding how to influence people. A game is a very one-person endeavor and you’re driving those outcomes yourselves and making strategic decisions. When you get into sales, it becomes a two-player. You have to start to think about the person you’re trying to do business with, what matters to them and how you create outcomes for them and your company.

CRO takes that to a next level of thinking about dozens or hundreds of people like how you manage those resources in a way to create a certain outcome. It all comes down to the same steps. It’s 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.

I’m going to ask you about Vanity Fair because you were covering Vanity Fair about gaming. What were they writing about? How did they learn about you? 

There was a book that came out in the early 2000s called Masters of Doom. The author is this wonderful guy Dave Kushner, who wrote about those early days of first-person shooters, Doom and Quake. I spent time with Dave way back, both in the writing of that book and even before. He came to cover that LAN party gaming culture in 1996 when I lived in Kansas. That was the first time I met him.

SIC 237 | Remote Company

Masters of Doom: How Two Guys Created an Empire and Transformed Pop Culture

He was doing a follow-up on everybody who was in Masters of Doom. He called me up and it was a check-in like, “What’s what?” In that conversation, he said, “You have a story to tell.” He was writing blog posts and follow-ups on everybody. He said, “I want to do something bigger here. Give me a little bit.” He came back a couple of months later and said, “Vanity Fair wants to tell your story.” Here we are. It’s pretty mind-blowing.

What did they identify? What did they find in you? 

The way that Dave has described it in the past is like Howard’s in A People’s History. The book Masters of Doom was about the two main designers of Doom and Quake, John and John. I was an ancillary character and a lot of ways set dressing. The culture of gaming at that point was very different. There was a huge amount of sexism, not that there isn’t now, which is one of the themes. It was very rare that there were any women around. I was one of the only women in the scene, at that point.

The story was about my experience through that time. It was retelling Masters of Doom in many ways but through my eyes as somebody who was somewhat ancillary in the original story but had a whole lot going on. To go from this set-dressing extra character, the one token woman in the room back then to having this very mainstream tech career running in one of the fastest-growing startups in Silicon Valley is the arc.

There’s something else there too. You’ve used the term set dressing a couple of times. Have you ever heard of the book Fifth Business


Fifth Business is a book by a famous Canadian author, Robertson Davies. The term Fifth Business is like set dressing. You’re an insignificant character in the story. You’re going through life and end life and it doesn’t matter but I don’t see that at all as you being set dressing back then. 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 in a pretty big way. Most of the guys that were there were set dressing because there were a million of them. That was so early on that it was extraordinarily unique. I even remember the era when I got my first email address. That was in ’97 probably. 

That’s probably right. We were already doing it at that point. It is interesting because what it boils down to is that at that time, it was so rare that all people could see was that I was a woman. There was not a lot of deeper investigation into who I was as a human being. There was a lot of focus on John and John and these gods of gaming, who they were and what they were about but I was either viewed as the geeky gamer girl and that was it or later on, the much more glitzy video game vixen, which was the latter day story but it was very one dimensional. There was no 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. I had my whole arc and I was building something special. For several years, that’s what’s played out.

About 30% of our guests on the show are women and 40% of the members of the COO Alliance are women. If we think about who is the most well-known second in command probably in history, it’s Sheryl Sandberg. We’ve broken through this, have we not? You mentioned that women in tech are still an issue. Is it still an issue or is it getting better? 

It’s still an issue. It is getting a bit better. If you look deeply, gaming remains hugely problematic inside the culture. Unfortunately, things have not changed inside gaming a lot. Gaming is big business. It’s so easy to write that off like, “It’s just games. It’s electronic entertainment,” but it’s a massive industry. Women of my generation who have tried to stick in it have struggled. That’s a big deal.

In mainstream tech, we haven’t gotten past it. The good news is there are pockets where you can carve out a great career and experience less sexism but it is not gone by any means. It is still very much a boys’ club in many ways. I’m in a unique situation because I’m a second in command to a woman as well. We’ve got a unique situation at Vanta. We’re the only two C-levels at the company. Christina, our female Founder, led a $150 million series B-round from top-tier VCs. It’s a unique story and situation. Both of us would love to be in a position where it was not notable that we are women but it’s still very notable.

We’re moving more towards that. They asked Pierre Trudeau, the Canadian Prime Minister a few years ago, “Fifty percent of your cabinet is women.” He goes, “It’s 2017. Can we move past this? It shouldn’t be a story.” I want to know about Vanta. What does Vanta do? What’s the core focus of the business? I then want to talk through some of what you’ve done to scale the company. 

Vanta does automated compliance. Our mission is to make more data on the internet trustworthy. We help our customers be trustworthy players in the market. 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 and automate their compliance efforts so they can show their customers and the world that they can be trusted.

Christina pioneered the market. 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 SOC 2 compliance, they would be working with a CPA auditor and taking screenshots inside their core systems and screen-sharing to show who has access to things. It’s this wildly manual process to prove your systems are secure.

What she did is build technology in a process to automate a lot of that work. Not only are you showing that at a point in time, you’re secure but you are continuously proving that security posture and that you can be trusted to hold sensitive data. Things have only gotten wilder on that landscape. It’s very hard to be a startup and think about securing customer data. That’s exactly what we help them do.

SIC 237 | Remote Company

Remote Company: Vanta helps people secure their sensitive data, especially to those who don’t know how to do it or are managing start-up businesses in need of proper initial support.


When did they complete series B? They raised $150 million in series B. 

Christina closed the initial tranche of $110 million and closed a $40 million extension.

What had you raised as a company prior to that? 

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

The world is changing rapidly. I’m in Dubai. I spoke to an entrepreneur here and he said he has a friend in Saudi Arabia opening up a chain of pubs. He’s like, “They’re going Western on everything because they know they can’t rely on oil as their entire source of income.” I’m like, “Saudi Arabia is opening up bars with literal kegs. The world’s changing.” You’d raised $50 million and done another $110 million and $40 million. How does that change the organization? How do you keep the blinders on, keep focused and not have that impact you? What are the positive and negative ripple effects of that raise? 

There’s always a temptation with a raise like that to go all out. The honest answer is it doesn’t change a lot. Part of what drew me to the organization is that Christina got a very disciplined mindset. 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 ship growth. 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.

There’s a temptation both with the macroeconomic climate, 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. This is about being able to make a couple of additional big bets but grow the core of the fundamentals of the business and double down on what we know is good. We’ll move towards international markets and bigger customers. We’ll make some big bets on the product side but aside from that, it keeps on growing.

How do you keep your blinders on and focused when you have those competitors? How do you avoid getting distracted by them? At the same time, how do you keep your eye on them to see if they are doing something unique as well? The Chinese copied us in North America and then all of a sudden, they can kick our ass in a few areas too. 

It’s about deciding what’s important. It is a constant balance. We do have to pay attention but we’ve also had to get extremely disciplined in agreeing as a leadership team about what matters. A lot of these copycat competitors have come with a lot of flash. They’re very marketing first. The marketing has made it look from the outside that they are bigger than they are or got growth that isn’t there. 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 the first thing they do is talk about us and how they’re different.

As a leadership team agreed that we are here to run our race. That’s a mantra we repeat frequently. We are not reactive to the market or any competitor. We know what we’re doing is working. We also know what our growth and their growth look like. Whatever it may look like on the shiny surface, we’re continuing that focus on what we know matters and building our strategy around what we know to be true. Those have been the keys. Christina and I are both Midwesterners. She’s from Ohio and I’m from Kansas. We’ve got team Midwestern assassins. We’re trying to stay extremely focused on that core and executing on that machine and what we know works.

What was it that you think she saw in you? There are about 350 employees at Vanta. How many approximately were there when you joined? 

We’ve added 100 so 250 or so.

There are 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?

In terms of what I saw that drew me in, I am grateful to have run a process at that time before the economy had shifted and had great options. I looked at a lot of companies and there were three things I was looking for. I was looking for a company with an 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 double down on growth. It’s a playbook I learned from an incredible mentor at Twilio, who was the former COO of Salesforce. I wanted to play that whole play.

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 liked and had shared values and approach to life. I found that at Vanta. It was hitting all the metrics, clear product market fit, killing it in the market and Christina is a thoughtful leader. What she saw in me was scrappiness, hustle and that Midwestern work ethic of not flashy and very focused on the core of what matters. Honestly, it’s that gamer’s heart of, “Let’s get down to it and solve the problem” She’s a very smart and pragmatic person. We found that in each other like, “Forget about the drama, ego and flash. Let’s execute and go crush it together.”

When you’ve got 250 people and starting to build your first true leadership team, you got a management team that has emerged into leadership roles but you’re hiring these outside executives over top of a current group of people, which is a big boulder to bring into a pond. You caused huge ripples, good and bad. What did she see in you? Was it that scrappy work ethic or the values? Did she talk to you about that?

Yes. The big element of it was there’s a very Midwestern vibe in a lot of ways inside the company. Our desire is to keep her head down and execute. She saw that in me. She’s very bright. She had a clear checklist and there were elements of my experience that resonated so things like I had seen scale. I had taken the team at Twilio from no sales team to a 1,000-person sales org and I played a key role in that growth. I had endorsements from some mentors who know their stuff and were able to articulate that they believed I could do the job. I had done some key things.

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. Over the course of a few years, I helped the organization transition to an almost entirely outbound motion. Those fundamental elements of what it takes to scale a company, I had done them before. That was what she was thinking as somebody who had seen the scale and knew how to make the key transitions that build the machine under the business.

She then made the decision to hire you and you’re joining the company. You’ve got to walk into an organization where there are 250 people and there’s got to be at least 1 who wanted your job. 

Yes. It’s a challenge.

How do you manage through that? What are your first 90 days like? How do you build that culture and relationship with those people? 

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. 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 were already there. They’re coming and thinking they’re going to start executing and doing the work rather than appreciating that there’s a team that built the business to this point.

I came in with that mindset of people first like, “Let me get a feel for who’s who and what’s what,” and also be empathetic to that idea that nobody wants to get layered ever anywhere. Nobody’s ever happy to get layered. Developing those relationships and understanding the people with my mission. Getting honest with them about strength 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 did mean that I started executing a little more slowly. I picked a shorter list of things to focus on at the beginning so I can invest time with those people.

How did you pick that shorter list or the list of critical few projects to focus on? 

In my first 30 days, I picked one thing and it carried into 60 days. It was all about understanding the numbers behind the business and what was driving our biggest challenges. 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 of our evolution, we are a 100% direct sales organization. Every deal gets done by a human salesperson. There’s no product-led growth or anything else like that.

The one thing I did during the first 30 to 60 days was to bring in more salespeople. I get more bodies in the door so we can sell more. 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 have done that, it wouldn’t happen. That was mission one.

What kind of growth targets? 

They’re very significant. The mission is to continue to double year over year, at least as a baseline. Vanta had this incredible run of growth for a very long. 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?” I’m beyond that.

We’ve proven we have product market fit. We’re onto the second-order goals of how we scale and do it in a way where we are hitting the key metrics that matter for a SaaS business of our size. We got to do it smartly. It’s not growth at all costs. That’s true for everybody. With the climate shifting, nobody should be in growth at all costs anymore.

It’s building better companies. Are you a hybrid organization? Are you all in the office? Where are you there? 

We’re remote first. Everybody on paper is a remote-first employee. We do have offices. We’ve got offices in San Francisco and New York. We’ve opened offices in Dublin and Sydney, which I’m extremely excited about. We’re a remote-first company. Given our target market, we’re selling predominantly to SMBs and we’ve got a team of more junior sellers. It’s a challenging environment to build in. We’re trying to get that balance right regarding 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. We’re trying to do that more on a smaller scale or regionally.

Were you always an all-remote company or was that something that happened with COVID? 

There was more of a physical presence pre-COVID but the company was so much smaller then. It was COVID that shifted it to a true remote first.

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

We’re still learning and we’re post the world of COVID where it was like building a culture by doing Zoom happy hours. We are light years beyond that. Nobody got the answer to that question at this point, is my honest assessment. The things that matter are repetition. 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.

You have to find some way to make a little space where people can be humans, especially with the junior team. The hardest thing is nobody’s going to feel fulfilled being in Zoom meetings all day. You’ve got to have that connective space in between where people get to know each other. Whether that’s getting them together in the physical world intermittently or creating a vibe on Slack where people can be human and celebrate each other is the key. I don’t know if anybody has nailed that yet.

SIC 237 | Remote Company

Remote Company: In a remote workplace, repeat yourself a lot to emphasize the importance of your message. There must also be some space where people can be humans.


We haven’t cracked the code. 

It’s hard to feel like a real human in a remote-first world.

Is CRO the head of sales or do you have marketing reporting to you? Do you have things other than sales reporting to you as well? What’s the typical CRO title? 

CRO can vary in what that means. Sometimes CRO and COO can look very similar. In my world, I have sales, which includes the core sales team, 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. I have all the humans doing the work pre and post-sale. That includes things like sales engineers, some subject matter experts and all of that.

When I was building 1-800-GOT-JUNK?, our franchise sales team said they would sign a franchise and throw it over the fence to operations. I’m like, “We’re not throwing a human over top of offense to another human to catch. We need some better handoff.” 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? It’s not just filling out fields in the salesforce, is it? 

No. That has been a huge area of investment for us and one that we’re continuing to double down. We started with that idea as a team. It’s like, “I’ve closed the deal. My work here is done.” We move to like, “There’s got to be a better handoff.” Filling out the fields in the salesforce is step two. At least, we’re sharing data but that does not solve the problem. At this point, my honest assessment and this comes back to the remote first culture is you’ve got to have those groups regularly talking to each other and interacting in some way that isn’t a handoff. They have to know and understand each other’s priorities. They have to work together as if they were one team.

One of the things I did early on seeing that division was we started building a mid-market team. As we move up in the market, which is dealing with bigger companies, I put the sales, onboarding and CS folks into one team for mid-market rather than having them be separate teams under one leader. By doing that, they suddenly have all this connective tissue and they’re talking to each other. They’ve changed their motions to reflect something that works better. Putting them together has been a big key in getting them to talk about what matters.

We’ve got our sales team doing a video introduction to operations. After they’ve signed the client, the salesperson needs to do a three-minute Loom video to hand over, as well as fill out all the forms but something’s happening where they’re doing a video. They don’t get a commission until they send the video over to operations. Operations have to say, “I know enough about this client that I’m receiving them,” but that doesn’t scale. That’s a small organization. I don’t know how you do that with thousands of salespeople. 

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

You mentioned selling into the enterprise. What do you think some of the successes are for companies selling into larger corporations or companies? It’s probably three books, right?

It is and it’s something I’m passionate about. When I came to Twilio, we did not have an enterprise sales function in earnest. In my first 12 months there, I ended up doing 15 deals in the Fortune 500. Part of the battle was we were selling APIs and enterprises are not used to buying APIs. The style of technology and the way you have to contract it were very unfamiliar.

The heart of being successful at that is doing deep discovery and understanding the problems that the enterprise is trying to solve. You have to end up being a translator between the company trying to close the business and that enterprise. There’s no one right solution but if you do great discoveries, that’s going to get you closer to how you solve the problem for them. 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.

SIC 237 | Remote Company

Remote Company: The heart of being successful is understanding the problems your team is trying to solve. If you can achieve a great discovery, it will bring you closer to finding the right solutions.


It’s trying to understand them versus getting them to understand you. How about you and your role? You’re operating as a CRO or as a second in command. You’ve got huge numbers of people and growth. Where are you still growing your skills? 

Everywhere. That’s a long list. I’m a lifelong learner. I want to always be challenged and pushed. There are a number of areas. Demand and marketing are subject matter areas that I’m deeply trying to learn. It’s key to scaling our business. I don’t own the function but I play a critical role in setting the strategy. That’s the subject matter area that I am learning.

In terms of skill, communication is probably the skill I’m most focused on. I’ve got this very diverse org of folks from my leadership team which is my team at the end of the day. They’re leaders at all levels with 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 roles. 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 years and it’s tough.

It’s tough when, as you put it, you’ve got different styles and levels of people. You’re then also dealing with the remote org so you’re not all in the same office. Are you dealing with multiple countries as well? 


You mentioned Australia. Are you dealing with multiple languages as well? 

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

Things get real when all of a sudden, you got ESL. There’s a six-word sentence that I use all the time. Have you ever seen the phrase, “I didn’t say you were beautiful?” If you read that sentence and put the emphasis on each of the 6 words, it means 6 different things. English is hard enough with English people and then the fact that we’re going so quickly. All bets are off. I piss off people with six-word emails all the time. I’m just saying, “Happy birthday to them.” It’s crazy. I want to go back to the 21 or 22-year-old Stevie Case. You’ve already dropped out of school but what would you tell yourself when starting your career? What advice would you give yourself that you know to be true now but you wish you’d known back then? 

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

You were an insecure kid back then. Is being afraid the insecurity? Is that the tie-in? 

Yes. I was so shy and unsure. I thought that there were all of these things and structures in the world that I didn’t have access to, didn’t understand and didn’t have the magic code and that other people must know a lot more than me. The deeper I get into my career, the more I realized, “We’re all making this up as we go. We’re all learning. Nobody’s got the magic code.” People know certain things better than others but it’s all learnable.

What advice would you give the insecure kids or youth that are 20, 21, 22, even in their mid-20s or early 30s that still got that insecurity? How do you beat that? What do you do to beat that or get better at it? 

Practice is the honest answer. It’s years of picking a mantra. I met somebody early in my career who said something that stuck with me, which was he looked at the landscape of the industry and the world and what he wanted to do. He thought, “Why not me?” Years of repeating to yourself, “Why not me? Why can’t that person be me? Why can’t I be in that role,” that practice leads to believing it. It takes time and it does not come naturally. You have to repeat it. The more you repeat that to yourself, the more you realize, “Why not.”

I’ve always felt like we’re all sixteen-year-olds trapped in adult bodies. When you realize everybody else is a sixteen-year-old trapped in an adult body, it got easier. 

We’re all on an even playing field. Everybody has the same feelings inside. You got to go for it. Stop asking for permission and give that permission to yourself.

Christina made a huge and great hire in bringing you in as a CRO. Stevie Case, CRO and second in command for Vanta, thank you so much for sharing with us on the show. 

It’s my pleasure. Thanks for having me.


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