Stevie Case, CRO, Vanta
If you can come up with something that's a win in a different way. It gives you something, it gives you a story. And you know, as a sales leader, that's what I'm looking for. So if I'm looking for people across the org, I understand that performance varies and there are factors and those factors are very real. But when I'm looking at my team, I look for people that are telling me, I understand I didn't make my number. But here's what I did about it. I went out and I sent 100 emails a day and I generated this much pipeline and I figured out a new play. I did this and I know it hasn't paid off yet, but I'm gonna keep hustling until it does. Those people I will always keep.
Pouyan Salehi, CEO & Co-Founder, Scratchpad
Is that who you would put in an A Player category then?
Stevie
Yeah. An A Player is not necessarily about outcomes. There are a lot of people in the world that have had incredible outcomes that are not A Players.
Pouyan
Well we're back. I'm Pouyan Salehi from Scratchpad. We got Corp here with me as well. We have a very special Beyond Quota guest today. Professional gaming icon known as kill Creek, video game inventor, a top performing sales legend and now CRO at Vanta, a company I've been a big fan of, but more importantly, pulling it off as a badass single mom. So Stevie, welcome. We're excited to have you. And let's jump in.
Ross Pomerantz, Comedian/Mogul
We can start with something light, like how much is like Vanta reducing headcount? I'm kidding. kidding, I'm kidding!
Stevie
That macro economic climate, it's fantastic out there.
Ross
That macro econ is killing us. Actually killing us.
Pouyan
Let's stay there for a minute, because I think there are a lot of folks that are finding themselves in the unfortunate situation of having been laid off, the company's not doing well, Stevie, you've been around the block. I mean, you've seen a lot. What advice would you have for folks there?
Stevie
You know, this is a moment to be thoughtful and to be measured. And I am really just grateful to be working with a team that is thinking through that strategy thinking through responsible growth. But I think the advice is, keep your head down, keep working. Like the reality out there is there is massive market opportunity, regardless of the macro economic climate. There are people that are killing it. We've got folks that are crushing quota, even given current macroeconomic climate so I think it's all about keeping your head down. Keep hustling, don't let it be an excuse. Just keep pushing.
Ross
As a CRO, what are those conversations like at the top? When you look at a macroeconomic situation like the one that we're in?
Stevie
You know, the conversation is extensive. It is, first of all, what do we expect to happen in the world? And the honest answer is nobody knows. But a lot of my work over the last six months has been talking to peers, is talking to CRO, CEOs, CFOs at other companies, and asking what are you seeing? What are you modeling? What are you expecting? Making sure we are aligned with what others are seeing in the market?
And then question number two is strategically, where do we go from here? How does that does that strategy that we defined earlier in the year still match the economic climate? And I think there's a real mentality shift that has to happen. It's the shift we're challenging ourselves to, and I think a lot of boards are having this conversation with their companies like, where do you get efficiency? How do you think about your strategy going forward in a world where the climate is going to be tougher and people are thinking about how to save money.
For us, one of the things we're really focused on right now is the shift up market. It's an important strategic shift for us, we've seen some great traction in the mid market and the enterprise. And we're doubling down there because in tougher climates, those are companies that are stable. They still need to save money, you know, they still need to address compliance, these are all great things that matter to them. So I think it's about connecting your strategy to efficiency metrics, as opposed to just growth metrics. And you got to change the whole way you're thinking about your business. It can't be growth at all costs anymore. You really got to think about how the math works on the back end of that equation.
Pouyan
What keeps you up at night? What are you worried about? As as CRO of a fast growing company?
Stevie
You know, the biggest thing that keeps me up at night is how do I see the future? How do I see it accurately enough to make good decisions today. You've got to look so many more steps ahead than in just like a sales leadership role. And I am so grateful to have had the journey I had at Twilio. You know, in my career, I've gone back and forth between being an IC salesperson carrying a quota, carrying a bag, being a sales leader, and now first time as a CRO. And a lot of the difference at each of those levels is how far ahead you have to look.
So in the CRO seat, I need to be looking 12-24 months out, five years out. Where are we trying to head as a company? And there's always this temptation to go back to that salespersons mindset of well, let's just win today. Let's beat today's number, this quarter's number and as long as we're doing that we're good. The thing that keeps me up is are we going to make next year's number? And are we going to hit our strategy three years out, five years out?
Pouyan
What else? Like I'm curious, what's it been like? In the CRO seat for the first time? What else are you learning?
Stevie
I think the biggest difference between being a sales leader and being a CRO is the metrics you look at. And the way you think about the math of the business, you need that math to work in a very different way. So it's not just about growth and quota, and net new revenue, you've got to have a much broader view. And the thing that becomes really important is understanding other benchmarks in the industry. How do you stack up against other companies at this stage at this point in their growth? So you know, it honestly goes back to a lot of my gamer past starting out as a gamer. It's really resource management. It's making sure you're aligning things. So when you get to the end of the game, you're actually set up to win.
Pouyan
I want to jump into gaming. But I want to hear real quick, you mentioned other metrics, like what other metrics?
Stevie
There's the obvious top line metrics, right. So we're, of course, thinking about all of the basics of net new revenue, expansion, churn, you know for us, it's been a transition from thinking about gross retention to thinking about net retention.
So we're making a shift right now to have much more emphasis there as we become a multi product company. Now I'm looking at the next level down, particularly in the current macro economic climate, I'm looking at sales efficiency, I am looking at how much I can get out of each individual person on the team, what size book of business can a CSM manage? And then we're starting to look at that in the context of bigger numbers for the the business.
Pouyan
You brought up the gaming. Let's go there because my understanding is you were studying to be a lawyer... And somehow you dropped out to play video games.
Stevie
I started playing when I was living in the dorms, I was on this honors floor of a dorm at the University of Kansas, Kansas girl. And we started playing Doom and then quake came out. And when quake came out, a lot of that cohort, they all moved into this house. And we were just having land parties in that house constantly. So it was 24/7 land parties and we even had friends traveling from all over the US. You know, there's no social media yet. So we're literally communicating with these folks on IRC. This is like ICQ, IRC early days of the internet, and they travel on out to our house then bring their 21 inch CRT monitors that weighed like 1000 pounds and like hook up some ethernet cables. But that that is why I am here. That early experience, like I learned to build a PC, bit by bit in that house. Like I learned the basics of how software gets made in that house. It radically changed my life. And I'm such a believer in gaming for that reason.
Ross
God same. Built this guy right here to my right. I'm all about it. I want to hear the origin of your gamertag
Stevie
Oh, yes.
Ross
Tell that story.
Stevie
So KillCreek. In the early days, I had no idea I was going to be stuck with this name for my whole life basically, but so -
Ross Pomerantz
Could've been way worse and way less badass. Like when I think about the names that I've come up with on these games... Yeah.
Stevie
I wanted something that sounds dangerous. Yeah, so KillCreek is actually a real creek that I grew up near. And it was also my favorite band in college. And the funny thing was, I ended up being friends with the band. Great guys and I ended up being lifelong friends with the lead singer. And he always thought it was rather hilarious that they had made a real go at being a big famous band signed to a label, and that I was featured in Rolling Stone before there was. This does not seem right. This is not how it was supposed to go.
Ross
You would have gotten the verified checkmark on social media and they wouldn't have.
Stevie
Yes, and I would have felt really bad about it.
Ross
So have you've watched King of Kong?
Stevie
Of course.
Ross
Yeah, of course. So this whole story, it's not quite the same, but it's very similar where you challenged the inventor of Quake to a deathmatch and my understanding is you lost game one, and then won games 2 and 3 to take the series?
Stevie
That's correct. In fact, we had had a little bit more of an informal challenge earlier on, where I happened to be down visiting their office, they were down in Dallas, which was like the epicenter of shooters at that point. And the first time we played casually he beat me, and he bragged about it and was very aggressively loud about that victory.
Ross
A video game nerd being a dick? What do you mean?
Stevie
Never
Ross
What do you mean?
Stevie
It's shocking. And yeah, I threw down the gauntlet after that. I came back down and it was a best of three. He won the first one and then something snapped in me and the competitor came out. I was not going to let that happen.
Ross
Right. So you did what anyone would do. You dominated him. And then you dated him and dominated him again. And then dumped his ass in the most savage power move in the history of the world!
Stevie
I'm not going to deny that that is accurate.
Pouyan
What was it like being being a woman in in the gaming scene then?
Stevie
I mean, it's hard to even explain now because it seems like such a caricature. It is worlds away from how it is in mainstream tech now. There were so few of us. And you got to keep in mind, we were playing at these land parties and when we were playing multiplayer online, generally, you were going into the console of a game and like typing in the IP address of a server. So there was no Facebook, there was no Twitter, there was no TikTok like it was just IRC. It was very text heavy. So one of the things that made it unique is that you couldn't see anyone. So for a long time, I didn't know that I was one of the only woman and it was only through this course of revelation and starting to go out to live in-person events and talking to people that I realized, where is everybody? There are no women. And there were things about that that were really unique and door opening, but I think it was very polarizing. People either had a very positive outlook of, 'Oh isn't this exciting! There's actually a woman who is into gaming! Who's into what we're into!' And some folks had a very positive reaction to that. And some folks had a very negative reaction to that.
There's a lot of parallels in playing video games and being one of the few women in the room to... jumping sales.
Yes
Ross
You know? So can you talk about that transition? I know, you spent some time, kind of in the video game industry, doing some things, but then like, how did you find yourself into enterprise sales?
Stevie
So I got into making games. And then I was a product manager, a producer, of games. And that was my introduction to building software. So I was on the production teams creating software and it happened that that software was games. And that took me to LA. So I ended up in LA and I was working for Warner Brothers. And at Warner Brothers, I was making mobile games. And this was early days of not even smartphones, there was no iPhone yet, just feature phones. And we were making games with all of their IP. And I had this vendor. This guy had a technology platform that I was using as his customer at Warner Brothers to port that software to thousands of different phone models, which he used to have to do. And he and I had hit it off. I had bought his software. And he came to me one day and he said, You know, I need a junior salesperson and I think I could teach you to sell. What do you think?
My honest internal reaction was, I have no idea what that involves or what it means. I was very shy and socially awkward. And I thought it sounds incredibly uncomfortable. But I love a challenge so absolutely. I need to do this. This is clearly something that will help change my life. And either way, no matter if I pursue it long term or short term, it'll make me better. And I'll learn something. And I ended up taking the gig and that guy is now a VC. He's got his own firm and he took me on the road and just like beat me into submission and taught me how to sell.
Pouyan
That's so interesting that you leaned into that. I think a lot of folks would be like, 'Whoa, something new, something scary. No, I'm gonna stay here.' Do you know other folks that went from gaming to sales?
Ross
Was it not a bad word to you when he brought it up? Are you not like, 'Oh, that sounds gross' or...
Stevie
A little bit. A little bit. More than gross, it was just uncomfortable. Like I just, I knew it was something that was not in my bones and something I had no idea how to even approach. I had no idea. Nobody in my family has ever done sales, I had no background. But I do think there's something to that idea of leaning into that discomfort. And the challenge. That is the one common thread in my life is when I am presented with opportunity, I lean into it even if it's deeply uncomfortable. And in fact, the more deeply uncomfortable it is, the more likely I am to lean into it. Because there's growth in that challenge. And the truth is, it's like you get into this stuff.
And yeah, there are people who obviously built whole careers to end up here, but my mentor, George, who is a COO at Salesforce, he was such a great role model for me, he started as an intern at Salesforce. And I remember having a conversation with him at one point, he worked his way up over more than a decade there to be the CMO and then the CFO, and just hearing his story about taking that job for the first time. And I asked him, 'How do you even know what to do?' CMO at Salesforce was his first marketing job ever. Like how do you even know what to do when you sit down? And he said, 'The truth is most people don't know what to do when they take a job, especially at the executive level. You may not have the domain expertise and you really just lean into making it clear what you want people work on, give them clear priorities and learn and iterate. And that's all you can do.' And I've tried to roll with that mentality. That discomfort to me is growth. That's challenge. If you don't put yourself on the line, you don't get those kinds of opportunities.
Let's go to Twilio for a second. Because my understanding is you had a little bit of a fun run there.
Pouyan
I did.
Right, like going from IC to running a massive team in just a few years, but also being a top performing IC and there are a lot of folks there. So yeah, tell us about that.
Stevie
Yeah, it was a blast and I am so grateful. When I initially joined Twilio - I was the last hire before the IPO, I joined the week before the IPO - And at that point, there was very little sales. And it was really sales in name only. It was mostly like a team that was doing customer success and enablement. And there was not really there was no quarterly cadence, there was no concept of a committed contract. Like it was just this usage based self service machine running at a $200 million ARR run rate. And I was really fired up about joining. I had a friend in engineering so I'm maybe the only sales leader to ever be referred by a senior director of ENG and came in that way. I think that gave me a little more credibility.
And at that point, I was coming from running everything customer facing at an earlier stage, Series A startup. And they offered me a couple of options. And they said, Well, you can either take a role that's more of a management role running a partnerships team which is more senior or we've got an IC role. We've never done enterprise sales, you can be one of our first enterprise salespeople, and just crush a quota.
Ross
Oh, yeah, just crush a quota. You're just coming in like 'I don't know man, like, crush a quota.'
Stevie
Let's crush some quota. Like let's make a million bucks! Be our first seller and make a million bucks. And that's what I decided to go do. And it was unbelievable. My territory when I joined Twilio was every company over 1,000 employees west of the Mississippi River.
Ross
So why did we leave? We were too comfortable. We were - We were happy!
Stevie
Yeah we've established that I like to lean into discomfort. So, I was there six years. And I think that as somebody who likes disruption and likes challenge and learning, I hit that point of thinking I need to lift my head up and at least look around at what's going on in the market. Because you get to that point where companies might start to look at you and go oh, you're a lifer. Like what do you know you've been at one company for too long.
Ross
So are you a love to win or hate to lose person?
Stevie
I'm love to win. I think you know my instinct was to say both but deep, deep, deep down I'm love to win. I don't - I've really made a transition in my life. I'm not motivated by fear anymore. I'm now motivated by just the joy and that experience of the win and of growing and like, startup life is hard. There are lots of ups and downs and challenges and market changes the macro - everything that's going on. But that experience of winning as a team. Like that's... that's legit. So for people that are like cynical about sales, I see why they feel that way. But I don't know, there's so much joy in that team win.
Ross
Do you think it's possible to turn B players into A players? Or do you have to find A players?
Stevie
[I think it would be more appropriate to separate between C players and A players and in that case] I would say 98% of the time, no. There will be outliers. And at the bottom of that, somebody's got to have a growth mindset. There have got to be artificial factors that make them a C player, things that have held them back or lack of exposure is a big one. If somebody is a C player because they've got lack of exposure to what success looks like, that's fixable.
And I put myself in that camp. I would not be doing what I'm doing if I didn't have these mentors give me the exposure along the way. When I started out in that first sales job, I don't even - C player would be generous, like I was bad. I was really, really bad. And I had some people who taught me. So I do think people can learn and be taught, they just they need to have the curiosity and the hunger to learn. And if you do that you can extend.
Ross
There's nothing that solves all issues like winning. And when everybody's kind of losing, and there's just like universal loss right now so many people are kind of feeling down and rightfully so. But like, how would you rationalize that as someone who's just not lucky to be at a Vanta, where the product is crushing it and things feel all good?
Stevie
There are still ways to find wins. Even if you have bad luck and you've got bad territory and you're struggling in a market and you're not getting enough leads, whatever it may be, you got to look then for what is the secondary thing that you can win on. Okay, I'm gonna do everything I can do to make my quota. But if I can't do that, what's a win? Maybe it's a competitive takeout. A deal I can win that is a great takeaway from another competitor. Maybe it's a win in a specific vertical. Maybe I can establish an outbound motion that didn't exist before. Maybe I can generate more pipeline than anybody else.
Like, there are things that every person can control. And if you can come up with something that's a win in a different way, it gives you something, it gives you a story. And you know, as a sales leader, that's what I'm looking for. So if I'm looking for people across the org, I understand that performance varies and there are factors and those factors are very real. But when I'm looking at my team, I look for people that are telling me, I understand I didn't make my number, but here's what I did about it. I went out and I sent 100 emails a day and I generated this much pipeline and I figured out a new play. And I did this. I know it hasn't paid off yet, but I'm gonna keep hustling until it does. Those people I will always keep.
Pouyan
So is that who you would put in an A player category then?
Stevie
Yeah. A player is not necessarily about outcomes. There are a lot of people in the world that have had incredible outcomes that are not A players.
Ross
You're single mom and I can't even raise a succulent. Or an orchid. Orchids are apparently pretty hard. So I don't feel that bad or a cactus, which isn't that hard, but I've really struggled in that they're all dead. So can you - what is like the advice you have, I think there's a lot of folks out there in the world who are single parents and are like how do I make a career? How do I raise a human and also become a CRO?
Stevie
It is hard. I will definitely be honest about that. However, I think that at the heart of that is the reality that it's very possible. And that you don't need to apologize for having obligations or being a human or not being 100% work all the time because nobody is is the truth. Everybody's got other stuff in their lives. And the more you can just embrace that and be honest about it and roll with who you really are as a person. That path is very much open to you.
There are other incredible parents, moms, other CROs, one of my very best friends, Soumya Srinagesh Tulloss who is the CRO at Deliverr who just got bought by Shopify, she's amazing. She had a baby five months after taking the CRO role. She's crushing it. They just got acquired. Leandra Fishman is a mom over at Intercom, CRO. These people are out there. And we may be a little bit more of the exception, but I think that's less the case every single year. And I think it's about really embracing that reality and whoever you are just own it.
Pouyan
Stevie, I think you said something interesting in one of your interviews about how being a single mom or having a child actually influenced you to lean in more. Take more risks when most folks would consider saying, I need to be maybe more cautious and provide and I can't maybe take a risk on that job which I found really inspiring.
Stevie
Well, I think at the heart of that is part of why I like sales. It's that leaning into discomfort. For the first half of my career in sales, it did come from a place of fear. It was, 'I have gotta drive for it, I've got to crush my quota, I have got to do a great job at this because I need to provide for her.' And those early days with her - I've been a single mom with full custody of her since she was three. And right around the time, she was four, it was so rough. I was in a sales role and we were nearly evicted. I was babysitting for extra cash on the weekends because it was the only job I could do and bring her with me. And then I was like showing up on Monday to my sales job, ready to crush it! Like, you know, it was coming from a place of sheer terror about whether or not I could actually deliver and do the job and bring bring home enough money to support her and do what I needed to do.
Now I've been very fortunate in the middle of that run to have had some great outcomes. Some acquisitions. And I'm really grateful to be where I am today. So it now comes from a place of wanting to show her what success looks like. I want her to see what it looks like to achieve and there's no reason I can't do it. And I think that message of 'why not me' is something that anybody early on in their career, there are no rules. There's no super secret magical club that you have to be a part of to get into the Head of Sales or CRO role. It's just hustle and learning and challenging yourself.
Pouyan
Thanks so much for joining us. And I don't know, Ben, are we doing any sort of wrap up? I know Ross asked a bunch of questions at the end.
Ben Gould
Yeah, usually Ross and I will ask the love to win hate to lose question and typically the most competitive people will say 'I hate to lose,' but now, I don't know what to think anymore.
Ross
Yeah, that was the first time I've ever been convinced. I've ever considered love to win.
Pouyan
You said it with so much conviction and it's almost like you've transcended above the hate to lose.
Stevie
It's so true. I was a hate to lose person. That first 10 years. It's scarcity mindset. That's the thing. You gotta go, you got to transcend all the way to love to win.
Pouyan
If you see me wrangling with something.
Ross
She's just a creature. It's a creature!
Pouyan
When she punches it's like at that right height and it hurts. So that's why I'm very cautious around her... You love to win, or do you hate to lose?
Future Female CRO
Win.
Stevie
Yes!
Ben Gould
She's transcended.
Stevie
Yup, she's already there. Starting early.
