13: Stevie Case - Press Start to Sell: From Gaming Glory to Revenue Leadership

Discover Stevie Case's journey from Quake champion to Vanta's CRO. Learn how she turned a gaming background into corporate success, transforming minor opportunities into major wins with innovative strategies and relentless pursuit.

Episode Summary

Stevie, now the CRO at Vanta, was once known for her groundbreaking achievement as the top global player in the game Quake. In this episode, she shares her remarkable transition from dropping out of college to climbing the sales ladder at powerhouse companies like Twilio and Visa.

Discover how Stevie's unique start in the gaming world shaped her innovative approach as a female leader and single mom. We explore her seminal deal at Twilio, revealing how she turned a minor opportunity into one of the company's biggest wins through relentless pursuit and strategic thinking.

Uncover the art of leveraging product-led growth in sales, the importance of building genuine relationships, and the skill of turning technical complexity into lucrative deals. Stevie's story is a testament to defying odds, embracing challenges, and finding joy in the continuous game of business and life.

This episode is not just about sales tactics; it's about a life lived with passion and determination.


Stevie Case: [00:00:00] my favorite one, actually, the mostmemorable was with my COO George.[00:00:05] NowI am like, I'm definitely not a traditional seller. Like if you watch [00:00:10] my technique, like I, I do my own thing alittle bit and uh, I can be [00:00:15] a littlefreewheeling and sometimes that works and sometimes it doesn't.

Sometimes it really doesn't.

Michael Katz: [00:00:20] Thanks for tuning into The Winwire. Today,we're talking with someone I've been really excited to have on the show, [00:00:25] Stevie case, the chief revenue officer atVanta. Stevie's not just any revenue leader. [00:00:30]Before climbing the ladder at places like Twilio and visa, she had a prettyunique start, [00:00:35] dropping out ofcollege and becoming the top player globally in the game Quake, even beatingone of the [00:00:40] game's creators.

Stevie's story was recently featured in vanity fair, and what Iparticularly [00:00:45] admire about Stevie isher perspective as a female leader and a single mom, with such a rich [00:00:50] life already. We dove into her journey,which is full of unique insights and stories. [00:00:55]And of course we chat about that big win at Twilio that really changed ourcareer. Without further [00:01:00] ado, Steviecase.

Michael Katz: Stevie,welcome to the win wire.

Stevie Case: Thankyou. I am excited and [00:01:05] honored thatanybody would think of me for this. I do love the art of the deal, [00:01:10] so they probably just know I have a lotthat I take a lot of joy in the process, [00:01:15]so I'm, I'm excited to talk on it.

Michael Katz: Forsure. And I don't think we know, we don't necessarily [00:01:20]want to be like, uh, you know, the Anatomy of the Deal show that gets likesuper deep into every [00:01:25] tactic orwhatever it might be. but I do think, you know, there is a very big differencebetween [00:01:30] sort of the, veneer ofthought leadership and getting into, you know, how did someone actually do [00:01:35] anything or what actually was relevant tothem throughout their career.

And, you know, as, as you and I talked [00:01:40]before, you immediately jumped to this, deal that you saw as seminal uh, that [00:01:45] you worked on at Twilio, but you know,before we get into that, I'd love for you [00:01:50]to provide some background about your career up to this point. Right. And [00:01:55] for those who don't know, and there'splenty of, uh, information online to pore through about [00:02:00] Stevie, she's had a very interesting life, I think, bya lot of people's standards, from gaming [00:02:05]to sales and you know, you meet a lot of people in the industry who are prettyresistant to pulling back that [00:02:10]veneer. Maybe they're PR ready, maybe they're just not that much interestingabout them. Um, with you [00:02:15] it's theopposite, certainly. And so before we talk about that, like I said, can youjust provide an overview of how you [00:02:20]got up to this point, you know, what your initial journey was, you know, inlife, I guess.

Um, and then [00:02:25] finishoff with who you were at that time.

Stevie Case: Yeah,absolutely. I, I, I feel really [00:02:30]lucky and it has been a, a unique journey and it's funny [00:02:35] that you call that out. There is so muchout there about me and I feel like I'm [00:02:40]a very private person. Clearly the internet does not see it that way. You [00:02:45] know, I, I started out my professionallife thinking I was gonna become a [00:02:50]lawyer. I was like pre-law at the University of Kansas. I grew up in KansasCity area[00:02:55] and I just thought, like, Ilove law. I wanna go into politics. I love speech [00:03:00]writing like this. That was my real passion, but. Something happened to me in [00:03:05] college that changed that trajectory andthat is that this game [00:03:10] Doom that hadbeen out, I was introduced to it, and then Quake, it's, uh, [00:03:15] its successor came out and. Turned outthat I loved playing games and I was [00:03:20]actually really good at it. So I kinda lucked into this gaming career. I endedup [00:03:25] playing, uh, one of the designersof, of those games at his own game and beating [00:03:30]him, and that sort of snowballed into this, this career. It led me to dropoutta college. [00:03:35] At the time I moveddown to Dallas, I started making video games. And it led me to [00:03:40] truly what I see now was the product sideof software. And granted, [00:03:45] it wasvery specialized software. It was interactive entertainment. It was like deepand first person shooters, [00:03:50] but itreally was product and I. That led me on this journey. I ended up in la [00:03:55] I was working at Warner Brothers, um,making mobile games, and this is in the days of [00:04:00]feature phones, like pre-phone.

So we were making, uh, like games that had to [00:04:05] be ported to thousands of devices. And Ihad this software vendor and he approached me one day and [00:04:10] said, I need to hire a junior salesperson,and I think I could teach you [00:04:15] to dothat. For me that sounded deeply uncomfortable and like not in my [00:04:20] wheelhouse. And I've always been of themindset of like the more uncomfortable something is, the more you probablyshould do [00:04:25] it. 'cause it's gonnareally challenge you to just change and get better. And so I took the leap and [00:04:30] he took me on the road and I. He ended upbeing just the best teacher ever. He [00:04:35]was brutal. Like he put me through it and he taught me how to sell. He showedme how, and he taught [00:04:40] me how. Andyou know, 16, 17 years later, I've been in revenue that whole time.

[00:04:45] I've donepre-revenue startups. I've done the first million in revenue for, for startupsI've done, I [00:04:50] I did a series Bcompany that ended up selling to, to Visa. So I spent some time at Visa [00:04:55] doing like payments. I've been incommunications. I was six years at Twilio before this, and [00:05:00] uh, now I'm 18 months in at Vanta as theCRO and it's my first CRO [00:05:05] gig. SoI'm having a lot of fun and it's really challenging in [00:05:10]every way I could ever imagine and having a blast. It's really just a game of adifferent variety [00:05:15] if I'm beingcompletely honest.

Michael Katz: Yeah,of course. And I, I, I actually am always talking about [00:05:20] this a little bit, but, um, but you have someone who'sa competitive person in general, you have to kind of create these [00:05:25] little competitions for yourself on aregular basis saying like, what is the game of the moment? And like, [00:05:30] what does that look like?

And it's probably a lot easier in sales where at least you havea, a real life number that you can [00:05:35]say, look, here's what the high score is and here's what I need to beat. Um,but no, I, I think the journey's [00:05:40]really interesting so far. And obviously we're talking today about, um, . Akind of critical [00:05:45] moment along thatpath.

Uh, you'd obviously been in that next [00:05:50]act of your career for a little while. Uh, who were you at the time, [00:05:55] you know, when this deal at Twilio kickedoff? You know, what was your, were you confident, you know, at that point and,and what [00:06:00] were kind of yourmotivations at the time?

Stevie Case:Confident

Michael Katz: Yeah.

Stevie Case: Am am Iconfident at any [00:06:05] point in thisjourney? Probably not. Um, you know, I think that's, that is part of, and I'veembraced, [00:06:10] it's part of what makes meme is maybe I come off as [00:06:15] confident.I don't feel that in the inside like I am. I am my own biggest critic, and Ithink [00:06:20] it comes from just a desire toconstantly be optimizing and [00:06:25] doingbetter. And I am extremely competitive. We did strength finders this year,validated [00:06:30] my number onecharacteristic competitive. in this time at Twilio, it [00:06:35]was, it was a really formative moment for me. So I had joined Twilio[00:06:40] one week prior to the IPO and reallyunique [00:06:45] business because at thatpoint the business was 200 million in revenue. And [00:06:50]there was virtually no sales team and there was no real sales [00:06:55] process or discipline. So, you know, Iremember in those first couple of months, like there wasn't a [00:07:00] quarterly closed process. There weren'tcommitted contracts, like it was the total Wild West. The [00:07:05] business had built this $200 million runrate with purely self-service. [00:07:10]Product-LED growth. This is APLG business. It's part of what I loved and in my [00:07:15] career, I've gone back and forth betweenbeing an IC and being a a leader or [00:07:20]manager. And when I went back to Twilio, I was coming off of a run at a startupwhere [00:07:25] I had played honestly kind oflike a co-founder like role. I felt like I was shouldering a lot of [00:07:30] responsibility for the organization.

I owned everything customer facing, brought the business to, Iwas [00:07:35] first non-technical hire, sopre-revenue. Brought it to its first million in ARR and I was really [00:07:40] just looking to do something much morefocused. So When I approached Twilio, [00:07:45]I came in through a friend who was in engineering and they, they offered me acouple of roles and [00:07:50] one was more ofa leadership role, like running, an ISVs and partners team.

[00:07:55] And it was like moresenior on the org chart and would have a team. And then, then [00:08:00] they said the other option. We just hiredall our direct sales leaders and promoted 'em. So we do have [00:08:05] an enterprise AE role, if you would wannado that. I know it's like a step backwards and [00:08:10]I ended up picking the enterprise AE role and I was an AE at Twilio for thefirst two and a half of [00:08:15] my six yearsthere. And so as I'm doing the deal we're gonna talk about today,[00:08:20] I'm like about a year and a half into thatrun of being an AE and helping build the [00:08:25]enterprise business on top of this PLG self-serve [00:08:30]machine.

Michael Katz: Yeah.And so you're basically out there at this point saying, you know, you're happy [00:08:35] enough to be where you are. You want tojust go make a massive mark on the company, of course, and [00:08:40] establish that yourself. And candidly, youprobably had the ability to do that as even as [00:08:45]an ic. Given what the company needed.

And so, you know, [00:08:50]was this kind of a situation where you were the first to do something here? youknow, what did, what did this look like? And I guess [00:08:55]start taking us through it really blow by blow of, of what went down here.

Stevie Case:Absolutely I was, I [00:09:00] was reallyexcited to just go crush a quota. You know, the sales leader at the time said,we wanna build a sales [00:09:05] culture here.We wanna have our first salesperson, W two A million dollars. [00:09:10] And I was all in Yes, I want to do that.And I actually really [00:09:15] relished thatlike switch back from management, sales management into the IC role [00:09:20] because you see it differently and youstart to realize there's so many different ways to sell, so much more [00:09:25] creative than it might look. And you startto tap into all those other, uh, [00:09:30]just all those other tools that you see all their sellers succeed with that youdon't think would work but do.[00:09:35] Youknow, so as I was about a year and a half in here. We were really just starting[00:09:40] to like get the motion going of whatdoes it mean to sell to [00:09:45] anenterprise in earnest.

You know, Twilio had some great quote unquote enterprise [00:09:50] logos, but they were more like techforward, like Amazon, Netflix, and like these tech forward companies,[00:09:55] not like hardcore traditional enterprises.So in my first year I was [00:10:00] reallyfocused on logos 'cause we had this motion to like sign up and get, you know,commitments from [00:10:05] enterprise Fortune500 logos.

In the first 12 to 18 months, I think I did something [00:10:10] on the order of like 20 fortune 500 logos.And part of what made this so great [00:10:15]is I owned half of the United States as an a, an ae. So it had like this [00:10:20] massive territory. Every company over athousand employees in, in, in the us in the western [00:10:25]us. So I started trying to figure out how to leverage these opportunities outtathe [00:10:30] PLG funnel.

So like self-service developers signing up, experimenting,spending five, [00:10:35] $10 at a time. How doyou turn that into something? And a lot of those initial [00:10:40] enterprise deals came from that. It's likeyou talk to the developer, you understand what they're trying to do. You startto think [00:10:45] about how to get in touchwith power and figure out who the buyer is and like then turn that [00:10:50] into a committed contract of any size. Sopart of what I love about this [00:10:55] USAAdeal is that it started just like that with a developer signing up on thewebsite[00:11:00] going self-service pay as yougo, and just like experimenting [00:11:05] andbuilding this project in a labs group at this huge financial institution. And [00:11:10] that's really where the conversation withthem started.

Michael Katz: Yeah.Well, and I, I [00:11:15] think it's a momentthat a lot of other people can kind of empathize, empathize with of how do weeven start [00:11:20] to get this motionrolling and get known for something? Is it even possible? Um, [00:11:25] and you know, I think for people who know,USAA. Uh, you know, I think a lot of people have seen the commercials [00:11:30] that don't have a direct experience withthem.

It is really one of the vanguard businesses in the United [00:11:35] States and probably was something that wasintimidating at the time. Uh, you know, [00:11:40]how did you actually start that? How did you start to get in with them and howdid you like think about that approach of [00:11:45]building that bottoms up motion?

Stevie Case: So a lotof the magic that I think we [00:11:50] foundand a lot of what worked in this deal was. Embracing, embracing [00:11:55] PLG, and it's it, it's such a kind ofcounterintuitive thing as an enterprise seller [00:12:00]because I think there's this inclination that, oh, I need control over my deal.And [00:12:05] I think a lot of more classicenterprise sellers view PLG as a threat. [00:12:10]'cause they're like, oh my gosh, the Wild West, like anybody can sign up. Idon't have any leverage. I have no [00:12:15]control to get my deal done. If you can just go on a website. So I reallyflipped [00:12:20] that on its head. And withthis case, we had a, a developer that had signed up and [00:12:25] like clearly started building something, was doing somesimple SMS alerts and like mission one was [00:12:30]just get them on the phone and understand what the heck are you doing? And sowe [00:12:35] started this conversation. Turnsout they were building this like simple notifications use case, [00:12:40] uh, where they had like, uh, thisCharacter they had created [00:12:45] and theywanted to run this like loyalty program where you'd sign up for these [00:12:50] SMS alerts and you'd get these cute littlenotifications in the voice of the character that would encourage you to save [00:12:55] and encourage you to use more of yourtools that you've got available in the bank.

At USAA, [00:13:00] banking isjust one of their businesses, but like that's where it started. And they said,you know, [00:13:05] like. We don't know whatwe're going to spend $500. Like it started very small [00:13:10]and that's how a lot of these deals there did. And I said, great. So ratherthan [00:13:15] saying, okay, the person I'mtalking to is not the executive buyer, they don't have budget, it's a labs [00:13:20] group, it's whatever. I really went deepwith them and I just thought of myself[00:13:25]as their customer success person, and I thought, if I can make them successfulin [00:13:30] this use case. That's gonna openall of the other doors. So I educated them. I sent [00:13:35]them all kinds of, like, I'd point them at the correct parts of thedocumentation.

I considered myself their [00:13:40]personal support person, like whatever they needed, I would do it. I wouldfigure it out and [00:13:45] I would make themlike, feel as loved as possible as a customer. And you know, the program [00:13:50] launched and it turns out it was likeaward-winning. They, you know, it was kind of this like [00:13:55] novelty, but Won a bunch of like customer serviceawards. They're really invested in their quality [00:14:00]of customer service. So they doubled down on it and launched it bigger, and bythe end of [00:14:05] the year they hadactually spent a hundred thousand dollars. And now it wasn't in a committedcontract yet, [00:14:10] but they had spent alot more because it had gone well. So that was sort of like phase [00:14:15] one of the relationship, but I knew therewas a lot more to do with these guys. [00:14:20]But now I built a great relationship, so I had a base base to grow from really.

Michael Katz: Yeah, [00:14:25] of course. And I . Of course there's someof it, which is contingent upon their own desire [00:14:30]to do something in the first place and having to find that. But of course, likeany company, [00:14:35] um, at least in thetechnology space but elsewhere as well, is like, how do you even help theperson [00:14:40] understand what they might beable to do?

And I think a lot of people might just give up very [00:14:45] early on and say, yeah, this is probablynot worth the struggle. I, I'd rather not stick [00:14:50]out here anyways.

Stevie Case: Yeah, Ithink this is so common, and honestly, [00:14:55]that's the mindset that had to be reversed here because it was like a [00:15:00] $500 opportunity on paper in CRM. This isa $500 customer [00:15:05] and I just, you haveto take it on a certain amount of faith that if you get [00:15:10] them there and you show them what's possible, it's thisvery much,

uh, the art of the possible of like[00:15:15]Not only can you build great things with this, but let me show you [00:15:20] how easy it is. And this was a second waythat I think I differentiated myself [00:15:25]as a seller, was I became very deep on the tech and [00:15:30]I was very self-reliant when it came to like demoing and enabling. [00:15:35] So if my customer was trying to dosomething, I felt like I needed to know.[00:15:40]Exactly how to use the APIs that way, and what parts of the documentation aregonna matter and [00:15:45] what are the bestpractices technically, because you know, as a seller, you're, [00:15:50] you're never gonna be able to compete withlike the technical depth, even in a technical sale of your buyer. [00:15:55] They're always gonna know more than youtechnically. You can know more than them about your [00:16:00]own product, and that's how I viewed like my value. I can be, I can [00:16:05] answer your questions about everything onthe business side and I can answer all your questions on the technical side.And if [00:16:10] we go so deep that I can't, Iknow exactly who to bring in and I'm gonna serve that up on a silver [00:16:15] platter.

So it was like really making them feel like I provide a valuein every single interaction. [00:16:20] So theywould want to keep talking to me and they would want me to talk to more peopleat the company.

Michael Katz: Yeah, [00:16:25] of course. And I think it goes withoutsaying that when you actually make someone look good and, um, [00:16:30] share yourself as a really, as a resourceto anybody, and it's probably underrated just to even make [00:16:35] friends.

Stevie Case: Yes.

Michael Katz: but,um, , but they'll refer you to someone else too. And [00:16:40]so, you know, as you kind of approach that next stage, and I'm sure you weregetting a claim internally and, [00:16:45] um,within that, within their company, um, was this something, you know, [00:16:50] where you were just deciding to go on siteand visit these people all the time?

How'd you think about that next stage of [00:16:55] expanding from there?

Stevie Case: Oh yeah,there was, there was that like fuzzy middle area [00:17:00]where it's like, okay, we've had success together. I hadn't seen them in personyet. But [00:17:05] I knew there was more outthere. So with what I discovered was that this [00:17:10]group that built this first use case, they were part of a labs team, so theyweren't really [00:17:15] the people that wouldnecessarily have like a high dollar use case for me. [00:17:20]But we had a great relationship and they were great advocates. So I diddiscovery with them like[00:17:25] How do youall do these things in your company? Like who owns [00:17:30]notifications? Who owns the contact center? How do you think about technology?Like [00:17:35] who buys stuff? And they wereso, we were so friendly at that point that they were super helpful.

So they're like, [00:17:40] ohyeah, okay. Contact centers here. Here's the executive. It rolls up under, [00:17:45] here's how we think about SMSnotifications for the whole business, or like the whole bank at least. [00:17:50] So they started to give me some guidepostsbecause they wanted to like help me. 'cause at that point we were [00:17:55] friendly. And so they started making someintroductions and they said, Hey, there's some, some guys in our like [00:18:00] central team, um, that manage all the ITinfrastructure and shared services, [00:18:05]and like they saw what we're doing and they're curious about it, would you talkto them? So, had [00:18:10] a bunch of meetingswith these two guys and again, like Very technical guys, not the folks [00:18:15] who own the budget, but definitelyinfluencers, developers. This is another [00:18:20]place I think sales can go wrong. When you're, especially in a technical sale,you think, ah, developer great, [00:18:25] butlike, let me get to the person who owns the budget to the executive. This istotally backwards Like, [00:18:30] you needthat developer to love you. That person who's actually gonna implement thetechnology has to love [00:18:35] you and loveit. So I spent a ton of time with those guys and [00:18:40]they were pretty guarded. So they weren't really like telling me why they weretalking to me or like they [00:18:45] weren'twilling to engage in a lot of discovery. And that was the point at which Ithought, I, these, I need to [00:18:50] seethese people in the flesh. So the first place that happened is I got them tocome [00:18:55] out to our conference. So wehad this great user conference signals like really gorgeous, [00:19:00] incredible experience, like lots ofinvestment there. And USAA sent these [00:19:05]two technical guys out to our conference and uh, they had an amazing experienceand it [00:19:10] was hilarious in retrospectto hear why they did this. They said, yeah, honestly, our [00:19:15] executive sent us out to figure out ifyou're a real company or not. like we needed [00:19:20]to see firsthand, like, is this legit? Like what is this? Like, is this a real [00:19:25] going concern? Should we actually spendmoney here?


Michael Katz: They dotext messages. [00:19:30] Yeah.

Stevie Case: Yes.Yeah. We, we, we passed the vibe. Check on that.

And they're like, okay, [00:19:35]yes, this is legit. You're good. And that's what opened the door for me to thengo on [00:19:40] site. So that got me my firstmeeting at USAA in person.


Michael Katz: Got it.That is really interesting. And you know, there's one thing [00:19:50] that you mentioned that you and I talkedabout this at a very high level in a previous conversation, but[00:19:55] you're talking about expanding people,expanding usage throughout an organization. [00:20:00]And you mentioned this really interesting phrase, right?

You said you had to take a different approach, as you mentioned[00:20:05] to, to traditional enterprise sale.And the words you used were, but I also wanted to [00:20:10]make it feel like they're getting access to something special now. I thinkthose two ideas are actually [00:20:15] almoston their face. I conflict with each other is, yeah, everyone can use it [00:20:20] yet, it's something special.

And maybe you've learned some things from the, you know, gamingrollout approach and how that works too. [00:20:25]But how, how did you kind of think about that?

Stevie Case: Yeah.Gosh, there, there's a lot here and it's so [00:20:30]dependent on your business. For me, it all boils back down to like [00:20:35] confidence and framing. I think whenyou're inside a business and you're an [00:20:40]AE trying to sell something, you get very used to the things you have in yourbag. You get very used to the [00:20:45]technology.

So it's like really easy to forget that it's actually [00:20:50] special and you can give someone access toit. You know, in the case of Twilio, [00:20:55]anybody could sign up on the website, but the thing that made it hard forenterprises was that, um,[00:21:00] You weresometimes like prohibited by policy from doing that, and [00:21:05] you had to at least like put a credit carddown even if you weren't really gonna spend money.

[00:21:10] And a lot of peoplewould be really nervous about that. So the magic tool I had in my bag [00:21:15] there was I could give you access to aproduction account without you putting a credit [00:21:20]card on file and I could give you $20 of credit And it's a very simple thing [00:21:25] that I think we took for granted. But forme as a seller, I was like, This is huge. Like I [00:21:30]can, this is a big deal for somebody who wants to start building, and [00:21:35] I would really build that up with myprospects and say like, I am giving you a full [00:21:40]production account. Like you can build anything. You can try it all out. Youcan touch it all. Like [00:21:45] nothing isgated. You have access to everything. And then I would focus on [00:21:50] educating and enabling them. A lot of mydeals, what would end up happening, and it happened [00:21:55]here too, is in that kind of POC account with $20 of credit, [00:22:00] the developer would end up buildingsomething real and by the time I [00:22:05]negotiated with the folks who did own budget and could greenlight something,and we got to the contract [00:22:10]signature. The thing was already built, so it was like happening in parallel.And [00:22:15] I think you can do this with anykind of technology. You just have to think about what makes it special. [00:22:20] You know, my, the current business, I'm inAdvanta, we offer trials and [00:22:25] it's a,it's the same kind of idea, like, Hey, we can give you the keys to the kingdom.Try [00:22:30] it out, see how great it is.That has real value. I think salespeople can [00:22:35]forget that that's actually special.

Michael Katz: No,and, and also once it's in someone's hands, of course it becomes [00:22:40] a totally different, you know, you learnthat from going to the mall and the kiosks and people putting something into [00:22:45] your hand, and then basically by the timeyou don't wanna do it anymore, you're like, you know, the kids are telling theparents, we really [00:22:50] want this thing.

It's already in our hands now. And so, yeah, to your point,there's like this inertia effect, [00:22:55]um, that maybe you have there, especially with what you did. so I'm curiousabout kind of like what happened [00:23:00]next, right? You became this legitimate company. How did you actually go about,expanding there, especially [00:23:05] givenwhat you did was such a, I don't know, substrate right?

That uh, could [00:23:10]anything could be done with it. How did you kind of think about that nextstate?

Stevie Case: Yeah, wehad such a great base [00:23:15] at this point,so The next milestone for me was to sell [00:23:20]literally anything to the central IT group. Like I just wanted in with them [00:23:25] because I wasn't a real vendor in theireyes. Having sold to a labs group [00:23:30]like that was great. That was cute, but we were off on the side. I hadn't gonethrough the like [00:23:35] hardcoreprocurement process. I wasn't vetted by the central IT group, so.[00:23:40]

I had to crack that. And the way I thought about that was itdidn't even matter [00:23:45] how many dollarsat that point, deal size was irrelevant. It was about getting the door [00:23:50] open, and once the door was open, I knew Icould go get more. So I ended [00:23:55] uplike investing a huge amount of time in that because I knew that was like the,the first [00:24:00] Labs deal was great, butmy real land deal was this one with it, and [00:24:05]it took At least nine months of after that in-person conference meeting. [00:24:10] I went out there repeatedly. It's a reallyunique site. It's like, because [00:24:15]it's, they've got so many, um, military folks and like, because of the DNA ofthe [00:24:20] company, it's almost like abunker there in San Antonio. They've got this wild like. You know, [00:24:25] miles long underground tunnel system undertheir thing.

And it's just like this [00:24:30]incredible facility. It's really unique and they also have like a reallyspecial [00:24:35] culture. So the people areamazing. So I just went and spent a [00:24:40]lot of face time with them and you know, get your face in the place is veryreal. And I think people have [00:24:45]forgotten that post pandemic. Just like you build familiarity by giving accessto the product, [00:24:50] like getting yourface in the place really matters and you build relationships. And I, I [00:24:55] built relationships steadily. I. Up thechain. So I figured out who owned [00:25:00]that IT budget. Who was that guy's boss. I made friends with that guy. He was [00:25:05] lovely human being. And you know, wereally hit it off. And then we figured out who [00:25:10]owns the whole group. And then that guy turns out EVP, he actually reports tothe [00:25:15] CIO. So we started working thechain and then I started bringing executives from San Francisco [00:25:20] to meet those folks. So we would fly folksin. In one case we had a [00:25:25] whole day'ssession. We would, uh, just meet everybody and anybody from the [00:25:30] developers all the way to this EVP who wasinvolved. And it was all to build [00:25:35]credibility and crack that door. So in the end of that phase of the process, weended up with [00:25:40] a deal that was like aone year deal that was about five times the size of [00:25:45]the original labs deal. So now we're really getting traction. Things are [00:25:50] feeling really good. Like we have, we're,we're a verified vendor. And now what it was telling me [00:25:55] was, we now own your relationship with the company andwe will represent you to [00:26:00] othergroups who might wanna buy your technology. So now I'm in formally, it's stillthe [00:26:05] simplest possible use case, butyou know, we're, we're, we're multiplying the, uh, [00:26:10]ARR pretty dramatically at this point, but we were not quite yet done.

Michael Katz: Yeah.Well, and I, [00:26:15] of course, I mean,we've had a lot of episodes before where people have talked about this kind ofstuff where [00:26:20] it's, we talk about a, adeal win, but that doesn't necessarily mean one moment. [00:26:25] That means meeting those people. And I'm sure you hadto continue asking people, Hey, can I meet this person?

Right. It's [00:26:30] not justeven about impressing them, but it's Can you please introduce me and goingonsite and you're basically [00:26:35] a USAAemployee at that point. and so you've closed this deal. I'm sure you're gettingsome internal. [00:26:40] Recognition withinthe company. now, what keeps you from not resting on your laurels at thatpoint?[00:26:45]

Like what, what are the next, uh, stages?

Stevie Case: I, I,I'm not built to rest [00:26:50] on my laurels.That's not a thing that I, I do. Um, I don't enjoy it for some reason, I, [00:26:55] I like the discomfort of like continuingto drive forward. And it, I think it is the [00:27:00]gamer in me, honestly, because at each step it was sort of like [00:27:05] as you're in a video game and you walkfurther ahead and you can see beyond the fog just a little further,[00:27:10] the relationship was a lot like that.

So it was like, okay, now we've mapped out, we're a real [00:27:15] vendor. I've got all of my, I've got anextended team at this point starting [00:27:20]to get mapped into this organization, and I really started to discover [00:27:25] More about the company because bigcompanies are so complex and [00:27:30] in thiscase they've got like a banking, uh, group and they've got insurance andthey've [00:27:35] got like all of thesedifferent arms of the company. So I'm starting [00:27:40]to discover the dynamics of those and who makes decisions about how they [00:27:45] serve customers. And I started sort ofgetting into all those other little [00:27:50]Pieces and starting to thinking about, okay, the website, who owns live chat [00:27:55] on the website, the contact center, whoowns those voice calls and like what are [00:28:00]they using? So it's just like this very intricate, lengthy [00:28:05] process of deep discovery to figure outwhat else is out there. And I think this is.[00:28:10]One of the biggest mistakes salespeople make, they think of discovery as a,like a [00:28:15] one-time event or specific totheir opportunity. But if you really are [00:28:20]gonna go out and do the big deals, you gotta think about discovery as a never endingongoing [00:28:25] art and you've gotta talk toanyone and everyone.

You've gotta be willing [00:28:30]to ask questions that are beyond your comfort level. You have to like, ask forthe [00:28:35] introductions and help getpeople comfortable with them. So as we discovered that [00:28:40]bigger world, I saw two things on the horizon. I saw that with [00:28:45] the basic use case we had, that there wasstill more there and that there [00:28:50] wasan opportunity about six times bigger than the one I had just signed. If we [00:28:55] could just capture that basic SMS use casefor like the whole company. [00:29:00] And so Istarted going after that. At the same time I saw there were these longer term [00:29:05] opportunities. They had a contact centerand you know, Twilio does voice and chat and all these other has [00:29:10] a contact center platform. So I startedpursuing that at the same time. And at a certain point I [00:29:15] had all of these different plates spinningof different conversations and opportunities throughout the org.[00:29:20] And even the fact that we were in all ofthose conversations, Actually helped me get [00:29:25]to the point that we were able to close that six times bigger opportunity forthe same [00:29:30] use case, and at that pointthey became one of [00:29:35] Twilio's largestcustomers and the number two biggest Fortune 500 [00:29:40]customer at the company.

Michael Katz: Wow.Now, I mean, I guess the first thing I think [00:29:45]about is like, you know, you're talking about it in a bit of a procedural way.You know where is a lot of [00:29:50] meetings.Is a lot of people, there's a lot of hijinks, there are mistakes. Uh, [00:29:55] there are, you know, funny meetingsinternally and with the customer.

What are some of like the major [00:30:00]memories of how you got from here to there and some of the things that reallystick with you?

Stevie Case: Oh mygosh, I [00:30:05] laugh because there were somany, and like the people involved were so kind and so lovely [00:30:10] and we had built a lot of trust at thispoint. And like they definitely, I could tell at a certain point they really [00:30:15] wanted to do business with us, but thereare still the laws of physics and math and you gotta make it work [00:30:20] and. And I remember we had this, uh, thismeeting and the, the two guys, I [00:30:25]just adore them, Vaughn and Nome. I still consider them friends. We still have,still have them on [00:30:30] text. it was ourmeeting to pitch like the big proposal for the big, big deal, [00:30:35] the last deal that I closed before I leftTwilio and We went through the slides [00:30:40]and they were kind of like, I was pitching them on the value and they werelike, okay, okay, we're already in, like you [00:30:45]can speed up, like get, get, get to the numbers. And so I get to the numbersand I tell them, [00:30:50] here's what, here'swhat we're proposing, uh, for the pricing. And we're like [00:30:55] down to 30 seconds left in the meeting.

And they're like, Uhhuh, Uhhuh. Okay. So [00:31:00] this is about four times what we currentlypay. Like, let's keep talking [00:31:05] aboutit. like, oh God, no. Like I've just sank my own ship like [00:31:10] four times their current cost because wewere trying to migrate them off a competitor[00:31:15]and I was like, at the end of the day, like it was painful, but it was greatbecause [00:31:20] they had just given me anumber and now I knew. What their budget was. So [00:31:25]that gave me what I needed to move forward. It was a painful thing in themoment to think I'd come [00:31:30] in andForex the cost, but we worked it out and, you know, we ended up getting an a [00:31:35] reasonable premium, but still within theirbudget and they at that point, like they obviously couldn't [00:31:40] tell me here's what we spend, but theywere like, they were helping guide me down the path to make this [00:31:45] viable.

Michael Katz: Yeah.Well, and of course you're only gonna really get that response if you actuallysay something as [00:31:50] opposed to, tell meexactly what you spend, and then everyone's gonna lie anyways. You know, whenwe were talking before [00:31:55] you, youdidn't really get into it, but you didn't mention that there was one [00:32:00] memorable onsite that, you know, you kindof had a difference of perspective.

What, what exactly happened there?[00:32:05]

Stevie Case: Oh,there were a few here. I, my favorite one, actually, the most memorable waswith [00:32:10] my COO George Now I am like,I'm definitely not a [00:32:15] traditionalseller. Like if you watch my technique, like I, I do my own thing a little [00:32:20] bit and uh, I can be a little freewheelingand sometimes that works and sometimes it doesn't.

[00:32:25] Sometimes it reallydoesn't. And, um. In this case, we had brought, I had brought George out [00:32:30] and I had brought it like our salesengineer. I had like a team of five of us and we had gone on site and [00:32:35] we had a whole day with them. And youknow, a lot of it was technical, some of it [00:32:40]was business. And I think probably in retrospect, the right thing to dowould've been to just bring George [00:32:45]to the business part. But I just was like, George you're coming, like, you'rein for the whole day. [00:32:50] He was alwaysgame, so he was great. And George had been like the COO at Salesforce, likethis kind of [00:32:55] legendary guy. Likehe's seen what great looks like. So I, dunno why I opened [00:33:00] myself up to this situation, but I did.And so we were there all day and.[00:33:05] hadsome parts of that day that went really well. We had some other parts thatdefinitely did not like, I [00:33:10]definitely got, like, we had this part of the product where we were, we hadsome, like a version of how you [00:33:15]could implement the use case that was using our like well-established stuff andthen we had another way you could do it with some [00:33:20]more beta products. and it got, like, in that section it got messy and thecustomer was asking [00:33:25] like, which oneof these should we use? And you know, my, I, my technical team was kind offlailing a little [00:33:30] bit, and so Istepped in and gave a definitive answer. I did not know if it was the correct answer,but I was trying to like, get us back on [00:33:35]the rails. And, you know, I just remember coming outta that meeting and we getin the [00:33:40] car and like, I'm driving JorGeorge. It's just me and him. I, I now know [00:33:45]what this question means, but at the time I thought it was a genuine questionand he just said. How do you think [00:33:50]that went? It was like, I think it, you know, I think it went okay.

[00:33:55] Like I think it, Ithink we accomplished what we set out to do and he was just quiet. He was like,Mm-Hmm.[00:34:00] Okay, like he made it veryclear over the coming couple of days, he did [00:34:05]not think that had gone very well. Um, and he had some very concrete feedback [00:34:10] about how, and I think, you know, it wasall very reasonable feedback.

He was kind of like, you can't [00:34:15]let it get that off the rails. You gotta be more definitive. We gotta bebuttoned up about our products [00:34:20] inthese areas. And, you know, all of his feedback was super on point. And uh,[00:34:25] you know, I think for me, I was Ready topush us to the edge [00:34:30] and like get alittle more freewheeling on the edges.

And, uh, that was perhaps not [00:34:35]within the realm of what he was hoping to see. So we worked it out. We're stillgood [00:34:40] buds, but uh, that one was alittle painful.

Michael Katz: Well, Ithink it is one of those things where[00:34:45]two people coming in with different perspectives and different styles can beviewed as a clash. [00:34:50] one way to lookat things in life. I'm talking outside of this kinda stuff too, where you'rehaving two people [00:34:55] solve problems andbe on the same mission, but have very different approaches, and [00:35:00] maybe someone with that level of polish orthat approach would not have gotten to the point that you [00:35:05] got to there.

And so. I'm imagining it took some degree of humility, [00:35:10] forced humility for you to basically say,look what got me here. Yeah. Maybe that's not [00:35:15]the right move for that. Or even having your own opinion about here's why Iactually think it did go okay. [00:35:20] Um,and, and being able to still think about that and move forward and say, maybe Ishould change.

Stevie Case: [00:35:25] You know, this was one of my biggestlearnings when I first moved into a sales management role, because I [00:35:30] think when you come out of the AE role, anIC role, and you take your [00:35:35] firstsales management role, especially if you're really good at selling, which I, Ithink I'm pretty [00:35:40] good at selling. I.You come in with this preconceived notion of what good looks like and the right[00:35:45] way to do things.

And the biggest thing I learned as a sales manager for thefirst time was I was completely [00:35:50]clueless because I looked across this team of sellers and, you know, I wasmanaging an [00:35:55] enterprise sales team atTwilio. I, I moved up there, so I started with the frontline team. I grew upfrom three to [00:36:00] 15. I then took on asecond line role and I grew that org to 80, and then I [00:36:05]took on like a fourth line role down the line and I had a team of 130 managing400 million in [00:36:10] business. Andhonestly, the biggest eye-opener in all of that is that [00:36:15] there are so many different ways to get to a successful[00:36:20] outcome. A lot of 'em don't looklike how you would do it. And I had sellers do [00:36:25]stuff where I'm like, there is no way they're gonna succeed at closing thatdeal, doing it like that. [00:36:30] And I wasjust wrong. You know, people like being way more aggressive than [00:36:35] I was comfortable with some people justlike the way they put their thoughts together [00:36:40]and proposals together. I'm like, there's just no way that works. But it works.It taught me that like.[00:36:45] You, you justcan't always know And it is like, part of what I love [00:36:50]about sales is like the beauty of process and technology, but [00:36:55] humanity, you know, like there'screativity and humanity in this thing and everybody's got their [00:37:00] own unique way and I've really come torespect that.

And I think one of the best things [00:37:05]you can do as a seller is allow your manager and your executives into yourdeals 'cause[00:37:10] They're gonna becritical sometimes, and like you gotta be prepared to sort of eat it.[00:37:15] And if you are, you will get better somuch faster. It doesn't mean you're gonna [00:37:20]have to do everything like they think you should, but like that otherperspective is so valuable [00:37:25] and youjust gotta kind of suck up the feedback and, uh, that will [00:37:30] drive you to get genuinely better, muchmore quickly.

Michael Katz: I likethat perspective and I, [00:37:35] I do likethe perspective of basically being able to say, you're going to eat it either [00:37:40] privately or publicly. You might as welldo it publicly and make it at least a little bit impactful and [00:37:45] learn

something from it.

Stevie Case: like Icredit that as like the se, my secret to success at [00:37:50]Twilio. Like I was willing to bring anybody into a deal. I would put myself in [00:37:55] uncomfortable positions. I would bringJeff into deals. I would bring Georgia into deals and I. I, I [00:38:00] ate it more than once, like where I justlike had an interaction that was [00:38:05] notgood or like, not high quality or like, I don't know.

I remember one meeting [00:38:10]I had brought, brought Jeff into, and I don't know why I did this, but like I.Something [00:38:15] snapped in my brain and Ijust like, did not do discovery. We knew these guys and we had done so [00:38:20] much prep, and they came in and they'relike, yeah, we'd love to tell you more about our business.

And I was like, no, we're [00:38:25]good. Um, why don't we tell you about ours, And as after I got done with themeeting, I was like, what did I [00:38:30] justdo? And I did that in front of George and Jeff and it, it's [00:38:35] not that I didn't know better, I was justnervous and like, you know. Everybody screws up [00:38:40]in these meetings.

It's hu I saw them screw up in meetings too. So like a [00:38:45] willingness to do that will help you moveup and like you will become more senior [00:38:50]because like everybody's flawed. And if you can get comfortable with that, youdon't try to hide. [00:38:55] You're actuallygonna present as much more senior

Michael Katz: Yeah.Well, I, uh, at least maybe you can [00:39:00]make somebody feel bad for you in those cases, but, um,

Stevie Case: true.

Michael Katz: welljust to kind of tie [00:39:05] off on, on thisone, uh, with USAA, what made it so [00:39:10]meaningful for you personally? Did it open your aperture as to what you couldachieve in general? and [00:39:15] then . Youknow, are there any kinds of learnings or, or takeaways that you have eitherthat you [00:39:20] utilize now on a personallevel or that you think others could, could learn from there?

Stevie Case: Yeah, itwas super [00:39:25] meaningful to mepersonally for a variety of reasons. Like it was, it was part of what [00:39:30] established me. As a really successfulenterprise seller at Twilio, but that in [00:39:35]and of itself was really meaningful for me. I had in the startup I had been at [00:39:40] before Twilio, um, I was the firstpre-revenue hire. I owned everything [00:39:45]customer facing and you know, we were trying to break into the enterprise[00:39:50] and I had had, let's just say it was not avery supportive environment. It was [00:39:55]a challenging culture. I had had a couple of interactions there [00:40:00] where my CEO and some potential investorshad basically indicated to [00:40:05] me ormade it clear to me that they did not think I could [00:40:10]succeed at selling in the enterprise. That it was like beyond my grasp. And youknow, [00:40:15] it brought in like aconsultant who they thought could do it better. And they hadn't yet. Theyhadn't like pushed [00:40:20] me out, but theyjust made it clear they didn't believe in me. even saw that in writing in an [00:40:25] email that was forwarded to me that shouldnot have been basically saying that, yeah, I'm not the, the person to lead [00:40:30] enterprise sales. And so I came intoTwilio with this chip on my shoulder of like, [00:40:35]okay, like, let's go. Because I was angry. I [00:40:40]was like, I wanted to prove them wrong. I'm super competitive and it's part ofwhy I took the [00:40:45] enterprise AE role.One of the advisors to that startup company, same thing. He got [00:40:50] set up as kind of like a mentor to me, andI met with this guy and had this conversation [00:40:55]that ended with him kind of telling me about, he runs a company too.

He had a VP of [00:41:00] salesand he is like, you know, my VP of sales, he's got five kids, but he's on theroad every day, [00:41:05] never sees his kids,and he loves it. It's great. He said, you know, it just takes a certain kind of[00:41:10] person. He made it so clear in thisconversation that I was not that kind of person. So [00:41:15]here I am coming outta this startup where they're like, you're not the kind ofperson to be a VP of sales.

You're not gonna [00:41:20]succeed at enterprise sales. I'm like, well, I am gonna prove you extremelywrong. So that chip [00:41:25] on my shouldermade this entire thing means so much more to me to prove that [00:41:30] I could win in a way that people haddoubted me and. That [00:41:35] sticks with me.I love to win and I love honestly to be the [00:41:40]underdog. I like to win in circumstances where I am not expected to win. And [00:41:45] this one was at the heart of that, and itwas so human. I really take with me the [00:41:50]relationships from this deal and from working with this company, therelationships within [00:41:55] Twilio with thecustomer. It's a human endeavor, man. These are like people [00:42:00] and They have to want to work with you andyou have to make [00:42:05] it feel viable forthem. And you gotta think about their motivations and what [00:42:10] matters to them and what, why do they getup in the morning? And like that human element [00:42:15]of the sale is what I will always take with me. And it, it felt [00:42:20] so palpable here in this specific deal.

Michael Katz: That's,that is interesting and[00:42:25] what sticksout to me is I totally understand why a lot of people out there might [00:42:30] not be super passionate about what theydo. Or about the product they sell. And there's a lot of very boring things [00:42:35] to sell. I don't know. You sell chemicals,you sell, right? And, and you know, by an objective [00:42:40]observer, but the reality is what you've got.

And so at some point you gotta realize [00:42:45]that, how can I actually go help the people who need this thing on some level [00:42:50] and make that human? And maybe that makesyou a little more passionate about your job of saying, yeah, I'm notnecessarily [00:42:55] obsessed with this. Iwouldn't do this on my free time if I wasn't paid for it.

But. I would love to make [00:43:00]some relationships outta this. Um,

and, and I am curious, oh, go.

Stevie Case: Well,there's something [00:43:05] in there too. Ithink that there are traditional salespeople who are built like that. Like theycan sell anything, [00:43:10] right? Like I hada, a sales manager at Visa who told me once great salespeople, they [00:43:15] could sell Q-tips. Like they don't care.They just that and that is not me. And I thought at [00:43:20]the time like, yeah, maybe I'm like not cut out for this.

Like, that's not me.[00:43:25]I have to be passionate. I have to care. And. That might like, I sell [00:43:30] security and compliance now and I'm reallypassionate about it and it's something that, you know, [00:43:35]had you asked me 10 years ago, is that something I could be passionate about? Iwould've like not known enough to even [00:43:40]say.

And I think it just comes down to like, do you really care?Like how [00:43:45] invested are you in whatyou do? Because if you're selling something you believe in [00:43:50] and you're a part of a company that youbelieve in. The passion comes [00:43:55] and,uh, without that, like honestly I don't wanna do it. Like for me it's only funwith the [00:44:00] passion and you know whenyou can find that, that's what makes it great.

Michael Katz: So I, Ido [00:44:05] think it relates to what you saidbefore about bringing people in when you're uncomfortable is you might as wellfall [00:44:10] extremely flat on your face asopposed to just half-assing it, where it's like you might as well go out. In [00:44:15] a burst of flames and saying, I think thisis the best thing ever, and reject me all you want.

Then saying, yeah, you know [00:44:20]what, actually, maybe it's not so good. I'll see you later. Anyways.

Stevie Case: I wouldalways rather fail that way, honestly. [00:44:25]And it's like much more uncomfortable. But it goes back to how I got into salesand how I [00:44:30] got into gaming. It's likeI used to think this, like, if, if you have to cringe when you [00:44:35] hit the send button because you knowyou're like pushing the edge, or if you know that you're leaning [00:44:40] into an opportunity, this just makes youlike deeply, physically uncomfortable, [00:44:45]you're probably in the right place and you know it, it is gonna lead to [00:44:50] some spectacular failure.

And then it's just about You know, picking yourself up andknowing [00:44:55] we're all human and, and youjust go onto the next one and now you're gonna be better 'cause you learnedthat lesson

Michael Katz: [00:45:00] Yeah. And it will be okay. Uh, now the onething I I was thinking about as you [00:45:05]were talking is you, you briefly mentioned it having a very [00:45:10] notorious win in the game quick with oneof the game designers. Um, you [00:45:15] know,how does that compare to. This kind of achievement in closing this deal today?Do, do [00:45:20] you analogize those at all?

Which was more satisfying and you know, I'm sure you're morepassionate about one of them.

Stevie Case: I, [00:45:25] I, they are all equally rewarding if I'mbeing completely honest. Like it, it, and what I [00:45:30]see is the commonality of that win against that designer. So he, [00:45:35] I was playing him in person, this is likelate nineties, and I went down to their office in Dallas [00:45:40] and I. We were playing a best of three. Sowe played a, a death match [00:45:45] to 25frags, 25 points, and it was best of three [00:45:50]games with 25 points each. And I, I won the first death match [00:45:55] and then he won the second one. And in thethird one I was down badly. [00:46:00] So I wasdown like 16 to three and it was looking like I was gonna [00:46:05] lose. And he had made some Like he had, wehad a crowd there and [00:46:10] he had madesome kind of sexist comment and something like snapped in my brain. I was [00:46:15] like, I'm not gonna, I can't lose this.Like I'm not gonna lose this. I can't let [00:46:20]this happen. And I just went on a rampage and I came back and [00:46:25] ended up winning like 25 to 19. And so Iwon the best of three and. [00:46:30] Like thatcome from behind. I I love to win when it looks like [00:46:35]I'm not gonna win. And so it feels like that to me in business as well. [00:46:40] I love to fight. I love to be with theunderdog and I love to [00:46:45] overcomechallenges. So I don't want it to be easy in, in a certain way. And you know,if I'm in a situation [00:46:50] that feels tooeasy, I look for the things that are harder to go solve. Like I love to solvethose [00:46:55] hard problems and really facethose challenges head on.

Michael Katz: Well, Iguess it does [00:47:00] lead to an interestingquestion where clearly you've had this rich career, [00:47:05]rich life, you've had a lot of wins. Um, you know, you're clearly passionate [00:47:10] about your kid. Um, you know, one quotethat stuck with me that I read [00:47:15] from. The Vanity Fair article was about how it's never going to be as hard again.[00:47:20]

Right. You basically have achieved the success already. As youthink about that act [00:47:25] you're in now,you just mentioned, you know, I wanna be with the underdog. You kind [00:47:30] of can't completely manufacture thatanymore. You have to like fake it a little bit. Um, [00:47:35]what does motivate you at this point to keep striving?

Is that motivation changing over time? Is there [00:47:40] a specific mark that you wanna look back?Um, on that you've left, uh, as [00:47:45] youlook at things today.

Stevie Case: I thinkthe thing for me is that. There's never a destination. [00:47:50]There's never that like end goal that I'm trying to hit. To me, [00:47:55] it is that continuous game. So I find likethe joy and the [00:48:00] challenge in everyday of that interaction. And so for [00:48:05]me right now, you know, I'm at Vanta. I'm 18 months in or this like [00:48:10] series B growth stage company. And for me,the game now is like build [00:48:15] agenerational company, like build greatness and do it in a [00:48:20] way that is unmatched. And the beauty ofthat game and [00:48:25] doing it from the CROrole there is, there's not a playbook for this. [00:48:30]You know, we're selling, you know, this, this great security compliance [00:48:35] solution, SaaS solution in at a time whenthe, the market is weird. And you know, we [00:48:40]had 40 plus copycat competitors enter the market and try to take it from us. [00:48:45] And we've had all of this, you know, justchange. And it's hard under any [00:48:50]circumstances to build a company at this scale. So to me now it's in that fight[00:48:55] like, okay, we've gotten incrediblecompany that's growing in ways that are unmatched.

Like how do [00:49:00] we doeven better? How do we Exceed expectations on every axxis, [00:49:05] so it never feels manufactured to me likethat day-to-Day feels [00:49:10] hard andchallenging and so rewarding because there's no end point. [00:49:15] I'm not trying to like hit some goal andthen say, yep, I did it. It's done on the, [00:49:20]it'll never be done for me.

Michael Katz: So youdon't have to invent a new boss so much as [00:49:25]just find what that next one might be.

Stevie Case: There isnever a final boss. There is always a bigger [00:49:30]boss to come. You just gotta go find them.

Michael Katz: Well,that's what makes people so unhappy half the time. [00:49:35]But, um,

Stevie Case: I.

Michael Katz: welljust . Sure. Well, um, just to finish off here, [00:49:40]we always end by asking our guests about, you know, one to three of [00:49:45] the top mentors that really made an impacton their career. And, you know, if there are any stories that . [00:49:50] Really represented that impact that thosefolks had on them.

I know you already mentioned George is one, but um, are thereany other [00:49:55] folks that you would kindof bring up and mention?

Stevie Case: yeah,for sure. I mean, I, I got a double down on [00:50:00]George. He was a mentor, is a mentor and a friend. I would not be [00:50:05] a CRO without George. You know, heembraced my unconventional[00:50:10] approachand. I think that, like I thrived in a, in, he's, [00:50:15]he's known for being super harsh and like he's so smart and asks really hard [00:50:20] questions and I really thrived under thatscrutiny because I loved it.

Like I love to spar [00:50:25]with him and bring opinions and debate. You know, he did that for me and healso [00:50:30] supported me. He's reallysponsored me, uh, in a lot of ways, so I'm super grateful to call [00:50:35] him a friend and mentor. Another is MattGolden, who is the guy who gave me [00:50:40]my very first job in sales. Matt is now a venture capitalist. He was [00:50:45] running sales at this Canadian startup atthe time called Tierra Wireless outta Toronto, [00:50:50]and he just, he's a genuinely lovely person. He [00:50:55]also describe him as like, he was so harsh with me in a lot of ways. You know,he [00:51:00] took me on the road in thesesales meetings and after every meeting with a customer, I was so clueless [00:51:05] and I was so shy, and after every meetinghe just like totally [00:51:10] ripped me apartand just like. That was terrible. You said nothing of value. [00:51:15] Here's what you should have done. Like itwas so painful, but I don't think I've ever [00:51:20]accelerated my development so fast in my life, and it all came from a goodplace. I know he [00:51:25] wasn't trying to bemean, he was just trying to make me better. I. And, uh, and he really did,like, without him, [00:51:30] I would not havethis career. So those two guys, there are so many others. Nina [00:51:35] Reeves, who's somebody in gaming, uh, awoman who I really look up to who was an early, [00:51:40]early mentor and an actual other woman in gaming, like blew me away That. [00:51:45] She was in a leadership role and she hasalways supported me as well, so, so many incredible folks [00:51:50] along the way.

Alison Welch at Twilio, who's my, uh, ma direct manager for alot of [00:51:55] my time there. She reallyhelped pull me up. She gave me my opportunities as a frontline leader and a [00:52:00] second line leader at Twilio, and shejust, uh, supported me every step of the way. So friends and [00:52:05] mentors across the board. I'm so grateful.

I've had a lot of great ones.

Michael Katz: No, andit's always inspiring [00:52:10] to hear aboutthose and it is the hidden key to success behind so many great leaders. [00:52:15] Obviously they were, once those peoplegetting berated, as you just mentioned, , and so if they could [00:52:20] just take that on, they'll do that. But,um, but no, it's fantastic to hear about that for you and especially [00:52:25] throughout your many careers at thispoint.

But, uh, we really appreciate hearing it and, and thank you somuch.

Stevie Case: [00:52:30] Thank you for having me. This has beengreat.

Michael Katz: Thanksas always for joining us on another episode of The Winwire.[00:52:35] We'd appreciate it if you could share iton LinkedIn or Twitter, and rate us, or leave us a review on your favorite [00:52:40] podcast platform.

Helps others discover the show and join our growing community.

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