Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970

Stevie Case 0:00 ... I ended up as the world's first female professional gamer.

Harry Stebbings 0:03 (steady music) Stevie, I am so excited for this. We were just chatting now, you have the most incredibly cool background.

Stevie Case 0:09 (laughs)

Harry Stebbings 0:09 So, thank you so much for joining me today, first.

Stevie Case 0:12 Oh, thanks for having me. I'm excited to be here.

Harry Stebbings 0:14 Oh, so am I. This is gonna be a great discussion. But I wanna hear first, you're now you're CRO at Vanta. How did you make your way into the world of sales first, and then most recently, maybe skipping a few steps, (laughs) come to be CRO at Vanta?

Stevie Case 0:27 Well, you know, this is not the career I had envisioned for myself. This was very much, um, a path that I happened on along the way. I had these grand visions of going to law school. I grew up in Kansas, so Kansas girl, dad's a biologist, grew up on the prairie. And I was going to the University of Kansas and pursuing law, and I had some friends who were gamers. And so I got (laughs) really into games, and probably an understatement, I ended up as the world's first female professional gamer. This is late '90s, so dating myself a bit here.

Harry Stebbings 1:02 I'm sorry. That is such a cool title to have.

Stevie Case 1:04 (laughs)

Harry Stebbings 1:04 The world's first professional female gamer is one I would live on forever. But sorry, go a- and-

Stevie Case 1:09 That- that's my plan at this point.

Harry Stebbings 1:11 Yeah.

Stevie Case 1:11 I'm gonna run with that. And I'm just so grateful, because I really had this whole world opened up to me that I did not really know existed. And it started there. I lived in this gaming house for a bit, and we played, and it opened up this world of technology and computers. I learned to build my own PC, because that's what you had to do to be competitive. And it- it landed me eventually down in Dallas doing video games, and then out in LA working at Warner Brothers making mobile games. Like, this is pre-smartphone, okay? And I had this vendor. I was a product manager at Warner Brothers, making mobile games with their IP. And I had a vendor, and he approached me one day, and he said, "Hey, I need a junior salesperson, and I think I could teach you to sell."

Harry Stebbings 2:01 (laughs)

Stevie Case 2:01 And, uh, I had no idea what that meant. I was very e- very socially awkward-

Harry Stebbings 2:07 (laughs)

Stevie Case 2:07 ... very shy. And I thought, "This sounds deeply uncomfortable, and I love a challenge." (laughs) Like, "Let's go for it." And that was the beginning of my career in sales. And the company was Tira Wireless. The, uh, the guy, Matt Golden, at Golden- Golden Venture Partners out of Toronto, amazing guy, who just took me on the road and taught me to sell. He taught me through osmosis. He taught me through ar- example. And here we are nearly 20 years later, and I'm a CRO. Uh, a role I had never heard of, did not know (laughs) existed. And along the way, I've had some incredible people that taught me, taught me how to do it.

Harry Stebbings 2:44 We're gonna dig into each of those chapters. I'm just too interested. Do you think you lost the insecurity around people and the, um, a- as you said, slightly withdrawn nature? Or did you embrace it and use it as a strength? Which one is it?

Stevie Case 2:59 Oh, I definitely did not lose it. I have embraced it.

Harry Stebbings 3:02 (laughs)

Stevie Case 3:02 It is- it is part of me. I will never be able to fully lose that. And I think if you talk to people who know me now, they would probably be shocked for m- me to say I'm an introvert. I don't think anybody (laughs) around me believes me when I say that. But I am deeply an introvert. And it was actually Matt Golden, that initial mentor, who said something, who really opened the gates for me. And we were in a, uh, a- a meeting, a sales meeting, and we were meeting with some folks who were giving us a really hard time. And he said, "You know, the- the best way to open people up is to give them comfort with your own vulnerability." And he really taught me that, like, being human and being flawed was the best way to give other people comfort with being imperfect. And I thought that was such a powerful lesson. I've really embraced that over the years, and it's changed the way I think about humans. But I am still that same girl. (laughs)

Harry Stebbings 4:00 Can I ask you? So I totally agree with you, and I do actually, I use it a lot, don't laugh, in interviews to make people feel comfortable. Sometimes if they're a little bit cagey, I'll say, "You know, I'm really struggling. I had an eating disorder, and I just feel really fat th- this week." And just... (blows out air) Uh, and people open up more. In sales, it's a little bit of a different thing. You do slightly feel you have to project this kind of corporate air of confidence. Can you have vulnerability with clients in the same way?

Stevie Case 4:25 Yes. You can be both of those things at the same time. And I believe that's the place I've come to, that I am deeply comfortable with who I am, and I can still be confident. I can be knowledgeable. I can speak to you in depth about my product and its value drivers. But I'm also a human being, and I think ultimately, uh, people still buy from people. And you can be competent and also just a flawed human being who is uncomfortable and unsure at times. And I think if you can really embrace both of those things, that's the magic.

Harry Stebbings 5:01 I- I totally agree with you in terms of embracing both, and- and also with kind of authenticity. I hate the kind of fa- fake vulnerability that we see so much of today. (laughs) I wanna unpack a couple of elements. I spoke to Christina before the show, obviously your founder and CEO, and she mentioned that I should really pick up on the game designer and product manager to sales leader. How did being a game designer and product manager impact your mindset today as a sales leader? 'Cause it is a different background.

Stevie Case 5:26 It is. But there's so much in that that informs how I sell today, how I run teams today. I think there's one element that is games is really just software. And I was involved very early in my career in making software, and it was (laughs) very, like, cowboy version of making software. So, I have seen how the sausage gets made, and everything from, you know, how you put those pieces together, how the code gets written, to the strategy behind how you market something. Being involved in early gaming, we had to do it all, including distribution, and there was no social. (laughs) There was no going viral. It was all very... uh, you had to grind it out. So, that background and knowing how software works I think gives me a lot of empathy for what it looks like to build software even today.

Harry Stebbings 6:13 Yeah.

Stevie Case 6:14 And I think the other element of this, and part of why I think I'm a CRO at this point, is that...... games, they're all about strategy. Ultimately, it's the math, right? You have to put together a great strategy, and the math behind it to win. Being a CRO really is not all that different. You have to adapt constantly, it's very dynamic, you're putting together all of these different elements into a strategy, and ultimately, the math has to work. And really just, the score now is revenue, or it's users. (laughs) And as long as you're always optimizing for that outcome, that's how you win.

Harry Stebbings 6:50 I- I- I totally agree in terms of it really boiling down to math. Uh, we're gonna get into the math, uh, when we get into like a strategy discussion.

Stevie Case 6:57 (laughs)

Harry Stebbings 6:57 I wanna just unpack a couple more parts of your life which were,

Harry Stebbings 7:00 you know, really important. You're also a single mother, uh, wonderful daughter. How has that impacted your approach to your sales career?

Stevie Case 7:07 Oh my gosh. It, it's really changed over time, and this is a very fundamental part of my life. I've been a single mom, full custody, since my daughter was three. She's 18 now. So we've been at this a very long time, and early in my sales career, it was just me and her, before I'd had any kind of liquidity events and, you know, just remember early days of my sales career, taking sales calls and I'd be driving her back and forth to daycare or school and, you know, I remember one in particular, I was like trying to give a demo, but I was driving, and I had to take her through a drive-through to get her like a Frosty at Wendy's (laughs) or something. And you know, it's just always been in the mix, and I think for the first half of my career, it really just made me so much hungrier, because I have had something to prove, I've had somebody to fight for, I've had somebody that I had to achieve for, and I wanted to show her that I could do that. And in the back half of my career, I think it's really made me just... I don't have that same scarcity anymore. I'm really grateful. I've had great success, and I'm in such a good, safe place. But it's really putting me in a place where I don't take anything for granted. Like this whole ride, it's, it's so hard some days. Nobody's got it easy (laughs) every day in this business. This is hard. And the bad days, the good days, the struggles, I just am so grateful for every minute of it, and I really wanna embrace it, because I know that every minute I'm working, it's a minute I'm not spending with her, and I'm thoughtful about that. So it just makes me very in the moment.

Harry Stebbings 8:45 Can I ask, take yourself back to those early days when she was four or five. Kids are not as self-sufficient as they are when they're, you know, teenagers.

Stevie Case 8:53 (laughs)

Harry Stebbings 8:53 What drove you, when you were doing demos, when you're back to back with customers, and then you've also got a wonderful but also challenging four or five year old.

Stevie Case 9:02 (laughs)

Harry Stebbings 9:02 What drove you?

Stevie Case 9:04 Oh my gosh. A combination of stubbornness and desperation (laughs) and hunger to succeed. You know, I... So I- I recently told a bit of my, uh, early story from my gaming career in Vanity Fair, and so that was sort of the backdrop to where I was with her as a young kid. And as a part of that, some of the folks in my gaming life, when they found out I was pregnant, actually got an email from one of them in particular, uh, John Romero, who was in that story, my ex, saying, "You're pregnant, like, you're never gonna have a career. You're never gonna be the person that you set out to be, and you're making a huge mistake. Like, this isn't it. You were meant for something different." And I knew deep down a lot of people thought that, and I deeply, deeply, one, wanted to prove them wrong, and two, knew they were wrong. You know, I've always, I've always been a little bit of an outlier. That's how I ended up on this weird path, right? And I think in that moment of her being so young, the struggle felt so heavy, but deep down, the question my mind was still, "Why not me? Why can't I have these things? Why can't I achieve these things? And I'm gonna do everything in my power to make sure that I do."

Harry Stebbings 10:22 Do you think people still perc- we're (laughs) going down a rabbit hole, but I'm fascinated. Do you think people still perceive women post-labor and with children the same? I've seen it before where it's like, "Oh, Stevie's amazing, but I mean, now she's got a child. I mean, can we really count on her for those late night calls and the travels?" And it's not that you've changed, it's that the perception of you has changed. That's what I've seen. Do, do you think that's fair?

Stevie Case 10:46 Yes. It's extremely fair. It is still very real in many corners. I think the thing that has changed is, there are now places that we can work, that we can go, where people are more enlightened, (laughs) and they understand that you can be both of those things. You can be in that world of being a parent, whether you're the mother, the father, or something else, a caregiver. You can do that and still be an incredible, successful professional. So there are more pockets now where you're allowed to do both, but it is very much still out there.

Harry Stebbings 11:18 Can I ask twofold? (laughs) The joy of this show is just like the randomness.

Stevie Case 11:23 (laughs)

Harry Stebbings 11:23 Um, the jo- uh, but like, what advice would you have for women today, not necessarily in sales, but in our world of innovation, who are really concerned that actually they will be viewed differently post having a child? How would you advise them, and what do you know now that you wish you'd known?

Stevie Case 11:39 The single most important thing is don't apologize. Don't accept this narrative that it's a balance or a trade-off or you're giving something up somehow. It's up to you to define your own narrative, and you don't have to accept that idea. You can fully embrace...... everything in your life and make it a part of your narrate. Don't hide that you have to take your kids somewhere. (laughs) It is okay, and it does not make you less. And the more that we as individuals embrace the truth of our lives and can be honest about what we're going through, being a parent is just one of those things. You know, people are, especially now, struggling with so many things in life. And the more we can be honest about that and embrace that, the more we're all going to be able to achieve together and be a part of a team that is much more thoughtful and interesting and diverse.

Harry Stebbings 12:33 I think we need also other people to change, obviously also, uh, men who don't understand. (laughs)

Stevie Case 12:38 Yeah. (laughs)

Harry Stebbings 12:38 Um, can you help me? I am a hypothetical founder and CEO. I want to create this inclusive environment for my team. How can I do that? What can I do proactively and deliberately to make all people, men and women, feel that children can be a net add, not a net subtraction?

Stevie Case 12:56 Yeah, I, I really don't think it takes a lot. I think that step one is genuinely caring about the people that work for you and asking them about their lives, whatever those lives include. And if you show a genuine and ongoing interest in the human beings on your team, that acceptance and that inclusive environment ultimately will be created. It's really just people just want to be seen. This is one thing. Parenting is one thing. There's so many others, but people want to be heard, they want to know they can be themselves. And if you just open the door, you don't have to understand, you don't have to do anything very specific other than see them as a full human being in everything they're dealing with in life.

Harry Stebbings 13:42 Yeah. No, I, I totally agree on people just wanting to be seen. Um, (laughs) getting out of the rabbit hole, otherwise I could-

Stevie Case 13:49 (laughs)

Harry Stebbings 13:49 ... go down there, uh, a long time. Uh, y- I, I spoke to Christina, as I said. She mentioned George Hu before. Um, what did you learn from George at Salesforce that was really instrumental

Harry Stebbings 13:58 for you?

Stevie Case 13:59 Oh, my gosh. George is... So George is one of those pivotal figures in my life and career as well. And George came to Twilio about six months after I joined Twilio. So I joined right around the time... I was the, actually the last hire pre-IPO. And I came onto a sales team as an enterprise seller, because I've gone back and forth between being sales management and an IC role, and I, I really wanted just an IC role building the enterprise sales team there. So George comes on about six months later, and George radically shifted everything at Twilio. He was a sales leader who Geoff Lawson respected. They had this great partnership, and George made the case for sales and for go-to-market. And over the coming years, George and I built this great partnership. And part of what his, part of his story that resonated with me was that he has a very non-traditional story of success. You know, he started at Salesforce as an intern, and over the course of, you know, over a decade, he ends up as the CMO and then the COO of Salesforce, which is just this wild backstory. And the way he navigated that was so incredible. So at Twilio, he similarly kind of partnered, like identified me in a way and, and picked me out and continued to like have my back and educate me about the next step at each step. And, you know, by the end, he and I had developed this great relationship, and he would challenge me. He challenged me through almost like haikus. He would give me these like, "Here's a couple of lines about the thing you need to learn next. Go figure it out." And he would certainly not do it for me. There were times when he would say, "Okay, there's this really important meeting that happens at Twilio once a month. Basically, there's only like SVPs and above in it, but it's the most important meeting. You should get yourself into that meeting. Go." Now, he could have put me on the invite. He did not. (laughs) He challenged me to go figure it out. And, you know, a lot of the wisdom of George, this is one of the smartest people I've ever met, at the end of the day, it's about math. He's got a great model, probably one of the best analysts out there, and understanding the way that he thought about the business, the model behind it, what matters, how you play that revenue game, was ultimately the playbook that he taught me. And so grateful that... He's still my first call when I get stuck (laughs) on a problem, still very much my first call, and it's radically changed my life through his support and sponsorship.

Harry Stebbings 16:29 I've learned that it's really important to not be afraid to ask the stupid questions. (laughs)

Stevie Case 16:34 (laughs)

Harry Stebbings 16:34 When you say, "The revenue game," what does that mean?

Stevie Case 16:37 I mean, th- what it really boils down to is the math behind success. And the thing that George brought to Twilio that was such a revelation for me was... I think when he arrived, we had this grand plan of we're gonna... We, you know, IPO, we were $200 million run rate, and Geoff had set out this vision of we're gonna get to a billion dollar run rate. But then behind that, there weren't really, (laughs) there weren't really any mechanics. The math wasn't there. You know, we were just gonna make more great product and like have a self-service experience and more developers would buy it. What George brought was an operating model and the math that actually proved out how to get there. At its base, it really is a very simple concept, but in execution, it is so nuanced, and you have to get really good at managing that model. But really, it's about reve- r- r- it's about winning that revenue generating game and how do you continue to make things go up and to the right in a predictable way. Not on hope, but something-

Harry Stebbings 17:46 (laughs)

Stevie Case 17:46 ... that you can control (laughs) that's gonna drive revenue up and to the right.

Harry Stebbings 17:50 So if we think about it, you know, obviously Twilio had the, the self-serve developer-led motion, and then you and George really kind of pioneered and brought in the traditional enterprise sales motion. I often see startups today thinking they can do both

Harry Stebbings 18:03 from day one. Can you do PLG and traditional sales, enterprise sales from day one? Or does it have to be in a staggered motion?

Stevie Case 18:13 Uh, it's such a difficult question that is so custom to each business.You can, but I would caution you against trying to do both right away. I think in the early days of sales, you have to be very, very clear on what is the value prop for the customer and what is that experience? And when you try to combine PLG and a sales motion, often what happens is customers get confused and sales reps, and your sales team more broadly, get very wrapped around the axle about the mechanics of who gets credit. And that's one of the harder things when you're trying to piece apart PLG and sales is, like, who really gets credit if people sign up on the website, but then a salesperson closes a deal with them? Should they get credit? Should they get comped? How do you work that out? And when you introduce both too early, you, you introduce the risk of complication. So, I think a much more effective model is if you're gonna start with PLG, you've got to focus instead on customer enablement and customer success, and it might include elements of selling. But it's gotta be success first. It's gotta be engagement first. Otherwise, if you're just trying to go at commercialization from two different angles, everything gets messy.

Harry Stebbings 19:32 So, I totally... I love that in terms of kind of PLG and tailor that with customer success and enablement. There comes a time when you do want to layer on traditional enterprise sales. Respectfully, it sounds like you waited quite a long time with Twilio.

Stevie Case 19:46 (laughs)

Harry Stebbings 19:46 It could have been done a little bit sooner. My question to you is, for founders listening who have the PLG model that's working, how do you know when is the right time?

Stevie Case 19:56 I think that there's no one clean answer, and there's also rarely a way to know in advance. And I am a big fan of testing. I think that sales should be approached in an iterative way that is similar to software development. And when you've got a PLG motion, one of the things you can start to test is, if you put somebody on that relationship, you put a human being in the mix, can they actually get more revenue from the customer in a way that the customer also is happy with? Can they solve a problem that can't otherwise be solved? And if you can add those two experiences together and get a better outcome, then that's when you should do it. And the only way to know often is to start to experiment with, uh, with that and put somebody in the mix and, and see what you can drive. Uh, I think a lot of it too comes down to who is... who's your ICP? Who are you selling to? Because if it's SMBs, you can be PLG all day and they're gonna love it as long as you make their life easy. But if you're trying to sell into an enterprise, I... I... I am pro-PLG in the enterprise, but you've got to have some sales folks to back it up as well, because they always have needs that cannot be automated away.

Harry Stebbings 21:09 Do you struggle in terms of that expansion into the enterprise on the value prop perspective? Because the value prop changes incredibly when you're selling from an SMB or a startup to Cisco or Chase or First Republic. It's very different. How do you think about what changes when making that transition and how you deal with that as a sales leader?

Stevie Case 21:30 You know, it is really a fundamental shift in the story of the problems you're trying to solve.

Harry Stebbings 21:36 Mm-hmm.

Stevie Case 21:36 And that doesn't necessarily mean that the product has to be radically different. You know, we're in this mix at Vanta right now, in that we have been historically SMB-focused, and we've got great traction and success with startups and companies under 200 employees. Well, this year we made the move upmarket, and we've started to see tremendous success with larger customers. But the value prop is very different. The underlying product is the same, we're an automated compliance platform, but our SMB customers are solving the problem of addressing compliance for the first time, getting their first SOC 2, doing that th- the first time they've ever done it as a company and standing up a security program. Our enterprise and mid-market customers are solving something very different. They want a single pane of glass for compliance in a much more complex, larger organization, and the way they measure success against that is very different. So, an SMB is measuring, "How quickly can I complete this process to prove I'm compliant?" And a mid-market customer is really measuring, "How much time can I save? How much risk can I reduce?" So, underlying all that is one product, but we have to tell the story and talk about the value drivers in very different ways for those profiles.

Harry Stebbings 22:56 Can I be bold and ask, why did you decide to make the move into enterprise? I always think a big mistake that startups make is they move too quickly into enterprise, and we always forget just how huge SMB is. I mean, HubSpot (bleep) .

Stevie Case 23:08 (laughs)

Harry Stebbings 23:09 Like... (laughs) So, like, why, when it was working so well in SMB and startups?

Stevie Case 23:15 So, for us, it's additive, and we will always keep SMB at the heart of the work we do. But the truth is, we are being led there as a business. We are seeing success that we didn't pursue, but came to us in those segments. So, this is another opportunity for us to start to experiment. So, we started seeing, for example, mid-market customers and a couple of enterprise customers come in. And so, in the middle of the summer, I created a team just to go after those mid-market and enterprise opportunities, because it is... it's a very different cycle. So, put that team on a different comp plan, gave them a little bit more space and time to experiment, ran it as an A/B test, and right out of the gate, they killed it.

Harry Stebbings 23:59 That's really interesting, 'cause that feels like a little kind of toe-in-the-water test to see if it worked. But I always hear that you've got to be fully committed to enterprise or fully not. And I'm like, "Oh, that sounds quite scary."

Stevie Case 24:13 (laughs)

Harry Stebbings 24:13 Do you not have to be? And for founders listening, can you test it in a more gradual way?

Stevie Case 24:19 You can test it.... with the caveat that these things are radically different. So, the way that I'm testing that in our business was to inch up market. (laughs) It wasn't necessarily to cut over from SMB to suddenly we're gonna go do deals with companies 5,000 employees plus. It was, "Okay, let's look at the patterns of success we've had with companies over 200 employees and what is common among them, and can we take a small group of folks and go see what they can make happen?" And the thing that was not toeing the water about it is that I actually pulled resources out of our core SMB team, and their job, 100% of the time, was mid-market and enterprise. So, they didn't... I think the thing that goes wrong is when you've got a team focused on one segment and you ask them to dip a toe in the water of another segment, and it's very hard for any one person to both do, you know, high-velocity, bottom-of-the-market deals and also do strategic deals. They're always gonna go to whatever is going to have the best results for revenue and comp and whatever they know how to do best, so you have to have this division of labor for folks who focus exclusively on that experiment.

Harry Stebbings 25:35 I mean, that hat-switching must be very difficult. I mean, obviously I- I say it with this brilliant Panama hat.

Stevie Case 25:40 (laughs)

Harry Stebbings 25:40 Um, that must be... We're gonna get to hiring a team. Uh, you mentioned the word repeatable earlier, which really kind of rang out to me 'cause everyone says about playbooks in sales are repeatable. And I always think, "Well, that sounds wonderful. It should be a fridge magnet."

Stevie Case 25:52 (laughs)

Harry Stebbings 25:52 Um, so tell me, does the founder need to be the person to create the sales book, or can it be an experienced sales leader that's brought in?

Stevie Case 26:00 I think that it- it really depends how you define that playbook. I think the elements of the early playbook a founder should develop are initially the story. That founder has to be storyteller-in-chief, because there's an element in early sales of trust. When you're trying to sell to someone and they know they're coming on as one of your first customers, they need to believe in the vision. They need to buy in with that founder. So the founder has to be the first salesperson. They have to be able to talk about the story, those early value drivers, and the why behind why someone would work with this product. What's the real value? So, that part of the playbook has to be built by a founder. But you know, when I think of a playbook, I think much more of the, "All right. We've got product-market fit. We know what it is. Somebody's gotta write down on paper what are the mechanical steps that every new rep has to know and master to succeed at selling this product." And I think the challenge... If you try to ask a founder to do that too early, it, uh, puts you in a position where you can't iterate as much and you maybe feel you're committed to something without really knowing yet if you've got the right ICP, if you've identified the right value drivers and you're on the right path.

Harry Stebbings 27:18 Yeah. So say we do have a playbook, and say... I- I- I am fascinated again by the kind of idea of testing a little bit the expansion up. When we think about structuring our team, moving from a PLG motion

Harry Stebbings 27:32 to a more traditional motion, I'm the founder, you're my angel investor and advisor. Thrilled to have you, Stevie.

Stevie Case 27:39 (laughs)

Harry Stebbings 27:39 Um, uh, do I hire a head of sales first? Do I hire two SDRs, two AEs? How do I structure my first foray into the world of sales?

Stevie Case 27:50 You know, it depends a lot on your ICP.

Harry Stebbings 27:53 Yeah.

Stevie Case 27:53 I think that if you're going after enterprise customers, you likely just need one to two really great enterprise salespeople who are creative and understand how to open doors. If you're going after SMB, little bit of a different story. I think there, you want somebody who understands the mechanics of scale and velocity. So, in that case, I think it becomes more of a player coach, an athlete, somebody who can do some of those first deals but really starts to understand, how do you build a machine that can do this with speed? And you know, in between, you've got to have a founder who stays engaged, because that is going to shift. Between the time of that first sales hire and when you get to the point of actually scaling a sales team, your business will radically change multiple times. And the biggest mistake folks make in there is thinking, "Oh, I'm gonna make a s- great sales hire." They get bamboozled by a really, like, sexy resume, somebody who's succeeded at, like, a great brand name company. They bring them in, they sit them at a desk and like, "Go sell," and they fail, because the founder has delegated something that is so core that is not yet baked to somebody who may be very bright but isn't in the weeds enough.

Harry Stebbings 29:15 What should that engagement be like then? Me, the founder, sitting next to the person every day, them joining calls with me? How would that look in an ideal world to you to prevent that mistake from happening?

Stevie Case 29:26 I think the single most important thing in that is that that first sales hi- h-hire has to be glued at the hip with the founder, and it's a matter of joining every call with the founder. It's a matter of the founder sitting down at a whiteboard and whiteboarding the vision and telling the story, because your first sales hire has to be able to speak as if they were a founder of the company. That is typically the most successful model. When you get that first person in the door and they're now basically in the seat where they sound like a co-founder and they can speak to the why and the vision with ex- enthusiasm and passion, that's how you get success. And the best way to do it is just to model it. Let them hear what it sounds like to tell the story. And I think the mistake people make, especially when they think about the playbook and they're like, "I've hired this salesperson," is they try to write it out in a document and they're like, "Here- here's how you do it. Go do it." And the salesperson just cannot... No human being can recreate...... that storytelling and the passion of a founder if they just read it in a document. They've got to be there, so default to including that salesperson in every conversation, and not just sales conversations. Let them listen to you when you talk to investors, when you talk to partners, when you're talking broadly about your company and why you built what you built. They need that whole story so they can be fully audible-ready, and they can sound like a co-founder of the company.

Harry Stebbings 30:51 Sh- okay, i- if you were to choose between someone who's got domain expertise in your domain that you're selling into, so it'd be a previous history with a selling to that customer base, or history selling that ACV size, that contract size, which is more important?

Stevie Case 31:08 Neither. (laughs) I would say-

Harry Stebbings 31:12 I wasn't, I wasn't expecting that at all. (laughs)

Stevie Case 31:13 I would g- of those two, I'd go ACV.

Harry Stebbings 31:16 Uh-huh.

Stevie Case 31:16 I think that it's actually much more important that somebody understand the profile and they understand the mechanics of doing a deal of that size with that profile. They can learn the ser- subject matter expertise in many cases. I actually think the most important thing in early hires is, is that person a hunter, or are they used to taking orders?

Harry Stebbings 31:37 Ah.

Stevie Case 31:37 And that grit that it takes to be somebody who can open doors and hunt, that person will succeed over others in every possible scenario. So you gotta look for somebody who is comfortable with that and does not expect business to come to them.

Harry Stebbings 31:53 Do we ever want someone to take orders? Like, if we think about those two motions, the enterprise versus the higher velocity, is the hunter one and the take orders the other? Do we ever want someone who takes orders? How should we think about that?

Stevie Case 32:05 Yeah, I think there's a place for people who take orders, and I think particularly early career, when you've got a velocity business, and you've got a playbook, and it's very clean, and you know exactly how the math works, there's a lot of value in somebody who can just very efficiently take those orders. I don't think that's the world we live in anymore. (laughs) I think with the, uh, shifts we've seen in the macroeconomic environment, we are, we are no longer in a growth-at-all-costs world. We are no longer in a world where business is just going to come to anyone, except maybe those lucky few out there. I don't know who they are, (laughs) but-

Harry Stebbings 32:39 Ah.

Stevie Case 32:39 ... I think that we're in a world where everyone now has to be a hunter, and every member of your team has to be accountable for cracking doors and breaking down barriers. And grit is going to become infinitely more important over the next 18 months.

Harry Stebbings 32:56 We won't talk about Gen Z entitlement-

Stevie Case 32:57 (laughs)

Harry Stebbings 32:57 ... 'cause I might just get on a high horse-

Stevie Case 32:59 (laughs)

Harry Stebbings 32:59 ... so we'll just move on from that. Um, uh, y- you mentioned grit there being a characteristic. We're gonna build the team together now, very exciting. What non-obvious characteristics and attitudes make incredible 10X sales hires from your experience?

Stevie Case 33:15 Uh. For me, it's about a couple of things. It is about grit, number one, and grit is not necessarily just being a hustler or somebody who pushes really hard. Grit is about hanging with something hard over a longer term and actually making it happen. So, when I look for grit, I'm looking for somebody that has picked something hard to accomplish and stuck with it through adversity to make it happen. So, that's one. And the second is curiosity.

Harry Stebbings 33:45 Ho- ho- ho- let- let's bring that-

Stevie Case 33:47 Yeah.

Harry Stebbings 33:47 ... how do you test for grit? I'm, I'm a candidate. I want a job with you at Vanta. How do you test if I have grit?

Stevie Case 33:54 I think that you've got to get to the heart of, what are some of those accomplishments that person is very proud of? And they don't have to be at work. I think there are people who are very early career who have tremendous stories of grit, whether it's something they accomplished in their, uh, pursuit of a great education or something they accomplished on a human level that was really, really hard. It could be a hobby. I think asking about those things, you wanna see passion, you wanna hear stories of overcoming, and if you can get those stories out of someone, those are the kind of people that will be resilient in a really dynamic workplace, and they will figure out how to win, even as things change.

Harry Stebbings 34:38 I always wanna see discipline that means sacrifice. And it could be, like, incredibly grueling exams, which mean you have to study so hard and you lose a load of social. It could be doing ultra-marathons, meaning you miss birthday parties and great food, but, like, pain as a result of discipline-

Stevie Case 34:55 Yeah.

Harry Stebbings 34:56 ... which sounds very horrible of me. But it-

Stevie Case 34:58 I think that's real though. I think that is, that is real. And when I think about why I have been successful, some of those things are really at the heart of, of my story. You know, I actually dropped out of university all those years ago, 25-plus years ago, to go be a pro gamer. And so, as I made my way into tech, into sales, in my early career, there were lots of places I could not even get to an interview because I didn't have a degree. And, you know, I, I couldn't even get in the door at, like, (laughs) Google or, uh, a Meta or these places that were so aspirational they wouldn't even speak to me because I did not have the pedigree. And I decided over time that it was really important to me to complete the degree. And so, over the course of 25 years, I basically did a class at a time, and I'd take breaks, and then I'd come back to it. And even as I was a single mom, I was doing a class at a time in my free time at night, and I actually graduated and got my undergrad degree during the pandemic. So, it's like, that is the kind of stuff I'm looking for in people I hire, is just the determination.

Harry Stebbings 36:08 Can I ask you a really rude question?

Stevie Case 36:10 (laughs) Of course.

Harry Stebbings 36:12 Why did you do that? It's wonderful and it's amazing, but you're a proven sales leader with immense success. You don't need a fucking undergrad degree now. (laughs)

Stevie Case 36:23 It's very true. It is very true, but I wanted to know I could do it, you know? It was a personal challenge for me.So it- I, I felt like it became such a part of my story and identity, like, "Oh, I'm a college dropout. I didn't do that," it started to bother me. Like, I wanted to prove that I could overcome this thing, and it wasn't about proving it to somebody else. It was about proving it to myself, and in the end, it doesn't change anything about my career, but I was- it just felt so good to get it done.

Harry Stebbings 36:56 I, I, I think you're so awesome. (laughs)

Stevie Case 36:58 (laughs)

Harry Stebbings 36:59 Uh, by the way, I would not be the same. I'm, I, I dropped out after like three weeks. Two were freshers, where I was out of my mind drunk.

Stevie Case 37:06 (laughs)

Harry Stebbings 37:07 Um, I do not have any desire to go back. Life is good, baby. (laughs)

Stevie Case 37:10 (laughs) Hey, that's fair. Everybody's got their own goals. (laughs)

Harry Stebbings 37:13 Uh, we're h- how- uh, we gotta get back to hiring. How do I structure a process? Do I hire after one interview? Do we do case studies together, Stevie? How do we go through structuring hires for sales teams?

Stevie Case 37:26 Yeah, this is so tough, and I've seen it gone, gone wrong so many times. Uh, definitely not one interview. I think you need a number of perspectives.

Harry Stebbings 37:36 Mm-hmm.

Stevie Case 37:36 I think it's actually extremely valuable to get the perspectives of folks who are not salespeople in that process.

Harry Stebbings 37:41 Mm-hmm.

Stevie Case 37:42 Just because they haven't sold doesn't mean they don't know what good looks like. They've certainly been sold too, and I think that you've gotta have a combination of functional interviews, h- can this person check the basic boxes of doing the job, and then you've gotta get to the heart of what is gonna make them succeed. So you've gotta have like a dedicated... If grit is the thing, which it is for me, you've gotta have a full interview dedicated to testing for grit and hearing those stories. And the second one for me is curiosity, and in the sales cycle, what this comes back to is really discovery, but curiosity is at the heart of that hustle that it takes to learn and change with a business. It's also at the heart of closing really hard deals, because you've gotta do great discovery. You've gotta ask great questions. So for curiosity and discovery, I actually really love to do, uh, a case study, a role play, and get folks to walk through what it looks like for them to do discovery in the room. And this is often where I see that you've got a candidate who may look really good and they answer questions well one-on-one when asked directly, but you put them up at a whiteboard and ask them to do discovery in an uncomfortable situation, that's

Stevie Case 38:53 where a lot of them fall down.

Harry Stebbings 38:54 Can I ask, what does good discovery look like?

Stevie Case 38:57 Oh my gosh, it's dynamic. It's rooted in curiou- genuine curiosity. So bad discovery (laughs) looks like checking boxes, right? You might know the right framework. Uh, whether you're going through MEDDPICC or something else, you may have your list of questions. Bad discovery is checking the boxes of, of that list. Good discovery is really about curiosity and listening. It's about allowing the person you're asking questions of time to speak, and then rather than checking the box and then going to the next question, it's about looking for those nuggets that are gonna be the things you can put your hooks in that they care about to get your deal done. So you may have a, a 30-minute, uh, set of, you know, discovery questions and you're walking through that with a prospect. They might say one thing in that 30 minutes, and that's your thing that you're gonna tie your deal to, but you gotta be able to listen and like iterate and get to the heart of, what do they really care about? What are they trying to do? Why are they even talking to you?

Harry Stebbings 40:00 How do you know what's that nugget? How do you know what's that one thing?

Stevie Case 40:03 Well, you gotta be curious, and it's, it's gonna be custom to whatever your business is, and often that one thing is connected to why they're talking to you. Like what, why does this matter? Like people don't have... People are extremely busy. You know, everybody's on Zoom 24/7 now. Nobody wants to take an extra meeting. There's gotta be something compelling at the heart of why this person has agreed to spend time with you, and if you can deeply listen and understand what that thing is, and once you get ahold of it, then quantify it, you can keep coming back and use that as, as your hook to get your deal done. And maybe it'll be some kinda ROI they need to, uh, deliver. Maybe it'll be a problem they need to solve. But you've gotta get to that why at the heart of the thing.

Harry Stebbings 40:51 So we've gone through this now. We've tested for curiosity. We know that they're great at discovery. They've got grit. We wanna make them an offer. When it comes to like, you know, compensation packages for sales teams, what's your biggest piece of advice and lessons, and where do you think many go wrong? Again, I've never done this before, so- (laughs)

Stevie Case 41:09 (laughs)

Harry Stebbings 41:10 ... treat me like a simple person- (laughs)

Stevie Case 41:12 (laughs) You got it.

Harry Stebbings 41:12 ... if that's really hard to do.

Harry Stebbings 41:14 (laughs)

Stevie Case 41:14 (laughs) Of course. The key in these early stages, as you do want to bring on people that are amenable to risk, they have to be willing to take a little bit of a leap of faith, and I think this is where early founders can go a little bit wrong. They get bamboozled by a great resume, somebody who's coming from a bigger company, and that person is gonna want more guarantee of outcome. So they might be asking for more of a minimum guarantee, or a draw that is pretty lengthy, or reassurance that they're gonna make their variable compensation. Somebody who indexes too hard on those guarantees probably is not a fit in a startup. At the end of the day, what you want out of a great comp plan, um, early days as a founder is something that is so clear that if a salesperson reads it, they understand exactly what they should spend their time doing when you're not in front of them.

Harry Stebbings 42:07 Mm-hmm.

Stevie Case 42:08 And ultimately, that's what a comp plan is. Those are your marching orders. That is your job description for a salesperson. And if it's not aligned, if you build a comp plan that isn't clear or incentivizes them to do something else, you're not gonna get the results at the end of the day. People are very attuned to what those things drive, and you know, because startups are very dynamic, the important other side of that is you've gotta be willing to iterate on it. You've gotta be willing to work together with the salesperson to talk about what you're incentivizing them to do, understand their feedback on if that makes sense to them, if it's aligned with what they are thinking it means they should accomplish, and then you gotta build it together.... and let go of traditional ideas of what a comp plan is supposed to be, and really just focus on those incentives and the outcomes you're trying to drive.

Harry Stebbings 42:57 A- as a sales leader today, we're looking at a, a different 2023. How do you think about managing morale around sales comp in your team when people are going, "Oh, shit. What if we don't sell as much, and what if comp isn't where it was last year?" How- how do sales leaders manage that?

Stevie Case 43:14 Yeah. I mean, there's- there are strategic things and there are tactical things. I think strategically, you have to be really honest with the team, and you cannot make false promises. Nobody knows what the world is gonna look like over the next 12 months. We know it's probably gonna be rough, but we don't know exactly what it's gonna look like. And I think being honest about that and, uh, really getting a team on board and bought in on the mission of what you're working to accomplish, and building trust with them in that environment that you're gonna do right by them, and as long as they're doing the right things, that you're in it together, I think that is really number one. And then tactically, it- we've got all kinds of levers as sales leaders, and while we enter tough environments and things may be dynamic, you've got to find ways to identify the wins that underlie the big numbers. So when you're in a situation, which everybody at some point in their career is gonna be, where reps are not hitting the top line number, I think you've gotta look for ways to incentivize them to get other wins that matter, whether that's spiffs or other mechanics or gamifying the experience, and you've gotta go further back in the funnel. So an example of this would be if the team's not making the top line number, and your diagnosis is they're not outbounding enough, well, nobody loves outbounding and you can hound them all day and you can do a spiff to say, "Oh, anybody who does, you know, drive more revenue gets a spiff." The better thing to do is to go back to the basics of what is the first thing they have to accomplish to succeed at this? Build spiffs and a game around those first things, around the activities, around the first things you know lead to revenue, and incentivize them there so they can get an early win.

Harry Stebbings 45:02 I mean, (laughs) a- a spiff in the UK is, is, is generally cannabis.

Stevie Case 45:08 (laughs)

Harry Stebbings 45:09 Um, what- what's a spiff in your world? (laughs)

Stevie Case 45:12 A spiff is- very different, very different, hopefully. Uh, it's a special incentive. So essentially-

Harry Stebbings 45:18 Oh.

Stevie Case 45:18 ... it is an incentive outside of the typical compensation plan, and spiffs are generally rolled out with a limited timeframe around a specific unique goal. So people will do spiffs around end of quarter, or they might do a spiff around a specific activity. So it may be that, you know, you've got a quota and you're executing against a revenue quota, but maybe at end of quarter, we want people to do a specific kind of deal in a specific vertical. We may say, "Every deal that comes in, you're gonna get a 1.5X multiplier on those deals in that vertical."

Harry Stebbings 45:52 But the spiff always has to be tied to revenue, correct? It couldn't be tied to outbound leads?

Stevie Case 45:57 It can be tied to anything, and I think it should be tied, in many cases, not to revenue. The, the quota in the compensation plan should address revenue. A spiff is gonna work best when you tie it to something else that might not be directly tied into how they're incentivized in the comp plan, but it's something you need them to do and is important to the business.

Harry Stebbings 46:19 What's an example of a spiff? Is it, like, cash? Is it, like, a day away? Is it, like, a massage? And two, do people really give a shit unless it's cash?

Stevie Case 46:27 Generally speaking, I am a fan of cash for spiffs-

Harry Stebbings 46:31 (laughs)

Stevie Case 46:32 ... but any, any of those things. You can do it any way you want. The other things I think do work are things that involve recognition. So I like to do spiffs that are if you win, you get dinner, uh, you get to go out to dinner with the CEO and have kind of a special session, or you get special access to somebody. And it's that kind of leaderboard aspect of competition that you wanna drive 'cause you also want it to be fun. Like people wanna come out on top.

Harry Stebbings 46:59 Yeah.

Stevie Case 46:59 So one of the, one of the most successful, uh, programs I've ever run around this was trying to drive outbound on my mid-market team at Twilio, and, uh, we did a, a whole week of activities, called it Pipe Hype Week. And we really just wanted them creating pipeline, going outbound, and came up with a gamified version of Pipegen so they got points for... You get points for a certain kind of outbounding, you'd get points for creating new contacts in CRM, and it was all these activities that lead to opportunity. And so at the end of the week, they scored themselves and they turned in their score sheet, and the top prize winners got cash in that case. And then we also had some other fun prizes that went along with it.

Harry Stebbings 47:42 I love that. I think that's a great idea. Uh, going back there, you mentioned, like, effectiveness, and spiffs can help effectiveness. If we're actually just looking at new hires, going, "I don't know if they're any good," the

Harry Stebbings 47:54 hard thing with enterprise, I always find, is the sales cycles are so long. How do you measure effectiveness of new hires when the sales cycles are so long?

Stevie Case 48:03 In those cases, you really have to have someone engaged with that salesperson that knows what good looks like, that can weigh in on whether those deals are progressing or not. Because what can go wrong when you've got a long sales cycle, if you just leave a salesperson to their own devices, some will report out accurately on deal progress and some will report out very inaccurately. And the most common thing that happens is you'll hear from that sales rep, "Oh, we're making great progress. We're aiming towards a signature by Q3." And then you get to Q3 and you'll talk to the sales rep and they'll be like, "Oh, actually I haven't heard from them in 60 days." (laughs) It would be like, "Oh, the whole thing fell apart." And that's unfortunately very common, and whether it's the founder or a sales manager, someone has to be close enough to the work of that salesperson to understand and deeply inspect the deals and know if they are progressing.... and if you can analyze that, that will tell you, is this person on track? Are they getting it? In enterprise cycles, things can happen. They can fall apart at the last minute. Somebody who knows what's up needs to be close enough to diagnose.

Harry Stebbings 49:15 Things can fall apart in the last minute. I'm on many boards, and the most common thing that I hear, Stevie, and I want your advice 'cause I don't know what to say to this one, you know, "It just slipped to next quarter. It was so close, but it's just slipped to next quarter." And I n- I'm like, "Did it? O- okay?" I'm, I'm not sure. Wha- how would you respond to that if you heard that from a founder?

Stevie Case 49:36 So many great salespeople suffer from this, and ultimately, this is a failure of discovery. When this happens, you can almost always trace it back to the beginning of the conversation in that deal and a lack of understanding of some key factor. Some dots did not get connected early on, and that either that founder or that salesperson doesn't have a full grasp of if this matters to their buyer and why, and when that happens, you get in these scenarios where it's like, yeah, they're saying good things. It feels like it's gonna happen, but you haven't actually nailed the mechanics of a closed plan and an understanding of all of the factors happening inside your buyer's business. And that, that is, uh, like the one symptom you'll see in so many... it's true for enterprise salespeople too, is you'll see deals slip. It's like, "Oh, well, they're, they're missing something in their discovery."

Harry Stebbings 50:34 Mm. That's, it's the most common thing I hear. You also said things fall apart often at the

Harry Stebbings 50:40 end of quarters. One thing that we see often is discounting. How do you feel about discounting to get deals done?

Stevie Case 50:46 You know, it really depends on the circumstances and what you're trying to achieve. I'm definitely not against it. I, I think that, you know, there's so much urgency you can create at the end. If discounting is your only strategy, then you're in trouble. (laughs) It's not a great sign if your, your one go-to is, is discounting. But it can, it can really matter, and you know, I think back to one of the first big deals that I did at Twilio, and it was, uh, with a major US airline, and it was one of our first kind of Fortune 500 deals, and we got, uh, close to the end of this deal, and we had pitched to them a product that was really like a bundle of features that hadn't existed before and didn't have a price on it, but we bundled it up, and we said, "Okay, it's $15,000 a month." Like, random made-up number. (laughs) Like we just were sort of like, "We know you need all this stuff. These are enterprise features. It's 15 grand a month." And in the end, we pushed them to get the deal done at the end of Q4, literally on December 31st, and we ended up offering them a discount on that $15,000-a-month bundle, and w- we gave them, like, you know, uh, a 15% discount, and in the end, that discount pushed the deal over the edge and procurement got it done at, like, 4:00 PM on December 31st. Like, it's free money. That package didn't even exist before. And if you can do discounting that way, it can be really powerful, but you've got to understand there are so many other levers to create urgency, and you know, you, there, it's terms, it's pricing, but it's also, like, the risk and attention of not getting it done.

Harry Stebbings 52:26 I, I totally agree with you. I think there's two, uh, like, speaking of risks and not getting it done, two more things before a quick fire. One is, like, we're seeing multiple buyer infringements, I'm calling it now, which is like in a much more capital constrained world, the CFO's role is much more prominent in all buying decisions. How does that change your role today s- leading sales teams and educating sales cycles?

Stevie Case 52:51 The most important thing in an environment like this is that your sellers pull those people into deals much earlier. So, the junior seller's approach in these kind of environments is, "I wanna avoid the CFO at all costs." And like in the world of Vanta, "I wanna avoid the key decision maker. I wanna avoid the CISO."

Harry Stebbings 53:10 (laughs)

Stevie Case 53:10 "Wanna just, like, keep it to my champion. Uh, he says we're gonna get it done. We're just gonna, like, barrel through and get it done." That's how you end up with deals that fall apart at the last minute and slip at the last minute because you did not uncover all of the possible requirements and objections, and to do that, you have to get multi-threaded. So, the earlier you can go multi-threaded and give your champion an excuse to bring in a CFO, their head of security, all the folks who might object, it gives you a chance to work through those objections early and set your champion up to help get the deal done and look like they've got it together. (laughs) You know, you're putting them in a bad position if you don't help them bring that CFO in earlier. You've got to go at it head-on and make the case. That is the only way to win in an environment like this where you're gonna have these last-minute objections show up. So, you gotta discover the whole landscape.

Harry Stebbings 54:02 Totally agree in terms of making them your champion. Final one. We're also seeing people wanting to see the value a lot more, especially on renewal. Are you changing the structure of your org to essentially equip these people in your customer bases with the data that shows how powerful Vanta is? 'Cause now they want it. Before, it was like, "Renew." Now it's like, "Well, show me. Show me the ROI." Do you have to change what you do to tailor that?

Stevie Case 54:30 Yeah, we, we do a little bit. And look, at Vanta, we do value-based selling. We are talking in every conversation with our customers about those value drivers, and to date, our number one value driver has been growth. It is if you get that SOC 2, you prove you're HIPAA compliant, that's gonna unlock more revenue. It's gonna allow you to get deals done faster in markets you couldn't access before.The thing that does have to shift as we move forward now in this new environment is that the value drivers that matter are a little bit different. So, we're gonna have a little more emphasis on cost savings, and efficiency, and yes, growth still matters, everybody's still got to grow, but it's a flipping of that cost savings and risk reduction from the bottom of the list to the top of the list. So-

Harry Stebbings 55:20 Yeah.

Stevie Case 55:20 ... nothing really changes about how we sell or how we present our value props, but we are emphasizing other values of Vanta so we can help our customers get compliant much more efficiently, with less spend and less time.

Harry Stebbings 55:35 I feel for you. Your messaging has to permanently change. For VCs, the messaging is, "It's always a great time to invest." (laughs)

Stevie Case 55:42 (laughs)

Harry Stebbings 55:42 It's very simple. Uh, but, uh, I w- I want to move into a quick fire round now, Stevie.

Stevie Case 55:46 All right.

Harry Stebbings 55:46 So, I say a

Harry Stebbings 55:47 short statement. Sound good?

Stevie Case 55:48 G- sounds great.

Harry Stebbings 55:50 So, tell me, what sales tactics have not changed over the last five years?

Stevie Case 55:54 Ultimately, sales is the same it h- as it has always been. It goes back to the Rudnitsky playbook, people buy from people. They want to have an au- authentic experience that is rooted in real value. That will never change.

Harry Stebbings 56:10 What sales tactics have died a death?

Stevie Case 56:13 Ugh. High volume, cold outbound at scale. It just-

Harry Stebbings 56:19 Mm-hmm.

Stevie Case 56:19 ... is brutal. You've got to personalize. People are constantly hit from every angle, you got to give them something meaningful.

Harry Stebbings 56:28 What is your single biggest challenge as CRO today?

Stevie Case 56:31 Adapting to unknown conditions, and doing that with enough foresight that I don't have to change course quickly. It's the, the, the, the pace of change is so rapid, but I need to plan a year out. It's the hardest thing.

Harry Stebbings 56:50 It's also like, how do you plan resource allocation for an unknown destination? It's like-

Stevie Case 56:54 Yeah.

Harry Stebbings 56:55 ... do you, do you cut things massively and then overcut? And then that's not good. Or do you undercut and then have to do multiple? Well, that's not good. Basically, it's fucking hard. (laughs)

Stevie Case 57:04 It's so hard.

Harry Stebbings 57:05 (laughs)

Stevie Case 57:05 There's so much change and, and who knows? You know, the, we, we might be in for a mild recession, we might be in for a very significant recession, and I've got to put forward an annual plan that would accommodate either of those things.

Harry Stebbings 57:19 December next year, are we gonna be in a better or a worse place?

Stevie Case 57:23 Plan for worse, be prepared

Stevie Case 57:26 for better.

Harry Stebbings 57:27 I like that. I like that. Always plan for worse.

Stevie Case 57:30 (laughs)

Harry Stebbings 57:30 Uh, suing your high school, not normal, Stevie.

Stevie Case 57:33 (laughs)

Harry Stebbings 57:33 Why? Why? (laughs)

Stevie Case 57:35 (laughs) Yeah, there was another, uh, uh, random Stevie backstory. Uh, so I sued my Kansas School District because they banned a book. You know, I w- I grew up in Kansas outside of Kansas City. The, uh, school board banned a book because it was an award-winning book, but it had homosexual theme and I did not feel that was either right or constitutionally correct. And it turns out that the, uh, Federal Circuit Court agreed with me and I won my case against the school board. They had to put the book back and, and pay the, uh, legal fees.

Harry Stebbings 58:10 You are such a rockstar. (laughs)

Stevie Case 58:12 (laughs)

Harry Stebbings 58:13 Um, tell me, what one piece of advice would you give a new sales leader joining a new role today?

Stevie Case 58:18 Oh my gosh. Ask all the questions. No question is stupid. Ask everyone questions, get

Stevie Case 58:25 time with your executives, proceed without fear.

Harry Stebbings 58:29 What would you most like to change about the world of sales?

Stevie Case 58:32 Oh, I'd love for it to just be more human. Higher empathy. You know-

Harry Stebbings 58:37 Mm-hmm.

Stevie Case 58:37 ... it's still so aggro in so many corners, and I think that there is a world where folks can be extremely successful in sales

Stevie Case 58:49 and also kind.

Harry Stebbings 58:51 Tell me, final one, what one company sales strategy have you been most impressed by recently?

Stevie Case 58:57 Oh, Clari. I just bought Clari, and the sales experience is the best I have had. I think selling to salespeople is incredibly hard and the way-

Harry Stebbings 59:10 Why was it so good? Because Maggie Hot said it was amazing too.

Stevie Case 59:14 I love Maggie.

Harry Stebbings 59:14 Why was it so good? You have to tell-

Stevie Case 59:15 Maggie's a rockstar, number one, and she knows everything. She's just a, an absolute queen. Um, Clari's sales process is very human. It's very high quality. Every touch is quality and thoughtful. And my sales rep engaged with me as a human being. He didn't just cold outbound me. He, uh, tactically, for salespeople, he commented on my LinkedIn posts in a human way. He engaged-

Harry Stebbings 59:41 Mm.

Stevie Case 59:42 ... me as a person and it made me want to help him win, and it made me want to help him get the deal done. Of course, the tool had to be amazing, there had to be all the value there, they had to prove that value. They showed us so much value before we signed the deal, and then they gave us a great offer we couldn't refuse at the end of the quarter, and we got it done. Even though we had a budget freeze, we bought it.

Harry Stebbings 1:00:04 I love that. I, I think that's awesome. Um, that's so good to hear. Stevie, I love doing this. Thank you so much for being so great on the show. You are a star and I've so enjoyed having you on.

Stevie Case 1:00:15 Ugh, thank you for having me. It's been a blast.