The Exchanges

Q 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? Because 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?

A 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 II, 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 going to 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 it 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.

AI assessment note: “Yeah, we, we do a little bit, and look, at Vanta, we do value-based selling.”

Q vulnerability that we see so much of today. I want to 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? Because it is a different background.

A 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 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, there was no going viral. It was all very, ah, 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. 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. And as long as you're always optimizing for that outcome, that's how you win.

AI assessment note: “there's so much in that that informs how I sell today, how I run teams”

Q Can I ask two-fold? The joy of this show is just like the randomness. Um, the joy, 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?

A 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 narrative. Don't hide that you have to take your kids somewhere. 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.

AI assessment note: “The single most important thing is don't apologize. Don't accept this narrative”

Q I've learned that it's really important to not be afraid to ask the stupid questions. When you say the revenue game, what does that mean?

A I mean, 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. If we're gonna, we, you know, IPO, we were two hundred million dollar run rate. And Jeff had set out this vision of we're gonna get to a billion dollar run rate. But then behind that, there weren't really, 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, it's about winning that revenue generating game. And how do you continue to make things go up into the right in a predictable way, not on hope. But something that you can control that's going to drive revenue up into the right.

AI assessment note: “what it really boils down to is the math behind success”

Q 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. 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?

A 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 see what you can drive. 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 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.

AI assessment note: “if you can add those two experiences together. And get a better outcome, then that's when”

Q idea of testing a little bit the expansion up. When we think about structuring our team moving from a PLG motion to a more traditional motion, I'm the founder, you're my angel investor and advisor. I'm thrilled to have you, Stevie. 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?

A You know, it depends a lot on your ICP. 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, a 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 and 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 going to make a 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.

AI assessment note: “if you're going after enterprise customers, you likely just need one to two really great enterprise salespeople”

Q 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?

A 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. I think with the 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, but 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.

AI assessment note: “I think there's a place for people who take orders”

Q 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?

A 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 want to see passion, you want to 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.

AI assessment note: “asking about those things, you want to see passion, you want to hear stories”

Q Can I ask what does good discovery look like?

A Oh my gosh. It's dynamic. It's rooted in curious, genuine curiosity. So bad discovery looks like checking boxes, right? You might know the right framework, uh, whether you're going through med pick or something else, you may have your list of questions, bad discoveries, 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 going to 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 going to tie your deal to, but you got to 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?

AI assessment note: “Good discovery is really about curiosity and listening.”

Q As a sales leader today, we're looking at a different twenty-twenty-three. 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?

A 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 going to look like over the next 12 months. We know it's probably going to be rough, but we don't know exactly what it's going to look like. And I think being honest about that and 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 going to 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. 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 going to be, where reps are not hitting the top line number, I think you've got to 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 got to go further back in the funnel. So an example of this would be if teams not making the top line number and your diagnosis is they're not outbounding enough. Well, nobody loves outbounding…

AI assessment note: “you've got to look for ways to incentivize them to get other wins that matter”

Q I love that. I think that's a great idea. Again, Bradley, 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 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?

A 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 sales person 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 Q three. And then you get to Q three and you'll talk to the sales rep and be like, oh, actually I haven't heard from them in 60 days. 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 sales person 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.

AI assessment note: “someone has to be close enough to the work... to understand and deeply inspect”

Q How do you know what's that nugget? How do you know what's that one thing?

A 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, seven. 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 kind of ROI they need to deliver. Maybe it'll be a problem they need to solve, but you've got to get to that why at the heart of the thing.

AI assessment note: “often that one thing is connected to why they're talking to you.”

Q Stevie, we said before the show, as I said, um, you know, my mother is, uh, going to learn gaming after hearing your episode. Still waiting, um, but I live in hope. Um, over to you. Bass, pardon, who are you?

A I love it. You gotta hook me up with your mom. We'll do a Zoom session. I'll get her started. It'll be awesome, and I think she'll love it. Uh, Stevie Case, I'm the Chief Revenue Officer at Vanta, and I'm also a single mom to an eight I have a teen-year-old daughter, and she is amazing. She's a senior in high school, so I'm definitely at the far end of the parenting spectrum in this group, and for me, the best part is really what started as the worst part, which was the forced intentionality and the focus that you have to have as a parent. I was forced to develop it as a single mom when she was very young, and now I think it's probably, uh, really, truly one of the superpowers that I've developed Because I'm a mom.

AI assessment note: “Stevie Case, I'm the Chief Revenue Officer at Vanta”

Q Yeah, no, I totally agree on people just wanting to be seen. Um, getting out of the rabbit hole, otherwise I could get on that a long time. I spoke to Christina as I said, she mentioned George Who before. Um, what did you learn from George at Salesforce that was really instrumental for you?

A 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 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 sales management and an IC role, and 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 Jeff 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 throu…

AI assessment note: “continued to like have my back and educate me about the next step”

Q minute. I'm on many boards, and the most common thing that I hear, Stevie, and I want your advice, because 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'm like, Did it? Okay. I'm not sure. How would you respond to that if you heard that from a founder?

A 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 factors. 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 going to 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 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.

AI assessment note: “ultimately, this is a failure of discovery. When this happens, you can almost always trace”

Q I think we need also other people to change, obviously also, uh, men who don't understand. 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?

A Yeah, 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.

AI assessment note: “step one is genuinely caring about the people that work for you and asking them”

Q I think we need also other people to change, obviously also, uh, men who don't understand. 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?

A Yeah, 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.

AI assessment note: “step one is genuinely caring about the people that work for you and asking them”