The Exchanges

Q That's really interesting because that feels like a little kind of toe in the water test to see if it worked. But I always hear the, you've got to be fully committed to enterprise or fully not. And I'm like, oh, that sounds quite scary. Do you not have to be in for founders listening? Can you test it in a more gradual way?

A 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. It wasn't necessarily to cut over from SMB to suddenly we're going to go do deals with companies, 5000 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 toe in the water about it is that I actually pulled the 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 going to 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.

AI assessment note: “You can test it with the caveat that these things are radically different.”

Q I mean, three boys, and then the first, like, hey honey, it's twins. Oh, yeah. And I thought sales quotas were nerve-wracking in twenty-twenty-three, and that's another thing. Uh, we'll get into that. That's fascinating. Well done, Julie. Um, Stevie, we're going to start with you on a really tough question, which is, How have you navigated your growing career while also growing your family?

A Well, the honest answer to this is, is very poorly at first, and it was really painful in the early days. You know, my daughter is 18 now. Uh, when I had her, I was in product, so I was still on the product side of the house, and I made the transition to sales when she was around two, and at that At that point, I got out on the road with her, and one year later, when she was three, I became a single mom with full custody, so I was navigating trying to be an AE and figure out how to parent this kid at the same time, and it was ugly. Like, I have distinct memories of doing a demo while I was driving her to daycare, and she was crying in the backseat, and I'm trying to, like, explain features, and I'm in the, the, the, uh, driveway at Wendy's trying to get her a Frosty and, like, muting in between explaining features. Like, it was ugly. I did not have resources at that point in my career. I couldn't outsource stuff. I didn't have a lot of help, and that brings me back to the highlight, which is I was forced to get super focused. So when I was at work, I was 100% at work, and when I was at home with her, I was 100% with her, and I used to think about it as almost just looking at the The road right under my feet, and I would only focus about two feet out in front of that. That's all I could do, and it's gotten a lot easier over time. Thank goodness. Life has definitely become a litt…

AI assessment note: “I was forced to get super focused. So when I was at work, I was 100%”

Q I mean, three boys, and then the first, like, hey honey, it's twins. Oh, yeah. And I thought sales quotas were nerve-wracking in twenty-twenty-three, and that's another thing. Uh, we'll get into that. That's fascinating. Well done, Julie. Um, Stevie, we're going to start with you on a really tough question, which is, How have you navigated your growing career while also growing your family?

A Well, the honest answer to this is, is very poorly at first, and it was really painful in the early days. You know, my daughter is 18 now. Uh, when I had her, I was in product, so I was still on the product side of the house, and I made the transition to sales when she was around two, and at that At that point, I got out on the road with her, and one year later, when she was three, I became a single mom with full custody, so I was navigating trying to be an AE and figure out how to parent this kid at the same time, and it was ugly. Like, I have distinct memories of doing a demo while I was driving her to daycare, and she was crying in the backseat, and I'm trying to, like, explain features, and I'm in the, the, the, uh, driveway at Wendy's trying to get her a Frosty and, like, muting in between explaining features. Like, it was ugly. I did not have resources at that point in my career. I couldn't outsource stuff. I didn't have a lot of help, and that brings me back to the highlight, which is I was forced to get super focused. So when I was at work, I was 100% at work, and when I was at home with her, I was 100% with her, and I used to think about it as almost just looking at the The road right under my feet, and I would only focus about two feet out in front of that. That's all I could do, and it's gotten a lot easier over time. Thank goodness. Life has definitely become a litt…

AI assessment note: “I was forced to get super focused. So when I was at work, I was 100%”

Q to pass it off as my own quotes. And then they told me that they were an English student and that it was Maya Angelou's. And I told them, well, that's venture capital. We package other people's knowledge and set it as our own. So that's lesson one. Nah, uh, didn't go down so well. Um, anyway, uh, Stevie, who, who was your shining light in terms of this mentor?

A I have been so lucky on this front. I mean, Matt Golden was the first. I would have never been in sales without his willingness to take me on and teach me how to sell. But really, the transformative moment for me was at Twilio, and Allison Welch was a big part of that, but it was also that I had an entire reporting chain that included, um, all parents. So Allison reported to the CRO, Mark Boroditsky, he had kids. He talked about them very openly. George Hu, our COO, had kids. Jeff Lawson, the CEO, would talk about his kids. So there was this real commitment to talking about family, and that just became part of the practice, and Harry, you asked if that question you had asked in opening the door for your team was okay, and the answer is absolutely, but the key is turning it into a practice, and that's what happened with all those leaders for me at Twilio, is it was just part of the daily The daily everything was just like, oh, I'm picking up my kids now, or I'm taking off next week to go skiing with my daughter, or, you know, just celebrating life moments. And, you know, Ari, you may not realize this, but the way you include your mom in your story, the way you talk about your mom, it actually gives parents more comfort and permission to talk about their kids, because it's this little signal that And we were talking earlier about that luxury or the privilege of being vulnerable. …

AI assessment note: “Matt Golden was the first. I would have never been in sales without his willingness”

Q 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. What drove you when you're 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. What drove you?

A Oh my gosh. A combination of stubbornness and desperation 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, I 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 in 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.

AI assessment note: “A combination of stubbornness and desperation and hunger to succeed.”

Q We're going to dig into each of those chapters. I'm just too interested. Do you think you lost the insecurity around people and the, um, uh, as you said, slightly withdrawn nature, or did you embrace it? And use it as a strength. Which one is it?

A Oh, I definitely did not lose it. I have embraced it. 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 me to say I'm an introvert. I don't think anybody 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 to the gates for me? And we were in a, uh, 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.

AI assessment note: “Oh, I definitely did not lose it. I have embraced it.”

Q 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?

A You know, it is really a fundamental shift in the story of the problems you're trying to solve. 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 up market. 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 to doing that 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.

AI assessment note: “we have to tell the story and talk about the value drivers in very different ways”

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 Mmm. It's, it's the most common thing I hear. You also said things fall apart often at the end of quarters. One thing that we see often is discounting. How do you feel about discounting to get deals done?

A You know, 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. 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 with a major US airline, and it was one of our first kind of Fortune 500 deals, and we got 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 dollars a month. Like, random made up number. Like, we just 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 Q four, literally on December 31st. And we ended up offering them a discount on that 15,000 dollar a month bundle. And we, we gave them like, you know, a 15% discount. And in the end, that discount pushed the deal over the edge and procurement got it done at like four 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, b…

AI assessment note: “I'm definitely not against it. I, I think that, you know, there's so much urgency”

Q Mmm. It's, it's the most common thing I hear. You also said things fall apart often at the end of quarters. One thing that we see often is discounting. How do you feel about discounting to get deals done?

A You know, 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. 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 with a major US airline, and it was one of our first kind of Fortune 500 deals, and we got 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 dollars a month. Like, random made up number. Like, we just 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 Q four, literally on December 31st. And we ended up offering them a discount on that 15,000 dollar a month bundle. And we, we gave them like, you know, a 15% discount. And in the end, that discount pushed the deal over the edge and procurement got it done at like four 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, b…

AI assessment note: “I'm definitely not against it. I, I think that, you know, there's so much urgency”

Q We're going to dig into each of those chapters. I'm just too interested. Do you think you lost the insecurity around people and the, um, uh, as you said, slightly withdrawn nature, or did you embrace it? And use it as a strength. Which one is it?

A Oh, I definitely did not lose it. I have embraced it. 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 me to say I'm an introvert. I don't think anybody 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 to the gates for me? And we were in a, uh, 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.

AI assessment note: “Oh, I definitely did not lose it. I have embraced it.”

Q 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?

A You know, it is really a fundamental shift in the story of the problems you're trying to solve. 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 up market. 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 to doing that 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.

AI assessment note: “it is really a fundamental shift in the story of the problems you're trying”

Q 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, fuck. Why when it was working so well in SMB and startups?

A 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, 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 AB test and right out of the gate, they killed it.

AI assessment note: “the truth is we are being led there as a business.”

Q have been that honest. Um, I wonder why I'm single. I would never have been that honest, um, when I was not so successful earlier in my career. Now I'm like, oh, fuck it, if you like me or not. Um, you're a rockstar CRO, you're a leader of your profession. Is it a luxury of being successful that we can be, and it's seen as a strength almost? Yes.

A It's a luxury and it's a privilege. And I think there are a couple of things I would call out in there. One is I, you never really feel like you've made it. I think there's a certain sense you can always look at other people and see, oh, they've made it more than I've made it, or I haven't really made it. I'm still climbing. So part of that is the perception you have of your own success. You can give yourself permission to be more real earlier. Rather than holding the bar for some like ridiculous accomplishment that you have to achieve before you're able to be real. And I think it's incumbent on those folks who have reached that point in their career and have the luxury and privilege to give everybody around them that permission, because you can actually open it up for other people. You can open up an environment where people allowed to be human and make mistakes and be real. And I think that that's what leadership really looks like in the workplace. Now, like that is the bar for being a great leader. It's not just leading your team to victory. It's doing that and respecting the humanity of the team you've built and allowing them to be real and human. You know, you list off those things, which it sounds like you think are deficiencies about you, Harry, but we all have those things. Like, I told my story in Vanity Fair this year. I had a lot of those things, and we're not alone,…

AI assessment note: “It's a luxury and it's a privilege.”

Q I want to touch on some inspirational stories, some anecdotes. Let's bring this to life. Stevie, there's no one better than an amazing story. I, I loved our episode so much. Uh, but I, I wanted to move to you. When we think about inspiring stories or personal experiences of like overcoming challenges related to balancing motherhood and your career, what's one or two that come to mind for you?

A Yeah, you know, it's so interesting because Jess really touched on this idea of that feeling of being fake at times and having to put on a mask and I really deeply struggled with that for years when my daughter was younger. I started this sales career and I already felt so completely out of my element. I had this weird gaming background and like all this backstory that I was trying to push As far away as possible. And then, but not only was I a mom, I was a single mom, and I just was do honestly doing everything in my power to hide it. And I would like do anything at work. I set no boundaries. If there was like a trip or an opportunity or something coming up, my answer was always yes. I never even hinted that I might have an obligation that could get in the way. Because I was so scared of the idea that I had a commitment at home, and I was working with all men, and I was like, it felt so unfamiliar, and even though some of them were parents, I just felt like a total outsider, but I doubled down on that myself by pretending it wasn't there. So I would literally, like, if I had to go on a trip, and I was a single mom, I would, like, fly people in from all over the country to watch my daughter. At one point, I flew Her mother-in-law in from Canada to stay with her, and like, I would never mention these things to, to the people I worked with, and it was so hard, and so isolating, a…

AI assessment note: “I was a single mom, and I just was do honestly doing everything in my power to hide it.”

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”

Q 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 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?

A Ah, 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 on sales. It's 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.

AI assessment note: “You can, but I would caution you against trying to do both right away.”

Q this now. We've tested for curiosity. We know that they're great at discovery. They've got grit. We want to make them an offer. When it comes to, like, you know, compensation packages for sales teams, what's your biggest piece of advice and lesson? And where do you think many go wrong? Again, I've never done this before, so treat me like a simple person if that's really hard to do.

A 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 going to 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 going to 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. 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 sales…

AI assessment note: “what you want out of a great comp plan, um, early days as a founder Is something that is so clear”

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: “it depends a lot on your ICP. I think that if you're going after enterprise”

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 That's really interesting because that feels like a little kind of toe in the water test to see if it worked. But I always hear the, you've got to be fully committed to enterprise or fully not. And I'm like, oh, that sounds quite scary. Do you not have to be in for founders listening? Can you test it in a more gradual way?

A 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. It wasn't necessarily to cut over from SMB to suddenly we're going to go do deals with companies, 5000 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 toe in the water about it is that I actually pulled the 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 going to 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.

AI assessment note: “You can test it with the caveat that these things are radically different.”

Q 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?

A I think the single most important thing in that is that that first sales 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 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 I like I've hired the 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 sales person 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 sales person in every conversation and not just sales conversations, let them listen to 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 nee…

AI assessment note: “first sales hire has to be glued at the hip with the founder”

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: “get to the heart of what are some of those accomplishments that person is very proud of”

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. It's about allowing the person”

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: “strategically you have to be really honest with the team and you cannot make false promises”

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 of that sales person to understand”

Q I, I totally agree in terms of really boiling down to math. Uh, we're gonna get into the math, uh, when we get into, like, a strategy discussion. I wanna just unpack a couple more parts of your life which are, you know, really important. You're also a single mother, uh, wonderful daughter. How has that impacted your approach to your sales career?

A Oh my gosh. It's, 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 event, and you know, I 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, a Wendy's 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 every day in this business. This is hard. And the bad days, the good days, the struggles, I just am so grateful fo…

AI assessment note: “for the first half of my career, it really just made me so much hungrier.”

Q 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 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?

A Ah, 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 on sales. It's 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.

AI assessment note: “You can, but I would caution you against trying to do both right away.”

Q 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?

A I think the single most important thing in that is that that first sales 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 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 I like I've hired the 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 sales person 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 sales person in every conversation and not just sales conversations, let them listen to 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 nee…

AI assessment note: “that first sales hire has to be glued at the hip with the founder.”

Q this now. We've tested for curiosity. We know that they're great at discovery. They've got grit. We want to make them an offer. When it comes to, like, you know, compensation packages for sales teams, what's your biggest piece of advice and lesson? And where do you think many go wrong? Again, I've never done this before, so treat me like a simple person if that's really hard to do.

A 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 going to 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 going to 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. 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 sales…

AI assessment note: “what you want out of a great comp plan, um, early days as a founder”