Uncapped #17 | Christina Cacioppo from Vanta

[00:00] No, you just have to like Stockholm syndrome yourself into being like, well, I used to be someone who likes to build products. But now I love building teams. And whether or not I identified as that person a few years ago, it doesn't matter. Now that's me. And I believe it, you know, and then like when it changes, you're like, now I'm this person. I love HR policy, you know, because that's what the company needs right now. All right. I'm here with Christina from Vanta and very excited for this conversation. Thanks for doing this with me. Thanks so much for having me. [00:30] probably as promising but also as competitive as they've ever been. There's a lot of ideas that seem very greenfield. And the result of that is there's tons of startups going at them. And so I think a very, very common founder experience today is you build a thing that makes a lot of sense and you look around you and there's 13 other companies also building something that makes a lot of sense. You've operated in a really competitive market for a really long time. And so I thought something founders could learn from you about would be operating a competitive market. So I want to start there. I guess the first place I wanted to go with it is... [00:59] the mentality, I think, that you've learned over the years that it takes to succeed. So can you talk a little bit about what's the mindset that you've gotten yourself to over the years? Yeah, for sure. And a bit of like very short version of the history, which is Vanta started in 2018. We were the first person who did what we did. We had about two years where our competitors were accountants and consultants. And when we were selling to founders and engineers, that was wonderful. Would you like software? Would you like an accountant? And then try to kind of keep it [01:29] got out and then

[01:31] In 2020, when everyone is at home board, lots of people started Advantage competitors. You did try to keep it quiet for a while there, right? We did, yes. And some of it actually was like, we know this is really good and we know people will knock it off. So how far can we run? And your mindset was basically just like, let's get as much traction as possible before people think that this is a good idea. Yes, because people thought it was a terrible idea. No startups got socked to. No one knew what, no one could spell it. It was just like, why are you like seemingly nice people working on compliance? Like what's like, do you need some help? [02:01] You should keep it a secret. Because when you talk to people, when you talk to founders who had this problem, they were like, I will pay you any amount of money and I will crawl through any amount of money for this. Wow. It's like, I really want this thing and I can't get it. And if you can get me there, I am all here for whatever you put me through. Were you getting customers with like a janky product? A hundred percent. Yeah. During YC, a YC company that bought Vanta called it the brutalist white website. Yeah. That sounds nice. Yeah. You know, that was, that was the brutalist white website sucked in a million ways. [02:31] Except it got people to their outcome. I guess you also had a very good why now, right? Like they're like a thing really happened. Kind of. Or like, yes. Or did that just seem that way? It just seemed that way. Like the why now existed in 2016, in 2014. [02:44] I think like why was it 18? And I think it was because generally if you said compliance to an engineer, they ran screaming from the room. So what was the first year it could have happened?

[02:52] 14, probably. 13, 14. So it was a reasonable thing, but it was like... But I couldn't give you up. A startup could have done it for a few years. Yeah. And so that's actually... I used to love the why now question, especially about that USV. You're like, oh, it's so intellectual. Well, I didn't know that there was that gap in time between... You're like, yeah, yeah, yeah. You're like, I only have four. I thought Vanta was the first one taking... which I guess you were the first one taking advantage of it. We were the first one. But like, someone could have. Yeah. There were a couple really manual solutions, but I think it was like lawyers looked at the problem. [03:22] it in just a different way than an engineer. Yeah. But like we weren't particularly smart. You know, it's like anyone could have figured that part out. They just didn't. OK, so you stayed secretive as long as you could. But then at some point you didn't. You weren't secretive. Yeah. Well, and the word kind of got out. And so and then we got this like host of knockoffs and. . . [03:38] You know, I think we went through like, oh, well, they're just knocking off for like, oh, they took screenshots of Vanta and sent them to a dev shop in Mexico and got the product back and then said Vanta took two years to build this. We built in two months. And like they suck and we're awesome. Is that how they said it? Yes. That was their voice. Yes. Very surfer bro. You know, we like went through the phase of like, well, that won't work or that's not fair. Like and I think the thing, you know, you learn is like all is fair and love and capitalism.

[04:08] and like customers, like customers are trying to solve the problem. Yep. And like, they don't care if you're first. They care if you're the best thing today. Yep. They don't care if, you know, you were secret shopped and someone took screenshots and like ripped everything off. There's no referees in capitalism. Yeah. And you kind of want there to be one, but like there's not. There's not. And I think you've got to stop searching for one. Did you have a thing switch for you? Like were you at one point looking for a referee and then you decided to stop? Yes. And then you're like, what am I, you know, like even like if I [04:38] what would i con like what with the referee and you're like i don't know you know right um i think you see you see investors fund these like investors don't care and you're like kind of take it personally and then you're like you know it's like not it's capitalism like it's not personal yep and so i think the the switch was eventually it's like cool we started this thing but again no one cares i'm also kind of trying to de-emphasize that i mean it's important internally but it's also not or not to not like rest on your laurels way yeah like i think a lot of why i do and a lot [05:08] go to the last thing you shipped. And so it's like, okay, cool. What have you shipped for me lately? And that's how customers think, and that is great and terrible, but like... [05:16] also reality. And so you just got to go with that. Yeah. What else from a mindset, you know, [05:23] perspective did you end up building over time besides like all's fair and love and capitalism, which I think is like very that is like hard, hard-earned wisdom. But what else came to you over time? [05:33] Shipping velocity. Because I think also, you know, then the Vant, and even the Vant of like a pre-competitive era, we like tried to get stuff right the first time. And so we'd write these long specs and do all this work and then like take a long time to ship something. And then it was wrong.

[05:48] And not, you know, through anyone's fault. It's just usually the first thing you put in front of a customer is in fact wrong. But we would like had spent six months on that. Right. [05:56] And then we get this kind of negative feedback and then I'm just like very demoralized. [06:01] And then customers are like, what have you shipped for me lately? Like nothing. Yeah. Right. And so trying to get to like the frame, and I feel this way in my career too, it's like I very rarely, if ever, ship the right thing the first time. But I can usually ship the right thing by like the fourth time. Yeah. And so to the team, it's like how do you minimize the time between, you know, the zero width and the fourth shift? How quickly can we get to V4? Exactly. Yeah. And like V4 should be right and I'll hold you to that. But V1, like... [06:27] V1 does not have to be right. And like trying to switch that mindset, because I think we had a lot of people who are, you know, like good students and done one in school and want to get it right on the test and get it right the first time and feel bad. And you're like, no, no, no. Like that's [06:38] the mental model of school, but actually not to real life. Totally. And trying to like flip that to competition is one of the like more psychologically vexing parts of a startup. Yeah. Do you try to minimize how much you think about it or how much your team thinks about it? Like what's the what have you tried to cultivate for yourself, your exec team, your broader team about competition? I think there is. And this works kind of [07:04] Sometimes well and sometimes not. But I think for me, what I... [07:06] What I try to do is like... [07:09] If a competitor is just copying, like, fine. But also there's a little bit of, like, how can we use that to our advantage? And we have in some ways where we're like, we're going to call this new field this. And, like, everyone's going to call it and, like...

[07:19] Have we created a category now? Right. Like there's there's parts you can kind of weaponize for yourself. Yeah. The other part is to do something different. Yeah. Why? And I think it's trying to start from the like assume they're smart, not like assume they're idiots. Yeah. And like, what do they know that I don't and try to figure that out? And again, maybe you conclude they know nothing you don't and they're idiots. [07:38] But like, I think it is always a useful thought exercise, even if you've dismissed them the last 10 times on doing like this. Have you had to go the other way where you've ended up cloning something from a competitor? Because, yeah, they figured something out good. Yeah, actually, there was a bunch of one of our early competitors was really good at talking to our customers and finding out the parts of the product they didn't like it fixed them. It wasn't particularly brutal, honestly, because it was like, oh, yeah, they just listen to our customers better than we did. And so that we're like, OK, like that needs that needs to stop right now. [08:08] Yeah. Yeah. Have you learned anything about how to do like the go to market side in a competitive market, whether it's like the way you, you know, position at the top of the funnel? I mean, like you had I think you've been running the like compliance that doesn't talk too much billboards for a long time. That's still like the best billboard I've ever seen. Saster 2021 was its debut. It's crazy. Yeah. Keep it going. Yeah. Yeah. That billboard's locked up for 10 more years. Like kind of actually. I love that. Yes.

[08:38] Most markets are really competitive, but like, what have you learned? Yeah, I think one bit is like [08:42] Man, AE confidence is so real and not as rational as like an EPD person, like an engineer or PM would imagine. And that works on the way up and it works on the way down. When the team is starting to lose confidence, like you got to go fast and you can't just go in with logic. And I think we messed that up for a while. And it works on the way up too. But then it kind of becomes this like, how do you build confidence amongst your salespeople game? How do you build it? What we did, and this is all credit to our CRO, Stevie. [09:11] was one of our issues with early competitors was they were actually so good at like secret shopping Vanta and like maybe exfiltrating, you know, like they just like knew everything. [09:21] And we knew very little. And I think we were also like very Midwestern, like, oh, but we're nice. And isn't it, you know, and like not not good at competitive intel. And so the way we solved that was we put one or two people on every competitive deal and they just like listen to all the call or like they were in all the calls. They talked to all the customers. They talked to like customers in both directions. And they just got smart about what was going on. And they figured out the talking point and the weak points and all of that. [09:51] And it was one or two people. And then we started adding them to everybody else's calls. And then like AEs would be like, oh, I want that person to come join. To show the confidence. Yeah. Exactly. And like when I add them, I win more. So like definitely want them in. Yeah. And then that like sort of us most out. That's brilliant. There's also honestly probably something there is we tried to do all this enablement with like enablement people and PMMs and me and PMs. None of it works. Like, I mean, it works and everyone tries really hard. Yeah. But like salespeople learn from salespeople and everyone else is, you know.

[10:20] Not as good. It doesn't matter who you are or what you're trying to do. Yeah, totally. I want to go over to fundraising. I guess you started fundraising at your seed in when was it? 2018? Is that right? April 18. April 18. You then, I think, if I recall, had like a lot of investors who wanted to talk to you over a period of time between then and your A. Yes. Can you just talk about like some of the stuff you did? I know we've talked about this before, but can you talk about in that period how you made most use of that time? [10:50] only took money from seed funds. The thinking was, or like, don't take money from anyone who will write an A check because we did the like post YC, you know, raise your seed round in six days. Yep. Crazy thing. And didn't want to choose a board member. Like that just felt silly. Board members are like harder to get rid of. Yep. You know. [11:08] execs, co-founders, right? Like, you'd be thoughtful about that decision. And then I did a, I can't remember who told me to do this, raised a seed round, then went around to all the [11:16] a firms and we're like hi just interesting we just raised no opportunity for you here just want to say hi and like [11:23] Put the first dot on the map. Like right after the round? Right after the round. Within weeks kind of thing? The one week. Wow. It was like schedule all of them, but just schedule them after it's done. Wow. Someone gave you advice to do that? Yeah. And it's like putting myself on the map, you know, nothing for you now, but like, here you go. I love that. It also creates a very low stakes conversation where nobody is thinking like that they can ask you about certain, like you just can control that conversation so easily, I bet. Yes. So did that. And then it was like,

[11:51] I honestly, there was this moment of like, shit, we just like raised $3 million to do all this stuff. And we have, you know. [11:57] two people sitting on a couch. Like, we gotta get hopping. So there was something that had just said. And then at some point... [12:03] six months later, you're like, okay, this is work. Like, this is different. Banta feels different than literally everything else I've worked on in my career. It is a true, like, pulling, like, the market is pulling something out. Mm-hmm. [12:16] There's a million things wrong and a million things going on, but like there's something here. And then... [12:21] Did not really talk to VCs. I think what started happening was there was like some amount of word of mouth among San Francisco founders about like, hey, if you want this Sock 2, there's this Vanta thing. We had this call response of like Sock 2 Vanta going. [12:34] it would start to come up with these companies, VCs. They would start to talk to us. [12:40] And look, it was like half I was playing a game and half. [12:43] It was actually really busy. But I generally reply and be like, look, I am just too busy fielding customer calls. Yeah. [12:49] Blake, I don't have time to meet with you. [12:52] But it sounds like you know, you know, [12:55] this founder at this company, you can go talk to them. Yeah. And like, look. An existing customer. An existing customer. Yeah. And look, the thing, you know, I'm trying to do is grow the business. And so if you have referrals for me, I mean, of course, I'll take them. [13:09] But like then go talk to them, talk to them about the sales process. If they buy, if they don't buy, talk to them about the process. Right. Like that is better diligence and information that I could ever. Yeah. If you want to see if Vance is good, go try to send us a customer, see if they close and then see if they're happy. Yeah. And it's like that is better than anything. And that happened. Amazingly. So that worked very well. Yeah. You know, and I do think there was like a game, but I kind of call it a game because I've been like, oh, no, sorry. I'm just too overwhelmed by like, you know, customers and dollars. And there's an implied dynamic in there of if you want to get time with me, send me a lot of customers. Yeah.

[13:39] And you have to kind of be careful to not sound like a total jerk. Yeah. Because I think you can very easily go to jerk territory or like, especially if your thing isn't working. You know, it's like they send you a bunch of stuff. Yeah. Well, part of why that thing works is because that's an incredibly confident dynamic for you to be running. Yes. Yeah. Which helps. Which helps. And I think, you know, I think one of my pieces of advice for founders is investors... [14:02] are not people you should seek approval from. They want to back people who are confident in what they're doing. Yeah. Not people who are seeking their approval. And it's really hard. There's a real dynamic where founders want investors approval. Yes. Particularly early because I think like, at least in my experience, it was like before I had real customer traction, you're like, well, at least investors, you know, think that this is worth backing. So that gives me something to hold on to. Yes. And whereas I think, and I think I just like, well, got lucky in lots of ways, but got lucky because early in my career, I worked for really good early stage investors and I kind of saw these pitches. [14:32] and be like, oh, no, this is not compelling. You want to back the person who like believes in where they're going and that might change a million places, but can put one foot in front of the other and not look up and be like, is this right? Am I on the right trail? And so then I think it's like, OK, as a founder, how do you get that? And some people can just manifest their confidence, which is great. I'm very jealous of and I've always been like need to figure it out and do it to get confident. But like it sort of doesn't matter. It's like as long as you are you are

[15:02] are like much more compelling to investors. But, you know, they should also just be like much more compelling to customers and like building said business. So what ended up happening at your Series A or the round when you picked a board member? Yeah. So it was that one. So there was this whole, you know, had this whole framework on how we choose a board member and like did reference calls for people. And I had this spreadsheet. And I remember I did some of them over the holidays because it was like, [15:27] Customer-thorne email. Like, I just had time, more time. And had this whole thing... [15:31] And then literally ended up choosing an investor in Boardman. I remember who wasn't on the spreadsheet. I fell off the framework. How'd that happen? I was not going to talk to Sequoia. Mm-hmm. [15:40] Because, I mean, they're great, all the things. But just actually in those like early days of like, hi, you know, I don't have anything to, you know, I might have something to talk about you later, but I'm like showing up today. They were like very politely concerned. [15:52] entirely uninterested and just like nice girl bad idea maybe she'll work at one of our companies you know they were like they didn't quite say that but it was like totally that was the vibe totally were they sending you customers they weren't even no they were not playing along the back end no zero they were just like wonder when that company's gonna die very politely and so it was like cool like i don't have to talk to you you know like cool great agree to disagree i'm the business you don't whatever and then it was uh i couldn't close friend of [16:22] idiot. Just, you know, call Sequoia. What are you doing? And so had another mutual friend introduce me to Andrew Reid and he's great. I ended up going with him and no regrets, but also no framework or like framework left by the wayside. Yeah. On this podcast, I've talked to a bunch of VCs about in what ways they think VCs might be helpful. But I'd like to hear from you in what ways you think VCs might be helpful to the extent that you think that they are. Sometimes some of them. I think VCs, I mean, at their best, like all of us,

[16:51] like smart-motivated people who are good at their jobs, their jobs are investing, their jobs are not operating. Like, that is, like, it sounds dumb and trite, but I think there's something deeply there. Like... [17:02] they're probably not good at running companies or if they are and are now doing like they've now no they've now chosen to do something else and like don't want to run your company you just make this better than i can yeah and they probably couldn't run your specific company anyway right yeah and so when you're looking to them for like or like things they're probably not good at is you know how do you like hire your first salesperson how do you compensate them when like chili piper starts riding leads under a couch cushion what do you do like that is not bc stuff [17:32] or if it is, I guess, Andrew, not like super, super early stage or some special thing, like something's probably off. Right. Well, they're probably capable of giving you an answer to that. It's actually I would think it's more like you probably shouldn't need to [17:45] You probably should have other vehicles to get that stuff. Right. I think recruiting support, especially in the early days. Yeah. When you say recruiting support, do you mean sending you candidates or do you mean closing candidates? I more mean closing candidates. There's some sending of candidates, but I do think that is like... Do you find the sending of candidates helpful or do you think the closing of what's all about? Tomato, tomato. Yeah. I mean, there's some stuff there, but I think in the early stages. And I think Sequoia's model is like, okay, we'll send you candidates up until this point and then we will... [18:13] Basically cut you off. Did you get candidates from that? I mean, did you get... [18:17] hires from that. [18:19] Very rarely. Yeah. Yeah. I also think in general, like those are hard because the candidate you're getting from that lead flow is also going to 14 other companies. And then so then you're like, OK, you were like one in the cohort. But like, how are you differentiated? Do they, you know, like there's a hard candidate. How does the closing play out? So like, what's the way that because I that's how I most, you know, poignantly, I would say use my board. I'm curious what that played out like for you.

[18:49] You have a person from Sequoia who's, you know, legendary firm from, you know, founding the IPO and whatever, you know, and like, let me tell you why Vanta is going to be the next thing we put on the wall. And of course, you know, I can say that, but like is... [19:02] They seem like they're more external than they probably are. And they're very experienced. So there's that bit. I also just think, and again, you know, but like in some ways, VCs just close more and get more practice because you're closing founders on deals. You're closing people for the company. You just have more reps. It's just professional sales, basically. Yes. And there's like a lot of more practice. Yeah. A little bit of. That's a good point. I've actually never heard someone say it quite like that, but I think that's true. You just like practice that more. Founders are also closing all the time, but it's like all VCs do. Right. Yeah. You're right. Yeah. Yeah. [19:32] hate it and it offends the like... [19:34] rational person in me like vc brand matters yeah do you think that's the top thing yeah you think it just sprinkles a little fairy dust on everything and it helps like self-fulfilling prophecy yes i think just like it's like all your conversion rates at every stage just get slightly better and this is for like candidates for customers for the next funding round like for media yeah it's like everything just gets 10 to 30 better once you had sequoia did it make recruiting a lot easier yes in a way that we talk but like yes in a way that i was like kind of annoyed by but like what's the dynamic [20:02] We'd have I don't feel like a literal person, but, you know, we'd have candidates and we'd like approach them. And it was a little funny because we raised our series A at 10 million. We'd be like, hey, we're the seed stage company, but like we actually have all this revenue and like, do you want to come work with us?

[20:15] And we're YC. And so I'd be like, no, you know, and then like, yeah, and then like the next day. Yeah, no. Like have fun over there. Yeah. And then like the next day we like announced the theory they from Sequoia, like 50 and 500. And then like the following day we like followed up. Everyone's in your mind. Yeah, exactly. And you're like, we are the same company. Right. Except now you have a higher 49A. Exactly. Like now it is the worst economic deal for you. Right. But like if you want to outsource your judgment to Sequoia, like I guess I'm here for it. [20:45] It was like a durable lift. Durable. And again, a way that I think I wouldn't have expected. But like the brand and Halo glow continues. And I should also say, like, I think Sequoia is very good at what they do. I'm very glad we worked together. Like all of that. Like there are real stuff here, very real stuff here. And the brand Halo just continues. Just dominates. Yeah. Is there anything on the actual help besides closing candidates that you get a lot of value out of or that you, even on a personal level, particularly value? [21:15] sometimes have, you know, their team, you know, sort of they are very good at knowing sort of everyone in the Valley. I think they pride themselves on, but it's true. And so they are very, you know, there's someone we're talking to and like, we don't have a lot of mutual connectivity and curious to talk to, you know, like they. Someone on the team knows. They're very good at doing that. There was a period when you're like trying to raise the company's profile. And again, to the emails that don't get replied to, you know, you email like conference or reporter and they're

[21:45] We would like partner with Sequoia and like Andrew and I would like do our conference together. And they like, yeah, we got on the conference stage because Andrew, you know, because Sequoia. Right. And I was just like the tag along. Yeah. But there was some of that where that helped, too. That makes sense. I guess on the recruiting topic in general, maybe now. [22:01] unrelated to investors, but with your own recruiting, what have you found over time that that's changed for you or that has been important for you? But like, if you go back, you know, and you think about like how you recruit when you were a seed or series A company, I guess something changed. Yeah. I think in the early days we were trying to be very frameworks driven and rigorous and everything was bespoke. Like your VC spreadsheet. Exactly. Yes. And it's like, you know, it's a little bit of like you hire like the first [22:31] distinct. But we would have these crazy... [22:35] multi-day interview loops that were like we would send someone through a i don't know tough mudder you know and like wonder why candidates dropped out yeah and you're like well that's because we asked them to like i don't know do an obstacle course i will say the people who got through like man were they down they were really down um but like in retrospect you're like wow we made that really hard for candidates and us to like [22:57] Yeah. [23:12] Inside the company or in the market or what? Both. But like inside the company, Vanta example, we for years just hired...

[23:19] generalists. And then like [23:22] year and a half ago or so like okay cool there we have a general we should have a generous pipeline but like man we you know we have mongo we should give people really no mongo we use graphql that technical such and whatever we need people who know graphql you know and like we should have these like separate pipelines in a way that this doesn't happen in design or sales or marketing because like the tech stack changes in you know i think what it is is like engineering recruiting [23:42] I mean, is just harder than all the other roles. Yeah. And that timelines are longer. And when you break the pipelines, you just. Yeah. It takes longer to get them stood up again. Did you do work trials? [23:53] Yeah. You don't know, right? We don't. Yeah. We don't know. We do our general, especially for like leadership roles of many sorts. We generally do just send them a bunch of data and information from what the role would be. And the project is usually like, so you dump the Google Drive and stuff on you. Like, what should we do? And like, there's very binary responses to that. There's people who are like, what do they want here? Like, this is madness. And people are like, oh, well, this is illuminating at least, you know, when I can like opt in. [24:23] or opt out. Yeah. But we try to do very... [24:26] Thank you. [24:26] Specific example, recruiting our CRO. So it's three years ago. Her thing was we sent her... [24:32] Seven gong calls? [24:34] Top reps, middle pack reps, bottom reps. We're like, here's your team. What do you think? Oh, wow. And you're trying to see, like, can they tell from the gone calls? And also, like, this is literally the team you're going to get handed. Yeah. Like, if you want to if you don't like this, like, let's just get that out now. Yeah. Like, and so we don't have to, you know, be like, oh, we have varying skill sets on the team. You know, you're like, here they are. Yeah. Yeah.

[24:54] And like, again, this is this is the range. Yeah. She stood out for many reasons. But part of it, she watched it and she's like, oh. [25:00] Here's what I saw here that we do like, you know, like unfazed and like very clear eyed and broke it down. Have you been like the type of CEO who wants to like be in every loop forever? Or did you let that go at some point? To what degree do you distribute decision making on recruiting? Yeah. So actually back to the early days that we had a principal's interview, you know, Vanta interview. And I did those probably up until we were about 50 people. [25:25] All of them. And then like I did have a team intervention where people were like, Christina, you are spending too much time on this. Stop doing it. Yeah. And so I like distributed it. I should not have done that. I think you should go through two or maybe three team interventions. Yeah. Not the first one. Yeah. You don't give it up after the first, at least the second. Yeah. So I should hang on to that a little bit longer. Like hang on till it's 200 people, you think? Like when do you think it's like what's your now assessment of like when it's like enough is enough? [25:55] When did that come for you? See, I didn't get there because I capitulated after the first intervention, which is probably like three quarters of a day. Got it. OK. Yeah. So maybe you could have gone twice as far. Yeah. I think you should like at least wait for two interventions. But then what I started doing six or nine months ago is now I do do that for every director plus candidate. Mm hmm. [26:12] So I like reinserted myself. And they can't get in without your blessing. I'll do non-blocking no's. Yeah. And like they're truly non-blocking. And it's like, here's what I saw. Yeah. If you as the manager. I wouldn't do this, but I'll support you. Yeah. And like, here are the gaps. And like, if you as the manager, like, think you got this.

[26:27] Cool. I will hold you to that. But if you want to make this call, like when you do that, does it usually go through or not go through? [26:33] Yeah, it's a good, it's like, are they actually non-blocking? Yeah, exactly. Or people like, I probably shouldn't do it. [26:37] Usually they're like, I shouldn't do it. But more of them should go through. Has it ever happened? Yeah, that they go through. And then it's been good? Yeah, totally. Yeah, yeah, yeah, yeah. Totally. Yeah, that's a good sign. Yeah. More people should like... [26:49] You do a lot of angel or you do some angel investing, let's say at least when you're [26:54] Thinking about if you want to back a founder versus if you want to hire somebody. Obviously, you're looking for both people to be talented and capable and, you know, whatever else. But like how different is the texture of what you're looking for? Pretty different. Yeah. Because I think there's a lot of like how we work stuff at Vanta that have like kind of been baked into the culture. And, you know, there have been very talented people. Actually, some of how we get the questions and the pieces of the principal interview is you like the very talented people who don't work out at the company and trying to tease that apart. [27:24] whole thing there that i just like don't care about when you're angel investing right because people don't want to work at vanta they don't have to work with me like doesn't matter they can you know go do themselves and basically the culture there's no culture interview no it doesn't matter no does that make it easier then because at vanta you need to both be good and you need this i think so yeah so you'd invest in somebody before you hired them basically yeah yeah totally yeah because like deeply there's like lots of ways to build these companies and like vanta you know i think

[27:54] Like people should just know what they're opting into. Yeah. And we try to do that in every process and be like, this can be for you. It can not be for you, but here's what it is. And it's kind of, [28:02] Not immovable, but like it's not going to turn 180 degrees. Whereas like somebody can build a company in a totally different way. Have you basically learned that a talented person who doesn't fit the culture, just it doesn't work out anyway? Yes. Like you've tried it and it just doesn't go the way you want it to. Yeah. Or on either direction. Yes. And so I think, you know, one of the things in probably two years ago we tried to get better at this, but was like just be hyper transparent about what the thing that's in the interview process and hope like smart people will sort themselves out. Yeah. Some of the work, some of the work that doesn't. [28:32] Yeah, I think one of the one of the sort of interesting sort of secular things that's happened to Vanta and you is you started a company at sort of the tail end of cloud, SaaS, Bullrun. Great. And then. [28:48] the world's all AI. [28:49] everything, everywhere all the time now. And so I'm curious how you... [28:54] taken the moment and how you basically are running things, given that you have this obvious thing that comes in and you obviously have to adapt. Like, what are like what are like the main things that have happened for you running the company now? There is a lot of. [29:07] hopefully like AI encouragement and excitement across the company. And that is both in like how we work, like our, you know, engineers using insert tool here. What are we building for customers? And I think, you know, really broadly, you know, like we've got half of folks who are like totally down and half of folks who are a little like, I have a job and it's really busy. And like, you want me to do what now? Like, can I just do my thing here? And so it's like, okay, how do you, how do you bring those together? And like, what are the carrots? And so, but I think at the,

[29:37] of conviction that like [29:40] This is real. Does it matter for your product or does it matter for just what you're the way you're building the way you're doing? I think it matters a ton for our product. So much of compliance is taking information in one format and putting it in another. Yeah. Right. Like, actually. And so there is just and like, I think the pieces of compliance will not change. But like, will you have to you probably you were. [30:00] Eric had to write your own policy documents. Isn't that like kind of, you know, you're like, yeah. And you also used a carrier. You're at least copy paste them and hope they're right. Exactly. Yeah. Yeah. And then you're like, if you had, if you want to know what was in them, you would read them. Yeah. That's crazy. Yeah. Now you can just get the summary. Exactly. You know, but like literally like we have all that stuff in the product now. That's a very small example, but I think it's a concrete one. And so it's like, yeah, there's still be policy documents, but like, how will they be created? How will they be disseminated? How do you know what's in them? How do you keep them in sync with everything else? Like that is all AI. [30:30] just to run your company differently across everything. We're in an AI procurement boom. I hope I don't say this in a million emails. Yeah, but a little bit. We used to be much stingier. And I think... If you're selling an AI product, here's Christina. I know. Christina, in banter.com. Yeah, exactly. Please don't. [30:47] But I think the thing we have actually, like now it's a large enough company where you have to... [30:51] Somewhat. [30:52] Be thoughtful here. And so what we're trying to do is like, okay, let teams do what they want to do and procure the tools and then have a forum for it, which it's like IT kind of runs and be like, okay, now we'll come together and be like, oh, we bought five meeting recorders. Cool. Let's pick one. Let's figure it out. And but like do that incrementally along the way. So do you prefer people to, would you prefer that?

[31:12] AI gets to you bottoms up that the best product wins through the team rather than somebody trying to come sell you top down with no usage. Yes. Yes. Now, because I think we were trying to do the top down, no usage and... [31:24] We're not making good tooling decisions. Interesting. Yeah. Yeah. And like, again, I can like critique and be like, oh, we should think more like PMs and our procurement. But like. Yeah. [31:33] that is not where the effort goes. Yeah, yeah, yeah. Do you want to use basically as much as [31:38] possible yes yeah okay yeah there was actually a a kind of a cute phrase but we were going back and forth about how many chat gpt licenses we have because chat gpt license were like kind of expensive and gemini is free yeah and like so can we just like be stingy about chat gpt licenses and make everyone use gemini basically and the answer is no um yeah well so it's like unused chat gpt licenses are very expensive used ones are actually pretty cheap right right and so it's like okay can you like get the energy focused on like getting the licenses used versus like being [32:08] testimonials. What are some of the I was about to ask this question in an obnoxious way of like, if you had to start a startup right now, what would you start? Which I'm going to ask a different way. What pieces of software? [32:18] Do you think that you could be or should be consuming that you're not yet? Like, what are some of the areas of the business at Vanta that you think should be AI-ified? I think go-to-market systems is... [32:30] A Rube Goldberg machine constructed by like seven different tools. Yeah, that's what we had. And we had like nine biz ops people holding it all together. Exactly. Yes. Yeah. And it was like, once it gets to that system, they're going to grab this ball and put it over here. Exactly. Exactly. And it's just kind of nuts because you're like, OK, if this were engineering, like this does not exist in engineering. It would be unacceptable. It would be entirely unacceptable. It would be unacceptable a decade ago. Yeah. And so like someone should fix that. Yeah. Can you say a little bit more about like, can you, you don't have to name the vendors, but like name the parts of,

[33:00] the funnel you're talking about. Yeah, like I don't even mean the marketing, but it's like someone goes to Vanta.com and it's like, OK, I want a demo or I want Vanta. And then like, how does that get to a sales rep or how does that get to closed one? And like, [33:11] Oh, man, we got we got the ball. The balls are going into the tubes or onto the floor. Yeah. I never understood why it had to be so messy. Like I get that it's kind of complicated. And then you have like race conditions between the tools. And you're just like, how does anyone put up with this? Everyone put up with it. Yeah. Kind of nuts. That's good. What else? Collections, contract terms. It is like the least favorite part. [33:33] of everyone's job, including the, like, our customers, right? You'd think AI would be really good at that. Yes. Like, parsing the document, doing the perpetual reach-outs to people. Yes. And, like, we've got some of it, but it's, it's, like, rules-based and doesn't work and people miss the emails and, like, and then it's, like, heightened emotions and, like, oh, boy. Support kind of, or, like, the, like, [33:54] something is not working or... In support? Yeah. The customers, just regular customer support. You're saying that the... [34:01] the chatbots are not working well? Is that what you're saying? Some of them. Yeah. Or I think we have some of that. And then I think we have... Or is it the tooling around them and like the reporting on it? Is that the issue? I do want a lot of this stuff to go further. So one thing we have built is just like custom GPT for like the Banta tone of voice. We call it Ilma Bot because Ilma is our mama's name. But, you know, it's like our copywriters can only do so much. And so how do you kind of Bantify the writing? And I think that works very well

[34:31] I kind of want it for like all support tickets. And honestly, like all customer columns. [34:36] Do you think sales will get AI... [34:38] Affied? Somewhat. I think there will be reps, but like even like we actually, I think, are quite good at enforcing Salesforce hygiene amongst our reps. You know, so like it works, but like... [34:50] Oh, how much time these folks spend, you know, filling out command plans. And look, there's a part where you're like, you do actually want them to know the command plan. Yeah. Because that's what they're supposed to go execute on. Have you had any luck with like AISDRs? No, we haven't really tried. We tried a little bit, but we haven't. We're not a good. Yeah. Still walking up the like hierarchy of SDR tooling. Yeah. What else? Anything in like security or operations or anything like that? I think that like security operations center and that like other SOC. SOC? Yeah, not SOC 2. That's confusing. The other kind of SOC. That's frustrating. Space. [35:20] Um... [35:21] maybe in your company, maybe outsource that like look at alerts all day. Yeah. And then like the 10 years ago, Dropbox way was like write a bunch of rules and like kind of, but I think there's a bit of like, okay, that was like, [35:32] the rule writing phase. How do we just AI-ify what is important, what is not? And that's hard and you don't want to mess it up. But like, turns out, you know, again, hardworking people working all the time, staring at alerts all the time also mess it up. Yeah. And so how do you do that? What about like marketing very top of funnel? Any, has anything like [35:48] change there? Like the LLM SEO stuff, whatever you call it, AIEO or whatever people are calling it. Yeah. Is that it? I don't know. That thing is, I think, very real. We actually see

[36:02] impressions on our keywords dropping. It's like we might have a like... [36:05] The same or higher impression share, the same or higher like CPMs or CPCs, but like overall it seems like search volume is dropping. And like we see that. That's crazy. In our SEM spend. That's really crazy. Yeah. And your assumption is basically that's all just gone to the LLMs. Yes. Yeah. Yeah. [36:21] Yes. That's just like a whole new work stream, I guess. It seems like it. And you probably know the tools better than I do. But when I kind of poke around, it seems like a lot of the... [36:28] tools or work is like you just repeatedly run the same query in a bunch of tools and then [36:34] you know, like write down where, you know, like how you do and then you rerun it the next day and you rerun it. You know, I'm sure someone will build a bot thing. They're like, oh boy. Is there anything else in like... [36:44] HR, like people stuff or anything in finance? Oh, we did something like maybe moderately controversial. I'm curious for your take. Was we actually encouraged and wrote a built a like or prompted a custom GPT, but for managers to use in perf reviews to help them give feedback. Yeah. Yeah. I think that's good. And yeah, because it's kind of like I think my general thing, you have much smarter ideas, but like my general thing on perf reviews, it's like 360s and perf reviews are super helpful if you actually do them. Yeah. [37:14] it just ends up taking 60 hours from everyone's time and being terrible. And so like... [37:19] You either need to go all in or all out. So how do you get it? My whole thing with performance reviews is basically it's like what you're trying to get to is a shared agreed... [37:29] you know, nugget of insight about what could be better.

[37:33] And maybe that takes three hours to get there. Maybe it takes 30 minutes to get there. Maybe it never gets there. But I think oftentimes doing the work to get there is important. But really what you need is just like a consolidated insight that both the manager and the person being reviewed are like, yeah, that is something I need to get better at. Yep. So however you get there. However you get there. Yeah. And like get there and get it clearly articulated and like that thing. [38:03] Just getting to the like, here's an insight that's useful. Yeah. Is worth a lot. Right. Right. And like I can read it and like think about it and agree or disagree. But like I got it. Yeah. It just has to be a useful insight. But if it gets there, which it seems like in a lot of cases it does, it's really good. The last topic I want to go to is so you're what? Seven years in. Something like that. What's the founder sort of mindset that you've, you know, settled into? Not that you're settled into one and I'm sure there's still turmoil and evolution. [38:33] journey that you've been through. Yeah. Two things. The like [38:37] trope of like a dozen could eat through you just go faster is deeply true and i think the lived experience is like you know kind of every day you i don't know where that guy feel like i think only halfway know what i'm doing or like that's a new skill and so you're you never feel like you're like on it i feel like i'm totally on it but then every once in a while i'll like go back and you know someone's out so i'll like do the one-on-ones with their manager and be like oh [38:57] I can do this now. Right. And the first time I was managing or managing a manager, I didn't feel comfortable with

[39:03] But like, [39:04] I did learn something. And you have these kind of moments, which is one of like talking to an early stage founder. And you're like, oh, no, I have a point of view here and I adamantly believe it. Maybe I'm wrong, but like I've learned something. Yeah. So there's some of that, even if in the day to day you're like still and like, well, I haven't done this before, but here we go. Yeah. And then I think there is a all the like. [39:25] It's like different type of CEOs or like the job changes and your job is to like make the, build the product and then build the company and then build the team or team, whatever it is. Yeah. You know. Some order. Some order. You did it. Not that order. You just don't remember it. Probably product team company now that I say that out loud. Yeah. Yeah. [39:41] And like, those are very different. And there's like, oh, it's different types of people. You enjoy different things. And like... [39:46] I think in some way that's true, but I also think I don't know. [39:49] you know, joke that's kind of a joke is like, no, you just have to like Stockholm syndrome yourself into being like, well, I used to be someone who likes to build products, but now I love building teams. And whether or not I identified as that person a few years ago, it doesn't matter. Now that's me. And I believe it, you know? And then like when it changes, you're like, now I'm this person. I love HR policy, you know? Because that's what the company needs right now. And like, you know, joking, but not like figuring out how to be like, this is the game and the puzzle

[40:19] I will just be sad and burned out and unfulfilled. And this is not sustainable. Did you have a part of the journey where you... [40:28] We're both... [40:29] Doing things that you didn't enjoy and hadn't yet figured out how to like control your own like mindset and emotions like that. Yes. Because I imagine at the beginning. Yes. I mean, who doesn't love? I mean. [40:40] Everybody loves building a product. Everybody loves getting that early customer rush. Like that stuff is just like objectively fun. Yes. And then there are things that are like debatably fun and some people might love them, but not everybody loves them. Yes. Yeah. And I think it's, and I remember this, especially in the early days, because like for me, the first version of this was, okay, we have this product and company and like recruited a couple of engineers. And I have to go like do all of go to market and both do it and recruit people. Yeah. And I didn't know how to spell go to market, like kind of actually. And so it was like, I got to do this. Everyone else is catting me on to do it. [41:10] Yeah. Because I've never done it. Yeah. [41:12] And like kind of raking myself over the coals for that. [41:15] And then sort of being like, okay, right. I'm bad at it because I haven't done it. [41:19] My job is to get good fast. Yeah. Right. Like it's trajectory, not, you know, anything else, but like kind of reframing that. Did you do anything to get that sort of like self-control that you're now at of being able to say like, [41:30] I like this because I told myself I'm going to like that. Like, was there like, you know, somebody you picked this up from? Was there, did you like read a bunch of like Buddhist books? Did you like something, you know, like what did you do to get to that? Because I think very few people have that kind of ability to tell themselves that this is how I'm going to feel about this thing. Yeah, I think a bit of, for me, it used to be runs. I went long, it was like four miles, you know, but it was just like, and I live by Golden Gate Park. And you're like, also when I get really frustrated or pissed off, like go run.

[42:00] something. We have a mutual friend, Jay Zack Stein, who is like very... I think it's a very helpful, like, playback sounds like what you're saying. Sounds like this is a thing, you know, like prompting on self-reflection. And then... [42:13] I think also just talking to other founders, right? And then you talk to the folks... [42:19] who are like [42:20] Oh, I'm supposed to be building the company, but like, I still just want to build the product. And like, I'm really annoying, you know, and I'm annoyed and I'm unhappy and just kind of being like, well, that seems bad, you know, but like, I get it. Right. Absolutely. Well, Christina, this was really fun. Thank you for taking the time to do this. It was a it was a blast for me. Thank you so much for having me.