Uncapped #17 | Christina Cacioppo from Vanta

20:31Yeah, exactly. And you're like, we're the same company. Right. Except now you have a higher four in our name. Exactly. Like now it is a worst economic deal for you. Right. But like if you want to outource your judgment to Sequoia, like I guess I'm here for it. Yeah. Right. Did you experience it as like a one -time pop or have you experienced it as 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 have the fact like I think Sequoia is very good with. They do very glad we worked together. All of that. Like they're real stuff here.

20:59Very real stuff here. And the brand Halo just continues. Here's dominance. 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? No, I'm the recruiting sense week yet. Back channels. And sometimes have their team, you know, sort of they are very good at knowing sort of everyone in the valley. Something they pride themselves on, but it's true. And so they are very, you know, they're like 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.

21:30Someone 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, the emails that don't get replied to you and I email like conference or reporter and they're like, you are one of 9 ,000 and you know, next please. We would like partner with Sequoia and like Andrew and I would like do a conference together. And they like, 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 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?

22:10But like if you go back, you know, and you think about like how you recruited when you were a seed or series like company. So bad. I guess something changed. Yeah, basically. I think in the early days we were trying to be very framework -driven and rigorous and everything was bespoke. Like your VC spreadsheet. Exactly. Yes. And it's like, you know, just like what you've like, you hire like the first person in every role. So every role is distinct. Yeah. But we had have these like crazy like multi -day interview loops that were like we would send someone through a, I don't know, tough mother, you know, and like wonder, I can't if it's dropped out.

22:42Yeah. And you're like, well, that's because we asked some to like, I don't know, do an obstacle course. Uh -huh. And we'll see the people who got through like man, where they don't work. They really wanted to join. Yeah. They were really down. But like in retrospect, you're like, wow, we made that really hard for candidates and us to like unclear ends. Engineering recruiting, you just, you mess it up every two years no matter what. It is hard. It is both hard and doable and you just have to do it. So it's my, I'm talking to someone last night about this. And then you like figure out engineering recruiting for a bit and then something changes.

23:11What changes inside the company or in the market or what? Both. But again, so the, the, the, the example we for years just hired generalists. And then like year and a half ago or so or like, okay, cool. There we have a general, we should have a generalist pipeline. But like, man, we, you know, we have manga, which is people really no manga. We use GraphQL, that technical, such and whatever. We need people no GraphQL, you know, and like we should have these like separate pipeline. In a way that this doesn't happen in design or sales or marketing. Because like the tech stack changes in. You know what I think what it is is like engineering recruiting.

23:42I mean, it is just harder than all the other roles. Yeah. And that timelines are longer. And so when you break the pipelines, you just, yeah, it takes longer to get them stood up again. Did you do work, Charles? At that. Yeah. In the early days, we don't. Yeah. We don't know. We do our generate, especially for like leadership roles of, 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, do I have a stuff on you? Like, what should we do? And like there's very binary responses to that.

24:15There'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, and I can like opt in or opt out. But we try to do very specific example, recruiting our CRO. So it's three years ago. Her thing was we sent her seven gong calls, top reps, middle pack reps, bottom reps. We're like, here's your shame. What do you think? Oh, wow. And you're trying to see like, can they tell from the gong 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.

24:49Like, and so we don't have to, you know, be like, oh, they're very skill sets on the, you know, you're like, here they are. Yeah. And like, again, this is, this is the range. She stood out for many reasons, but part of it, she watched those and she's like, oh, here's what I saw here, who we do, like, like, unfazed and like, very clear eye and work 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, yeah. So actually back to the early day, we had a principal interview, you know, advanced interview.

25:21And I did those probably up until we were about 50 people, all of them. And then like, I did have a team intervention where people were like, because you know, you were spending too much time on this, stop doing it. Yeah. And so I'd like distributed it. I should not have done that. Uh -huh. I think you should go through two or maybe three team interventions. Yeah. Not the first one. Yeah. You don't give it up to the first, at least the second. Yeah. So I should hang on to that a little bit longer. Like hang on till it's a 200 people, you think? Like when do you think it's at like, what's your now assessment of like, when it's like enough is enough?

25:51When you're spending probably more than a day and a half of your five days. Yeah. And when did that come for you? See, I didn't get there. Oh, see where I left it. I capitulated after the first intervention. I see. Which was it. Which was it? Which was probably like three -quarter through a day. Got it. Okay. Yeah, yeah. It's maybe a couple of choices for it. Yeah, I think you should like at least wait for two interventions. Yeah. But then what I started doing six or nine months ago is now I do do that for redirector plus candidate. Mm -hmm. So I like reinserted myself. And they can't get in without your blessing.

26:15Mm -hmm. I'll do non -blocking nose. Yeah. I mean, they're truly non -blocking. And it's like, here's what I saw. Yeah. If you use the manager. Yeah, I wouldn't do this, but I'll support you. Yeah. And like, here the gaps in like, if you use the manager, like, think you got this, 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? Yeah, it's a good, it's like, are they actually non -blocking? I probably shouldn't do it. Usually I can't do it. But I know where them should go through. Yeah. Has it ever happened? Yeah, they've gone through.

26:43Yeah. And then it's been good. Yeah. Totally. Yeah. Yeah, yeah, yeah. Totally. Yeah, that's a good sign. Yeah. Yeah. No more people should, like, yeah. You do a lot of angel, or you do some angel investing, let's say, at least when you're thinking about if you want to back a founder versus if you want to hire somebody. And so 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. 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.

27:14And, you know, there've been very talented people, actually some of how we get the questions and the pieces of the principal interview is you like, they're very talented people who don't work out of the company and trying to teach that effort. Anyway, so there's like a whole thing there that I just don't care about when you're angel investing. Right. Because people don't want to work at Vanta. They don't want to work with me. Like, it doesn't matter. Mm -hmm. They can, you know, go do themselves and eat. So basically the culture, there's no culture in your view. No. Basically it doesn't matter.

27:35No. Does that make it easier then? Because at Vanta you need to both be good and you need to see. I think so. Yeah. So you'd invest in somebody before you hired them basically? Yeah. Yeah. Totally. Yeah. Because they like, deeply there's like lots of ways to build these companies. And like Vanta, you know, I think there's a, it's like metaversion of the gong call. Sales example is like, people should just know what they're opting into. Yeah. And we try to do that. And it would be like, this can be for you. It could not be for you. But here's what it is. And it's kind of unimovable. But like, it's not going to turn 180 degrees.

28:06Whereas like somebody can build a company and totally different. 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 wanted to. Yeah. Or on either direction. Yes. And so I think one of the things in so two years ago we tried to get better at this. But it was like, just be hyper transparent about what the thing is in the interview process. And hope like smart people will sort themselves out. Yeah. Some of the works on it doesn't. But like that's, I do think we owe that to candidates.

28:32Yeah. I think 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, sass, bull run, great. And then the world's all AI, everything everywhere all the time now. And so I'm curious how you 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 hopefully like AI encouragement and excitement across the company.

29:11And that is both then how we work. Like our engineers using insert tool here. What are you building for customers? And I think really broadly, you know, like we've got half a folks who are like totally down and half a 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? Yeah. And so it's like, okay, how do you how do you bring those together? Unlike what are the carrots? And so, but I think at the my level, leadership level, there is just like a ton of conviction that like 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 good.

29:46Like I mean, it matters a ton for our product. Yeah. 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 kind of like write your own policy documents. Isn't that like kind of you know, you're like, yeah, and you won't see these are carrier pages. You're at least copy paste them and hope they're right. Exactly. Yeah. And then you're like, if you had if you want to know what is in them, you wouldn't read them.

30:10Yeah, that's great. Yeah, now you just get the summary. Exactly. You know, we're 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. Yeah. 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. How much AI are you consuming just like other AI products just to run your company differently across everything? We're in an AI procurement boom. I hope I don't say this thing in my email.

30:36Are you buying them? Yeah. Yeah, but a little bit. We used to be on stingier. And I think if you're selling an AI product, here's Christina. I know. Yeah, I'm Bantanaka. Please don't. But I think the thing we have actually, like now it's large enough company where you have to somewhat 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 which is like IT kind of runs and be like, okay, now we'll come together and be like, oh, we bought by the meeting recorders. Cool. Let's let's figure it out and but like do that incrementally on the way.

31:09So do you prefer people to would you prefer that 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 we were trying to do the top down no usage and we're not making good tooling decisions. Interesting. Yeah. And like again, I can like critique and be like, oh, we should think more of the gums and our procure and but like, that is not where the effort goes. Yeah. Yeah. Yeah. Do you want to use basically as much as possible? Yes. Yeah. Okay. Yeah. There was actually a, this is 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.

31:50Yeah. And like so can we just like be stingy about chat GPT licenses and make everyone use Gemini. And the answer is no. Some worth it. Yeah. Well, so it's like unused chat GPT licenses are very expensive. You understand they're actually pretty cheap, right? And so it's like, okay, can you like get the energy focused on like getting the licenses used versus like being person -onious about that? What are some of the, I was about to ask this question in an anxious way of like, if you had to start a startup right now, what would you start? But yeah, I'm going to ask you a different way. What pieces of software do you think that you could be or should be consuming that you're not yet?

32:21Like what are some of the areas of the business advanced that you think should be identified? I think go -to -market systems is a Rube Goldberg machine constructed by like seven different tools. Yeah, that's what we had. We had like nine bizzaps people holding it all together. Yes, exactly. Yes. Yeah. And it was like once I get 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, okay, if this were engineering, like, or this doesn't not exist in engineering. It would be unacceptable. It would be entirely unacceptable.

32:50We were like, it's a little a decade ago. Yeah. And so like so much to fix that. Can you say a little bit more about that? Like, can you, you don't often name the vendors, but like name the parts of, like me, the parts of 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 is like, okay, I want a demo or I want Vanta. And then like, how does that get to a sale of Rapper? How does that get to closed one? And like, oh man, we got, we got the ball, the balls are going to be the tools. You know, it's the one of the floor. Yeah, I never knew so I had to be so messy.

33:18Like 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. Okay, that's good. What else? Collections, contract terms. It is like the least favorite part of everyone's job, including the like, the our customers, right? You think I 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 for like the like, I use something is not working or.

33:56In support. Yeah, customers, just very much support. You're saying that the 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, where's 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 GBT for like the banter tone of voice. We call it ilma bak because ilma is our, our arm is named. But you know, it's like our, our copywriters can only do so much. And so how do you kind of bandify the writing?

34:29Yeah. And I think that's works very well for marketing. Copy. I kind of want it for like all support tickets. Yeah. And honestly, like all customer columns. Yeah. Do you think sales will get AI a five? Some what I think there will be reps. But like even like, we actually, I think are quite good at enforcing sales force hygiene among star reps. You know, so like it works. But like, whoo, 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. Because that's what they're supposed to go execute on.

34:59If you had any look with like a sdr's. No, we haven't really tried, we tried a little bit. We haven't. We're not a good. Yeah. So 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 the like other soft, soft, yeah, not so stupid. So I'm gonna talk to you. So that's frustrating space. You know, like the old way to solve that is put a bunch of people in a room in a room, maybe in your company, maybe outsourced that like look at alerts all day. Yeah. And then like the 10 years ago Dropbox way was like right a bunch of rules and like kind of but I think there's a bit of like, okay, that was like the rule writing phase.

35:33How do we just AI? If I what is important? What is not? And that's hard. You don't want to mess it up. But like turns out, you know, we get hardworking people working all the time. Staring at alerts all the time also mess it up. And so how do you do that? What about like marketing very top of funnel? And has anything like changed there? Like the LLM SEO stuff, whatever you call it, AI, EO or whatever people call. EO? Yeah. Could it? Yeah. I don't know. I don't know. But like that thing. Yeah. Is I think like very real. We actually see impressions on our keywords dropping. It's like we might have like the same or higher impression share, the same or higher like CPMs or CBCs.

36:10But like overall, it seems like search volume is dropping. And like we see that. That's crazy. And our SEMs vent. That's really crazy. Yeah. And your assumption is basically that's all just gone to LLM's. Yeah. Yes. That's just like a whole new worksheet, my guess. It seems like you probably know the tools better than I do. But when I kind of poke around, it seems like a lot of the tools or work is like, you just keep repeatedly run the same query in a bunch of tools. And then, you know, like write down where, you know, like how you do. And then we run it the next day and you're, you know, I'm sure someone will build a bot thing.

36:41But like, oh boy. Is there anything else in like HR, like people stuff for anything and finance? Oh, we did something like maybe moderately controversial and curious for your take. Was we actually encouraged and wrote a, built a like repumped a custom GPT, but for managers to use and prefer views? Yeah. To help them get feedback. Yeah. Yeah, I think that's good. And yeah, because it's kind of like, or I think my, I don't know, my general thing. You have much smarter ideas. But like my general thing, I'm prefer views. It's like 360 than per views are super helpful. If you actually do them, if you kind of do it halfway, it just ends up taking 60 hours from everyone's time and being terrible.

37:18And so like, you know, you either need to go like all in or like all out. Yeah. So how do you get it? My only thing with performance reviews is basically it's like what you're trying to get to is a shared agreed, you know, nugget of insight about what could be better. 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. Or like, yeah, that is something I need to get better at.

37:47Yeah. So however you get there. How have you get there? Yeah. And like get there and get it clearly articulated. And like that thing. It's not so dissimilar from like the way a lot of consumers are using it. For like kind of like, Borland therapy or just straight -up therapy type uses. Where it's like, you know, maybe it's a human better in some ways. But just getting to the like hears and insight that's useful is worth a lot. Right. And like I can read it and like think about it. It's a great disagreeable like. I got it. Yeah. Just has to be a useful insight. But if it gets there, which it seems like in a lot of cases, it does.

38:17It's really good. The last topic I want to go to is, so you're what? Seven years in. I don't know. Yeah. 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 they're still turmoil and evolution. But like, what is the inner game journey that you've been through? Yeah. Two things. The like trope of like a Dalek and Kati -Thru, you just go faster. It's deeply true. And I think the lived experience is like, you know, kind of every day, you I don't know where that guy, I feel like I only halfway know what I'm doing. Like I got a new skill.

38:47And so you're, you never feel like you're like on it. I feel like I'm totally on it. But then everyone's like, 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, I can do this now. Right? And the first time I was managing or managing a manor, I didn't feel comfortable. But like, I got, I did learn something. And you have these kind of moments, we did one of like talking to an early stage founder. And you're like, oh, no, I, I have a point of view here. And I adamantly believe it. Maybe my favorite wrong. But like, I've learned something.

39:17Yeah. So there's some of that, even if in the day -to -day, you're like still and like, well, I'm at almost four. But here we go. Yeah. And then I think there is a, all the like, it's like different CEOs. 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. It's not more than about that. You did it. You did it. Not the former. Yeah. Probably product team company, not a certain outlet. And like, those are very different. And there's like, oh, it's different type of people.

39:43You enjoy different things. And like, I think in some way, that's true. But I also think I don't like, you know, joke. That's kind of a joke. It's like, no, you just have to like stock homes and norm yourself into being like, well, I used to be someone who likes to be a tax. Yeah. 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. Yeah. I love HR policy. You know, because that's what the company needs right now. Yeah, totally.

40:11And like, you know, joking, but not like, figuring out how to be like, this is a game and the puzzle and like, the journey. And I need to take joy in it. Because otherwise, I will just, you know, like, be sad and burned out and unfulfilled. And like, this is not sustainable. Did you have a part of the journey where you were both 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, I mean, who doesn't love, I mean, everybody loves building a product. Everybody loves getting that early customer.

40:42Right. Like, that stuff is just like, objectively fun. Yes. And then there are things that are like, debatable, fun and some people might love them, but not everybody loves them. Yes. Yeah. And I think it's, and everyone's a fashion the early days. Because like, for me, the first version of this was, okay, we have this product in company and like recruited a couple of engineers. And I have to go to 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 was counting me on to do it.

41:09And like, wow, my bad at it. Yeah. Because I've never done it. Yeah. And like, kind of raking myself over the colds for that. And then sort of being like, okay, right. I'm bad at it because I haven't done it. My job is to get going fast. Yeah. Right. Like, it's, 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, 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?

41:39Did you like something, you know, like what did I 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. Yeah. I think a bit of, for me, it used to be runs. I went along, it was like four miles, you know, but it was just like, and I live by going to the park and you're like, also when I get really frustrated or pissed off and like go run. Yeah. Usually at some point, there was like some, something we have a mutual friend, Jay's ex -Dian who was like, who they get a very helpful like, playback sounds like what you're saying.

42:08Sounds like this is a big, you know, like, a like prompting on self -reflection. And then I also just talking to other founders, right? And then you talked to the folks who are like, oh, I'm supposed to be building the company, but like I still just want to build the product. And like, I'm really, you know, and I'm annoyed, and I'm unhappy, and just kind of being like, well, that seems mad, 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 blast for me. Thank you so much for having me.