Pod Insights Uncapped with Jack Altman Uncapped #17 | Christina Cacioppo from Vanta About this episode Christina Cacioppo is cofounder and CEO of Vanta, which is on a mission to secure the internet and protect consumer data. The trust management platform was valued at $2.5 billion in 2024 after a Series C investment led by Sequoia. Vanta went from $10M in annual recurring revenue in 2021 to $100M in 2024, while also giving us one of the best tech billboards of all time, “Compliance that doesn’t SOC 2 much.” Before founding Vanta in 2018, Christina was an investor at Union Square Ventures and helped bring Dropbox Paper to market as a product manager.
We covered:
Operating in a competitive market
Fundraising frameworks
Recruiting as you scale
What should be AI-ified internally
The inner game of being a founder
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Timestamps:
(0:00) Intro
(0:25) Staying under the radar
(3:29) No referees in capitalism
(5:20) Shipping velocity
(6:43) Mindset on competition
(8:09) Structuring a GTM approach
(10:25) Fundraising strategies
(16:36) VCs being “helpful”
(21:57) Recruiting as you scale
(28:33) Adapting to the AI era
(32:09) What should be AI-ified
(38:18) Mental game of being a founder
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More on Vanta and Christina:
https://www.vanta.com/
https://x.com/christinacaci
More on Alt Capital and Jack:
https://www.altcap.com/
https://x.com/jaltma
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https://linktr.ee/uncappedpod
Email: [email protected]
Transcript 10,322 words · 2 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 No, you just have to like Stockholm syndrome yourself into being like, well, I used to be someone who liked to build products, but now I love building teams. And whether or not I identified as that person at two years ago, 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. Because that's what the company needs right now.
0:19 Jack Altman? All right. I'm here with Christina from Vanta and very excited for this conversation. Thanks for doing this with me.
0:23 Speaker 00 Thanks so much for having me.
0:24 Jack Altman? Okay, so what I want to start with is we are in a moment with AI where I would say markets are 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 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
1:08 Jack Altman? you've gotten yourself to over the years?
1:10 Speaker 00 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 I tried to kind of keep it quiet about how well we were doing. We'd got out. And then in 2020, when everyone was at home board, lots of people started Vanta competitors.
1:34 Jack Altman? You did try to keep it quiet for a while there, right?
1:36 Speaker 00 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?
1:42 Jack Altman? And your mindset was basically just like, let's get as much traction as possible before people think that this is a good idea.
1:48 Speaker 00 Yes, because people thought it was a terrible idea. No startups got socked to us. No one knew, 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?
1:58 Jack Altman? And how did you know it was good? How did you have the confidence to know it was good enough that you should keep it a secret?
2:02 Speaker 00 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. 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.
2:17 Jack Altman? Were you getting customers with like a janky product?
2:19 Speaker 00 A hundred percent.
2:20 Jack Altman? Yeah.
2:20 Speaker 00 During Y C, a Y C company that bought Vanta called it the brutalist white website.
2:25 Jack Altman? That sounds nice.
2:26 Speaker 00 Yeah, you know, that was, that was, the brutalist white website sucked in a million ways, except it got people to their outcome.
2:33 Jack Altman? I guess you also had a very good why now, right? Like there like a thing really happened.
2:36 Speaker 00 Kind of, or like, yes.
2:38 Jack Altman? Or did that just seem that way?
2:39 Speaker 00 It just seemed that way. Like, the why now existed in 2016 and 2014. 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.
2:50 Jack Altman? So what was the first year it could have happened?
2:52 Speaker 00 14, probably, 13, 14.
2:54 Jack Altman? Okay.
2:54 Speaker 00 Yeah.
2:54 Jack Altman? So it was a reasonable thing, but it was like,
2:56 Speaker 00 But I couldn't give you a-
2:57 Jack Altman? A startup could have done it for a few years.
2:59 Speaker 00 Yeah.
2:59 Jack Altman? Okay.
2:59 Speaker 00 And so that's actually, I used to love the why now question, especially about USV. You're like, oh, it's so intellectual and like-
3:04 Jack Altman? Well, I didn't know that there was that gap in time between-
3:06 Speaker 00 And then with Vanta, you're like, yeah, yeah, I only have one of a why now.
3:09 Jack Altman? I thought Vanta was the first one take, which I guess you were the first one to take advantage of it.
3:13 Speaker 00 But like, again, someone could have.
3:14 Jack Altman? Yeah.
3:15 Speaker 00 Yeah.
3:15 Jack Altman? Okay.
3:15 Speaker 00 There were a couple really manual solutions, but I think it was like lawyers looked at the problem, compliance people looked at the problem and they so, they solved it in just a different way than an engineer.
3:24 Jack Altman? Yeah.
3:25 Speaker 00 But like, we weren't particularly, you know, it was like, anyone could have figured that part out. They just didn't.
3:29 Jack Altman? Okay, so you, you stayed secretive as long as you could, but then at some point you didn't, you weren't secretive.
3:33 Speaker 00 Yeah, well, and the word kind of got out. And so, and then we got this like host of knockoffs and, you know, I think we went through like, oh, well, they're just knocking off. Or 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 and we built it in two months. And like, they suck and we're awesome.
3:51 Jack Altman? Is that how they said it too?
3:52 Speaker 00 Yes, they're literally in that.
3:53 Jack Altman? That was their voice.
3:53 Speaker 00 Yes, very surfer bro.
3:54 Jack Altman? Uh huh.
3:55 Speaker 00 You know, we like went through the phase of like, well, that won't work or that's not fair or like. And I think the thing, you know, you learn is like, all is fair in love and capitalism. And it doesn't, you know, no one cares. And like customer, like customers are trying to solve the problem.
4:11 Jack Altman? Yep.
4:12 Speaker 00 And like, they don't care if you're first. They care if you're the best thing today.
4:15 Jack Altman? Yep.
4:16 Speaker 00 They don't care if, you know, you were secret chopped and someone took screenshots and like ripped everything off. There's no referees in capitalism.
4:23 Jack Altman? Yeah.
4:24 Speaker 00 Um, and you kind of want there to be one, but like, there's not.
4:26 Jack Altman? There's not.
4:27 Speaker 00 And I think you've got to stop searching for one. And
4:30 Jack Altman? Did you have a thing switch for you? Like, were you at one point looking for referee? And then you decided to stop?
4:34 Speaker 00 Yes. And then you're like, there's like, what am I, you know, like even like if I had a magic wand, what would I con like, what would the referee? And you're like, I don't know, you know?
4:41 Jack Altman? Great.
4:43 Speaker 00 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.
4:51 Jack Altman? Yep.
4:52 Speaker 00 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 it. I mean, it's important internally, but it's also not or not to not like rest on your laurels way.
5:02 Jack Altman? Yeah.
5:02 Speaker 00 Like, I think a lot of why I do and a lot of us like software is because it's so fast moving.
5:06 Jack Altman? Mm hmm.
5:07 Speaker 00 Blessing and cursed. And you're like, only as good as the last thing you shipped.
5:09 Jack Altman? Yep.
5:10 Speaker 00 And so it's like, okay, cool. What have you shipped for me lately?
5:12 Jack Altman? Yeah.
5:12 Speaker 00 And like, that's how customers think. And that is great and terrible, but like also reality. And so you just got to go with that.
5:19 Jack Altman? Yeah. What else from a mindset, you know, perspective, did you end up building over time besides like all's fair and love and capitalism? Which I think is like a very, uh, that is like hard, hard earned wisdom. But what else came to you over time?
5:33 Speaker 00 Shipping velocity. Uh, cause I think also, you know, then the Vanta, and even the Vanta 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 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.
5:55 Jack Altman? Right.
5:56 Speaker 00 And then we get this kind of negative feedback and then, and then we're just like very demoralized. And then customers like, what have you shipped for me lately? Like nothing.
6:03 Jack Altman? Yeah.
6:04 Speaker 00 Right? And so trying to get to like the frame, and I feel it's 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.
6:14 Jack Altman? Yep.
6:15 Speaker 00 And so the team, it's like, how do you minimize the time between, you know, the zero within the fourth shift?
6:20 Jack Altman? How quickly can we get to V four?
6:22 Speaker 00 Exactly.
6:22 Jack Altman? Yeah.
6:23 Speaker 00 And like V four should be right and I'll hold you to that. But V one, like V one does not have to be right. And like trying to switch to 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 the mental model of school, but actually not to real life.
6:40 Jack Altman? Totally.
6:41 Speaker 00 And trying to like flip that too.
6:42 Jack Altman? Competition is one of the like more psychologically vexing parts of a startup.
6:47 Speaker 00 Yeah.
6:48 Jack Altman? 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?
7:01 Speaker 00 I think there is, and this works kind of sometimes well and sometimes not, but I think for me, what I, when I'm at my best, what I try to do is like, if a competitor is do, 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 gonna call this new field this and like, everyone's gonna call it and like, have we created a category now, right? Like, there's, there's parts you can kind of weaponize for yourself.
7:23 Jack Altman? Yeah.
7:24 Speaker 00 The other part is to do something different.
7:25 Jack Altman? Yep.
7:26 Speaker 00 Why? And I think it's trying to start from the like, assume they're smart. Not like assume they're idiots.
7:31 Jack Altman? Yep.
7:31 Speaker 00 And be 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. But like, I think it is always a useful thought exercise, even if you've dismissed them the last 10 times, something like this.
7:45 Jack Altman? Have you had it go the other way where you've ended up cloning something from a competitor? Cause like, yeah, they figured something out good.
7:49 Speaker 00 Yeah, actually, um, 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, fix them. It was particularly brutal, honestly, because I was like, oh yeah, they just listened to our customers better than we did. And so that, we were like, okay, like that needs, that needs to stop right now.
8:07 Jack Altman? Yeah, totally.
8:08 Speaker 00 Yeah.
8:08 Jack Altman? 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. Those still like the best billboard I've ever seen.
8:25 Speaker 00 Zaster 2021 was its debut.
8:28 Jack Altman? It's crazy.
8:28 Speaker 00 Yeah.
8:28 Jack Altman? Keep it going.
8:29 Speaker 00 Yeah.
8:30 Jack Altman? Yeah.
8:30 Speaker 00 That billboard's locked up for.
8:31 Jack Altman? 10 more years.
8:32 Speaker 00 Like, kind of, actually.
8:33 Jack Altman? I love that.
8:33 Speaker 00 Yes.
8:34 Jack Altman? But like, what have you learned in sort of like the way that you structure your go to market? When you're, I mean, most markets are really competitive, but like, what have you learned?
8:40 Speaker 00 Yeah, I think one bit is like, man, A confidence is so real. And not as rational as like a EPD person, like a engineer or PM would imagine.
8:50 Jack Altman? Yeah.
8:51 Speaker 00 And that works on the way up and it works on the way down. When the team is starting to lose confidence, like you gotta 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. And but then it kind of becomes this like, how do you build confidence amongst your salespeople?
9:07 Jack Altman? How do you build it?
9:08 Speaker 00 What we did, and this is all credit to our CRO Stevie, was one of the, 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. 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 listened to all the call or like they were in all the calls. They talked to all the customers, they talked to like rip customers in both directions. And they just got smart about what was going on.
9:46 Jack Altman? Yep.
9:47 Speaker 00 And they figured out the talking points and the weak points and all of that. And then they got confident in winning and it was one or two people. And then we started adding them to everybody else's calls. And then like A8 would be like, oh, I want that person to come join.
9:59 Jack Altman? Show the confidence, yeah.
9:59 Speaker 00 Exactly. And like, when I add them, I win more. So like definitely want them in.
10:03 Jack Altman? Yep.
10:04 Speaker 00 And then that like sort of osmosed out.
10:06 Jack Altman? That's brilliant.
10:06 Speaker 00 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.
10:16 Jack Altman? Yep.
10:17 Speaker 00 But like salespeople learn from salespeople and everyone else is, you know, not as good. Doesn't matter like who you are or what you're trying to do.
10:23 Jack Altman? Yeah, totally. Um, I want to go over to fundraising. I guess you started fundraising at your seed in, when was it? Two thousand eighteen?
10:32 Speaker 00 Mm hmm.
10:32 Jack Altman? Is that right?
10:32 Speaker 00 April eighteen.
10:33 Jack Altman? April eighteen. 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.
10:40 Speaker 00 Yes.
10:41 Jack Altman? Can you just talk about like some of the stuff you did? I know we've talked about this before, but like, can you talk about in that period? How you made most use of that time?
10:48 Speaker 00 Yeah, so I think so for the seed, what we did was 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.
11:00 Jack Altman? Yep.
11:01 Speaker 00 Crazy thing and didn't want to choose a board member. And like, that just felt silly. Board members are like harder to get rid of than, you know. Execs, co-founders, right? Like, 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 A firms. And we're like, hi, just interesting, Vanta, we just raised. No opportunity for you to hear. Just want to say hi and like, put the first, like, put the first dot on the map.
11:25 Jack Altman? Like, right after the round?
11:26 Speaker 00 Right after the round.
11:27 Jack Altman? Like, within weeks, kind of thing?
11:28 Speaker 00 The one week.
11:29 Jack Altman? Wow.
11:29 Speaker 00 It was like, schedule all of them, but just schedule them after it's done.
11:32 Jack Altman? Wow.
11:33 Speaker 00 And so just like, just to be my-
11:34 Jack Altman? Someone gave you advice to do that?
11:35 Speaker 00 Yeah, and it's like, putting, putting myself on the map, you know? Nothing for you now, but like, here you go.
11:39 Jack Altman? 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.
11:48 Speaker 00 Yes.
11:49 Jack Altman? Yeah.
11:49 Speaker 00 So did that. And then it was like, I obviously, there was this moment of like, shit, we just like, raised three million dollars to do all this stuff. And we have, you know, two people sitting on a couch, like, we gotta, gotta, we gotta get, we gotta get hopping.
12:00 Jack Altman? Yep.
12:00 Speaker 00 So there was some amount of just that. And then at some point, six months later, you're like, okay, this is work. Like, this is different. Vanta 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. There's a million things wrong, a million things going on, but like, there's something here. And then, did not really talk to VCs. I think what started happening was there was like, some amount of word of mouth amongst San Francisco founders about like, hey, if you want to stock to, there's this Vanta thing. We had this call response of like, stock to Vanta going. It would start to come up with these companies' VCs. They would start to talk to us. And look, it was like, half I was playing a game and half was actually really busy.
12:44 Speaker 00 But I generally reply and be like, look, I am just too busy fielding customer calls.
12:48 Jack Altman? Yeah.
12:49 Speaker 00 Because I kind of was, like, I don't have time to meet with you, but it sounds like you know, you know, this founder at this company, you can go talk to them.
12:58 Jack Altman? Yeah.
12:59 Speaker 00 And like, look-
13:00 Jack Altman? An existing customer.
13:01 Speaker 00 An existing customer.
13:01 Jack Altman? Yeah.
13:02 Speaker 00 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, 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.
13:14 Jack Altman? Right.
13:15 Speaker 00 Like, that is better diligence and information than I could ever.
13:18 Jack Altman? Yeah. If you want to see if Vant is good, go try to send us a customer, see if they close and then see if they're happy.
13:22 Speaker 00 Yeah. And it's like, that is better than anything.
13:24 Jack Altman? And that happens.
13:25 Speaker 00 Amazing. Which, that worked very well.
13:28 Jack Altman? Yeah.
13:28 Speaker 00 You know, and I do think there was like a game, but I couldn't call it a game because I was a bit of like, oh, no, sorry. I'm just too overwhelmed by like, you know, customers and dollars.
13:35 Jack Altman? And there's an implied dynamic in there of if you want to get time with me, send me a lot of customers.
13:39 Speaker 00 Yes.
13:39 Jack Altman? Yeah.
13:39 Speaker 00 And you have to kind of be careful to not sound like total jerk.
13:42 Jack Altman? Yeah.
13:42 Speaker 00 Yeah. Cause 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 and.
13:49 Jack Altman? Yeah. Well, part of why that thing works is because that's an incredibly confident dynamic for you to be running.
13:55 Speaker 00 Yes.
13:55 Jack Altman? Yeah. Which helps.
13:56 Speaker 00 Which helps. And I think, you know, I think one of my pieces of advice for founders is investors are not people you should seek approval from. They want to back people who are confident in what they're doing.
14:07 Jack Altman? Yep.
14:08 Speaker 00 Not people who are seeking their approval.
14:09 Jack Altman? And it's really hard. There's a real dynamic where founders want investors approval.
14:13 Speaker 00 Yes.
14:13 Jack Altman? 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.
14:23 Speaker 00 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 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.
14:42 Jack Altman? Yeah.
14:42 Speaker 00 And not look up and be like, is this right? Am I on the right trail?
14:45 Jack Altman? Yep.
14:45 Speaker 00 And so then I think it's like, okay, as a founder, how do you get that? And some people can just kind of 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.
14:56 Jack Altman? Yeah.
14:56 Speaker 00 But like, it sort of doesn't matter. It's like, as long as you are, you are confident in the way you get confident doing that. And that makes the founder 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.
15:09 Jack Altman? So what ended up happening at your series A or the round when you picked a board member?
15:14 Speaker 00 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. I remember I did some of them over the holidays because it was like customer or email. Like I just had time or time and had this whole thing and then literally ended up choosing an investor and board member who was on the spreadsheet and like fell off the framework.
15:36 Jack Altman? How'd that happen?
15:37 Speaker 00 I was not going to talk to Sequoia 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.
15:50 Jack Altman? Yep.
15:50 Speaker 00 They were like very politely entirely uninterested and just like, nice girl, bad idea. Maybe she'll work at one of our companies one day, you know, and they were like, they didn't quite say that. But it was like totally the vibe.
16:02 Jack Altman? That was the vibe.
16:03 Speaker 00 Totally.
16:03 Jack Altman? Were they sending you customers or they weren't?
16:05 Speaker 00 No.
16:05 Jack Altman? They were not playing along the back end?
16:06 Speaker 00 No, zero. They were just like, I wonder when that company's gonna die.
16:10 Jack Altman? No.
16:11 Speaker 00 Very politely though. And so I 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 a close friend of both of us who was like, you're being an 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.
16:35 Jack Altman? Yep. 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.
16:47 Speaker 00 Sometimes some of them. I think VCs, I mean, at their best, like all of us, 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. They're probably not good at running companies. Or if they are and are now doing like,
17:07 Jack Altman? And I could have run your-
17:08 Speaker 00 No, they've now chosen to do something else and like don't want to run your company.
17:11 Jack Altman? Right, yeah.
17:11 Speaker 00 You can just make this better than I can.
17:13 Jack Altman? Yeah, and they probably couldn't run your specific company anyway.
17:16 Speaker 00 Right.
17:16 Jack Altman? Yeah.
17:16 Speaker 00 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 writing leads under a couch cushion, what do you do? Like, that is not DC stuff.
17:30 Jack Altman? Yeah.
17:31 Speaker 00 Almost universally. Or if it is, I guess Andrew not like super, super early stage or some special thing, like something's probably off.
17:38 Jack Altman? Right. Well, they're probably capable at giving you an answer to that. It's actually, I would think it's more like you probably shouldn't need to, you probably should have other vehicles to get that stuff.
17:47 Speaker 00 Right. I think recruiting support, especially in the early days.
17:52 Jack Altman? Yeah. When you say recruiting support, do you mean sending you candidates or do you mean closing candidates?
17:57 Speaker 00 I more mean closing candidates. There's some sending of candidates, but I do think that is like-
18:01 Jack Altman? Do you find the sending of candidates helpful? Or do you think the closing is what's all that?
18:04 Speaker 00 Tomato, tomato. Yeah.
18:05 Jack Altman? Yeah.
18:06 Speaker 00 Yeah. I mean, like, there's some stuff there and, but I think in the early stages and it's like Sequoia's model is like, okay, we'll send you candidates up until this point and then we will basically cut you off.
18:14 Jack Altman? Did you get candidates from that? I mean, did you get hires from that?
18:19 Speaker 00 Very rarely.
18:19 Jack Altman? Yeah.
18:20 Speaker 00 Yeah.
18:21 Jack Altman? Yeah.
18:21 Speaker 00 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, okay, you were like one in the like cohort, but like, how are you differentiated? And do they, you know, like, there's, those are hard candidates.
18:35 Jack Altman? 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.
18:42 Speaker 00 Hmm.
18:42 Jack Altman? I'm curious what that played out like for you.
18:44 Speaker 00 Yeah, so I think in the early days, there is a bit of like the brand and the like, oh, you know, here you have person from Sequoia who's, you know, legendary firm from, you know- Founding IPO would be whatever, you know, and like, let me tell you why Vanta is going to be the next thing we put on the wall.
18:59 Jack Altman? Yep.
18:59 Speaker 00 And of course, I, you know, I can say that, but like, is, 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 you can use, 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.
19:17 Jack Altman? It's just professional sales, basically.
19:18 Speaker 00 Yes. And there's like a lot of more practice.
19:21 Jack Altman? Yep.
19:21 Speaker 00 A little bit of candidate support.
19:23 Jack Altman? I've actually never heard someone say it quite like that, but I think that's true.
19:25 Speaker 00 You just like practice that more.
19:26 Jack Altman? Founders are also closing all the time, but it's like all VCs do.
19:29 Speaker 00 Right.
19:29 Jack Altman? Yeah, you're right.
19:30 Speaker 00 Yeah. As much as I kind of, we talk about this, like, hate it and it offends the, like, rational person in me, like VC brand matters.
19:38 Jack Altman? Yeah. Do you think that's the top thing?
19:39 Speaker 00 Yeah.
19:40 Jack Altman? You think it just sprinkles a little fairy dust on everything and helps like self fulfilling prophecy?
19:43 Speaker 00 I think just like, it's like all your conversion rates at every stage just gets slightly better.
19:47 Jack Altman? And this is for like candidates, for customers, for the next funding round?
19:50 Speaker 00 For media, yeah. It's like, everything just gets 10 to 30% better.
19:54 Jack Altman? Once you had Sequoia, did it make recruiting a lot easier?
19:57 Speaker 00 Yes, in a way that we talk, but like, yes, in a way that I was like, kind of annoyed by, but like.
20:01 Jack Altman? What's the dynamic?
20:02 Speaker 00 We'd have, I don't have like a literal person, but you know, we'd have candidates and we'd like approach them and, uh, you know, Vanta's a little funny because we raised our Series A at 10 million, but 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? And where I see, and someone would be like, no, you know, and then like, and then like the next day, yeah, no, like have fun over there.
20:23 Jack Altman? Next, yeah.
20:23 Speaker 00 Yeah. And then like the next day, we like announced the Series A from Sequoia, like 50 and 500. And then like the following day, we like followed up.
20:30 Jack Altman? Everyone's in your mind.
20:31 Speaker 00 Yeah, exactly. And you're like, we are the same company.
20:33 Jack Altman? Right. Except now you have a higher foreign name.
20:35 Speaker 00 Exactly. Like now it is a worse economic deal for you.
20:37 Jack Altman? Yeah, right.
20:38 Speaker 00 But like, if you want to outsource your judgment to Sequoia, like, I guess I'm here for it.
20:41 Jack Altman? Yeah, right. Did you experience it as like a one time pop? Or have you experienced it as like a durable lift?
20:47 Speaker 00 Durable. And again, a way that I think I wouldn't have expected, but the 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.
21:03 Jack Altman? Just dominates.
21:03 Speaker 00 Yeah.
21:04 Jack Altman? 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?
21:12 Speaker 00 No, on the recruiting sense, we get back channels and sometimes have, you know, their team. You know, sort of, they are very good at knowing sort of everyone in the valley.
21:21 Jack Altman? Yeah.
21:22 Speaker 00 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.
21:30 Jack Altman? Someone on the team knows.
21:31 Speaker 00 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 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 our conference together and they like.
21:50 Jack Altman? Yeah.
21:50 Speaker 00 We got on the conference stage because of Andrew, you know, because of Sequoia, right? And I was just like the tag along.
21:54 Jack Altman? Yep.
21:54 Speaker 00 But there was some of that where that helped too.
21:57 Jack Altman? 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? But like, if you go back, you know, and you think about like how you recruited when you were a seed or series A company.
22:15 Speaker 00 So bad.
22:16 Jack Altman? I guess something changed. Yeah, basically.
22:17 Speaker 00 I think in the early days, we were trying to be very frameworks driven and rigorous and everything was bespoke.
22:24 Jack Altman? Like your VC spreadsheet.
22:25 Speaker 00 Exactly. Yes.
22:26 Jack Altman? Yeah.
22:27 Speaker 00 And it's like, you know, there's a little bit of like, you hire like the first person in every role. So every role is distinct.
22:32 Jack Altman? Yeah.
22:32 Speaker 00 But we had had these like crazy, like multi-day interview loops that were like, we would send someone through a, I don't know, tough mutter, you know? And like, wonder why candidates dropped out.
22:42 Jack Altman? Yeah.
22:42 Speaker 00 And you're like, well, that's because we asked them to like, I don't know, do an obstacle course.
22:46 Jack Altman? Uh huh, uh huh.
22:46 Speaker 00 And we'll say the people who got through, like, man, were they down.
22:48 Jack Altman? They really wanted to join, yeah.
22:50 Speaker 00 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.
22:58 Jack Altman? Yep.
22:59 Speaker 00 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 talked to someone last night about this. And then you like figure out engineering recruiting for a bit and then something changes.
23:11 Jack Altman? What changes? Inside the company or in the market or what?
23:14 Speaker 00 Both. Well, again, to the example, we for years just hired generalists. And then like 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 know Mongo. We use GraphQL, that technical solution, whatever. We need people know GraphQL, you know, and like, we should have these like separate pipelines.
23:34 Jack Altman? In a way that this doesn't happen in design or sales or marketing? Cause like the tech stack changes in.
23:39 Speaker 00 You know what? I think what it is, is like engineering recruiting, I mean, is just harder than all the other roles.
23:45 Jack Altman? Yeah.
23:45 Speaker 00 And that timelines are longer. And so when you break the pipelines, you just.
23:49 Jack Altman? Yeah.
23:49 Speaker 00 It takes longer to get them stood up again.
23:51 Jack Altman? Did you do work trials?
23:53 Speaker 00 At that, yeah.
23:54 Jack Altman? You don't now, right?
23:55 Speaker 00 We don't.
23:55 Jack Altman? Yeah.
23:56 Speaker 00 We don't now. We do our general, 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.
24:07 Jack Altman? Hmm.
24:07 Speaker 00 And the project is usually like, so uh, we dumped the Google, do I have a 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 or opt out.
24:24 Jack Altman? Yeah.
24:24 Speaker 00 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 team. What do you think?
24:39 Jack Altman? Oh, wow. And you're trying to see like, can they tell from the Gong calls?
24:42 Speaker 00 Kind of. And also like, this is literally the team you're going to get handed.
24:45 Jack Altman? Yeah.
24:46 Speaker 00 Like, if you wanna, if you don't like this, like, let's just get that out now.
24:49 Jack Altman? Yeah.
24:49 Speaker 00 Like, and so we don't have to, you know, be like, oh, we're bearing skill sets on the team. You know, you're like, here they are.
24:53 Jack Altman? Yep.
24:54 Speaker 00 And like, again, this is, this is the, the range.
24:56 Jack Altman? Yeah.
24:57 Speaker 00 She stood out for many reasons, but part of it, she watched it and she's like, oh. Here's what I saw. Here's what we do, like, you know, like unfazed and like very clear eyed and broke it down.
25:06 Jack Altman? 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?
25:16 Speaker 00 Yeah. So actually back to the early days, we had a principal's interview.
25:19 Jack Altman? Yeah.
25:19 Speaker 00 You know, Vanta interview and 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, Chris, you know, you were spending too much time on this. Stop doing it.
25:31 Jack Altman? Yep.
25:32 Speaker 00 And so I like distributed it. I should not have done that. I think you should go through two, maybe three team interventions.
25:38 Jack Altman? Yeah.
25:38 Speaker 00 Not the first one.
25:39 Jack Altman? Yeah.
25:39 Speaker 00 You don't give it up after the first, at least the second.
25:42 Jack Altman? Yep.
25:42 Speaker 00 So I should have hung on to that a little bit longer.
25:44 Jack Altman? Like hang on till it's 200 people, you think? Like when, when do you think it's like, what's your now assessment of like when it's like enough is enough?
25:51 Speaker 00 When you're spending probably more than a day and a half of your five days.
25:54 Jack Altman? Yeah.
25:55 Speaker 00 On it.
25:55 Jack Altman? And when did that come for you?
25:56 Speaker 00 See, I didn't get there because I capitulated after the first intervention.
26:00 Jack Altman? I see.
26:00 Speaker 00 Which is probably like three quarters of a day.
26:02 Jack Altman? Got it. Okay.
26:02 Speaker 00 Yeah.
26:03 Jack Altman? So maybe you could have gone twice as far.
26:04 Speaker 00 Yeah, I think you should like at least wait for two interventions.
26:06 Jack Altman? Yep.
26:06 Speaker 00 But then what I started doing six or nine months ago is now I do do that for every director plus candidate. So I like reinserted.
26:13 Jack Altman? And they can't get in without your blessing?
26:15 Speaker 00 I'll do non-blocking nos.
26:17 Jack Altman? Yeah.
26:17 Speaker 00 And they're truly non-blocking and it's like, here's what I saw.
26:20 Jack Altman? Yeah.
26:20 Speaker 00 If you is the manager.
26:21 Jack Altman? I wouldn't do this, but I'll support you.
26:22 Speaker 00 Yeah. And like here are the gaps and like if you as the manager like think you got this, cool, I will hold you to that. But if you want to make this call, like.
26:30 Jack Altman? When you do that, does it usually go through or not go through?
26:33 Speaker 00 Yeah, it's a good, it's like, are they actually non-blocking?
26:35 Jack Altman? Yeah, exactly. Or are people like, I probably shouldn't do it.
26:37 Speaker 00 Usually like I shouldn't do it.
26:38 Jack Altman? Yeah.
26:39 Speaker 00 But more of them should go through. Yeah.
26:40 Jack Altman? Has it ever happened?
26:42 Speaker 00 Yeah.
26:42 Jack Altman? That it's gone through?
26:43 Speaker 00 Yeah.
26:43 Jack Altman? And then it's been good?
26:44 Speaker 00 Yeah.
26:44 Jack Altman? Yeah.
26:44 Speaker 00 Totally.
26:45 Jack Altman? Yeah.
26:45 Speaker 00 Yeah, yeah, yeah, totally.
26:46 Jack Altman? Yeah, that's a good sign.
26:47 Speaker 00 Yeah.
26:47 Jack Altman? Yeah.
26:47 Speaker 00 No, more people should like, yeah.
26:49 Jack Altman? 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. 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?
27:06 Speaker 00 Pretty different.
27:07 Jack Altman? Yeah.
27:08 Speaker 00 Um, cause 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've 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. Anyway, so there's like a whole thing there that I just like don't care about when you're angel investing.
27:27 Jack Altman? Right.
27:27 Speaker 00 Cause 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 in the universe.
27:32 Jack Altman? Basically the culture, there's no culture interview. It doesn't matter.
27:33 Speaker 00 No.
27:35 Speaker 00 No.
27:35 Jack Altman? Does that make it easier then? Because at Vanta, you need to both be good and you need this.
27:39 Speaker 00 I think so. Yeah.
27:40 Jack Altman? So you'd invest in somebody before you hired them, basically?
27:43 Speaker 00 Yeah.
27:43 Jack Altman? Yeah.
27:43 Speaker 00 Totally.
27:44 Jack Altman? Yeah.
27:44 Speaker 00 Cause 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, it's a like meta version of the, the Gongcall. Sales example is like, people should just know what they're opting into.
27:56 Jack Altman? Yeah.
27:57 Speaker 00 And we tried to do that in our review process and be like, this can be for you or can not be for you, but here's what it is. And it's kind of not immovable, but like it's not going to turn 180 degrees.
28:05 Jack Altman? Yeah.
28:06 Speaker 00 Whereas like somebody can build a company in a totally different way.
28:08 Jack Altman? Have you basically learned that a talented person who doesn't fit the culture, just it doesn't work out anyway?
28:13 Speaker 00 Yes.
28:13 Jack Altman? Like you've tried it and it just doesn't go the way you want it to.
28:15 Speaker 00 Yeah.
28:16 Jack Altman? Or on either direction.
28:17 Speaker 00 Yes. And so I think, you know, one of the things, and 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.
28:28 Jack Altman? Yeah.
28:28 Speaker 00 Some of it works, some of it doesn't, but like that's, I do think we owe that to candidates.
28:32 Jack Altman? 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, bull run. Great. And then the world's all AI, everything, everywhere, all the time now. And so I'm curious how you've 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?
29:04 Speaker 00 There is a lot of. Hopefully like AI encouragement and excitement across the company. And that is both in 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?
29:28 Jack Altman? Yeah.
29:28 Speaker 00 And so it's like, okay, how do you, how do you bring those together? Um, and like, 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.
29:41 Jack Altman? 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?
29:46 Speaker 00 I think it matters a ton for our product. Because so much of compliance is taking information in one format and putting it in another.
29:52 Jack Altman? Yeah.
29:53 Speaker 00 Right? Like actually, and so there's just, and like, I think the pieces of compliance will not change. But like, will you have to, you probably, you were, Eric, kind of like write your own policy documents. Isn't that like kind of, you know, you're like, yeah, and you also use a carrier.
30:05 Jack Altman? Yeah, at least copy paste them and hope they're right or something.
30:07 Speaker 00 Exactly. Yeah, yeah. And then you're like, if you had, if you want to know what was in them, you had to read them.
30:10 Jack Altman? Yeah, that's crazy. Yeah, now you can just get the summary.
30:12 Speaker 00 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.
30:17 Jack Altman? Yeah.
30:18 Speaker 00 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.
30:27 Jack Altman? How much AI are you consuming? Just like other AI products, just to run your company differently across everything?
30:33 Speaker 00 We're, we're in an AI procurement boom. I hope I don't say this in a million emails.
30:37 Jack Altman? Yeah.
30:37 Speaker 00 Yeah, but a little bit. We used to be much stingier and I think.
30:41 Jack Altman? If you're selling an AI product, here's Christina.
30:42 Speaker 00 I know. Christina and Vanta.com. Please don't. But I think the thing we have actually, like now it's a large enough company where you have to somewhat be thoughtful here. And 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 is like IT kind of runs and be like, okay, now we all come together and be like, oh, we bought five meeting recorders.
31:05 Jack Altman? Right.
31:05 Speaker 00 Cool.
31:06 Jack Altman? Let's pick one.
31:07 Speaker 00 Figure it out. And but like do that incrementally along the way.
31:10 Jack Altman? 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?
31:19 Speaker 00 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.
31:26 Jack Altman? Interesting.
31:27 Speaker 00 Yeah.
31:27 Jack Altman? Yeah.
31:28 Speaker 00 And like, again, I can like critique and be like, oh, we should think more like PMs and our procurement. And but like,
31:32 Jack Altman? Yeah.
31:33 Speaker 00 That is not where the effort goes.
31:34 Jack Altman? Yeah.
31:34 Speaker 00 Yeah.
31:35 Jack Altman? Yeah. Do you want to use basically as much as possible?
31:39 Speaker 00 Yes.
31:39 Jack Altman? Yeah, okay.
31:40 Speaker 00 Yeah, there was actually a, a, this is kind of a cute phrase, but we were going back and forth about how many chat GPT licenses we have. Cause chat GPT license were like kind of expensive and Gemini is free.
31:49 Jack Altman? Yeah.
31:50 Speaker 00 And like, so can we just like be stingy about chat GPT licenses and make everyone use Gemini basically? And the answer is no.
31:56 Jack Altman? It's not worth it.
31:57 Speaker 00 Yeah, well, so it's like unused chat GPT licenses are very expensive. Used ones are actually pretty cheap.
32:02 Jack Altman? Right.
32:02 Speaker 00 Right? And so it's like, okay, can you like get the energy focused on like getting the licenses used versus like being parsimonious about them?
32:09 Jack Altman? 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?
32:14 Speaker 00 Yeah.
32:15 Jack Altman? I'm going to ask it a different way. What pieces of software 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?
32:25 Speaker 00 I think go to market systems is a Rube Goldberg machine constructed by like seven different tools.
32:33 Jack Altman? Yeah, that's what we had. And we had like nine biz ops people holding it all together.
32:36 Speaker 00 Exactly, yes.
32:37 Jack Altman? Yeah. And it was like, once it gets to that system, they're going to grab this ball and put it over here.
32:41 Speaker 00 Exactly. Exactly. And it's just kind of nuts because you're like, okay, if this were engineering, like, or this does not exist in engineering.
32:48 Jack Altman? It would be unacceptable.
32:49 Speaker 00 It would be entirely unacceptable. It was unacceptable a decade ago.
32:51 Jack Altman? Yeah.
32:51 Speaker 00 And so like, someone should fix that.
32:53 Jack Altman? Yeah. Can you say a little bit more about the, like, can you, you don't have to name the vendors, but like, name the parts of, like, maybe the parts of the funnel you're talking about.
33:00 Speaker 00 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 sales rep or how does that get to closed one? And like, oh, man, we got, we got the ball, the balls are going into the tubes or onto the floor.
33:16 Jack Altman? Yeah, I never understood why it had to be so messy. Like, I get that it's kind of complicated and.
33:20 Speaker 00 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.
33:26 Jack Altman? Yeah.
33:26 Speaker 00 Kind of nuts.
33:27 Jack Altman? Okay, that's good. What else?
33:28 Speaker 00 Um, collections, contract terms. It is like the least favorite part of everyone's job, including the, like, the art customers, right?
33:36 Jack Altman? You'd think AI would be really good at that.
33:37 Speaker 00 Yes.
33:38 Jack Altman? Like parsing the document, doing the perpetual reach outs to people.
33:41 Speaker 00 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, oh, and then it's like heightened emotions and like, oh, boy.
33:51 Jack Altman? Yeah.
33:51 Speaker 00 Support kind of, or like the, like. Something is not working or.
33:56 Jack Altman? In support?
33:57 Speaker 00 Yeah.
33:57 Jack Altman? Customers, just regular customer support. You're saying that the chatbots are not working well? Is that what you're saying?
34:03 Speaker 00 Some of them.
34:04 Jack Altman? Yeah.
34:04 Speaker 00 Yeah. Or I think we have some of that. And then I think we have.
34:09 Jack Altman? Or is it the tooling around them and like the reporting on it? Is that the issue?
34:12 Speaker 00 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 Vanta tone of voice. We call it Elma Bach because Elma is our mom's name. But you know, it's like our, our copywriters can only do so much. And so how do you kind of Vantify the writing? And I think that's works very well for marketing copy. I kind of want it for like all support tickets.
34:32 Jack Altman? Yeah.
34:33 Speaker 00 And honestly, like all customer columns.
34:35 Jack Altman? Yep. Do you think sales will get AI-ified?
34:39 Speaker 00 Somewhat, I think there will be reps, but like even like we actually, I think are quite good at enforcing sales force hygiene amongst our 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.
34:57 Jack Altman? Yeah.
34:57 Speaker 00 Cause that's what they're supposed to go execute on.
34:59 Jack Altman? Have you had any luck with like AI SDRs?
35:01 Speaker 00 No, we haven't really tried. We tried a little bit, but we haven't, we're not a good.
35:04 Jack Altman? Yeah.
35:05 Speaker 00 Still walking up the like hierarchy of SDR tooling.
35:07 Jack Altman? Yeah. What else? Anything in like security or operations or anything like that?
35:10 Speaker 00 I think that like security operations center and the like other SOC.
35:14 Jack Altman? SOC.
35:15 Speaker 00 Yeah.
35:15 Jack Altman? That's confusing. That's frustrating.
35:17 Speaker 00 Space, you know, like the old way to solve that is put a bunch of people in a room, maybe in your company, maybe outsource that like look at alerts all day.
35:24 Jack Altman? Yeah.
35:25 Speaker 00 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 the rule writing phase. How do we just AIify 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.
35:42 Jack Altman? Yeah.
35:43 Speaker 00 And so how do you do that?
35:45 Jack Altman? What about like marketing very top of funnel? And has anything like changed there?
35:49 Speaker 00 Like the LLM SEO stuff, whatever you call it, AI EO or whatever people call it. Yeah.
35:55 Jack Altman? Is that it?
35:55 Speaker 00 Yeah.
35:56 Jack Altman? I don't know.
35:57 Speaker 00 But like that thing.
35:58 Jack Altman? Yeah.
35:58 Speaker 00 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, but like overall seems like search volume is dropping and like we see that.
36:14 Jack Altman? That's crazy.
36:15 Speaker 00 In our SEM spend.
36:16 Jack Altman? That's really crazy.
36:17 Speaker 00 Yeah.
36:17 Jack Altman? And your assumption is basically that's all just gone to the LMS?
36:20 Speaker 00 Yes.
36:21 Jack Altman? Yeah.
36:21 Speaker 00 Yes.
36:22 Jack Altman? That's just like a whole new work stream, I guess.
36:24 Speaker 00 It seems like, and 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 rerun it the next day and you rerun it, you know? I'm sure someone will build a bot thing, but like, oh, boy.
36:42 Jack Altman? Is there anything else in like HR, like people stuff or anything in finance?
36:48 Speaker 00 Oh, we did something like, maybe moderately controversial and 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.
37:00 Jack Altman? Hmm, to, to help them give feedback?
37:02 Speaker 00 Yeah.
37:02 Jack Altman? Yeah, I think that's good.
37:03 Speaker 00 And yeah, because it's kind of like, I think my, I don't know, my general thing, you have much smarter ideas, but like my general thing on perf reviews, it's like 360 and perf reviews are super helpful if you actually do them.
37:13 Jack Altman? Yeah.
37:13 Speaker 00 If you kind of do it halfway, it just ends up taking 60 hours from everyone's time and being terrible.
37:17 Jack Altman? Totally.
37:18 Speaker 00 And so like, you know, you either need to go like all in or like all out.
37:21 Jack Altman? Yeah.
37:22 Speaker 00 And so how do you get it?
37:23 Jack Altman? My whole thing with, 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 are like, yeah, that is something I need to get better at.
37:47 Speaker 00 Yep.
37:47 Jack Altman? So however you get there.
37:48 Speaker 00 However you get there.
37:49 Jack Altman? Yeah.
37:49 Speaker 00 And like, get there and get it clearly articulated and like that thing.
37:53 Jack Altman? It's not so dissimilar from like the way a lot of consumers are using AI for like, kind of like borderline 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, here's an insight that's useful.
38:06 Speaker 00 Yep.
38:06 Jack Altman? Is worth a lot.
38:07 Speaker 00 Right, right. And like, I can read it and like, think about it and agree or disagree, but like,
38:12 Jack Altman? It has a condition.
38:12 Speaker 00 I got it.
38:13 Jack Altman? 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?
38:21 Speaker 00 Something like that, yeah.
38:23 Jack Altman? 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
38:30 Speaker 00 Yeah.
38:30 Jack Altman? turmoil in evolution, but like, what is the inner game journey that you've been through?
38:34 Speaker 00 Yeah, two things, the like trope of like a dozen could either 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, like I feel like I 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, I can do this now. Right. And the first time I was managing or managing a manager, I didn't feel comfortable. But like, I got, I did learn something.
39:06 Jack Altman? Yeah.
39:06 Speaker 00 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, I have a point of view here and I adamantly believe it. Maybe I'm wrong, but like, I've learned something.
39:17 Jack Altman? Yep.
39:17 Speaker 00 So there's some of that, even if in the day to day, you're like still in like, well, I've done this before, but here we go.
39:22 Jack Altman? Yep.
39:23 Speaker 00 And then I think there is a, all the like, there's like different types 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, you know?
39:34 Jack Altman? Some order.
39:35 Speaker 00 Some order.
39:38 Speaker 00 Product team company, now they say that out loud. And like, those are very different. And there's like, oh, a different types of people. You 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 not a joke. It's like, no, you just have to like Stockholm syndrome yourself into being like, well, I used to be someone who liked to build products, but now I love building teams.
39:58 Jack Altman? Right.
39:58 Speaker 00 And whether or not I identified as that person as two 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.
40:05 Jack Altman? Yeah.
40:06 Speaker 00 I love HR policy.
40:09 Speaker 00 Cause that's what the company needs right now.
40:10 Jack Altman? Yeah, totally.
40:11 Speaker 00 And like, you know, joking, but not like figuring out how to be like, this is the game and the puzzle and like the journey and I need to take joy in it. Cause otherwise I will just, you know, like be sad and burned out and unfulfilled. And like, this is not sustainable.
40:24 Jack Altman? Did you have a part of the journey where you? We're 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.
40:36 Speaker 00 Yes.
40:37 Jack Altman? Cause I imagine at the beginning.
40:38 Speaker 00 Yes.
40:38 Jack Altman? I mean, who doesn't love, I mean, everybody loves building a product. Everybody loves getting that early customer.
40:42 Speaker 00 Right.
40:43 Jack Altman? Like that stuff is just like objectively fun.
40:45 Speaker 00 Yes.
40:45 Jack Altman? And then there are things that are like debatably fun and some people might love them, but not everybody loves them.
40:49 Speaker 00 Yes.
40:49 Jack Altman? Yeah.
40:50 Speaker 00 And I think it's, and especially in the early days, cause like for me, the first version of this was, okay, we have this product and company and recruited a couple of engineers. Now I have to go like do all of go to market and both do it and recruit people.
41:02 Jack Altman? Yeah.
41:02 Speaker 00 And I didn't know how to spell go to market, like kind of actually. And so it was like, I gotta do this. Everyone else is counting me on to do it. I'm like, wow, am I bad at it?
41:10 Jack Altman? Yeah.
41:10 Speaker 00 Cause I've never done it.
41:11 Jack Altman? Yeah.
41:12 Speaker 00 And like kind of raking myself over the coals for that.
41:15 Jack Altman? Mm hmm.
41:15 Speaker 00 And then sort of being like, okay, right. I'm bad at it. Cause I haven't done it. My job is to get good fast.
41:21 Jack Altman? Yeah.
41:21 Speaker 00 Right. Like it's, it's trajectory, not, you know, anything else, but like kind of reframing that.
41:25 Jack Altman? 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 gonna 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? Cause I think very few people have that kind of ability to tell themselves that this is how I'm gonna feel about this thing.
41:48 Speaker 00 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 going to get a park and you're like, also when I get really frustrated or pissed off, I'd like go run.
41:58 Jack Altman? Yeah.
41:58 Speaker 00 Usually at some point there is like some, something, we have a mutual friend, Jay Zach Stein, who was like very, who I think is a very helpful like playback, sounds like what you're saying. Sounds like this is a thing, you know, like, uh, like prompting on self-reflection. And then I think also just talking to other founders, right? And then you talk 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 a nor and I'm unhappy and just kind of being like, oh, that seems bad, you know?
42:28 Jack Altman? Yeah.
42:28 Speaker 00 But like, I get it, right?
42:30 Jack Altman? 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.
42:34 Speaker 00 Thank you so much for having me.
Previous Uncapped #16 | Mamoon Hamid from Kleiner Perkins Next Uncapped #18 | Peter Fenton from Benchmark Page updated October 25, 2026 · transcript and summary are machine-generated
