Long Strange Trip: CEO to CEO with Brian Halligan
00:10:38 · Brian Halligan, Mati Staniszewski
[00:10:38] S2: And like, I finally have this kind of three types of CEOs, these people who are really in all the details in everyone's shorts all the time. Their CEOs are pretty high level and like I have an expression, keep your feet in the ground, your head in the clouds, or you're in the details and you're up high. Some people who stay very high. And then there's what I call spelunkers, people who kind of go down deep in one thing for a while, they come back out and go down into another thing. Have you got one of those models? What are you? It sounds like you're the first. [00:11:12] S1: I do like the details. I think similar like the, I think to how Anton mentioned that you operate is you do on the funding model. You want to understand the product. You want to actually work with the product all the time so you know how to actually use the product better than most. I'm trying to stay extremely detailed in what it is that we are shipping, how we're shipping it, how it works behind the scenes. So that's probably the key thing. I like your analogy of head in the clouds, I the feet on the think the thing that I'm trying and I think where the magic happens if you do it well is being able to zoom out and zoom in extremely quickly before those contexts. So you're able to understand the problem, zoom into the detail, you understand the detail. And then the next second, you need to go to another problem which requires the same activity. [00:12:05] S2: So a lot of context switching being a CEO.
00:12:05 · Brian Halligan, Mati Staniszewski, Anton Osika
[00:12:05] S2: So a lot of context switching being a CEO. [00:12:07] S1: Exactly. And you kind of need to be immediate in that. My co founder, who is the smartest person I know and is kind of leading the research work, in his case, he needs to go extremely deep for a very long time. So we frequently speak about this very different way of approaching the work where one is all about context switching, the other one is all about going as deep as possible. [00:12:31] S2: And how are you feeling about delegation? Is it natural to just delegate all this stuff? Or is it like, I want to be in the details? I had very hard time delegating. [00:12:42] S0: I think it's often the, ah, when I'm very impatient And like, there is some friction when I when there's many things that are feel very urgent and I know one thing, but maybe not all of the other ones. [00:12:59] S2: Are you driving people crazy? [00:13:01] S0: No, mostly no. Mostly they like me, feel where I'm coming from and actually this is coming from a good place. [00:13:08] S2: Okay, let's talk about team. You just hired a friend of mine to run sales. Yep. You're building out your team. How are you thinking about building out your team? Your senior team in particular. And then are you looking for people with high slope or high experience?
00:13:08 · Brian Halligan, Anton Osika
[00:13:08] S2: Okay, let's talk about team. You just hired a friend of mine to run sales. Yep. You're building out your team. How are you thinking about building out your team? Your senior team in particular. And then are you looking for people with high slope or high experience? [00:13:23] S0: Oh, that's a good question. I think like at this stage, there's some there's many things we just like need to be done very predictably. And because of all the opportunities that are out there, and hiring people who have done it before, and are maybe wouldn't be as effective early stage, because they're accepting their ways, that is very effective. That is very effective. [00:13:51] S2: Oh, wait. So you lean towards experience, not necessarily [00:13:53] S0: For things that have to get done, we know like what those things are. [00:13:56] S2: Okay. [00:13:57] S0: It is effective to buy. Like what? So for sales, everything that comes up goes down to sales, a lot of some functions of marketing that has like all of this [00:14:05] S2: You're looking for experience there. [00:14:07] S0: I'm looking for experience. And then, so at least to run them. And then, one, if you have capacity to also hire people with high slopes and who are like generalists, you also find a good way to be able to move them around in the company, that's something that has worked really well for us. I cannot predict how it's going to work when there's more structure in the company, but I'm committed to finding a good experiment. Any these high slope generalists
00:14:07 · Anton Osika, Brian Halligan
[00:14:07] S0: I'm looking for experience. And then, so at least to run them. And then, one, if you have capacity to also hire people with high slopes and who are like generalists, you also find a good way to be able to move them around in the company, that's something that has worked really well for us. I cannot predict how it's going to work when there's more structure in the company, but I'm committed to finding a good experiment. Any these high slope generalists [00:14:36] S2: who you're moving around on your senior team, direct reports senior team? [00:14:39] S0: To senior [00:14:40] S2: team. Are any of your direct reports any of these? Currently. No high slope people moving around? [00:14:47] S0: Not on my actual leadership team, but many of the ones I work with day to day who like to feel like they're reporting directly to me on many things are more of the high slope. How [00:14:57] S2: about you on the team? You've got a few 100 employees, you're less than 100. What do you think about the senior team? What are you looking for? Have you had any misfires?
00:14:57 · Brian Halligan, Mati Staniszewski
[00:14:57] S2: about you on the team? You've got a few 100 employees, you're less than 100. What do you think about the senior team? What are you looking for? Have you had any misfires? [00:15:07] S1: In our case, have over 300 people, but inside of the company, it's effectively a lot of small teams. It has 30 teams of five to 10 people. And it usually is a combination of depending on the space, either few with the past work in that space, and then usually infused with some of the high slope. And we like that because, A, you get the generalists that can adopt a lot of the new tooling and kind of do new work. And second, we try to bring out the engineers across in some of those teams. So even in traditional growth team, we have growth engineers and the ops team will have operations engineering to help automate a lot of the process. Sometimes use Lovable in the process to help with that work. And that has helped tremendously to get the experience, the domain expertise while creating the new process. Across the leadership, so then all those teams roll up to each effective lead. So we have a go to market leads, then the engineering leads. [00:16:08] S2: How many direct reports do you have? [00:16:10] S1: I have 15 direct reports. [00:16:12] S2: That's a lot. Okay. And that crew of 15, are they kind of young, hungry, grow up at the company high slope? Or are they kind of been there, done that?
00:16:12 · Brian Halligan, Mati Staniszewski, Anton Osika
[00:16:12] S2: That's a lot. Okay. And that crew of 15, are they kind of young, hungry, grow up at the company high slope? Or are they kind of been there, done that? [00:16:23] S1: Almost exactly half half. So half half have done it before, usually are growing with their role. Of course, are growing extremely quickly. So we grew from... We started 2022 from zero to now over $200,000,000 in revenue. So that growth has been quick for everybody, so everybody's learning at the same time. But half of them have seen that before and the other half [00:16:43] S2: Do think that's right? Yeah, I have fiftyfifty. Like at HubSpot, we were kind of the same. I was, I'd look around the table about half grew up with the company, very high slope and half had a lot of experience. That felt right to me. Does that feel right to you? [00:16:59] S1: It does. In many ways, the people that are there have grown with the company incredibly. Victoria, who leads our ops team, has never done anything like this before. And also from Palantir background, so also physics background, so trying to create a process as we go across and has grown incredibly with the company. And then others kind of are still super important for the company, but will stay in more of the product teams or on the IC roles in other parts. [00:17:27] S2: How about you on the on the... You know, what's your mix of kind of homegrown and been there, done that? You're probably just starting to hire execs, I guess, from the outside. [00:17:36] S0: Yeah. So I built out this this leadership team, which is like seven people with my