Second in Command: The Chief Behind the Chief with Cameron Herold
00:14:52 · Gaurav Agarwal, Cameron Herold
[00:14:52] S0: Yeah. Yeah. I mean, I think if I if I see what separates the the legendary businesses, like, the reason why Facebook is what it is is because they have they have preserved their entrepreneurial DNA. So because in a world that's rapidly changing around you, the product behaviors, the UX patterns, the distribution paradigms, The only way you survive and and continue to manage your edge is by being entrepreneurial. [00:15:16] S2: So you have the engineering background, and engineering tends to be a little bit more structured, a little bit more methodical. You have a banking background, which which which is fairly entrepreneurial in many ways, it's fast paced, and it's definitely, like, quick thinking and problem solving and good analytics. But does the engineering get in the way of being entrepreneurial, or how have you found the marriage between those two? [00:15:37] S0: Actually, no. In the sense that I went to school for something called industrial and engineering and it's called management science and engineering in The US in some programs. It's also about operations engineering. [00:15:47] S2: Okay.
00:15:47 · Cameron Herold, Gaurav Agarwal
[00:15:47] S2: Okay. [00:15:47] S0: But the biggest thing I learned in that engineering curriculum was structured problem solving, number one. So how do you take a big problem and you break it down into systems? And then you identify the points of leverage. So good engineers are great at breaking down a problem or an opportunity into its subcomponents and identifying the points of leverage. And the second thing that I learned a lot is, there's always a better global optima out there. So wherever we are today, we are at a local optimum. And to assume that we will stay here is basically losing out on the fact that there's a bigger, better world out there that we can create because every engineering system has a better optimal state that you can get to. So if it bring these two things together, I think businesses are the same way where you... In order to run a business effectively, you need to understand the systems and the and the relationship between these systems, but then also identify real points of leverage. And if you can apply the pressure in these points of leverage, you will have a significant ROI versus beating your head against points that may have saturated. And then the third part, which is why I think entrepreneurial mindset is needed because businesses by default are are never at global optima. The world around you is constantly changing. So you are stuck in local optima. And if you behave like that, it keeps you humble, and it allows you to continue to push to keep that search for global optima.
00:17:13 · Cameron Herold, Gaurav Agarwal
[00:17:13] S2: Interesting. Now you've been there for... At ClickUp for just under three years right now. What was the size of the company approximately headcount when you got there? [00:17:22] S0: About 800. [00:17:23] S2: Okay. So 800 to a thousand. So it was still already a mature company. What was it like coming into the org? Did you come in as the COO? [00:17:31] S0: I I came in as the chief growth officer, primarily responsible for the self serve business. [00:17:36] S2: And chief growth officer, is that, like, marketing sales, or what was that? [00:17:40] S0: Okay. Had under my remit marketing, data, and some elements of product that directly touch, our growth numbers. [00:17:50] S2: Okay. So same question then slightly different, but same question. When you're coming into an organization that's already got 800 people, you're coming in at a c level, like, a very senior role over top of a whole bunch of people who have already been there, some of whom wanted your job, some of whom, you now get to report to you, but they don't know who the heck you are. What do you think, what did you do well coming into that, and how did you how did you come into that role kind of in your first ninety days?
00:18:19 · Gaurav Agarwal
[00:18:19] S0: I'm big, and I coach this to every exec who's taking on a new job that it's really important to to acknowledge the fight that the man in the arena has. I see a lot of people come in and they come in as spectators saying this could have been better, that could have been better, but that doesn't help anyone. So in my first ninety days, way I looked at it is I came in, keep your head down, learn from everyone, but then try and get as many wins as you can. So in the first ninety days, I was able to shift a lot of our marketing programs and unlock ROI immediately. And I I do this. I... This is a hack that I followed. In the first thirty days, go deep in the data and force yourself to do a presentation for for the leadership team. And in that presentation, if you do not share unique insights and unique points of view that that the leadership would be impressed by, then you have failed. So I force myself to do that all the time. And what that does is in the first month itself, end up building a very deep data driven view of the business. And then I'm able to present back and identify the points of leverage and chat about it. And what it does is in the first thirty days, it allows me to build a lot of trust with my peers that, yes, this guy gets it. He's not just shooting from his hip. He has seen the data. And oftentimes, in in the past three roles, I've been able to show something that everyone else would be like, wow. We didn't even know this happened. So that allows me to build instant credibility. So come in in the first ninety days, came in with a growth mindset mindset to absorb, be a sponge, learn all the context I can, Do that thirty day presentation where I'm able to show like, hey. This is how I think the business is doing. This is where we have opportunity. What do you guys think? And then try and get a few wins, like real wins, almost going down to the place where I'm doing the hands on work if needed, be it engaging a consultant, be it hiring another leader, be it optimizing some stuff. So get some wins because people want to see that you are a doer. And if you can do that, if I was able to do that in the first three months, then that got me the credibility and trust I needed from everyone else.
00:20:26 · Gaurav Agarwal, Cameron Herold
And then that that allowed me to then fall into a rhythm where I was taken seriously, whatever I said had value, and I needed to continuously deliver. But the... I had earned the trust I needed to then sleep well at night knowing that, the organization values me. [00:20:41] S2: That makes sense. Does that allow you at that point after kind of the first maybe ninety days to start making some of the people decisions? [00:20:49] S0: Yeah. I mean, I think I made some people decisions even well in my day day 30. I think... So it's important to make changes. I think it's important to objectively call out what is good and what is bad. I've often seen a lot of leaders make this mistake where they take a condescending attitude to what is perhaps bad and be like, oh, why is it like this? Even even a kid can do this right. The first thing that you said was good, but the second thing that you said was extremely bad because you have... You don't understand the struggles that is... You'll have to assume that people are smart by default. Yep. And then you will have to give them the benefit of doubt and then make changes as needed. So do not undermine the struggle that might be needed to make changes. But, of course, I made some changes well into my day... Second week because there were a few people who were not aligned with should we do differently. And then you just treat them with respect, get all their knowledge, and then and then you part ways respectfully.
00:20:49 · Gaurav Agarwal, Cameron Herold
[00:20:49] S0: Yeah. I mean, I think I made some people decisions even well in my day day 30. I think... So it's important to make changes. I think it's important to objectively call out what is good and what is bad. I've often seen a lot of leaders make this mistake where they take a condescending attitude to what is perhaps bad and be like, oh, why is it like this? Even even a kid can do this right. The first thing that you said was good, but the second thing that you said was extremely bad because you have... You don't understand the struggles that is... You'll have to assume that people are smart by default. Yep. And then you will have to give them the benefit of doubt and then make changes as needed. So do not undermine the struggle that might be needed to make changes. But, of course, I made some changes well into my day... Second week because there were a few people who were not aligned with should we do differently. And then you just treat them with respect, get all their knowledge, and then and then you part ways respectfully. [00:21:43] S2: I'm I'm curious around the timeline and how long it took you to feel comfortable. I'm not sure if that's the right word, but at what point after starting did you feel like, okay. I got this. I know my way around. I know the people. I know the brand. I know the culture. Like, when when could you kinda breathe and settle in and go, okay. We got this?