Second in Command: The Chief Behind the Chief with Cameron Herold
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?
00:21:43 · Cameron Herold, Gaurav Agarwal
[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? [00:22:03] S0: So I think that happened first... Within the first three months. Like, there was a big moment where our cost of acquisition was right... Were rising, and I was able to plug that in. That was the point where I felt like, okay. I don't think I'll get fired for doing a brand. And I think it's important to get to that place where you feel you have built that trusted relationship. [00:22:22] S2: Yep. [00:22:23] S0: Since then, Cameron, I feel like I've I've always felt like I need to do more. Mhmm. That's because my scope has always expanded. So I've always taken on new things, and it's like, am I doing a good job? Am I doing a bad job? Let me keep pushing and let me show results. And then as soon as that happens, I'll take something else. [00:22:40] S2: Okay. Speak to that for a second. In in terms of the desire or the feeling like we can always do more, how do you know when to say no or or not now or to not get involved? Like, how... Because you could be involved in every meeting and every decision and all of the things, like, analyzing the everything. How do you how do you know where to focus and where to delegate and where to, just not get involved?
00:23:04 · Gaurav Agarwal
[00:23:04] S0: That's perhaps the downside of being an entrepreneurial COO. That's been the challenge that I am having to figure out because on one hand, it's really important to continuously push the boundary and do more. On the other hand, we also have to be realistic about how do we balance things and how do we land the few things that are extremely important. I don't think we have nailed it. To be honest, that's something that I'm trying to figure out how to nail it. But what we have done is we have moved away from very waterfall style OKR based approach where every six months or every three months we will create OKRs. We don't do that anymore. We have moved to a more Kanban style approach where we know what the big priorities of the business are. That's not changing. So directionally, we know these are the things we need to nail. What we can't commit to immediately is what's the path in which we get there. Maybe we take 10 steps forward, then we take a 90 degree turn, then we do 10 steps, then we do five steps. So we don't know the path to getting there, and that has to be highly iterative. So the way we run the business is, Gaurav, you have a new idea? Great. I've added that in my backlog. This is my backlog, and we do this pretty dynamically. We're like, I am working on these three things right now as the highest priority thing. It feels like there's a better idea that we should work on. Do you want me to bump something down, or should I just keep working on my three things and make this the fourth thing after that? So we have built this muscle now where these kind of conversations just happen dynamically without us having to engage in a week long planning exercise every quarter. So we operate in a very fluid Kanban board style approach where these are my top priorities, and then that's the same for me. My top priorities keep shifting week on week and so on. And it really comes down to, you have a new idea, I'll factor that in, and I'll point something down. So we are making space for ideas while keeping the constraints of resourcing in check.