Second in Command: The Chief Behind the Chief with Cameron Herold
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.
00:24:58 · Cameron Herold, Gaurav Agarwal
[00:24:58] S2: I wanna talk a little bit about the constraints of resourcing then. You've raised money as a company? You're not public yet. [00:25:04] S0: We're not public yet. [00:25:05] S2: How much has the company raised approximately? [00:25:08] S0: A good check, but the last one that we did was 400,000,000. [00:25:11] S2: Yeah. So so when you're raising 400,000,000, you're not entirely cash restrained. So you can make decisions and work on stuff and and have people working on on things. If you were building a business off of cash flow, if you were... If you had to... Let's say ClickUp was... We had no money in the bank. We can't raise any money for the next two years. What do you think you would do differently as an organization? What would you do if you were... You know, if if cash was not sitting there to be able to be burned? [00:25:40] S0: When I joined the company, we were operating like we have cash to burn. But in the last two years, I have tilted the, I have been heavily involved. Of course, our CEO has been involved as well. But we have tilted the DNA of the company to operate like we don't have any money. [00:25:55] S2: Okay. Even though you do?
00:25:55 · Cameron Herold, Gaurav Agarwal
[00:25:55] S2: Okay. Even though you do? [00:25:56] S0: Even though we do. So so the message I tell my team members is plan and have the vision as if you have unlimited resources, but execute as if you have no resources. And if you can show me that you can work that, then I'll... So what that means is I'm extremely reactive in terms of how we release resources. So you have a new idea? Why don't you stretch maybe 10% and show me that there is a green shoot here? And if you can show me that, I'll give you the resource. [00:26:22] S2: I'll get... Makes sense. I like that. So I was at the head office of Seattle twenty years ago. My mentor was being groomed as the COO at Starbucks. And, I was in his offices. I was walking around, and I turned a corner, and there was a massive saying on one of the walls, like, one foot high letters, and it said, grow big, act small. And I think it... They kept that entrepreneurial DNA of, like, let's not waste our cash. I love that idea, though, of, like, okay. Take the idea, run with it, prove it to a point. If you can prove it to a point, then I'll give you funding to go the rest of the way. [00:26:52] S0: And resources flow, really, like, wherever work gets done. Yep. And the interesting thing is people who want more resources don't get more work done. The people who can get more work done with the little they have end up getting more resources. [00:27:05] S2: It's kinda where your focus goes, energy flows, and where work gets done, we'll pay... We'll give you some more money to get more done. I like it. It's so simple. Right?