Second in Command: The Chief Behind the Chief with Cameron Herold
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?
00:27:05 · Cameron Herold, Gaurav Agarwal
[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? [00:27:12] S0: And I I I try to tell this to my leaders all the time. Right? Like, my budget is only going to go up every year because the business is increasing. I need to spend more money to keep the business growing. So if you think that I enjoy not giving you resources, that's wrong. My job is to allocate more and more resources to my leaders who are effective. I don't win. I don't want this money in the bank. Like, I have this money to multiply it. So show me that you can be an effective leader and I can give you as many resources as you want. [00:27:40] S2: I I love that as a lesson and kind of like a a mindset that you're teaching your team, your leadership team. What other lessons... I mean, you guys clearly at at a thousand people, I'm sure you have a learning and development department, and you've got personal development plans for people. And... You know? But what are... If there were... If you were to say there were, like, two or three kind of core overarching skills that you want leaders to get good at, what would those be?
00:28:02 · Gaurav Agarwal
[00:28:02] S0: I'll give you a very tangible answer, and then I'll give you a maybe philosophical answer. The one thing that I'm trying to train all my leaders on and by leader, I don't just mean my staff, but across the spectrum is systems thinking. And what I mean by that is if I plucked you out of this and I made you the CEO of a company, can you run that business? So I'm trying to coach a lot that the next generation of CEOs and GMs, not the next generation of CMOs or chief sales officers. And most likely they'll still go be CMOs and chief sales officers, but they'll have a holistic view of the business that will make them really, really strong in delivering growth for the business. So we are extremely big on how do we build these cohorts of our future leaders who think like GMs and operate like GMs. And they they just don't... They're not just good at their functional level, but they're also great at being that holistic business thinker. That's big on my mind. But then the second thing, I also coach a lot of my leaders on is how do you be intellectually honest about a problem and use data to to be objective. And that's something that's also important to us. We actually call it the program that we have called, we have designed, we call it bulletproof. Like, how do we make you bulletproof? And one aspect of being bulletproof is knowing the system that you're operating within, but then also can you diagnose problems and communicate those challenges or those opportunities in a bulletproof manner. That means you've thought through all the nooks and corners. You understand what resources are needed. So really trying to make holistic business professionals out of very functional leaders.