Second in Command: The Chief Behind the Chief with Cameron Herold
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.
00:29:36 · Cameron Herold
[00:29:36] S2: I like that you talked about the systems thinking. My my mentor again who is being groomed as the COO at Starbucks told me a story one time, and he said he was, talking to his CEO who was Howard Behar at the time at Starbucks. And Howard called Greg and said, why is the letter b on the sign at 45th In Wallingford in Seattle not working? And Greg said, I don't care. And Howard goes, what do you mean you don't care? Greg said, that's not a systems question. He said, the question we have to ask is what system is missing or what system can we put in place to ensure that every letter on every sign at all of our locations is always working? Like, that's so great. Right? Is that is that what you mean by systems thinking? Or give me an example of a systems thinking kind of... Can you give us a specific?
00:30:19 · Gaurav Agarwal
[00:30:19] S0: For example, a systems... When I say systems, I don't just mean the technical system, but exactly what you said. What's the combination of process, people, and technology that allows us to get to a certain outcome? And we understand the whole combination and interplay of these things really well so that we can design a system. In your your case, that's a great outcome. The second one could be, a big one in in revenue teams is comp design. Comp design for a seller. To me, that's a systems thinking exercise where what you're trying to do is you're trying to figure out if I pay them more on this. So I'll give you an example. We started introducing services for our big customers because they needed help. We started comping the same dollar commission rate on services as much as we do on seats. What happened because of that was sellers started selling more services. But now services don't have the same retention as the seat because once the account has been sustained and has been set up properly, services will churn. But... So then by design, you you should have thought about all of that stuff sooner than later. And that's what good systems design... System designers do. Like, if I impact, if I... If I'm going to pay the same commission rate on services as much as seats, this is the downstream implication that I'll see on that. So when I took over the sales team, we added a cap. And we said, let's... Sellers want to sell services. Typically, they are selling 15% of their quota and services. But then some people are misusing it and abusing it where they are selling 50% of their quota and services. And we added a cap at 20%.
00:31:47 · Cameron Herold, Gaurav Agarwal
[00:31:47] S2: Got it. [00:31:48] S0: That's a good example of systems thinking where a butterfly flaps its wings in one place and something else happens perhaps way down. But these things are connected, and it... It's your vision and your intellectual honesty to be able to stitch that. [00:32:02] S2: Right. And if you think about that in advance and we prevent all the problems downstream, You're based in Seattle. Is ClickUp based in Seattle? [00:32:09] S0: ClickUp is based in San Diego. [00:32:11] S2: Based in San Diego, and you've got the Second in Command based in West Seattle. Do you have offices in Seattle? [00:32:17] S0: We do not have offices in Seattle, but I travel to San Diego almost every other [00:32:21] S2: Okay. How does the company operate with a... How many of your employees would be in San Diego, and how many would be remote? [00:32:28] S0: About 30% in San Diego, and the rest would be remote. [00:32:31] S2: Okay. Is that partially why then a second in command, the COO, can be remote as well? And how do you work around things like culture, you know, the water cooler conversations when you're not there?
00:32:31 · Cameron Herold, Gaurav Agarwal
[00:32:31] S2: Okay. Is that partially why then a second in command, the COO, can be remote as well? And how do you work around things like culture, you know, the water cooler conversations when you're not there? [00:32:44] S0: Because we are remote or at this point, we're hybrid. Even people in San Diego only go to the office once every week. I could be, remote and it works. The second we use ClickUp for everything, and I think that does allow us to stay on top of things, we don't have to be in person for everything. We we are a low meeting culture. We work really well asynchronously. ClickUp facilitates all of that. The part that ClickUp does not facilitate is what you called the the water cooler stuff. Right? And and the way I phrase it as hybrid work or remote work kills serendipity. [00:33:14] S2: Mhmm.
00:33:14 · Cameron Herold, Gaurav Agarwal
[00:33:14] S2: Mhmm. [00:33:15] S0: When you jump... When you run into someone doing something and you have an idea, you share it you share it, and they will add to it. So there's a lot of serendipitous outcomes that get generated when you are in person. We are big on trying to create a lot more opportunities for people to get together. So we haven't... I've been testing this with my teams, but we'll have cross functional teams get together, once a quarter. Some some teams get together once a month. And the whole idea is to have fun and also humanize work, but then also do some work. But the goal is to understand each other as people and not just as stakeholders who who cooperate or who work on Zoom. So we're trying to figure out alternate modalities where teams still get together in hackathons and conferences and leadership summits and build that ball. [00:34:00] S2: Yeah. It's kind of the the the whole saying that happened during COVID, which is the off-site is the new on-site. Right? [00:34:05] S0: The off-site is the new on-site. Exactly. Alright. [00:34:07] S2: Let's talk about your growth. I mean, you've... Have clearly grown in your career. What are you growing on, or what are you focusing on growing today as a leader?