Building a $400 Million Startup | Gaurav Agarwal, COO ClickUp (Podcast 410)

In ClickUp, we see the same thing. Our biggest value comes down to that entrepreneurial spirit, right? So we care a lot about growth mindset. We care a lot about being the underdog. We care about working really hard. Those are the ideal employees that work for us. Our best employees are actually not the people who come with big pedigree. Hiding for drive and ambition and betting on that underdog is what has carried us through.

Our guest today is Gaurav Agaral. Gaurav is the COO for ClickUp, an incredible software company that our team loves and companies that we have as members of the CEO alliance are raving about. ClickUp's chief operating officer is leading a productivity platform designed to enhance team collaboration and efficiency. In his role, Gaurav focuses on driving teams, responsibility for marketing growth, sales data and unifying the customer experience under one motion. Prior to ClickUp, Gaurav was the SVP of Growth at Freedom Financial Network. Before that he was the CMO at Molecule. He also has a rich background in growth and business across a range of industries from investment banking, e commerce, Hardware, FinTech and SaaS. In both startup and scale ups. He's a systems thinker at heart. He's also a passionate people leader. He's also very focused on blending the best of B2B and B2C worlds and rewriting the SaaS growth playbook for the future. He also talks to us about his growth trajectory. Leaving India, moving to Singapore, over to Japan, getting back into the United States, back to India and back to the USA Again. Fascinating episode. Fantastic leader. You're going to love this. We'll see you on the inside. This is an episode you may also want to check out on our Second in Command podcast YouTube channel.

So Gaurav, welcome to the Second in Command podcast.

Thanks Cameron. Thanks for having me.

Yeah, very much. Looking forward to this. I have been a fan of your business, of ClickUp. You and I are both or I used to live in the city that you're living in right now, which is a big tech hub in the United States, Seattle. I want to chat a little bit about that. Also love to know how a kid from India came to get over to the United States and, and is now the second command for one of the great brands in the, in the tech space in the United States. And I also want to know a little bit about, you know, what it's like being a COO of a, of a tech company. So why don't you start us off with. Let's start with ClickUp and then we'll kind of go back into some of your backstory. So tell us for anybody who doesn't know what ClickUp is, what the business is, why it exists, and then we'll kind of dive in from there.

Even if you may not recall, click. ClickUp. There was a time where we bought billboards all across the country, and our pitch was all your work in one place or one app to rule them all. So from the genesis, we have been focused on businesses and teams don't need to be working across a dozen tools, but we should be consolidating work more and more. So ClickUp is your everything app for all your work. We bring together docs, tasks, projects, clips, all the different tools that you use, whiteboards. You bring all of these tools together in one place. So instead of you having to toggle multiple different tools, all your work stays in one place. And the gains of that is more productivity and more efficiency because you don't lose time. You don't lose time in switching context. And we have a lot of good stuff coming around, but we are building to that vision where we want to build the modern work stack, which is really one tool or one app. Rule them all.

So one of the things that I, that I love about this tool is that it is kind of everything that you need in one space. It's also very clean, very easy to understand, very intuitive, but at the same time, it's complicated if you've never used a tool like this or you're switching from another how. And, and a friend of mine said one time that a. A shovel does not dig a hole, right? If you give somebody a shovel, it can just stand there unless you know how to use that tool. Right? Like this iPhone would make a great hammer if I wanted to smash stuff in. But how do, how do you teach companies how to adopt a tool like this when they're not using anything in this space?

ClickUp score. You may question, like, there are other products like ClickUp. How is ClickUp unique and differentiated? Not only do we have the best platform vision, but we are also the most flexible platform. So that means now this shovel can be shovels in different sizes and different tools. That further adds that layer of complexity that not only do I not know how to use the shovel, but what you're giving me is this Lego block type shovel that I can use and assimilate whatever I want to. So that further compounds the complexity that you're talking about. Ultimately, it comes down to, because the platform is so flexible, I would say there are two groups of users who want to use ClickUp, there are the power users and these are the operation nerds. They care a lot about process and they care about how does one thing here impacts the other thing somewhere else. And for them, they love the tool because for them they can build whatever they want to build out of it. And that's what they appreciate. We have a lot of resources, we have ClickUp University. We give them all the information that they need, but then we get out of their way and they set up things the way they want to set up. But then for the other people who would rather who need a hole more than they want to dig a hole themselves, because the platform is so powerful, we package solutions on top of it. So for example, this is. We found it so amusing. The number one CRM for small businesses on G2 is not HubSpot, it's ClickUp. And we didn't even know like, why are people doing it. And it turns out that they are using our CRM template. So what we do is on one side, we want to preserve the flexibility of the platform and give it to the power users. On the other side, we are constantly packaging more and more solutions on top of the platform so that any business can go and start using it. And then we have a. I take a lot of pride in our support team that we have built and in our services team. So all the way from free help to paid help. And then there's a rich community of consultants. These are small business owners that make their living off of consulting for ClickUp or providing ClickUp services. So there's a whole ecosystem that people can also engage to build more stuff on ClickUp.

Are the consultants the ones who are kind of leading into companies that maybe don't even know ClickUp exists? They don't know it's a tool that they could be using for the whole that they know they want. Are the consultants saying, hey, here's what you. Is that kind of your sales team?

In a way, not as much as I would like. So a lot of what our sales team does is because we have a product that people sign up. We have thousands of people signing up every day. They would play with it and at some point they'll raise their hand and they'll say, I need help, I want to explore a bigger use case. That's when our sales team gets involved. But because there's almost a parallel ecosystem running that our consultants are vetted, consultants have created for themselves where you will come across a lot of these promotion materials that they have on Their marketing, which is. So I came across this two weeks ago that I'm a realist. I work and build software for real estate brokers. You double click on it. And what she's doing, what that broker, what the consultant is doing is she set up her own business using ClickUp as the backend. But what she's doing is she's building workflow software for real estate brokers.

Interesting. Is that similar to what Go High Level is doing right now, where they're almost creating these like apps that you can almost white label and use. Is that a similar model?

No, I would say this is closer to what say an airtable would look like if it was for SMB where it's still very much a ClickUp tool. So we're not allowed, we're not white labeling it. But the consultant is the person who captures majority of the value that is built because ultimately the client, the customer still pays only the license cost to ClickUp. But a lot of the dollars is generated in the service fees which is then captured by the consultant. Have you.

I don't know whether High Level is any kind of a competitor in any way to ClickUp in terms of like one or two of the little potential parts of the of the software. But what do you like and not like about that? Go high level, almost multi level marketing on top of a multi level marketing model. Do you know much about that or can you speak to that?

I actually haven't looked at gohighlevel, so unfortunately I can't speak to their use case. But the way I look at this is I see ClickUp in two ways. One, we will have opinion. So we want to consolidate the modern day work software stack, right? So if you want to use docs or tasks etc. You should just use ClickUp. But then because the platform is built in a highly structured and configurable manner, ClickUp is also a low code, no code workflow building tool. And on that part I would love for every vendor, for every consultant to build some sort of workflow software and then eat up a whole industry. Like if you look at modern day SaaS, a lot of that is just data transformation and workflows on top of it. And ClickUp can do that.

That sounds like what Go High Level is doing with this kind of white labeling where these consultants are white labeling something and they're selling that solution into an entire marketplace. Which is kind of what you're talking about. How so you said ops nerds. It's interesting that you said that is operations the kind of doorway or the entry point into all the organizations for you, then yes.

And when I say that, I'm just not talking about. So I come from the world of hardware. I did a small stint in hardware and operations in hardware is different than operations in go to market is different than operations in sales is different than operations in design, in product. But in almost every function and every department these days, you always have a small ops group that's all about how do I make this whole department run efficiently and how do I ensure that we cut redundant work, we cut the work about work and we ensure that our resources are deployed effectively. Those are our primary stakeholders. Now those stakeholders use ClickUp for all sorts of use cases, from creative and design to event planning to product development to engineering. We are even using shop floors for what it's worth. Like some of our big customers are actually automobile makers and they're big names, they're used by pharma companies. But each one of them is using ClickUp to operationalize some sort of program or some sort of project that then touches a lot of other departments.

Interesting. Okay, I want to go into a little bit more about Clip ClickUp in a second, but I want to go backwards and let's kind of figure out how you got there. I mean, you're the CEO of a great software brand. How many approximately employees do you have?

Currently we have about a thousand, give or take.

Yeah. So you're running a real company, real moving parts. You're a true CEO. How did a kid from India end up in Seattle? I mean, I knew how I have a kid from Canada ended up in Seattle. How did a kid from India end up in Seattle? As the CEO of a thousand person company, what's your career journey?

I think in some ways I think I got lucky and I was very privileged so to give you a walkthrough. I graduated in engineering, did quite well in studies. I ended up. My first job out of college was actually in Singapore and I worked for Barclays Capital. And I'm so grateful for that experience because I was in a high pressure. I was on the trading floor working on structured products, trading bonds. So I learned a lot and I did that across Singapore, London and Tokyo. But then there was a time after three, four years and I'm like, this is not what I want to do. I want to actually build some stuff. And for a lot of people who grow up in India, this is so much competition out there. People are so smart. You want to get out and you want to chase that better Life outside India and you want to, you want to go to the us you want to go to the uk. So I was in Tokyo at that time and in some ways I was pretty happy. But then I was like, you know what, I want to, I want to actually build. So I left my job and I moved back to India and I said I want to build something because in my heart I'm an entrepreneur, I'm a builder. And then I moved there for a company called Lens Bricks that came out of MIT Media Lab and they had an office in Boston and in India and we were trying to do some smart, deep learning stuff on, on cameras, on video. And this was like 15 years ago. That has not been done before. So eventually the company ran out of money. But through that company I ended up visiting the US quite a bit. So it's interesting, I pack my bags, I go to India in two days. I don't even get to get my house there. I was shipped to the US to go work on some. I was doing product development and customer development for them. So I came to the US for that. And then we got into a hardware accelerator. It was a hardware product, it was a smart camera product. And through that accelerator I made friends. So when Lens Bricks went under, I had a chance to go work for this company called Molecule which was commercializing a new air purification technology. And I joined them on the business side, ran growth and e commerce for them and that's how I moved to the US So I moved from banking to product management for a computer vision startup to then leading growth in a hardware e commerce company, growing that business to nine figures in revenue and then jumped into fintech. And then from fintech I got into SaaS. ClickUp has a big self serve business. So they hired me to come run as the chief growth officer to come run the self serve business. But over time I got promoted end of last year to run all of operations. So here I am, you know. So the interesting thing is I actually made out, left the country and then I decided to go back and I, in my mind I had convinced myself that maybe I'll never get to go out again now because it's very hard to get out.

Yeah, India is a great place. I've been to India five times and every time I go to India I'm glad I'm going and every time I'm there I want to get the hell out. And then when I'm out I want to go back. It's like, it's like, it's like an Addiction that you know you shouldn't have, but you can't get away from it too. You said something that I was really interested by because when you started talking about being in banking over in Singapore, I started laughing to myself going, you don't have a banking personality and DNA. You have a bit more of that gregarious kind of entrepreneurial DNA, which is very unusual for COOs, by the way. And then you said you're more of an entrepreneurial leader, I think you said, or more of an entrepreneurial bent to you. I'm intrigued by that because we've had about 400 guests on the Second In Command podcast of some incredible brands similar to yours. Very few of them are entrepreneurial. Do you think that entrepreneurial is something that is critical in a high growth company or in a software kind of company that's in growth mode?

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've, they, 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 continue to manage your edge is by being entrepreneurial.

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 is fairly entrepreneurial in many ways, and it's fast paced and it's definitely 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?

Actually, no, in the sense that I went to school for something called industrial engineering and it's called management science and engineering. In the US in some programs it's also called operations engineering. Okay. 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. 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 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 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 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?

About 800.

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?

I came in as a Chief Growth Officer, primarily responsible for the self serve.

Business and Chief Growth officer, is that like marketing sales or what was that?

Okay, I had under my remit marketing data and some elements of product that directly touch our growth numbers.

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 at 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 know 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 90 days?

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 a lot of. 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 90 days, the way I looked at it as 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 90 days I was able to shift a lot of our marketing programs and unlock ROI immediately. And I do this. This is a hack that I followed in the first 30 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, I 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 30 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 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 90 days came in with a growth, mindset, mindset to absorb, be a sponge, learn all the context. I can do that 30 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. 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 that I had earned the trust I needed to then sleep well at night knowing that the organization values me.

That makes sense. Does that allow you at that point, after kind of the first maybe 90 days to start making some of the people decisions?

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 have 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 have to assume that people are smart by default, 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 what should we do differently? And then you just treat them with respect, get all their knowledge, and then. And then you part ways respectfully.

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 kind of breathe and settle in and go, okay, we got this?

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. And I think it's important to get to that place where you feel you have built that trusted relationship.

Yeah.

Since then, Cameron, I feel like I've always felt like I need to do more. 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.

Okay, speak to that for a second. In terms of the desire or the feeling like, we can always do more. How do you know when to say no or not now or to not get involved? Because you could be involved in every meeting, 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?

That's perhaps the downside of being an entrepreneurial CEO. That's been the challenge that I'm having to figure out, because on one end, it's really important to continuously push the boundary and do more. On the other hand, you 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. I'm 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 burn something down. So we are making space for ideas while keeping the constraints of resourcing in check.

I want to talk a little bit about the constraints of resourcing then. You've raised money as a company. You're not public yet.

We're not public yet.

How much is the company raised approximately to go check.

But the last one that we did was 400 million.

Yeah, so. So when you're raising 400 million, 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 cash was not sitting there to be able to be burned?

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, Zeb, 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.

Okay. Even though you do.

Even though we do. 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 call. 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 I'll get.

Makes sense. I like that. So I was at the head office of Seattle 20 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. 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 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.

And resources flow really, like, wherever work gets done.

Yeah.

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.

It's kind of 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.

And 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.

I love that as a lesson and kind of like a mindset that you're teaching your team, your leadership team. What Other lessons. I mean, you guys, clearly 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?

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 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've 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.

I like that you talked about the systems thinking. My mentor again, who is being groomed as the CEO 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 and 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 what you mean by systems thinking or give me an example of a systems thinking kind of.

Can you give us a specific, for example, 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, your case, that's a great outcome. The second one could be a big one 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 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 should have thought about all of that stuff sooner than later. And that's what good systems design, system designers do. 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're 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 gap at 20%.

Got it.

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's your vision and your intellectual honesty to be able to stitch that 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?

ClickUp is based in San Diego.

Based in San Diego. And you've got the second in command based in West Seattle. Do you have offices in Seattle?

We do not have offices in Seattle, but I travel to San Diego almost every other week.

Okay, how does the company operate with a. How many of your employees would be in San Diego and how many would be remote?

About 30% in San Diego and the rest would be remote.

Okay. Is that partially why, then a second command to 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?

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 so 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 call the water cooler stuff. Right. And the way I phrase it as hybrid work or remote work kills serendipity. 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 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 bond.

Yeah, it's kind of the. The whole saying that happened during COVID which is the off site, is the new on site. Right.

The offset is the new onset. Exactly.

All right, 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?

So you might have seen the recent post by Paul Graham around the founder mode that went viral. That was about Brian Chesky. Brancheski has been. Our culture is very similar at ClickUp, where leaders are in huge details. I've heard Steve Jobs, Steve Jobs, Brancheski. They come from that school of leadership where you don't just hire smart people, but you go into the details with them, you align thinking. So the word product is really good. ClickUp works in the same way. What that often means is we are all in details a lot. And one thing that I'm trying to work on myself is two things, actually, that I'm thinking, how do I be less reactive to things? Because just because I'm in details on everything doesn't mean I need to react on everything. So that's one thing that I'm constantly trying to improve. And the second thing that I'm trying to improve is more empathy. So everyone at ClickUp is at a different place. We don't get to work together as much in the same office. That's what I meant by humanizing work, because I see you just as an interviewer and I don't know much about you. There's very little humanization that's going on here. So I'm trying to build a ton of empathy because again, I'm. That I'm. I'm very data driven, very numbers driven. When you work on the Wall street, then, then empathy takes the backseat because there's no empathy. There's no empathy. Like you have to be a shark if you work in the world. Unfortunately. Yeah, I'm very much like that. Good in a way because it allows my teams to be successful and ultimately, when they are successful, everyone is happy. But I'm trying to also work on how do I humanize myself and humanize the work that I do with my people. So. So it's not just about the numbers and winning anymore. It's also about working together.

Do you remember, Oh, I want to say this was 2011 or 2012, and it was when the Taj and the Oberoi hotels had all the shooting and bombs going off over in India, in Mumbai. They interviewed the CEO of the Taj Hotel Group afterwards and they said, you know, your, your employees, the staff didn't leave the hotel. When everybody was running and there were guns and bombs going off, your staff stayed in the hotel to take care of the guests. How did you get them to stay? And they said, we didn't get them to stay. It was like our. It was our, our, not our obligation. It was like our opportunity. It was our. We wanted to show our core values. We wanted to care about people. And we're like, well, how did you train them to have that kind of core values? He said, oh, we don train Them. We hire people who have those core values. And they said, well where did you find them? And he said we don't find them in the big city. He said we only hire people from the smaller towns and the villages because they haven't lost their core values, they haven't lost their humanity, they haven't lost that kind of that human connection. I thought it was a really beautiful lesson from the CEO of the Taj Group.

Yeah, I mean I think it ties down to privilege in some sense. So when you ask me about my career journey, right. I feel incredibly grateful to be where I am. And I know that because I know that there are for every Gaurav, there's perhaps 100 more people in India who are as smart as me who could have been here when I've been given this opportunity. I take it very religiously that I need to do my best job and because I know that there are other people more deserving than me who don't have this opportunity. Maybe that's not true, but I think that is majorly true and I think it allows me to respect the opportunity I have. Really, really well. And in ClickUp we see the same thing. Our biggest value is, comes down to that entrepreneurial spirit. Right? So we care a lot about growth mindset, we care a lot about being the underdog. We care about working really hard. Those are the ideal employees that work for us. Our best employees are actually not the people who come with big pedigree. We have so many people who have joined ClickUp as a support rep. But in three, four years one of one of my best mid market sellers was actually a support rep. One of our best program managers who can who technical program managers was a support rep. We find over and over that hiding for drive and ambition and betting on that underdog is what has carried us through. And that is, that is one of the biggest things. I see a parallel here that for us it's not so much about the small tier cities but it's about finding people who really want to make a point and work really hard and are not afraid of ambition and then giving them a chance. And in some way I ended up here because Zeb gave me a chance.

Well, I want to ask you a question about you as a 21 year old getting ready to go off to Singapore. My 21 year old son is going off to Singapore in January to do an exchange at management University in Singapore. Probably a very similar age to when you went off to Singapore. What advice would you give the younger you? The younger Gaurav who's off to Singapore, you know, 21, 22 years old. What advice would you give yourself back then that you know to be true today, but you wish you'd known when you were younger?

I'll take bigger risks. This is interesting. At that point I was actually working on a startup idea that I had very good traction. But then because I had this amazing opportunity to go to Singapore and being paid fair amount of money, I said let me go do that. But in hindsight, I wish I had surrounded myself with mentors and other people who would tell me that. And I also come from a very middle class background. Right. So that allure for fixed money was way better than that startup risk. But I wish someone would have told me that what you have at hand is really good. And here, take a small check. So I, I grew up in an ecosystem where the startup community wasn't as robust as it is right now. So I wish if I could do that again, I would certainly take on that bet and take on that risk because the amount of learning I would have had is so huge. So I was, I was in Singapore, then I moved to Tokyo and I'll see a lot of similar startups come out and raise money and do really well. And I was like, I should have just done that. So I was bitter for a couple of years. In hindsight, if I would not have gone to Singapore, I would not have been here. Because everything that I used to run my business, I learned portfolio theory, data driven, decision making. How do you react quickly to things? There's a lot of things that I do right now, leverage that I, I didn't just learn them, I experienced them in my job. So I think two things. Take more risks. But you know what, if you don't, like, let the dots connect. Dots will always connect. You need to. But at each point, try your best. Like for each opportunity that has been given to you, this may not be the opportunity you wanted. My first mentor in Singapore, he said, and he was a banker of course, like he was an md, trading the entire emerging markets desk. And he said, my first job was a toilet cleaner as a kid, but I was the best toilet cleaner there was. Take more risks. But then if you're stuck in a situation, if you're not happy, change it. But make the most out of the situation you've been given because that's how you create future opportunity.

Yeah, that's advice that I'm giving both of my kids right now is whatever you're in, try your best at that. And then when you're ready, go to the next thing and try your best at that. Gaurav Agaral, COO of ClickUp thank you so much for sharing with us today on the Second Command podcast.

There's never usually a right answer to get to the solution of a problem. There's many ways to get to that solution, and you're always trying to figure out what's the most optimal, what's the cost effective, what's going to be the best speed and but if you're all thinking the same way, you're all going to come up with the same idea. And where diversity really comes into play is.