Show 135 – Unicorn Interviews – Zeb Evans – ClickUp

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Tyto has launched an e-book off the back of this series, it builds on the inspiration behind the series and hopes to inspire leaders of the future. It’s a consolidation of the highlights from the first 15 Unicorn leaders. Growing Without Borders, the unicorn’s CEO guide to communication culture is available on Tyto’s website.

The 18th in our series of episodes that we’re recording in partnership with the European PR Agency Tyto, around and their Own Without Borders podcast.

Russell Goldsmith and Tyto’s founder, Brendon Craigie were joined online from San Diego by Zeb Evans, Founder and CEO of the customizable workplace productivity platform ClickUp. Founded in 2017, ClickUp raised $100m in a Series B funding round in December 2020, reaching a $1bn valuation.

Zeb said he has been an entrepreneur since he was born, he has always been creating businesses. In college, he actually built a social media automations platform before that ‘stuff’ existed where you could automate your tweets ahead of time and automate actions that you were performing manually, and he actually added reporting before the API existed to do that.

They started ClickUp with base camp when it was just Zeb himself, and then at the end of that company’s lifecycle, they were at about 70 people and they still had base camp, but they also had JIRA for engineering, Asana for a lists, Trello for boards, approvals software, Evernote, Google Sheets, Google Docs, Todo lists for personal reminders, Slack and Skype. He said it was a mess of productivity applications – they’re named productivity applications so they should be saving you time or making you more productive. Zeb couldn’t help but feel he was always less productive by using so many different applications. So, long story short, they created ClickUp as an internal tool to solve those problems and through that journey of just four or five weeks, they realized that there was much more to do in this industry and that their mission for saving themselves time and making themselves more productive is much better served as a world mission of making everybody more productive and saving people time. So, ClickUp is a platform where you can replace all of your workplace productivity software with one, where you can work with your teams on projects, tasks, docs, goals and keep everybody aligned and on the same page.

Zeb explained that early on, they always wanted to be unopinionated in the way that they build software. Generally speaking, a few years ago, the consensus, at least in Silicon Valley, was do one thing and do it well, focus on a vertical, focus on a market, a niche. Zeb said they never wanted to do that because their premise, their whole mission was replacing all of those several pieces of software and their thesis was that you have to use so many different pieces of software because they’re inflexible, because they’re so opinionated in the way that you work and because they’ve taken that philosophy of just do one thing and do it well. He said that was the biggest decision that they made early on, and they relentlessly stayed with it, is to build very flexible software that works from teams of two to 2000 and to be able to break down those barriers of different departments. Usually, you have different software for engineering versus marketing versus creative versus operations versus HR. Their main focus was building unopinionated software that worked for everybody. Zeb explained that the general philosophy behind their promise that ClickUp will save a day every week, is that replacing several applications naturally is much more efficient than contact switching. You don’t know where to find things. You don’t know what people are working on. You don’t know where to put things and you certainly don’t know priority of tasks. And so, ClickUp found when you have one platform, one single source of truth for all of your work rather than several of them, there’s this natural time efficiency that is safe. This number is based on surveys that they send to customers before and after using ClickUp. Zeb added that they’re doing a really cool, more in-depth survey now with an outside firm for real quantitative analysis to really get down into the minutes of time that’s saved. It’s not easy to measure, but it is self-admitted data that they have from their own customers. From another perspective, it certainly is much more efficient, not only when you’re using one platform, but when you have a platform that’s flexible for the way that you work. So instead of you accommodating the platform, meaning you have to change the way that you work, adapt the way the software works, at ClickUp it’s ‘you come to us’, and the software works for the way that you want to work.

The easiest part to get started with ClickUp is replacing your project management tools. What they end up seeing is adoption from the top of the funnel for things like docs, knowledge bases, wiki’s, goals, time tracking, workload management software, resource management software, sometimes those are the entry points into their software, but a lot of time, that’s the ecosystem that you start replacing. So, you start replacing project management software, then you branch into doc, then you branch into goals and then you branch into resource management and people management. Then there’s a plethora of tools they replace as well. Zeb explained that they don’t necessarily want people replacing everything on day one, that can be very challenging and unless you’re a really small company, it’s not practical to experience change management like that. So, they always coach on replace one thing at a time.

From the beginning that whole thesis around building very unopinionated software has done ClickUp well in the industry. Zeb believes that the industry right now, has very opinionated solutions, things like JIRA or Asana. But he said you also have no opinion software, which is essentially no code software, Notion or Air Table, maybe Coda also can be classified there. And so, he believes that you have polar opposites of the spectrum whereas he said ClickUp captures everything in between. He said that their opinion is that you’re using their software for work and so they provide a bunch of really efficient work tools that can save you time and make you more productive and connect your team. Whereas on the no code software, you have to try and build those things. Zeb added that what they have seen is that is inefficient, and customers don’t actually like doing that, it doesn’t scale with a company, and it certainly doesn’t replace the rest of your software. That’s a huge differentiator for ClickUp – they can actually replace your doc software, as well as your very opinionated project management software. ClickUp can also replace your OKR software and your time tracking software in one. They’re also looking at adding some more features in the next few months. When you look at the ecosystem today, ClickUp are the only platform that has all those four pillars of overwork: task, docs, goals, and chat in one place and so Zeb believes that’s the fundamental difference between them and the other players.

Raising Finance

Zeb believes that with raising in general, there are a couple of good things that can come with it, he wouldn’t raise just to do these things. Hiring and that halo effect that happens where you’re able to at least attract more talk to your talent. There is an argument to be made both ways. You can build a very sustainable business without raising. Zeb said that he doesn’t necessarily advocate for it, especially if you’re not in a very competitive industry. If you’re in a very competitive industry, you need to if other competitors are raising around you, he thinks that forced their hand a little bit. One of the biggest things that Zeb discounted before raising is you just have access to better talent, and you do have that attractiveness from candidates, especially the classic Silicon Valley candidates.

Remote Working

Fortunately, ClickUp build software that helps people stay connected remote or in office. They have been pretty well set up with the foundation since day one for working remotely, even prior to Covid, they were about 50 percent remote, today it’s roughly 60 percent remote. ClickUp have always been very flexible with remote work. However, Zeb said that the hardest thing to scale remotely is culture and connection and that’s what they focus on more than work and more than knowing people. If you’re hiring the right people, they’re going to get the work done regardless of if they’re working at home or if they’re working in the office. There are certain roles that they believe, and that they’ve heard from their employees, that are more important to be in office, things like creative roles. It’s really hard being creative on a zoom call, that’s the reality. So, they’ve seen those employees want to get back to the office, whereas engineering, most of them actually prefer working remotely, they prefer being heads down in the zone. And so, they just firmly believe everyone’s different and that’s what they are accommodating for post Covid.

Priorities for the coming months

They were about seventy five percent of the way there on their vision for what ClickUp is and so Zeb thinks the next six months or so will be close to realizing that full vision. There’s a couple of big pieces of the ecosystem that they don’t have today and that they will have over the next few months. One of them is virtual whiteboarding, that’s a big piece of the productivity ecosystem that is very complementary to ClickUp’s software today. They see the vision for the future of all of your work in one place and this one they naturally have to be able to capture that market share, but also more so they think that it saves people time using that instead of having to go back and forth between your whiteboarding software and ClickUp and copying and pasting tasks and keeping everybody in different pages. They can have that same efficiency gain and the same saving people time gain from putting your virtual whiteboarding solution in there. ClickUp has grown very quickly, they grew from roughly 60 to six hundred employees in a year, during that, some things break down and one of those things was hiring engineering. Their engineering team is small and mighty today, much smaller than people would think on the outside. They’re playing a little bit of catchup there and making sure that they stay ahead on the engineering side, hiring a lot more engineers and having that maintainability and focus on reliability and quality in addition to shipping features. At a traditional tech company, you’d really want closer to 50% in R&D, whereas they are at roughly 10%.

Early on, Zeb said, you should try to get by with as little engineers as possible. ClickUp did and they had one person owning the whole backend, infrastructure. The downside to that or the risk of that is that you have one person in the whole backend of the infrastructure. If you lose that person, you could be screwed in any way. So, you’re taking a bet, but maybe if you have two people there, they’re going to have extreme ownership of everything. They’ll be much more committed. But it’s so much more efficient having one person own it all, at least early on. On the frontend side ClickUp only had a couple of engineers there at first. You can move much quicker when you have somebody that knows the entire system from start to finish and they built the entire system. That doesn’t scale indefinitely, obviously, and so at a certain point, you do have to hire more engineers. Zeb would not advocate for going out and starting a software company, raising a bunch of money, and hiring 20 engineers right off the bat. It’s going to be much slower than a four- or five-person team. The difference is, once you start scaling, once you start growing, you do have to build those teams back and put people in the pods and have infrastructure teams and dev ops teams. You have to scale it at some point. But certainly, early on, as few engineers as possible is much better.

Zeb explained that they have always focused on being organic. They were bootstrap much longer than any of their competitors. They bootstrapped to really extreme profitability a year or so ago when they first raised and Zeb advocates for doing that, as long as you can and raise as little funds as possible if you’re not able to bootstrap because you will have an extreme focus on the product, extreme focus on the customer, things that matter other than just trying to build teams as fast as you can. There’s a time and place for that. But that’s after your product market fit. If you can build an organic engine around you, then you don’t necessarily need paid marketing up front. That’s what ClickUp were focused on. Your branding has to appear much larger than you are early on, it’s hard because design is subjective you’ve got to find one of those exceptional designers and they have to be able to make your brand appear much larger than you are. Zeb believes that is a huge key that a lot of people missed and early on, it matters more than anything. If you can do that and you can also acquire customers organically, then you can punch up and you can start getting into an industry that largely is made up of huge competitors.


Zeb said that he worried about ensuring the culture grew the way he wanted it to whilst growing the company so quickly as everybody talks about how culture’s going to break down, you can’t scale forever. Today they been able to scale it, Zeb thinks it’s largely because if you make the right hires, then they hire the right people also. So as long as you really understand what your culture is, and you don’t want to just make something up to make it up. ClickUp have always been optimistic people that want to grow, that’s the single sentence that distils them. They look for those two things, optimism, and growth. Those two things are very common factors that all employees at ClickUp have. It makes for a really great environment to work in and one that you can have fun with people, Zeb explained. You can joke with people, you have a bunch of laughs, but they’re also very serious when it comes to their work, probably more serious than other companies. If you can have those two, they really balance each other out and they have been able to scale that so far. Zeb hopes they will be able to scale that indefinitely. Every month Zeb has a core values talk where they talk about their core values. They revaluate them every quarter based on where they are. Those types of things keep culture and core values front of mind for people. ClickUp also have core value awards every month, they recognize the top several people in the company that are exhibiting the core values. They give them more equity in the company, a raise and recognition in front of everybody. So, they celebrate their scaling, their culture.

Internal Communications

Internal comms is challenging, it’s something that ClickUp didn’t necessarily hold high on a pedestal. They actually didn’t really think about internal comms at first, now, they are naturally doing a lot of it, but Zeb didn’t think of it as a function or as a niche that you have to have. And once they started doing that, Zeb thinks employees felt much more connected. What drove them to start doing that is Covid, where they knew that they needed to create that connection with people. They do an all hands every Tuesday with the entire company and every single person is on that call, they try to be flexible time zones, but at least everybody watches it. They also do coffee breaks every day where the whole company, if you want to or if you don’t have a meeting, come in and jump in a zoom break out room and get to talk to people. They do biweekly random meetings with people. So, you’ll be meeting with somebody random in your department just to get to know them, because largely you haven’t gotten one on one face time with a lot of people. On the leadership side they do skip level meetings. Zeb believes that some of the best internal comms that you’re going to get is skip level meetings, it’s not necessarily to look for problems, but you largely get a different story from somebody that’s telling you versus what they’re telling their manager. So, skip level meetings have been huge for ClickUp as well as just understanding how people are feeling.

Being an External Spokesperson

Zeb said that being an external spokesperson is always going to be super important, especially when you’re in an industry like ClickUp’s, where it’s very competitive. You have to have some differentiation and externally, is the easiest way to do that. So, it’s not just himself, but it’s the branding, it’s the content that they create, it’s that organic content, organic following, that community. You need somebody that is the spokesperson for that. Zeb has always had this vision to what they are doing, he is the product person; the CEO during the day, but his nights and weekends are head of product. He is very, very obsessed with their product, their customers and creating the best possible user experience that they can create. That largely benefits them for Zeb to be that natural spokesperson and the representative of the business.

Communications in general has been learned, Zeb said. He said he would be more on the introvert side and more on the shy side as a kid and growing up. He has thrown himself into these positions and you grow from it, you learn from it, and it becomes more comfortable as you do it more naturally. It’s such a simple thing, but that is the truth. It just becomes easier as you’re doing it more. Zeb added that it’s much easier when you are being authentic, when you’re talking about stuff that you truly believe in and not just thinking about talking points or reading things from your PR people. It’s much more powerful and it’s much easier to do when it’s real. He believes communication to be exceptional, especially as that spokesperson. You’ve got to really believe in what you’re doing and largely be able to get that passion across.

There’s always challenges with communicating your vision, especially early on and really, it’s in your head. Your vision doesn’t have to be just the CEO or just the founder that’s doing this, you can have a vision if you’re an architect, if you’re a principal architect, if you’re an engineer, if you’re a marketing person, all of those things go into vision. People always assume that everyone knows what’s inside of their head when they don’t. That’s been a big learning lesson for Zeb, early on and probably still a little bit too much now, he assumes everyone knows his vision, everyone knows exactly what he’s thinking, and everyone is on the same page there. You can never assume that. One of the biggest lessons he learned is just repeat yourself over and over and over again. Even if it’s the same employer that you’re talking to, just reiterating that makes it real. The reality is you can never remember how many times you’ve told somebody something. So, there’s no downside to repeating it. You’re going to be able to get your vision across much more. And that goes for everyone, not just the founders of the company. If you have creative vision, you should continue reiterating that and repeating it as much as possible to drill it in. Zeb firmly believes that everything happens for a reason. When you fail, you learn from it, and you move on. So, whilst he doesn’t necessarily have regrets about the failures, because if he had changed something, he wouldn’t be in the same position today, he thinks there are certainly some lessons that he learned a little bit later. Some things you don’t focus on when you’re building a business are more of the “boring” things like legal or HR, those types of things are very important. So, a big lesson that they learned is that they need those things. And fortunately, they have built those teams now. But they didn’t have them early on. Finding great managers as you’re scaling also, you cannot hire people yourself when you scale. You have to find other people that are great at hiring and that you trust to hire in order to scale. That was a huge lesson for Zeb and a huge mistake early on, he was still trying to hire everybody, and that simply didn’t work.

He added that he has got thousands of those failure and mistakes stories. But it’s something where you have just got to continue.

Richard Branson

Speaking on meeting Richard Branson, Zeb explained that he asked him a couple of questions at first, one of which being how do you hire people, specifically leaders, what do you look for in leaders? They sat and talked for six hours straight. They connected and made a really great relationship. So, he answered the hiring question more culturally; hire the right people for your culture, which is very important because you don’t just hire for the experience you’ve got to hire people that also match your culture, otherwise it’s going to be a misfit in the company. The other question Zeb asked was how do you know when it’s right to focus your time on other things and how can you focus your time? Branson explained that you have to figure out how not to work. Zeb said that was really good advice for him, because he thinks especially as a founder and as an entrepreneur, you always try to do everything. And even as you scale there’s lots of things that he could let go of right now. But he learned so many lessons from Branson, he’s just as genuine in person as you would imagine.

Zeb said that there’s a lot of examples of really exceptional entrepreneurs. Everybody looks up to people like Steve Jobs and Elon Musk and these people largely did business right. They created exceptional businesses and have a huge shift in changing the world. Richard Branson certainly did that. But he also is an example of doing everything else right. He has an amazing family, but he also treats employees right, some of the highest employee satisfaction ratings of any businesses. When you look at airlines, look at train companies, all of the stuff that he’s in, extremely high satisfaction rates from employees and customers. Zeb believes Virgin Experiences are next to none, the best customer experience that you’ll have in an airline or when they had their stores, you always have that exceptional customer experience and he’s been able to have fun, he’s been able to create joy. So, it doesn’t have to be all about business. It doesn’t have to be 100 percent of your time dedicated to work. But you need to have some balance now. It changes as you go. Zeb explained that he is not in work life balance mode right now, but he will be sometime in the future. And Branson is a great example of somebody who did that well.

Final Thoughts

It goes back to just repeating yourself, that’s probably the best guidance Zeb would give himself early on. Instead of saying something one time and assuming that a year later those people still know that don’t assume and just completely repeat, repeat, repeat, especially in your vision, especially in your core values. Things like urgency is huge for ClickUp, so they always drive that home. Communications at the end of the day is exactly what people think. You don’t know what somebody else thinks until they communicate that to you. It seems simple, but that means that if you really want somebody to know what you’re thinking, you’ve got to over communicate. You’ve got to repeat yourself.