ClickUp SVP Engineering Shailesh Kumar Isn’t Surprised Productivity Apps Are Worth $1 Billion or More

“The Blind Ambition with Jack Kelly” provides a candid look into the top tech companies. Go behind the scenes with tech and workplace leaders and explore engineering and work culture, what it takes to land a role at these companies, and how to build, scale and succeed as an engineer or technologist.

Shailesh Kumar is the senior vice president, engineering, at ClickUp. ClickUp replaces all the individual workplace productivity tools in a unified all-in-one productivity platform, everything from project management, document collaboration, whiteboards, spreadsheets and goal tracking.

Below are some highlights of the podcast featuring Shailesh. Listen to “The Blind Ambition with Jack Kelly” above or on your favorite podcast app.

Why productivity software is so popular now

There is a strong focus on productivity, especially post-COVID when all of us are working very remote… What has resulted is that you have a plethora of applications… doing specific things… They want to give you functionality so that you can do your work better.

[But the] result is that [at] any company… you have at least 15 different tools… doing different things… and none of them talk to each other. So when you want to update something, you have to update it in different places. It’s very difficult to get a 360 view of your organization or how the work is getting done, and that eventually results in [a] loss of productivity…

It is very important to have an integrated platform to be more productive. Otherwise, you will spend a lot of time just navigating between different systems and lose a lot of time.

Is productivity software just hype?

I think the productivity space is still very strong… Anyone who is at mid-stage and beyond… will continue to do very well.

I see a lot of consolidation… where a lot of small companies will get acquired by mid-sized or large companies… I don’t expect any mid-sized [or] large companies to struggle in the productivity space.

Is now a good time to work on productivity software?

… When the money [capital] dries up, the good [companies] shine. I think true innovation will come out now. People will focus on true innovation—things that really differentiate and solve the business problem versus just taking capital and trying to build something… to attract users.

Now, we have to think about how to truly innovate and solve people’s problems in a way where it makes [an] exponential difference—not incremental difference—it’s got to be like 5x, 50x, 100x.

How to find the best productivity software company to work at

Ask questions. Ask a lot of questions.

Most of the time, [as job interviewers], we don’t want people to be surprised when they come in. So we are very, very honest about the state of the architecture [and] infrastructure… because we want the candidate to make a very informed decision…

Ask as many questions as you can about the infrastructure, the architecture, current scale challenges that they’re seeing, what’s the biggest problem they’re facing… and how did they solve it? What’s the company’s priority?

You should look at the real… growth numbers in terms of new users that are signing up. Are you seeing a lot of churn? If you’re seeing a very high degree of churn… that is an indication that there is something off.

What does it take to be an engineering leader?

If you want to be in a senior leadership role, you need to have a lot of experience [in] having done and seen different things… Because you have to have the experience of building a foundation. Experience builds… on top of a foundation so that you can go on the journey.

I advise people that collect experiences: Don’t collect years. Years will come by automatically… Collect as many experiences as [you can]… in as little time [as possible].

Anyone who shows ownership is always given more and more to do. By doing more, you will get more experiences, and you will get [exposed] to harder problems… Following through all the way to the end not only gives you the experience but also gives you the credibility to get the next one.

ClickUp Careers: How to become a stand-out candidate during the job interview

I get impressed when people have done their homework in terms of the market, why they are joining this company, and have done some analysis and [are] asking some hard questions.

[When] they ask [deep] questions, I get very impressed that they’ve done their homework [and are] genuinely interested in the company.

I like when people ask me hard questions during the interview:

What are [some] architectural challenges?
[What are some] infrastructure challenges?
Why are customers churning?
Why are they not sticking with the product?
Which type of customers [is] sticking with the product?
Where are you seeing your biggest challenge in the next two to three years?

ClickUp Careers: How does ClickUp hire engineers?

We have some creative ways of course sourcing… We do not only look inside the U.S. but in other places [around] the world. The focus is to find the best talent wherever they are.

We also look at… open source libraries. We take a look at the top committers.