Scale Up Practically for Success With Shailesh Kumar, SVP and Head of Technology, ClickUp

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“If you’re building something unique, if you’re building something very scalable, [and] if you’re giving all the flexibility to the engineers to make decisions, I think it does fire up people and they are excited to join.”


What creates growth in a company — a flashy or a practical approach? Shailesh Kumar, SVP and Head of Technology at ClickUp, contends that a practical mindset helps companies scale. He also chats about how to organize teams, help them run efficiently, and set up a system so that different teams can learn from each other. Also, Shailesh shares a little about his passion for woodworking.


Key Insights


Why Is It Helpful To Be Practical When Scaling? (08:16)


“And as you are scaling, there are tons of services out there that you can just plug and play. Do not reinvent the wheel. There’s no point. This is something I tell everyone. ‘Don’t reinvent the wheel… Always look out and see if there’s something out there that we can onboard and solve your different problems.’” 

If you can find an already existing product that works, then your team is freed up to pursue solutions for even higher-level problems. 

What’s a Productive Way To Run Teams? (14:22) 

“We’ve got operationally very efficient. So it means that… every team… operates their own stack now. They move towards services based architecture. Every team owns their own services. They’re operating it. They have dashboards so that they are reviewing their services.”

According to Shailesh, each team has a level of independence and ownership of their work, but they also have a process to take time to learn from each other. 

How Does Shailesh Attract and Retain Talent? (23:09) 

Shailesh describes his belief that having talented people on the team draws in more talent. He also leans into telling a narrative about ClickUp that he sees as attractive to potential employees.   

“I think everyone loves to come and build stuff… The story that we sell is… if you think about it, that for any engineer to come in and build the foundations of what [the] next five, 10 years would look like is just amazing.”

About the Guest:

BiO: Executive engineering leader, passionate about scaling organizations from product to process to people. Experienced in building large-scale SaaS platforms for high-growth enterprise companies as an engineer, architect, and leader. Delivery experience on all deployment models from on-premise to public cloud, private cloud, Government Cloud, and shipping an appliance.

Successfully incubated, grown, and led high-performing global engineering teams (US, Canada, Argentina, India) in hyper-growth enterprise companies by building teams and setting up the right processes. As a leader, I provide technical vision, strategy, and organizational leadership and have successfully led large enterprise companies into a different market with new products.

Currently leading global engineering, infrastructure, security, and IT at ClickUp, the fastest growing productivity platform.”

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Episode 380