Introduction

Shailesh Kumar, Sr. Vice President of Engineering @ ClickUp, joins us to share his insights on scaling eng orgs efficiently & cost-effectively. He reveals his strategies for gaining customer insights, identifying areas to invest in, navigating cloud cost efficiency, and optimizing your software & performing a software audit. Additionally, we cover approaches to balancing headcount & team efficiency, creating clarity around a problem, increasing the net output of your eng org, identifying where / when to add headcount, and making your EPD flywheel run smoothly.

ABOUT SHAILESH KUMAR

Shailesh Kumar is the Sr. Vice President of Engineering at ClickUp, leading the Engineering, Security, and IT operations for the company. He has more than 18 years of experience in building large-scale organizations and cloud platforms for high-growth enterprise companies, including his role as VP of Engineering at Mulesoft (and Salesforce post-acquisition) and Head of Data Platform and Server teams at Tableau.

"You have to force yourself in having a discipline of asking the hard questions about all those ideas. What's the impact? What's the revenue goals? What's the target market? How much time are we talking about? The ideas are plenty. There are a lot of great ideas. You have to figure out which great idea is gonna turn into the highest revenue and that's a very hard exercise. I've seen many leaders know that they have to do that, but not do that very diligently and in a very disciplined way.”

- Shailesh Kumar   

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SHOW NOTES:

• Shailesh’s paradigm shift regarding scaling / eng org efficiency @ ClickUp (2:32)
• How Shailesh is navigating ClickUp through the current cost-sensitive market (4:46)
• Cost-effective areas that eng leaders should consider (6:55)
• Shailesh’s recent insights on how to better serve customers (8:43)
• Strategies for identifying areas to invest in & navigating difficult conversations with customers (10:02)
• Questions to assess challenging areas (16:44)
• Optimize your software & perform a software audit (18:49)
• Tips on building teams to optimize engineering efficiency (20:07)
• How to balance headcount and team efficiency (22:37)
• Shailesh’s approach to challenges around team efficiency (24:22)
• Frameworks for creating clarity of a problem / vision & refocusing a team (25:59)
• What makes an EDP flywheel run smoothly (27:39)
• Tactics to help increase the net output of your eng org (28:48)
• Strategies for hiring without losing efficiency & identifying where to add them (30:36)
• Frameworks Shailesh uses before adding a new function to the eng org (33:32)
• The story behind building out the TPM function (35:18)
• Rapid fire questions (38:24)

LINKS AND RESOURCES

• Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity - Snowflake CEO Frank Slootman is one of the tech world’s most accomplished executives in enterprise growth, having led Snowflake to the largest software IPO ever after leading ServiceNow and Data Domain to exponential growth and the public market before that. In Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity, he shares his leadership approach for the first time.

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/