Akhil Gupta on navigating uncertainty when transitioning roles


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In Episode 10 of Lead Time Chats, Jean Hsu, VP of Engineering at Range, chats with Akhil Gupta — formerly VP of Engineering and GM at Dropbox — about how to navigate uncertainty when transitioning to higher impact roles. How do you know when you’re ready for that next role? How do you fill in gaps, and when do you take the leap?

Akhil started his career at Google, and was a Principal Engineer by the time he left for Dropbox. At Dropbox, he grew the infra org from just 10 engineers, and stepped into the Head of Infrastructure role, then VP of Engineering, and then GM and VP of Enterprise.
Jean and Akhil discuss:

  • Akhil’s transition to management at Google — going from 0 to 40 direct reports!
  • How to surround yourself with people who are rooting for your success, as you transition to greater impact roles
  • The biggest challenges of transitioning from a functional leader to a cross-functional leader (i.e. VP of Engineering to GM of Enterprise at Dropbox)
  • What relationship-building looks like when your org has thousands of people, and 1:1s won't scale!

34 episodes