COO of Headspace: Why You Should Re-Recruit Yourself

COO of Headspace: Why You Should Re-Recruit Yourself

From Best Manager Ever by Annie Riley

March 18, 2026 · 50 min · Season 4 · Episode 1

About this episode

Annie Riley interviews Karan Singh about effective management during times of change and the importance of re-recruiting oneself to their role.

What does it take to lead through 15 years of pivots, mergers, layoffs, and massive growth— without losing your people (or your mind!) along the way? Annie Riley sits down with Karan Singh, co-founder of Ginger and COO of Headspace, to unpack why great managers win people over through curiosity and genuine connection, how managers need to learn to ride the “J-curve” of change, and why everyone should re-recruit themselves to their role.  Timestamps: 00:00 Meet Karan Singh 04:30 Learning to manage on the fly 07:20 Winning people over 09:25 The mindset for surviving startup chaos 12:01 The j-curve of change 14:41 Speed vs. Space: giving teams time to process change 18:32 Healthy departures  22:24 Creating a “Next Play Plan”  26:49 Why you should re-recruit yourself 38:52 Rethinking PIPs: What most people get wrong  Join us on Substack  Level up your leadership skills with Fort Light  Connect with Annie Riley Connect with Karan Singh Nominate Your Best Manager Ever Best Manager Ever is a Production of Fort Light and Now It’s Hear Hosted on Acast. See acast.com/privacy for more information.

People in this episode

Host: Annie Riley

Guest: Karan Singh

Topics covered

  • leadership
  • management
  • employee engagement
  • change management
  • startup culture
  • personal development

Keywords

  • leadership
  • management
  • recruitment
  • change
  • startup
  • employee retention
  • mindset
  • curiosity
  • connection

Mentioned in this episode

Organizations: Headspace, Ginger, Fort Light, Now It’s Hear, Acast

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