Uploaded November 2025 | Updated September 2026, 1 week ago

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The hardest part of transformation is knowing what to let go of.

Dan O’Connell, now leading Front as CEO and formerly on the board at Dialpad, joins Joubin Mirzadegan to explore the delicate balance between legacy and innovation as he leads a decade old company through the AI revolution.

He also reflects on why courage and control can coexist in leadership, and what it means to “make decisions that give you energy.”

Guest: Dan O’Connell, CEO of Front

00:00 Intro
05:57 Navigating Company Culture and Change
10:46 The CEO's Perspective
19:43 Career Choices
39:24 Work-Life Balance
58:37 Hiring and Company Culture
59:10 Final Thoughts and Gratitude

Connect with Dan O’Connell
X: https://x.com/dialdoc
LinkedIn: linkedin.com/in/droconnell

Connect with Joubin
X: https://x.com/Joubinmir
LinkedIn: linkedin.com/in/joubin-mirzadegan-66186854
Email: grit@kleinerperkins.com

Learn more about Kleiner Perkins: kleinerperkins.com