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The Daily Bolster

Deep Dive with Chad Dickerson

Dec 8, 2023
Chad Dickerson, former CEO of Etsy and a seasoned CEO coach, dives into the intricacies of leadership and innovation in large companies. He shares personal insights from his transformative time at Yahoo!, focusing on the challenges of transitioning from CTO to CEO. The conversation also touches on his unique approach to balancing fiscal responsibility with compassionate leadership through his coaching work. Listeners will learn about the emotional weight of being a CEO and the critical importance of self-awareness for sustainable leadership.
43:17

Episode guests

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Quick takeaways

  • Chad Dickerson's unconventional journey from journalism to tech highlights the importance of proactive learning and adaptability in career transitions.
  • Emphasizing people and culture in technological challenges, Dickerson shares insights on leadership effectiveness and the significance of self-care for CEOs.

Deep dives

Career Transition into Technology

Chad Dickerson shares his transition from journalism to technology, emphasizing the unconventional path he took after graduating with an English literature degree. Initially working in a clerical role at a newspaper, he capitalized on the opportunity to learn about web development while working in the newsroom during the early internet era. His proactive approach and eagerness to learn led him to self-teach SQL and back-end programming, eventually positioning him for a career shift into technology. This early experience in a rapidly evolving field set the foundation for his future roles in tech leadership.

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