The Remote Work Tribe Podcast: Kyle Racki

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In this episode of the Remote Work Tribe podcast, we chat with Kyle Racki, Co-Founder and CEO of Proposify. We talk about his journey as a founder, leadership and coaching strategies, the importance of having the right people in the right roles, AI, and more.

Episode Timestamps:

  • What is the most exciting thing Kyle is doing right now? (0:32)
  • How has his role as a co-founder evolved? (1:20)
  • What led Kyle to delegate less and jump back into the business? (2:46)
  • How did COVID and the tech boom impact Proposify’s growth? (4:46)
  • Knowing what he knows today, what would Kyle do differently today, looking back to 2020? (6:35)
  • The transition between running an agency vs. Proposify. (7:52)
  • How did he realize he needed to go full-time into Proposify? (10:12)
  • What roles did Kyle hire for at the start of Proposify? (13:00)
  • Kyle’s leadership style. (14:20)
  • What does he look like when hiring managers and execs? (16:25)
  • How do you ensure the right people have the right roles? (20:30)
  • The manager myth and what to do about it. (23:05)
  • Coaching strategies for managers and executives. (24:37)
  • How to run 1:1? (26:51)
  • How is AI shaping culture at Proposify? (28:28)
  • AI today and in the future. (33:08)
  • Lightning round questions (36:45)

We hope you enjoy it!

Links mentioned on the podcast

By Sebastian Cuervo