The chapter explores the journey of two individuals from the early days of creating Vagrant to founding a startup called Keep, showcasing how their skills complemented each other in developing tools and services. It delves into the evolution of the CEO role within the company, the challenges faced in commercialization models, and the decision-making process in seeking outside leadership due to lacking experience in enterprise sales. The story unfolds as they navigate hiring a Chief Marketing Officer and a Chief Sales Officer, focusing on the dynamics of relinquishing control and the importance of shared values in forming a positive leadership dynamic.

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