Explore the challenges and strategies of leading engineering teams in cloud environments through this insightful 18-minute conference talk from the Cloud Native Summit. Delve into the fundamental questions of cloud computing, including its nature and location, while learning how to navigate the complexities of the modern tech landscape. Gain valuable lessons from Abbie O'Rourke's experiences scaling organizations and transitioning to a small SaaS company, Arlo. Understand why cloud migration is never a simple "lift and shift" operation and discover effective approaches for helping teams thrive in this dynamic field. Recorded at the Cloud Native Summit in Wellington, New Zealand on September 5th, 2023, this talk offers practical insights for engineering leaders and managers working with cloud technologies.