The demands of the CEO role—focusing on external stakeholders and high-level strategy—inevitably distance them from operational realities. This counterintuitive insight argues against the "Imperial CEO" model and highlights the constant risk of losing touch with the business.

Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.

As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.

Corporate leaders are incentivized and wired to pursue growth through acquisition, constantly getting bigger. However, they consistently fail at the strategically crucial, but less glamorous, task of divesting assets at the right time, often holding on until value has significantly eroded.

Business growth isn't linear. Scaling up introduces novel challenges in complexity, cost, and logistics that were non-existent at a smaller size. For example, doubling manufacturing capacity creates new shipping and specialized hiring problems that leadership must anticipate and solve.

The transition from 'deal jockey' to operator at a multi-billion dollar company took a visible physical and emotional toll on Snowflake's CRO. He lost his passion for the operational grind, leading to burnout. This highlights the importance of self-awareness for leaders in hyper-growth environments.