To transition from working 'in the business' to 'on the business,' Snowflake's CRO was told his hands-on, 'deal hound' approach wouldn't work at scale. The solution was to hire other capable 'drivers,' trust them to do their jobs, and hold them accountable. If a leader has to do their team's job, it's a problem with the team member.

Snowflake's CRO, Chris Degnan, kept his job through multiple growth stages where he could have been replaced. His longevity wasn't due to a pre-existing "scale" playbook, but his intense coachability and ability to "morph" and adapt his strategies based on direct feedback from the board and new leadership.

The leap from a hands-on marketing leader to a C-level executive is less about tactical skills and more about personal growth. It demands a shift from execution ('doing the work') to leadership ('inspiring people'), which requires self-awareness, authenticity, and dropping 'professional walls' to build genuine connections.

A common failure mode for new CROs is attempting to create the sales playbook in isolation. Core pillars like ICP and value proposition are company-level decisions. The CRO's role is to be interdependent, facilitating this cross-functional creation process, not dictating it.

The CMO transitioned from a hands-on "doer" to a strategic leader not gradually, but through a pivotal team reorganization. This structural change reassigned ownership and forced him to empower his directors, shifting his own focus from execution to shaping and inquiring.

At the VP or C-level, a leader's primary role shifts from managing their function to driving overall business success. Their focus becomes more external—customers, market, revenue—and their success is measured by their end-to-end impact on the company, not just their team's performance.

The shift to remote work unlocked a global talent pool. For specialized roles, the advantage of hiring the best possible person, regardless of location, is far greater than the benefits of in-person collaboration. The leadership challenge shifts from managing location to enabling distributed top-tier talent.

To make a split US/UK leadership team work, Enara Bio's CEO focuses on creating a deep "sense of belonging" for remote executives. This goes beyond logistics and time zones. The core challenge is making geographically distant leaders feel fully integrated, empowered, and part of the company's fabric from day one.

After burning out, MongoDB's CRO Cedric Pech realized a leader's most crucial asset is perspective. He deliberately stays in Europe to create a 'caution of protection' from the tech echo chamber. This distance helps him maintain balance and a clearer perspective, which he believes makes him a more effective leader than if he were constantly immersed.