Block's CTO reveals a counterintuitive lesson: reorganizing from a GM-based structure to a functional one (where all engineers report to one org) was the key to their AI transformation. This structural change had a greater productivity impact than any specific AI tool they implemented.

AI is a 'hands-on revolution,' not a technological shift like the cloud that can be delegated to an IT department. To lead effectively, executives (including non-technical ones) must personally use AI tools. This direct experience is essential for understanding AI's potential and guiding teams through transformation.

Gumroad's CEO credits their rapid development to his role as a solo decision-maker. This structure eliminates the lengthy processes of gaining internal buy-in and creating extensive documentation (PRDs, specs) common in larger organizations, which are often more about alignment than execution.

Simply instructing engineers to "build AI" is ineffective. Leaders must develop hands-on proficiency with no-code tools to understand AI's capabilities and limitations. This direct experience provides the necessary context to guide technical teams, make bolder decisions, and avoid being misled.

The "ICCPO" (Individual Contributor Chief Product Officer) model requires leaders to use AI tools to self-serve answers directly from company data. This shifts the executive role from pure delegation to hands-on experimentation, modeling a culture of self-sufficiency and inspiring the team to adopt new tools.

Gamma maintains a flat, high-impact organization by eschewing traditional managers. Instead, all leaders are "player-coaches"—they actively contribute as individual contributors while also mentoring their teams. This keeps leadership close to the work and empowers teams to adapt quickly without top-down commands.

At Crisp.ai, the core value is that the best argument always wins, regardless of who it comes from—a new junior employee or the company founder. This approach flattens hierarchy and ensures that the best ideas, which often originate from those closest to the product and customers (engineers, PMs), are prioritized.

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.

Contrary to the popular bottoms-up startup ethos, a top-down approach is crucial for speed in a large organization. It prevents fragmentation that arises from hundreds of teams pursuing separate initiatives, aligning everyone towards unified missions for faster, more coherent progress.