It is significantly more difficult to step in as a non-founder CEO than to build a business from scratch. The new leader must contend with inherited business inertia, a pre-existing culture shaped by the founder, and constant comparisons, making transformative change much harder.

In large companies, a culture of A/B testing every decision can become a crutch that stifles innovation and speed. It leads to risk aversion and organizational lethargy, as teams lose the muscle for making convicted, gut-based decisions informed by qualitative customer feedback.

Counterintuitively, the period of slower market growth was more fulfilling for Plaid's leadership. The hyper-growth 'summer' felt like just riding a wave, whereas the 'winter' demanded true innovation and customer focus, leading to a 'refounding moment' and increased product velocity.

Corporate creativity follows a bell curve. Early-stage companies and those facing catastrophic failure (the tails) are forced to innovate. Most established companies exist in the middle, where repeating proven playbooks and playing it safe stifles true risk-taking.

While processes are essential for scaling, excessive rigidity stifles the iterative and experimental nature of innovation. Organizations must balance operational efficiency with the flexibility needed for creative breakthroughs, as too much process kills new ideas.

The new CEO transformed DocuSign by making the product vision the company's "guiding light." This meant reorganizing so that sales, marketing, and go-to-market strategies all flowed from the product roadmap, rather than the other way around.

A CEO who stays too long creates an organization optimized to respond only to them, causing other skills and response mechanisms to weaken. Leadership changes are healthy because they force a company to develop a more balanced and resilient set of capabilities, breaking the imperial CEO model.

If a company creates a siloed "innovation team," it's a sign the main product organization is stuck in "business as usual" maintenance. Innovation should be a mindset embedded across all teams, not an isolated function delegated to a select few.

As companies scale, the "delivery" mindset (efficiency, spreadsheets) naturally pushes out the "discovery" mindset (creativity, poetry). A CEO's crucial role is to act as "discoverer-in-chief," protecting the innovation function from being suffocated by operational demands, which prevents the company from becoming obsolete.