Most founders and investors understand that organizational needs evolve as companies grow. What's less understood is that these transitions cluster around specific headcount ranges, each requiring fundamentally different strategic approaches to compensation, compliance, and organizational infrastructure.

Over my years of advising technology companies through critical growth phases, I've observed a fundamental tension: while the tools and constraints of scaling have transformed dramatically, the underlying organizational challenges remain remarkably persistent. The question of how to coordinate increasingly complex activities across growing teams—what Baron and Kreps identify as the central challenge of organizational design—continues to define success or failure in scaling v

Why is compensation is more crucial than ever for investors assessing startup teams? The tech talent market has shifted dramatically.