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 'Competitive' Isn’t a Compensation Philosophy Ask most executives about their compensation philosophy -- whether at startups, private, or public companies -- and you'll hear some variation of "we pay competitively” and/or “we pay for performance." Press for specifics—competitive means which percentile? Performance measured how? What happens when market rates and performance signals conflict?—and the answers often reveal that what passes for philosophy is really just an ac

If your team is so important to investors, what are the criteria that investors look for when assessing a team? 

For in-demand skills, equity premiums could be as much as 150% higher than average.