" As a company grows from 25 to 50 to 100 to 200 to 500 to 1000 people, the characteristics of who is the very best talent in leadership roles will change. It’s rarely the case that your leadership team at 1000 people is the same leadership team you had a 25 people. "
- Brad Feld

As a company expands from small teams to larger organizations, the qualities that define top leadership talent evolve significantly. Initially, when a startup begins with a few individuals, leaders often thrive by being hands-on and highly adaptable, driving innovation through direct involvement in various aspects of the business. However, as the company grows—from 25 people to over a thousand employees—the role of a leader changes dramatically. Larger organizations require leaders who can manage complexity, delegate responsibilities effectively, and foster collaboration among diverse teams.

The quote underscores that leadership is not static but dynamic and context-dependent. At smaller scales, visionary founders with strong technical skills are often the best fit for leading an innovative charge. However, as companies mature, the ability to inspire and lead large groups becomes paramount. Leaders need to develop strategic thinking, communication skills, and the capacity to build a robust organizational structure that can support continued growth and operational efficiency. This shift in leadership requirements highlights the importance of adaptability and continuous learning for leaders who aspire to guide organizations through various stages of development.

Brad Feld is an entrepreneur, venture capitalist, and co-founder of Foundry Group, a venture capital firm based in Boulder, Colorado. He has been instrumental in shaping the startup ecosystem both locally and globally, contributing significantly to the growth of numerous successful companies. His insights on leadership and entrepreneurship are widely respected within industry circles, making him a valuable voice for founders and leaders navigating the challenges of scaling up their ventures.