THE #1 WORST HIRE OF ALL WHEN YOU ARE JUST STARTING TO SCALE: THE MEDIOCRE VP OF ENGINEERING

Summary from the TLDR Founders newsletter

The worst mis-hire for a startup is an ineffective CTO, as it stifles innovation. A good CTO must be a skilled hacker, not just a manager, to maintain the "magic" of the codebase. A mis-hire in this role can lead to stagnation, making recovery difficult.