Just watched another founder rush into a CTO hire because investors kept asking about it, only to realize they actually needed a senior engineer who could also talk to the board. The desperation hiring that happens around this magical employee count is wild.
I want to get real about this - I hired a "CTO" at 17 people because I was tired of being the only technical voice in investor meetings. Worst $180K mistake ever. Turns out what I actually needed was confidence to say "I'm the technical founder" instead of apologizing for not having a fancy title structure. The real kicker? Three months later I had to let him go because he kept trying to rewrite our entire stack.
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