Because you should always be asking yourself, if everyone in a senior role is the right person for the next stage. Including you.
Most of your VPs won’t scale all the way from $1m to $100m in ARR. So you need to both help them scale, and also, make sure you hire above them if necessary so the business does not stall out.
This may also be true of you. It may not be.
But as a founder — which also generally means you are both a very large shareholder and perhaps the single person most invested in the success of the company — you have to ask yourself the same question.
Having said that, if you aren’t 95%+ sure someone else could do the job better, then usually, don’t go beyond the exercise of challenging yourself. Instead, bring in a COO, a magical SVP, someone to help carry the load.
A CEO doesn’t have to know everything. She just has to be able to recruit the best people possible at each stage of the company’s existence. And the longer you stay CEO, the better you will get.
So if the time has come, then yes, give up the reigns to someone better, than can take it to the next level. That’s what’s best for you, the company, everyone.
But if you are just tired / burnt-out / frazzled. That’s not a sign to bring in a CEO, not usually. It’s usually a sign to bring in more help.
A little more here: I’m Tired of Running My Successful Start-up After X Years. What Should I Do? – SaaStr