What is the biggest pain for a CEO?
It’s always recruiting.
And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it Unicorn, IPO’d, or figuring out how to get to $5m to $10m ARR … the pain is the same. Recruiting.
Over time, that’s recruiting more and more senior folks, so the target changes.
But it never ends.
As your company scales, you’ll start to hit 15%+ attrition in your employee base just naturally each year. It will take a while for that to happen, but it takes its toll. Your managers will handle this part, but it will be a lot of work to support the processes here just to keep up.
And even your best VPs will often want to do something new in 4–5 years. That seems like Forever in the beginning, but later it won’t. Others will need to be topped. You’ll have to be recruiting new ones all the time.
Your best directors that can’t get that promotion to VP? They’ll move on, too.
And folks won’t work out.
That means you are constantly recruiting. The bigger you get, the more you need to do here.
You need to get good at it.