But aimed perhaps at everyone, not just the CTO.
In fact the CTO probably needs one thing on their checklist.
Checklist item 1: Hire an outside security auditing firm to report on the state of this checklist quarterly".
And if the company has the financial resources:
Checklist item 2: Hire a second, independent outside security auditing firm to report on the state of this checklist quarterly".
I don't see any value in relating anything to the financial stage of the company because it's irrelevant.
Security also needs a time and priority aspect to it. For example if your company hasn't done anything on the checklist yet then what should come first, what is most important? Also it would be good to know what are the biggest typical weaknesses - a security chedclist can have so much stuff on it that it becomes hard to know where to focus.