I can't answer as a CTO-like person, but I'm in an Architect-type role and deal with our CTO-like person on a daily basis. The high-level management cares only

I can't answer as a CTO-like person, but I'm in an Architect-type role and deal with our CTO-like person on a daily basis. The high-level management cares only about "The Big Rewrite" because it is the only thing that gets visibility at that level of the organization and it comes with a large budget that everyone knows will be replenished for years as it gets spent. Our CTO-like person has fully bought into this idea. We have too many projects and too few developers, so incurring technical debt is an everyday thing. It will be dealt with in "Phase 2" of the project, which all the developers know is something that never happens. From my vantage point - having one foot on the developer side and one foot on the management side, I see that the management thinks the developers are incompetent and the developers think the management is incompetent. It's not a good position to be in, yet at the same time we have a pretty laid back culture, work less than 40 hours per week, great benefits, etc. So turnover is fairly low. Most of the developers have either a side gig or are going to school part time, or else they'd probably go insane.