[KingOfCoders]

Rewrites are dangerous for companies. They cost time and their benefit is small at best, often they leave the system in a worse state, see "Things You Should Never Do, Part I" [1]. As a CEO I would be very suspicious if a CTO rewrites the stack.

That said I did come into companies as CTO where I should have started a rewrite. The code plainly was not able to scale the way it was written. We had lots of trouble with scaling and I struggled balacing feature pressure and technical rewrites of parts of the code base in order to scale. Getting in and start with rewriting the code base for 6 months so it would scale would have made things much easier for all developers.

As a CTO coach this is also what I tell my coachees now :-)

[1] https://www.joelonsoftware.com/2000/04/06/things-you-should-...