Warning: this is going to sound very opinionated and I'll admit it is:
Any CTO should know that rewrites are death. Real software professionals have understood this for near 20 years now, if not longer. Few people have a great success story coming off a rewrite and dozens of failures (dead bodies since literally these companies went out of business) litter the road.
For an early opinion: check out Joel Spolsky's comments from 2000 at joelonsoftware.com/2000/04/06/thin...
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