My advice is to find someone that's done this before and have a good long chat with them. The advice from random hackers in their thirties isn't going to be all that useful.
That said, here is my take:
I know that if I were hiring him it would be easiest if it was for a role that had programming plus something that involved his past. That way I may have a junior software developer, but since he's writing code for our financial models in Excel his history as an CFO really comes in handy. You get the idea. I wouldn't throw this guy knee deep into Node / Python / React / CSS / HTML / Shell / Docker / AWS and expect him to thrive. Pick something focussed and relevant and he can slowly shift towards where he would be happiest.
That said, here is my take:
I know that if I were hiring him it would be easiest if it was for a role that had programming plus something that involved his past. That way I may have a junior software developer, but since he's writing code for our financial models in Excel his history as an CFO really comes in handy. You get the idea. I wouldn't throw this guy knee deep into Node / Python / React / CSS / HTML / Shell / Docker / AWS and expect him to thrive. Pick something focussed and relevant and he can slowly shift towards where he would be happiest.