This is an interesting problem, I might start by having ChatGPT try to infer a complete list of tools and skills each position involved along with a confidence score (even those you didn't originally tell it about)

From there you could allow it to remix the skills while maintaining an average level of confidence greater than some number: so it'd be allowed to include things slightly out of your wheelhouse only if most of the job skills matched up perfectly.

You wouldn't need the math to check out perfectly there, the score would just be a heuristic it could use internally