Despite being an expert, Jobs was also a perfectionist.

Should this sentence above be revised to maintain parallelism, though it would become wordier (see revised sentence below)?

Despite the fact that he was an expert, Jobs was also a perfectionist.

I don’t like either sentence. The “despite” is weird, because being an expert and being a perfectionist are not things that would be surprising to go together. Use “despite” when there’s more surprise:

Despite being a dog, Elmer only likes cat food.

Rebuild the original sentence from scratch:

Jobs was both an expert and a perfectionist.