With enterprise software, the end user is almost never the actual paying customer, which when you are trying to make really end-user focused products that delight in the way Apple do, can lead to incentives that prioritise enterprise needs over consumer - look at the huge number of enterprise specific features Microsoft historically have built, that have affected consumers too. Jobs loved making consumer products so much, I can't imagine he ever would have been able to really chase enterprise customers.
The move to targeting services and enterprise more at Apple happened under Cook, because, well, he has to continue growing the company and Services + more engagement with enterprise markets have been critical to growth post Jobs under Cook. Perhaps Steve ultimately would have done the same as Cook, given iPhone can't grow forever etc, but it would have been a major shift in his opinions/outlook for Apple.
I'm talking about "Enterprise" in the traditional software industry sense, which is not the same industry apple target for creative professionals, even if tools like MDM etc can overlap. Jobs loved "professional" users in creative industries, not enterprise volume sales and fleet management tools etc etc.