Are people with dark personality traits more likely to succeed?

It doesn't "only matter" in relationships that are horizontal on the org chart. They're just not the totality of the non-peer relationships. Understanding and communicating boundaries between teaming and exercising authority is key to efficiently moving everyone toward a target.

To torture the sports team metaphor more, the captains on a team are players but also an authority among the players. To the front office, a coach is a member of the gameday team.

I think it's interesting to focus on Success, and then consider two types: a) Success for personal benefit, b) success achieving a higher purpose.

(Intentionally referencing film characters)

Success for personal benefit may be illustrated by Jordan Belfort in Wolf of Wall Street. He succeeded in becoming, for a while, the type of wealthy person he imagined as a young man that he wanted to become.

Success achieving a higher purpose may be illustrated by Terence Fletcher from Whiplash. He succeeded in turning musicians with talent into accomplished performers.

Both personalities could be considered 'dark'. One succeeded by being a charming pathological liar. The other by dismissing any sense of empathy and driving others with severe, manipulative criticism.

But in the end, it was type a) that eventually flamed out and type b) that had an enduring impact on his profession.

I think the notion of 'how to get the most out of people' actually depends on the people you are trying to get the most out of. Many musicians quit under Terence because the achievement was not worth the suffering along the way. Others were motivated to excellence by his style, and he didn't care that they hated him for it.

I heard Steve Rinella talking about this as it relates to hunting. He spoke about how there's some trips where you're miserable in the moment (cold, bug-bitten) but when it's all over you have fond memories of the experience and consider it worthwhile.

If you mean specific to Jobs, I don't have any and was just trying to relate to the OP comment, which is why I couched it with the caveat that I have no insight into his psychology. Maybe he generally was happy during the moment and maybe he was actually miserable when reflecting on his life, I have no idea.

> Maybe the comparison between "dark traits" and "light personalities" yields this, but its been shown pretty consistently that higher agreeableness (more empathy) has a negative effect on salary, primarily for women.

You seem to be comparing apples and oranges: I do not think "higher wellbeing" is the same thing as "higher salary," and whatever correlation there is due to the stress of being poor (and thus is less and less signficant as salary progresses past a minimum threshold).

I wouldn't conflate emotional intelligence - i.e. the ability to modulate behavior based on person specific interactions - with necessarily possessing negative, vindictive, malign or cruel personality traits. That's definitely a stereotype.

It is entirely possible to be charming, without secretly being cruel or vindictive. Yes, it can be more difficult to judge a disarming person's intentions, but that doesn't mean the person is inherently sadistic or ill willed. Perhaps they are just good at making other people feel comfortable.