Damian is one of my favorites, but he is not made for teams -- leader or not. It's the way he was raised, and one thing I don't think he'll unlearn. His type of commanding confidence, decisiveness, and self-assurance may be fantastic for leading loyal troops, but... it's terrible for a collaborative team.
He's one of those characters that excels in small, equal team-ups, such as with Jon or Maya Ducard. Jason's similar in this respect, with his best working relationships being with the Outlaws and his bestie team-ups with Arsenal.
Doesn't make either of them bad; just gives them a different niche, which is always welcome.