If you hadn't mentioned his occupation of interest I would of said that he looks like an intimidating bodyguard with his tattoo covered torso and that slanted expression in his eyes. Even in a nice shirt and suit he looks very over-bearing. Maybe this is a good look to relate to the at-risks teens, as he has the same defiant look as any radical teen. A good example to the concept of 'appearances can be deceiving'.
He apparently is a very good person to shoulder a job of protecting and preparing them for their own future.
I like the photos in general but the first seems to have a busy background with that grid while the second has a solid background as a door which in fact I think is better.
Hope he succeeds!