Does winston jump further when looking up?
Solution 1:
Winston always jumps in the direction he's looking, so by looking up you're going to be jumping straight up instead of forward. So no, you're definitely not jumping farther by looking straight up.
As always, the angle that will land you farthest from the starting point is 45°, so look "halfway" up if you just want to cover as much distance as possible on a flat plane.