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Couriers appear in the side mission, Spy Games, where you must follow him to a location. The speed and sight range of the courier changes between missions.
Depending on which mission of spy games you are doing the reaper courier may be able to spot you even from up high if you peek off the edge. Stay to the train tracks/high buildings and use your minimap to follow him. Every now and then he stops and spins around a bit. On the ground these are the times he will most likely spot you. Try to remember these spins. When the courier reaches his destination he deposits a package. Wait a bit more for him to round a corner before picking up the package regardless of what the screen says. When he is gone get the package and go around the corner and kill him.
If he spots you he takes out his bombs, growls, and charges. If you are on higher ground he stays below you and eventually explodes, making you fail the mission.