This video shows proper pit person procedures by an experienced crewmember on the Reichel Pugh 77 JELIK. Notice how she keeps her eyes on the bow team at all times. She lets the halyard down only as fast as the bow team can gather the old jib. Also notice how she uses progressively fewer wraps on the winch. In the beginning there is a lot of load on the halyard so she uses three wraps to control the speed of the drop. As the sail comes down the load on the halyard is reduced and she goes to two wraps and finally to one wrap. Also notice how a “helpful crew member” tries to tell her what to do 32 seconds into the clip and she pays him no mind. Instead she is watching the bow team all the time.
A pit person always needs to watch what is happening at the other end of the halyard, not down at their winch. The only time for the pit person to look down is when tensioning the halyard to the final inches of trim where they get the mark on the halyard to the appropriate position on the measurement scale.
I saw a well organized pit person once who had a WetNotes note book with halyard settings for each headsail in a range of wind conditions. And since the pit person also controlled the outhaul and inhaulers and jib cars, her notebook had those positions for the full range of wind conditions. Notes like those give the back of the boat confidence that the boat will get up to speed quickly coming out of a mark rounding where there is a spinnaker douse and jib hoist. While those noted positions might not be spot on for the given sea state or tactical desire to point or foot based on boats nearby, they will make sure the boat is very close to optimal settings.
When the pit person is tailing the halyard, give them room to swing their arms out their sides, which allows them to move more line than pulling into their chest. It is important that the pit person keep up with the mast man.