The autopilot can keep the boat pointing wherever you like, but there's absolutely no reason to point into the wind to furl the headsail, it will furl fine at any point of sail. In fact we never put the boat head to wind for that (main is a different story).
Then the crew takes control of the working sheet and eases it out until it begins to lose power while I stand on the aft deck (centre cockpit) and pull the furling line. I look at the headsail to see if we're getting a good furl while she looks at me to see how much I'm grimacing, which tells her if it's going too hard and she needs to ease more or take a turn off the winch
On a good day, we've get the big 150% Genoa furled away in what I'm guessing is maybe around 30 seconds or less.
When doing it on my own, one hand has the working sheet to ease and the other the furling line to pull. Since the furling line has a turning block, I can have both lines at a 90 degree angle to each other, meaning I can pull on the furling line with both hands without letting go or losing control of the sheet. Takes a bit longer on my own as the process is less smooth, but works fine too. Probably this way it takes about a minute.