If you sign up a new member in the tasting room and give them their club release, you can mark the order in Vines OS as part of a club order.
In Settings > Settings Manager, scroll down to the Wine Club section and turn on the ability to do so.
After the POS order has been completed and it is synchronized, in Vines OS, go to the Order and select "Make this a club order". Choose the club shipment it should be tied to. Then select the Member whose account it is tied to. It should automatically associate it with the new member. NOTE: this will move the revenue from being POS revenue to Wine Club revenue in Vines OS Statistics.