It should go without saying that in order to be a successful wine sales representative, you should love discussing, handling, learning about, and drinking wine. Almost as obvious is the fact that you should have good sales skills, as well. Wine sales reps sometimes must work very hard to succeed, and they often have numerous duties they must perform as part of the job. But for those with a passion for wine, getting paid to be immersed in wine culture makes the hard work worth it.