If one has the ability to sell something at all, then that rates positive when considering sales someone must have ability to sell something. This definitive relationship rates positive in the grammatical and logical functions of language. One might call it pragmatic if applied to need. If I can sell you something you didn't have already and know you needed, meaning it changes your life for the better, then that should rate positive, all other philosophical arguments notwithstanding. An example of this might be selling a coat to someone when they hadn't realized how the cold they were. Now I know I am running up against some moral issues here, and a good deal of economic destruction has occurred based on the premise of filling an unknown need, which has been poignantly satirized in Dr. Seuss's The Lorax, but the Thneed was not the issue, it was the morality of production, and I'm not out to discuss the means of production. I simply want to recognize that the ability to sell something to someone with a positive outcome is positive, especially when it comes to linguistics.
If we revisit the cliche with ice and an Eskimo, then the relationship must be considered negative because the Eskimo has no need for ice, I don't think I have to explain why, but I'll say it's a scarcity issue. The Eskimo is not chosen to identify some racial characteristic but a socioeconomic geography indicator. One could easily substitute an race, ethnic group, or nationality commonly identified as living in a area with an abundant resource, e.g. vodka to a Russian, rice to a Chinese, or Californians to an Oregonian. The ability to sell something to someone is positive, but using that ability to sell anything to anyone no matter the intrinsic benefit rates negative. What must be considered at this point is the risk. This is where the cliches diverge.
The Eskimo would gain nothing from the purchase of the ice, but he would lose all of what he or she used to purchase the ice, unless the Eskimo purchased the ice with something of equal scarcity. Generally, the cliche means the salesperson not only has the ability but the gall to sell things to people without need or benefit to the customer. It's a criticism of amoral capitalism.
When you look the ketchup cliche, the need isn't implicit. We don't know the value, ie scarcity to need ratio, of ketchup or white gloves. This makes it equally glib but not equally critical. The woman in question could either need ketchup and is willing to take on the predictable risk of soiling her fine gloves, or she owns infinite white gloves, so she sees no risk in the ketchup purchase because she can change her immaculate gloves if they become soiled. In the case of this cliche, the salesperson comes out clean. They have sold something to someone with acceptable risk. We can only assume they've done so by making the risk look acceptable because whether it is or not does not appear in the cliche.
Both cliches suggest that salespeople are slick, but one critiques morality while the other does not. If you can sell ketchup, or a ketchup Popsicle, to anyone wearing white gloves, you're just a good salesperson, not a dick.