Offer upsell when add to cart button is clicked?
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Is anyone aware of a solution where if someone adds an item to their cart, a popup would open offering a second item for a discounted price? In the popup they would have the option to either take advantage of the offer or they can dismiss the popup and either continue shopping or checkout.
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There's no account profile built in features or options available to support what you have in mind.
You may find what you're looking for via a 3rd party shopping cart or else have something custom developed. I've seen what your looking for in some of the major online retailers however, have not come accross that feature in in any off the shelf cart applications, at least not yet.
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I would ditch Paypal in a hot second if another payment transaction provider offered a good upsell solution.

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