When should I try upsells and cross-sells in my business?

There are a couple of strategies to offering upsells/cross-sells to your customers that work with Ontraport

1. Directly after they purchase product X - or when they download a leadgen - you offer them an additional product. Buys X - upsell Y. You can add an unlimited number of upsells or downsells - if they get X, upsell Y; if they don't want Y, downsell them Z, etc. The initial purchase for the upsell has to be done via a credit card gateway - anything but PayPal Standard. The reason is that they only give their card once and the additional purchases are charged to the same card immediately.
2. After they've used the product for a while - via a sequence. Buys X, wait 3 days - upsell Z. You can use any payment processor you like, even PayPal Standard.
3. Triggered by the fact that they've visited a specific set of pages - visits X + Y + Z, buys Z, offer X+Y at a discounted price. You can use any payment processor you like, even PayPal Standard.

When to do it is a question that depends on your business, price point and contacts.

1. Only do it if the product that is upsold makes sense to the first one - it has to upgrade the experience. If you buy a fishing rod from a store, they upsell you some hooks, not a baseball bat.
2. Upsell from a lower package to a higher - they get a Basic X, sell them Premium X - list all the additional benefits from the Premium upgrade.
3. Upsell them more of the same - it can be offered as a gift to someone else, bulk pricing, etc. "Get a second X for just 25% more!"