Great question. I'd offer that primary aspiration is to start a conversation with your customers while they are on the trial. You need to do this in a way that feels natural and such that the customer gets to experience the full value proposition before trial ends.
So practically create a 'trial strategy' or 'activation strategy' ...however you want to call it. Over the trial period, list out the communications you will have with the customer, answering when (e.g., right after trial starts, after certain usage events, 3 days in, after period of non-usage), how (e.g., by email, by phone, by in-product chat, etc.), what (e.g., generic tips advice, specific advice related to what they are doing with your product, videos of how other customers use the product, etc.).