Regarding onboarding I think one thing you can do is be smarter about the trial period. I will often signup for things and not get around to properly trailing before the trial period runs out.

No doubt if I email you you will give extra trial period, this could be done automatically though with an accompanying follow up email to reengage. As you would be tracking usage metrics anyway there would be plenty of data to decide if I have properly trialed the full capability of the software or not.