I don't have an answer, but I might have a path to an answer. There's a fantastic Slack community of customer support/success people and they're very supportive

I don't have an answer, but I might have a path to an answer. There's a fantastic Slack community of customer support/success people and they're very supportive of newcomers: https://supportdriven.com/groups/ https://supportdriven.com/groups/ Many have worked through the same problem as your friend.