In my company, we are still pretty traditional in the way we learn. We have implemented an eLearning library, blended learning and we are currently working on adding more content like self-made videos, etc.
Currently, we are implementing a project that combines eLearning on negotiation with coaching elements. I really like the idea of it because it combines digital learning with a very personalized support of implementing the gained knowledge and skills. I would not yet call it a success but it has a clear potential to be one. At least, we gained some top management commitment on Training new ways of learning which is already a success in itself.
Challenges are manifold. The biggest challenge is workplace learning and making sure that the learner gets the piece of learning exactly at the time that he/she needs it. Relevance is the only way to really make people learn. Apart from that, employees need to understand what self-directed means and how to use the different technologies.
One of my major learnings so far was that pushing out content to many people at the same time (even if it's great Content) simply doesn't work. You need to make it really relevant (see above) to each single one of your employees in order to make sure that they invest time in it.
My recommendation would be to identify leaders in the organization that know what the challenges of their people are and that recommend digital learning items to them - ideally based on a very individualized career development plan.