When do you know it's time to move on versus digging in and trying to shape an org or a role the way you want it?

You move on.

If you haven’t found success or there isn’t a concrete plan to change things it sounds like you have outgrown the role/team/company. It could be for a variety of reasons, some of which are outside of your manager’s control. There may also be a disconnect between your vision of the ideal role and what the organization needs at the moment. 

I would ask myself - if this isn't what I want to do, is it worth sticking around?

Career development is not a ladder but a winding path so there is never a clear cut answer that I can share. However, I tend to push people to answer the following questions when deciding whether to stay or move on from a role:

• Am I challenged in my current role and still learning new things?

• Am I happy working in my current role? 

If you answer “yes” to these questions, I would lean toward staying in your current role because it means that you will continue to grow professionally and it is a good environment for you. 

If you answer “no” to any of these questions, it tends to mean that you are potentially ready for that next challenge.