How do you know when the best time is to move on to a new role?

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CIO in Education, 1,001 - 5,000 employees
I think my best answer for this is that you will know and/or have figured out the signs. For me, it's varied from just having an empty or bad feeling in your stomach as you walk around the office, to figuring out that you're being ignored or that special project is never going to be funded. Lastly, people usually walk away from bad managers more than just moving on to new roles.
Administrative Manager in Construction, 51 - 200 employees
For me, I think the best time to move is when:
1: You can't find fulfillment in your present job
2: When you realize that there are more for you to do and yet your company isn't expanding. 
CTO in Healthcare and Biotech, 11 - 50 employees
In my case it has been when the environment or my Manager was so toxic that it accelerated the decision.

When the promises of higher roles/responsibilities aren’t met even though I have surpassed the objectives set to me.
CTO, 51 - 200 employees
This is something I've gotten a little bit more thoughtful about. In a previous role, when a lot of the senior leaders started leaving , I really dug in. I learned a lot through that. I'm grateful that I dug in at that moment. But I think for folks who are further in their career, staying wouldn't have made any sense as they could have gone somewhere that really impacted at a company. For me early in my career, that was the right thing. But now, if I were to do that, I think I would regret having done that.
You have to expose yourself to new experiences but don't put yourself in positions which are unlikely to go well. If your goal is to build out your network, you're not going to do that at a company that is about to run out of money and is shrinking. If your goal is to develop your leadership skills, it's really hard to do it when your team keeps turning over.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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