Pros
Ashoka operates with clarity of purpose but also allows employees to experiment and play the mission out in ways that are empowering. I was able to work in a variety of roles during my time there which helped me grow professionally. Most of my work truly stretched my abilities even at the Associate level. Because everyone at the organization is expected to contribute to fundraising, I now have insight into that process and experience working with major donors that is very valuable. Ashoka's network of Fellows are inspiring and can be a strong part of your network even when you no longer work at the organization. There is a lot of opportunity here to make a difference if you're able to navigate the organization and its substantial networks.
Cons
Yes, the pay is low but check out the IRS form 990 and you'll see that it is at least quite equitable. And, sure, it's a place led by the visionaries and dreamers...but not every organization needs to be led by process. There is, therefore, a bit more hassle when it comes to getting things done logistically but I never had any real trouble and it didn't see a major difference here from my previous private sector employer.