Pros
I was surrounded by some of the best, most hardworking, and most creative people. Even on days that the work was tough, I was always happy to walk into the building and be surrounded by such a hardworking group of staff. The Employees are incredible, too. While not all 90 Employees are life-changing, it is quite likely that you will meet a lot of people that you connect with deeply every new six month recruiting cycle. I was a coach of up to 20 Employees at one point, and working with all of them was such a joy, even if not all of them were successful. I was happy to take late night phone calls, text thoroughly, and answer any question I could - or direct them to someone who could - because of how compelling all of the Employees were. The Employees are also incredibly appreciative of the work that you do for them; it's possible that you're the first person to stick your neck out for them in a long time if not ever. While the work can be really challenging - I would have to "fire" 5-7 Employees every six months, many of whom that process is extremely devastating - you're surrounded by so much to feel great about. I had people who cared about me on staff, some of whom were helpful in moving my career along. While I didn't connect super closely with my first manager, she was incredibly skillful and I learned a lot from her. I was much closer with my second manager, but didn't find him to be very supportive. Oh, I forgot! the benefits are incredible. Almost enough to offset a very meager salary.
Cons
Year Up has a few separate components: there's program (which encompasses the entire Employees experience, from recruitment - employment placement), operations (which runs the staff management and building operations), development (fundraising), and corporate engagement (who bring in internship and hiring partners). Depending on where you are in the organization likely goes a long way in determining how long you can last there.