Pros
Most of the reviews here are very positive. They aren't untrue: The people who work here are smart. and there is specific culture that many thrive in.
Cons
In my experience, the people who struggle at Transcend 1) often come directly from working in schools or youth-serving organizations, and/or 2) don't have certain cultural markers in common with everyone else (one or more of: studied at Harvard or the equivalent, worked at TFA, experience with certain charter networks, experience in management consulting). Both of these were true for me. The organization is racially diverse but not experience diverse. The emphasis of the work is on system-wide change, not on teacher practice – so if that's your interest, this might not be the best fit. The language, work habits and general beliefs about education would be familiar to people who have experience with the wider Teach for America world; if you are anti-TFA or are unfamiliar with that space, this might not be the best fit. There's also a lack of transparency about compensation, which is an equity issue, but maybe that's changed since I left.