We studied a case of a school in a high need setting that undertook multiple simultaneous initiatives during a major school reorganization. We focused on the simultaneous implementations of two comprehensive initiatives, one related to ambitious mathematics teaching and one related to the Understanding by Design curriculum writing process. We explored the extent to which educators in a mathematics department saw these initiatives as aligned or in tension. The results show that simultaneous ambitious initiatives may ultimately be mutually reinforcing, especially if grounded in common principles. We also found that initial tensions existed and diminished both initiatives at the outset.