Clocktower... and probably Tim. Dick may know too if he wrote the seekrit check, but it might be more interesting if it was Tim who financed it. It does seem like more his style, and he would have access to the funds. I'll wait to let Bill weigh in on it.
Dick's like, "Yay, we dated. Fiery redhead. Safer as a friend."
I do like the idea of his relationship with Vale for now being only with Nightwing, and let her antagonize Wayne Ent's CEO later on for added drama and complication!