If you haven’t already, I suggest that you look up Lynn Conway, Dr. Margaret Stumpp and Stephanie Battaglino.
Conway joined IBM in 1964, but was fired in 1968 when she told management that she needed to transition. After transitioning, she returned to the workforce as Lynn. However, she did officially come out until about 1999. He website http://www.lynnconway.com documents her career and activism work.
Dr. Stumpp was a VP at Prudential when she transitioned.
Stephanie Battaglino transitioned while working at New York Life. She has written a book: Reflections From Both Sides Of The Glass Ceiling.
All 3 are retired now. Battaglino’s book pretty much chronicles her entire life: childhood, adolescence, work life before transitioning, work life after transitioning and activism work. She lives a couple of towns over from me and I met her at a presentation about her book.