As a hiring manager, that is what I care about – can you perform in the role I need? In the business I am in, it is about knowledge and experience in business, not whether you are a CD/TG or on a transition path. Most of my clients could care less.
But as the other writer said, what you start with is the expectation you are setting for the employer. So if you start as a woman, they will expect a woman.
As Steven Covey likes to say, ‘begin with the end in mind.’ What is your goal? If it is to present as a woman, then present as a woman.
Good luck and let us know how it goes.