Wynne Nowland Talks About Being One of the Few Openly Transgender CEOs in the World

Everyone should have the freedom to come out on their own timeline, whether they’re four years old or 104 years old. For Wynne Nowland, coming out at age 56 when she was the CEO of insurance and financial services firm Bradley and Parker was a unique experience. “You’ve all known me as W****, but tomorrow morning I will arrive to work as Wynne,” read her email to her staff the day before she first arrived at work as the real her. In Nowland’s conservative industry, she expected pushback and was surprised at how little she got.

Nowland sat down to talk with OFM a little bit about her experience of being one of the few openly trans CEOs in the world to come out.

OFM: So, talk to me a little bit about your background, how you came to be CEO, Bradley and Parker, and what exactly that does.

I have been CEO here since 2017. It is an insurance and financial services company located about 20 miles outside of Manhattan. I’ve been with the firm for about 30 years, so a long time. Most of my background, most of my professional career has been here, although I did make a couple of shortstops elsewhere before I landed here.

What was what was the experience of coming out at 56 in your position then?

Of course, everything I’m saying that was just germane to me because I know a lot of people in our community do not have good experiences. But I was very fortunate in that I had a very positive experience coming out, not only in my personal life, but in my professional life as well. And I think that one of the interesting things about that is this is typically a very conservative industry. And I think the automatic assumption would be that it might be more difficult in this kind of an industry than a more liberal industry, entertainment, advertising, things not so buttoned up as finance and insurance. But my experience is extremely positive. And that was from various sectors. So my own team here was very supportive. Our clients were supportive, as well as our vendors and business partners. So, for me, it was a very positive experience. Now, we all know there’s haters out there. That’s not to say that there weren’t a couple of nasty emails. That’s not to say that, after I was profiled in the journal, we didn’t get a few nasty phone calls. But I think that that those kinds of outliers exist anywhere. But my face-to-face experience with people that I knew was very positive.

You certainly had certain advantages that not every trans person as being in a certain position of power. Do you think you would have been harder if you didn’t have that?

No question. I like to recall a story that happened. At the time, I was in the midst of the final portion of my transition, and doing my legal paperwork here in New York state, which is a pretty friendly state to do this stuff in. But I was going to the motor vehicle department to get my license changed, and I’m a very organized person by nature, and I had everything exactly laid out the way it needed to be done, and went to the line, and to the employee who was supposed to process the change on my license.

One of the documents we need here in New York is a letter from a doctor that you’ve medically transitioned. And the worker from DMV accused that letter of being a forgery because it wasn’t on letterhead. My doctor’s practice, like a lot of businesses now, they just generated letterhead off the computer. And I can remember, that was a real sobering experience as to how my privilege had helped me. I’m a pretty big presence. I’m very confident. If you come at me rather than recoil, I usually tend to double down.

So you can imagine my argument to this employee was considerable. And I ended up working out getting it done. But I remember as I was leaving, saying, I wonder what would have happened if I was a trans woman of color and was 19 years old. I would not be walking out with this document. So I’m well aware of my privilege. And it undoubtedly has made my experience easier than some others have had.

Do you think there’s room for more transgender people to take positions of leadership and business? Or do you think there’s going to be too much there would be too much pushback on?

My experience in business, I haven’t seen that kind of pushback. Again, I’m coming at it from a slightly different level. I also think there were some realities that we need to keep in focus. And it’s one of the things that I think is crazy right now regarding all the political turmoil and the assault on trans rights right now. Not that our rights aren’t important—They are-but with all the troubles we have in the country in the world right now, why these conservative crazies are focusing all this attention and all this energy on a problem that they’re creating, where it only affects, I think it’s less than 2% of the public–it may not even be that much—is kind of mind boggling.

But by the same token, you know, if you have 100 positions of authority, you just took a sample of 100 positions of authority,  you’re not going to see 20 trans people in there because we’re simply not that big of a portion of the population. So I think that it’s hard to identify from a number standpoint, because we are such a minority. But I think what companies need to do is to is to encourage diversity and inclusivity in their hiring practices and in their promotion practices. And if they do those things, not to the exclusion of people, then the trans people and other underrepresented groups will get to their appropriate point.

My sense of things in the business community is not that companies don’t have these policies on the book. Most companies, once they reach any kind of size, have an employee manual, they have anti-discrimination policies, they have sexual harassment policies, they have all these policies. And they put them in a nice employee manual, and they distribute it out. And then they probably don’t do anything about it. So you can’t just espouse these things; you have to you have to act on them. It’s that old saying, you can’t just talk the talk, you have to walk the walk too.

Since you’ve come out, how has that changed just your daily interactions in your job?

I’m always the same person I always was, so I feel the same. I certainly feel better that I’m not juggling two personalities the way I used to, but I basically feel the same. One thing I have heard often over the last five, six years is that people think I’m more approachable now than I used to be. Of course, having a big ego, I can’t possibly think that’s the case. Why wasn’t I approachable before? But for some reason, that seems to have been a byproduct, which I guess is good.

Do you still have hope for the future right now in face of this recent tidal wave of anti trans legislation and sentiment?

It’s very disheartening. One of the reasons I came out seven, eight years ago, we were in a vastly different position than we are now. We were coming out of a time when there was a lot of positivity in the country regarding trans people and making them a part of the fabric of society. And certainly the last several years have been very, very disheartening. I’m lucky in that I’m having this conversation with you now, right outside New York City. This is, especially from a political leadership standpoint, a very democratic and liberal-centric area. So we have very good protections here in New York. We have pretty reasonable standards to to officially transition and get your documents straight and all that stuff. We have excellent health care regulations here regarding trans people. We have excellent social things regarding the never-ending bathroom wars. So here it’s a very comfortable existence for me. But I’m not going to Florida anytime soon.

So that’s super disturbing. And what’s amazing to me about that Florida law is it is just so draconian. They’ve used—I don’t think any definition is great—but they’ve used the most difficult definition of gender for anybody to pass. So, in other words, if somebody like me who, according to my state, has medically transition, has legally transition, has had their birth certificate changed, I still don’t meet the threshold for using the ladies room in Florida.

And to me, that is just crazy. It shouldn’t be labeled at all. But even if you were going to do it, there’s much better ways to do it than they chose. And it just shows me where their whole motivation lies. They’re not really looking to protect anybody. They’re just looking to promote hate. And it’s very, it’s very disconcerting. And what I think is equally disconcerting is, about seven, eight years ago, maybe a little longer, North Carolina had a similar bathroom bill, and there was a groundswell of public sentiment against that. Corporations threatened to move out of the state. Even Bruce Springsteen said, I’m never gonna play in that state again unless they repeal that law. And they did repeal the law.

And this thing in Florida, no pushback. So that, to me, is candidly more disappointing than the fact that they passed the law. It doesn’t surprise me that somebody like DeSantis does this. But it was surprising that the rest of the country that had, in the past, risen to these kinds of things has been really, really silent about this. So it’s very disturbing.

Do you see anything that that gives you hope for the future?

It’s really troubling right now. But this same troubling thing expands to so many other things in society right now. It just seems like we’re on this course that about half of the country is one way and half is the other. And instead of coming together, we just seem to be polarizing in these separate corners, and, as of right now, I don’t have a lot of hope. So it’s really a matter, for me, (of) being very fortunate that that I’m in a state that is in good condition. And the only thing I think we can do is to encourage the kinds of conversations you and I are having, and trying to get out there.

Of course, the problem is, I’ve been very lucky. In the past few years, I’ve been on a lot of top-tier media. I was in the Wall Street Journal; I was on Fox News—which by the way, you would think I would have been treated terribly there. (I) was treated splendidly there—and those kinds of things, I think, can be helpful because, since we’re such a low part of the population, the average person has very limited experience with trans people.

So when these guys demonize us, it’s kind of easy to get them on board because they don’t have anything personally that they know about. So I think the more that people get out there and talk about these kinds of things, we normalize that a little bit and make it less easy for them to just demonize people. I mean, the stuff they come up with, I’m sure you know, it’s, at best, half truth and, worst, lies.

The thing we hear about the bathrooms all the time, is that, if we don’t keep these people out of bathrooms, these trans people are going to be molesting people in the bathrooms. There’s zero evidence of that happening. Zero. And then if you talk about the medical stuff, they’ll talk about, “We’re doing this because we don’t want to maim our children.” I don’t think there’s a responsible doctor or responsible medical association in a country that is talking about maiming children and doing surgery on children. That’s not what medical intervention is for underage trans kids. But that’s what these people go out and say, and so that’s what the people believe that they’re going to take these kids that are 12, 13 years old, and perform all sorts of surgical procedures on them. That just doesn’t happen. It gets me crazy because we just know it’s not true.

Photo courtesy of Wynne Nowland