Coming Out Corporate

Know Your Rights, Community + AlliesSkylar Kergil
Image by Rebecca Lieberman

Image by Rebecca Lieberman

By Skylar Kergil

Odds are, you’ve never heard of a “Gender No-Match” letter; though you probably have had an awkward boss.

As someone who came out as transgender within two different corporate environments, I’ve experienced both—along with a fair share of other challenges and victories related to expressing my identity on the job.

From those Gender No-Match letters to awkward bosses and beyond, here’s how I navigated two coming-out experiences. My hope is that my story will serve as a resource for trans folks and employers alike, along with allies, friends, family, and those who are new to thinking and talking about transgender issues and questions about identity.

I. The Supermarket & the Gender Marker

It was June of 2010. I had just turned 19. My recent (and noteworthy) achievements included having my legal name change completed (September 2009), top surgery (December 2009) and my driver’s license and passport updated to reflect a gleaming M in the gender box (April 2010).  

Eager to make some extra cash, I reapplied to work at the supermarket where I had worked all through high school. I also missed the community there; the people were awesome and accepting. They called me “Skye” when I was 16 trying to figure things out, and had my name tag changed to “Skylar” when I was 17. They were like a family—both employees and shoppers alike.

After a week went by working there (as Skylar now with the gender box checked M), I was asked to come in to have a meeting with the store’s new manager. I sat in the break room with my old boss and a newer manager, who were both very quiet. They said that they had an issue with my application: my driver’s license indicated “M” but my social security card said “F.”

Truthfully, I hadn’t had any idea that my social security had a gender attached to it. Furthermore, it didn’t occur to me that a gender mismatch between two forms of ID would be so disruptive. And since it didn’t seem like a big deal, I tried to explain: “Oh! It’s because I’m transgen….”

The new manager cut me off, reaching her hands outward in what seemed like an effort to reassure me. “We don’t want to discuss that,” my old boss said calmly. “We understand this is a sensitive issue. We do not have the words to discuss that. We reached out to human resources and found out what you can do….”

Gender No-Match letters, once a deal-breaker in employment situations for trans folks, were thankfully amended in 2011. However, they can still cause issues.

The largest system used by private employers, the Social Security Number Verification System (SSNVS), eliminated gender in 2011. However, some systems used by state government agencies will still match gender against SSA records. If a person’s recorded gender with the submitting agency does not match SSA records, SSA may report this back to the submitting agency. In cases where gender data is submitted to SSA and does not match, the submitting agency is under no obligation to respond in any way. So long as the other personal data matches with SSA records, the organization can simply ignore the gender mismatch.


The potential for this issue to cost me my job was high. My boss informed me that I would need to have the issue corrected with Social Security. It is no longer required to have GRS (gender reassignment surgery) to change your gender on your social security card. Their website now states “medical certification of appropriate clinical treatment for gender transition in the form of an original letter from a licensed physician” is sufficient for changing one’s gender.

However, in 2010, they were very scrupulous about the specific wording of that letter. In the end, the doctor providing my hormone treatments wrote that I had completed GRS, which wasn’t true by medical standards at that time, and was eligible to change my passport, SS, license, and other forms of official government ID.

Honestly, I believe that on that third attempt at solving the problem, I had simply been lucky to find a compassionate customer service worker at the SS office. The fact that chance and luck were integral factors to my keeping my job did not reassure me. By the time SS updated my sex, it was already mid-July, and I was promptly hired now that the issue had been resolved.

What my bosses learned: That one of their employees was and is transgender, and that talking about transgender issues without any relevant knowledge can be awkward. Also, they learned that the Gender No-Match system created a problem for them that they didn’t understand or even want to engage with—though they couldn’t find a legal way around it.

What I learned: When I began switching my license and passport gender markers, I should have immediately changed my Social Security records as well. Having a letter from a physician affirming my gender transition plus an updated passport were all I would have needed. However, the SS office I went to seemed unaware of this specific procedure. This letter required by a physician should be made standard and more clear so that time is not wasted during the process.

II. The Bank & the Resume

Three years later, in 2013, I graduated from college. Heading out into the world, I applied for a day job as a bank teller to allow me to focus more on my writing and speaking career. When I applied for this position, I gleefully noticed this disclaimer at the bottom of the application:

Creating a respectful and welcoming workplace for our Lesbian, Gay, Bisexual, Transgender and Ally employees is important to us. That’s why we’ve built a work environment where all of our employees can be comfortable bringing their whole selves to work.

During my in-person interview, I casually covered up my thumb tattoo. In three years, no one at the bank has noticed it (until maybe now!) and yet that was all I was nervous about during the interview thanks to that awesome clause in the job description.

Despite how green I was in the workforce, there were a couple of speaking gigs I had done at some pretty well-known organizations and educational institutions on my resume. The manager raised his eyebrows at them, seemingly impressed that a person who had just graduated college was already being invited to colleges to lecture and speak.

“Wow! What do you do at these gigs?” he asked.

“Well, I often discuss my transition from female to male throughout high school and college…”

“Really?! No way! That’s cool!” chimed the head teller who was sitting next to me during the interview. (We ended up being friends.)

The manager turned a bit red and stumbled on his words a little in response. Overall, however, he was accepting. Like my first boss, I didn’t think he had the words to discuss my transition with me, but he was at least open to listening, and I felt that acceptance right away, even if it was implicit.

In fact, I know in hindsight that he didn’t have the words yet because he proceeded to reach out to human resources after I was hired in order to ask for advice on what to do to create a more welcoming environment for me. (Though it already was welcoming.) He wanted to help me feel included. (I immediately felt included.)  Finally, he wanted more information about how they, as my employer, could help assist me in my transition. (I was already done with my transition, living fully as male at that time.) It was an appreciated gesture on his part; I could tell he was trying his best.

Human resources at my bank has an awesome guide for transitioning in the workplace. It goes over what store managers should (and shouldn’t) do, and mandates asking the employee who is transitioning a series of questions to discover supportive strategies.

Should there be a public announcement? One-on-one announcements? Should we offer direction on how to deal with telling customers when inappropriate customer/employee situations should be reported or escalated? Can we help them navigate the health insurance benefits that entirely cover all transition-related expenses?

The only aspect of the process that really required anything specific of me was telling my coworkers about my past so that they were aware and better informed. I had several customers who had seen my YouTube videos and would remark on them while I was at work. To avoid awkward circumstances of my coworkers being like, “H on earth does so-and-so know who you are? You just moved to town!” I told them right away about my night job as a YouTube personality.

“Oh yeah! At night I have been recording YouTube videos documenting my transition from female to male over the past six years. That’s also why I sometimes take time off to go speak or perform at a school,” I’d explain.

My coworkers appeared to accept me right away, and I think it helped immensely that I was open with them—and that they were open with me. One male co-worker seemed uncomfortable at first, but he never, ever disrespected me. Perhaps conversations he had with my boss behind closed doors helped. Perhaps he was always extremely uncomfortable and yet managed to treat me with the same level of respect as he treated all of the other men and women at our workplace. All I know for certain is, the bank I worked for had set it up that any intolerance would not be tolerated and I felt safe.

What my bosses learned: They had an environment set up to welcome, accept, and embrace transgender employees. They had resources already created to help assist in the process of providing a safe work space for a transgender employee.

What I learned: If I do not want to disclose my transgender status, it may be easiest to remove all traces from my resume about it. Yet, had I gone to an all women’s college, would I have lied?

Every coming out experience is unique. Please feel free to write in and share any successes or issues you have had with coming out or transitioning while having a career at  

These things are never so simple, but the more we can explore and discuss them, especially our experiences with them, we can help the future navigate these waters.


Skylar Kergil is a transgender singer-songwriter, activist, educator, writer and artist who is from Acton, MA but currently resides in Boston. After high school, he attended Skidmore College, serving on the board of the Pride Alliance, as a Peer Mentor, and an active member of the community until graduating on May 18, 2013 with honors and leadership awards. While he majored in Studio Art with a concentration in drawing and photography, he pursued a wide range of classes and interests in gender studies, environmental studies, philosophy, poetry and biology. As of now, he is traveling to educate, working on his music, and writing a book about his transition through high school and college.