Trac Bannon: I generally don’t make cold calls, at least when it comes to inviting folks to be on Real Technologists. Jess Szmajda and I crossed paths through our online cybersecurity and cloud computing networks. She’s a general manager at AWS leading Network Firewall and Firewall management business. Previously, she was the GM for the VPN practice.

With her online profile saying she’s located in Washington, DC, I made the assumption that she works with the federal government. Oops! Never make assumptions! 

I could tell there was technical depth and a driving passion to impact others. 

It was time to set up a chat. 

When we met, it was during late August. The air was still warmed by the summer sun, and the evening was just beginning to hint at the cooler days ahead. Perfect weather for an energizing discussion and forward thinking ideas. 

Jess Szmajda’s presence was an instant uplift. She has a delightful laugh that punctuates many of her sentences. 

Jess Szmajda: Well… I was actually born in the district. I think I was one of the five people born in DC that year. 

 I’m a general manager. I own some of our network security services… network, firewall and firewall manager. A general manager at AWS is a bit like a CEO of business line. So I’ve got a couple products that I own and responsible for P and L and… all people sales, go to market, customer support, everything you name it. I lived in or near DC for most of my life, and I’ve never worked for the government. I don’t know , the government thing, it’s just never made sense. It’s never been the place for me. 

Trac Bannon: So many of the professionals in my network who are in Maryland, D. C. and Virginia region have ties to the U. S. government in one way or another. Being a direct government employee often requires educational pedigree. Jess’s journey includes being self taught after being kicked out of the University of Maryland. 

She’s a bit of a technology nomad. It probably stems from her childhood. There is an interesting trend with real technologists that they’re often musical. This rings true for Jess. 

Jess Szmajda: I grew up in Maryland, in Prince George’s County.

And I went to high school at Suitland High School which is right outside the district, right outside southeast DC. And when I was going to high school, it was a rough time. There was a lot of murders and a lot of bomb threats and all that stuff. I originally went to Suitland for just the general, high school.

But eventually I quickly joined the music program. And so I was actually a music major at Suitland. I was a saxophone and bassoon primary and I played just about everything else… I played for the DC Youth Orchestra. I was the principal Bassoonist for a while. 

I went to college to study music composition and computer science. And I wanted to write video game music actually. 

So I was a big old nerd, a big old music nerd. 

Trac Bannon: Jess is the oldest of three children in her family, having two younger sisters. Her introduction to computers is one of the most unusual I’ve ever heard. Her father gave her a few basics and she ran with it. One of her motivations was to be cool. Now, I don’t mean cool like the Fonze in Happy Days or Neil Patrick Harris in “How I Met Your Mother.” I mean physically cool. 

Jess Szmajda: I, I had a computer when I was six, so it was an old 286. And like my family could afford a computer, but that’s about it. And so the computer was actually the air conditioner. And so if I wanted to stay cool in the hot Maryland summers, I learned how to mess with the computer 

Trac Bannon: Jess got inspiration from the Children’s Television Workshop through a popular magazine called “3-2-1 Contact”. It had a variety of content that encouraged scientific inquiry and exploration, including experiments kids could do at home. And, you guessed it, BASIC code. Her love of gaming and access to online bulletin boards led her to discover an attractive subculture called the Demo scene. 

Jess Szmajda: The demo scene very short is… people used to crack games and they would put like a little intro at the front of this game being like, oh, you know, super cool lead hacks war cracked this game.

And so then people were like, oh, I like making those intros. I don’t care about cracking the games. And so there’s this whole like music and art kind of cultural movement that happened in the late eighties, early nineties, actually through the nineties in Europe, mostly Finland, called the demo scene.

And I got really interested in these demos and so I taught myself to code in order to make wild and crazy art and music and stuff on computers.

Trac Bannon: Jess is the first born of three siblings, and there are many traits that we ascribe to first born children. A small sample includes being responsible and reliable, conscientious and a high achiever. This fits Jess well. But there is another very complex dimension to Jess Szmajda that drove her passion for computing. Her gender identity. 

Music and computers were her passion as a kid. It was a creative outlet. 

Jess Szmajda: I was, uh, very much a loner of the three… so, uh, something about me, I’m trans… and so people at that time thought I was a guy, and so I was the only boy. And I have these two younger sisters who were very close and I am, you know, unconsciously struggling with all of that gendery stuff.

And so I’m like losing myself in computing as much as I can to avoid the world. 

Trac Bannon: Our society and culture, at that time, lacked the lexicon to help Jess rationalize and realize her identity.

Perhaps that’s what would draw her towards expressing herself in a mixed way as androgynous. We don’t hear that term much anymore. When someone has a combination of masculine and feminine characteristics in their appearance, in their behavior, in their identity, they use that term. Cultural icons like David Bowie, Prince, and Grace Jones are often celebrated for their androgynous style and the way they challenged and played with gender norms.

Jess Szmajda: In high school, I was obsessed with androgyny. I didn’t have this idea of transgender at the time.

I, you know, looking back… I think I realized when I was eight that I wasn’t a boy. I had this buzz cut and I was so depressed about it. I was like, this is the worst thing in the whole world. Um, yeah. You know, in high school, I, I really embraced androgyny. I had long hair. I was kind of a goth.

I was, you know, whatever. A, uh, distancing myself from expectations. And then I think, after college… I eventually got the job where I was doing that, like DevOpsy stuff. And at that point I was like, well, I should probably man up and figure out how to like fit society’s expectations.

Trac Bannon: Jess entered her university career presenting the gender identity of a male and seemingly drowning herself in gaming, much to the dismay of the university faculty. Countless hours of playing Diablo and EverQuest while battling depression was not the mix needed for academic success. At the end of her first year, with failing grades, she was asked to leave. She eventually found an entry level job in technology and told herself, in her own words, to man up and figure out how to fit into society’s expectations. It was 1999. She cut her hair and tried to fit in for over 18 years until she transitioned. 

Jess Szmajda: I transitioned in 2017. So it’s been a while now, and I think I learned a lot about myself through that journey.

And I feel like I have a much better handle on who I am now. But even so, I’m still searching… I think for some of that… like I, for a very long time I thought… I wanted to do good in the world and to try to help as many people as I could. And so for me, for a very long time, that idea was like, oh, I’ll run for office and I’ll go into politics… I know, and, uh, I’ll be a Congress person. And so I was like, oh, that’s, that’s my life’s goal. And everything I had was sort of working backwards from that long-term goal. Yeah. And then, I don’t know, at some point over the past couple years, I’m like, well, I don’t know, doesn’t seem like I’m gonna be able to do as much good there as I would hope… not to get too political. But, so lately, you know, I’ve been trying to find out who I am in that lens of like, how can I sort of like do the most good in the world?

And I don’t think I have an answer yet. So it’s an interesting journey of discovery there too.

Trac Bannon: Jess’s parents were very upset when she failed out her freshman year. As their firstborn and biological male, they had placed immense traditional expectations on her. So she enrolled at Montgomery County College. Her logic was that perhaps a change of setting would make a difference. Jess Szmajda just did not do the work. She would show up for world religion and listen to the interesting lectures, but did no work. Then came an offer in tech that carried an incredible salary. It was a NetOps type role doing windows and Unix system administration. Why pay to learn if you can get paid to learn? 

Jess Szmajda: I got a job offer also and they were like, oh, I will pay you… I don’t know, was it 50,000? …which at that point was like amazing for me. And I was like, well, I could either pay a bunch to learn stuff or I could get paid to learn stuff and so I’m gonna go get paid to learn stuff.

And that was pretty great. This was, uh, a really funny name for a company called GIS trans.

Trac Bannon: Jess has always set her own path and has also been lucky if you believe in that sort of thing. I don’t. To me, luck is when opportunity and preparedness meet. She took a role supporting the Chief Architect at a company called Allegiance Internet.

She was writing DevOps type scripts to automatically build and manage server infrastructure. When that chief architect left, she was able to step into his role. In the crazy IT mergers and acquisitions that followed the dot com bust and Y2K, Jess found her employer changing multiple times and eventually being laid off.

Jess continued trying to live a traditional lifestyle, including a traditional marriage. When the layoffs happened, her first wife convinced Jess to move with her to North Adams, Massachusetts. Remember the Demo scene that captured Jess’s attention in late high school? 

There was a website scene, music.net. It was early internet streaming radio, and the demo scene had a chat feature on the website. This is how they met. They began dating, separated by an 8 hour commute, just moved and married. In Massachusetts, Jess would first work with Betterway. net and own the wireless ISP account for BioTest Laboratories.

She would make the jump from Betterway to BioTest as chief architect and the head of engineering. She would also ride out in the world. Ending her first marriage while with BioTest and meet her future second wife. 

Jess returned to DC and dove into the local tech community. 

Jess Szmajda: So I was going to the local Ruby Meetups in the DC area and being really involved in the meetup scene and the local tech community. And, I co-founded the DC Tech Slack actually. Uh, so it’s, I’m still somewhat involved in the DC Tech community. I met this guy Adam at the meetup. He was looking for somebody to be a technical co-founder… for what would become Uptoro. He and Toby and this guy Justin, had started a sort of like a eBay. They had stumbled into this problem of businesses having a lot of access and overstock… and things they needed to liquidate. And they had this vision for a tech platform that would help cut businesses with the returns and the overstock goods. And Adam had done a lot with Excel and Visual Basic, and I was very impressed. But it was not a technology that would scale. So, I joined those guys and we co-founded Uptoro. And Optoro now powers a lot of the top retailers, returns and overstock management systems. …um, Ikea, staples, BestBuy, Home Depot… 

Trac Bannon: As a co founder of Optoru, Jess is wildly proud of having grown the company to 300 people.

Optora was founded in 2010 and grew with Jess presenting as a man. The entire corporation knew her as a man. She married her second wife. It was not too long before the couple found that they were going to have a baby. Throughout her career, Jess has continued to struggle with depression. The pregnancy of her wife drove some incredible urges, from wanting to buy women’s clothes to shaving her legs.

She struggled and struggled. and struggled. 

Jess Szmajda: And I was like, this doesn’t make any sense, but I have to do it. I like felt this incredible urge to do it. And, um, I, uh, I later recognized that, uh, you know, with my kid coming along, I wanted to be authentic as much as possible… to my kid my entire life. And, I didn’t want them to see who I wasn’t. And I think deep down I recognized that I wasn’t the guy that people thought I was.

I didn’t know what I was, but I struggled with this from like 2014 to 2017. I was struggling so hard. 

Trac Bannon: With that dedication we ascribed to first borns, Jess started therapy. But she thought, this is stupid, it’s just some weird sex thing. But she persevered, and went back to the counselor a second time, thinking, why am I cursed with this? Why is this my path? and she kept going back.

Jess Szmajda: now that I look back on it and like, why am I gonna throw all that away to do this freaky, weird thing? And then by the third session I was like, well, this isn’t going away. I better face it. And so I decided to transition. And so I did this really silly thing where I went to some people I trusted in the organization. I was like, I heard somebody might be trans.

And they were like, really? Why don’t they just tell everybody . When I finally decided to come out at work… I’d been six months into taking hormones and I wrote an email to all staff on Friday telling them about my journey and that I would come in on Monday as Jess… and everybody was very supportive, so I didn’t have any worry that I’d be supported either.

I think at Uptoro it was a, a progressive, forward-looking company in a lot of ways.

Trac Bannon: When you found and build a company, you often pour your soul into it, so much so that your fingerprints are everywhere. From that lens, it makes sense that Jess would expect her company to be progressive and supportive. In Jess’s words and experience though, the bias is real and it’s subconscious. After six months into them seeing Jess as a female, and six months into taking hormones, she really started to pass as female.

And people started to not see her as a man. There was another cost though, her marriage. 

Jess Szmajda: I still love everybody I’ve ever said I love you too. It’s not that passion explosion, romantic love anymore, but I still feel that love, you know?

So I’ve never really been able to understand that falling out of love. It’s just an experience that’s completely foreign to me. When I transitioned, this was part of the conversation. She was like, you know, I’m straight and I don’t wanna be with a woman. I wanna be with a guy. And I was like, well, you know, I understand that, but that’s not who I am.

So when I decided to start transitioning, she was like, well, I guess that’s it. And it was very sad for both of us. 

Trac Bannon: All of these questions are complicated. It comes down to seeing people’s souls. I keep coming back to that. Seeing people’s souls. Understanding their journeys. Understanding who they are. Meeting them where they are. It seems simple to me.

For example, this can easily explain why Jess and the mother of her son continued to live together for a few years while her wife went back to school. She became a journal’s editor for the American Society of Clinical Oncology and then she got really interested in medicine and science. While Jess was transitioning, her ex wife went to medical school.

They lived together until she graduated and got her residency. They now co parent quite effectively. 

As Senior and I continue to meet more and more Real Technologists, our worldview and our own lexicon expands. We’ve learned a beautiful term through Jess, pansexual. It means being gender blind of someone’s gender identity or biological sex. Perhaps it means seeing and loving someone’s soul and character instead of their packaging. 

Jess met her current wife while still at Axios. Her wife is now the CISO for Zipline. Zipline designs, manufactures, and operates delivery drones. The company’s mission is to provide every human on the Earth with rapid access to vital medical supplies.

It’s quite an impressive mission. 

When Jess left Axios, she spent some time writing penning over 80,000 words of a book before joining Amazon in 2022. Her journey to Amazon came with a little bit of research, including reaching out to a woman, principal engineer. Considering that Jess has lived openly as a woman for only a few years, it was natural for her to then ask the about the engineer’s experience.

Jess Szmajda: I asked her, when I was thinking about joining Amazon, I was like, well, what’s it like to be a woman at Amazon?

She got very upset. She’s like, I don’t think of myself as a woman at Amazon. I’m an engineer. And to me, at the time I was like three years into my own womanhood. And to me like I’ve seen very direct bias in the tech industry for my transition. And so my entire approach to understanding a workplace, a lot, a lot of it, it comes like down to like, how much is that bias going to make my life difficult?

And I found that there’s so few, I think women engineers who’ve come into the tech workforce, like before… I dunno, name your cutoff 2005. And people who joined the tech workforce who were like, that sort of like the only, or like the whatever. I think have that more kind of approach that you’ve talked about here where it’s just like, I don’t want to think about my femininity in the workplace.

I found though that women who’ve entered the workplace more recently though, find that they want to make it a topic of conversation. And, I’m not exactly sure why it always is, but I think there’s definitely this, this era now that we’re paying a lot more attention to diversity and inclusion and equity in the tech space.

There is almost an opportunity to demand it and to put that like forward and be like, no, I am a woman in tech and I need to be recognized and accepted as that, as a core part of my identity. And I think it’s a really, it’s a fascinating change.

Trac Bannon: This is why diverse opinions matter. That’s not my experience. I don’t personally want to be known as a woman architect or a woman researcher. I am a Technologist, a Real Technologist. I control my adjectives. I control my pronouns. But the beauty is that we each have our own way that we want to describe ourselves and we should respect that of others.

Jess has joined the board for an advocacy and support group called Out in Tech. It’s a non profit organization that aims to support the LGBTQ plus community in the tech industry through inclusion, allyship, and leadership training. She is also accessible. 

Jess Szmajda: I always say yes to mentorship whenever anybody asks. I got where I am through figuring things out and I feel like other people need ways to figure things out and try ideas and stuff. So, yeah, as much as I possibly can… even if it’s like just a few messages on like a slack here and there, or, if it’s a longer term individual relationship. Yeah. It’s important to me.

Trac Bannon: When I asked Jess what is next, she surprised me to mention that she is going back to making music in her spare time.

She’s also hoping to make a difference wherever she goes. 

Jess Szmajda: I’ve been doing singer-songwriter stuff. It’s me and my guitar, and very lately I’ve been singing in a church choir, which I had never thought I would ever do… but I’m loving that. If I get the opportunity to change some people’s minds, that can have a really big impact on a lot of people as well. So I think that’s, again, idealistic and optimistic, but, uh, an opportunity that is present and presenting itself and… maybe things will change.

My girlfriend really wants to open a coffee shop, who knows.

Trac Bannon: Yes, Jess has both a wife and a girlfriend. After more than an hour with Jess, I found myself contemplating her trials, her depression, and her strength to make decisions, and that she found it to be true for herself. So what would she say to her younger self?

Jess Szmajda: It feels so trite, but, believe in your intuition I think is such a powerful thing. Especially when you question it and you’re dealing with depression a lot, you know, believe that your inner quiet voice is telling you something that’s worth listening to. I think it’s pretty valuable advice.