Mens Sana

30 Years

I’ve been in the tech industry now for 30 years. That’s wild. I don’t think most people think I look much more than 30 years old (I’m much older than that). I thought it would be fun to look back at the last 30 years in tech and see what patterns I can find…

The first thing that really made me love computing was the Demoscene. In the ’80s and ’90s, I dialed into random bulletin board systems, played games, read messages, and downloaded random files (I’m sure there were viruses in there somewhere). While doing so, I stumbled across things called “demos” - multimedia works of art that showcased what computers of that era could do. These demos were real-time renders of wild geometry set to music, and I was transfixed (check out Second Reality by Future Crew from 1993 - it’s still awesome to watch).

I voraciously consumed as much of the Demoscene as I could. Driven by the desire to create, I taught myself how to code and more importantly, how to make computers work. In the early ’90s, I parleyed this experience into a small business, helping my neighbors set up their computers to play video games and deliver on their small business needs. I was a high-school kid working nights and weekends on something that was just pure fun - technology was a joy for its own sake.

Back then, working with technology was purely about the joy of solving hard problems and making cool things. But starting in IT should’ve helped me see that the problems I was solving were all about the human need for joy or for better solutions to the problems they had. My early clients wanted help getting their video games working, or getting their printers to print their legal briefs. They didn’t really care about the technology in the way that I did. It would take me a career’s journey to discover that while technology is amazing, the real value of it lies in improving humans’ lives. Shiny new toys are just toys unless they’re applied to human problems.

A Wake-up Call

I worked in IT in college as well, at the campus career center. I helped people match their resumes to jobs, and eventually leveraged that database to get a different IT job at a GIS company, where I added Network Administration (Windows NT 4, HP-UX, AIX) to my background. Then some friends pointed me to a job at a big DC-area ISP, known as Digex.

I joined as a Systems Engineer, reporting to a guy whose title was Chief Enterprise Architect. I wrote perl scripts to automate Solaris builds - DevOps before we knew what that was, and for that time (the late ’90s), unheard of. I also went around and helped engineering teams think about how to leverage our servers better, and taught them about N-tier architectures.. also pretty forward-looking for the time. My boss pretty quickly left to join another company, and as nobody else knew what we were doing I inherited his title and became Chief Enterprise Architect.. a heady title for a young kid.

This was during the dot-com bubble, and companies were changing fast. As soon as I joined, Digex was purchased by Intermedia, then after about a year Intermedia was purchased by Allegiance Internet, and then very shortly thereafter Allegiance was purchased by WorldCom. WorldCom finally decided to look into what they’d bought, and so I was called into a literal meeting of “The Bobs” (if you’ve seen Office Space). “What do you do here?” “.. I write perl scripts to automate Solaris builds and help people with N-Tier Architecture..?” “That’s what we heard, well, your services are no longer needed here”. And with that, I was laid off. I went back to my desk and found that my Solaris workstation was just up and missing too.. a big surprise, but also an important experience in recognizing that just solving problems wasn’t enough.

The dot-com bubble was bursting, I was laid off, and I looked for work for months. I recognized that so many companies had built buzz around things that didn’t really solve problems for humans. The few companies that did survive that time were creating real value - Amazon, eBay, Yahoo - people wanted their services so those companies survived. That was an important lesson.

Disappointing WISP

For personal reasons, I moved to Western Massachusetts (I followed someone and got married.. then later divorced). I hung up a shingle and built websites in PHP - mostly content sites at the time. I then pretty quickly joined a group of other contractors called Betterway.net. We helped our book of clients with e-commerce and content websites, backup systems, and general IT help. We operated out of a relatively tall building in Adams, MA that was right at the bottom of a bowl valley. This geographic position made it optimal for building a wireless ISP, so we did that. I built a radio tower, configured security and networking backhaul across a mishmash of connections, and built a captive portal system. At the end, I could go anywhere in town and get a fast wifi connection - unheard of in 2004. We even got local press coverage! All that was left was for my business partner to turn it on.

Which he never did..

I still don’t really know why - it was crushing to have my work never used. I think he was worried about having to support the town and perhaps disappointing them if it didn’t work as well as we expected it to. Or maybe there was some other more nefarious reason, I’ll never know. But this experience showed me that it’s more than solving real problems for people that makes tech work - it’s all the humans involved in the process too.

Disillusioned, I left Betterway and went in-house at our biggest client - Biotest Laboratories. Biotest’s biggest website was (and still is) Testosterone Nation.. a delightfully ironic name for someone who would later come out as trans and work hard to remove testosterone from her system. At Biotest, I built e-commerce websites, content websites, online forums, live chat systems, and more - all from scratch in Java (Struts 1.3 baby!). I also built a small team of 10, my first real foray into leadership. It was fun tech, but I never really connected with it personally - another important element in delivering meaningful technology.

Building something that Mattered

In 2008 I got divorced and moved back to the DC region. I started attending Ruby on Rails meetups - a tech that fascinated me. With Rails, we could solve problems that would take us a month to write in Java in just a week, thanks to its convention-over-configuration approach. This enabled my team to focus on solving the problems that mattered for the business and our customers - it was a better abstraction. These meetups also were filled with people building startups, and at this time the DC startup scene was taking off, with big companies like LivingSocial just getting started.

Through one of these meetups, I met some guys who had a small business helping people sell things on eBay. One of them had built a surprising amount of tools in Visual Basic and Excel to automate this system, and they’d developed a vision to help companies deal with the sources of the items they wanted to move. These goods were mainly returned inventory and overstock goods, more broadly known as Reverse Logistics. I was excited about the problem and so I joined them. Together, in 2010 we founded Optoro, and I became CTO.

From just a handful of people at first, we rapidly grew the company to several hundred employees and tens of millions in revenue over the next 9 years. We used Rails and focused hard on solving the problems we knew existed. We pivoted our core solutions many times, but the technology enabled those pivots and explorations. Our team was focused on our mission, because we were solving a big problem that impacted the world’s sustainability - our technology kept things out of landfills, and got people what they wanted at better prices than retail. It was a whirlwind, with many long nights, passionate debates, and hard work, but it felt amazing.

Some of Optoro’s most important technology included mobile apps to streamline warehouse operations, and creating intelligent routing for secondary-market inventory across multiple online marketplaces to maximize revenue (I even secured a patent for an algorithm that could granularly juggle small product quantities in real-time across different sales channels). When we found product-market fit, our customers were thrilled to put our systems in place as it made their businesses work better, and their staff happier. We delivered real value with good technology and a team that was engaged and aligned. It worked!

Kinda missing the point

While my Optoro experience allowed me to finally bring all those elements together, an even more profound personal awakening forced me to reevaluate my priorities. In 2017, I came out as a trans woman. I’ve written a lot about the why and the how, but the impact on how I solved problems at scale took awhile for me to understand.

About 6 months after I came out, people started to treat me a little differently. They still said “hey dude!” and “what’s up man!”.. but also they started to require more evidence for my ideas. They started talking over me in meetings. They stopped taking me as seriously. Frustrated, I wondered what was happening. Had I changed? Well.. I had - but only in how people saw me. Inside I was the same person I’d always been - the same problem solver, the same creative thinker, the same person with the same drive and passion. But presentation matters.

I decided to move on, to find a place where I could start over as myself fully, and so in 2019 I took a new CTO role and joined Axios. At the time, Axios wanted to transform from a media company into a tech company, and I joined to enable that. I focused on quality, and on building an organization that could scale rapidly. I built mechanisms, career ladders, and focused on tooling. I failed to notice that this level of built-out was not what Axios needed at the time.

Axios was building a product that would later become AxiosHQ. At the time, the team was working out what the product needed to be - they hadn’t yet found product-market fit. While I felt that I was being scrappy, protecting journalists from nation-state security threats, or delivering tooling and systems to support the growth of the company - I wasn’t focused on helping the company work out what the product really needed to be. I learned another important factor for successful outcomes - the systems have to be scaled to meet the organization where it is at the time.

In 2020, the COVID-19 pandemic started, and Axios’s founders decided to dial back their investment in tech and double-down on their roots in media. I parted from the company, amicably, and found an opportunity at AWS.

Connecting the dots

At AWS, I started by leading IP Purchasing and Management. Several reorgs later, I took over as General Manager of the VPN services, which included the ClientVPN team who was working on micro-tunneling technology. When I joined this org, this project had gone through a tough technical review that questioned the feasibility of the team’s central approach. The product leadership was also in churn, so I dove deep to understand the customers’ true needs and determine how to move forward. Through diving deep, I discovered that, due the boom in remote work caused by the pandemic, customers were really looking for ways to enable their teams to access their sensitive corporate applications. They wanted a simple way to deliver Zero Trust remote access to critical applications. I brought these insights back to the team, and together we pivoted the project.

I worked hard to align on the problem and our proposed solution with other AWS service teams, security, and IT. They saw that our approach was what customers truly wanted, and so ultimately we launched AWS Verified Access (AVA). Because we solved the right customer problem, with the right technology, and with the right team backing it, AVA is now growing at scale.

After launching AVA, an opportunity came up to move to be the GM of AWS Firewall Manager and to work on a new exciting project that leverages GenAI. I saw an exciting opportunity to solve another big customer problem at scale with meaningfully-transformative technology, so I made the shift. I’m there now and we’re building something that I think will be important.

Looking ahead

In this new role I’m working with GenAI a lot. It’s another very shiny technology, and a lot of what the industry and media are saying about it smells a lot like the dot-com bubble. But the thing is, I’ve seen real value already in what we’re doing. It’s a higher level of abstraction that helps us focus on solving our customers’ problems instead of building the technology. It takes a different approach, but because we have an engaged team solving real customer problems with tools that truly can transform the experience, we have the opportunity to create something real and impactful. We’re focusing on learning as we go, on pivoting when it’s needed, on processes that work for us in the scale we’re at now, and it’s working.

GenAI is going to drive big changes. I’d be surprised if, in a few years, we’re not working side-by-side with AI in ways that are very similar to how we work with our coworkers. We definitely need to figure out the sustainability side - the power requirements today won’t enable us to scale this tech how we need to - but I’ve seen incredible progress already, and things like 1-bit LLMs give me hope.

But the thing is - we’re still solving problems for people. We still have to create the right systems at the right time, at the right scale, and with the right people involved. Even if it’s taken me 30 years to work that out - those are truths about progress.

As I think about the next 30 years, I’m excited to see what new technologies like GenAI can do, but I know the real value will come from applying them in the right way to solve actual human problems. Over these past few decades, I’ve learned that it’s not about the tech, and it’s not about the solutions you can come up with. What matters is really understanding the people, their needs, and their challenges. Then you can connect yourself and your team to those problems in meaningful ways. You can create the right structures that keep you connected to those problems. You can test and iterate and ultimately get to an excited “Yes, that made my day!” That’s what this is about.

PS, I’m writing a book about how to do this stuff.. I hope to get that done before too long. If you’re interested, let me know!

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