From a Broadway Musical to 55 Broadway

Published by Caity Cogdell on Dec 18, 2018 • #devstory

This is a part of a series of #DevStory posts that chronicle the personal and professional development of Trellists. The premise is simple: As a form of peer mentoring, dev stories are a showcase of the diverse paths Trello employees have taken to becoming colleagues, and lessons they’ve learned along the way. We hope that these posts provide hope, support, encouragement, and advice to others through the sharing of our own experiences.


When I was 11 or 12, my grandparents took me to see a touring production of the musical Cats in my hometown of Savannah, GA. As much as I was embarrassed to admit it once I got to high school, I absolutely loved it, and spent the next few years completely obsessed.

Clearly, the only way I could adequately express my adoration for this musical was to create a fan site on Geocities. This was, after all, the ’90s. There was just one problem: I didn’t know how to build a website.

Fortunately, the same grandparents who took me to see Cats were also happy to take me to Barnes & Noble and buy me a book on HTML. That summer, I launched my website, and I was pretty pleased with myself.

10 Years Later

During high school, I was more interested in participating in theatre than making fan sites about it, and I soon learned that it wasn’t cool to like Cats. So I stopped working on my website, and I didn’t touch HTML for years.

Once I got to college, I became interested in joining the student programming board. Most people who joined the SPB were much cooler than me but apparently didn’t know HTML, because they were very pleased to find out that I did. They made me the webmaster, a role that mostly consisted of updating the website to show what movies were going to be playing each month at the student center. Everything was done using Dreamweaver and tables, so I can’t claim any particular greatness.

When I graduated from college, I’d never had a job other than seasonal retail and theatre camps. I hadn’t even done an internship, because I’d picked a major that I didn’t actually have any interest in. This also meant that I had a degree that I had no interest in, and no idea what I was going to do with my life. I did, however, know basic HTML (not even CSS at that point!).

My first job out of college was for an ill-fated startup that involved building out online advertising pages for car dealerships. Our office doubled as a pinball warehouse, which was a considerably more successful business. I was told that they hired me because I knew HTML—which, if you’ll recall, was entirely because of Cats.

The company didn’t last a year. My lease, however, was still going strong, so I started working as a tutor to pay the bills. Meanwhile I was still trying to figure out what I should be doing.

The Next Step

While I had been working as a tutor, two of my coworkers from the doomed startup had used their new free time to start their own SEO company. About a year later, when they were ready to hire their first full-time employee, they called me up, and I turned them down.

But, the truth was, working for a tutoring company wasn’t exactly lucrative, and the hours were terrible. So, I called them back and accepted the offer.

Suffice it to say it wasn’t a great fit. I used to cry every day on the drive home. I wanted to quit, but apparently not as much as I wanted to not have to look for another job, because I worked there for nearly 6 years.

To be fair, it wasn’t all bad. Things got much better for me once they hired another woman, and while there were definitely some bad times, there were good times as well. I love to learn, and there was plenty to learn there. I got to do a little bit of everything: project management, content marketing, design, development, management, SEO, client relations—you name it, there’s a good chance I did it.

Hello, Trello

There’s a lot to keep track of at an agency, and we were struggling to stay organized. Eventually, one of our clients told us about Trello, and we made the switch. I quickly became obsessed. I designed and redesigned Trello workflows for us, wrote up documentation and training on Trello best practices, and became the go-to person for any Trello-related questions, earning the nickname “The Trello queen.”

So, as you can imagine, I was pretty darned excited when in the spring of 2015 I got an email from a real live Trello employee.

Ben McCormack, the manager of Trello’s support team at that time, was interested in interviewing some of Trello’s customers. He’d looked up teams with Trello Business Class accounts here in Atlanta, where he also lived, and found the company that I was working for. Then, he looked up the most active user in each of those teams, and found me.

Ben came to my office with another member of the Trello support team, and by the time our meeting was over, I knew I wanted to be doing what they were doing. Even though I had no experience in customer support, and the support team wasn’t currently hiring, I sent in my resume, along with what was basically a love letter to Trello. In response, I received a lot of encouragement, but no job offer yet—after all, they weren’t hiring.

Achievement Unlocked

I ended up applying to Trello twice. Several months after that first attempt, in February of 2016, the company I was working for cut my department, and I found myself unemployed. I saw an opening for a Tester at Trello. I figured it was worth a shot, and applied again. Trello’s people team wisely decided to hire someone with actual QA experience instead, but they assured me that they liked me and would keep me in mind for the future.

I figured they were just being nice, so I put all my focus in a UX design course I was taking and decided to put aside my dream of working at Trello. Fortunately, I was totally wrong, and I got an email from Ben McCormack a couple of months later asking if I was still interested in the support specialist role—–there was finally an opening!

Two weeks later, I walked up to 55 Broadway in lower Manhattan, convinced that I would get there and there would have been a big misunderstanding. Maybe that wasn’t really Trello’s office. Maybe I hadn’t been hired at all!

But it was Trello’s office, they really had hired me, and it was an awesome first week.

A Bigger Fishbowl

I had a great first year at Trello. I loved being on the support team. My teammates were fantastic, and I felt like I was actually pretty good at my job.

There was only one problem: I got comfortable.

I definitely do not subscribe to the belief that everyone should strive to be uncomfortable all the time. But, in my case, I knew that comfort would eventually lead to boredom. I needed some more room to grow.

Like at many points of my career, I had some help realizing my next step. A member of Trello’s product team invited me to participate in a design sprint, and I can’t express how excited I was to join in. I’d already been thinking about trying to move into product, and that week only reinforced that direction. When an associate product manager role was announced, I eagerly applied, and I was overjoyed when I got the role (although I was also a bit sad to leave the awesome support team).

Moving from a role where I felt like a strong contributor to one where I was starting from zero was definitely challenging, but now that I’ve been in it for a while, it feels good to be growing again.


When I was a teenager, I was embarrassed by how much I’d loved Cats in middle school, but without that motivation, I don’t know if I would have decided to learn HTML. I can trace my entire career back to that show.

And when things at my previous company went sour, I felt ashamed for having stayed there so long, instead of standing up for myself and finding a better situation. But if I hadn’t been working there when Ben decided to do his customer interviews, I may have never applied to work at Trello.

So if I can leave you with any closing thoughts, it would be to not spend too much time regretting seemingly “wasted” time in the past, because those experiences bring their own lessons and opportunities, even if we might have preferred to gain those some other way. Better to focus on what we can change: Our future.