I write to you from a small but stylish hotel room in New York. I’m here to spend a week in a Product Management course at General Assembly to prepare for my new role as an Associate Product Manager at Trello. Before this opportunity was announced, if you had asked me to write down exactly what I wanted to do next, it basically would have been this job description.
I haven’t always been this happy in my career. Just two years ago, I was pretty miserable. I was in a professional setting that was not a good environment for me, and I was just a few weeks away from being unemployed. I felt hopeless, without a chance of ever finding a better situation.
So I how did I go from despondent to dream job? Well, to be honest, it involved a lot of luck. But maybe there’s something in the story that can be of use to someone else, and with that hope in mind, here’s how it happened.
The first thing you need to understand is that I love Trello, and have loved it ever since I was first introduced to it, nearly 5 years ago. At my old job, people used to call me the “Trello Queen”, and anyone with a question about Trello would come to me for help. I was constantly trying to find more ways that we could use Trello, or how we could make our existing Trello boards even more efficient.
One day, in the spring of 2015, I received an email from Ben McCormack, the head of Trello’s support team at that time. He and another team member in the Atlanta area were looking for opportunities to interview customers to learn more about their pain points and how they were using Trello. They’d looked up Business Class customers in the area, which is how they found my company, and then looked up the most active user in each of those teams, which is how they found me.
It was as if I’d gotten an email from the Beatles. I was so excited. I distinctly remember telling them that I’d brought my blue pen to the meeting because Trello is blue. They sent me a Trello t-shirt later, and it quickly became a prized possession. Although I now have multiple Trello shirts, that one being perhaps the least interesting, I still can’t bring myself to part with it.
More than just a T-shirt, however, they’d left me with something more significant: the realization that I could work for Trello. I’d had no idea that Trello had remote employees before then, and it had never occurred to me that my penchant for problem solving (and my experience answering questions about Trello) could actually lead me to a job.
Within a few weeks, I sent in my resume and what was practically a love letter, pleading for a chance to join the support team. Despite my lack of any customer service experience, I promised to learn quickly and work hard, like a child begging for a puppy: “I promise I’ll take care of it!”
My sincere passion for Trello must have caught someone’s attention, because I had a call with the VP of People that August. It went well, but there were no openings on the support team at that time. I would have to wait. I was optimistic at first, but as the months passed, and my existing work situation became increasingly problematic, I began to give up on my dream of working for Trello.
Some months later, in February of 2016, the company I was working for downsized, and my job was cut. Although I was disappointed that I didn’t get to leave on my own terms, in many ways, it was freeing. I felt like a huge weight was lifted from my shoulders, and I was happier than I’d been in a long time. But then it was replaced with a bigger weight called “finding a job”.
I didn’t know what to do. Although I’d been with my previous company for nearly six years, I didn’t feel like I’d gained any skills or experience there that would be valuable to another employer, and I wasn’t even sure what I kind of work I was interested in.
I immediately checked Trello’s job openings again, still hoping I might work there someday. I saw an opening for a tester, and I decided to give it a shot. It didn’t work out—they needed someone with actual QA experience—but they turned me down in the nicest way possible, promising to keep me in mind if something came up that was a better fit. I assumed they were just being nice, though I appreciated the gesture, and decided it was time to broaden my search.
Over the past several months, I’d become increasingly interested in UX, and, desperate for direction, I decided to take advantage of that spark of interest, signing up for a part-time, ten-week course on UX Design at General Assembly. It came together very quickly, which felt like a good omen—the first class was the evening of my last day at my job (which, weirdly, wasn’t the day that I was let go).
At first, I would spend the days sending out job applications, but as the course progressed, I decided to make it my focus instead, so that I could put together a portfolio and send out more targeted job applications with a better chance of success when the course was over. During the days, I read articles, worked on my final project (which you can see here), and generally tried to figure out what I should be doing with my life.
One day, I saw that General Assembly was hosting an event called “Born for This: How to Find the Work You Were Meant to Do”. That seemed directly relevant to my situation, so I went. As it turned out, it was a book tour. I liked the talk, bought the book, and read through it quickly, determined to begin applying its principles as soon as possible.
As it turned out, I didn’t need to do much—the work I was meant to do found me just three days later. That morning, I was eating a leisurely breakfast and checking email on my phone when I saw an email from Ben McCormack titled “Working at Trello”. I nearly choked on my biscuit—there was an opening on the support team, and he wanted to know if I was still interested!
By the end of the week, I had a job offer, and a week after that, I was on my way to New York for my first day at Trello. For nearly two years now, I’ve had the privilege of working for my dream job.
(If you’re following the timeline astutely, you may have noticed that that neither the UX course nor the book could have actually played a part in me getting my job at Trello, as Ben wouldn’t have known about either when he reached out to me. Still, to me, they feel inextricably linked. I can’t help but believe that these steps toward finding my true path did indeed help me to find it, if only by giving me the courage to actually walk that path when it became clear.)
After a few months in support, I began to take an interest in making a bigger impact at Trello, giving users a better experience at scale, rather than helping them one at a time. I started bringing the trends I saw to the Product team and advocating for certain changes, and the first time one of my suggestions was shipped was honestly one of the proudest moments of my career.
Soon, I felt like answering user’s questions was something I was doing as a tradeoff, the dues I paid so that I could do what I really loved: finding trends in our users’ comments and working with the Product team to solve bigger problems. When an internal opening was announced for an Associate Product Manager, I knew I had to apply. A month and a half and four rounds of interviews later, I was offered the job, and I couldn’t be more thrilled about this new opportunity.
—
Have you found your dream job, or are you still looking? What have you found most helpful in gaining fulfilment from your work?
Caity Thinks 