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My Winding Path to Customer Support

This is part of the 2016 Support Driven writing challenge. Here’s the prompt: “History: Our history shapes us — what path led you to Support? Was it a planned career? Or did you happen upon it?”

I just passed my three year anniversary at Automattic, which is crazy to think about. I remember applying in August of 2013. I sent off an email that I thought would land in a blackhole never to be read or answered. I remember joking in the email that I had the perfect PJs for working at home. I remember doing my final chat with Matt and receiving the offer letter.

If you would have asked me throughout college or grad school if I ever thought I would be working remotely for a tech company, I would’ve given you an emphatic “No.”

Fitness was my life. Ever since 8th grade, I would spend my free time working out. I distinctly remember choking down protein shakes in high school (raw eggs, whole milk, and banana) while my friends were eating PopTarts or Eggo Waffles. I was a weird kid.

When I entered college, there was little question what I would study. I majored in Exercise Physiology for both my undergrad and grad degree. I got a job at the rec center on campus during my freshman year (funny story—I overslept for my initial training day). I ended up working at that same rec center for six years culminating in a graduate assistantship managing the personal training department.

When my now-wife and I graduated from grad school, we were looking for a place to move to. She was from Chicago and eager for seasons and snow. I had lived in Florida my entire life and was eager to go anywhere else. Colorado seemed as good a place as any so we packed up a U-Haul and started driving.

Now, the ultimate question: What do you do with a degree in Exercise Physiology? Well, you could do a lot of things. You could work in a lab, but that didn’t fit what I was looking for. I could work in Recreational Sports for a university, but those jobs are limited and hard to come by. At the time, there weren’t any openings in Colorado. Our fallback plan (my wife majored in exercise-related degrees as well) was to become personal trainers, and thanks to some connections we had through Florida, we had jobs before we even entered CO.

I’ll skip ahead a bit for you here, but the main thing you need to know is that personal training can be a challenging career (my most popular blog post ever is on that topic). After seven months, my wife and I were both looking for a way out. She found a job managing a corporate wellness center. I started looking at my options.

Outside of fitness, my main “passion” if you could call it that was technology. I had started a blog while in graduate school and began writing some freelance posts for places like Greatist.com. I was also managing a website called ConFITdent and wrangling a group of writers there. I found myself spending my free time managing website and dipping my toes into the world of WordPress. Unfortunately, at the time, I didn’t know Automattic even existed.

I went to work at Federated Media, now called Sovrn. They provide advertising tools for online publishers. The job wasn’t exactly what I was looking for, but it got me out of the gym and working for online publishers. It was a startup so I was able to live the startup life. I wore jeans and a t-shirt to work. Beer was delivered on Fridays. I played ping pong before mid-morning meetings. I worked on our deck overlooking the mountains.

The view from work wasn't bad.

The view from work wasn’t bad.

As part of my job at Federated Media, I would call online publishers and talk to them about placing ads on their website. I was compensated for overall traffic volume so my eyes were on the big fish. However, to stir up leads and activity, I would frequently find myself talking to smaller publishers and teaching them how to install the ads on their site (involved just dropping some code into a text widget). Most sites I interacted with ran on WordPress and since I knew how widgets worked, they would start asking me various questions about their site—How does mobile responsiveness work? How can I change this color to blue? I didn’t realize it at the time, but the support seed was planted.

Around nine months in, I started to tire of the sales gig. I didn’t enjoy cold emailing or calling businesses hoping for a hot lead. I wanted to do something different, but I wasn’t sure what. Looking back over the previous few years, the main thing that stuck was blogging. Throughout grad school and into my young professional career, I continued to use WordPress to build and maintain several different sites that I posted to regularly.

Eventually, I fired off a search: “WordPress jobs.”

Following link after link, I started to learn more about the WordPress ecosystem. I read about Matt. I read about Automattic. I read this interview about working at Automattic. The thought of working for a company with such strong values was appealing (working from home in your PJs was a huge plus). As I read the Happiness Engineer application, I found myself nodding my head. The support role seemed to be the perfect combination of my past:

  • Helping others (Combining elements of personal training with my work at Federated Media)
  • Constant learning (A value I hold very close to heart)
  • Excellent writing skills (Something I developed from freelance writing)
  • HTML/CSS knowledge (I was taking several courses at the time)

So, I applied. I still have the application email. The subject mentioned that I would be happier than a clam to work at Automattic, and fast forward three years, that has held true. Customer support wasn’t what I envisioned for my future, but it ended up being the ideal blend for my skill sets and passions.

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