My Journey to Automattic

I’ve spent a lot of my adult life playing around with websites. I mostly have my partner to thank for that—she’s been building increasingly complex websites since we were teens, and, around 2010, she introduced me to WordPress.

I’ve always been a writer, but my blogs were hard to keep updated, as I relied only on HTML for a long, long time. As a result, I had her help me build a WordPress blog or two over the years. However, there came a point where asking her for a hand became a bit troublesome—so I started tinkering with the `/wp-admin/` section myself. She thought it was adorable seeing me struggle through simple CSS while she was hand-coding themes from across the room.

I tried my best not to lean on her expertise, though—to me, the intricacies of working on a self-hosted WordPress installation made me feel like a detective, and using the simplest command line inputs made me feel like a hacker.

It wasn’t until I went back to school to pursue a degree in journalism that I got to put some of my WordPress knowledge into action. All journalism students were asked to create an online portfolio—and the platform of choice was When I became an editor for the paper, staff writers and photographers caught wind that I knew a thing or two about WordPress, so they leaned on me a bit to help them resolve their issues.

There was an issue, though—I did know a thing or two about WordPress, but I oftentimes didn’t know how to do what they wanted! I spent a lot of time researching issues with staffers side-by-side and helping them modify their portfolios to suit their needs—which was, hopefully, to get hired by a publication.

I’m a big fan of puzzles—always have been—and unraveling the goals of my peers and trying to put them into something tangible was quite exhilarating. And the more people I helped, the more I learned, and the more I loved it.

I loved helping people build their WordPress sites so much that, instead of looking for a gig as a reporter during my last semester, my instincts were telling me to go for WordPress instead.

That was my first time hearing about Automattic—I didn’t know that WordPress was more than WordPress. I knew it was open source, but I didn’t think about the people who built and maintained it because, after all these years, my partner and I had just built websites by the seat of our pants. It was almost like WordPress had always been there, like an ancient relic.

The role of a Happiness Engineer seemed to be exactly what I’d been doing at school—helping folks build better websites. But as I looked into the company a bit more, I was astonished at how much its vision and creed resonated with me. I’d spent years in customer service, but with the pandemic showing no signs of slowing in early 2021, I was also excited at the prospect of working at a distributed company.

When I submitted my application, I was a nervous wreck. One of my old professors had said that anxiety can be just a sign that something’s really important to you—and that’s what this was.

It wasn’t much longer afterward that someone from the Happiness Engineer hiring team reached out to me and asked me to build a website. This caught me off guard—I’d never interviewed for a job where my first task was to complete an assignment. But it made sense—what better option was there to size me up and ensure that I could (1) follow directions and (2) build a website?

My partner kept looking over my shoulder as I spent the next few hours adjusting theme colors and selecting some of the perfect images. I ran into some trouble answering some of the questions, but all in all, I was satisfied with what I had accomplished. 

When it came time to send the site for review, I asked her to do me a favor and help me click the `Submit` button—for good luck. The good luck must have worked because I had an interview on deck shortly thereafter! But it wasn’t just any interview—it was a text-based interview over Slack.

It makes me feel a bit old when I reflect on my reaction, which was basically: “What do you mean an interview over Slack? That sounds weird.” 

However, in a distributed company, synchronous conversations can be few and far between, and, as a Happiness Engineer, I’d be spending all of my time typing with members of the greater WordPress community. Once again, this process just made sense, even if it was different from any interview process I’d done before.

I didn’t know it at the time, but this interview would be my first taste of something very important in the creed: 

“I will communicate as much as possible because it’s the oxygen of a distributed company.”

The person interviewing me asked some difficult questions about some of the decisions I made on my site—decisions that I had wrestled with myself before and after submitting it for review. I felt scared, thinking that I got something wrong during a project that was so vitally important.

I’m not sure why, but at that moment, I leaned into that vulnerability. I was open and honest in a way that I probably wouldn’t have been in a more “traditional” interview setting—where it would have been expected for me to boast with a false sense of bravado about how infallible I am. 

Instead of inflating my ego, I admitted that I didn’t have all of the answers, and I noted that some of the information I included could have been much better. I didn’t know what to expect after we wrapped up—I thought my forthrightness may have cost me such a great opportunity.

When Automattic invited me to become a trial Happiness Engineer, I was in a bit of disbelief. I don’t know how I went from helping my college classmates with their portfolios to spending three weeks learning the ropes at, but there I was—wide-eyed and anxious as hell.

The trial was my first true taste of what being a Happiness Engineer was. I’d read quite a bit about the role—from blogs to Glassdoor reviews to official documentation—but, as a kinetic learner, it didn’t hit quite the same as answering my first ticket or entering my first live chat with another real human being. It put into perspective exactly how much I didn’t know.

Before becoming a Happiness Engineer, I thought that there was a finite amount of things to know about WordPress—and, I guess, if one were to quantify all of the things that a blogger or merchant can do with WordPress, then there’s probably some astronomically high number of “things” that one can know in order to become the WordPress Master. 

Sure, I was familiar with WordPress—but what about domains, plugins, and themes? What about Full Site Editing? There was seemingly no limit to the number of topics that fell under the umbrella of Happiness Engineer—and the potential number of things to know skyrocketed as I turned my focus toward WooCommerce.

WooCommerce is a part of the WordPress ecosystem that I was completely unfamiliar with, and its individual components—like taxes, payment processing, APIs, etc.—I knew even less of. However, there was a slow ramp-up in my learning. The vast chaos of the WooCommerce universe (or Wooniverse, if you will) was broken up into smaller, more manageable chunks. I had hands-on assignments to put complex details about shipping configurations or subscriptions into action to test my mettle and ensure that I understood the basics of what I had to support.

When I hit a wall, I had an army of people eager to assist me—I had a person who oversaw my onboarding, but I was also assigned to a team of folks in my part of the world—on top of the 100 or so Happiness Engineers on other teams spread across the globe—who had a variety of backgrounds and skillsets to lean on.

I had moments where I felt like I was expected to know everything, but my onboarder, my team lead, and my peers all echoed the same sentiment: that isn’t the expectation of anyone at Automattic. Instead, there are repositories of detailed information about all the products and services we support. There are places to pose questions and ask for advice. There are channels focused entirely on anything and everything that I may have questions about—and, if not, then a new one can be created.

The chaos and the unfathomable amount of knowledge at my fingertips were unlike anything I had ever experienced before. However, there wasn’t a moment during this time that I didn’t feel as though I was lost. Instead, I felt like I had all of the tools I needed at my disposal, and there was no shortage of resources I could use to help me to determine which tool was best for the job.

I went into the process of becoming a Happiness Engineer at Automattic not really knowing what I was getting myself into. The role was more than just helping folks build better websites—it was about connecting with the larger WordPress community to solve problems. It was about communicating clearly so that the person on the other end of the internet knew exactly what I meant. It was about trusting myself and my own intuition to help those who needed it. It was about taking things one step at a time, and not being afraid of not knowing the answer.

Interested in becoming a Happiness Engineer at Automattic? Visit the Work with Us page to learn more about how you can apply!

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