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Looking back on four years at Automattic

A pattern made up from Automattic's logo.

It was a little over four years ago to this day that I signed my offer at Automattic and handed in my notice at Shopify. Little did I know, I was heading for one of the biggest adventures of my life. It started even before my first day. My plan was to take a week off in between jobs but that changed when my new manager reached out to me, in the middle of a Canadian winter, and asked if I would like to join the team for their meetup in sunny San Diego — it was an immediate yes! From that first moment I met my colleagues in a foreign city until now, I have had so many valuable experiences that I am grateful for and will carry them with me for the rest of my life.

Starting with travel, I feel lucky that I got to visit so many different cities that I would have never gone to on my own. I enjoyed every destination for its own reason but my absolute favourite was Scottsdale, Arizona. We got to stay at an amazing resort where I fell in love with the desert landscape and enjoyed seeing all the wildlife. I also can’t forget going to Detroit for a Design meetup organized by John Maeda and meeting local business owners. The people were so warm and had the strongest sense of community I have ever felt anywhere I’ve been before.

Desert scenes in Scottsdale, Arizona

Once a year, the travel would include a trip to the company’s grand meetup where the whole company would descend on a single location. I will never forget the feeling of roaming around the hotels late at night and randomly stumbling across all the different cultures and activities people were participating in. There were people playing video games, making art, dancing, roleplaying boardgames, socializing, having drinks, and practicing music for the big show they would put on, on the last day — which was always a treat! I spent a lot of time watching the bands practicing and often felt like I was getting my own world class personal show.

Silent disco at the GM

Another thing that will stick with me for a long time are all the connections I made with people. I found that there’s something about spending a week in close contact with your fellow colleagues where you form bonds you rarely find in the physical workplace. I feel lucky that I got to meet and work with such talented folks from all over the world which is a testament for distributed teams in of itself but also truly believe that I am a better person for it. Meeting people from different countries, backgrounds, and walks of life exposed me to new ideas and made me a more open minded person.

Lastly, something I will be taking with me everywhere I go is the professional experience I gained while working at Automattic. This was the first job I worked at a fully distributed company and can’t think of a better place to learn how to “remote” than from one of the worlds first remote companies. Working in this environment, I got a lot of practice writing and feel like I became a better communicator as a result. I also dedicated a lot of my time to my craft and feel like I came into my own as a designer — refining my approach and practicing my quantitative and qualitative research methods.

My next journey takes me to B12, another site building company focused on building tools for small businesses using artificial intelligence and automation. I am excited to start this new chapter in my life bringing over the experiences I have gathered through the years.


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