How I Joined Automattic As A Happiness Engineer

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Automattic, the parent company of, Jetpack, WooCommerce (and a couple of other products) is one of the best fully remote company to work for and almost half of its workforce is technical support (i.e. Happiness Engineering).

I had some experience working with WordPress, running my own site both on and self-hosted setup and making a couple of sites for a handful of clients.

But it wasn’t enough because I was working as an Illustrator and Video Editor at a YouTube channel called MinuteEarth (sister channel of MinutePhysics).

When I first applied to Automattic in 2016, I got a rejection and the email basically asked me to try again later.

It was strange because I was hoping for an interview but that didn’t happen. It was disappointing but I wasn’t going to give up. Especially because I had already quit working at MinuteEarth and stopped all other freelance projects, only to focus on becoming a Support Engineer at Automattic.

I had no other option and I really wanted to make this happen so I started reading blogs by other Happiness Engineers, their experiences, books on providing quality support, volunteering in public forums and answering questions.

All of this helped me gain the experience I needed to do this job. I guess it also says how much I really want it because I was doing this all for free.

And then something exciting happened, I received an email from Automattic’s staff. They recognized my work and offered me a gift. I could choose between a business plan and a postcard.

I chose a postcard because a business plan will eventually expire but a postcard will always stay with me. Something that I can physically hold. Something that tells where it all started. A memory.

After receiving the postcard, I got the confidence to apply again and I did. This time, I wrote a long application and included a piece of art illustrating my efforts.

It worked! They got back to me in a week. I was interviewed over Slack. Questions were a mix of technical knowledge and customer support experience.

I passed and was offered a trial. Trial period is where you do the job just like other full time Happiness Engineers and write a self reflection every week or so.

My self-reflection included what I learned in the last week, what were the challenges I faced, what mistakes I did, how did I fix them, what was my approach, what was I looking forward to, and so on.

If everything went well, I’d be asked to continue my trial and go in the next week. Just like a game, if you pass, you go to the next stage.

After 4 weeks of trial, I was passed to MattChat, where we discuss compensation and start date with Matt (Matt no longer does this and it’s now done by HR).

Matt asked me my previous/current compensation and then made an offer. I accepted it. I didn’t negotiate it because it was enough for me and I really wanted to work at Automattic.

I have been working full time for Automattic for almost 3 years now. If you’re interested in working at Automattic, checkout

Update: I have made two roles switches in the past 3 years. In January 2019, I became a team lead for one of the four APAC Jetpack support teams. And in June 2020, I became a junior software engineer, joining a team that works on WooCommerce extensions.

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