How I became a Happiness Engineer at Automattic Part 1: Application Process

This is the story of how I applied to Automattic to become a Happiness Engineer. I was hired in June of 2015, so this post may not reflect the current hiring process for a Happiness Engineer. One of my favorite things about Automattic is that we are constantly testing new processes to see if there is a better way to do something, and that applies to hiring as well. So don’t be surprised if you have a different experience in the hiring process! 😉

Part 1: Application Process (this post)
Part 2: The Interview Process
Part 3: Paid Trial at Automattic

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Why I decided to apply to be a Happiness Engineer

Back in 2014, I attended my 3rd WordCamp Orange County. I ended up sitting next to an Automattician at lunch. Although we had a really short conversation, I walked away thinking about what a cool place Automattic must be to work at and how awesome Automatticians are (now 3 years later, I feel even stronger about that.)

At that time I was happily employed as an Interactive Project Manager at a marketing agency, overseeing all WordPress website development and marketing campaigns. I loved it. I loved my bosses, my coworkers, and the daily challenge of my job. Yet I still found myself browsing where I ended up looking at the Happiness Engineer job description. I fell in love with every aspect of the job description.

The idea of just helping customers all day long with WordPress,  just seemed too good to be true. I quickly came to the realization that while I loved the challenge of helping develop/design sites, helping others learn WordPress and troubleshooting issues made me the happiest. From that day on, I decided that somehow someway I was going to be a Happiness Engineer at Automattic. I wanted the challenge of working on the front lines of WordPress. With that, I knew I was gonna have to work towards it and develop my skills towards that end.

I read over the job description multiple times and honed in on the skills I personally thought I could develop further. One of the recommendations of applying for the position was being active in the forums. Something I had never done before.

Getting involved in the forums

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My initial goal was to try to participate more in the forums. I wish I could say that I was super active there. I wasn’t. If I could go back, I would’ve definitely done more in the forums. It’s a great experience and helps prepare you if you make it far in the interview process. My first problem was, while I thought I knew the answer to some of the questions, I didn’t know if it was the right answer. I doubted my ability to help others. Then to top it all off, I felt intimidated by the other volunteers who had been doing this for years (Note: this is not due to anything said/done on their part. They are nice extremely intelligent people they just did their job so well I didn’t know what I could contribute). I just felt like they had better answers and knew what they were doing, and I was just there like…. “whaaaat?”. So I mostly just followed some of the threads going on. If I could go back, I would’ve jumped in anyway.

If you haven’t gotten involved in any of the forums I would recommend:

  • Watching how Happiness Engineers reply and next time you see a similar question – you’ll know how to handle it.
  • Instead of trying to type the perfect answer – feel free to search for the answer on and use that in your answer.
  • If you volunteer in the forums, I recommend reading The Support Handbook.While technically it’s made for but a lot of the guidelines apply for as well.
  • Volunteers is a great resource if you plan on working in the forums here at
  • Learning how to troubleshoot and what to look for? I recommend this article on How to be a WordPress Detective

Why I didn’t Send my Resume in right away

Even though this was my dream job, I had a lot of personal concerns about applying. The main reason being that majority of my experience was with self-hosted and while I’ve worked with, I felt like I could know it better. I gave myself a lot of reasons to not apply just yet. That I hadn’t participated in the forums enough. Or my resume & cover letter wasn’t perfect enough after spending hours/days crafting them. Here is the thing, I actually do know WordPress very well – I’ve been helping other people use it for years.

I came to realize that the main theme in holding me back from applying was feeling like I was not “ready just yet”. What helped me get past that, was the realization that when something is outside of your comfort zone, you’ll never feel ready for it. Ever. So I was waiting on a feeling that was never going to come when what I really needed instead was to take action. I could either let the Happiness Engineer position stay my “dream job” by never taking action or I could take action and make it my new job.

I specifically wanted to share my thought process on what was holding me back because I am a Hispanic woman. I don’t have an extensive college education or even a college degree, but I had used WordPress and I was great at figuring out things by myself with the help of my dear friend Google. Before I applied to Automattic, I didn’t know anyone who applied for a dream job like this. I didn’t know what to expect or even if I would fit in or be welcomed. All of those thoughts scared me, so my default reaction became to say “I’m not ready just yet”. Which is exactly why I wanted to share my thoughts on this with you, it’s really important to me that you know Automattic is a place you’ll be welcomed. If you’re telling yourself you’re not ready yet, just remember you may never feel completely ready. Do the best you can if you don’t know WordPress just yet by taking some time to learn it, and just take the shot and join us already!

If you’re a woman reading this… I’m going to say something I wish someone had told me back when I was struggling with whether or not I should apply. Whatever your dream job is (even if it’s not at Automattic or as a Happiness Engineer), just apply for it. It’s okay if you didn’t hit every single checkbox of the qualifications. Apply before you think you’re ready.  Studies show that a large portion of women won’t apply for a job unless they meet 100% of the qualifications. This is something that held me back from applying much sooner, I really regret that and wish I would’ve applied sooner. So if you’re still reading this, give it a shot!

It’s perfectly okay if you don’t get the dream job on your first try, just keep trying and jumping outside your comfort zone. Each time it’ll get easier and easier. Failure isn’t when you try something and don’t get it, a failure is when you don’t even try. If it doesn’t work the first time, try again, then again, and again. If you want something bad enough, are willing to work hard, and don’t give up- you can do anything you put your mind to, it’s just a matter of time. I personally would rather be turned down for not being ready just yet and reapplying when I was than be holding myself back when I have been ready for a while.

20 seconds of insane courage

So after coming to the realization that I was ready to take this shot, I spent hours crafting my cover letter and resume. Automattic is not just some random company I found while searching Craigslist’s Job Postings. Sending a generic cover letter and resume was not an option for me. I had to go the extra mile.

I’ve always been a firm believer of having a personal brand- which is why I have “business” accounts on several social networks where I only share work-related articles and thoughts. This has always been something I recommend to anyone looking for a job.

I also took some extra steps by graphically designing my resume. While I have no idea if that made any difference when Automattic took a look at those, I’ve found in previous positions, it’s given me an edge and helped me to stand out. It’s also become a hobby I’m a little obsessed with, I even have a Pinterest board on Graphically Designed Resumes to prove it haha! 🙂 If you’re not a designer, don’t fret- there are graphic designed resume templates you can find on Etsy. I recommend checking those out.

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If you’ve visited the Happiness Engineer job page a few times you’ll notice in the sidebar a little message encouraging you to just apply already, this was the extra push I needed to finally apply. After crafting my resume and having several people proof it, I was suddenly hit with a “I’m not ready yet. Why should I send it, what if I don’t hear back?” mentality/butterflies. So I convinced myself, I didn’t need a lot of courage… all I needed was 20 seconds of courage. So I mustered up 20 seconds of insane courage and I hit send. I applied to Automattic.

Then came one of the most difficult parts of all… the waiting. I waited. I waited. Then I waited some more. Eventually, I even sent a follow-up email. Thing is that while I waited, I continued to develop my skills to someday becoming a Happiness Engineer. I even read this awesome series of posts on A Day in the life of an Automattician, which I always find super inspiring and shows the diversity and culture of Automattic.

Then one day I opened up my email box and there it was, an email asking if I was still interested in the Happiness Engineer position (YES!) and thus began the interview process.

So basically the moral of the story is If you have any doubts about applying, give yourself a deadline and just hit send. You’ll probably end up surprising yourself.

What to know what happened after I applied? Read Part 2: The Interview Process.

how i got a job at a remote work company