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

The story of how I applied to Automattic to become a Happiness Engineer and got hired.

This is the story of how I applied to Automattic to become a Happiness Engineer. This post is about my own experience when I applied to become a Happiness Engineer at Automattic and are not necessarily current hiring policies within Automattic.

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

How I became a Happiness Engineer at Automattic.png

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.

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

Happiness Engineer Support Forums.png

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 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 anyways.

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.

I also found a great resource called The Support Handbook it’s technically for but a lot of the guidelines apply for I happened to stumble across this when I was already in the hiring process with Automattic, but I highly recommend checking it out.

20 seconds of insane courage

Even though this was my dream job, I had a lot of personal concerns about applying. The main 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” or my skills weren’t “good enough just yet”. What helped me get past that, was the realization that you miss 100% of the shots you don’t take. Take the shot. 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. Now looking back, my only real regret is that I didn’t apply sooner.

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.

Happiness Engineer Automattic, apply for the job already.png

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.  Also, 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. 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.

9 thoughts on “How I became a Happiness Engineer at Automattic Part 1: Application Process

  1. Hi Tish,

    Great post, thanks for taking the time to share your experience here. I stumbled upon your blog in my quest of knowing more about Automattic and hopefully even getting to work with them. Now, my situation is a lot similar like what yours was before you applied. I wanted to “shoot you a message” but I don’t know where to 😀 . Anyway, I’ll be going through the rest of your posts as I think they will be very helpful. Thank you again 🙂


  2. Since a little over a year ago I’ve been thinking about applying for a position as a Theme Wrangler, but the thing is… I work at a youth hostel, I cook meals, help people at the reception and do some administration; nothing fancy like dabbling with code or design or anything remotely related to WordPress.

    But I’ve learned a lot. I’ve even build a few themes that I’m a little proud of:
    (Though the first ones are terrible!) 😉

    I don’t know if I have what it takes to ever get hired by Automattic.

    But I will continue to learn: I will finish a few more courses at CodeSchool; make one or two more free themes; and do a lot of theme reviews at

    And then I will apply! Is there any advice you can give me? 😛


  3. OMG! Just reading your experience felt like I’m reading my own feelings written by someone else who overcame that self doubt and nervousness. 🙂
    It’s been almost 2yrs now since I thought of applying to Automattic. Just like you mentioned, working in Automattic is my dream job, a place so cool and constantly filled with new adventures to explore with your teammates. And today i saw that blue box on the right side of the Happiness Engineer page saying
    “Hey there!
    We couldn’t help but notice that you’ve visited this page a few times. It looks like you’re really thinking about working here, huh?

    Give it a shot and apply already!”

    Which almost gave me a heart attack out of excitement! hehe

    I have been working as web developer since 2011 especially in WordPress and I’m amazed how supportive our community is. I have raised so many tickets for help but never really got the courage to help someone else, thinking that maybe my answer will not be good enough, but this time I think I should click that send button with an attractive resume like yours which might help me stand out a bit from all the other applicants. 🙂

    Thanks for sharing such a wonderful experience with us and motivating us to go and apply now! 🙂


    1. Hi Tsetan!! :wave:

      Thanks so much for reaching out! 🙂

      Really happy to hear that the blog post was able to help! I know for me, it was so easy to think of my dream job as a “maybe someday” kinda thing, instead of “I’m going to apply today, or this week”. I really hope you do apply! Let me know how it goes! 😉
      Wishing you all the best, -Tish


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