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. 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

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 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

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 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.

Happiness Engineer Automattic, apply for the job already.png

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.

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

  1. Hi Tish, I am very, very interested in applying to Automattic. I have been using WordPress for a very long time, like you, and I know it very well. I am surprised it took me this long to think about working for Automattic. They have a job open that’s absolutely perfect for me, Marketing Designer, using analytical and visual marketing skills together, but realizing this is my dream company and my dream job is paralyzing. I am obsessing right now over crafting my perfect resume and cover letter, gathering any of my designs (which I’ve done a poor job of keeping a portfolio of), and doing loads of research about Automattic and getting hired.

    My designs mostly consist of websites (some on .com others on .org) and a bunch of them were projects I worked on with companies which I can’t legally show as my own, and I don’t have a lot of other things to show. But I am confident I would be perfect for this job, I have the designer’s eye I always use putting together websites, and I am passionate about it. I could definitely use some help getting prepared and actually pushing myself to submit, because like you I am worried. Any advice?


  2. 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 🙂


  3. 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? 😛


  4. 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! 🙂

    Liked by 1 person

    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


  5. I am really happy reading this. I have applied with Automattic twice already and I got declined. I am still not losing hope! Since I still have that seed hope, I will water it with prayer and learning to be more qualified.

    Thank you so much! I was planning to reach out to you and ask advice(not sure if that is okay) most of my fears have been answered well here! Thank you so much!

    Liked by 1 person

    1. Thanks for sharing your story, Christina. I’m also interested in applying too (I first have to take care of some internet connection issues though). However, I don’t know if you have seen this or not, but I recently found this blog post entitled, “So You Want to Be a Happiness Engineer, Huh?” by Sandy McFadden to be very helpful for me. I am currently looking it over, because I don’t feel too comfortable about the tech aspects of it yet. I’ll see what happens!


  6. Hi Tish!

    This is an awesome story you are sharing, especially with so much detail.
    I applied to a customer marketing wrangler position last week and as you know, a week seems like forever!
    To be honest, I do get little discouraged after each day of waiting – I’m sure I’m not the only one haha.
    I just wanted to say thank you so much for sharing your story it’s very encouraging for someone in my shoes.
    Wish you all the best in Automattic!

    Liked by 1 person

  7. Thanks so much for sharing this, Tish! 😀 So much of what you wrote here and on your other posts is exactly what I’m going through too. I’m interested in applying for the company, but I haven’t felt as though I am quite ready yet…So I really appreciate you taking the time to share your thoughts and experiences; they’re very encouraging and inspiring! In particular, I really like how you went through the actual process of being hired and what that was like for you–it has helped me to have a better viewpoint of what to expect and therefore to be a little bit calmer about it as well! 🙂


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