A Tale on becoming an Happiness Engineer at Automattic P1

by Lรฆ
Road to Happiness Engineer

I have decided to explain the steps taken when applying for Happiness Engineer at Automattic.

For context, some months ago I set some goals for myself, as I found a couple of things I wanted to do differently.

Things about myself that became clearer:

  • Freedom and autonomy of my work, tasks and ultimately, my life are essential;
  • I need to work on something that I know is helping people;
  • Teaching and explaining techie things to non-techie people is where I thrive;
  • I need to see a sense of purpose and the passion.

A couple of options existed that filled these requirements. One of them would be to work remotely for a company that has a product or service that is actually helping people navigate technology. One of the companies that appeared and matched was Automattic: the company that powers WordPress.com, WooCommerce, JetPack and many other products.

Since I spent the last months working on WP friends’ projects I got to know a little more of WordPress and WooCommerce. I was amazed by the platform and its capabilities!

After a lot of time, and seeing this message dozens of times:

happiness engineer recruitment invite

.. I finally decided to apply. In the worst case scenario, I would re-apply 6 months later. Between this and not applying at all, it was actually a no-brainer.

Automattic has its own recruitment process. It is made so that you will only progress if you really want to. Be warned: it will make you sweat and, as you start thinking about it, will crawl into your nights and dreams as you wait for the next phase to arrive.

Happiness Engineer at Automattic Recruiting Steps

As I write this, I have actually no idea how far I will get into the process. However, I will give an overview of the general process so far and the perception I have of the next steps:


December 20

Finally Applied!

Finally Applied!

Automattic asks for an email application where you can / should answer some questions specified in the job posting. It seems rather simple. It took me some time to gather the information I needed and write a text that would be simple and included everything I wanted to say. To be honest, as the process went forward and I prepared myself for the next steps, I already found a couple of things I would change in that initial text ๐Ÿ™‚

December 26

Small Project

If you are selected, you will be sent instructions to complete a small project. There is no time limit to delivery and all I can say is: for me, it was really fun! I did learn a bit in the process. I believe they manage to understand some things with this project: if you really want to work there, if you know WordPress, if you are capable of making decisions and being autonomous in your work. I do advise anyone that does this, to take high-level notes on the steps to complete the project – I did and it was really useful later on.

December 28

Project Delivered

Project Delivered!

December 30

Zen Tech Work

Interview Scheduled

I was invited to a Slack Interview on the 9th January. Automattic provides support mostly via written forms (forums, live chat or email) โ€“ so the recruitment happens in writing. I really like this way โ€“ as an Introvert, it is not always easy to express what I want to say in video interviews and via Slack becomes more natural. I started to prepare for this interview:

  • I read all blog posts I could find on other experiences of the recruiting process
  • I dove and volunteered in the forums to understand the subjects and ways to respond them
  • I read Delivering Happiness by Tony Hsieh
  • I watched all YouTube videos by Automatticians I could find

January 9

a cup with begin written on it

1st Slack Interview

The interview was… well: strangely nice and comfortable!

An hour before I disconnected all my communication with the world, made a Mu Tea for myself and just gave myself this time to relax. As the hour came, so did Karen’s first ping, and so it started!

Although I had read statements of previous applicants saying how nice it was I had to go through the process to feel it. Maybe the fact that I use Slack on a daily basis helped but it felt really familiar and as a friendly chat instead of an interview ๐Ÿ™‚

After approximately an hour of chatting I was informed that I would receive an email with follow up questions.

And that was it..! A really great experience so far!

January 11

person sitting in pile of books

Delivered Follow Up Questions

I set the next afternoons and evenings aside to focus on this deliverable and started to contribute to WordPress forums to understand the wording, the types of questions, etc.. I read a LOT of support documents and research around numerous subjects.

At the end of the 11th January, after triple checking all of them and feeling overall satisfied (and kind of proud) of my work, I sent it in.

And I prepared myself for another wait. I knew, from what I had read in countless posts, I would either receive an invite to another interview (for the trial?) or a rejection email…

January 15

bear facepalm meme

Feedback or.. Major Facepalm

I received an e-mail from my recruiter. My heart started racing as I was expecting a yes or no kind of feedback.

Instead, I read “I am not seeing the replies to the sample questions.(…)” explaining that the file I had sent was the wrong one!

I cannot express the number of emotions I felt at that moment. My instinct was to make it right as soon as possible! So I answered right back with the correct file and a HUGE apology.

Part of me though: “You had one job!“. The other tried to feel hopeful: “this will probably not be a reason for rejection”… or will it?”

January 16

2nd Interview Scheduled

2nd Interview Scheduled

Well.. I got an e-mail for a second chat/interview.

I was SO SO SO happy, although part of me was warning me “be calm, this means nothing yet” the other part was actually jumping and dancing and feeling SO thankful to life and everything else.

January 23

north tattoo in arm

2nd Interview

I felt I could allow myself to read a bit more about the company (managing inner expectations and all) and got the “A Year Without Pants: WordPress.com and the Future of Work” by Scott Berkun. What can I say? If I wasn’t hooked before, now there was no coming back!

I set some time apart for this interview, as I wanted to be calm and fully focused.

As with the first interview, I disconnected all devices and distractions an hour before, made a tea, and sat at the computer reviewing the answers I had sent last time. Once again, it was really nice and all questions were posed as they would be in a conversation over coffee, which drives sincere answers!

At the end – I was invited to the next step: the trial period!! YAY!!

Thank you so much for reading all this. The Second Part of this post is here – check out how my Trial process went.

Feel free to ask questions or leave comments below ๐Ÿ™‚




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Ann Bingle May 23, 2018 - 02:34

Thanks for sharing your journey on this really wonderful blog of yours. Well, I already bookmarked it so I can easily follow your blog posts.

I am also applying for the Happiness Engineer position. Iโ€™m now at the waiting end on whether I will get a 2nd interview (for trial) or I will get rejected. The waiting is really agonizing. I sent my answers to the follow-up questions and some sample questions last Sunday(20th May 2018)morning (9 AM) and now it is Wednesday (23rd May 2018). Itโ€™s okay though as I got no other option but to wait. I understand how you felt last time when.

Are you on trial now? How is it so far?

Goodluck to you:)


Lรฆ May 24, 2018 - 07:23

Hi Ann ๐Ÿ™‚ every waiting time is tough, but hnag on there!! Thanks for visiting my blog – if you have any questions, do make them ๐Ÿ™‚ The trial went well, am working on a post to talk about it. I am already a full time Happiness Engineer at Automattic – and loving it!!! Wish you the best luck – and keep me posted!

Sophia June 6, 2018 - 15:53


Thanks for sharing your personal journey, insights and lessons learned! ๐Ÿ˜€ It was a very informative and encouraging story. I was also wondering if the projects you were assigned were asking you to specifically use html or css in great detail? And although you said the interviews were friendly and conversational, would you say they also became somewhat technical at some point too?

PS: Congratulations on becoming a Happiness Engineer! ๐Ÿ™‚

Lรฆ June 6, 2018 - 22:16

Hi there Sophia ๐Ÿ™‚ Thanks for stopping by ๐Ÿ™‚ You’re more than welcome – it is a journey I love to share!

I can say the project itself might have bits of HTML and/or CSS – but you do have the time to research and do it properly – no pressure there.

The interviews were mostly conversational in my case. I believe in this process it is more important to see if you fit the role and the company (and if they fit you) than if you’re a CSS/HTML guru. The trial process itself can become more technical – obviously.

Let me know if you have more questions though – either here or via the contact form on the sidebar!

Sophia June 14, 2018 - 14:44

Thanks Lae! ๐Ÿ˜€

Ann Bingle May 24, 2018 - 08:04

Hi Lae,
Thank you so much for your response, I really appreciate it. Yeah, waiting is really tough. I found out that the person I’m going through with the hiring process is currently at Team Meetup for the whole week so that’s why maybe I still haven’t received any response from him. But yeah I will just keep holding on. CONGRATULATIONS!!! ๐Ÿ™‚ I’m happy for you. I cannot wait for your next post dear. The way you post about the hiring procedure is amazing btw and I love your blog as well. Keep posting amazing blog posts.

Sure I will let you know.

You have a great day!

Ann Bingle May 31, 2018 - 04:21

Hello Lae,

Good day!

I’m happy to let you know that I’m moving to Trial and I am so happy about it. I know it’s not gonna be easy but I will do my best to really ace it. Thanks again for sharing your journey. Hope to meet you in Slack soon ๐Ÿ™‚

Have a great day!

Lรฆ May 31, 2018 - 21:12

Oh – amazing news!!!!! Im so happy for you! I remember how happy i was when i got accepted – and the whole rollercoaster after that… To be honest it hasnt finished yet ๐Ÿ™‚ when the trial starts ping me on slack ๐Ÿ™‚ congratulations on making it!!!!

Ann Bingle June 1, 2018 - 01:57

Thanks Lae ๐Ÿ™‚

Regina Foo July 17, 2018 - 13:45

Hi Lae, thanks for sharing your experience! I love it very much when you included the timeline on the process as it gives me a brief idea on how long should I expected to wait.

Iโ€™ve just submitted my first assignment yesterday. To me, it consists of some of the tasks that I never performed before and has little knowledge to it but I managed to complete it and sent it over to the hiring team. I did not use HTML/CSS in the assignment so Iโ€™m a bit doubtful if theyโ€™ll even contact me for the first interview.

Anyway, congratulations in joining Automattic! Hope Iโ€™ll have chance to chat with you on Slack or meet with you personally during team/company meetup.



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