My road to becoming a Happiness Engineer

From Systems Engineer to Happiness Engineer

This is the story of how I became a Happiness Engineer. It is a long text since I wanted to document as much as I remember. And hopefully, it might inspire someone the same as other Happiness Engineer stories inspired me when I applied.

If you are here for some quick tips, feel free to jump to the last section:

Table of contents

The status quo

Have you ever felt it is unlikely for you to find a workplace where you’ll belong and where you won’t get bored? That was me back in 2015. I was longing for a company that genuinely cared about culture. I eventually concluded I wouldn’t find what I wanted in my country, so I adventured into freelance and eventually co-founded a startup (Katana). My main desire was to work in anything related to WordPress while being part of something truly extraordinary.

Two years later, my startup eventually had a roadblock, and I was venturing into a new life (with my partner), so I needed a stable income and got a job in IT Management. However, after a year, I was still feeling the need for a company with a culture. Sadly, I wasn’t getting any replies to job applications for companies in my country. I felt local companies didn’t appreciate my skills, and on top of that, there was an intense economic crisis. Companies were more focused on firing than hiring people.

The call to adventure

After using for three years or so, I found out about and Automattic. I was amazed by Automattic’s strong culture and the possibility of working on something related to WordPress. I was shocked when I found out the company behind was distributed all over the world. So I checked their job openings and found a position in customer support: Happiness Engineer.

How I felt when reading about the Happiness Engineer position:

  • Deeply related to WordPress: Just what I wanted ✅
  • Online support: I can probably do this since I have been providing in-situ support for years ✅
  • English proficiency: I love English, but I have only used it to consume content ❌
  • Communication skills: I’m very good at communicating but in English? ❌

So I decided to leave this dream to someone else who speaks native English and probably has more skills or experience than me.

Octopus running away with a "NOPE NOPE NOPE NOPE" caption
Yep, this was me

My mentor

The reason why I started looking for a job with more meaning and a strong culture back in 2015 was the Delivering Happiness book. This book changed my perspective and what I expected from a company and my life. It planted a seed in my mind which would only continue to grow with time.

An idea is like a virus. Resilient. Highly contagious. And even the smallest seed of an idea can grow. It can grow to define or destroy you.

— Inception

The idea of doing purposeful work motivated me and also made me very miserable. After two years of reading the book and learning about the Happiness Engineer position, I couldn’t take it anymore; I had to take action because giving up was never in my plans. So I started reading from people who were already a Happiness Engineer (I found many blog posts), I convinced myself I was a good fit for the job. On January 1, 2017, I had my New Year’s resolution: To apply for the Happiness Engineer position and do my best.

The threshold

There was a flaw in my 2017s resolution: it didn’t set a date for it. But four months later, after wishing for the Happiness Engineer position, I finally started working on it. I created a Google Spreadsheet and listed things I wanted to focus on, each one with an estimated amount of time:

  • Reading books: I needed to grow more as a person.
  • Taking English courses: I needed to gain more confidence.
  • Participating in WordPress forums: I needed to get an idea of solving other people’s WP questions.

I spent five months preparing myself and my job application. I could have spent more time because I never felt ready. But announced they started supporting plugins and third-party themes, I knew that was my perfect opportunity, and it was when I felt they would need me more.

Blue box with the following text inside "Hey there! We couldn't help but notice that you have visited this page a few times. It looks like you're really thinking about working here, huh? Give it a shot and apply already!"
This would show up when you visited the jobs page over and over again

The revelation

My hunch was correct, and ten days later, on September 6, 2017, I got a reply from the Hiring team and was assigned a project. If I succeeded in the project, I would move on with the interview. So I worked on the project in a way I could reflect:

  • Attention to details
  • Willingness to go the extra mile
  • Researching and technical abilities

I was so excited and anxious about knowing what will happen that I finished the project as soon as possible (which I think was one day). Then almost a week later, I had my first text chat via Slack. After a couple of interviews and answering follow-up questions, I got the best birthday present ever! Only that they didn’t know it was my birthday 😬 . I got confirmation that on November 27th, 2017, I would start my Trial!!!

My reaction:

I was lucky because with the trial so far ahead, I had time to plan for it. I wanted to give everything I could, so at my current work, I asked for all my vacation time (15 days) which would cover half of my trial. The other half ended up being a bit more challenging since I would work from 8 PM to 12 AM.

The start of the Trial

The start of the trial was magical for me. It felt like entering for the first time to Hogwarts. Greeting other Trialmatticians and looking at the reactions of the Automatticians when a sudden wave of Trials joined the Slack channels. I remember a funny Game-of-Thrones-like comment: “Trials are coming!”

Students entering the great hall at Hogwarts
That’s how it felt

Then I was introduced to my Trial Lead and my Trial Buddy. Karen and Fernando, both fantastic, friendly people, as you can expect from any Automattician. Both very direct and transparent. I thought I was going to feel very nervous when chatting with them. But I wasn’t; they made sure it was easy to reach them and ask anything.

The culture

When I started my trial, one of the things I remember the most is this phrase:

Welcome to the Chaos (embrace it, don’t fight it)

Automattic Field Guide

This phrase was on the first page of the Field Guide. Most of the training is self-lead, and I was amazed by how well organized and detailed everything was.

If I had any doubts, I was encouraged to ask in Slack to Full Time Happiness Engineers (HEs). That was scary at first, but after asking a couple of questions, I gained complete confidence because everyone was open, friendly, and always willing to help.

The feedback culture was also something that amazed me. One of the main goals of my Trial Buddy was to provide me with feedback. I found out there was always room for improvement. Not only that, but the feedback I received (and continue to receive) was the best I ever received in a company. The feedback was always kind, clear, and actionable.

The super Powers

As a Trial, you get access to almost all the tools Full Time HEs have access to. When you start your Trial, you get Super (Admin) Powers to help users solve pretty much any issues on their sites. You also get access to tools to manage subscriptions and see technical details like the domain status.

With great power comes great responsibility.

The Peter Parker principle

By having access to such powerful tools, the only thing I could do was to learn as much about them and to ask any questions I had about those (even if the question was too simple). Good communication helped me avoid mistakes, and good communication also helped me solve any errors in a faster, less disastrous way. Mistakes won’t jeopardize your Trial if you can learn from them.

Time and goals tracking

When working as a Trial (and also as a Full Time HE), everyone trusts that you’ll do your best and you’ll work the time you agreed to work. Meaning, no one will be tracking your time or checking you are on your computer.

The best way to make yourself accountable for the time you worked (so you don’t work less than expected or too much) is to track your time. Tracking my time didn’t only help me be sure I had worked enough for the day but also helped me be aware of other aspects of my work:

  • Productivity: Am I making progress? Am I keeping a good balance between quality and quantity?
  • Rabbit holes: With so much information available, it is easy to spend all your time reading and learning.

Hand in hand with time tracking goes goal tracking. During my Trial, my Trial Lead suggested me to set SMART goals every week. It was the first time I had heard of those, and it was a powerful tool.


Automattic has the most extensive network of P2 sites you’ll ever see. There’s a P2 for everything, and you have complete access to all P2s. In contrast to traditional companies, Automattic doesn’t rely on email for daily communication. Short messages can go into Slack, and more significant conversations happen on P2s. That was mind-blowing to me because that means you get access to all conversations happening in the company.

Putting my trial in danger (or so I thought)

The work I did as a Trial felt meaningful and exciting. I thought I was making good use of my abilities (as never before). The work was also intense and demanding (demanding not by others but by myself). I was willing to give everything, and so I did even when my day-job vacations were over. I was so motivated that it didn’t bother me to start my Trial at 8 pm and finish past midnight.

However, I was missing an important part: self-care. I focused on getting to the expected level fast enough, and I was so happy with the work I was doing during my Trial that I was terrified. I was full of fear of messing up the opportunity to achieve my dream job. I felt I wasn’t enough, so I pushed harder. I was so focused on my work; I lost sight of my health.

Almost at the end of the third week of my trial, I got sick. And I felt like everything was lost.

Back to the road

Communication is oxygen. I reached a point I couldn’t continue working due to fever. So I communicated it on my P2 and in Slack. I wasn’t able to keep working, but at least I was able to keep good communication.

I didn’t let sickness beat me down. I got some rest, but I wasn’t vivid enough to work on regular work (tickets and chat), so I did another kind of work: testing. As an HE, you are expected to help in other areas besides support. I loved the idea of testing a new feature before everyone else can access it.

The last week of Trial started, I was back into the game and more nervous than ever. While I was good at receiving and applying the feedback I got, I didn’t felt I was reaching the best productivity level (tickets per hour). Meaning my quality was in a good spot, but I still needed to improve my quantity.

So I started reaching out for advice, I messaged my Trial Buddy, and I also messaged one of the highest performing Spanish HEs. I got valuable advice that helped me to continue improving.

If I have seen further, it is by standing upon the shoulders of giants.

Sir Isaac Newton

The end of the Trial

Before the fourth week ended, I had a chat with my Trial Lead, and I got the HE Role recommendation. Then on January 1st, 2018, I got a formal offer to work as a Happiness Engineer, and one month later, I started my Full Time HE Journey.

This is an awesome video that matched my hype when I made it through the trial

It took me 260 days in total to reach my dream, and be the first HE in my country. That’s specific to my case. I have seen people become Happiness Engineers in way less time.

Advice for prospective HEs

I will divide my advice based on the stages I went through:

Learning and investigation

Books were my mentors that changed my perspective and motivated me to move forward:

Learning about the role you want to apply to is important. You need to fell in love with the role, so you are willing to give everything:

Refine or learn any skills you need to feel comfortable about the position. In my case, I took courses about:

*I don’t specifically recommend these learning sites. These are just examples of what I did.


I was already familiar with WordPress, and I had some experience with IT Support, but I had never provided WordPress Support. So I decided to practice on the WordPress forums:

I started with the forums since I was more familiar with that version of WordPress. Afterward, I jumped into the forums.

If you are interested in joining Automattic you can check the Work With Us page.

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