My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World

Welcome To The Chaos

I submitted my application on October 3rd, and every day from that day on was spent refreshing my inbox. I read from past experiences of other prospective applicants that the wait sometimes lasted months!

Fortunately, I did not have to wait that long, as I received a reply back almost exactly two weeks later. I don’t remember having felt this excited about receiving word back from a prospective employer since maybe years back when I was applying for jobs in Japan.

I’m not sure if anything has changed since then, but it seems that Matt does a first pass on all applications & resumes that come in.

The unusual process starts from the get-go: the CEO does the grunt work. Mullenweg screens all applicants, spending one-quarter to one-third of his time on hiring. That way, when a hiring manager gets a resume, it comes from Mullenweg, and the person is already pre-approved by the CEO. — Business Insider, Billion-dollar startup Automattic hires employees without ever meeting them or talking to them on the phone

The thought that my resume was looked at and directly approved by Matt first is pretty cool!

I received an assignment that I had to complete before actually doing my first interview. It wasn’t overly difficult, and in fact, it was quite straightforward. I could get a sense that the goal was to test if you could follow instructions, in addition to doing a little bit of out-of-the-box thinking.

Sent my project in, and about a week later I got word from Automattic letting me know that they’d like to set up a date to have a chat, which ended up being my first interview.

I wasn’t sure what to expect (but I kind of did). The only impressions I had of what the interview might be like was only from what I read of other past applicants, and those posts were quite dated, so I expected pretty much anything could happen.

The interview lasted about an hour which took place over Slack, and was done completely in chat. I was admittedly nervous going into the interview at first — as previously mentioned it had been literally years that I had a proper job interview. But once the chat got going I started to feel a bit more comfortable. The chat went rather smoothly and there weren’t any questions I felt that I couldn’t handle. It eventually ended on a positive note, and I was given yet another assignment.

This time the assignment was a bit more technically-involved, but again nothing too demanding. I spent some extra time looking everything over before I sent it in.

A little bit over a week later I got word from Automattic asking if I was available for another chat i.e. my second interview.

At this point, I had passed a resume screening, an assigned project, a first interview, another assigned project, and now I was moving on to a second interview. I knew I had to step up my game.

I won’t get into too much detail about this particular segment, but I can say I was mostly interviewed on my knowledge/thoughts about support in general. Unlike the first interview, this one took about an hour and a half. I was so relieved once it was over, but at the same time anxious as to when I’d hear back next.

Then, a few days later, I received an email. Automattic notified me that they would like to advance me to the next stage — the trial.

Naturally, the first person I told was my wife. She knew how anxious I was waiting to hear back and when I told her about the news, we were both excited and happy to finally know I’d be moving forward!

The Trial

Intense. Tough. Grueling. Overwhelming. Demanding. Exhausting.

*what else, um…* NOT EASY.

One might describe the trial all of the above +more. I already knew this was not going to be a cakewalk on any level, and I think the most challenging thing for me during this entire ordeal was to keep my head on straight. Since I was obviously going to be under evaluation, every day there was a constant stress and tension of being, well, ended.

As with anything, both quality and quantity are important factors for producing excellent work, but what Automattic is really looking for in addition to those two points is genuine passion in the work. They are also looking at what kind of value and impact we bring to the table for each and every interaction we produce for both the users and the company.

We care about the work you produce, not the hours you put in.”  —  Automattic

My days were long and tiring, but what kept me going every day was the thought of a brighter future for me and family, and that this trial would only be temporary.

My Daily Schedule (for nearly a month)
6am – Wake Up + Get ready for work + eat breakfast
7am – Leave house + drop my kiddo off at daycare + catch the train to work
8am – Start work
5pm – End work + pick up the kiddo from daycare
6pm – Have dinner + give the kiddo a bath + take my own shower
7pm – 1 hour rest (maybe)
8pm – Trial Work
11pm – Finish Trial Work + Follow up on tickets + follow up studying + P2 work
12 or 1am – Sleep

I was doing my trial on top of already having a full-time job as a teacher and parenting (which by the way is another trial in itself).

Enabled a two-factor authentication security system on the office. I had one too many security breaches from the little 2yr-old humanoid running around.

I was lucky to have a strong support system from many people.

My wife especially was super understanding of what I was going through and helped me out in any way she could. I wouldn’t have been able to get through this time without her.

I was also unexpectedly pinged by different HEs (Happiness Engineers) who were messaging me to offer their support and best wishes before my trial even started. This was definitely one of my first surprises of my trial experience, but very welcoming surprises. Likewise, I did a lot of pinging myself as the weeks went on, asking different HEs for advice on troubleshooting or feedback. Never was I met with a ‘no’ or ‘can’t help you’ vibe. In fact, it was quite the opposite such that everyone was actually happy to help! The mindset is truly different here when compared to other workplaces I’ve experienced, and this is something I love about Automattic’s culture and a large part of what drives that culture comes from the company’s creed.

The Automattic Creed

I will never stop learning.

I won’t just work on things that are assigned to me.

I know there’s no such thing as a status quo.

I will build our business sustainably through passionate and loyal customers.

I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything.

I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation.

I will communicate as much as possible, because it’s the oxygen of a distributed company.

I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day.

Given time, there is no problem that’s insurmountable.

In support specifically, I learned that everyone is dealing with a constant incoming of user issues and problems. The ability to ask for help at any given point throughout a chat, ticket, or any interaction was another thing that significantly impacted my experience with learning and growing throughout the trial. The fact that asking for help is actually encouraged is something I respect. Everyone benefits from learning and teaching others. The systems put in place for asking for help was also a new and innovative area I had never experienced before i.e @mentioning, using “call words”, or posting requests on P2s.

In regards to making constant progression and moving towards a goal, I knew how important it was to receive critical feedback and act on it. I was lucky to have two great individuals guide me through this process — my trial lead and trial buddy — who both let me know exactly what I needed to focus on and improve. Their feedback had always been actionable and I can say I was able to grow from it. Another part of this process that I really appreciated was the fact that I also had the freedom to identify on my own what I needed to work on.

One thing that I quickly learned about Automattic is that the lifeblood of the entire company is communication  — communication is oxygen as the saying goes. I learned and grew to love how conversations, and open communication with anyone for that matter, was only a ping away. I had not once encountered someone who was unwilling to help or inconvenienced to chat. At first it was strange to see how anyone would be so willing to chat with a newcomer, but slowly I realized this is the culture of Automattic, and so I was happy to interact and learn from everyone.

Learning in a dynamic environment was another takeaway from my experience. I’m sure almost all trials and those who already went through the trial could agree, but this was by far the most I had ever learned in such a short amount of time. Every day there was something new to be learned. Never was there a day or moment where I could say I knew enough. There was always knowledge to be gained, and from so many sources. Documentation. P2s. Slack conversations. User tickets. Chats. All of these sources combined was a trove of information, and what I learned throughout the weeks was how to investigate all these different avenues for the answers I needed.

Lastly, I have to mention my trial mates. Of the original group, nearly half of us made it through. It was certainly a hit to the heart, as well as a proper wakeup call every time we saw someone go. We were our own team in a way. We looked out for each other, shared encouraging words when times got tough, and even though not all of us were as active as others in our trial group, I felt we all ended up coming out together as a team, and that’s something I’ll always remember from my trial.

Anyways, it seems like I’m already skipping ahead here so I might as well wrap it up XD

It was five days before Christmas and I couldn’t be anymore anxious as to when this trial was going to end. I remember thinking to myself that this would probably be the worst holiday season ever if I didn’t make it at this point.


And there it was — my trial lead with a new assignment for me and a request for a chat.

I finished up my assignment, and anxiously awaited for our scheduled chat which wasn’t until the next evening. By now, I had made peace with myself that whatever the outcome, I would reassure myself that I had done everything within the best of my abilities throughout this trial. There was always next time should it have been decided that I would not move forward. I just went into it ready to expect anything.

The chat started off just like any other and lasted about an hour. And so to not get into any specifics, as you can probably guess, it ended on a happy note. I was being recommended to join Automattic as a full-time Happiness Engineer!

It was nearly 12am by that time and I still had work the next morning, but I couldn’t sleep at all because I was just way too psyched. The next evening we celebrated with pizza & a much needed craft beer 🙂

Screen Shot 2018-03-21 at 19.00.34 copy.png

Employee #698! As far as company employee history in Japan is concerned, I was the 4th Automattician to be employed in Japan! The one before me was the first native Japanese HE. Before they were hired was a mobile developer, and the first Japanese hire ever being Naoko 🙂

NET (Native English Teacher) Timeline (3yrs 7mos)

  • 2014 July 28 – Submit Resume via Job Subscription Service (Hokkaido Insider)
  • 2014 July 30 – Meeting with principal + Offer
  • 2014 August 18 – START
  • 2018 March 20 – LAST DAY

HE Timeline

  • 2017 October 03 – Submit Application (Resume Screening)
  • 2017 October 18 – 1st Assignment
  • 2017 November 04 – 1st Interview
  • 2017 November 05 – 2nd Assignment
  • 2017 November 13 – 2nd Interview
  • 2017 November 15 – Trial Offer
  • 2017 November 27 – Trial Start
  • 2017 December 21 – Trial End
  • 2018 January 02 – HR Chat + Offer Letter
  • 2018 March 21 – START

If you made it this far, first of all, thank you for reading! This post is actually the first post of a chronicled series titled, The ‘W’ Series, of how remote work came knocking at my door, and influenced my life for the better.

My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World

Welcome To The Chaos I submitted my application on October 3rd, and every day from that day on was spent ...
Read More

Swagged Out

It's been a while! And I just want to reflect on the past 5 weeks since I started with Automattic ...
Read More

Putting The ‘Flex’ In Flexibility: What It’s Like To Work On My Own Time

The option and ability to work when I want has been an amazing employee privilege since joining Automattic. There are ...
Read More

Home Office, Cafe, Coworking Space, Oh My

Nearly four months ago, it took me almost an hour to go from door-to-door for my commute to work. I'd ...
Read More

There’s No ‘I’ In Team

I'm grateful to have a joined a company that is built on remote work culture, as I quite enjoy having ...
Read More

01 – The Why: My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World
02 – The What: Swagged Out
03 – The WhenPutting The ‘Flex’ In Flexibility: What It’s Like To Work On My Own Time
04 – The WhereHome Office, Cafe, Coworking Space, Oh My
05 – The Who: There’s No ‘I’ In Team

You might also be interested in this post as well: Automattic Grand Meetup 2018: Sunshine State

And finally, it might be worth mentioning that Automattic is hiring 🙂

Posted by

Movement. Growth. Ambition. Everything Builds.

12 thoughts on “My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World

  1. Thanks for sharing your story, Paulo. Even though I knew the outcome I still held my breath a little there at the end, nervous for you! The GIFs were perfect too. Congrats on finding a career you love and on your beautiful family as well!

  2. I believe they’re always hiring. Lol. How long did it take you to do all those self-taught courses? I’m planning to apply, and I’m pretty glad I ran into your blog. I think I might do the same thing you did – take a lot of courses to prepare myself for the application.

    1. I’m pretty glad I ran into your blog.

      Thanks for stopping by! And I’m glad you were also able find something useful 🙂

      How long did it take you to do all those self-taught courses?

      In total, give or take 3 years — a bit long, but this was on top of a full-time job, parenting, and not having any background in web development. And I literally dipped my hand into everything i.e. programming, digital marketing, design, etc.

      I might do the same thing you did – take a lot of courses to prepare myself for the application

      Yeah, that would definitely help! If I were to look back on what I could have done to prepare more effectively, maybe I would’ve considered focusing more on CSS proficiency, WooCommerce, and making sure I know how to work & navigate the platform like the back of my hand 😄

      I’d be glad to answer any other questions, so feel free to shoot an email anytime:

  3. What a journey! I recently applied to become a Happiness Engineer, and I’m very anxious. This would be my dream job and I can’t wait for my first interview.
    I’m currently learning JavaScript with TreeHouse and Codecademy at the same time, using the second to practice rather than as the primary source of learning tool. I’ve also learned CSS, HTML and Python from Codecademy but I might need to practice and start working on some websites of my own, to experiment and stuff.
    While the degree I’m pursuing at university is not related to tech at all, I really want to be a developer and I think the best way to do it debt free is through self-teaching.

    1. I recently applied to become a Happiness Engineer, and I’m very anxious. This would be my dream job and I can’t wait for my first interview.

      Nice, and best of luck! If you haven’t already, check out the Happiness Engineer blog:

      I really want to be a developer and I think the best way to do it debt free is through self-teaching.

      Absolutely. Being self-motivated to continuously learn is an invaluable quality to have. Keep at it, and you’ll eventually find that many opportunities start opening up for you 🙂

  4. Hey,
    This is the very first time, I read any post for word by word without any break. Most of the time, I read few sentences and just get the overview.

    But your post and the journey to Automatic keep me curious to read what will happen in the next line.
    It will really awesome.
    It also encouraging me to do my preparations for Automatic.

    Thank you for inspiring. 🙂

Leave a Reply