Diving into the Chaos: Joining Automattic (Part I)


If you’re reading this, there’s a good chance you’re interested in learning about the Happiness Engineer position at Automattic. Knowledge is power, and I read quite a few blog posts just like this one both before and during my trial. Hopefully my two posts provide a comprehensive description of what the hiring process, role, and company are like – but if not, you’re welcome to email me!

WordPress and its relationship to Automattic

WordPress is an open-source content management system that runs on PHP, using MySQL for much of the data storage. It was initially released back in 2003, and is now estimated to power over 28% of all websites. This site is one of them! Its co-founder, Matt, created Automattic as a distinctly separate company. Among many other things, Automattic is best-known for WordPress.com – a hosting platform powered by the WordPress software he (and thousands of others) helped to create. It’s important to note that WordPress.org (where the WordPress software is distributed, developed, and supported) is separate from WordPress.com (an Automattic contraption). Matt plays a big role in both: he’s a lead developer at WordPress.org, and the CEO of Automattic.

I found Automattic because of… President Trump?! 

My first encounter with WordPress was back in 2005, when I first gave blogging a try. Thankfully, much about me has changed since then – although I still love WordPress! After the stunning outcome of the United States presidential election of 2016, I was overcome with a wide range of emotions, none of them positive. I was unsatisfied with how sites like Facebook intentionally show you posts that you interact/agree with, and wanted to share my opinions with a wider audience: the internet. I wrote a brief post on political partisanship and how sites like Facebook curate your news feed. While setting up this new blog, I was pleasantly surprised by how much WordPress had advanced since I last consistently used it. It was more responsive, more secure, more customizable, and overall much nicer than I had remembered. I simply had to learn more. While reading about how far WordPress had come since I last used it, I stumbled upon Automattic’s website. As I surfed through the various pages, I found a job posting that seemed too good to be true: Happiness Engineer. I figured Automattic gets thousands of applicants, and that there was no way I’d even be looked at; so, I closed the page and moved on with my day. Despite my best efforts, I found myself constantly going back to that job posting. After a few visits, I was prodded into applying with this little Easter egg:

Automattic hiring page Easter egg

At that point, I realized Automattic was a very different company, and that I had to apply. I paid close attention to their requirements and carefully crafted what I’d consider the best cover letter I’ve ever written. I made sure to emphasize that I have a genuine passion for helping people, and that being able to relate to customers and their perspectives is a big part of providing stellar service. I heard back from the hiring team just under 3 weeks later: they were interested! I had been sent a small project, which was estimated to take no more than 2 hours of my time. There was also no deadline to return the project – I had all the time I wanted. Of course, in my excitement, I proceeded to submit the project within a few hours – there was no way I’d be able to sleep knowing I had an unfinished project commanding my attention! The following morning, I reviewed what I sent, and determined that I wanted to completely redo the project. So I did, and sent an email back to the hiring team, explaining that my excitement got the best of me. For obvious reasons, I won’t disclose much about the nature of the project I completed, other than the fact that it does a great job of ensuring you at least have the minimal amount of knowledge and resourcefulness needed to excel during your Trial. I will reveal that my project was sent over by an Automattician (that’s what we call ourselves) named Deborah, so my project was available at dontdisappointdeborah.blog. 🙂

Part II: The Happiness Engineer Trial, and the “Matt Chat”

2 thoughts on “Diving into the Chaos: Joining Automattic (Part I)

  1. The support team isn t really hired by how much you know. During the trial, you need to show how you can learn, take feedback, communicate, grow and handle the structured chaos that is Automattic.

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