Musings WordPress

Fleeing Facebook

After recent events, and after some inspirational conversations at WordCamp for Publishers: Chicago, I’ve decided to ditch Facebook. I’ll start by creating posts/updates on my own blog. I’ve also removed Facebook from my About page.

Excited to test out Gutenberg, in a not-work context:


I’ll cross-post these updates to Facebook for a while, just so I’m not talking to myself. 🙂


Diving into the Chaos: Joining Automattic (Part II)

The Timeline

Automattic is an unusual company, and it isn’t surprising that our hiring process is unique. Here’s a timeline of the process I went through, from A-Z:

Date applied: February 6, 2017
Resume received: February 6, 2017
First contacted: February 24, 2017
First interview: March 8, 2017
Follow-up: March 9, 2017
Second interview: March 15, 2017
Trial start: March 27, 2017
Trial wrap-up: April 26, 2017
Trial summary sent: May 1, 2017

The Initial Application

The first step was like what you’d find at a traditional company — put together a cover letter and resume, and fire it off into the abyss. The similarities end there. Automattic strives to send a response to every single applicant. We will often send specific feedback to potential applicants on how they can improve their skills, and encourage them to reapply once they’re confident that they have the skills we’re looking for. Once they reviewed my resume and cover letter, they had me complete a small trial project. The project does a phenomenal job of ensuring that applicants have a basic understanding of WordPress, how domains/DNS work, and how to effectively use support resources to find answers to specific questions.

Paper shredder eating resumes
How it often feels when you send in a job app

The Interviews

My first and second interviews were conducted via chats in Slack, which is the tool we use at Automattic for realtime communication with our globally distributed colleagues. It was a bit unnerving to be missing out on the visual cues you’d typically rely on during a job interview; instead of a reassuring smile/nod, you’d get a smile emoji or “Yeah!” There are a couple of benefits to having the interview via Slack: we consistently communicate with our colleagues and users via chat, so it makes sense to also conduct our interviews over chat. It also eliminates any potential biases tied to how people sound (i.e., accents, stutters, pitch of their voice, etc.). My first interview revolved around learning about me as a person, and exploring why I was interested in being a Happiness Engineer. Without giving too much away, the second interview touched more on my approach to support and learning.

"Hi Ryan! Everything is going wonderfully, I'm excited to be here. I might have had a teeny bit too much caffeine."
How I started my first interview. I still have too much caffeine.

On Trial

Once I cleared through the initial projects and interviews, they granted access to the “Super Admin” role at This included nearly all of our internal resources and communication channels. “Sink or swim” pretty accurately described the initial feeling of having so much information at my fingertips. Thankfully, since everyone has gone through their own trial at Automattic, everyone remembers what it’s like to be new to the chaos. In fact, we specifically mention that in our Creed:

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

Armed with the knowledge that this trial would decide whether or not I get to stay at Automattic, I put 110% of myself into the trial, and typically dedicated between 25-30 hours/week. Automattic is aware that we may already have other unbreakable obligations (i.e., family, existing job, etc.) that prevent a full-time commitment during the trial, and they’re willing to work with you on that. I spent the first few days of my trial trial learning about our various policies, internal tools, and overall approach to support. As I continued through the trial, I had routine check-ins with my trial lead and other members of the hiring team. The check-ins were pretty informal. The hiring team used them as opportunities to gauge my progress, and assist me in setting goals for the coming week. Automattic accurately says that it’s your trial, and with few exceptions, my trial lead was pretty hands-off in terms of assessing my progress and setting goals. It was up to me to push myself harder, while still setting reasonable goals that demonstrated that I was an information sponge who could truly connect with our users. This was especially important during the last couple of weeks of the trial. I was juggling several live chats at once, while still providing stellar support to each user.

Kermit the Frog typing on a typewriter
Visual representation of my final trial days

The Matt Chat

At just about 4 weeks into the trial, I was given the positive news that I’d be referred to the “Matt Chat.” I responded as best as I could to my trial lead:

Finding out I'd be speaking to Matt about joining Automattic

Here’s where things get really interesting: Matt is an exceptionally busy person as co-founder of WordPress, and CEO of Automattic. After my successful trial, I was expecting a pretty lengthy delay before speaking to Matt. Unbeknownst to me, the team I was assigned to was just days away from their annual meetup. Matt went out of his way to chat with me within a couple of days of my trial ending, so that I’d be hired in time for the meetup. Our chat covered some pretty basic compensation questions, and we also learned more about each other during our conversation. It was amazing to talk directly to the CEO of our company, and the co-founder of WordPress! After signing my employment agreement on Thursday, I flew to San Diego for our team meetup… on Monday morning. I had an unusual first day for a new-hire at Automattic, in that I’d actually be seeing my co-workers face-to-face!

Blogging from the Stratosphere

Typed this up from 35,000 feet while flying home from our annual Grand Meetup. On the same flight as Matt! More on that in a future post, soon™.

Part I: Discovering Automattic

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 – a hosting platform powered by the WordPress software he (and thousands of others) helped to create. It’s important to note that (where the WordPress software is distributed, developed, and supported) is separate from (an Automattic contraption). Matt plays a big role in both: he’s a lead developer at, 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 🙂

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