Diving into the Chaos: Joining Automattic (Part II)

The journey from applicant to new hire at Automattic, as a Happiness Engineer. Part II of 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

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