My strange experiences with Automattic: Part 1

This is the first part of a series of posts about my experience with applying at and then working for one of the most prominent companies in my line of business, which given my experience at the time was a logical step in my career.

As well as being a pioneer in remote and distributed work, Automattic is one of the most well known companies in the WordPress space, with its CEO regularly boasting about having access to an international talent pool.

To many, like myself at the time, it is a highly desirable workplace and it has employed a lot of well known, influential and highly skilled people in the WordPress sector, who work on and support products such as, Jetpack, Gravatar, WPScan and others.

There have been books written about this company and in fact, I did lose my copy of The Year Without Pants on a train somewhere in the Netherlands just before signing my contract, which today sounds like a bad omen.

There are many blog posts out there about the application process at Automattic, the company has generally welcomed those and I don’t expect things to be different in this case.

However, my hopes of Automattic and its leadership learning from this are slim and I urge those thinking of applying there today to think twice — and those thinking of leaving that here is life after Automattic and that burnout and trauma is sometimes more visible in the rear view mirror.

It has been a while, but it has taken some time to be able to reflect on things as a whole. I have briefly mentioned some of the things I will discuss here on social media or even lashed out over them in order to reach for some form of closure, but the whole story needs to be shown as a part of a larger context.

I still am friends with, highly respect, stay in touch with and have worked with many of the people I worked at Automattic after my departure, but that does not excuse the systemic management and leadership issues that were at play.

In the beginning there was an application

In late 2017, I applied at Automattic, which I had eyed for a long time.

I had been dealing with unemployment for a while and I was at the verge of simply giving up on ever being employed in Germany again. This in addition to my home country of Iceland not being big enough for anything at the scale and level of quality I wanted to keep working at, applying at Automattic was a logical choice.

I took the plunge and sent in my application for a “code wrangler” position (the internal jargon for a software developer) after people I knew on the inside and had been there for a while urged me to apply.

It took only about a week to get a positive response and after a couple of weeks of serious flu on both sides, I finished an intensive interview over Slack and a test project was sent over, which I did finish without too much fuss, including a technical interview about it.

The process

Automattic’s hiring process, as it was advertised was not bad on paper, albeit a bit longer than I would like. Knowing someone on the inside who can recommend you gets you past the line, you start with a rather intense introductory and technical interview over Slack, get a practical and realistic test project and once you succeed you should get an hourly trial contract for up 3 months (for as little $ 20 an hour), and succeeding there gets you hired after a call with the CEO.

Or that’s what it says on the tin. The reality in my case was a series of negligence, bad management practices and the enforcement of a work culture that does not suit one of the cornerstones of the WordPress community, a respected and prominent company that was close to crossing into a five figure staff count at the time and it seems like the so-called “Matt Call” with the founder and CEO as the final step had to be skipped by those being hired around the same time as me.

In my case the application process took 11 months — almost a year!

Beginning the trial project

Automattic follows The Principle of Least Privilege when it comes to trial contracts, almost to a fault.

You get access to a couple of sections of the internal staff handbook; which starts with the word embrace the chaos, a handful of internal blogs and no way of seeing anyone’s availability via a calendar service, which makes coordination with other people very difficult if not impossible.

I was assigned with improving or replacing the date picker in the new Gutenberg editor, with an emphasis on accessibility. As weeks and then months passed, this became a communication exercise more than anything else as I was coordinating with members of the WordPress accessibility team and I also needed feedback from lead figures on the design side of things, who were working for Automattic themselves.

I was asked to help with other projects as well, especially in terms of accessibility and there were some serious accessibility issues to deal with.

Hurdles, closed doors and time wasters

Strangely enough, the lack of access and coordination lead to the most challenging part of the gig being to get face time and to work with people who were employed by the same company as myself in order to get any useful feedback. Everyone else, even the big names, had time to communicate and coordinate.

Access to calendars and the internal blogs of the relevant teams may have factored in here, but my assigned coordinator should have been able to facilitate that access.

Not having access to most of the resources I needed or just someone competent who knew which codebase was in which Subversion or Github repository, documentation (mostly in the form of internal blog posts which I did not have access to) or just information on when certain key people are taking their time off made it all but impossible.

The latter project was surely the weirder one of the two. In order to gauge my ability to work asynchronously, I was asked to contact someone on the other side of the planet and offer to help him out with something that was approaching a deadline.

“No it’s okay, I don’t need any help with this” he said as if he really did not want to work with other people. Insisting on this being a part of my trial, he ended up telling me to wait until he was ready. A week or so later, as I had been staring at Slack into every night, hoping for a response, he had disappeared on vacation in Fiji.

You can imagine what this felt like.

But there was always the feeling of things potentially improving once I got over the current hurdle or when I’d be hired full time. (They did not.)

A coordinator who didn’t coordinate

This all was on top of a long radio silences from my trial coordinator was just so abysmal. I would sometimes chime in to the Slack channel that had been assigned to me, sometimes with weeks or months between interactions on Automattic’s part. But I pushed through.

The fact of the matter was that this contract was extremely sporadic, but I think if I had gotten enough tickets assigned to work on along with the initial one, I could have been able to clock in enough hours to stay afloat financially and would not have had to move into a slummy flat in a condemned building, while being at the verge of homelessness.

I also think it would have been manageable had the trial contract been limited to the promised maximum 3 months, even with sporadic hours and the blatant disrespect to my time.

I can understand that those I was working and coordinating with having the the best of intentions, including my trial coordinator (who did not coordinate much) but there is something seriously wrong when any potential employer wastes almost a year of someone’s time, and working under those conditions can make it difficult to have any certainty of this not being deliberately malicious or a part of the test somehow.

I had spent a large portion of my career looking up to a lot of people working at Automattic prior to this humiliating process. You would not expect a company like that to drop the ball repeatedly like this, but they did and it was difficult to process all that.

Signing the contract

Had I not ended up in a bad financial situation and a really bad state of mental and physical health during the extensive trial period, I don’t think I would have signed a final contract or accepted to start on a short notice, but I really had no leverage or choice at this point.

Just to emphasise this, after how I was treated during the 11 month application process, I was in no condition mentally or even physically to work full time but I had hopes of a new job being able to help me recover somehow.

The monthly enumeration was enough to beat any offer in Germany, but not too great for a contractor with no legal protections as an employee.

The fact of the matter was that I needed the money in order to recover financially, reconcile things such as my health insurance and get back into something resembling a middle class lifestyle and this was the only realistic way forward.

More to come

I aim to continue the story next Friday.

In the next post, I will go into what happened during my first day at Automattic, my reactions to the Grand Meetup, which is an annual all-hands company event that was held in and around Disney World in Florida and how my hopes of things improving over time never materialised.

If you want to get in touch over this story, then my contact information can be found on my website at