My Happiness Engineer Interview with Automattic

Jenny Medeiros
6 min readNov 7, 2017


Blue image with words ‘Automattic’ and ten logos of the platforms they built.
Credit: InfoQ

So you finally put in your application to become a Happiness Engineer for Automattic, the company behind, Gravatar, WooCommerce, Jetpack, and so many other products that most have heard of.

You got the generic response saying your application was received, and now you’re in the ‘research stage’ to see what other people went through at this point in the process.

Well, today I had my first interview with Automattic and was somewhat prepped for the questions, thanks to many blog posts from others who also went through the hiring pipeline. So, I thought I’d return the favour and describe my own experience.

Out of fairness, I won’t go into too much detail about the interview questions and project points. Although I’m sure Automattic changes them for every round. However, I will give you a good idea of what to expect.

The First Assignment

After you put in your application, don’t hold your breath because it’ll be a few weeks until your next contact with them. In my case it was around three weeks, and I was sure I hadn’t even passed the pre-screening at this point. But, lo and behold, I received an email from one of the hiring managers with the ‘first assignment’.

It was a list of things that had to be done with a WordPress website. Some of it was easy, some of it was technical — from simple configuration tweaks to adding DNS records. You’ll have to really dig if you’re not all that tech-savvy, but it can be done. I sure did my fair share of forum hunting and flailing to get through it, but after 6–8 hours of panicking, I got it done.

I checked, double-checked, and finally submitted my work with a feeling of pride and creeping anxiety.

Another few weeks passed. I concluded I had failed. I floated between staring at the wall in resignation and looking for work elsewhere. Then, one day I got an email saying something along the lines of ‘thank you for completing the project, are you available for an interview at _____?’

After pacing around and re-reading the email in disbelief a few times, I carefully typed out a response. A few hours later, the interview was set for the following week.

Interestingly enough, it wasn’t a Skype interview or even a phone call. It was on Slack, a team collaboration tool (chat app thing) many companies use to keep their people in touch. I had uninstalled it a month prior, after leaving my old job at a distributed web company. Slack snickered as I downloaded it once again.

The Interview

On the day of the interview, I got up from a restless night of overthinking and went through my notepad full of possible interview questions and answers. I got these by going through the blogs of various Happiness Engineers, like Sandy McFadden and Andrea Badgley who wrote posts that give you a really good sense of what the job entails. Read them. Trust me, you’ll need it.

At 11:30 am on the dot, the hiring manager connected and informed me the interview would last about an hour and she would ask me a series of questions.

I returned a cheerful ‘Okay!’ — as though I wasn’t mentally scream-vomiting from anxiety — and the interview began. One blogger said it would be all personal ‘get to know you’ questions. Another blogger said theirs was more of the ‘proper interview’ type where you describe your customer service philosophy and whatnot. I was somewhat ready for both.

Except what I got was, ‘Describe how you handled the project we sent you’.

It had been WEEKS since I had sent that first assignment. At this point I hadn’t the foggiest idea what the first task was. Thank the hiring gods this was a Slack interview and not a video call.

Luckily, I hadn’t bothered removing the assignment from my desktop, so I pulled it up and scanned it in a panic. After a few minutes I managed to give her a sketchy description of my process, which she accepted with a ‘gotcha’, and then hit me with the next question.


She seemed to be interviewing various people simultaneously, leaving me waiting (on edge) for her confirmation and next pasted question.

This back and forth went on for about an hour. The questions covered things like how I had heard about the position and what I expected from the job, my ability for remote work, and my history with WordPress.

I wasn’t doing too badly (I think) and did try to squeeze in some jokes and make the conversation a little lighter. Eventually she sent a smiley face or two and I felt like I was making progress. But honestly, I had no idea if I was doing well or not.

Friends: how’s it going?? Me:

After the Slack chat was done, I received a follow-up email with around 14 more questions. About nine of those were customer support samples, which I took a long time to send back (the next day, if you must know).

Supposedly, if you pass this step you’re called into another Slack chat where they give you the 101 on the Happiness Engineer (paid) trial period. After that, you get invited as a full timer.

Legend tells that applicants rarely get accepted on the first try. We shall see.

The verdict

After another productive day of misery, I received an email from the hiring manager with the following:

‘Thank you for taking the time to apply.’

Oh dear.

“But we won’t be moving on with the trial.”

‘I suggest you participate on WordPress forums to gain more experience with customer support.’

Translation: you’re exceptionally bad at helping people — at what drunk-o-clock did you decide to apply for this job??

And that was that. I sent back a sheepish ‘thank you for your time’ and laid face down in a puddle of cereal for the next two hours, thinking of much better answers to the 14 questions I had so fantastically failed.

But don’t take this as a bad omen for your own interview. Right now, you know much more than I did when I started and can use that to your advantage.

So if you’re at the stage just before the interview, take what you can from my experience and poke through the posts I linked to. You will most definitely feel more prepared for what comes next.

Oh and, good luck!



Jenny Medeiros

Tech writer/editor who dreams of living in a sustainable house with a delightfully stupid cat.