Automattic Happiness


I recently made a pretty big life transition. After more than a decade in full-time vocational ministry, I accepted a job in user support for a web development company. This is the story about all that.

The Back Story

In the Fall of 2014, I knew my current position at the church would be changing, my hours would be cut and our income would take a hit. I began looking into freelancing as a way to supplement our loss of income. While researching, I made a few random connections that eventually led me to a company called Automattic, which is the company behind WordPress – the software I’ve been using to build websites for the past 5 years. I then learned that a friend from High School worked for this company and a few days later ran into her at my step-sister’s wedding. We spoke briefly and I decided to investigate the company. I read about the position, the company culture, and benefits, quickly determined it to be a perfect fit for me.

This was all very unexpected.

I was not looking for a new full-time job – although, I was on the lookout for anything God may have for me. This job opportunity was way too perfect to ignore. But pursuing a new job – new career – was not a small decision to make. After 2 weeks I concluded I had nothing to lose and resolved to follow the road as far as it would take me.

Without telling anyone but my wife, I emailed my resume to Automattic to apply for Happiness Engineer.

The Hiring Process

About 3 weeks after applying I had my 1st interview (via Skype text chat). After this, I did a small project, had a 2nd interview and on December 26th was offered a paid trial where I would do the job on a contract basis. The trial is sort of like an audition to see if it’s a good fit for both parties. I had heard that most applicants don’t make it this far so this was a really good sign.

On January 5th, I began my trial. For almost 6 weeks I averaged 26 hours a week learning and doing user support for users – on top of working at the church. It was a really long haul! I did get paid for it so that was a nice bonus (well, a great bonus!).

On the Tuesday of my 5th week of the Trial, I received word that my Trial was coming to an end and I was being recommended for the final interview. I couldn’t believe it! About a week later, I found myself chatting with the company CEO (in what is referred to as the “Matt Chat”. And after 8 hours of on-and-off chatting, I had a job offer!

All in all, it was more than a 3 month process. (Note: Automattic is continually improving their hiring processes. Keep in mind this is how my hiring process went, but may be different for others in the future)

About the Company and Position

Automattic, a web development company, was founded in 2005. In addition to owning a dozen or so software products, it is the company behind which powers tens of million of websites across the internet.

The position I applied for (and now work as) is called a “Happiness Engineer”. This is what they call anyone who works in user support across the company. So for the duration of my trial, I was answering support emails, private forum questions, and talking to users in Live Chat support about their websites, accounts, upgrades, domain issues, etc. I felt very “at home” during my trial. The people were friendly, generous and helpful, the work environment was comfortable, and the job itself was a lot of fun. It became very clear that this job was a great fit for me.

Automattic is a fully distributed company which means all of its employees work from all over the world. All company communication, collaboration, and work is done online through various internal websites and a chatting and instant messaging platform called Slack.  Meetings are held through video conferences. And teams meet up a few times a year in person to work on projects and to charge up on some in-person time together – solidifying the already strong online work relationships. The entire company meets up for a full week once each year for the “Grand Meetup” to work on projects, strategies and have fun together.

How’s it Going?

It’s been over a month now since I began working full-time at Automattic. This has been a pretty big, but amazing change for us. The job enables me to work from home (or from anywhere) and comes with too many company perks and benefits to count! I have flexibility with my schedule. I can take off whenever I need to. I have regained some margin in my life that I can reallocate to my family. We are extremely excited and grateful God has brought this opportunity our way!

Since applying and getting hired, I’ve had a number of people show interest in applying for Automattic. Check us out! We’re always hiring!

Read more stories like this at #a8cday


  1. Always good to see what you’re up to Ben…Never a dull moment! What an inspiration you are. Keep up the good fight 🙂

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