pictured: latest Automattic group shot (Fall 2013).

Over the past 8 years I have had 8 different jobs. I’ve been an unpaid intern, a youth pastor, a behavioural interventionist, a rent-a-geek (yup), a web developer, and even a day care worker.

This past Monday – I started my 9th job.

I had a crazy idea about 2 years ago.  I wanted to have a job that I not only liked, but loved.  I wanted to work not for a company but with a community that shared my passions, values, culture, and most importantly – I wanted to work hard each day to make a difference in people’s lives.

Why is that a crazy idea?

I say crazy because I think most people stop at a job that’s ok, or a job that’s good enough, or even a job that just pays the bills.  I knew that I needed more then those things.

Like with most questions I have, I began with a google search.  I wasn’t looking for a job, I was looking for a culture and a community that I could come alongside of and make a difference with.

One of the most interesting posts I read back then was “My 8 Core Work Values“, in which Daniel Espinosa talks about figuring out what your core values are and how important it is to find a career that fits those values.

It was almost immediately that I stumbled upon Automattic – the company behind WordPress.com, GravatarAkismet, Polldaddy, VaultPress, Simplenote, Cloudup, and more.

One of the things that caught my eye instantly was the first thing you see when you go to Automattic’s website:

We are passionate about making the web a better place.

That was something I really wanted to do, too.

Then I stumbled across their creed:

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

The creed really struck a chord with me.  I felt like it was describing so many things about me and it was certainly describing the kind of place I wanted to be a part of.

I decided I was going to be a “Happiness Engineer”.

Happiness Engineers are what most companies call the “support” or “helpdesk” team, but at Automattic, they go way beyond that.  It’s not just about answering people’s questions and and getting onto the next customer – it’s about truly engineering people’s happiness, even if it means recommending they stop buying your product.

Before applying for the position, I decided to make a list of everything I should know for the job and work hard at honing these skills. I would practice during my lunch break at my job, I would keep up with all the news about the company, and I decided to go and meet some people who worked there and ask them about their experience.

That’s when I went to WordCamp Vancouver.  Not only did I meet some amazing people from Automattic, but everyone there blew me away.  The community, the volunteers, and the speakers were so kind, generous, helpful, and welcoming to even a stranger like me.  It felt like family right away.  I realized that the community and culture wasn’t just part of Automattic, but it was part of the broader WordPress community as well.

After WordCamp, I sent in my resume and after a few Skype chats, I was ready to start my Trial.

Automattic’s hiring process is as radical as the rest of their work environment.  In past interviews I was used to answering questions like “What’s your biggest weakness” – those are easy.   This hiring process felt more like getting to know a group of friends and discussing interesting questions together and I even forgot I was being interviewed at times.

Doing a “Trial” is a crucial part about joining Automattic.  Many people are used to driving to work, working at a desk or cubicle, and have been trained well in office etiquette (e.g. wear pants to work).  Automattic’s work culture brings a whole new paradigm to work.

Bosses?  Nope.

Schedules?  Sometimes.

Pants?  Totally optional.

Because the job is so different than your regular 9-5, it’s important to have a Trial period to see if it’s a good fit for you, and to see if you’re a good fit for them.  It’s kind of like going on some dates with your new job and if they go well, they eventually “pop the question”.

During my trial – I would go to my regular job at 6:30am, get back home at 4:30, finish dinner by 4:50, and hop on the laptop by 4:55pm.  I would then work on my trial duties until I basically was so tired I had to go to sleep.

After an intense and exhausting 6 weeks, I was given a job offer to become the newest Happiness Engineer at Automattic, and I couldn’t be happier.

I actually miss my job when I’m not working, and the best part is that I get to work with the most creative, funny, best people in the whole world.

If this sounds like something you could be passionate about, I have some good news:  we’re hiring.

18 thoughts on “Joining Automattic as a Happiness Engineer

  1. Reblogged this on Wendomattic and commented:
    This is a great post about the WordPress community as a whole and Automattic’s culture in particular. I think he nails it with this:
    “Happiness Engineers are what most companies call the “support” or “helpdesk” team, but at Automattic, they go way beyond that. It’s not just about answering people’s questions and and getting onto the next customer – it’s about truly engineering people’s happiness, even if it means recommending they stop buying your product.”


  2. Congratulations Mikey on your new job!

    Automattic is a fantastic place to work from what I’ve heard and all the Automatticians I’ve met are stellar people.


  3. Hi Mikey, I have been a WordPress fan for a long time now.

    I found the available job positions on Automattic and I really liked the Happiness Engineer position so I’m doing my research and checking how it is like to work there.

    This post is very helpful as part of my homework and so far, I only have find good comments about being a happiness engineer, I’m finishing my personalized CV for the position. Thanks for your help.

    Any additional recommendations, do you think we can talk or exchange emails?


  4. Great post Mikey! Now that you’ve been seasoned as an HE, what does your daily work/life balance look like?

    I hope to be working you very soon 🙂 If you have to time, it would be great to chat a bit about what it takes to become an HE.

    Hope all is well!


  5. I’m not convinced that I am that “seasoned” yet – maybe in a few years 🙂 My work/life balance is pretty similar to other jobs I’ve had – at the end of the day I can close my laptop and think about other things. Best of luck with your application!


  6. Good question! From personal experience I think it takes a few weeks, but could be longer or shorter depending on the time of year. Best of luck with your application!


  7. Yeah, I know the feel – I wanna join as a developer but I don’t think my current portfolio showcases just how awesome I am… so I’m really going to dig in over the next couple of months, release a few themes and plugins to the open source community to show off my design & coding skills and maybe get a couple of the bosses at my internships to say some kind things about me on YouTube. 🙂


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