Automattic: my journey from application to hire

Automattic: my journey from application to hire

Hi! My name is Hannah and I’m a WooCommerce Happiness Engineer at Automattic. Automattic is the company behind, WooCommerce and many other products.

I successfully completed my trial for Happiness Engineer on During my trial, I read as much as I possibly could about other people’s experiences. Good, bad, it didn’t matter. I was so thirsty to know more. I hope this blog post helps you in some small way.


I’ve jumped around a lot in my so-called career. As a kid, when people asked me what I wanted to be when I grew up, I had a phase where I wanted to be the President of the United States. After I found out more about politics, I decided that being a librarian was more my style. As a teenager, I couldn’t decided if I wanted to study English or go into IT. I ended up in IT and studied to be a developer with a focus on real-time systems. When I realized I was more of a generalist, I ended up in support. Becoming a Microsoft SharePoint specialist wasn’t exactly planned, but it worked out.

I’ve learned that asking someone what they want to be when they grow up is a rather limiting question. It’s what you do with your day: the skills you use, the things you learn, the interactions with other people and how you feel about it – these all combine to be “that thing that you do”.

Over the last few years, I had been realizing that consultancy was not for me. There were neat things, but I wanted to focus on helping the customer and seeing the solutions grow. I was tired of project work. I was tired of billable hours. It wasn’t a question of the company. I believe that most IT consultancy companies are similar once you’ve switched out the logo and company values. I had been toying with the idea of finding a long term SharePoint-oriented position somewhere such as a school but that was tricky because I don’t speak the local language anywhere near fluently.


Here’s a summary of the timeline:

First try:

  • 1 October 2014 – Emailed application
  • October 2014 – First chat (Skype)
  • November 2014 – Second chat (Skype)
  • November 2014 – Offered a short project
  • November 2014 – Automattic declined to continue the interview process

Second try:

  • 11 August 2015 – Emailed updated application
  • 26 August 2015 – First chat (Slack)
  • August/September 2015 – Mini project
  • 16 September 2015 – Chat about project review and offered a trial
  • 28 September 2015 – Started trial
  • 3 November 2015 – Informed that I was continuing to the Matt Chat
  • 13 December 2015 – Offered a full-time position at Automattic
  • 15 March 2016 – Started as a full-time WooCommerce Support Ninja

The first try

It was the beginning of October 2014 and I came across Automattic advertised on a remote work site. I hadn’t actually ever heard of them, but I’d dabbled in WordPress since about 2005 and version 1.5. That’s based on my posts on the forums marked as “11 years ago”.  I always thought WordPress was awesome and I had built a number of sites on it over the years.  My roots are in the open source community – while I was very at home in the Microsoft world, I missed the open source philosophy and ethic.

The job opening that caught my eye was for the role of Happiness Engineer, a support position.  I love teaching and helping people understand things, so I applied. If I didn’t know everything I needed to know, I could learn and trying certainly never hurt anyone.

Much to my surprise, I was contacted by someone from Automattic who invited me to a Skype chat. The evening of the chat, I got all set up. I made sure I was dressed neatly, I had a neat place as a background and had my notes at the ready. We had our chat … completely written. It was neat having such a professional conversation via text as I’m used to seeing text-based chats as a fairly informal way to communicate. After the chat, I reviewed the email – it did say a text chat, so that really was my mistaken expectation.

A few days later, I received an invitation to a second chat (I didn’t get dressed up this time) and was asked to complete a small project. I wasn’t sure if I had done a very good job on the project but sent it in.

A few days after that, I received an email politely informing me that Automattic wasn’t interested in proceeding at this time. I was welcome to reapply in the future and a few books were recommended for further reading.

I was more disappointed than I had expected, but that was that. Life goes on.

The interlude

I didn’t have a burning desire to work for Automattic. It looked really neat and the remote work appealed to me but that was it. I didn’t spend the next year actively working on improving myself with the goal of reapplying.

Delivering Happiness and my support philosophy

I really like Blinkist, which is a service that summarizes (mostly) non-fiction books so that you can read them far more quickly.  It allows me to get the gist of the message and pick up the full book if I’m interested. One of the books that I happened to read through that service was Delivering Happiness by Tony Hsu. That book happened to be one of the books recommended after I was rejected by Automattic. It was absolutely fascinating, so much so that I went and read the full version.

“The visionary CEO of Zappos explains how an emphasis on corporate culture can lead to unprecedented success.

Pay new employees $2000 to quit. Make customer service the entire company, not just a department. Focus on company culture as the #1 priority. Apply research from the science of happiness to running a business. Help employees grow both personally and professionally. Seek to change the world. Oh, and make money too.”

– Excerpt from editorial review

This is the book that showed me that there are different ways of doing business, written from a CEO’s perspective. It is possible to focus on happiness: for yourself, the people around you and the company you are working for. There are a number of interesting points – for me, it was how the focus on customers as well as company culture became the foundation of Zappos.

Reading this book was a turning point for me. I looked at company culture in a different light. I realized that support really could be a central tenant of a company rather than an afterthought.  It reminded me how important happiness is.

After reading this book, I also had a much greater appreciation and understanding for how Automattic operated. “Happiness Engineer” wasn’t just a whimsical, fun title but really meant something.

Build all the sites

The number of websites that I built and maintained grew quite a bit during this period. WordPress was the logical choice for these sites.

There was my attempt at setting up a WordPress business site for myself which is now retired. There’s my knitting and sewing blog, I had a professional landing site because I felt I needed  a clear professional persona – that has now also been rolled into this site. I made strides with my SharePoint blog and I got even more involved in public speaking for SharePoint.

There was also the adventure of the online yarn shop. I thought that it was all about setting up a good site – the rest would be easy. So I installed WordPress and WooCommerce and off I went. The Shady Sheep venture is really a story for another time. Suffice to say that I learned a lot and realized that it’s far more fun to build really cool websites than it is to keep up with inventory.

Forum support

After reading Delivering Happiness, I spent more time in the forums. It turns out that there were tons of questions I could help with and that it made me happy to help those people!

It became a small hobby – when I had fifteen minutes of downtime, I’d go check the forums and see if there was anything I could do.

The second try

It was August 2015 and I realized that I was in a really good place to reapply to Automattic and that I really wanted to. I crafted an email explaining why I thought I would be a better fit now, including links to forum threads that I was particularly proud of. I remember telling my partner that I had a very small chance of success at this point, because so few people were hired at Automattic – maybe a 10% chance?

By now, Automattic had moved to Slack which I was invited to. We had a first interview and then a second. I raised my chance of success to 20%. I was given a set of questions to answer, including some that were fairly tricky. These were typical things that a Happiness Engineer would encounter on a daily basis and I had fun answering them. I had never really spent time on before, so it helped me find my way around.

I was then offered a trial! I raised my chances of success to about 45%. The trial would last up to seven weeks and you are paid an hourly rate of $25. The idea is that you spend 20+ hours per week actually doing the work of a Happiness Engineer with full admin permissions to nearly everything. It’s a great chance to find out if the fit is right, both for you and for Automattic. You “report” to two trial leads and you have a trial buddy who you can talk with.

Going into the trial, I wasn’t completely convinced that this would be the job for me. Here are a few things that were going through my mind:

  • Did I really want to leave the corporate world that was known and comfortable?
  • All of the other people in my trial group were hardcore community contributors, they organized WordCamps and so on – how in the world could I top that? (It turns out that this is known as Imposter Syndrome and is pretty common.)
  • What if people hated me because of my work with Microsoft?
  • From what I was reading, people consider Automattic the pinnacle of working in open source, the ultimate dream job. How dare I jump the queue with my lack of open source background?
  • Did I *really* want to do end-user support again?

I decided that it looked fun and I would most definitely learn something, so I would give it my very best shot. After all, that the whole point of the trial is to for both sides to see if the fit is there.

I started my trial at the end of September. The days were long and hard, as I was still working full-time as a consultant while spending 3-4 hours a night on the trial, plus at least 8 hours on the weekend. It was grueling and knowing that the trial leads could end your trial at any time was fairly stressful. I’ve never worked so hard to get a job before in my life.

The thing is, I loved it. I loved helping users. I loved how awesome everyone was. I loved the independence and assumption that you’d handle stuff or ask for help. I started with tickets and then moved into live chat. Helping users directly was even more satisfying. The statistics appealed to my data-geek self as well as to my personal competitiveness. is very clearly scoped, so there are a limited number of variables to troubleshoot – no problem was ever too hard to solve. It might take a lot of research and asking, but I got there.

The support team isn’t really hired by how much you know. During the trial, you need to show how you can learn, take feedback, communicate, grow – and handle the structured chaos that is Automattic.

ShinyWhen you apply to work at most companies, everything is so shiny and great during the interview process. Once you actually get there on the first day, you open up your laptop and you slowly realize that some of the shiny greatness was just a marketing pitch. By doing the trial at Automattic, I got to see what the real work was like.  Automattic is the first company I’ve ever worked with where the shiny doesn’t wear off once you get down into the trenches.

I was also reminded that geeky jokes are encouraged (in the right time and place).  For me, this felt like a breath of fresh air after so many years of corporate conformity.

Within the first few days of the trial, I knew that I wanted to work for Automattic full-time and I was going to do everything in my power to get hired. I hadn’t realized this when I applied, but getting to be a Happiness at Automattic was my dream job. That realization supplied a large part of my motivation for the rest of the trial.

In week six, I knew that the trial leads would be making a decision very soon. I was challenged to take more chats per hour and given a clear goal to meet. That Sunday, I sat down and opened up the chat throttles so that users could start chatting with me. I was open for five chats at once and hanging on! I might have pushed myself a little bit too hard – after all, it was up to me to find what worked, if that was more chats at once or fewer and handling them faster.

The trial leads informed me that they were passing me on to the Matt Chat. It was the first week of November and I made it! I now estimated my chances at 90%.

Matt Mullenweg, CEO of Automattic, reviews all CVs that come in and passes select CVs on to the hiring team. He also does the final chat and makes the decision to offer you a job. Salary is also discussed at that point. Due to all sorts of delays like timezones not overlapping, travel, WCUS and so on, we didn’t finish our chat until 13 December. I’ve understood that this wait is pretty unusual. Either way, at the end of the chat, Matt offered me a job!


I was assigned to the WooCommerce payments team. Due to working in Sweden, I had a three month notice period on my contact, so I started as a WooCommerce Support Ninja on 15 March 2016.

Onwards and upwards!

It really has been quite a journey for me. I’ve learned so much about myself in the last few years, as well as what I find important and what I need to be happy. I certainly never thought I’d be a Happiness Engineer when I grew up, but it’s a fantastic fit. I had no idea how I was going to be able to leave the consultancy world and support myself. I thought open source was cool, but didn’t really understand the value of it.

In many ways, the world isn’t a very nice place. By actively supporting open source and by helping users, I get to help make it just a bit better. Instead of complaining and feeling too small to make a difference, I get to help make the future brighter.

Oh, and by the way – we’re hiring. 🙂

11 thoughts on “Automattic: my journey from application to hire

  1. Thanks so much for posting this!! Right now, I’m doing exactly what you did back then: “I read as much as I possibly could about other people’s experiences. Good, bad, it didn’t matter. I was so thirsty to know more.” So your post absolutely helped me – thank you. 🙂


  2. Is there a channel where we can reach you directly to ask questions? 🙂 I am quite easy to find, thanks to the uncommon name. I’d love to talk with you, as a fellow Stockholm enthusiast.


  3. Hi there ! I pinged you on Facebook, but I’m not sure it went through. You can find me via Facebook or via email (


  4. Thanks Hannah for sharing your experience, I’m actually sending my application today for Automattic, always good to hear about other Automatticians experience. thank you for the book recommendation.


  5. Thank you for this post! It is very inspiring to read all of the different stories about becoming a Happiness Engineer. I an currently learning as much as I can, so I can apply for the position in the near future 🙂


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