How I became a Happiness Engineer at Automattic Part 3: Paid Trial at Automattic

Part 1: Application Process
Part 2: The Interview Process
Part 3: Paid Trial at Automattic (this post)

What is a Trial?

This is the opportunity to work at Automattic, doing the job you’re applying for. It’s fantastic because you have the opportunity to see if you’d actually like the job and gives Automattic the opportunity to see how well you do the job.

It’s a paid Trial, so it really is a win-win situation. You get to try out the position, paid (this isn’t a salary but $25 hour), and see if you both think it’s a good fit.

When I started my Trial. I was nervous… not really knowing what to expect. Would everyone know I was a newb? Would I fit in? Would I quickly learn how little I really know?

I signed a contract and agreed on a start date.


I knew from the beginning that to get this job I was going to have to work hard. I was already working at a full-time job that I loved. So I planned on working on Trial at Automattic around that, late into the evenings and on the weekend.

I was given all the accesses of a regular full-time Automattician. I had access to all of the internal tools, p2s (where all the communication happens) and documentation.


As soon as I got access I immediately fell down the rabbit hole and read everything I could get my hands on about Automattic. I just remember being truly amazed, and just overwhelmed by the mountains and mountains of information.

What was being on Trial as a Happiness Engineer like?

For me, the Happiness Engineer Trial wasn’t a walk in a park… it was a challenge with a steep learning curve. I was willing to work as hard as I could to climb that curve. I learned more in those 6 weeks about WordPress then I had in the entire previous year. To be honest, my brain hurt a little bit haha 🙂

On my start date, I had 2 days of training. Which was jam-packed with so much information I thought my head was going to burst. It truly was a great crash course to everything within Happiness. My trainers were hilarious and brilliant Happiness Engineers. They were a great introduction into the world of Automattic and Happiness Engineering.

I was trusted with all the accesses of a normal Happiness Engineer. At the end of the 2nd day of training, I was answering real live emails of customers with the help of my trainer. Then on the 3rd day, I spent the entire day working on emails from users by myself. I was terrified and convinced I was going to break everything. I really liked that training was structured this way with two full days of training followed by one full day of working on my own. It allowed me to practice everything I learned.

I was assigned a “Buddy” who was basically my Happiness Engineer friend for the duration of my Trial. We chatted via Slack a few times a week throughout my entire trial, I usually saved my especially silly questions for him and during my first week he was the one I would ping in Slack in a panic, convinced I had broken everything. haha. Basically, he was my guide to Happiness and was a great shoulder to lean on. I still think he’s the greatest Buddy. He was a huge resource and I enjoyed our weekly chats.

The thing that I wasn’t expecting… was to be in complete awe of my new coworkers. Slack was where the majority of the conversations seemed to be going on, and while I wasn’t quite ready to jump into channels and start speaking to people I didn’t know.

lolI do remember reading some of the conversations going on… laughing at their hilarious puns and jokes while also trying to follow along and make sense of some of the troubleshooting. This was the most brilliant, hilarious, and kind group of people I had ever seen. And now a year a half later, I still feel the same way. On a daily basis, I continue to still be amazed by them! 🙂

I was terrified to talk to the other Happiness Engineers at first, their knowledge seemed endless. I couldn’t figure out how they just knew everything. Their genuine kindness not only to each other but also to users, was what really sold me on this job.  Whenever I had a question, they were there to guide me in finding the answer.

It was one of my favorite things about the process, instead of just giving me the answer, using skillful questions they’d help guide me and point me in the right direction.

Chats with the Hiring team

I would chat with my Hiring Lead every other week. Our conversations were very clear and transparent. I always knew exactly how my Trial was going and what I needed to work on and improve. They did review some of my emails and live chats with customers. Offering insights and suggestions. The feedback also outlined specific areas I could improve on. I actually wished I had gotten weekly feedback since I felt like it was so valuable. So I would review my own emails and live chats- trying to see what I would do differently.

Going into my Trail, the area I was most concerned about was feedback. When I first applied to Automattic, I did my fair share of Googling about Happiness Engineers. After reading other people’s experience… I was worried about being blindsided by my Trial ending.  Not knowing why it ended or where I stood during my Trial. I’m happy to report, I never had that feeling during any point of my Happiness Engineer Trial. They communicated with me and they did it often. I would specifically take the areas they offered suggestions and built my goals for the coming weeks around them, making sure I was significantly improving in those areas.

Learning the Ropes

Like I said before, I did not have a perfect Happiness Engineer Trial. I made mistakes, there were MANY times when I didn’t know the answer to a question, and there were points where I felt I was really struggling. For example, there was one week when the internet went out at my house- so after work, I basically camped out at the local Starbucks until they closed. Fighting for bandwidth from the guy who came to Starbucks to watch Netflix. For me, it was a steep learning curve because it required a different level of communication not only with the users but with my new colleagues on top of learning new troubleshooting techniques. I just did my best and constantly worked to improve. I was determined to get this job.

Things started to click for me during my Trial as when I realized that it wasn’t possible to know the answer to everything. It was possible to know where to look for the answer. So I focused on learning where to look, which made each new challenge that much more within reach.

I did continue to work at my full-time job throughout my Happiness Engineer Trial. This resulted in working usually in the evenings and on the weekends. I had a hectic schedule for about a month and a half. It was completely worth it for me.

The hiring decision

At the end of my 6th week, my Trial Leads sent me a ping over Slack and during our chat said they’d like to successfully end my trial.

Since I’m already admitting to all of my embarrassing mistakes in writing, I’ll even admit that I burst into tears and starting jumping up and down in excitement. I still have a screenshot of that conversation in my phone. It was one of my favorite moments of my entire trial, knowing that I made it.


They wanted to successfully end my Trial and send me over to Matt for the final part of the hiring process where Matt would make the final decision about hiring me on. The final part of Interview Process is what Automatticians fondly refer to as “The Matt Chat”.

I was definitely intimidated, as Matt is a founding developer of WordPress, the Open Source software used by over 26% of the web AND the CEO of Automattic.

Since I’m writing this blog post… you probably already guessed how that chat went.

When Matt sent me a ping, we had a great conversation. He’s a super kind and really interesting person. I loved being able to ask him questions and hear about the direction he wanted to take Automattic. He was the only person I talked about what my salary as a Happiness Engineer would be.

After my chat with Matt, he made the final decision to hire me on and sent me an offer letter. I gladly accepted the offer and then the hiring decision became official in the most authentic Automattic way, a p2 post by Matt- announcing that I had been hired. Full of warm comments and celebratory GIFs by my new colleagues.

So there you have it, this was my experience as a Happiness Engineer Trial at Automattic.


Interested in what my job is like today? Read this post about what my schedule is like as a Happiness Engineer working in live chat.


In conclusion…. advice to future Trial Happiness Engineers

I get asked a lot about what advice I’d give to someone who is in a Happiness Engineer trial or just about to start their Trial.

I always say the same thing, so figured I’d write it down here for everyone.

The Trial is as much a process to see if you like the job as much as it is to see if you’re able to do the job. I don’t want to sugarcoat it, Engineering Happiness is hard work. Personally, it’s hard work that I love. While I’m working hard, I tend to have a big smile on my face because I love puzzles, figuring out what’s wrong, and helping people. So it can be addicting.

One of the coolest things about Automattic is the work we’re doing and how we do it is always changing. We’re always testing something new. It’s super awesome to be a part of, but at times it can feel chaotic and overwhelming. Your trial can at times feel the same way, and that’s completely normal. So if you have days where you just feel overwhelmed, that’s okay :), just find a way to push through that. Something that helped me with that, was the realization that personal and professional growth is never a completely comfortable process, it means being outside of your comfort zone, but being outside of your comfort zone is always where the magic happens.

Since Happiness Engineering is hard work, find a way to keep yourself motivated and inspired. That’ll become a regular part of working remotely. For me, I love Lewis Howe’s podcast, specifically, he has a segment called 5 minute Fridays. I could listen to those all day long. Give it a try and listen to just one (they’re only 5 minutes). Another thing I did that another Happiness Engineer (thanks Anne) recommend I give a try during my Trial, was I set up alarms on my phone that had inspirational quotes. So if you find yourself starting to drag during a particular part of the day, set an alarm with a “You’ve got this!” quote. Whatever you need to help keep you on track.

Finally, all those Happiness Engineers that you look up to because they seem to know the answer to everything? They were once right where you are now. They also had to go through the process and learn all of this. So don’t give yourself a hard time by comparing yourself to them. Only compare yourself, to your own progress. Think about what you learned each day or each week. Celebrate those successes and give yourself goals to improve each and every single day. Then whenever you can, learn from those Happiness Engineers that you admire. Even though sometimes they may seem like it, those full-time Happiness Engineers don’t know the answer to everything. What they learned, they learned through repetition and answering these questions day in and day out.

Read through their tickets or chats, and feel free to ping them and ask them questions. I still do this. If I come across a chat transcript that I love, I give my co-worker a ping and tell them how much I enjoyed it and I learned from it. I also ask a question or two to try and learn how I can troubleshoot an issue in the same way. I’ve learned so many time-saving tricks that way. Also feel free to say Hi and ping me in Slack! 🙂