I’m Joining The VIP Team at Automattic

I can’t believe that I’m actually writing this post. Monday, July 16th, 2018 will mark my first day as an Automattician. I’m joining the VIP team at Automattic as an Enterprise Happiness Engineer. I’m so incredibly thrilled and humbled by this opportunity.

The Backstory

I’ve applied to Automattic before – first several years ago not long after I got into WordPress (no interview), and again last December for a Code Wrangler position. I made it through to an interview in January, but totally bombed it.

Pro Tip: Don’t try and logic your way through an answer to a question you don’t know the answer to. Admit that you don’t know it, but let them know you are able to find the answer.

I was pretty disappointed after my failed interview and, needless to say, my self-confidence was thoroughly thrashed. I told myself that I’d take three or four months and commit to being a better developer and try again. But, before I felt ready to apply again, I got word in late March that my current job was going away – my boss had taken a position with another company.

I had a decision to make – did I want to try and take over our clients and work for myself again, or go out and find another job. My wife and I went through the pros and cons of each and, in the end, decided that the risk of working for myself outweighed the potential rewards. My old boss was very flexible and let me decide how and when things were going to wind down. We decided that my job would end May 31st and I started picking up a few extra freelance projects to make sure I had an income stream coming in.

I started telling people in various Slack teams that I’d be looking for a new job soon. Someone I was working with on the organizing team for WordCamp US sent me a DM on slack and said that her team (VIP) was hiring for an “Expert Debugger.” After chatting about what that meant and job description, I was hooked. Debugging is one of my favorite things to do as a developer – I love finding and squashing bugs.

The Process

I applied on April 4th and got a response back the next day saying that they wanted me to interview! Went through my interview on April 10th and it went WAY better than last time. There were some general get-to-know-you type questions, and then some technical questions, followed by kind of a thought exercise.

I was told that the next step in the process was a code test and they’d let me know soon if I’d be moving on. About a week later I got word that they wanted me to continue! Still couldn’t believe I had gotten this far.

The code test was taking a plugin (purposefully buggy), and fixing it up. I spent several hours over the next three days going through the code fixing things like formatting, slow queries, and errors. It was one of the most stressful things I had ever done in my career. Second guessing every decision I was making – wondering if it was going to be good enough. When I was confident (as I could be at that point) I had done all I needed to, I submitted it and was immediately stressed about how I had done. Luckily I didn’t have to wait long because the very next day I found out I had passed!

The next step of the process is the trial. Sounds ominous. Basically, you get brought on as a part time employee and do various tasks that you’d be doing if you were hired on full time. Also, they can decide to end the trial at any point if they feel like things aren’t going to work out. Terrifying. I’d be working about 10 hours per week for four weeks. Started my trial on April 30th and it was pretty surreal.

My first week was spent working on some GitHub issues for the Automattic plugin Zoninator. It went great, my trial lead assigned me issues on GitHub and then I just responded to how I thought they should be handled. I was able to write some code, submit pull requests, and discuss plugin features.

The second week wasn’t as smooth. I was to move on to taking on some ZenDesk support tickets but to really do that I needed access to certain systems. Access that should have automatically setup but for one reason or another, things never got put in the right place so I couldn’t do what I needed to do. The week was spent conversing about the issues with the systems team, figuring out what the issue was (thankfully it wasn’t something I had done), and then confirming it was fixed. All the troubles ended up delaying my trial for a week.

The second week (take 2) went much better. I had access to what I needed and things were rolling along. Answered some tickets, fixed some issues, and learned A TON. It was really interesting to learn how the systems worked and how they were different than self-hosted WordPress.

During week 3 of my trial, I was paired up with a developer who was going to have me work on another plugin – Gutenberg Ramp. This plugin makes it possible to control the transition over to the Gutenberg editor by letting you specify post types or post IDs that should use the new editor. I was assigned a few issues, and again was able to write code, make PRs, and contribute to a plugin that would be used by VIP clients.

For week 4 of the trial, I was back in ZenDesk. Answering more tickets, although I didn’t need to have someone approve my responses this time around. I still usually asked for feedback before posting just to make sure I wasn’t doing_it_wrong(). Friday was the “final wrap up” call and would decide my fate. Dun dun duuuuunnnnnn!!!!

The final step of the process is having “the chat” with the head of VIP to determine whether or not you’d get an offer. So during the final chat with my trial lead, I was told they wanted to send me through for “the chat!” I was beyond excited. I made it to the final boss! I just needed to wait on them to figure out a few things internally before the last interview.

The Wait

“Cool,” I thought. The wrap up call was on the last day of my current job – timing couldn’t be better!

One week went by – “Sorry, just a bit longer.”

Doubts crept in. “OH MY GOD! They decided they DON’T want to hire me after all! I’m a terrible developer! What am I doing with my life?!?! I should just delete my account!”

Another week – “We’re SO sorry! We’re really trying to get this settled.”

More doubts.


Finally got news on June 27 – not the news I was expecting, but news. They ended up deciding against creating the position I had applied for, but they still really wanted me to join the team. So they asked if I’d join as an Enterprise Happiness Engineer. I’d still be doing debugging, just maybe not as deep as with the other position. I was pretty shocked, but it still sounded like a position I’d love to have so I agreed!

I had my final interview earlier this week, signed my offer letter yesterday, and I start Monday.

Again, I’m so incredibly excited for this new challenge and can’t wait to get started. It’s been a crazy path to get to where I am today and yesterday marks the end of one of the most stressful times in my life. But it’s all worth it because I now work for one of the very few companies I’ve ever dreamed about working for.

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