My Automattic Story: Trial to Hire

“The size of your dreams must always exceed your current capacity to achieve them. If your dreams do not scare you, they are not big enough.” ― Ellen Johnson Sirleaf

My background

As a freshman at UNC Chapel Hill, I had the opportunity to have a workstudy job. After looking through the typical jobs working at the Planetarium and at a couple of day care centers, I stumbled on a job working for With no knowledge of websites and with a long history of writing on (since 2005 or so), I decided to send an email to apply for the job. One short interview by the Old Well later, I got the job as an Instructional Technologist. I immediately dove into things creating sites like where I could post reviews of food in the Chapel Hill area online for other people to use to decide where to eat.  I then created UNC where people submit and read posts based on different locations, story theme (happy, random act of kindness, cute, funny, etc.), and school year. Neither of these aforementioned sites took off but through the process of building them I learned a ton about site design and thought a lot about how you would create a site that would cause users to want to be engaged in your content. After tearing my ACL and going through an incredibly tough recovery process, I created my sophomore year as a way to connect those on campus who have torn their ACL or are in the process of recovering from an ACL tear. With multiple rugby teammates (yes, I played rugby at UNC) with torn ACLs, I quickly gathered their stories, advice, and resources they used to create the site centered on giving people going through the process the information they would need to have a successful recovery. I interviewed the doctor who performed my knee surgery as well as the athletic trainer who helped me during my recovery. Finally, I created a forum for people to post questions and see other’s responses. Thanks to this work, the site is now linked to the UNC Campus Health homepage as a resource for those going through recovery.

My perspective has been profoundly shaped by the two worlds I am wedged between: Psychology and Technology. As a psychology major, I found myself critically thinking about how websites can be used to help and to connect. On a day to day basis, I found myself bouncing back and forth between the two with my mind buzzing with ideas. As soon as my technical skills caught up to my never ending ideas, I began creating sites built on the idea of connecting, sharing, collaborating, and supporting. I fell in love with helping non profits and still work with the North Carolina Reading Association and the North Carolina Press Foundation extensively.

Quickly my role with progressed to a Senior Support Staff member to a Web Support Specialist. By the time I graduated, I was leading training sessions with department members, leading migrations for department sites, and managing the creation and development of a variety of sites on campus (including At the very end, I was beginning to help with the redesign of the Information Technology Services site!

How I found Automattic & Applied

In March 2014, some of the team from went to a VIP meetup with Automattic. They came back and couldn’t stop talking about how much fun they had and how I needed to apply. I was apprehensive at first. I had read Scott Berkun’s book previously and doubted whether my skills were where they needed to be. I read the Work With Us description and thought long and hard about whether I should apply. Throughout all of college, I had mostly worked remotely and was comfortable with the idea. Being an introvert and a self motivated person, I felt like I could succeed at this role. But it’s Automattic?! I dreamed of working there but didn’t know if it was possible. I began drafting up an email but four hours later had only managed to change around a bunch of words. Acting on impulse, I sent it in. This was March 2014! By the time graduation rolled around on May 12th, I had not heard back. A bit discouraged, I decided to send another email in (I really wanted this job). The day after I took a job in San Francisco, an email appeared in my inbox asking me to talk. The email was from someone at Automattic. I immediately set up a time to chat.

What does the application process entail?

  • Application Submission (Matt reads every application)
  • Interview #1 with a mini project
  • Interview #2 with follow up questions from the project and skill questions related to WordPress
  • Trial Contract Spanning 4-6 weeks
  • Final Interview with Founder of WordPress and CEO of Automattic, Matt Mullenweg

After making it through the first two interviews, it was time for my trial. I put the trial off for about a month so I could get adjusted to San Francisco. My grandfather also passed away during that time and I needed time to grieve. July 7th rolled around and it was time for training. I spent a total of 12-13 hours over two days in training with two other people who were “trials”. We were taught the in’s and out’s of WordPress and Automattic. As far as a crash course goes, it was great. The next day, you begin answering tickets with access to everything in their system.

Week #1: Dive in & Connect the Dots

This week seemed to be about connecting what I already knew from my previous work to specifically. The major things I learned and focused on this week were Refunds/Payments and Domains (in all their glory). I had not dealt extensively with either prior and found the two to be highly interlinked. The thing that surprised me the most was how many resources there are to find an answer and how sometimes the answer you find is outdated. I was also very surprised at how quickly I fell into a solid workflow.

My feedback session with my trial buddy was very general and more of a check-in. One thing that stood out to me from this conversation was the following one liner: “The trial, then, isn’t to prove them wrong. The trial is for you to prove them right.” I think this is something that should be told to all trials. It left a very powerful impression on me.

Things to improve: Looking in more places and in the right places to figure out the real problem a user may be having. Formatting my responses better so that they are more user friendly.

Quote of the week: “The trial, then, isn’t to prove them wrong. The trial is for you to prove them right.”

Week #2: Slow Down: The Devil is in the Details

This week I found a groove in terms of quantity. I felt comfortable going through tickets thinking I found the answer and feeling good in my responses. This left some users pleased and others baffled. I made mistakes that, looking back, seem obvious now (thankfully). Whether it was minor spelling mistakes or forgetting to check the resources available, I missed out on some chances to provide quality. However, this was not the norm and majority of my tickets did seem to go well. What surprised me this week was how wonderful and warm the conversations I had were. I tried not to jump around and ping a bunch of people that worked at a8c to talk. I am much more of a 1 v 1 person and found that my desire to truly get to know people was reciprocated.

My feedback was centered on improving quality, slowing down, and really thinking about how I was phrasing/formatting my response. The main message was that engineering happiness is about solving problems users didn’t know to explain they were having (love that).

Things to Improve: In one word, quality. I needed to focus on managing my time better after this week as well.

Quote of the week: “Luck = Something you can generate here at a8c.”

Week #3: Above and Beyond

This week something clicked in terms of how to investigate problems and where to look for certain things that may be wrong. I remember feeling that I understood the support documents, forums, and blog posts much better at this point so that my mind was already turning when I read tickets. The main surprise was having another full time employee closing out some FRs for me! This was a blessing and a curse as I had relied on that previously to know where my tickets stood.

Feedback for the week was really strong from my trial buddy with a lot of positivity about my interactions with users. However, I felt a nudge to “step it up” and do more to solve a user’s problem so they are successful in the future. Whether it was providing a more exact link or doing something for a user instead of just sending instructions, I felt like this was a turning point for me in terms of how I viewed support.

Things to improve: Providing more specific help rather than general help. Find the EXACT solution not just a solution.

Quote of the week: “Invigorating is a word I used a lot to describe my trial too.”

Week #4: Balance & Brevity

I went into the fourth week with the mindset that I would go above and beyond for users. I remember spending probably twice as long on tickets rewording and reformatting to try and cover every angle I could. I learned how providing as many user specific details as possible helps guide the user through steps (i.e. mentioning site URL, dates, etc). This week was probably the toughest week for me mentally and emotionally for a variety of reasons. I was constantly a bit worried that I needed to be a “mindreader” for the user and became a bit hesitant to ask questions first before providing solutions.

The weekly feedback was very centered on being brief and balanced. There was some mixed messaging but all of the feedback centered on how situation dependent everything is and to really recognizing the appropriate response, length, and tone of a message.

Things to improve: Honing in on finding the right solution (response, length, tone) for that specific situation. Also, I needed to learn how to set boundaries on the help that I gave.

Quote of the week: “Trial is just all about finding out whether you and Automattic are good fits for each other so being yourself and doing your best really is the best way to just go about things.”

Week #5: Chat it up

This week was a blast. I was able to provide support through Live Chat! While the pressure is obviously on in terms of chatting live with people, I love it. I felt like I could be more genuine and offer more robust help. I learned that setting a boundary becomes a ton tougher when you are actually “on the line” with someone. I feel that live chatting is a very proactive way of supporting users and offered a better experience for them. I am a big fan of being proactive so I enjoyed this week a ton. I also think this was a perfect opportunity to really test my skills. In my mind, I felt like I rose to the challenge and was able to deliver happiness. Rather than picking and choosing tickets, it really was just random and you have to be there and find the solution. I was surprised at how engaged, complementary, and patient users have been even when I may be taking longer to look into something. I felt like I was able to get to know the “people” of WordPress better rather than just getting to know the “users” (if that makes sense). Note: I love the fact that I could be talking with people in Italy, Peru, and India all at the same time.

For feedback,  there was a focus on the concept of not just walking a user through a task but of having them do the task and you being there as “back up” . On live chat, I walked a user through how to configure a theme telling/showing her what I was doing. It ended up being too complicated and I had to send her an email with the required steps. Rather than guiding, I need to be supporting so that expectations are set.

Quote of the week: “My whole background is brought forth from the love of helping people”

Matt Chat

After the 5th week, I met with my trial leads who informed me that I made it through and they wanted to recommend me for hire for the VaultPress team. Now came the fun part… the Matt Chat. I consider myself to be a bit more patient than most about most things. As the days went by without hearing from him despite the daily pings, I fell into a calm zen like state about it. I was out to lunch with my girlfriend one day when my phone lit up “Matt: howdy”.  I didn’t even notice it until my girlfriend said something! Over a total of 6 hours, I answered and asked questions. At the very end, I was told an offer would arrive in the next couple of days. The rest is history 🙂

So, would you recommend I apply?

Contact me. I would love to talk if you are looking to put in an application. I absolutely love it here. If you can handle remote work and enjoy working with brilliant, kind, and incredibly funny people, then this is the place for you. The best advice I can give you is to work in the and forums and to work for free. I helped a ton of people without compensation simply because I wanted to learn and to help.

In so many ways, this job is everything and more than I thought it would be. Read the Automattic Creed and see if it resonates with you. If you are worried about your skill level like I was, apply. Don’t stand in your way. The worst that happens is it doesn’t work out! The best that happens is you join an incredible team. To close, I have found “my people”. I have found friends in coworkers. I have found life lessons in my work. I am encouraged and enabled to learn and make me better. I am accepted for who I am and couldn’t be happier that this job doesn’t feel like one.

“Be the one who nurtures and builds. Be the one who has an understanding and a forgiving heart – one who looks for the best in people. Leave people better than you found them.”- Marvin J. Ashton


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