My 10-step path to becoming a remote data scientist with Automattic

About two years ago, I read the book The Year without Pants, which describes the author’s experience leading a team at Automattic (the company behind WordPress.com, among other products). Automattic is a fully-distributed company, which means that all of its employees work remotely (hence pants are optional). While the book discusses some of the challenges of working remotely, the author’s general experience was very positive. A few months after reading the book, I decided to look for a full-time position after a period of independent work. Ideally, I wanted a well-paid data science-y remote job with an established distributed tech company that offers a good life balance and makes products I care about. Automattic seemed to tick all my boxes, so I decided to apply for a job with them. This post describes my application steps, which ultimately led to me becoming a data scientist with Automattic.

Before jumping in, it’s worth noting that this post describes my personal experience. If you apply for a job with Automattic, your experience is likely to be different, as the process varies across teams, and evolves over time.

📧 Step 1: Do background research and apply

I decided to apply for a data wrangler position with Automattic in October 2015. While data wrangler may sound less sexy than data scientist, reading the job ad led me to believe that the position may involve interesting data science work. This impression was strengthened by some LinkedIn stalking, which included finding current data wranglers and reading through their profiles and websites. I later found out that all the people on the data division start out as data wranglers, and then they may pick their own title. Some data wranglers do data science work, while others are more focused on data engineering, and there are some projects that require a broad range of skills. As the usefulness of the term data scientist is questionable, I’m not too fussed about fancy job titles. It’s more important to do interesting work in a supportive environment.

Applying for the job was fairly straightforward. I simply followed the instructions from the ad:

Does this sound interesting? If yes, please send a short email to jobs @ this domain telling us about yourself and attach a resumé. Let us know what you can contribute to the team. Include the title of the position you’re applying for and your name in the subject. Proofread! Make sure you spell and capitalize WordPress and Automattic correctly. We are lucky to receive hundreds of applications for every position, so try to make your application stand out. If you apply for multiple positions or send multiple emails there will be one reply.

Having been on the receiving side of job applications, I find it surprising that many people don’t bother writing a cover letter, addressing the selection criteria in the ad, or even applying for a job they’re qualified to do. Hence, my cover letter was fairly short, comprising of several bullet points that highlight the similarities between the job requirements and my experience. It was nothing fancy, but simple cover letters have worked well for me in the past.

⏳ Step 2: Wait patiently

The initial application was followed by a long wait. From my research, this is the typical scenario. This is unsurprising, as Automattic is a fairly small company with a large footprint, which is both distributed and known as a great place to work (e.g., its Glassdoor rating is 4.9). Therefore, it attracts many applicants from all over the world, which take a while to process. In addition, Matt Mullenweg (Automattic’s CEO) reviews job applications before passing them on to the team leads.

As I didn’t know that Matt reviewed job applications, I decided to try to shorten the wait by getting introduced to someone in the data division. My first attempt was via a second-degree LinkedIn connection who works for Automattic. He responded quickly when I reached out to him, saying that his experience working with the company is in line with the Glassdoor reviews – it’s the best job he’s had in his 15-year-long career. However, he couldn’t help me with an intro, because there is no simple way around Automattic’s internal processes. Nonetheless, he reassured me that it is worth waiting patiently, as the strict process means that you end up working with great people.

I wasn’t in a huge rush to find a job, but in December 2015 I decided to accept an offer to become the head of data science at Car Next Door. This was a good decision at the time, as I believe in the company’s original vision of reducing the number of cars on the road through car sharing, and it seemed like there would be many interesting projects for me to work on. The position wasn’t completely remote, but as the company was already spread across several cities, I was able to work from home for a day or two every week. In addition, it was a pleasant commute by bike from my Sydney home to the office, so putting the fully-remote job search on hold didn’t seem like a major sacrifice. As I haven’t heard anything from Automattic at that stage, it seemed unwise to reject a good offer, so I started working full-time with Car Next Door in January 2016.

I successfully attracted Automattic’s attention with a post I published on the misuse of the word insights by many tech companies, which included an example from WordPress.com. Greg Ichneumon Brown, one of the data wranglers, commented on the post, and invited me to apply to join Automattic and help them address the issues I raised. This happened after I accepted the offer from Car Next Door, and hasn’t resulted in any speed up of the process, so I just gave up on Automattic and carried on with my life.

💬 Step 3: Chat with the data lead

I finally heard back from Automattic in February 2016 (four months after my initial application and a month into my employment with Car Next Door). Martin Remy, who leads the data division, emailed me to enquire if I’m still interested in the position. I informed him that I was no longer looking for a job, but we agreed to have an informal chat, as I’ve been waiting for such a long time.

As is often the case with Automattic interviews, the chat with Martin was completely text-based. Working with a distributed team means that voice and video calls can be hard to schedule. Hence, Automattic relies heavily on textual channels, and text-based interviews allow the company to test the written communication skills of candidates. The chat revolved around my past work experience, and Martin also took the time to answer my questions about the company and the data division. At the conclusion of the chat, Martin suggested I contact him directly if I was ever interested in continuing the application process. While I was happy with my position at the time, the chat strengthened my positive impression of Automattic, and I decided that I would reapply if I were to look for a full-time position again.

My next job search started earlier than I had anticipated. In October 2016, I decided to leave Car Next Door due to disagreements with the founders over the general direction of the company. In addition, I had more flexibility in choosing where to live, as my personal circumstances had changed. As I’ve always been curious about life outside the capital cities of Australia, I wanted to move away from Sydney. While I could have probably continued working remotely with Car Next Door, I felt that it would be better to find a job with a fully-distributed team. Therefore, I messaged Martin and we scheduled another chat.

The second chat with Martin took place in early November. Similarly to the first chat, it was conducted via Skype text messages, and revolved around my work in the time that has passed since the first chat. This time, as I was keen on continuing with the process, I asked more specific questions about what kind of work I’m likely to end up doing and what the next steps would be. The answers were that I’d be joining the data science team, and that the next steps are a pre-trial test, a paid trial, and a final interview with Matt. While this sounds straightforward, it took another six months until I finally became an Automattic employee (but I wasn’t in a rush).

☑️ Step 4: Pass the pre-trial test

The pre-trial test consisted of a data analysis task, where I was given a dataset and a set of questions to answer by Carly Stambaugh, the data science lead. The goal of the test is to evaluate the candidate’s approach to a problem, and assess organisational and communication skills. As such, the focus isn’t on obtaining a specific result, so candidates are given a choice of several potential avenues to explore. The open-ended nature of the task is reminiscent of many real-world data science projects, where you don’t always have a clear idea of what you’re going to discover. While some people may find this kind of uncertainty daunting, I find it interesting, as it is one of the things that makes data science a science.

I spent a few days analysing the data and preparing a report, which was submitted as a Jupyter Notebook. After submitting my initial report, there were a few follow-up questions, which I answered by email. The report was reviewed by Carly and Martin, and as they were satisfied with my work, I was invited to proceed to the next stage: A paid trial project.

👨‍💻 Step 5: Do the trial project

The main part of the application process with Automattic is the paid trial project. The rationale behind doing paid trials was explained a few years ago by Matt in Hire by Auditions, Not Resumes:

Before we hire anyone, they go through a trial process first, on contract. They can do the work at night or over the weekend, so they don’t have to leave their current job in the meantime. We pay a standard rate of $25 per hour, regardless of whether you’re applying to be an engineer or the chief financial officer.

During the trials, we give the applicants actual work. If you’re applying to work in customer support, you’ll answer tickets. If you’re an engineer, you’ll work on engineering problems. If you’re a designer, you’ll design.

There’s nothing like being in the trenches with someone, working with them day by day. It tells you something you can’t learn from resumes, interviews, or reference checks. At the end of the trial, everyone involved has a great sense of whether they want to work together going forward. And, yes, that means everyone — it’s a mutual tryout. Some people decide we’re not the right fit for them.

The goal of my trial project was to improve the Elasticsearch language detection algorithm. This took about a month, and ultimately resulted in a pull request that got merged into the language detection plugin. I find this aspect of the process pretty exciting: While the plugin is used to classify millions of documents internally by Automattic, its impact extends beyond the company, as Elasticsearch is used by many other organisations and projects. This stands in contrast to many other technical job interviews, which consist of unpaid work on toy problems under stressful conditions, where the work performed is ultimately thrown away. While the monetary compensation for the trial work is lower than the market rate for data science consulting, I valued the opportunity to work on a real open source project, even if this hadn’t led to me getting hired.

There was much more to the trial project than what’s shown in the final pull request. Most of the discussions were held on an internal project thread, primarly under the guidance of Carly (the data science lead), and Greg (the data wrangler who replied to my post a year earlier). The project was kicked off with a general problem statement: There was some evidence that the Elasticsearch language detection plugin doesn’t perform well on short texts, and my mission was to improve it. As the plugin didn’t include any tests for short texts, one of the main contributions of my work was the creation of datasets and tests to measure its accuracy on texts of different lengths. This was followed by some tweaks that improved the plugin’s performance, as summarised in the pull request. Internally, this work consisted of several iterations where I came up with ideas, asked questions, implemented the ideas, shared the results, and discussed further steps. There are still many possible improvements to the work done in the trial. However, as trials generally last around a month, we decided to end it after a few iterations.

I enjoyed the trial process, but it is definitely not for everyone. Most notably, there is a strong emphasis on asynchronous text-based communication, which is the main mode by which projects are coordinated at Automattic. People who don’t enjoy written communication may find this aspect challenging, but I have always found that writing helps me organise my thoughts, and that I retain information better when reading than when listening to people speak. That being said, Automatticians do meet in person several times a year, and some teams have video chats for some discussions. While doing the trial, I had a video chat with Carly, which was the first (and last) time in the process that I got to see and hear a live human. However, this was not an essential part of the trial project, as our chat was mostly on the data scientist role and my job expectations.

⏳ Step 6: Wait patiently

I finished working on the trial project just before Christmas. The feedback I received throughout the trial was positive, but Martin, Carly, and Greg had to go through the work and discuss it among themselves before making a final decision. This took about a month, due to the holiday period, various personal circumstances, and the data science team meetup that was scheduled for January 2017. Eventually, Martin got back to me with positive news: They were satisfied with my trial work, which meant there was only one stage left – the final interview with Matt Mullenweg, Automattic’s CEO.

👉 Step 7: Ping Matt

Like other parts of the process, the interview with Matt is text-based. The way it works is fairly simple: I was instructed to message Matt on Slack and wait for a response, which may take days or weeks. I sent Matt a message on January 25, and was surprised to hear back from him the following morning. However, that day was Australia Day, which is a public holiday here. Therefore, I only got back to him two hours after he messaged me that morning, and by that time he was probably already busy with other things. This was the start of a pretty long wait.

⏳ Step 8: Wait patiently

I left Car Next Door at the end of January, as I figured that I would be able to line up some other work even if things didn’t work out with Automattic. My plan was to take some time off, and then move up to the Northern Rivers area of New South Wales. I had two Reef Life Survey trips planned, so I wasn’t going to start working again before mid-April. I assumed that I would hear back from Matt before then, which would have allowed me to make an informed decision whether to look for another job or not.

After two weeks of waiting, the time for my dive trips was nearing. As I was going to be without mobile reception for a while, I thought it’d be worth letting Matt know my schedule. After discussing the matter with Martin, I messaged Matt. He responded, saying that we might as well do the interview at the beginning of April, as I won’t be starting work before that time anyway. I would have preferred to be done with the interview earlier, but was happy to have some certainty and not worry about missing more chat messages before April.

In early April, I returned from my second dive trip (which included a close encounter with Cyclone Debbie), and was hoping to sort out my remote work situation while completing the move up north. Unfortunately, while the move was successful, I was ready to give up on Automattic because I haven’t heard back from Matt at all in April. However, Martin remained optimistic and encouraged me to wait patiently, which I did as I was pretty busy with the move and with some casual freelancing projects.

💬 Step 9: Chat with Matt and accept the job offer

The chat with Matt finally happened on May 2. As is often the case, it took a few hours and covered my background, the trial process, and some other general questions. I asked him about my long wait for the final chat, and he apologised for me being an outlier, as most chats happen within two weeks of a candidate being passed over to him. As the chat was about to conclude, we got to the topic of salary negotiation (which went well), and then the process was finally over! Within a few hours of the chat I was sent an offer letter and an employment contract. As Automattic has an entity in Australia (called Ausomattic), it’s a fairly standard contract. I signed the contract and started work the following week – over a year and a half after my initial application. Even before I started working, I booked tickets to meet the data division in Montréal – a fairly swift transition from the long wait for the final interview.

🎉 Step 10: Start working and choose a job title

As noted above, Automatticians get to choose their own job titles, so to become a data scientist with Automattic, I had to set my job title to Data Scientist. This is generally how many people become data scientists these days, even outside Automattic. However, job titles don’t matter as much as job satisfaction. And after 2.5 months with Automattic, I’m very satisfied with my decision to join the company. My first three weeks were spent doing customer support, like all new Automattic employees. Since then, I’ve been involved in projects to make engagement measurement more consistent (harder than it sounds, as counting things is hard), and to improve the data science codebase (e.g., moving away from Legacy Python). Besides that, I also went to Montréal for the data division meetup, and have started getting into chatbot work. I’m looking forward to doing more work and sharing my experience here and on data.blog.