Switching jobs and applying for Automattic

A home office, featuring a wooden desk, laptop, monitor, table lamp, and a pot plant.

Here’s the story of how I came to join Automattic, the parent company of WordPress.com, working as a JavaScript Engineer. Automattic is a fully distributed company of 900+ people from 70 countries, with all employees working from their homes, home offices, co-working spaces, cafes, or in some cases houseboats. Really wherever suits you to do good work.

I have a personal principle I try to go by, which is that in any given six month period, it’s best not to make more than one big life change. If you change jobs, move house, or do any other life changing thing that you might experience as positive or negative, or a mix of the two, try to give yourself some breathing room before doing the next thing.

I tend to be way more conservative than that, and when it comes to switching jobs, over the past decade, I’ve only done it once every four years or so. From finishing university in 2007 to this year, I only worked in two different workplaces. If I’m in a good place, I like to stay put!

Thinking of changing jobs

For the past eleven years, I worked at ACMI, a film museum in Melbourne. (Also videogames, art, and digital culture, but the shorthand film museum tends to be easier to get the idea across). I joined when I was 24, working in customer service before moving on to ticketing. I supervised in ticketing for a few years, before moving over to a web developer role for another four years. It was a fascinating place to work, but calling the job interesting or good is kind of hard, because it feels like trying to describe or explain a decade of your life. For most of that time I couldn’t really imagine working anywhere else. It was a cool museum, what they were trying to do aligned with my interests (the intersection of education, creative industries, and presenting moving image works and exhibitions to audiences), I got to work on some really fun and creative projects, and they also sent me to some rad conferences!

In my spare time, I’d been working with the novelist Anna McIlwraith on her book releases and website, and I started to get a feel for the sheer variety of communities that utilise WordPress. Then, I happened to read about Automattic open sourcing the Calypso editor for WordPress.com. It planted a seed in my mind that one day I would love to work on problems that weren’t just for a single institution, but instead contributed to a broader platform that helps many, many users build websites, tell stories, sell books, or otherwise share their work.

While I loved working at ACMI, and would often say that it’s the only place in Melbourne where I could really see having a fulfilling career, I started to feel that one day I’d like to take the leap and try something new. I also loved the idea of working remotely and decoupling where I live from where I work. And I’m certainly not the only one! A recent Digital Ocean survey found that for a lot of developers, remote work is the new normal.

Hiring practices

I’m giving you an idea of how I felt about my old job, because I think it’s interesting context for applying for this particular job, and the interview process that followed.

In the Arts / state government agencies, where I previously worked up until this point in my life, hiring was a fairly straightforward if bureaucratic process. A hiring manager would put together a position description and organise with HR to define the role, somewhere along the way there’d be budget approval to recruit, and the position would be advertised on the website along with key selection criteria. Applications were reviewed by these key selection criteria, and applicants would be short-listed for a set of 1 hour interviews. You’d interview maybe 5 or 6 people, with a panel of 3 to 4 staff doing the interviewing and, based on behavioural questions and possibly a presentation by the candidate, the interviewee would be ranked and a successful candidate would be given an offer.

It always felt like a somewhat flawed process. The interview process could feel artificial, and you really can’t tell that much about someone in just an hour, but we tried to make the best of it. We’d try to think of the best questions to ask, try to genuinely see what someone might be like to work with, and get a sense of their experience, but it was difficult. From both sides, either as a candidate, or as the person hiring, it feels like a bit of a risk to switch jobs or hire someone based on meeting them for only one hour.

And for me, thinking about leaving a workplace that I loved and a place I’d worked for eleven years, I couldn’t imagine interviewing for one hour and feeling like I had enough information to commit to leaving a really great job.

Applying for Automattic

All this is to give you some context for why I appreciated Automattic’s longer than usual hiring process, and why it was really good for someone in my position where I was cautious about switching jobs.

I applied in December of 2018 a week or so before Christmas, following the instructions on the Work With Us page especially carefully, and heard back a few weeks later in January by email, with an invitation to book in for a 90 minute interview by text chat.

A couple of weeks later, they invited me to join their Slack as a single-channel guest, and it was time for the interview! It started off with a bit of getting to know each other, and then into questions about my experience and how I approached different technical problems, but it was by no means a dreaded technical interview, there was no live coding or whiteboard-like brain teasers, just some good, well-structured questions. And the second half of the interview I had heaps of time to ask all the questions I liked, about company culture, communication in a distributed organisation across timezones, and how they manage deployments at such a large scale. Interviews can be intimidating, but I really enjoyed this one, and it was wonderful getting to hear all about the company and the sorts of challenges for new hires (like making sure to switch off at the end of the day, and not just keeping on working because you can and you’re at home).

The next day, I heard back by email that they’d like to move me to the next stage in the process, the coding exercise. You’re given a week to do it, but the idea is that you spend 4–6 hours in your spare time on the tasks. It’s designed to be something you can do in your spare time, in the way that you might actually work on a coding problem, instead of the pressure of testing your coding skills in an artificial environment like an interview. For me, a take-home coding exercise is so much more preferable to having to come up with code solutions in the moment, or endure a full day of interviews. I took around eight hours over the course of the week, but the first two were just to look over the code and tasks and make sure I fully understood what was expected of me. The people doing the hiring were also super flexible, and flagged that if you’re busy or have other commitments, you can take longer than the week.

The coding exercise was all done in Github, with my changes submitted as pull requests, and by the end of the week I’d submitted my proposed changes. I got some feedback, and there were a couple of small things that I’d missed. After fixing up those issues and submitting further changes, they recommended me for the next stage in the process, a trial project with the company!

The trial project

Throughout the hiring process, all communication was done in Slack on the same channel I’d done my initial interview. And at each stage, more staff would join the channel and I’d get to ‘meet’ them, with a different staff member leading that part of the hiring process. The effect is that you feel like you gradually get to know them, and they get to know you. And because you’re all on the one Slack channel, it’s all one big discussion.

If you’ve read any other stories of people joining Automattic, you might have heard about the trial projects. The purpose behind the trial project is to give both you and the company the experience of working with each other, on a close-to-real-but-not-quite project so that you can mutually get a good feeling for what it’d be like to work together. It’s paid, at a flat rate for everyone that has no bearing on what your future salary might be. For someone like me who was feeling very cautious about the risk of changing jobs, this was an ideal way to confirm that Automattic would be my dream place to work like I’d hoped.

By this point in the process, they give you access to their internal resources and systems, like the Automattic Field Guide where you can read more about the company and all the myriad projects, and watercooler and developer channels on Slack. To help give a better sense of what it’s like to work and ‘hang out’ with coworkers, they also added me to a Slack channel with other people doing their trial projects at the same time, where we could chat, introduce ourselves, and generally empathise with each other through the challenging, exciting, and slightly anxiety inducing process of getting to work with the company. They went to great lengths to contextualise that chatting with others doing their trial was all about getting to know each other, and it was by no means a competition. For me, this was in stark contrast to any other hiring experience I’ve had, where you really feel like you’re vying for a very limited pool of jobs.

Here, it felt like everyone in the hiring process was there to help, and each of them wanted to see us succeed. By the time you’re doing a trial project, it’s pretty clear that they’ve invested time in you, just as you’ve invested time in them, and you’re all hoping you’ll be a good fit.

I can’t say too much about the trial project itself, just that it’s designed to take roughly 40 hours, and you can take as long or as short a time as you need to do it. Some people work on it in the evenings, or just on weekends, and do a different amount of time on it each week. The people hiring consistently acknowledge that it’s a big commitment to take this on; they know people already have jobs! They genuinely want to make sure it isn’t too disruptive to your personal life. I was in a really fortunate position to be able to spend my evenings and weekends on the project, which isn’t something everyone is able to do.

I averaged working on the trial project for around 8–10 hours a week, with a little bit of work in the evenings, but mostly working on it at the weekends. Although it was pretty nerve-wracking, it was fun and interesting, too. It involved not only writing code, but also writing up architectural ideas and working closely with my hiring lead and code reviewers in implementing their feedback, or going in a different direction.

Wrapping up the trial and joining the company

My trial project wrapped up after around a month, and they recommended me to the CEO for a full-time role. Not too long after that, someone from HR got in touch to schedule a chat, where we discussed the trial project, I had an opportunity to ask more questions, and confirmed that I’d be happy travelling 2–3 weeks a year internationally for company meetups, and we discussed compensation and a starting date. Later that day, they sent me an offer letter, and after celebrating that weekend, I then faced the daunting prospect of resigning from a job that I loved so that I could begin a new chapter in my life in a new job that I would also love! (Please forgive me if it is sickening to read how much I’ve enjoyed my jobs, I have been stupendously lucky to get to work at some wonderful places.)

Having worked in the one place for 11 years, I’ve very rarely resigned jobs, and switching jobs, even when it’s for a good reason, is an incredibly stressful thing to do. I gave as much notice as I could to do a decent handover, and also give myself a couple of weeks downtime to prepare for the new role. It sounds odd to say, but I’m so grateful for the long and involved hiring process with Automattic, because it allowed me to process at each step of the way the gravity of the situation in contemplating switching jobs, and it allowed me to evaluate what the change would be like for me at the same time as them seeing what I would be like to work with. Through the trial process at Automattic, I became fully certain that I would love remote-life and that this would be a place where I could grow and learn for many years to come.

It was painful and difficult leaving my old job, and I miss my old colleagues dearly, but I’m so glad I took the chance, applied, and gave the hiring process my best shot. I have been happily working at Automattic for a couple of months now, I’ve gotten to know my new colleagues who are based all around the world, and while I’m still very new to the company, and there is just so much to learn, I couldn’t be more excited or happy to be working there.

Thanks for reading! Applying for jobs is hard, and going through interview processes is hard, and changing jobs is hard, too! But Automattic do a pretty great job of making it a respectful process for all parties, and have built a really unique fully-distributed work culture, and build great products to boot! If working there sounds interesting to you, I’d recommend taking a look at the currently open positions on their website, and then have a listen to the CEO, Matt Mullenweg‘s podcast Distributed, particularly the episode where he talks about founding Automattic, distributed work, and the future of the company.