Automattic is one of those companies that you've definitely encountered in your time on the Internet but you may have never heard of them. If you've ever used a WordPress site (or built one), Tumblr, Gravatar, or WooCommerce, you've used an Automattic product. It wasn't until maybe early 2025 that I realized I had been using Automattic products all my life, with my most recent fascination being with Pocket Casts (following their acquisition by Automattic).

Given my foundational programming experience is with PHP (although I use, and usually prefer, many other languages now), I genuinely use or have used their products, and my location and living situation necessitate a worldwide remote role, I tried applying for the Experienced Software Engineer position on September 9, 2025.

And was rejected on September 9, 2025.

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Only joking. Well the rejection part isn't a joke. I had reached out to someone on LinkedIn prior to the rejection to let them know about my candidacy and talk tech. After I let them know I had been rejected, I was told Automattic was focused on hiring at the principal level and that may have been the reason for my rejection. This was also soon following their restructuring, so maybe it was just bad timing.

A few months later, I saw a new job posting for an applied AI engineer position. All of my work in the past few years has been leading AI initiatives at companies, building out AI infrastructure, and serving as the springboard for client-facing AI features to encourage engineers to seek ways to benefit clients using AI, so I thought it would be a perfect fit. I applied again on January 30, 2026 and received the first contact email on March 14. A bit slower this time for sure. I had almost forgotten about the application at this point.

Screening

I scheduled a video interview over Zoom with a recruiter for March 18. This was a 45-minute informal chat (or as informal as a formal recruitment process can be, of course) about my experience, the team I was applying for, and Automattic in general. One interesting thing I've gathered from reading about Automattic's hiring process is that they generally don't recruit for specific teams (hence "Experienced Software Engineer" rather than any specific domain), but this position was for a very specific, nascent team looking to lead AI initiatives across Automattic's suite. The philosophy at Automattic seems to be team fluidity with team changes being normal, so I am curious if this position would differ at all. Not something I'm really concerned about since I am used to being on a team that excels in a specific domain.

After the interview, I was told I would likely hear back within a week but that the team lead was on vacation (which somehow always seems to be the case when I interview anywhere). I finally received the invitation for next steps on April 2. This included an invitation for a 90-minute Slack interview, which I've scheduled for April 8 as I write this on April 3. It also included an invitation for an aptitude test called the Criteria Cognitive Aptitude Test. This is a step I haven't seen mentioned before, although I am familiar with tests like these as I've taken the Thomas General Intelligence Assessment in the past for a different company (bonus points if you can guess which).

The first portion of the Criteria assessment comprises 50 logic questions and 15 minutes to complete them. According to them, most people do not complete all the questions, and indeed I only got to around question 46 before running out of time. After this, there are about 180 behavioral and personality questions to answer with no time limit, though the estimated time for completion is 10 minutes. These are just "strongly agree" vs "strongly disagree" questions on a scale from 1 to 5, so it's easy to breeze through them. After this, you will receive an email detailing your personality and behavioral notes, although you won't receive information about the logic portion or which questions you answered incorrectly.

Slack Interview

Getting this scheduled took a couple tries. I received an invitation to book a Slack interview, but when I clicked the link to book the interview, a time for the same day in a different time zone had already been selected and confirmed. This seemed strange, so I asked the recruiter if I had been sent someone else's link by mistake, but they assured me all was well and that I could just use the reschedule option to select a suitable time. I did so, contacted them, and did not hear back for a few days. On the day of the interview, I was informed that due to a bug the interview was not in the system and would have to be rescheduled. Fortunately, the second time around, I received a working link, received an email confirmation of the booking, and received the Slack invite to my interview channel. This interview took place on April 14, so almost one month after my initial screening.

Like many others, I had not done a text-only interview before, so it was a little bizarre to me but an interesting experience. On the candidate.fyi page (the recruiting system), there was a video about interviewing at Automattic which happened to include some details about the text interview. Unfortunately, I didn't see this video until after my Slack interview. The employee in the video mentioned not only to not type in paragraphs, but that each message should be about one sentence. I had read some other prep material that mentioned not writing long messages, but I didn't think this meant each message should only be one sentence. This is actually a pet peeve of mine in general -- I dislike when my notifications blow up because someone is sending their stream of consciousness one thought at a time -- but good to know that this is the expectation.

The interview covered questions like what my background is, my thoughts on AI, something I built that was challenging, and a few others. I felt like we covered surprisingly little in 90 minutes. Maybe that was due to my not-one-sentence-at-a-time messages, or maybe the text interviews are not really meant to be a constant back and forth.

The prep information I received did mention a 90-minute text interview is equivalent to a 60-minute video interview, but I didn't feel this was the case. Maybe closer to a 40-minute video interview. Honestly, I'm not sure which format I prefer. Maybe video, surprisingly. But it also didn't help that the interview was at 11:15 pm for me. Maybe if it were during the day and I were more awake, I would prefer text interviews.

Second Interview

Surprisingly, I was asked to join a second video interview (if you count the screening as the first). This is unusual as Automattic's process is usually screening → Slack interview → coding test → trial. The interviewer mentioned the video interview is something new they are trying. This interview took place on May 5, and it took quite a long time to hear back after my Slack interview (maybe 2.5 weeks) despite being told I would hear back within a week.

When I was originally introduced to the team via my recruiter, I was quite excited because they mentioned the Hosting Platforms division is taking their infrastructure and scaling knowledge from WordPress VIP to the rest of Automattic. My current work involves a lot of infrastructure automation for enterprise clients, so I thought this would be a good fit.

However, the interviewer was with someone on the product engineering team within the Hosting Platforms division. From what they told me, their team's work is focused on building bespoke solutions for enterprise clients. Not quite what I was expecting, but this was still interesting to me because my work leading development for an ERP system used nationwide had always been about building bespoke solutions for enterprise clients.

Still, I don't have proper "product engineering" experience as a forward-deployed engineer or working extensively with product design, UX, etc. teams. The interviewer tried to dig into my experience in this space, and unfortunately I didn't feel my background really aligned with what they were looking for. I have experience working with small design teams and with project management, but my work over the past decade has almost always been leading the implementation -- including design, gathering requirements, etc. -- from beginning to end as there had not been entire teams dedicated to UX, design, or requirements (aside from account executives).

Rejection

While I felt my previous interview was generally positive as I had the chance to speak about my decade of enterprise development experience and learn more about the VIP offering, I received the rejection notice in that my skills do not align with the product engineering expertise they are looking for. The recruiter noted my AI, backend, and infrastructure skills were highly regarded, but the lack of experience in product engineer wouldn't make me a good fit for that team.

This was not only disappointing but just confusing. Like I mentioned early in this post, Automattic's recruitment for the AI team seemed to be unique in that the team was decided upfront and they were recruiting specifically for that team. It was even communicated during my initial screening which team I would be on and who I would be working with, and that information was reflected in candidate.fyi. Despite that, at some point in my recruitment process, my recruitment switched from AI engineer to the general engineer recruitment process where the team had not yet been decided, and my candidate.fyi changed again to reflect that.

That change was never actually communicated to me at any point in the process -- it was just something I noticed silently happen. Yes, if they were actually searching for a product engineer with extensive product design cross-team coordination, I would not have applied to that role as that doesn't align with my expertise. I applied to the AI engineer role, not the product team.

So as you can imagine, it's pretty weird and disappointing to be rejected for a role you never applied to.

I felt the overall experience was good as everyone was very kind and fun to speak with, but if Automattic's hiring goals changed, or if the position I applied to had been filled or closed, I wish that would have been communicated directly. If I had known I was no longer being considered for the AI position and was instead being shifted towards product engineering, both my time and the company's time could have been saved by giving me the opportunity to reconsider my candidacy and withdraw.