Pierre's journal

Cromulon, bug crafter.

Three amazing years

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For the past three years, I have been working at Automattic on exciting projects, surrounded by smart and caring people.

I’m now moving on to the unknowns; I just left the best job I ever had.

This post is meant as a reminder to me, while my memory’s fresh, but also as a piece of documentation around my work and experience with this company, that’ll live somewhere in a dark corner of The Internets, forever.

Addressing the elephant in the room

Yes, I left because of the recent events and took Matt’s offer. However, I’m leaving with no hard feelings, only good memories.

I’m in no place to judge Matt’s and Automattic’s business actions; I neither agree nor disagree; I’m not even qualified enough to discuss it (and I wouldn’t anyway).

I just felt saddened and hurt by the polarization of people, and the “with me or against me” war rhetoric.

I’m not with nor against anyone; I was living the dream, sharing the values of humanity, excellence, dedication and growth; it kind of blew the party for me, and I disagree with the way the issue is currently being handled and communicated.

Don’t get me wrong, I would have been sad in silence while (hopefully) still being employed, if this offer weren’t on the table, but, faced with the certainty in a context where I felt unsafe, I preferred to leave in peace, while not having to intrinsically validate something I was not even remotely involved in.

If you’d like to know more about the events, here are some articles from different media covering them:

My work there

From the very first day, I was part of a small team dedicated to building, reviving and maintaining a diverse set of satellite products.

We were a company within the company; actually, we were seven companies inside the company.

Here is a list of all the products we had, at the time, under our umbrella:

Our main focus when I joined was a service called VideoPress.

To make a long story short, it used to “just” be the video platform for WordPress.com, a thing in the dark allowing people to upload and stream videos, and we made it a cool product.

The biggest achievements I could think about:

  • We built a solid transcoding pipeline: when a video gets in, we extract information, analyze it, do some stuff with it, and create a bunch of other videos in different formats. That’s basically what you usually pay Google or Amazon for, and we did that ourselves (we still paid Google for some very specific transcodes, though, just to skip on having in-house GPU servers dedicated to this very specific task).
  • We built the best in-browser video player on top of video.js.
  • We built automated content analysis to detect problematic content, respecting privacy while keeping the platform safe.
  • We went from 0 to 1 (I guess, to 0.99) on a whole new product, based on the VideoPress experience. Unfortunately, it never saw the light of day for internal reasons, but we were all proud of what we had and excited to use it.

During the “VideoPress era”, we got to experiment, improve, and iterate on something used by millions of daily users; we pushed ourselves every single day, getting out of our comfort zone, learning (please take a moment to acknowledge our pain when browsing ffmpeg’s documentation), sharing, and improving the user experience with video uploading and streaming.

We also regularly did “sweeps” on our other projects, the most impactful being a refresh/redesign of the Gravatar profile page during a team meetup.

Then Gravatar became a bet again, moving to a dedicated team to support it (check out all the new cool things they have there if you haven’t; it’s worth it!).

After the “VideoPress era”, we merged another team into ours, a bunch of other products too, and my role changed to a leadership role.

Changelog for this event:

It was quite a big challenge.

I had to find my path through leadership, while integrating new members and big and impactful products.

I think if it were anywhere else than Automattic, it would even look like a recipe for failure.

But it wasn’t; I was lucky enough to be supported by my team, my previous lead (and mentor, and friend), my division lead, and my HR representative (HRW, with the W for “Wrangler”) during this transition period.

One of my first tasks was to rebuild the team, and provide clarity on the direction we were leading towards.

I learned about the stages of team development while experiencing them. We went through all the phases, by the book, and I was glad I had external help to make me realize it, reflect on it, and improve or adjust my leadership style.

We had big plans set, and started working on them, improving the user experience and traction on Crowdsignal and WP Job Manager.

During a board meeting with Matt and Toni, we decided to dedicate most of our resources to revive Cloudup, a product created by Guillermo Rauch, and acquired by Automattic in 2013.

The product was already in our team, but it’s been in maintenance mode for a while.

The users, and Matt, loved this product, so he asked me for a roadmap, I sent one, and I received the best message you could possibly receive from him, something like “Plan looks good 👍”.

We then started the “Cloudup era”, with the mission to rebuild Cloudup from the ground up, keeping its spirit while (drastically) improving the user experience.

With a clear roadmap, clear goals, and a startup spirit, we created the best product we could create (it should be released this year, add yourself to the waitlist).

While being hands-on, I think one of my biggest achievements here, as a leader, was to make the team, and the whole company, excited about a product we all thought was dead, late to the party, and in a crowded market.

It isn’t, I believed it, and I still believe it.

The “new” Cloudup brings something to the table that no other, big or small, players bring.

During my last couple of months at Automattic, I’ve also been surrounded by talented people across our division, and Adii also entered the game, stepping up our customer orientation and focus on delivery.

With a demo ready, my last board meeting had Guillermo as a guest.

I was expecting him to “barely like it”, it was his product after all, but he was pretty excited about it, being impressed by the huge improvements we added, and sharing a lot of positivity, as well as things he would have liked to add at the time.

With this achievement in mind, the team was pumped to run the last mile.

I took a bunch of (long overdue) AFKs (vacations), then I had a Reboot leadership training to attend, which I postponed for about a year.

While I was expecting the Reboot training to be something pretty generic (and maybe even boring), it was an incredible experience; It was mostly about reflecting and sharing with peers across Automattic, while providing us tools to be a better leader, and a better person.

I spent a week there, with about 15 other talented and inspiring Automatticians.

The week after was my last week at Automattic.

The people there

There’s probably no word to describe it.

What you can read on the internet most likely reflects it better than I could describe it.

I met hundreds of people, virtually or physically, from different countries, cultures, motivations, spectrums, or whatever could make people different.

They were all working at the same place, sharing the same values, agreeing or disagreeing, and it just works.

The hiring process is probably one of the reasons it “just works”, while, of course, you can sometimes end up with people not really fitting at the end of the process, I would say it’s marginal, and the percentage of them staying is probably even more marginal.

As stated earlier, I’ve been in the same team, from the very first day.

Before I started, I was asked questions about what I’d like to do and who I am, I’ve been matched with people who ended up becoming friends, and projects so diverse that my natural tendency to get bored fast was easy to overcome.

During the first “iteration” of the team, we were the four of us, communicating naturally, working together and supporting each other, while understanding exactly what the others were doing, and achieving the impossible.

I went to several division meetups, and got to meet the people behind the screen, reinforcing the link between us, and creating new ones.

Each individual I interacted with had a long-lasting effect on me, and I feel I’ve grown to become a better person, thanks to them.

When I transitioned to a leadership role, I was never alone.

I had people around me, with whom I could openly and honestly discuss, supporting my growth, while respecting (and sometimes defending) my individuality and leadership style.

I had a division lead that trusted me, and could take (virtual) bullets for me, enabling me to provide the best version of myself for the team, and the whole company.

In my biggest moments of doubt, I received a lot of positive feedback from my team, helping to overcome the “down” periods.

Again, I could not describe it, it just is what it is, Automattic is not just a brand or company, it’s the sum of the outstanding individuals there.

I’m also thankful that my role led me to meet and interact with “big guns”, all the name-dropping in the previous section being a portion of them. They taught me a lot about several aspects of a huge business or company, the humans behind it, and leadership.

Final thoughts

Some random notes, brain to keyboard, in no particular order:

  • It hurts to leave, I cared, and still care a lot for Automattic; it was probably the right decision, for me, but it doesn’t make it any easier.
  • I’ve been working remotely for the past decade now, working at Automattic exponentially improved my capacity at doing it properly.
  • Out of my comfort zone pretty much every single day, but it always felt good (I think it felt good because the environment made it safe, it’s not just a dumb motivational statement like “DO BETTER IT’S BETTER”).
  • I started unlocking some coaching and mentoring skills I never thought I could have, thanks to the learning environment we have there.
  • I felt like a startup CEO every single day, without having to worry about the money, which helped us achieve the impossible.
  • [[some other things may or may not appear there]]

What’s next?

I don’t know.

I’d like to continue my journey in leading innovation, fostering excellence and human growth, all while creating a safe and thriving environment for a team or a company.

If you know or have a company with a similar environment (or with a strong “people first” commitment), I’d love to hear from you.

I also now have a bit of time to reflect and experiment, and that might also plant some seeds.

I’ll also probably remove the dust from this blog. Part of the work at Automattic was to write P2 posts, so I’m getting used to that, and I’d like to document a bit more of my life and journey.

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