Sh*t my brain says and forgets about

Farewell, Automattic!

On April 3, 2013, I was sitting in the #devmke Freenode IRC channel talking to other developers in the Milwaukee (Wisconsin, USA) area. I saw a conversation about one of the people working from home and thought, what an incredible place this must be to work! For some reason, I had heard the name Automattic before – and after landing on the homepage, I realized why! It was because of WordPress and specifically signing up for WordPress.com to get an Akismet API key to prevent comment spam. When I saw a Mobile Wrangler job posting, I immediately applied. I got the offer in May and started near the end of July 2013.

Without really exaggerating, working remotely at Automattic has literally saved my life. I’ve learned more about how my mind works, how I approach work, what relationships mean to me, and what value I can bring to an interaction. I’ve learned how to lead like Aaron, embracing my own unique style of seeing the universe and helping inspire others to connect and create outcomes.

Every year (pre-pandemic), every Automattician would get together in one location for a week – called the Grand Meetup. My heart is sad that I won’t be at the next Grand Meetup. That annual event has created some of the fondest memories of my entire life. I’ve become friends with people that I still have yet to actually work with directly. That’s the power of the system there – we value our connections over the work. With those connections, we overlay the work after. I can’t tell you how many times I’ve turned those lunchtime conversations at the GM into conduits to get things done later. Meetups are critical to Automattic’s success.

DJing @ the 2016 GM – photo by clickysteve

Some of the highlights of my time at Automattic was with helping organize several of the Automattic Grand Meetup closing parties. In 2015 it was with the first Automattic band performance and the Jane Doze DJing, 2016 with a coworker and me DJing, and 2017 with MICK DJing. This all came from me plugging my phone into the PA system of the dinner tent in 2014, playing some of my favorite songs. Our favorite Chief of Staff, Rose, noticed everyone enjoying themselves and pinged me to help out in the following years. Little did I know that I would be negotiating performance contracts and coordinating an audio and lighting production crew in the next months. What a rush. Seeing the look on Matt’s (the CEO) face walking into the ballroom before we opened the doors in 2015 was the best payoff ever.

Trying out the photo booth before the 2015 GM

For the last four and a half years I’ve been leading the Woo Mobile product teams, and it has been a joy. I started the team with just one other person and grew it into the group of 30+ people it is today. Mentoring & coaching four leads made me see how I could be a better engineering lead. I also got a chance to develop product management skills, wearing multiple hats. I’m so proud of everyone on the team (and everyone else we’ve worked with!) for getting the product to where it is today. I feel like I am leaving at a high point in my career there. Nine years will have been the longest I’ve ever been at a place before.

Automattic has been a great home for me and has helped me through a lot of bad times and given me a lot of good times. It wasn’t my intention to find a different place to work. I started looking at other companies for inspiration on defining my role better and for seeing where I should aim my career at. The side effect of that research was a little spark of excitement forming to try something different. Life is too short to not take some risks once in a while.


My last day at Automattic was Friday, June 3. I spent the last couple of weeks passing the baton off to a teammate and getting as much as I could out of my head for others. I had 1:1s with my boss, my team leads, and other Automattic employees wanting to say goodbye.

Those two weeks were tremendous in helping me process my exit. I posted my farewell notice, told the team, turned in my hardware, filled out the exit survey, had a final 1:1 with my HR rep, DJed one final Friday jam session, and then attended a farewell Zoom I planned. My team put together a very thoughtful farewell video and organized a couple gifts for me which were amazing. I definitely felt the warm fuzzies and the sense of loss we all were feeling. What a great group of humans! 🥰

I didn’t stick around for my access to get cut in Slack – it was already an emotional day and waiting for that felt unnecessary. I walked away from my last day feeling a bit lonely which is certainly an artifact of not being in an office with other humans.

The departure process at Automattic felt anticlimactic. I’m not sure what else I had expected to happen, honestly. They celebrate new hires, new houses, new partners, and new babies, but don’t really celebrate someone leaving at a company level. My farewell post had a LOT of heartfelt goodbyes and the process of reading and replying to them was cathartic. It helped me recognize my true impact on the company by hearing the stories of how I’ve helped shape the culture there and affected so many lives. That was priceless.


On the exit survey, Automattic asks “would you consider ever coming back to work at Automattic?”. I answered truthfully:

Yes.

What’s next? More details to come. 🤫

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5 Comments

  1. Cindy

    Wonderful writeup!!! Wishing you all the positive energy towards your new venture!!! Xoxo

  2. Not gonna lie, felt weird coming back from WCEU and not having you in the channel 🙁

  3. >On the exit survey, Automattic asks “would you consider ever coming back to work at Automattic?”. I answered truthfully: Yes.

    Me too, without any hesitation

  4. You’re an inspiration, Aaron! I’m sad I missed your sendoff since I was AFK that week, so I’m glad I could reach out here. Although we never worked together directly, I know your presence has had such a positive effect on the company. You will be sorely missed, but I wish you all the best! 💛

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