This past Monday marked my five year anniversary at Automattic, working for WordPress VIP. It seems forever ago, but at 9:59AM on February 11, 2015 I emailed with my resume built as a child theme to twentyfifteen. Somehow I must have tricked them because 22 days later (which is pretty fast for a reply from Automattic back then 😬), interviewed, code tested, trialed, and ended up sticking around.

I’m not going to go through the boring details of how hiring works at Automattic. Many great friends and bloggers better than me have written about it. I would though like to highlight a few of my favorite parts of my five year journey.

The first few weeks and months were a bit surreal, trying to just get caught up to speed in the chaos. Spring turned into Summer, and I came across my first real moment of panic: Travel.

I was asked to go to New York to meet with some clients, and attend the BigWP meetup. Now, for those of you that don’t know me, I’m born and raised from Nowhere, USA where we don’t really travel much. Luckily, it ended up great! BigWP was a blast, and meeting up with coworkers in real life, traveling around NY, and visiting clients really set in stone that the work that I was doing mattered to people.

It wasn’t a month later that I was off again on another adventure: my first Grand Meetup. The Grand Meetup is the once-a-year gathering of everyone from Automattic where we teach, learn, work, play, and really connect. For being a fully distributed company, this face to face time invigorates me more than anything and gets me excited about the work we still have to do. So, in October of 2015 I went to Park City.

At that time VIP felt like a good size, and tiny in comparison to the larger company of 400 Automatticians:

Fast forward a few more months and I’m headed to my first team meetup, in Barcelona. By now, I’ve flown a few times, so I’ve got this down, but overseas, that was another frightening first.

That meetup in Barcelona, my first meetup, will have a special place in my heart forever. I don’t think anything can replace that feeling of fear, excitement, esprit de corps, and so many other emotions. From having coffee at a cafe at nearly midnight with a couple of friends just chatting about life, to actually working together to build our business plans for the year ahead–even thinking back about it now, it seems surreal.

Right. Now this was all within the first six months. At this rate, this post will end up a small book. I’ll just hit some yearly highlights


The VIP Workshop in Napa

BigWP NYC again!

Whistler Grand Meetup

2016 Election Traffic Boom, what a night!

End the year with one more BigWP


Team meetup in Glasgow

Grand Meetup in Whistler


Team meetup in Lisbon

First VIP Grand Meetup on Montreal


Client meetings in San Francisco

Team meetup in Playa del Carmen

Client meetings in New York

VIP Grand Meetup in Rotterdam


Team meetup in Athens

While I love the work that I do, and I find fulfillment in it, what really sets Automattic and WordPress VIP apart is the people. We come from a wide variety of backgrounds and places, and every single person is extremely talented, kind, and just plain amazing. I wouldn’t want to be anywhere else.

By the way, we’re hiring! 😉

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3 responses to “Five Years”

  1. Philip John Avatar
    Philip John

    I miss working with you Derrick! Congratulations on the milestone 🙂

    1. Derrick Avatar

      Phil! I miss you too! When are we going to get NewsPack VIP so our worlds will once again be the same?

      1. Philip John Avatar
        Philip John

        At the moment I think we’re mostly taking clients off you 😀

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