10 Years with Automattic

In February I reached my 10 year work anniversary with Automattic.

tl;dr It’s been awesome.

It’s hard to try and compile 10 years into one blog post, so I thought I’d cover some of my accomplishments and also add some thoughts about Automattic and what it has been like to work there for a decade. Let’s do this!

Goodbye to my thirties

Screenshot from the intro video I made on my first day. Fun fact: I did the first intro video ever! My daughter Hazel in the picture is now eleven years old!

I was 30 when I started at Automattic and am nearing my 41st birthday in August now. It’s pretty incredible to thing of all of the things that have changed in my life personally and professionally:

  • My family grew from 3 to 5!
  • We moved to Glasgow, Scotland, then back to Seattle, and moved to Missoula last year.
  • We bought a house! 🏡
  • I’ve mourned the death of family, friends and colleagues.
  • I believe I was the 56th hire for Automattic when I joined. The company is now over 1,200 people! 😲
  • I contributed to some great products at Automattic: WordPress mobile apps, Simplenote, Crowdsignal, WordPress.com personal and business plans, etc.

Never stop learning

The first line of the Automattic creed is “I will never stop learning“. I would say this is something I’ve enjoyed most about working at Automattic. Here’s some things I’ve learned since joining (to varying levels of expertise 😉):

  • New programming languages: Objective-C, Swift, Python, C#, Modern JavaScript
  • App Frameworks: Android, iOS, macOS, Windows Mobile (RIP), webOS (RIP)
  • Web Frameworks: React, SASS, Node JS
  • Leadership experience
  • Public speaking

All of that was learned by switching up the products and teams I was working on over the years. Automattic encourages you to change things up frequently and I had plenty of opportunities to try new things.

Distributed work is superb

Automattic offers amazing benefits like unlimited vacation, freedom to spec out your computer, great health plan, paid sabbaticals every 5 years, etc. But if I have to choose my favorite I’d have to say it’s the ability to work from home. It took some getting used to after working in an office for my entire career before joining, but I think it really is the future of work. Sometimes I think back about my previous commute to work – it could take over two hours to get to the office in the Seattle area traffic. What a waste! I often am thankful that I can take a quick break from my desk at home and walk my kids home from school or go for a run.

That said, one thing I’ve found about working from home is that you need to remain disciplined with a regular daily work schedule – especially for those that have young children. I will occasionally work a bit in the late evening if needed, but for the most part I’m still a “Nine to Five”.

Our CEO Matt Mullenweg has a new-ish podcast called Distributed that dives into details about how Automattic works in a distributed fashion. I highly recommend it!

Travel, travel, travel

With COVID-19 it’s weird to think about traveling at the moment. But usually Automatticians meetup around 3 times per year to get to know each other better in person and work on a project together. Any location in the world can be chosen as long as the costs meet a budgeted amount. I’ve been to many places I thought I’d never get to see including Tokyo, Buenos Aires, Porto, Athens, Dublin, and Barcelona. The list goes on!

Automattic’s mobile team circa 2013 at a meetup in Greece. I still have that RVCA shirt, maybe time to throw that one away!

We also have “The Grand Meetup” every year where the entire company gets together for a week. These were more intimate in my first few years at the company – we could all fit into a small room and have casual discussions about our future. These days it feels more like a tech conference, but is still a really great week to meet new Automatticians and spend some time together.

Amazing colleagues

Automattic hires people from all over the world and it has created a very unique and diverse company culture. I’ve truly enjoyed working with so many different people over the years and many of them have become dear friends of mine! I’ve learned a lot from them about being a better programmer and team lead.

What’s changed?

Automattic has done a good job at keeping its core values and culture over the years it has grown (Distributed work, relatively flat structure, high trust placed upon employees). I think the main change for me is the sheer volume of people and projects at the company. In 2010 I knew everyone at the company and what they were working on. In 2020 Automattic now has large teams for WordPress.com, Woo, Jetpack, Tumblr, etc and it is impossible to meet everyone and have knowledge of everything we are working on. This is a good problem to have, though, and I have been truly impressed with the products we have been releasing lately.

One little note, we have started releasing software that we built for our distributed work to the public. One of these tools is P2 which we use to collaborate with each other asynchronously. You should check it out!

Join the fun

Even in these unstable times, Automattic is still growing and hiring! If you are interested in working with us check out our active listings. If you apply and know me personally, please let me know and I’ll add a recommendation to your application!

On to the next decade

I like to say I’ll work at Automattic “As long as they’ll have me” 😀 I’m excited to continue learning and watch this company grow and help the web become an even better place.

So, maybe I’ll write another one of these posts when I’m fifty?