Automattic: 10 year anniversary

I’ve spent just barely under a third of my life working for Automattic. These were not mindless years that somehow added up. I have felt each of them in the best way.

wordpress. this is new. kevin and the gang went to teh VIP conference and he got me some AWESOME contacts. needless to say, i would love this job. work from wherever. still in tech. still can do creative stuff. still can build websites. like whaaat.

On my private blog on April 3rd, 2014

I tried looking to see my first mentions of working for Automattic and stumbled on the above nonsensical private entry. I left the typos and chaos in because that’s the reality of where I was when I applied. I was also 21, graduating college a year early, had applied to easily over 100 jobs, and was trying to move to San Francisco. I sent in the following as my application, nervously waiting to hear back:

Hello!

If I were to write an article right now it would probably be called “My Three Years Without Pants” as a continuation of the wonderful book by Scott Berkun. Why? Because I am a psychology major who has been working remotely for the University of North Carolina at Chapel Hill’s web.unc.edu (a WordPress multisite) for the past three years. I recently read and chuckled through “A Year Without Pants” and realized I relate and love the work I do. I have never experienced a “real” work place often working from coffee shops, dorm rooms, my phone, etc (at a coffee shop currently!). Right now, I am a Web Support Specialist for the University and a Web Master for two non for profits. I have such a passion for helping people create their vision on WordPress and often find myself jumping onto our support forum when I should be doing homework. My work experience has made me incredibly comfortable replying to forum posts, writing documentation, meeting with users, and training users. To actually work for the company that has allowed me to be employed for three years all while wearing my PJs would be amazing. 

Attached is my resume. Here is my LinkedIn account and here is my personal site as well as a fun meet up site I made called ILifeChat. 

Thanks for considering me!

Best,

Anne McCarthy

From my first application on March 31st, 2014

No response. Within the few months it took for Automattic to get back to me (on June 3rd asking for a text based interview the very next day on skype), I had entered the final stages at Lyft and Earnest (and nearly the final stages with Airbnb’s trust and safety team). I couldn’t drop the idea of working at Automattic though and I decided to risk reaching back out again.

Hello!

I just wanted to follow up with you all as I am entering the final stages of a couple of different job opportunities but have my heart set on working for Automattic. I have worked for three years at UNC Chapel Hill’s VIP multisite client, web.unc.edu. I have worked with non profits, departments, student organizations, and individuals to create WordPress sites that give a virtual space for their passions. I contribute to our forum here at UNC as a support specialist and provide WordPress training for faculty and students alike. Every site I have runs on WordPress and I spend more time than I’d like to admit tinkering with sites 🙂 I am heavily experienced with HTML and CSS and am in the process of learning PHP as I am building a “People” plugin specifically for UNC’s web community. Ultimately, I would love to be able to continue to do this full time and look forward to hearing back from you all.

Best,

Anne McCarthy

From my follow up email on May 16th, 2014

This was the truth: I had my heart set on working for Automattic. When picking jobs to apply for, I intentionally tried to pick companies whose products or focus I benefited from. This included everything from looking at jobs at FIFA to Redbull to Airbnb to Lyft and, of course, Automattic. I’m an intense person and I wanted to go to a place that would only inspire and embrace my intensity and curiosity. Out of all of the companies though, Automattic captured my imagination with a global crew working on interesting, hard, long term problems. Plus, I truly couldn’t stop tinkering with WordPress and spinning up sites.

Ultimately, Automattic has proven to be the best, most challenging place for me to land. I’ve been able to go deep into whatever role I’ve had and scribble far outside the lines, launching numerous side projects over the years, like Accelerate.lgbt, Mentor Everywhere, Museum of Block Art, LGBTQ+Press Empowerment Grants, Uniting WordPress YouTubers. I’ve been on the release squads from WordPress 5.9 right through WordPress 6.6 in various roles (Release Coordinator, Test, Core Editor Triage). I’ve gone deeper and further into the WordPress world than I could have ever imagined in these 10 short and long years.

I’m incredibly proud of that 21 year old kid who reached back out, who kept trying, and who juggled a new full time start up job alongside a few website clients to complete my trial a full decade ago. To this day, I still can’t believe I was offered a job and was able to join Automattic. As much as possible, I’ve tried to ensure that the gift of working here (the flexibility, sabbatical, health benefits, salary, etc) could benefit more than just me. This has meant showing up for numerous weddings, funerals, moves, and more, alongside doing what I can to bring others into the WordPress space. I’ve taken my mom on countless trips and have had an overflowing number of trips with friends. I’ve lived for longer than 6 months in a handful of places (San Francisco, San Diego, Salt Lake City, Seattle, Mills River) interspersed with too many to count jaunts, often with just my backpack in tow or my minicooper powering me.

Without this job, I don’t think I would have built a real relationship with my birthmom nor met my broader siblings. I don’t think I would have been able to fly in to bury my brother. I don’t think I ever could have seen my cousins grow up each year in Western NC where we all gather. I don’t think I would have met my Great Uncle, my grandma’s brother, before he died in Western PA. I don’t think I would have seen my grandma so often nor have had the luxury to spend hours with her in the middle of the day in a rehab hospital months before she died. I don’t think I would have been able to be as present in loved one’s lives, showing up to see their world, their hometowns, their new houses, their kids, their pets. I don’t think I would have been able to heal as well as I have from various injuries this year (flexibility of schedule + great health insurance is everything). I don’t think I would have been able to travel with my mom and create countless memories in so many countries. I don’t think I would have been able to go to two different Women’s World Cups (2015, 2019), fulfilling some childhood dreams. I don’t think I could have watched a best friend play in the Women’s Rugby World Cup (2017). I don’t think I could watch my best friend compete on American Ninja Warrior back to back to back years with last minute travel plans and very late nights. I don’t think I would have ended up in Seattle, a place that has been so good to and for me. I don’t think I would have been able to hike so many miles up and down so many mountains.

Without Automattic and everything that comes with it (the people, the incredible problems to solve, the way of working), I know my life would be so drastically different and frankly more narrow. The ability to live anywhere has allowed me to live so intentionally and bravely, when I can muster up the courage. It’s changed me in too many ways to explain and given me irreplaceable time to be present sitting across from those I love, whether it’s in the middle of the day or the middle of the night. The open ended time with loved ones, real time, is everything. I only hope to pay it forward, to keep showing up, and make Automattic better than I found it. This job is one of the best things that’s ever happened to me and I’m so deeply grateful today for all of the folks all over the world that I get to work alongside who make that a reality.

Intermixed into the joy and hardness of engaging deeply in life are these incredible and meaningful problems I get to work on everyday for my job. I feel lucky that I get to work on these long term problems, like creating and keeping the web open. A decade in, I know I am better for it and my perspective has increasingly shifted towards one of longer term thinking without losing sight of the daily actions I can take to create momentum and change.

Because a decade is hard to conceptualize, I dug into the numbers (just internal, not including my broader WordPress community work in the last 4 years):

• 5 different roles (nearly 6 if you count some DEI work I’ve done on the side).
• 10 years.
• 4,837 posts.
• 7,426 mentions (other people tagging me in a post or comment).
• 17,332 comments.
• 465,114 slack messages (not including WordPress.org slack).
• 2,145,395 words (not including posts on WordPress.org).

Here’s to another decade (and to me learning to be more concise so as to not need to write two million+ more words).