Meet Anne from Jetpack: Philosopher, Nomad, Happiness Engineer

Automattic is a distributed company made up of people who work from wherever they choose. Together, there are more than 1,000 Automatticians speaking 93 different languages across 75 countries. (Sound like fun? Work with us!) Our ace customer support folks are called Happiness Engineers, and we always enjoy talking with them to get a peek into how they live, what they love, and their thoughts on Jetpack. 

Anne, a self-described nomad and problem-solver who can get philosophical about the concept of backups, was kind enough to let us pick her brain. It was the best hour we’ve spent in a while. Read her Q&A to get to know this amazing person (and discover a few cool things about Automattic and Jetpack, too).

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Q. So you’re a nomad? 

I live in San Diego, but I’m probably gone half the time. Sometimes I don’t have a home address at all, so I put my parents’ address down for my mail. They’re nice enough to let me do that since I could’ve just gotten a PO box.

Q. Where do you like to wander? 

I’ve traveled to Europe a lot and the States. I love exploring the American West and the Pacific Northwest. I can’t get enough of this entire part of the coast.

Q. How do you live the nomad lifestyle?  

I’m pretty minimalistic. I don’t have a lot of stuff. For a trip, I might just take a backpack and load the rest of my belongings into my Mini Cooper — my friends let me leave it in their driveway while I’m traveling. Or I’ll travel with the Mini, so that will be my mode of transportation.

Q. How do you plan your trips?  

I jet off and string together house sitting gigs, AirBnBs, and friends’ houses, and it’s a blast. One of my favorite aspects of working here is the freedom it affords me to really engage and be there in other people’s lives.

I’ve been able to go to weddings, funerals, the birth of babies. I’ve been able to help people on their first day of grad school or help them set up their apartments. I’ve been there for friends going through breakups. You can do this really fun stuff and be there for people in their lives. 

Q. It sounds like being a nomad is about more than just travel?

Nomading for me started out as an adventure and going to different spots — a new place every time. And now it’s more about traveling and community, so I don’t feel bad going back to the same spots over and over again. There are three or four cities in the U.S. where I have a pretty strong community built up, and I know I can pop in whenever, or even go there and live for a while.

Sometimes I travel to new places, but it’s getting rarer as I get older since I’ve seen a lot of my bucket list places. It’s such a fun global context to inhabit.

Q. Is there a place you love the most?

Internationally, it’s probably Switzerland. I just love mountains. I want to nestle up next to some mountains for the rest of my life.

Q. How did your relationship with technology begin?

I was in middle school and a friend messaged me on AIM and was like, “Let’s set up a blog,” and I was like, “What’s a blog?” I started out on Blogger, a Google product, and I went nuts on this thing. It unleashed this aspect of me. I had bad handwriting and a speech impediment growing up, so I turned to writing. Once I was able to type on a computer, I was finally able to keep up with my thoughts. 

I started off writing about soccer, school, and as I read more and more books, my ideas. It was very much based on my emotions, a very intense brain dump. I still have the original blog I had back then.

Q. How did you get into tech professionally?

I grew up in Florida and ended up going to the University of North Carolina. It was expensive for an out-of-state student, so I needed a job and qualified for work-study. All the openings the school sent me seemed very gendered and were for daycare or teaching jobs. I’m an introvert. I don’t want to be around little kids. I don’t want to teach children. I went on interviews and it was just horrifying. 

Then a job popped up that involved WordPress. I’d never heard of it. They wanted someone who wasn’t super technical, but could talk to people and educate folks about a new platform that was being rolled out. Since I’d been blogging for years and had used these interfaces, they hired me. 

I was a psych major, so the employer took a chance on me. It’s really amazing to look back on allies who helped you succeed in your career. As a young queer woman in tech, we all need allies. He saw something in me and ran with it. 

Q. What happened next?

By the time I graduated, I’d been working on bigger and bigger projects with a bunch of departments for the university. We were migrating different department sites from old Joomla, Drupal, or HTML and CSS-based platforms to WordPress.

One of my favorite memories was being a part of the anthropology department’s site migration. At the end of it, they told me, “Okay, now we need to teach the professors.” I had to teach a bunch of professors I had taken classes with. These were emeritus professors, experts in their field who didn’t understand the internet, so it was humbling for both of us. It was such a cool experience to have the tables reversed and it was wild when they would interrupt me with statements like, “Wait, wait, I have a question. Don’t go too fast!” 

Q. When it was time to look for a job after graduation, how did your experience play a role?

UNC turned out to be a VIP client of Automattic. One of my team members went to a WordPress meetup and met an Automattician who said, “You should work for Automattic,” and I was like, “What’s that?” Someone had also given me A Year Without Pants, a book about working remotely for Automattic. I had two forces kind of pulling me in that direction at the same time, so I applied but didn’t hear back right away. 

I had final offers at two other places and I had accepted one of those jobs when I heard back from Automattic and started a trial period with them. (To read more about Anne’s hiring process, read her plug post here.)

Q. Now you’re a Happiness Engineer. How do you explain that to people?  

Simply put, it’s solving problems. Whenever I’m talking to someone who doesn’t understand my job, I’ll just say, “I’m basically a problem solver.” Whether it’s helping people directly, testing something, or writing documentation, I’m there to fill gaps and drive things forward. 

Q. What’s your approach to the job? 

I approach it as a combination of an advocate and liaison. At some other companies, customer support is more like, “Okay, I fixed this person’s problem. I’m good to go.” What I love at Automattic is that you can constantly go back to the bigger picture and say, “How did this problem happen to begin with? What team is in charge of this? Let me test this flow. Can I replicate it? What can I do now to actually fix it?”

There’s a lot of encouragement to really dig in. There’s a never-ending amount of that at Automattic and it makes for a really fun day. It can be frustrating, but there’s excitement when you find something. You’re almost like Indiana Jones discovering a treasure. You’re able to say, “Okay, this is what’s broken.” I love organizing and fixing things and this job lets me really lean into that.

Q. We love to hear stories about interactions with Jetpack users that really made an impression. Do you have any of those? 

I was talking to one customer about backups. It turned very philosophical. We had an in-depth discussion about why people want to save things and what it would look like if we had to store our websites as if they were books. And why is it that sometimes erasing something on your computer feels like losing a part of yourself while other times, it’s easy to throw things away? It was a fascinating back and forth. 

Q. Wow. Any others? 

I had a discussion with a transgender woman who was around my age and was trying to build up her website, Honestly Nomadic. Sometimes there’s just an alignment when you’re looking at someone’s site and I think, “I’m so glad we’re backing this up. I’m so glad we’re helping provide protection and support for this person because this content needs to be online.” 

Sometimes there’s just an alignment when you’re looking at someone’s site and I think, “I’m so glad we’re backing this up. I’m so glad we’re helping provide protection and support for this person because this content needs to be online.” 

Anne McCarthy, Happiness Engineer

Another one that comes to mind is working with a woman whose husband had died — she wanted to make sure his content was okay. We were trying to figure out what to do with the site and what to recommend. I read some of his posts and they were really powerful. I was talking to her about what her options were: how we’ll always have the backups on file and how it’s separate from the host so we can always help her restore. It was all about giving her some peace during a really hard and awful time.

Q. How do you explain the value of Jetpack to someone who’s never heard of it?

At WordCamps, people will challenge me: “What does Jetpack do?” I turn it on people and say, “Tell me about your site. Do you like to know when your site’s down? You probably want Downtime Monitoring. Do you enjoy updating plugins? Not really? Okay, we take care of that for you. Do you like having different logins for every single client site you have? You don’t? Okay, well, we have WordPress Secure Sign On.”

The thing about Jetpack is that there’s everything: it handles everything from super-granular details all the way up to the really big stuff. 

Q. What’s one thing you wish people knew about Jetpack?

I would say Downtime Monitoring. My first really bad memory with a WordPress site I was managing was that it went down, but I had no idea and the client had to tell me. I had a fatal error of some sort. Downtime Monitoring is a really simple feature that alerts you any time your site goes down. Who doesn’t want that? 

Q. What advice would you give Jetpack users? 

Jetpack is really comprehensive, and we’re constantly releasing new things. I’m shocked each time I re-explore Jetpack. It’s easy to turn it on and forget it, which is great; there’s a lot of stuff you don’t have to think about. But at the same time, there’s a lot of value in revisiting what Jetpack is today. It’s not the same as it was three years ago, or even one year ago. 

Q. Last question. Automattic gives employees paid three-month sabbaticals every five years. You just got back from yours. What was that like? 

I went into it determined not to make it another job. Some people go out and try to learn French on sabbatical. I didn’t want to do that. It definitely made me feel really reaffirmed that I had a life outside of Automattic. Spending so much time at a job, it’s easy to get lost in that. The time off allowed me to investigate a part of myself that I think would have been hard to find otherwise in the grind of everyday life. 

There was nothing drastic in my life I wanted to change. I’m pretty stoked about how I’m living my life right now. I just wanted to go a bit deeper. I went into it focusing on three themes. One was spending as much time away from my computer as possible and in nature. Another was spending as much time as I could in community, with new friends and old friends. And the last was to do things that, twenty or thirty years from now, I’d look back on and be really glad I did — I sought out financial advice since I’m early in my career and want to be wise with how I approach money over the long term, and I found a therapist and solidified my meditation practice.

It changed a lot of things. I can be very reactive sometimes, and now I feel like I have a pause button. It feels like I have a well of resources within myself.