When Brandon Kraft was in kindergarten in 1990, his dad had a hunch that computers were going to be a big deal. So he trudged off to the local Sam’s in Wichita Falls, Texas, and bought a computer he could afford — an Intel 386 with 16 MHz of processing power and 8 MB of RAM. It’s probably safe to say that day sealed Brandon’s fate as a geek (his words) and a brilliant Automattician (ours).
Q. What happened with that computer?
My dad knew nothing about computers. At the time, he was working for the military teaching enlisted folks how to splice cables. He set it up for me and never touched it again.
It was a big old box. It became my way to pass time in the middle of the Texas summer when it was too hot to go outside.
Q. Did you always know you’d get into technology as a career?
I fought it for a long time. All through growing up and high school, I was always the “geek” and didn’t want to be. Initially, I hard-pivoted away from that and moved to Austin to go to the University of Texas. I got a degree in sociology, which is probably as untechnical as you can get.
Q. That doesn’t sound like a recipe for a tech career.
I guess I was trying to buck expectations. But at the end of the day, I always found myself pulled back to that kind of work. I could never get away from it. After college, I worked at the campus ministry for five years doing lay pastoral work, but I still ended up in charge of IT on the side.
Q. How did you get involved with WordPress?
When I began tinkering with the internet, I liked the idea of self-publishing. There might have been a little ego involved, thinking I had things people wanted to read. I made a personal website in the eighth grade. Nothing fancy, I just wanted to write thoughts about this or that. It was hand-coded HTML, and at some point I realized: there’s gotta be a better way.
I found Moveable Type, an early blog/CMS tool. They ended up changing from open source to closed license. Even if I didn’t yet understand all the positive implications of open source software, I was drawn to the idea of software as collaborative.
Everything came together with WordPress. It was at the intersection of me having things I wanted to say, being drawn to tech yet wanting to work directly with people, and caring deeply about the philosophy and sociology of how people work together to improve the world. WordPress made sense of all of that.
I used WordPress to make my own site and started helping other people to make some spare change. I ended up submitting patches to WordPress and went on to become a core contributor.
Q. How did that turn into a full-time career?
While I was working at the college ministry, I got married and started having kids. I realized that working at a college campus ministry is great, but it’s basically all nights and weekends meeting with people. Then, you still have to work during the day doing stuff when people aren’t visiting you. It wasn’t sustainable with a growing family.
I was doing web work and taking care of the church website anyhow, so I turned them from my employer to my first client with a maintenance agreement for their website. And that got the ball rolling so I could actually make money being a geek — even without a computer science degree.
Q. How did you end up at Automattic?
My wife eventually started working full time and I became a stay-at-home dad, but I really needed an adult outlet. I could do freelance projects during naps, nights, and weekends, which kept me sane while having little kids at home — six girls between ten years and 18 months old. At the end of the day, I wasn’t the most stellar stay-at-home dad. I like to say I had a lot of “growth potential” that I wasn’t reaching.
My wife was getting burned out at work and wanted to be home with the kids. She said, “You need to get full-time employment, or figure out how to make the freelance stuff cover everything.”
I was happy to do either one and I figured if I could work for someone besides myself in this ecosystem, it might as well be Automattic. They’re the big dog in the WordPress world. But I had a little bit of imposter syndrome. I had no real credentials, no degree, and had never worked full time in WordPress. I thought “I could apply for this dream job, but who gets a home run at their first at-bat?” I ended up applying and made it through the trial.
Q. What was your first role at Automattic?
I started in 2013 as a Happiness Engineer on the support side and did that for about five years. Then, two years ago, I swam across the river into development.
Q. What was it like being a Happiness Engineer?
I liked directly interacting with the folks using our stuff. There was a joke we used to make at Happiness: “If your website’s making you sad, my job is to make you happy with it.” It might sound cheeky but it’s true. I really liked getting to know the people behind the websites.
Q. Is there a story that stands out?
There’s a police chief in Aransas Pass, Texas, a really small coastal town. He runs the website himself and uses Jetpack. And I guess he’s a bit of a geek, too
Jetpack has a feature that emails your new posts to your subscribers. He set up his site to automate daily police blotter updates: the site pulls updates from the software the police station uses and publishes them as posts on his Jetpack-powered WordPress site. From there, they get emailed to citizens who subscribe.
He’s using Jetpack to stay engaged with his community without having to expend money that small governments don’t have or the time of one of his few employees. Those are the types of stories you hear in Happiness.
Q. How did you end up going from Happiness Engineer to Code Wrangler on Jetpack?
Customers often report bugs, but not every bug is a high priority to fix. If I knew that was the case, I would tinker around to fix it myself. That snowballed into doing bigger fixes, and then taking on some projects that we didn’t have the bandwidth on the development side to take care of. Eventually, it made sense to switch to full-time development.
At Automattic, customer support is a career in and of itself — being a Happiness Engineer isn’t a stepping stone to a development role. But there are organic ways to transition between roles, which is what happened with me.
Q. How did being in support prepare you for being a Code Wrangler?
It made me a better engineer. It’s sometimes easy for people in engineering and development to forget that the problem isn’t just the code. You’re trying to create or debug something, sure, but it’s for a real person with a specific need. It’s not just trying to make this widget work right. It’s trying to make this widget work right so this author can let people know about her new book.
Now, when the developers are having a conversation and they suggest something, I can be the one to say, “Let’s sit down and think about it like a customer. Would this be helpful or confusing to them?” Being able to bridge that experience to the development side is a win.
Q. You’ve had an interesting career arc from ministry to support to developer. Are there any commonalities?
It’s the same and different at the same time. With my ministry work, a lot of people were coming in to tell me where they are in life, maybe a problem they were having in school, and I tried to help them toward a solution.
In a lot of ways, that’s not that terribly different than doing customer support. They have a problem and you’re supporting them, guiding them along the right path.
Whether you’re in support or ministry or development, you’re trying to identify a problem, either with an individual, a piece of software, or use cases, and you have to understand that problem deeply so you can recommend or create a solution.
Q. How do you explain Jetpack to people?
Automattic has been making WordPress.com and hosting people’s WordPress sites for close to 15 years. We’ve learned a lot over those years about what websites need, what feature sets and tweaks users need, and how to make things better. Jetpack brings those same features and resources to anyone who runs a WordPress site, no matter who you host with.
The Related Posts feature suggests other content your site visitors might want to read. It makes your website stickier, so people click through and see more content or ads. But the actual computational work to figure out what is the best related post is actually pretty hard to do without a lot of computer power. With Jetpack, all that computational stuff happens on our side. We crunch all the information so don’t have to do it on your own server and feed that information back for the best related posts. Offering that kind of solution — where it’s not just about a little code, but being the bridge to access enterprise-level functionality — is the more interesting and exciting part of Jetpack.
Q. What’s another powerful feature of Jetpack?
Jetpack Search. Most site search functionality is simple and not very smart. But Jetpack Search uses natural language technology so it knows when you search “cat,” “kittens” are related but “category” isn’t — it generates more reliable and beneficial results. Search can actually be used by people to find something that they want and not something that you hide on your site because it doesn’t work.
Q. Are there any really cool features of Jetpack that are underutilized?
Tiled Galleries makes it easy to have a mosaic of images that can be much more visually interesting than something like a click-through carousel. It can resize the images to make a tiled mosaic. It can do more than just shrink images; it modifies them on the fly so they look great.
Q. Just for fun, what’s one of the most obscure features of Jetpack?
It’s gotta be Beautiful Math. It’s used in academic math and engineering circles. It’s a markup language for writing complicated mathematical equations. Jetpack automatically converts these long strings into pretty mathematical formulas. You would never know about it unless you needed it.
Q. Are you still involved with WordPress core even though you’re a Jetpack developer?
I still spend five hours a week on it, mostly voluntary. In seven years worth of WordPress versions, I’ve had at least one patch each release. Not because it’s my job function, but because a rising tide lifts all boats. If there are little bits of things I can do to help everyone else in the process, and it’s fun, why not?
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I enjoyed reading this interview. Thanks Brandon for your work! I truly appreciate it as Jetpack has really been a blessing for my blog.