Judd Blair on his deep love of learning that makes him an office go-to for all sorts of advice

Not so long ago, you went from an engineering position to engineering management? What was that transition like?
When you’re an engineer, there’s a lot you can do to make your team better, but as an engineering manager, it’s your mandate. I’m here to help people do their best work, and to me that's powerful. The tricky part is, how I achieve that isn't always clear. A lot of times, there are multiple paths to an outcome.

What have you learned since taking on your current role?
Before, when I encountered a problem, my first instinct was to put on my headphones and work on the problem myself until I solved it myself. That was my operating model, and that's really not a good first instinct as an EM. So, I’ve had to grow out of that. When I have a problem now, I rely on my team and focus on what I can do to help them, so they have everything they need to do their best work. Honestly, it's been one of the biggest lessons for me over the last year or two: how powerful teamwork is. You can only do so much with your own two hands in eight hours.

How has Plaid changed in the almost four years since you joined the company?
In a lot of ways, it's the same but bigger. We’ve maintained a lot of our culture as we've scaled up, which has been really awesome to see. I think the biggest thing that has changed is how we work together. When I joined, we were so new, it was a little bit like the wild West. We had to build out a lot of processes and change how we organize as a team. On the engineering side, that’s been done in a way that balances operational excellence and efficiency with team health and culture, which can be hard to pull off. You want to roll in just enough process to make the team better, but you have to be careful, because if you swing too far, it's going to feel really heavy and “big company” way too early.

If you had to describe Plaid, which word would you choose?
I would say, thoughtful. We move with urgency, but we think carefully about things. And that thoughtfulness extends to all aspects of the company not just technical processes and projects. We are very thoughtful in the way that we approach and interact with each other and work as a team. It's something that my wife notices, too, when she comes to the office. She's always saying how welcoming my coworkers are—that they’re really nice people.

What sparked your interest in software engineering?
I think it started when I taught myself to write code around second grade. My grandmother gave me an old IBM PC Junior, and when I was digging through all of the cartridges and floppy disks that came with it, I found a cartridge and a manual for Basic, which is a programming language. I had no idea what it was, but I popped it in and started going through the book, and I realized that, wow, you can actually tell the computer to do things. I remember flying through the manual and then checking out a bunch of books from my school and spending the summer trying to build a game, which was a complete disaster but an important learning lesson. Ultimately, I think it's that intersection of logic, creativity, and execution that was—and still is—really engaging to me.

You decided to study pre-med in college. Why do you think you went that route?Honestly, I was young and had no idea what I was doing. I didn't know anything about software engineering as a job, and I had also convinced myself that I needed to keep pushing myself to learn new things instead of going deep on the things that I'm already good at. So, I went wide and settled on pre-med, because I had a direct line of sight to a really challenging career at the end of it, and I had excelled at various sciences, not just computer science.

Ultimately though, you did graduate with a degree in computer science. What set you back on the engineering track?
I think one of the main reasons was that medicine is a lot of application of knowledge, and that requires a lot of memorization, which has always been my Achilles heel. I've always been more interested in the why and how.

What brought you to San Francisco?
I wanted to go to where the action was. So, I bought a one-way ticket to the Bay Area. I had never even visited before, but it ended up really clicking for me. I love the accessibility of the outdoors here. Being able to go wine tasting and go to the beach in a single day is magical.

Where was your first job?
I started working on internal tools for Google. Basically, I was the web developer on a team of Oracle specialists that built the tooling and the database that stored financial information. My job was to make it easy for teams to do their jobs using that financial information.

Where did you find your next job?
While I was working at Google, I was spending a lot of time commuting by bike from San Francisco down to the South Bay, which is a 40- or 45-mile ride. There was a group of us that did it, and I got to meet a lot of interesting people from a bunch of different companies. One of my friends from the group had just started at a small startup called Euclid Analytics, and he was looking to hire full-stack engineers. I was looking for a change at that point and took the opportunity.

How did you make your way to Plaid?
I eventually left Euclid for a senior software engineer position at a company called Autolist. But it was through one of the founders of Euclid that I found out about Plaid. He kept bringing up Plaid as a company that he thought had a lot of promise. He introduced me to William, one of Plaid’s founders. Later on in the interview process, I met Zach, the other founder and our current CEO, and all the engineers I’d be working with. They all seemed awesome, and that was honestly a big reason why I decided to join Plaid. I could tell that they made a really great team.

Now, you’re practically a Plaid fixture. There’s even an #askjudd Slack channel. How did that come to pass?
I have a little bit of a reputation for being opinionated, I guess, and so I ended up fielding a lot of random questions on Slack. People would be like, "What headphones should I get?” or “What's the best way to buy a car?" The channel originally started as a repository so that other people could see the answers to the questions I was being asked, but it has grown up a lot. Ninety-five people are on the channel, and this year at our company retreat, Zach mentioned it at the all-hands presentation. That’s when I knew it was officially a thing.

You also started a Plaid wine club called Wine and Opine. Where did the idea for a wine club come from?
It started when I was talking to one of my friends on the Legal team. She was planning to go to a restaurant where I really liked the wine list, and I was helping her navigate her way through it, so she would have some idea of what she wanted to order. She said, "It'd be really great if we actually share this information with everyone," and Wine and Opine was born. From there, we started going deep on particular types of wine, and we started tasting the wine, too. My first presentation was on Burgundy. It was a pretty big hit. Since then, we’ve done Sonoma County, sparkling wines, and budget wines.

How did you develop such a strong interest in wine?
I think it started with pairing wine and food together. I love food and cooking, and wine is an elevator that takes food to the next level. A lot of the time, I'll pick out a bottle of wine that I'm really stoked on, and then I'll build what I'm cooking around that bottle. Really, wine is just another kind of food for me. It's all about the flavors and the experience.

What is it about cooking that appeals to you?
I love cooking for the same reason I learned to love writing code—it ties together logic, creativity, and execution. There are the building blocks of what it takes to make great food. There's envisioning really creative things to do with those building blocks, and there’s the act of making it all come together. But of the three, execution matters most to me. I care more about making something really excellent than I do about making something outrageously creative that's never been done before. Right now, for example, I'm experimenting with sourdough cultures and trying to perfect my style of pizza.

What else keeps you busy outside of work?
I really like music—listening to it and making it. I have a guitar, and I've been teaching myself how to play the ukulele. I collect vinyl records. I'm into headphones and music equipment. I still ride my bike but an embarrassing amount of my miles are indoors. I’m hoping to shake the dust off my snowboard this winter and get up to Tahoe. I play board games and video games. I’m into photography—mostly travel and some street photography, and I dabble in analog film as well. Lately, I’ve also been doing a lot of DIY projects around my house. I learned how to fix marble countertops the other day.

That’s a lot of hobbies. How do you find time for it all?
It’s a matter of being very deliberate about what you choose to go deep on at the moment. It’s also a matter of not letting those other things atrophy. Even if I'm not deeply invested in some cooking project, for example, I'm still cooking a lot; I just don’t focus on it as intensively. Then there’s the whole 90/10 thing. Instead of spending infinite amounts of time perfecting that last little bit of something, I think there's a lot of value to be found in the first 90% of the effort. That's where you can take something from good to excellent but not necessarily perfect. That's what I'm interested in, and that's how I like to look at things.

What are you proud of?
It’s hard for me to answer this question, because I view so much of what I do professionally as a team effort. I’m constantly humbled to work alongside everyone at Plaid. If I’m proud of anything, it’s that the people I work with value my opinions, because they set a really high bar.

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