Kevin Singleton is now a software engineer at Vanta, an early-stage Bay Area startup that develops a security software package for other tech companies. But until 2017, Kevin was a scholar of Japanese culture pursuing a career in academia; he even attended Harvard to obtain a Master’s in East Asian Studies and earned a Ph.D. in Japanese Literature from Stanford. After following that path for a number of years, he decided that he wanted to chart a different course with his life.

Although he had a minor in Computer Science from his undergraduate days and a persistent interest in coding as a hobby, he had no credentials, experience, or contacts in the tech industry to get his foot in the door. On a whim, Kevin decided to take our technical screen—and crushed it. With Triplebyte to vouch for him, he was invited to eleven on-sites and received multiple offers. After he settled into his new role at Vanta—his first ever in the field of software engineering—we caught up with Kevin to talk about his experiences.

Note: This interview has been edited for clarity and length.

Becoming a programmer

How did you first get your start in programming?

I have an older brother who is six years older than me, so separate enough to where we're not really rivals with each other. And he was always very computer-oriented, very engineer-oriented. He's currently an electrical engineer. And, certainly, that had an influence on me, growing up. I was a big video game nerd, computer nerd. Programming things in BASIC, which kind of makes me wince, as I think about it. We had Apple IIs and Tandys. This was back in the late '80s—divulging how old I am!

Yeah, it was definitely through my brother. I'm not sure, exactly, how he became interested in it. But we didn't have a home computer. My first computer wasn't until I went to undergrad, but my mother had old Tandy computers at her office with the five-inch floppies, and it had BASIC on it. And I remember there was this one BASIC programming book from our local library that we would just check out over and over again, and it would give sample programs. And I never learned object-oriented programming, at that time. It was literally just like, "Program line 10, print this, go to this,” just a bunch of subroutines.

That's cool. Okay, so you were kind of into gaming, your brother was programming, got started doing BASIC. How did that become enough of an interest that, when you first went to college, you planned on majoring in CS?

Oh, I think, like too many people before me and probably still today, the dream was to become a video game programmer. And then that was also part of why I wanted to learn Japanese, as well, because that's where all the good video games were being made at that time. So I was definitely more math-oriented all through high school. I figured I was going to do something with computers or engineering. And then, at Colorado, computer science was the only engineering major that you could take where you didn't have to take chemistry. I think that actually guided my major choice more than I would care to admit!

But it was always kind of like this “given,” even when I was in high school. I don't think I really thought as much as I probably should have, growing up, just in general. I'm good at computers, this is what I'm going to do. I spent a year in Japan and it kind of sucks you in. And I think that was one of the reasons why, after I went to Japan, I kind of turned away from it, because I was like, No, there's more to life than this.

So what happened was, after undergrad I lived and worked in Japan for three years. And, at that point, I made the decision that I wanted to pursue an academic career in Japanese. So then going to graduate school, I first did a Masters in Harvard in Japanese before going to Stanford for the PhD.

Okay. So that seems like you were definitely headed down the academic, Japanese professor track. How did you make the switch back to computer science?

Well, that's the thing. For that type of major, a humanities major, there really is only one career that you're trained for. You go down a rabbit hole, whether you like it or not. So the story behind the change is, a year before I graduated, or maybe two years before I graduated, I did the job search for one year and failed spectacularly. And then I was preparing to make another round of applications. So very different from Triplebyte, with all these companies that are essentially hiring 24/7. I was looking at tenure track positions, and the pickings were fairly slim. It's one of those cases where there's not that many people applying, but the jobs are even fewer, so it's very competitive. I didn't really see myself as a spectacular Japanese literaturist.

So then what are you going to do? Well thankfully, in my case, I had my minor in computer science from back in the dark ages. And at Stanford, while working on my PhD, I was like, Hey, I'm at Stanford and I used to do computer stuff. Maybe I should sit in a few classes. I remembered, Oh, this was actually really fun. And things are very different now, in terms of the tools that are available, and the ease with which you can make something really cool really fast, even if you're by yourself.

And so after making the decision that I wasn't going to be a professor anymore, I was like, Oh, I have these skills and I know they're valuable. I've even seen the salary ranges. I could be a mediocre software developer and still do better, financially, than a successful academic.

On using Triplebyte to find a job

But at the same time, I’m thinking, “I’m older. Here I am getting into my late 30s, I don't have a tech resume to speak of.” And so I wasn't really optimistic or thinking, Okay, I'm going to get 18 offers right away. My initial plan was to just code some things independently, build a catalog that I could leverage into gainful employment. So I quit that job, decompressed for a month, and then was half-heartedly sending out applications without any expectations. And those low expectations were met—I thought, I'm not going to hear from anybody, and I didn't.

And then I literally just kind of stumbled... I'm not even sure where I stumbled upon this ad for Triplebyte. I kind of took that quiz on a lark, I didn't even prepare for the quiz because I'm like, Ah, this seems like a joke. And then things just kind of took off from there. I was able to get through the interview and did pretty well. Once I was in the part where they choose companies, it was just amazing.

That whole time, I've got the devil on my shoulder saying, The jig is going to be up. No one's going to want your old ass. But then I was able to talk with my account manager, another guy named Kevin. He was like the angel on my shoulder, who just said, No, I think you're in a good place. He was great.

Once it went live, and then I had requests, I was like, "Wow, this is actually happening.” A week passed and I had four or five on-site interviews lined up, already, and more pitch calls left.

Yeah, what did that feel like for you? Was that, for you, personally that encouraging?

Certainly encouraging. I mean, the interesting thing was, I definitely didn't try to sell myself. Because I can't pretend that I have more experience than I did. I can't pretend that I have the same background. But I found that the people that I talked to—I was surprised that, by that point, they didn't care anymore, to an extent. I mean, not 100%, but what they're looking for isn't necessarily defined by background. If they're on their own, the easiest indicator is getting that resume. But if they have this other service that's tried and true, then literally—once you have shown that you can meet that base, that you know how to code—they're just so desperate for talent that it's really anyone's game.

That's awesome. That is so encouraging to us, because that is definitely why we want to do that. Speaking a little bit more broadly, about the background-blind process, what do you see as the value of that for the industry?

Given the speed with which tools are developed, it's a very level playing field. It’s relatively easy to pick up these marketable skills without having those years of experience. There's so much demand for work that it far outstrips people's specific backgrounds.

And it seems to me that the startup culture and ecosystem is already very scrappy, in a way. The only reason, it seems like, why there are so many people with similar academic backgrounds is because, essentially, they're classmates. It's people just leveraging the networks they had. This creates a different sort of network. And I do think a lot of startups recognize that background diversity is really important, both in terms of company culture and even for questions of product. So I think a lot of the forward-thinking startups kind of want techs to get away from that sort of insularity.

On learning independently

I know you had the minor in CS. How did you go about teaching yourself? You took some classes at Stanford, did you do anything else to self-educate?

Those classes, more than anything else, I would say, served as a way of transitioning from Can I code? to Can I build things? I took advantage of a lot of MOOCs, for sure. There's so much there, like Udemy, Udacity, Coursera, and it’s cheap. You can get 100 hours of fairly sophisticated iOS development content for $10 or $20. So I listened to a lot of the classes—but I was also trying to build things on my own, even if they weren't necessarily related to what I was listening to.

What kind of projects were you working on, along the way?

Mobile was what I had been working on, because it felt like what I knew. Just making dumb games, or playing with graphics and gradient builders, and learning the nitty-gritty for that. Something like, a tool that I wanted. Along the way, you learn umpteen different things that you didn't know before, and then you've got this little utility that you can use.

Choosing a company through Triplebyte

How did you decide to go with Vanta?

It was definitely not an easy decision. I was not expecting to be in this position where there are offers on the table that I have to choose from! To backtrack: with academia, the tunnel vision is ridiculous, in terms of both what you're focusing on for your research, and your career path. I kind of lifted my head from the books and realized there's this whole world out there of people doing things. One of the most valuable things about the Triplebyte process was being able to taste that, in a very short amount of time. Just being able to talk to people that have the vision, the drive, and the resources to do really cool things. It was like, Oh, my god. Why wouldn't anyone want to work for you? But then you're talking to over ten people like that, and that was just amazing.

With Vanta, it was three people at the time. Two of them were founders, and then employee one. Of all of the offers, that was the one that seemed like, “this is the thing I would regret not doing. Whatever happens, this is going to be the something that's not going to be repeatable. To be able to come to this tiny company and watch what happens, for better or for worse.” Every opportunity I had to talk with the founders was great. Erik and Christina, the people at Vanta, I think we really hit it off.

It’s super exciting to join a startup at that early stage. In a few words, how would you describe what Vanta actually does?

They make it easier for companies to demonstrate compliance, essentially, for cybersecurity. So they kind of facilitate auditing for cybersecurity, through their tool.

Is there anything that you’d like to add about your story, or that you'd like to say about the Triplebyte process?

I mean, my experience was great. I can't guarantee, like, "Oh, you went to coding bootcamp. Do Triplebyte and you'll definitely get an engineering job.” You know, I wouldn't want to overpromise.

But it seems like it was such a rare thing to find, where the company did exactly what they said they were going to do. And that it was able to validate so much of what often seems like lip service, in terms of job hunting and career searching. And how people will talk about, Oh, we don't care about your resume, we just want people who are smart, who know how to solve things.

I'm a data point, I feel like. I literally had no tech resume to speak of, no internships, nothing, just a knowledge of coding. I will say that I did have the feeling that my knowledge was non-trivial, so it wasn't the case that I had just attended a bootcamp for a week or taken a couple of classes. But it was very rewarding to have that feeling validated, not only in the initial process through Triplebyte, but then in talking with companies.

The problem has always just been, how do you allocate the resources to try to find those people? It seems so simple, but clearly it was a longstanding problem—yet Triplebyte seems to have done this. And it changed my life in inestimable ways.

Man, that's super encouraging. Thank you.

No, thank you.

Why isn't everyone happy all the time?

We've been ending our interviews with this completely different philosophical question, which is: Why isn't everyone happy all the time?

The question seems to imply that people should be happy all the time. I'm not sure—what would I do if I was happy, all the time? I'm not sure I want to be happy all the time!

But perhaps the question is, why are people miserable more often than they should be? And it's something I wonder about.

If I had stuck it out with computer science back in the early 2000s and got a position—who knows, maybe I would have been employee number 20 at Google, and I would own the third floor of this building. But when I'm on the Caltrain, going to work, I still kind of disbelieve that I'm in this position that I'm in.

I do, sometimes, take the time to look around on the Caltrain at people. And a lot of people, they look really tired. And they look kind of grumpy, like they would rather be somewhere else. And I'm usually pretty tired, myself, but I will kind of take advantage of those moments to... If I feel like maybe I'm scrunching my eyebrows more, I'm like, Well, you don't actually need to do that.

Thanks so much for your time, Kevin! Glad we got to catch up with you.


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