Wes O’Haire
  • Years in Tech


  • Current Role

    Product Designer, Dropbox

  • Place of Origin

    San Francisco

  • Interview Date

    March 5, 2016

I’m a biracial (black and pacific-islander) designer who grew up about 80 miles east of SF. I lived in SF a short period during college then moved to LA. I’ve spent the last 10 years in LA but am returning to SF to join Dropbox. I’m passionate about making sure blacks don’t get left out in the tech gold rush.

Why don’t we start at the beginning? Tell me a bit about your early years and where you come from.

I grew up in Modesto, that’s where my parents raised me and my younger brother. They’re still there and I grew up with a fairly normal life. Well, I guess normal for me. My dad’s black and my mom is Pacific Islander. So I had big family gatherings, my mom comes from a family of 15. So just tons of family.

At some point when I was a kid, I remember my dad telling me “Whatever you do just make sure that you—one, do what you love and then two, make sure you know how to use a computer.” [chuckles] So when I was a kid, he’d buy me little books on computer hardware, so I always had a little bit of curiosity towards computers and also towards making things. I was also really big into Legos, I would just build stuff all day. He also bought me a little old record player from a garage sale just so I could tear it apart and take parts out of it… just mess around. So, I always grew up tinkering with things.

And then, right around the end of high school, I got into Macromedia Flash. I downloaded a cracked version of it and that really piqued my interest. I thought it was just really cool that I could create something and have it animate across the screen if you interacted with it. From there, I learned how to use Photoshop because I wanted to make my own assets. Then I wanted to show my friends and put it up on the web, so I learned how to write HTML and work with FTP.

Then when I got into college, I figured I might as well try design as a major because I was undeclared at the time. I was doing a music minor, because I loved my guitar too. So I just started learning more in school and picking up side projects. Then got my first job in the industry when I was 20. I was going to school at the same time too. At this point, I had moved over here to San Francisco. I went to SF State for a couple of years. Then I moved down to LA to finish up school. That’s when I got my first job in the industry as a graphic designer at a little agency. From there I started working a lot. I started getting introduced to new types of design too. I worked with a guy named Morgan Knutson, who is an incredible designer.

I know Morgan! Great guy.

Nice! Yeah, you probably know Morgan. I worked with him back in the day. He’s always been a really great guy. He got me into CSS and thinking more about the product side of design. I basically left that job to work as a web/product designer at a small streaming company. I cut my teeth on making software, making little products for the company. I eventually left there because it wasn’t really a product company, it was more of a streaming-service company.

From there I moved to a company called Hudl, which is a sports video company, and that was really fun because they are really a product-focused company and they also build for sports, which is fun. I loved sports in high school when I was growing up. I worked with them for about a year and a half. I was remote out in L.A., and the company is in Nebraska. I learned so much there, but started feeling like I needed to get back into an HQ-setting. I think that was going to be really important for me over the long-term, over the next 10-20 years, just being back with people and getting high-touch interactions and quick feedback loops. Right around that time a few companies up here were starting to reach out and at the end of the day, I made the move over to Dropbox.


Yeah. I’m getting the lay of the land and talking to a lot of people and starting to sink my teeth into some projects. I’m excited about the company, excited about where things are going.

So did you and your wife *just* move here then?

Yes, just two weeks ago.

Oh my god. This is exciting. Fresh perspective. [laughter]

I know. I’m trying to—with this move and with things at Dropbox—keep my fresh eyes on as long as I can. I know how it goes. You get into something a few months in and you start going blind to the little cracks and details. I’m trying to keep my fresh eyes as long as I can.

Tell me about your first impressions of Silicon Valley. I’m assuming you had impressions before you were in it—did it live up to any of them? Were you surprised about certain things? What did you expect and what did you find out?

I’m not a native of Silicon Valley and San Francisco but I had come to the city ever since I was a kid and I lived here in college. So I was pretty familiar with the lay of the land, the people, the whole San Francisco vibe, versus every other city in the world. Having been away from it for ten years, obviously a lot has changed and I knew that going in. I knew that there was always an economic gap here in the city, even before the tech boom, but I think this latest boom has made it more apparent.

The other difference I see is that a city that has historically been so diverse, is looking less and less diverse these days. A lot of the companies that I’ve been at, I’m the only person of color in the entire company or at least the technical team. Looking at a larger company like Dropbox, there’s maybe only a couple handfuls of people that I might see that look like me. Seeing it at that big of a scale, opens your eyes a little bit more.

I definitely want to dig in more on all of this. First tell me, what are some of the most exciting parts to you about working in tech over the years? What things about your work have really activated you?

For me, the most exciting thing about tech is that it’s a constant march forward. Tech is just so future-facing, almost to a fault. There’s this constant retooling and re-educating that all of us in tech do. For me as a maker and a learner, it’s exciting because that’s how I’m naturally built. If I wasn’t in tech, I would still constantly be trying to learn new things. That’s fun.

What have been some of your biggest struggles and roadblocks during the course of your career?

I’d say one that I had was lack of a community, I always felt a little siloed. The university that I went to didn’t have anything for web, it was all print and advertising focused. Finding people that were interested in web/software/design was really hard.

So I guess early on that was a struggle for me, just trying to find that community. That’s something that I’ve been proactive about in the last few years, and it’s an area where I think the industry is starting to evolve and mature a little bit more. There’s just more people, so that helps, too.

Another struggle is that I’m a maker by trade. I have loved designing but it’s hard to scale your influence that way. I like to have more of a handle on the products that I’m working on, and the companies that I’m working on. So, I have to force myself out of making and designing a little bit, and try to access more of the people mentor in me. I’m being more intentional about making that transition and bridging that gap. I have to fight some of my natural tendencies to get there.

Yeah. So I would say you’re local, pretty darn local compared to most people here.

Oh, yeah.

Tell me more about what it’s like straddling those two worlds, it’s like being part of tech, and also growing up near here.

To me it’s like a double-edged sword because it is an industry that I love but I understand it’s an industry that can push out anybody that’s not in it. I was just walking home from work today and I overheard two designers talking about how they can’t afford to live in the city and these are people that actually work in this industry. How much harder is it for a firefighter or an elementary school teacher? Ten years from now does SF become a city of investors and bankers and that’s it? At some point things have to break. That’s just the way history goes.

Yeah. What has your experience been like as a man of color in tech?

Oddly enough, I’d say my experience in tech has been similar to most people. I’ve never felt like I didn’t get a job or project because of my ethnicity, but I know that’s not the case for everyone though. I’ve always run into these great people in tech, but when you look at the numbers, you can definitely see there’s something that needs to happen here.

I actually think about it most when I’m not at the office. There is this gold rush that is happening in tech and if people of color (or just other backgrounds that aren’t white and male) aren’t tooling themselves up, we can run the risk of creating a permanent underclass. So that’s something that I think about. I have to be aware and try to not just do my own thing, but also have to try and give back as much as I can.

For sure. What are your biggest motivators? What drives you?

My family… my wife, Jennifer. We don’t have any kids yet, but just being her husband, it definitely brought a greater sense of responsibility, and affects how I make decisions. I think a lot longer and plan a little bit more in decades now. Having that long vision really fuels me into pushing hard right now. Whether it’s pushing hard to just create better work or to invest more.

Another motivator is just this little ethos that I have which is: “To become better so that I can help others become better.” Becoming a better designer, a better leader, a better communicator, whatever it is. I want to level up myself in all of those areas. Not just for my own personal benefit but also to help others level up in those areas as well. That’s always on my mind as I’m reading or getting feedback or talking to people one-on-one.

What do you look for in a job now? What is¥ a priority to you in a job versus when you started?

When I started it was pretty simple: “Can I make enough money and can I do some cool stuff?” These days it’s more about “How much impact can I have—not just inside the company but outside the company?” And also “What are the quality of the people that I’m working with?” You always want to be working with people that are way smarter than you. You don’t want to be the smartest person in the room. I want to come to work not only to produce, but also to learn as well. That’s one thing that I definitely look for. Also the company needs to have strong values and opinions. The worst thing would be for a company to be middle of the road and hemming and hawing on issues. That’s something that is increasingly important to me.

How do your friends and family feel about how far you’ve come?

I’d say they’re very proud, especially my parents. I’ve got a really good relationship with my parents. They are big fans and users of Dropbox. So when they heard I was coming over here, they said, “Oh yeah, we use Dropbox! We love it!”

When I was probably nine or ten, I remember my dad and I were watching a documentary on the Selma marches. After it was done, my dad turned the TV off and he said, “When you grow up, you have to make something of yourself. Not just for me or just for yourself, but for all of them that sacrificed for you to actually be able to work wherever you want, and drink from whatever water fountain you want.” So, that’s been a responsibility that I’ve always tried to put on myself.

Also, I was named after my grandfather and I’ve always thought about these things in generations. How he came out of the segregated south with little education and no money and got his family out of there. Then my dad was one of the first to get a degree. Now I’m trying to build on their foundation.

How do you think the culmination of your background and all of your life experiences impact the way that you approach your work?

My experience growing up has made me a very adaptable person. I can pretty quickly adapt to a situation or different personality types. That’s pretty common of biracial kids and growing up in different neighborhoods. That has carried over to the workplace and my career as well, because I’ve been able to work well with a lot of different types of people and a lot of different types of personalities, on a lot of different types of projects. That’s one of the things that has helped me  from my past.

How do you feel about the state of tech in 2016? What’s really exciting to you, what’s frustrating to you? What would you like to see change?

Good question. I’m bullish on tech in 2016. Is it okay if I talk about it from a little more of a designer?

Totally, however you view it.

One thing that I’m excited about for design in tech is that I see more designers and companies that just aren’t chasing consumer tech, they’re trying to apply design thinking to a larger or more important problem. For example, I’m seeing a lot of medical startups and startups that are working to help bring communities together to petition their local lawmakers, things like that.

There are more and more designers thinking about those problems that are maybe a little less attractive, and might not make the front page of Designer News, but they’re very important problems that need design thinking. That’s something that I’m really looking forward to seeing where and how it  takes off.

What’s frustrating about tech right now? It’s very self-referential, especially when you’re here in the valley. A lot of people assume that others in the world have two and three iPhones and an iPad, and a stable internet connection, and food on their plates and a roof over their head. When we surround ourselves with only people like that, we’ll naturally tend to try and solve first-world problems, right? But, obviously those of us in tech are a very small sub-section of humanity.

As we start to shine the light on real people, and actually fill our Twitter feeds and news feeds with real life (not just tech life) it’ll make us a more rounded and better people, and that will in turn, produce more rounded and better products.

What are you working on right now in 2016? Either for work or for yourself, like, what are your goals this year?

A big thing I’m working on is being still and quiet. At my last company and even before that, I was pushing pretty hard and when I got the job here at Dropbox, I had a few weeks of downtime in between. I took that time and did some hikes. I realized that I need to recharge the batteries a lot more and be still a lot more. I’m a social introvert. I like being around people, but at the end of the day, being alone recharges me.

I’ve got some goals around prayer and meditation time this year. Backpacking trips, fishing trips. I think it’s a great counterweight to tech and it’s probably why so many people in tech are into the outdoors, because it’s just nice to be off the grid and back in the dirt [chuckles]. There’s something really primal about it. It’s just satisfying.

Cool. A little further ahead, where do you see yourself in five or ten years?

I plan to still be here in the Bay and will likely still be involved in tech. Probably not as a designer but in some other capacity. It’s tough to plan with too much detail with that long of a time horizon so you just have to stick to your principles and commit to growing yourself and those around you. It’s less about using a map and more about using a compass.

My last question for you would be, what advice would you have for folks who have similar backgrounds to you who are hoping to get into tech?

One piece of advice that I find myself giving more often to people starting out is this: continue to focus on being a great executor but don’t let that part of yourself discount the importance of being a really good person to work with. Be a good professional. Listen with the intent of understanding. Be proactive and intentional about helping others. These are skills that multiply any work that you do; whether it’s in engineering or product or design.

How we work with each other is the highest point on the pyramid. It’s also so rewarding because creating great products and services is one thing, but working with people, to me, is some of the most satisfying work that you can do in your life. Seeing someone else succeed; being able to give someone a break; connecting two people that wouldn’t have connected if it wasn’t for you; being a defender of a co-worker in a meeting; these are some of the most fulfilling things that I think you could do.