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Interview: Jessica Ko (Playbook, Opendoor, Google)
Breaking into product design, learnings at Google, joining the founding team at Opendoor, and now becoming a founder.
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Jessica Ko is a Co-Founder and CEO at Playbook (playbook.com). Prior to founding Playbook, she was the Head of UX & Brand Design at Opendoor where she joined as a founding member. And before that, she worked at Google/YouTube for 7 years.
In this interview, we talk about Jessica’s career into design, learnings from startups & big tech, and becoming a founder.
I hope you enjoy & let me know if you have any feedback via Twitter @thetkkong.
TK: How’d you get into design?
Jessica Ko: Yeah, so I discovered design back in probably about 2010. Before then, I had no idea what design was, I didn't know what UX was. And back then, a lot of people came from engineering or computer science backgrounds. I think it was because UX was not taught in school back then. And it was not a popular field.
It’s a brand new field. And nobody really understood what it was then. So I got into Google, and I was developing web pages for Google and also designing at the same time. And then, I discovered there’s a whole department called UX and Irene Au at the time, was the head of UX Design. I really wanted to get into this field.
So I ended up building a ton of prototypes for UX designers outside of my full-time job. I was working evenings and weekends and spending hours and hours, just building prototypes for them. I'd like to say that I was Google’s first prototyper. Because prototyping wasn’t actually a thing back then. There was no Principle or ProtoPie. This was a time when we were designing everything in Photoshop.
TK: How’d you end up convincing someone at Google to formally move into Design?
Jessica Ko: I didn’t ask for it right off the bat. It was more kind of a gradual thing that I kind of squeezed myself in there. I didn’t go straight to Irene Au saying that I wanted to be a UX Designer. I wanted to be useful to the team first, and show my value to the team. It took me almost a year, almost two years to actually move. Eventually, I got into their team but it was because both sides wanted each other.
TK: What was your biggest takeaway from designing at Google/YouTube?
Jessica Ko: It’s one of those things that you don't feel like you're learning a whole lot until you left the job. It looks like a big mess when you’re in the middle of it but then you realize “holy crap, I actually have grown quite a bit as a designer.”
When I left Google, I realized how much I learned about the UX process. We went through so many sprints and there’re so many different types of UX processes. I got to see designers who come from Microsoft or Apple and see their processes. It’s a place to see where you get to see everyone’s how they work, how they operate, what they are like, how organized they are, and their whole process.
TK: You then left Google to join the founding team at Opendoor ($OPEN). How did you know it was time to leave Google?
Jessica Ko: I was at Google for 7 years, and on different teams inside Google. You learn a lot of different things by switching teams. When I left Google, I wanted to explore something that’s different from Google. I wondered, what is it like to start a brand or product from scratch? I felt like I could design stuff on my own, beyond Google. I wanted to get out of my mothership and experience truly what designing from scratch would feel like.
TK: How’d you choose Opendoor? What was your framework to joining an early-stage team?
Jessica Ko: It’s actually super complex. And looking back, it’s not as simple as “Oh yeah, it looks great and I think they have a promising future so I’ll join.” No, it’s much more complex than that.
Six months before I left Google, I was actually thinking about leaving already. It took a bit of a while to look for the right startup join and even considered founding my own startup back then. But it turns out that something happened, it’s a serendipity. You hear about it from someone else, and find out that they do real estate which is one of my passions. It’s just a brief moment that you’re like “Hmm, I’m very interested to find out more” and then you meet one of the co-founders of Opendoor. I met JD at a coffee shop and just liked the guy a lot. I didn’t hear what their product was or anything like that but something about real estate drew me so into it. So then afterwards, JD invited me to their “office” and then in the corner somewhere there were 5 guys: Eric Wu, Ian Wong, JD, Ryan Johnson, and Nolan. That’s when I met Eric & Ian and they didn’t know how to interview designers back then so they made me design in front of them and I pulled out my Photoshop and did something.
At that point, some designers might be like “What is this whole design interview process?” but I was more fascinated by it. Similar to how I discovered UX Design and was drawn into it, I wanted to learn more about Opendoor. I really liked Eric and Ian and I felt really comfortable. This is where it’s really complex. It’s a lot about the chemistry. I met with a ton of founders back then but I could see myself around this group.
TK: From your experience with building the design team at Opendoor, do you have any advice for junior product designers?
Jessica Ko: We tend to evaluate junior designers very differently than mid-level designers. I think a perfect spot for designers for their career is somewhere between 3-7 years. It’s like a sweet spot. Even if designers come out of UX schools, the first three years is slightly difficult actually. So when we bring in junior designers, we care a lot about our ability and willingness to train and teach them. It takes 10,000 hours to be a decent designer. I say that about myself too.
TK: Yeah, that’s good feedback. It’s important for young designers to have a growth mindset and the willingness to learn quickly. Especially at startups when the company is growing so fast and everyone’s bandwidth constrained.
TK: How has it been being a Design Founder?
Jessica Ko: The good thing about being a design founder is that our team hasn’t hired a designer full-time yet. Our team is mostly engineers and I feel like I could guide them. So it’s intentional that I don’t hire designers right off the bat because I want to truly train or teach engineers how to think like designers. They’re using muscles in their brain that they haven’t really used before and getting them to constantly flex and stimulate it.
TK: Do you have any advice for aspiring product designers?
Jessica Ko: I love designers who are from non-traditional backgrounds like engineering or psychology or customer service. They bring in new perspectives. I hope school or age doesn't discourage them from entering the field. UX is something that gets better if you combine multiple two or more disciplines. Because UX is about understanding the psychology of our users, the more perspectives you have the better you get.
I hope you took away some learnings from Jessica’s inspiring career! Which designer would you love to have on the interns.design Newsletter? What are you curious about when I interview designers? Let me know via Twitter @thetkkong or reply directly to this email!
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