This interview is with Jessica Yuen, the Chief of Staff at Khan Academy, the educational non-profit focused on providing a free world-class education for anyone anywhere. (Download the audio recording of this interview.)

 

Q. Tell us about your background. 

A. I just turned 30, and my career path has been an interesting one. I started in electrical engineering, got a bachelor’s from UC San Diego, and then went to Stanford for my Master’s. I then made a leap into consulting, working for McKinsey & Company in their Silicon Valley office. Then I transitioned into product management at Yahoo! in their search group. My most recent move was to Khan Academy, where I am currently the Chief of Staff overseeing a lot of strategy and business operations.

Q. Tell us how your career path unfolded to where you are today. 

A. I ended up in engineering a little bit because I’m the child of two Silicon Valley parents who said, oh, you’re great at everything in school; why don’t you try engineering, the hardest major to get into, and if you decide later to do something else, you can always switch out, because it’s always harder to get in at first.

So I decided on electrical engineering and I really liked the problem solving aspects of it. But when I went into the workforce and did internships, I was having difficulty focusing on something so incredibly detailed, and I thought maybe I was just a bad engineer.

But I went to grad school regardless and ended up at Stanford in the Ph.D. program there. I luckily ran across a friend who dragged me to a consulting career information session, and there they had actually geared it toward engineers and said, “Come see the big picture and impact the world,” and they had this great pitch about what you could be doing in your career with an engineering foundation.

That really appealed to me, to be able to see things from a higher level, to understand how, in engineering you tend to be more detail-oriented working on one feature or one piece of something. And for me, I really wanted to understand how that fit with everything else.

I thought of engineering when I looked down the career path as having two “roads.” One was very technical, where you’d go into R&D and stay very technical as an individual contributor. And the other was to become an engineering manager and go down more of a business path. Given where my interests and personality lay, I thought I would eventually end up down the business management path, and consulting might be a faster track down that road.

So I pursued consulting and was lucky enough to get an offer from McKinsey, and I went there for the next few years of my career, really learning a lot about different companies and industries. It was the most amazing learning experience and probably the best first job I could have had full-time coming out of school, teaching me about interpersonal skills and a lot of other things.

Then I got to a point with consulting where, as with most consultants, the lifestyle became too much. I was traveling an awful lot, I barely saw my friends or family, and I thought I’d like to make a switch. I started to think about the things that got me really excited — the intersection of technology with my engineering background, and problem-solving and consulting skills. I thought, maybe product management might be interesting.

I had done a lot of operational transformation work while I was at McKinsey, and around that time Yahoo! was in the midst of a major transformation. Carol Bartz was there really trying to turn around the organization. So I joined a business transformation group there that was almost like internal consulting to some degree. One of the projects I worked on very early on was with Yahoo! search, and that turned quickly into a product management role.

I was lucky when I was at Yahoo! because I was able to work with people from all different departments, everything from finance and marketing to engineering to mobile — the full gamut really. And I was able to learn a ton about technology and internet search and what was happening in that space.

I was also very fortunate in that a friend of mine who was leaving McKinsey around that time happened to be coming to Khan Academy to be its president. At the time, I wasn’t even thinking in terms of my career path. I was thinking, here’s someone going into non-profit, and it’s been a long time since I’d had the time to go back to my roots of wanting to volunteer. I had been a tutor and a teacher and all sorts of things in high school and college. And I really thought the intersection of education and technology was fascinating, so I just offered to volunteer. I volunteered for a few months, which was a few months before our founder Sal Khan did a TED talk, and the growth of the website was just ballooning, and the demand was increasing really fast. And there was a natural fit for me to come into the organization and help out. So that was the transition path to my current role.

 

Q. What were the specific steps you took to switch from consulting to technology, and then from technology to the social sector

A. Great question. When I was leaving McKinsey, I really had no clue what I wanted to do. And it sounds weird, because as you get older you’re thinking your career path will narrow down. But I think when people do consulting, they feel like the career path expands, strangely enough.

So in terms of my own switch out of consulting, I did pretty atypical things. I did a bottoms-up “boiling the ocean” (as you would say in consulting) type of thing. I’d go on to Monster.com and other job sites and just see what jobs were available to figure out what I liked and what I didn’t.

It was through that process that I narrowed down the things that were important to me, including lifestyle — since, coming out of consulting, that was a big piece for me. But the other things were really about what was I going to be able to learn, and I think that’s how I slowly started to whittle down the options and figure out that I really wanted to do something in technology.

Once I figured out the space I was interested in, I just started mentioning to people that I was thinking of making a career transition. And I think in consulting, people are more open to this discussion than in industry. I was fairly open with folks that I wasn’t sure whether I wanted to stay in consulting or if I wanted to try something different. And when I would say I was thinking of trying something different, I would mention technology and that maybe I should check out what product management is like. And I would just sort of plant that in conversations to see what people would say and what advice they had.

And it actually happened very fortuitously that one of the managers I was working with on a project received an e-mail from someone at Yahoo! who was looking to hire for their team. My manager said he wasn’t really interested in the position, but maybe it might be worthwhile for me to check it out since I was considering different options.

And that’s how I ended up finding out about it. I had been looking very traditionally on websites, making a list of tech companies that looked interesting and I thought I might want to work at. I went to their careers page on their websites and sent in my resume. I probably had a less than 20 percent hit rate in terms of the responses I would get from companies.

I did a few interviews through that process, which was very traditional, no network involved. But with Yahoo!, I ended up going through my network. I was lucky that I had mentioned it to my manager, and was lucky that the person on the other side who was hiring was familiar with McKinsey and understood my strengths and how they might fit into the team. So they brought me in for an interview, and I guess the rest is history.

 

Q. How did you make the move from Yahoo! to Khan Academy

A. Well, it’s interesting as I think about careers and how other people talk about them. The one thing lately that resonated with me was Sheryl Sandberg’s speech to the 2012 graduating class at Harvard Business School. She mentioned advice that Eric Schmidt had given her when she was looking at potentially joining Facebook. She had been offered a ton of other CEO positions, and everyone asked her why she chose a COO position for somebody who was in their 20s. What was she thinking? And the advice Eric had given her was to not be so concerned about rules and titles and all of that: “If you’re offered a spot on a rocket ship, just get on and your career will take care of itself.”

I think when I was leaving Yahoo!, I wasn’t even really planning to leave. It was just that in my volunteer work, I found something I thought was really exciting, and I expressed that passion with the volunteer work I was doing. I said, look, if there does happen to be a fit, that’s great, and if not, I’d love to continue volunteering. I think there was a general sincerity on my part to just want to be a part of it, in whatever shape or form that took.

And for me, I was lucky that it turned into a full-time role. But I think it’s one of those things that I often hear people talk about when they’re trying to make a career transition — it’s finding ways into that role. Like, I’ll hear engineers talking about wanting to make a transition into marketing or something, and the ones who are successful are usually the ones who say, “I know it’s not my full-time job, but I’m just going to talk to the marketing team to see if they can use my help. On anything, doesn’t matter. I just want to understand what they do and how they do it.” And I’ve heard stories where people worked for a couple years doing stuff like that before it eventually turned into a full-time role.

In my case, I was lucky because it was only four months, it was something I was super passionate about, and Khan Academy happens to be a really, really amazing place. So this great confluence of events came together in my favor. But I think that’s one of the ongoing themes I hear when people are making carer transitions and are not quite sure how to even get started. Often, I think offering your services without even expecting anything exchange, not saying “this has to turn into a full-time role for me,” but in your mind saying, “I just want to explore this because this is something I’m passionate about” — that seems to work out at least for a number of people I’ve talked to.

 

Q. So proactivity and persistence then. 

A. Absolutely. That’s a great way to sum it up.

 

Q. What is it like working at Khan Academy, and what do you do day-to-day? 

A. Chief of Staff is a great moniker for basically “jack of all trades.” As a startup, when I first joined, there were six people in the organization. I was the first person to really be focused full-time on the non-product side of the house. So I took on everything from getting the toilet paper for the bathroom to prepping our board materials for the board of directors meetings, and everything in between — recruiting, HR, setting up insurance, liaising with our legal and finance pro bono help. I think all of that falls under my umbrella.

Before we had a school implementations team that went out and worked for the schools, the president and I would go out and actually meet with them and talk to them about what they were looking for to see if they were a potential fit for our pilot program. So it’s been a mish-mash and it continues to be a mish-mash as the organization grows. As we look for new office space, I’ve become in charge of real estate. As we look for new candidates, I become in charge of recruiting. So it’s a lot of fun, but it definitely changes.

I’m not sure there’s really a day-to-day for me that is consistent. One minute I may be talking with a potential partner who wants to offer up their content; another minute I might be helping an intern to get onboarded. And that’s just the startup world, and I think it’s something a lot of entrepreneurs get really excited by, that it’s not the same thing day-to-day.

 

Q. What has it been like to be part of the Khan Academy team from the early days to now? 

A. It’s been phenomenal, really more than I could have imagined, in all the best ways. The team we have is just amazing. I thought I worked with amazing people at McKinsey, but I must say everybody we have on the team here is just so incredibly smart, and nice, and above and beyond what you could expect out of a teammate. And the thing that struck me when I first came here, and as we’ve had people join afterward, is how easily people fit into the culture.

We’re fun, we’re a little quirky, we’re hard-working but we’re playful. And I think we love to learn; there is this culture of just wanting to know more about everything. I think that’s an ideal culture. It’s the sort of thing people talk about when you think of things like Pixar or Google, and I think Khan Academy has that too. There’s just an innovation and creativity and desire for making things better. I think that’s what’s been really fun. And as we move from the startup, scrappy, less-than-ten-person team to where we are now, it’s a lot around scalability and figuring out how to preserve the culture. How to make the systems that used to be really easy communication-wise scale up to having 50 people stay in sync, when clearly five people in a room makes it so much easier for everyone to be on the same page. I think that’s something all startups struggle with, trying to figure out how to scale.

What’s also been amazing to see is how we impact our users. One of my favorite parts of the job is just hearing from our users. We have a site, khanacademy.org/stories, where we put up testimonials we receive from our users. And it’s just phenomenal to see the people who write in and say that our product and what we’re doing has impacted their lives, and to such unbelievable ways. You hear about the grandmother who never thought she would learn algebra, and discovered the site and just decided to start doing Khan Academy practice problems every day. You see kids who write in and say they struggled for ages and had drug problems or family problems, and yet they’ve discovered this learning that’s at their own pace, where no one is judging them, and they’re able to get through school and find hope for the first time that they can graduate from college.

There’s such a wide spectrum of joy that we’re bringing to learning and the impact we’re having on people’s lives that it’s hard not to be excited to come to work. And that’s something where, in the past, I thought what I was doing was good and it was impactful, but I didn’t have this kind of joy about what I was doing. And I just feel really blessed to be here and working with a team like this. So when I think back at the last year, it’s really having an amazing team behind a great mission.

 

Q. As Khan Academy grows, how will you help the organization preserve a fun, creative, and high-performing culture? 

A. There are a lot of thoughts on that one. We’ve been really lucky on our software development side. We’ve got an amazing lead developer and lead designer who came from Fog Creek Software, which also is known for a great culture. They’ve brought a lot of the best parts of that world with them, in using tools to keep everyone on the same page.

Once we got to a point where we got so big we weren’t keeping up with each other, we started to institute weekly company updates, where we would come together, and all the team leads would give a really succinct update on the biggest things that were happening. And then as a company, if there are any big things on people’s minds, we’re able to ask Sal and our president Shantanu what they think about certain topics. That was a great way to keep the company together once we got past the size of being able to go out to lunch as a full team every day.

There are other things that got instituted, and our interns have a lot to do with that. We had summer interns last year, and our intern class is just now starting this year, and they’re a great influence on the culture because it reminds us to reset by asking how we can bring in this big batch of people and embrace them into our culture.

Last year, one of our interns had the idea of doing a “board game night,” and we thought it was going to be a one-time deal, and he was like, “Let’s do it weekly!” So we did it weekly throughout the summer, and then we just kept on doing it. And now, it’s like a staple for the company.

There’s other things we’ve done as well. We did an off-site in January. We were fearful of doing an offsite because it might be too stodgy and having everybody sitting for too long. But one of the cool things about the off-site was that we made it super interactive. We did sessions that were a little unusual. I mean, we’re a learning company and we’re a tech company. So we wanted it to be very reflective. We did it at the Computer History Museum in Mountain View. And we did activities with our various teams to get everyone excited — we did brainstorming, goal-setting, brain-teasers — and it was just a great day for the team to bond, get together, and reset on vision and what our culture was like. And those are the things we continually try to look at and influence throughout the organization but in a way that’s natural and not forced.

One recent example was that we wanted to name our conference rooms, and we decided to make them puns. So right now I’m sitting in our conference room named “Cognito,” so I am “incognito.” Our kitchen is called “Sync,” so we’re all “in sync” when we’re eating. I mean, every company needs to name their conference rooms, but we said, let’s make it reflective of us. We’re just a little bit silly like that.

 

Q. What do you most wish you could change about your experience? 

A. I’m not sure there is much I would change. I think the one thing I would love to figure out how to do better is that there are certain growth spurts, like when you get past ten people, organizations feel a little bit of a strain. Then when you get past where Khan Academy is now, at 35, there is another strain.

And everybody knows it’s not anybody trying to make it more difficult, but it just naturally happens. If I had a magic wand, I would love to figure out some of these processes around scalability, if we could do it more easily.

For instance, we instituted company updates, but it was only after figuring out, “Oh, I haven’t seen this person for ages. I wonder how they’re doing?” And “I feel like I haven’t talked to this person for a while.” It was only after we had a little bit of tension around it that we could figure out the right solution. I almost feel like that’s a natural part of the growth process, as opposed to something that I wish could go away.

 

Q. What do you see yourself in the future? 

A. I can honestly say I really love what I’m doing now, and I hope to be able to stay with Khan Academy for the foreseeable future, because it’s a unique organization being a non-profit but still acting like a tech startup with an amazing mission. I don’t know where else you can find that.

So in the future, I’m not sure where things lead. If I had talked to myself ten years ago as an engineering major, I wouldn’t have guessed that I would end up here. I wouldn’t even have guessed I would end up in consulting — I didn’t even know management consulting existed yet.

So I think, for me, part of it is continuing to talk to people, and read about new things, and find out what other roles exist, and take it from there. It’s not really career planning so much as career exploration and finding things that are interesting.

 

Q. What advice do you have for people who are interested in exploring some of the roles you’ve had? 

A. One of the best things I’ve learned, having been on the recruiting side, is to just excel at whatever you’re doing. Find something you enjoy and try to excel at it as best as you can. I think that passion comes through. And it doesn’t necessarily mean from an academic “straight As” point of view. It’s showing that you have passion for what you’re doing.

I mean, one thing we look for when we’re screening resumes is people who have side projects, who do really interesting things in their spare time. We ask things like what hobbies you have, what groups are you part of outside of work and outside of your friends.

I think that’s increasingly becoming an indicator of how well a fit you’ll be for an organization’s culture. And a lot of it is just who is going to be the person who goes above and beyond. It’s not required, it’s not something you do because school says it, or your parents say it. It’s something you do because you are just interested in it. Those are the people who are going to be the best to work with, both from a productivity standpoint, but also just because if I’m passionate about my work, I want to work with people who are passionate about their work, too.

People use this word “passion” a lot. And I used to think it meant having to be zealous about something, where I couldn’t imagine myself doing anything else, and breathing it all the time. But it’s really something that is just enjoyable in the same way I like to read a good book on the side, or watch a TV show, or hang out with my friends. I think it’s fun to come to work, and it’s something I enjoy doing. And I think it’s really about identifying a role where you can feel that way.