“Paying it Forward”: An Interview with Amy Yin, CEO and Entrepreneur

It’s 8:00 a.m., and pushing open a clear door with espresso in hand, you arrive at the company office for the day. With rows upon rows of cubicles, the office’s muted color palette and the distant conversations of colleagues incite a calming but uniform atmosphere. To some, this structured routine may seem monotonous, but Amy Yin is working hard to change the way the world thinks about company space.

Through the #StopAsianHate Essay Contest, an effort organized by NYU Stern alumna Gloria Li to raise awareness about anti-Asian violence, I was given the opportunity to talk with an influential Asian American entrepreneur who spotlighted her voice in order to uplift and represent the community. This person is Amy Yin, Harvard graduate and CEO of software company OfficeTogether, which she developed to facilitate the transition into a hybrid workplace for companies. She also previously worked as a software engineer at Facebook and Coinbase, and as a Girls Who Code volunteer instructor.

Yin, whose parents immigrated from China, grew up in a town of about 15,000 people in Wisconsin. Her town was predominantly white, and, as the only Chinese American girl in her high school, Yin never felt like she belonged culturally. It was only after Yin started college, where there was greater diversity in the student body, that she really embraced her identity and heritage and no longer felt pressured to be similar to everyone around her.

Yin, who is currently visiting her parents in Wisconsin, graciously hopped onto a Zoom call with me to discuss her experience starting her own software company, how her identity as an Asian American woman intersects with her work, and everything in between.

SC: What sparked your initial interest in the career you're in today? As you mentioned, you majored in computer science and later concentrated on software engineering and business––when and why did you decide to make that change?

AY: When I went to Harvard, I left Wisconsin, where I had grown up, and in my first year, I thought I was going to do applied math economics. I really wanted to become an investment banker, since working in management and consulting seemed like what all [my] peers were doing at Harvard. Then, in my sophomore year, my boyfriend took an Intro to Computer Science class, and a lot of other people were doing it, so I said, “Okay, why not? Might as well check this out.” And I just fell in love with programming. I thought it really matched my way of thinking, and I found the class to be very engaging. And so I decided to become a more technical investment banker, and I could do M&A [Mergers and Acquisitions] for software companies. So I decided to make the change, since […] computer science gives me the ability to build.

SC: I saw that OfficeTogether uses various apps or platforms and implements daily health checks to make hybrid or asynchronous work in the pandemic as seamless as possible. Could you explain more about how OfficeTogether works, and the impact you aimed to make through the software?

AY: OfficeTogether is here to help companies develop and manage the office of tomorrow. Instead of imagining rows and rows of desks to sit in every single day, we are reimagining the space to be more flexible and a place to see other people and socialize, which is a really big departure from how office work used to feel. People used to think that you need to be in an office to get work done, and the pandemic has proved us wrong. OfficeTogether does scheduling and reservations, so you know who is going to be in the office, since the main motivator of going in is to see your coworkers. The impact we want to have is that we want to make it easy to have a flexible workplace while still maintaining the best elements of in-person collaboration. We still think there’s magic in these in-person relationships, but it doesn’t need to be five days a week anymore.

SC: What do you think are the basic steps of starting a startup company?

AY: Number one, you want to feel mentally ready for the journey of an entrepreneur. You’re not going to be making that much money at first, and there’s no structure, and no one to tell you what to do. You have to write your own playbook. You have to be really excited about taking a blank canvas and not having any paint. It’s having to get your own blank canvas, figuring out whether you want paint or crayons, or whatever your medium is. And for some folks, that’s absolutely terrifying. For me, on most days, it’s absolutely terrifying, since no one is my boss and there’s no one to tell me what to do. But I also love it. So the number one thing is to want to have this experience of just creating from scratch. And after that, the rest of it is just easy. You start to look for an idea, test some hypotheses out, you talk to customers, and figure out what actually has market viability, and at some point, you build a team and raise some money. All of this stuff is easy; the hardest part is wanting to have the experience of having no clue what’s happening every day.

SC: What is a typical weekday as the CEO of OfficeTogether like?

AY: It really depends. [In terms of] my job as a CEO, I see it as four things: 1) To keep money in the bank, 2) To build a really great team, 3) To set a vision for the business, and 4) To make sure the company is operating at a high level. And whenever I can, I try to hire people to handle any specific issues happening. For example, when I first started, I was really focused on fundraising. And then, once we had money, I was really focused on building the product, and finding the initial customers. Then, I realized that I really need an engineering team, and so I just became a world class recruiter. I spent a lot of time hiring and talking to engineers, helping manage the product and the day to day, like a product manager. Once I built a really great engineering team, I shifted to sales, and I became a really great account executive. I learned how to close deals and pick new customers. And now this month, I’m really focused on marketing, because I’ve hired a sales team, so I can now focus on top of funnel and lead generation and getting OfficeTogether in front of more people. And so the CEO’s job is very dynamic. Now my calls are all about marketing, but if you asked me a month ago, I was mostly talking to customers, signing contracts, and going through security reviews.

SC: What are some challenges and opportunities relating to recognition and sponsorship that you feel are unique to AAPI professionals?

AY: In Silicon Valley, there’s actually a lot of Asian founders and entrepreneurs. I don’t feel underrepresented as a founder in Silicon Valley. I do think that among successful Fortune 500 CEOs and founders, you see a lot less Asian representation, but because there’s such a heavy representation of AAPI [people] in software engineering and the tech industry, we’re not really underrepresented in terms of who gets funding in Silicon Valley. Some of the things we have done, for example, was that I really wanted to get more Asian Americans on my cap table–– more investors who are Asian American. And so sometimes, I’ll find investors that invest in me because they want to support another Asian American in the industry, but I also have a lot of Asian Americans on my cap table already, so I don’t feel discriminated upon because I’m Asian; if anything, I feel more discriminated upon because I am a woman.

SC: So along that train of thought, have you ever encountered any restrictions or challenges that come with being an Asian American businesswoman particularly?

AY: I definitely feel that being a woman has made it harder. So, for example, even though I’ve been a software engineer for over ten years, I’ve had an investor tell me that they thought I was a marketing person. They said from my LinkedIn that I looked like I was from marketing, but no one would look at my resume if I were a man and think that I was a marketing person. I have a computer science degree from Harvard, I was a software engineer at Facebook and engineering manager at Coinbase. And so I think that because I don’t necessarily fit that mold, that mistake is more easily assigned to me. People have an image of what an engineer looks like in their mind, and when I break that image, it’s hard for them to reconcile.

SC: How have you addressed these situations of implicit bias toward businesswomen?

AY: I think your qualifications are not as important when you are a founder. A lot of it is swagger, and just going for it. For me, I spend a lot of time working with coaches, and I definitely have some imposter syndrome, and I don’t think that’s in just women or AAPI, but we may have it in larger percentages than our white, male counterparts. But I know for me personally, sometimes I just feel like I’m not good enough, or I’m faking it ‘til I make it. And everyone to an extent feels that way, so I have to just remind myself that we’re here for the journey, here to build an amazing team, and [to] lead with curiosity. That no matter what the outcome is, I will have had an amazing time. Another thing I try really hard to do as a founder is to help other founders out. I always set aside a few hours a week, especially for women founders, to help them, because so many people have helped me along the way. Paying it forward is super important to me.

SC: What do you think are the most important skills that make a leader in your experience?

AY: The desire to be a leader. You see yourself, and you make your identity as someone who wants to uplift and support other people. So for me, leadership is all about doing through others, and helping scale yourself to other people. I believe a lot in servant leadership, where my team is not here for me, I am here for my team. I elevate them so they can stand on my shoulders and do more on their own and also help limit me. You can also be a leader without a title, and the most important thing is the desire to lead. Doing it from a place of curiosity rather than a place of selfishness also tends to drive better results.

SC: What are some tips you have for students who are considering pursuing business in college and beyond?

AY: I really recommend that everyone take some computer science classes. No matter what business you are building, there is going to be a technical or software element of it. And so by not understanding tech or being able to talk to software engineers, you could leave yourself behind. I used to teach for GirlsCode, and I built the Harvard Women in Computer Science program. I really encourage people to not get your MBA in Business and study that in college, because you can learn all of that stuff on the job. The things you really need to learn in college: Learn some technical skills, and learn how to build something, because business is about building, not about just pushing numbers around. We don’t even offer Accounting at Harvard, and people just learn it on the job or get a Masters. The most important thing from my classes is that I learned how to code. The rest of my learning was done on the job, through apprenticeship. I would really encourage you to take some computer science classes and recognize that you’re really not in college for the classes, but to learn how to learn and network and meet amazing people.

SC: What was the best advice someone has given to you about being an entrepreneur?

AY: Some advice from my coach that has really helped a lot is that if I take myself too seriously, I will end up with less creative results, since it takes out all the fun in life and dampers the ability to think outside of the box. It might seem serious, as you’re raising millions of dollars and people’s careers are on the line, but it’s actually not that serious. Whether my company fails, or someone gets fired, or I get fired, the world is here for my learning and my growth. And when I truly believe that, I light up. I feel superhuman.