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Jossy Lee, MBA ’12

Jossy Lee, MBA ’12, joins Christopher Reichert, MOT ’04, to share how her time at MIT Sloan has impacted her current work as a founding member of the New England Innovation Academy, the first middle and high school using human-centered design to prepare future innovators. She is also the founder of Woom, an incubator dedicated to nurturing working moms, and author of Mommy Goes to Work, a forthcoming storybook celebrating working moms. 

Sloanies Talking with Sloanies is a conversational podcast with alumni and faculty about the MIT Sloan experience and how it influences what they're doing today. Subscribe and listen on Apple Podcasts, Google, and Spotify

Christopher Reichert: Welcome to Sloanies Talking with Sloanies, a candid conversation with alumni and faculty about the MIT Sloan experience and how it influences what they're doing today.

So, what does it mean to be a Sloanie? Over the course of this podcast, you'll hear from guests who are making a difference in their community, including our own, very important one, here at MIT Sloan.

Hi, I'm your host, Christopher Reichert, and welcome to Sloanies Talking with Sloanies. My guest today is Jossy Lee, a 2012 graduate of the MBA program at Sloan. Welcome, Jossy!

Jossy Lee: Hi, Christopher. So glad to be here.

Christopher Reichert: Great to meet you. Jossy co-founded—among other things, I'll give you a bit of a background Jossy—she co-founded the MIT Sloan Design Club to equip students with design thinking methodology to solve problems creatively, and has been on the founding team of six companies before Sloan and after Sloan. After Sloan, she became the inaugural Director of Product Innovation at EF (Education First) the world's largest international education company based here in Cambridge. It's a beautiful building, they have that waterfall glass effect on the front.

Jossy Lee: Yes. Right across the street from the Science Museum

Christopher Reichert: Yeah, that's right. And a piece of the Berlin Wall.

She was director of new business at Chineasy, an award-winning edutainment company, working to revolutionize Chinese learning. She has advised on strategic initiatives and education innovation for MIT Open Learning and has coached, and I don’t know if you continue to do, global entrepreneurs at MIT Bootcamp. So there's a strong entrepreneurial thread in Jossy's background and the work that she's doing now.

Jossy and her team now are innovating to enhance the experience of working motherhood through an incubator called Woom, which I think is a clever play on sound. And their first offering is a modern picture book, Mommy Goes to Work, which I actually have here right next to me, celebrating working motherhood, along with the various stickers as well, which look great. It's a really nice visual.

So she thought of this book years ago when her young son asked her about a presentation she was giving a work and she thought about it and likened it to his show-and-tell at school. And so putting her design thinking process to work, she developed it through a human-centered design process and testing it with over a hundred mothers around the globe and their communities to refine it. And she's also part of an operating team, sorry, part of a team opening a new school, New England Innovation Academy, the first human-centered design middle and high school in the United States. So welcome Jossy, that's a lot going on!

Jossy Lee: Just launching a new book and opening a new school, just a few things.

Christopher Reichert: Yeah. And raising a few children.

Jossy Lee: And raising a few children. Yes. Well, thank you Christopher, that was a good one, I'm honored.

Christopher Reichert: So, you're originally from Taiwan. Am I right?

Jossy Lee: Yes. Taiwan, Taipei.

Christopher Reichert: And I noticed by the way that your book was published in Taipei with soy inks. So that's a nice touch to your home country?

Jossy Lee: Yeah. It was manufactured in Taipei with soy ink, we made a very conscious decision to be environmentally friendly.

Christopher Reichert: That's excellent. So your background is littered with founding member and co-founder, consultant and things like that, coach, so a lot of independent activity. So what drives you to forge your own path?

Jossy Lee: Yeah, that's such a great question. I didn't realize this until a few months ago when someone asked me and then she said, "Oh, so you had this ‘employee number one’ career tack." I was like, wow, actually that's quite right. I didn't think about it this way. I've always just loved doing things that no one has ever done before, something new from the scratch, something that I am passionate about and has a purpose in the world. And really just the MIT spirit of innovation, idea to impact, so that's what drives me. Something that's between 0% to 60% is really where I thrive the most. I'm not extremely strong in scaling between 70% to 99%. I partner with someone who is strong on that.

Christopher Reichert: Well, that's a great insight because I think a lot of founders, founder on that, on those rocky shoals, which is the operational side. Whereas, you've had the insight to yourself that you're more of a startup person and you want to hand the operations side off to other people. Was that something that you learned through some experience that left you dissatisfied?

Jossy Lee: Yeah. You know what, I think Sloan helped me understand that actually. So before Sloan, I was the employee number one of the first social venture fund in Greater China. So actually, we translated the word social enterprise into Chinese, that's what we did. And then we were the first in the market investing in business with a social mission. It wasn't that clear to me, it would just, I got really excited about that opportunity of something no one actually has done before, so I gave up a big offer from an international a company, and then to join that, something no one has ever done before.

And I didn't realize that until when I was at Sloan, we have this Communication for Leaders class, and then we're doing characteristics tests of what kind of person you are on the team. And I remember the one like six characters, which is initiator, resource investigator, strategist, executor, finisher, and team facilitator. And the professor at Sloan said, "No one can be as good as all those six, you have to be better in somewhere between two or three, four at most." And my data shows that I'm really on the front side of strong initiator, resource investigator, and then strategist, team facilitator too. The executer and finisher part were lower score. So that helped me in a data-driven way to see who I am and what my strengths are.

Christopher Reichert: That's a great insight. Yeah. So how did you choose Sloan?

Jossy Lee: That's a good question. Actually, I was reflecting on this this morning, Christopher. I have an official answer and I have an authentic, not so official answer I don't think I've told anyone yet, but I think this might be a good decision.

Christopher Reichert: Excellent. I would love to hear both and let's see, maybe there's a truth in both, right?

Jossy Lee: Yes. The official answer is very true as well. So I was looking for something that aligned with what I want to become, so entrepreneurship and innovation and Sloan definitely was on top off that list in the business school.

The second reason was I come from Taipei, this is my first time spending time living in the States, well, that was my first time, I thought I be here for two years, and then now what, 10, 11 years later, I'm still here. So I wanted to be in a city where I have different things, people to participate, to get to know so that I could get a better sense of the U.S. culture and what it is like to live in a different country. So a school in the city was preferred.

Third, which is most important one, is the people and its culture because I know myself, I know that I learn the best from people who I surrounded myself with. So I was really intentionally choosing a collaborative culture and people. So that was the official answer.

Christopher Reichert: That's the official answer, but what about the one you've been contemplating?

Jossy Lee: Yeah, so the real answer was, Sloan was not even on my list when I was applying, because I had this assumption of Sloan and MIT was technology-minded and it's all about technology. And back then, I wasn't the person who was enthusiastic about technology, I was very much passionate about people.

So in April the year that I applied, me and my friend went to San Francisco to see the two schools, went to Chicago to see the two schools, and we went to Boston to see the two schools. And we spent an entire day at Harvard Business School and we have one more day before we return to Taiwan. So we can choose either to go to MIT Sloan for a day or to go to Quincy Market for the lobster roll. Then so my friend asked me because she doesn't really have a strong opinion, she asked me, where do I want to go? I said, of course, Quincy Market, I love lobster and technology is not my cup of tea. So we went to Quincy Market.

So we left from Boston without seeing Sloan, I feel embarrassed about telling you this story every time, and we returned, sat my GMAT and everything and it's December. So about a few weeks away from Sloan's deadline. And then that's when something happened that completely changed my mind and I applied to Sloan instead.

So it was an evening that I signed up for an info session for a peer school and I was already on the way my friend told me, “oh, don't come, the hotel room is full already.” I said, "Ah, I'm already on the way. So where are you guys doing now?" And they said, "Oh, MIT is doing an info session at a bigger hotel across the street, so you might as well just come.” I said, “oh, okay,” since I'm already on the way, so I go. So when I went there, it completely changed my mind. Rob Garcia was there. Rob Garcia, in Admissions had for many years, I don't know, like 20, 30 years at Sloan, he just retired this year.

Christopher Reichert: Legendary.

Jossy Lee: Legendary. And he turned out to be my interviewer as well. And then there were, if not 20, at least, definitely more than 10 alumni, from someone who was a current student, who recently graduated, to someone who had graduated like 20, 30 years ago. So it was a very diverse spectrum in terms of what they do. The common thread was really entrepreneurship, innovation, and a down-to-earth spirit, and a sense of community, which was really different from what I experienced from other school’s info sessions. It's usually current students and a new grads. And what they shared that night was just totally mind blowing and exactly what I was looking for. And I blamed myself for being so dumb and make a silly assumption of, this is just about technology and I thought I wasn't interested, but now I will tell everybody, if you think you're not interested in technology, then you just tell yourself you're not interested yet. It's everything.

It's hard to be immersed in such a creative and entrepreneurial, innovative environment, passionate about technology and after two you say that you're not interested at all. I definitely am a lot more enthusiastic about technology now than before. And I know actually technologies are all about people's needs too.

Christopher Reichert: That's great. So you arrive at Sloan and what courses did you take and what do you wish that you had taken?

Jossy Lee: Yeah, that's a very good question. The one course that had the most influence on what I'm doing right now is probably Product Design and Development. So in that course, we had 60 students in the classroom—20 of them are RISDI designers, 20 of them are MIT engineering students, 20 of them are Sloanies. And during the semester we went from nothing—no team, no idea, nothing—to team, idea, different version of solution, different version of prototype, eventually at end of semester, we have a sellable product prototype, a business model, and a great team that's really interdisciplinary. So that really was instrumental in what I'm doing now, mainly because I started the MIT Sloan Design Club inspired by that course I took. I got to know Matt Kressey, who was a teacher for RISDI, in that class and later MIT hired him into MIT to start the MIT Integrated Design and Management program. And Matt Kressey is also on our funding team of the new school that I'm starting now. It's the first school that prepares students to shape the world through a human-centered design methodology.

Christopher Reichert: And I think you've brought up an interesting insight there, which is how one thing leads to another. Where you now have on your advisory board, did you mean or funding?

Jossy Lee: Funding team. Yeah, so I'm really the employee number one of the new school. So started two years ago, brought in by the founder and prepared the school all the way until now. So we're opening this fall with almost 80 students, day and boarding, 6th through 10th grade.

Christopher Reichert: So tell us about that process. I mean, to go from an idea to actually a bricks and mortar with classrooms?

Jossy Lee: Wow. You mean two years of planning in 30 seconds!

Christopher Reichert: There you go, I'll give you 28.

Jossy Lee: Okay. Wow! It was actually the part that I loved the most, as I was brought in by the founder, they want to start a new school that the world needs next. So we went through multiple version of worship and discussions. The founders, the three of them, were all successful entrepreneurs in nonprofit education and business before they came together to start this new educational venture, in a way new school.

So we know that innovation is important and so when we had the theme, I immediately thought about Matt Kressey, who was my teacher at MIT. So I reached out to him and invited him to join one of the workshops. And he and the founders, he introduced the human-centered design concept to the founders, many people called it, design thinking. And then the founders were fascinated about innovation. It can actually be a structured process, it can be learned and then it's empathy-driven and then it's interdisciplinary.

So they had a very good first meeting and we kept inviting him back for our discussions and together we shaped the vision of the school, which is prepare the next generation of innovators who passionately pursue their dreams and shape a better world. So we go from there and started to build the team, find the right head of schools. And then, so now and teachers and administrative staff together, we have about 40 team members.

Christopher Reichert: That's fantastic. How much of the product design class and design thinking did you apply to the process, particularly when things in the early stages, or even throughout, weren't very clear on how to solve the problem or even define the problem?

Jossy Lee: Yeah, we rigorously, I mean, rigorously, we did extensive research into human stakeholders. In the process we interviewed students of all different profiles, students, parents, educators, and just stakeholders in the school’s world. And then, so that process took us more than half a year to collect data, understanding the insights. And then we use a lot of post-its and then do a lot of synthesizing, brainstorming from there. And then from there, we got to our principals, so I talk about our vision, our mission is, we summarized into PIM—passion driven purpose. We want to prepare every student to understand their passion and go out to develop a purpose that's helpful for the world. We borrow from MIT innovation, the definition of innovation, idea to impact, and the “N” is ready for what's next. So if you look at our school logo, New England Innovation Academy, it's really a pin shaped with many dots forming it.

So throughout that process we developed how do we want to achieve this vision and mission? And then we found out its three things. It's the future focus curriculum. Everything we do is to prepare students for the future and not for the past. Human centered design, obviously we have an in-house expert who is now our Head of Innovation, Matt Kressey. And then the third is real-world inclusion, so ideally we be able to school without the walls, the students are learning and doing projects with industry, community, environment, governments, very hands-on, a lot of making and entrepreneurship in that.

Christopher Reichert: And how are you recruiting students? I mean, as a parent, well, really as a human, change is hard, particularly when kids have one go at their middle or high school. How do you convince parents and students to come and join?

Jossy Lee: Yeah, I think we are looking for mission correct families, parents and students. What we found is, when we have the team, we had a fantastic cohort of teachers and staff. And so the best way is actually regardless as to how much we talk, they visit the school, they meet other kids who will be on the school, they meet the teachers who will be with them and feel the vibe, it was an easy sell from there. So that's what I heard from our Dean of Enrollment. Yeah, so I think when it comes to school, it's really the community and same goes to Sloan as well. I talk about the people and the community, a collaborative culture are really what drives people to us.

Christopher Reichert: And so that brings me to Woom, which also sounds purpose-driven and collaborative. So tell us about that incubator.

Jossy Lee: Yeah. It's such a good question. Now, I'll be super honest with you, Christopher, I'm still in the process of inventing the incubator-

Christopher Reichert: Fair enough.

Jossy Lee: I didn't start at wanting to do an incubator for working moms, to be very honest. I started wanting to create a solution for my own family's drop-off problems. I was raised by a super wonderful full-time mom, my mom's passion and purpose really is what it takes to be a wonderful full-time mom. So when I realized, probably in my college, that I’m very career-driven, but also want a family, I started to, I don't know how people make this happen, because I didn't grow up having any role models. So it was really when my son was born and then this, every morning the drop-off was really tough, starting end of maternity leave. The first day we returned to work, I was like, oh, I'm giving my four-month-old son to someone I don't know, for a selfish reason. So it was this mommy guilt constantly there.

And then when my son was older, the tears, the separation anxiety didn't help at all. So I was really searching high and low wanting to find a resource that can facilitate a conversation with him about what I do at work, why do I work, and also to spark his imagination about what he can one day be. So I couldn't find such a thing, so I created.

Christopher Reichert: Yeah. I have very strong memories of my daughter's going to school as well, where the whole process of first getting out of the house and then actually leaving them behind, took years to get it right and not feel guilty, so.

Jossy Lee: And then you asked about how the human centered design process has shaped us, we did go through the entire human centered design process with this book as well. So I started from one book and tested this book with literally more than a hundred working mom and people in their tribe across the globe. And we took everything from storyline to character design, to even the book size, everything. And it was from this process, people inspired me that actually, mommy doesn't just work in the office, mommy works in everywhere. So that's the reason why we are bringing this series to new careers. We are going to develop Mommy Goes to Work in different places, in the hospital, in the labs, in the courts, in outer space, in the White House, in the army. So we want to do a series of books celebrating different working mothers and strengthen bonds between their families.

Christopher Reichert: That's excellent. And you also mentioned that there are companies who are looking to customize the book for mothers or parents returning from maternity/ paternity leave?

Jossy Lee: Yeah, I think that's a very cool idea. And we're in the process of doing that. And then we also welcome companies who want to show your employees that this is a family-friendly workplace and then we recognize you as a whole human being. I think this will be a very heartwarming gift to your employees. Think about if you get this on the first day you return to work for maternity leave, I think the employee will be very touched by this.

Christopher Reichert: Yeah. I mean, it certainly does suggest that the organization that they're returning to gets the challenges that exist outside of the workplace, which could be heartening.

So if you think about your time at Sloan and so you took a product development class, are there any classes that you wish you could have taken that you didn't get a chance to take?

Christopher Reichert: Yes. So I didn't take, I wasn't able to take the E&I Trek entirely, actually because the Silicon Valley Trek conflicted with my sister's wedding. So I had to choose one to go so I took the first few classes and then I told the professor I wasn't able to make the trip and it was a requirement. So yeah, I wish I had done that.

But looking back, if you ask me what would I do differently? I wish I spent less time with the problem sets and spend more time with my friends in the cafeteria, or just getting to know each other and spending time with each other, to attend those talks that happened in the lunchtime with all the cool founders and cool business professionals coming into share. For some reason at that time, I was the younger one. I was 25, so I was the younger one in my cohort and I constantly feel this urge of I need to catch up. And I constantly fear about being behind, so I wish I had a different mindset and enjoyed it better.

Christopher Reichert: That is funny, how people think about that, I totally understand what you mean. When I was doing the Sloan Fellows program, I felt like I was on the older side and I thought, wow, how does it, everyone here is more nimble than me on whatever topic it might be, so we all come at it from different angles. Right?

Jossy Lee: Yes. We all have knowledge.

Christopher Reichert: Exactly. So with the academy starting in what? This week, next week? What's your involvement with that and what's the focus?

Jossy Lee: Yeah, so we have a great team of educators, we have a great team of administrators. So as employee number one here, I'm really overseeing the growth initiative. So two years ago, I was envisioning what the school would be today. Now, we have a great team making that happen. I need to make sure what happens day-to-day aligns directly to our mission and then also looking forward, two years from now, five years from now, how might we grow into and keep just building up things? So in the past few years, my major responsibility was build and transition and that's what I really enjoy doing and what I'm good at. In our internal Slack, my nickname was “Jossy Next Step,” because I'm always the person who was thinking about. So, it's really like a glue and engine in many ways, so I love that role.

Christopher Reichert: So you're constantly driving forward to, okay, that's done what's next. Right?

Jossy Lee: Yeah.

Christopher Reichert: So how do you manage the uncertainty and risk with startups? There is certainly something compelling about going to an organization where you're guaranteed a paycheck and you have a ready community of colleagues and operations and processes. With a startup, you're creating all of that from scratch and so there's the uncertainty of not only bringing the idea to life, but also the uncertainty of the rest of your life, how that fits in, whether it's financial or time commitments.

Jossy Lee: Yeah. That's such a good question. I don't know yet. Just kidding. I do have some key takeaways from this, I think the most important thing is mindset wise, I know this is a process, so treat the problem as the way scientists are looking at the problems. So everything is an experiment, we're constantly iterating forward, so testing iterating, testing, iterating, instead of thinking about, I'm having this big launch and then this is it, let me prove the world that I was right. That I think puts a lot of stress on you and it also prevents you from being open-minded about finding what actually was right. So having that mindset and our leaders are fantastic, our Head of School, our Head of Innovation, our founders, they gave us open permission to fail.

Literally, two days ago, when we were having the orientation of our internal staff, they were like, you have the permission to fail. If we don't fail, it means… have a small fail, and learn, just not keep doing that. So I think having that culture in the school is extremely important, especially we're a school that prepares innovators. So the culture would definitely weave through from there.

Christopher Reichert: That's great. Yeah. Having that, that's where that culture of risk-taking I think is key. In so many stories, we hear about companies that are wildly successful, that it was that undercurrent.

Jossy Lee: Risk taking and then I always say, take calculated risk. And that's where our Sloan experience is coming in very nicely, because Sloan trained us well to collect all kinds of qualitative, quantitative data, synthesize information, and then inform decision making. I'm very grateful for what Sloan has taught me that helped me navigating through this process and then helped me to take smart risks.

Christopher Reichert: So it's been almost 10 years since you graduated from Sloan. And on reflection, what's the biggest takeaway that you think about from Sloan? Or themes, even themes that come up in your life as a result of Sloan?

Jossy Lee:  Human centered design is definitely one of that. Knowing there is such a process and then apply that to everything I do. Working life—collecting feedback from stakeholders and creating, testing, iterate—I think this whole entire thing was definitely what transformed my life.

People, I still kept in touch with a lot of my classmates and I still lean on them when I have things in working life, I need someone to talk about. My teammate at Sloan, Jeff Anderson, who is still in Boston, when I had something, I remember it was about a meeting, maybe, he just brought me up to his living room and then his wife, Christina made the best chocolate cookie in the world. I mean just that and then his kids playing around. I was like, totally be myself and maybe shed a few tears, but feel very open and comfortable to have authentic friendship from the Sloan community. I would say the entire Sloan experience has made me feel more humble and more confident.

Christopher Reichert: Interesting. It's an interesting combination.

Jossy Lee: Yeah. More humble because I know there are so many amazing people in the world doing wonderful things, I've seen that and totally admire that. More confident because I know where my spot is, where my strengths are, how can I best contribute to the team and who do I need to compliment within my team so that together we can all be the best we can be.

Christopher Reichert: That's excellent. With Woom, the book is the first initiative that you're putting out there. How about, what online presence are you thinking about? So I'm thinking of a community of members where they can check in and ask questions and get advice and that sort of thing.

Jossy Lee: Yeah. So that part is to be invented. To us we think that Woom has tremendous potential and currently we are thinking about it as three parts. So the first part is the product that we develop, the first book, and then will eventually become a book series and educational products related to it. And maybe designing welcome back from maternity leave gifts for corporations, so that one alone has a lot of potential in product development over there.

The second piece is more about insights and solutions. So for that one, so I'm from a new venture background, I have a team member who is also a Sloanie, Lori Newell, she has a background in consulting in Amazon for new products. So together we're pretty confident that we can go into the space and synthesize the information we need. So that incubating consulting piece, we are happy to take also clients in the space of supporting working mothers and help them find out what the strategy to move forward.

And the third one is what you mentioned, the community piece of that. We are still in the process of collecting feedback, a human centered design process to invent what that might be, but we are starting a Kickstarter campaign in September. So that will be a good starting point for us to iterate forward and to start to invite the community to join us as co-creators of the book series, as well as building the community together.

I have to say the Sloan community has been phenomenal in supporting us in this initiative. I found Lori, who currently is with me at Woom, through the Sloanie Helping Sloanies group. Then along the way when I had developed this book, I tested many times in the Sloanies Helping Sloanies group and our Sloanies were just amazing in giving their feedback and ideas and advices, so, I'm very grateful for that.

Christopher Reichert: So for our listeners, that's the Facebook group, Sloanies Helping Sloanies, a private, invite only for Sloan graduates, so.

Jossy Lee: Yeah. And it was started by Vimala and then Ingrid from class of 2011, two phenomenal women.

Christopher Reichert: Yeah. It is an amazingly vibrant group. I love, I check in all the time there.

So what's your definition of success, whether it's for yourself or the New England Innovation Academy or Woom or anything?

Jossy Lee: Well, that's such a good question. I think my definition of success is to share happiness with people, to uplifting and empowering people, because I believe the best way to keep happiness is to give it away.

Christopher Reichert: That's excellent. Do you have any advice for prospective Sloanies? Anyone listening who might think about applying?

Jossy Lee: Yeah, I do. Okay. For a prospective Sloanie, I will suggest you to be open-minded, in the process of exploring don't be fooled by a piece of information and be open-minded and to explore. I do feel there are things that you cannot tell from the website, so I strongly encourage to meet people from the schools that are you interested in. If you can visit the school, cafeterias, in the classroom and to see whether you can see yourself thrive there, to see whether you can see yourself being successful with those people, surrounded by you. And then I think exploring helps you find out what your passion is too. I mean, before Sloan, I used to think passion is this one thing, it's like one special unique shell that's on the beach and I'm here looking for that piece of shell and things.

My Sloan experience helped me understand, it's not really like that, it's more like you're not building a sand castle on the beach, so it takes hard work. It takes bringing information and sources, you are building things up instead of finding it. So I encourage you to go out and explore it and actually, you will have a better understanding about yourself and what is the right fit, what is the right foundation for you to be successful.

Christopher Reichert: Well, that's excellent. Thanks very much for my guest today Jossy Lee, a 2012 MIT Sloan MBA graduate, founder and creator of Woom, an incubator nurturing working moms. You can find them online at, as well as the Founding Member and Strategic Advisor at the New England Innovation Academy, which is opening this fall in the Boston area. So thanks very much again, Jossy.

Jossy Lee: Thank you. You're such a great interviewer.

Christopher Reichert: Thank you very much.

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