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From Product Manager to Entrepreneur in Residence - Discussion with Jiayi Liang, EIR @Amazon

Jiayi Liang, joined Amazon as a Product Manager in their Amazon Web Services business. After a few years, she joined their Entrepreneur in Residence program. In this episode, she shares her experience as an EIR (including what it was like to present to Jeff Bezos), and how she made the move from Product Manager to EIR.

Jiayi has a Bachelors in Economics from Beijing Foreign Studies University and MBA from The Wharton School, University of Pennsylvania.


Check out the podcast below to listen to the complete discussion.

Note from LED: If you upcoming Product Management interviews, don't forget to check out our Interview guide for PM interviews in Tech, our Question bank for behavioral questions, and our Question bank for Product Design questions​, to help you prep for your interviews!


Some of the areas that Jiayi touches upon in this episode include:

1. How she got into Product Management with zero technical background
2. How Jiayi focused on earning her team's trust from the get-go
3. How Jiayi developed proposals for ideas she had and circulated them within the company for two years, which helped her get in front of the right people
4. How Jiayi got into the Entrepreneur in Residence program at Amazon
5. Jiayi's meeting with Jeff Bezos to get seed funding for her idea
6. What happens in the Entrepreneur in Residence program
7. 3 qualities that enabled Jiayi to get into this program - openness to learning, resilience, and patience
8. How she really invested in learning about the business - which helped her build her network and earn trust
9. Setbacks that she had along this journey
10. Courses that Jiayi used to teach herself basics of computer science
11. Career advice

Thank you for listening!! 

Here's the transcript of the detailed discussion:

[LED]  00:03

Let’s start with a quick snapshot of your career path so far. What got you interested in tech? You didn’t have any previous Tech experience right?


[Jiayi]  02:23

Totally. So I sort of stumbled upon Technology, I had an Economics degree in undergrad. And when I first graduated, I figured, well I haven't exactly figured out what I want to do with my career. So I decided probably the best way to start is to join management consulting, so that I can explore a variety of industries. So I started my career at Kearney, and then wandered among industries such as consumer products, energy, etc. And really found a lot of my interest was into renewable energy products. 


But energy industry moves very slowly. Post MBA, I figured, how about trying a new type of technology that moves a lot quicker, which as you know tends to be internet and web-related services. So I transitioned from hard tech to soft tech, and I joined Amazon Web Services right out of business school. And that started my whole journey into internet and technology and fast paced innovation.


[LED]  04:09

You joined a very hardcore tech product, and from what you've just told me, you don't have a lot of technical experience, at least prior to AWS. Was that a challenge in any way?


[Jiayi]  04:39

You're right. So actually, there are two things  - A) Why did I choose hardcore tech and B) How hard was it in the beginning. 


I had a very simple thought, which is how can I maximize my learning and growth potential so when it came down to choosing my first job after business school. I simply wanted the job that can stretch me the furthest. If I fail, I fail fast so that I can learn. So when I was looking at all the jobs in Amazon - I knew that I've done customer products, I knew I've done ops. But hey, web services, technology, that's the hardest and the furthest away from what I can do. So let's start from there. So I intentionally ended up in an environment where I'm the least comfortable, but I also know that I intentionally go for the least comfortable so I can learn and grow. 


But then to your question, how was it like to be in the tech role in the tech world when you know, I didn't have a computer science degree. It is definitely hard because what product manager does is to drive the roadmap and to understand the customer pain points, and to derive not only the solutions, but also the prioritized set of features. To do that, it is really important to understand customers pain points, to really understand the technical details. So the lack of tech background, in the beginning, it was hard for me to even understand what my customers mean, what they're talking about. But that being said, not having a degree or something doesn't mean we cannot grow strong in the domain. So for me, the first thing I remember when I first received the offer in December, is that I knew I'm going for something very hardcore. So then I started learning, picking up all the cloud, cloud-related courses, going through Coursera, and doing my CS one. 


And then by the time I got to Seattle, in the summer in August,I started to ramp up with my team. And then literally sitting down with all my engineering peers and quickly find mentors and identify, Hey, what are the most important things I need to know? So that I can understand my customer. And here's what I already know, right? It's not like I haven't done my homework, but help me grow in the direction I need. 


So one example was the first product I was building and launching was Amazon trusted advisor. It is a cloud optimization platform to help customers do better with their resources on AWS to improve their reliability, reduce cost, and improve security, etc. And my learning path was  quickly identifying the areas that I'm very knowledgeable and strong in, which is cost optimization. I start from there. And from there I quickly got interest from both my customers and my engineering team. In essence, for cost optimization, our goal is to identify the underutilized instances, and turn these off for customers so that customers can save. So that's sort of my entry point, to start launching additional features. Through that, I built, trust, and earn credibility with my team. And that also leads give me confidence to continue to learn more about other aspects of the Amazon Web Services core services


[LED]  08:52

This is such an impressive attitude to have! Jay. What stands out for me is how you did your homework and found a way to quickly build trust with your team.


Was lack of a technical background a challenge when you were recruiting?


[Jiayi]  09:45

At my time, the way Amazon did MBA recruiting allowed everyone an even playing field. Everyone is recruiting for a product management role, across all areas of Amazon. The specific placement happens after the offer is granted. And the candidates can continue to network and identify the team they want to be in. Now that has changed, because Amazon also realized that there is a specific requirement on technology. So later on the product management hiring evolved into product management, like the classic PM, many focus on business, customer experience. And they added a new category called product management technical. So actually, from my year on, and later, candidates must have a CS degree, or previous Tech experience to even apply and qualify for PMT. So on that note, I am extremely lucky.


[LED]  11:06

Nice! So yeah, tell us, what does an Entrepreneur in Residence do?


[Jiayi]  11:33

Yep. So an Entrepreneur in Residence at Amazon is someone that is tasked to identify and build a business. And this is a very typical title, you can find such programs in many larger companies, and also a lot of venture capitals, run their EIR programs.


[LED]  12:00

Is this sort of just another job that you can apply to? Or is it a program where you have to go in with a business proposal? How does it work?


[Jiayi]  12:26

So I want to touch upon two pieces  1. what is this program? And Amazon? What’s the background? And then 2. How, how did I land in this role? 


So the first part is, for any large companies, the only way for them to remain relevant is to continue to invest in innovation and new products. One example is if you look at Forbes, the top 100 companies change every 20 to 40 years, and only 4% left. So the only way any business remains relevant is innovation. In Amazon, there are two modalities of innovation, type one innovation are those improvement, incremental improvement based on what our customers tell us saying based on the existing business. And then there are the other types of innovation that are more radical in nature. It requires more resources and higher appetite for risk, say investment between three to five years looking into blank space domains where the company is currently not working.This program is one of several programs that focuses on the Type Two innovation.


[LED]  14:18

And how do you get into this program?


[Jiayi]  14:41

And so, first of all, this organization is extremely secretive, they do not talk about it. So the way I stumbled upon it was, I first spent two and a half years building and launching cloud based enterprise focused applications in AWS. And I've earned a reputation of a builder. And then after launching two products, I started to realize I really enjoyed this builder part of me. And I am not satisfied by the incremental improvement I am doing. So one example - this is almost two, three years ago, when Alexa got introduced. I started already to draft some business proposals to my VP saying, here are some of the concepts I have. My VP said, great idea. But these probably will take a longer period of time, more investment, so we can ignore it right now. So these are a signal that I am on the right track, I'm thinking the right thing, but probably I need a different avenue. That didn't deter me. I started to use evenings or weekends doing site projects. Nothing stops a creative mind. Nothing stops someone who is a product thinker and thinking about product innovation. So I started to build proposals, two of which began circulating across the company, finding different VPs across different orgs. And these got traction. And I’m glad to say that of those two projects, one is Amazon photo printing, which was launched last July.


And then the other one was the Smart Lock feature, so that we reduce the lost packages for our customers. So I pitched these two concepts to individual teams. Great response. Unfortunately, these teams back then didn't have headcount. So I didn't get to join and do work on the projects. But I was really excited that after two years, I can finally talk about these ideas. The whole exercise took me about a year to continue to build and socialize some of the concepts I had, while I was doing my day job, AWS, working on the Amazon WorkSpaces product. 


And then it happened that in one of the presentations I did, someone from the EIR program was there. So they reached out to me afterwards and said, Hey, Jiayi, we're really interested in your experience, can you come and give us a talk. Yeah, of course, happy to. So I went to this group, I did a presentation about my concept I had been working on. And then the leader of the group reached out saying, hey, Jiayi, we're really interested in your experience. Here's an opportunity - you can join us, spend a year working on pretty much a blank space. Our goal is to identify and pitch new businesses to Amazon that has the potential building into the billions. Are you interested in joining us?


LED  18:59

This is awesome! I have so many questions, but complete your story.


Jiayi  19:04

Oh, yeah. So he said, Do you want to join us? So back then I had already actually gone through some of the accelerator programs outside of Amazon for this concept, but then when I heard about the autonomy we were given and the amount of support we will have to lead a billion scale business - I'm like, I'm saying yes. I took the weekend really going through and all the factors and then come back the Monday. I told him yes, I'm in. Bring it on.


[LED]  19:47

I think the most impressive thing is that one, you didn't let anything stop you from continuing to work on your ideas. And then you found people in the company to go and pitch to and you somehow convinced them to give half an hour of their time so that you could present your ideas to them. 


[Jiayi]  20:35

You're giving me a lot of credit!. Amazing, though, I would echo your comment that the culture of Amazon defines the tone. Amazon is doing a great job in fostering this concept of customer centricity, meaning everyone is encouraged to think about what we can do for our customers. And then because of that, we have the data we can use that to communicate. And therefore there's a culture of listening. There's a culture of being open to new ideas. 


[LED] Can you apply for the program? Or is it always that they have to somehow hear about you from somewhere?


[Jiayi]  22:26

Yeah. So from the sourcing perspective, our program and Amazon, it runs more on a reach out perspective. So the group will constantly send out feelers for individuals, that is a great culture fit, again, entertaining that constant and innovative mind, who really thrive to delight our customers, and have the ability to build. 


We also fill our pipeline through referrals, meaning people know people who are like minded. And also, we have established this very scalable platform within Amazon called Think big competition. And it is a competition open to everyone at Amazon, who can submit their business proposals. And then those who proceed to the last round get to pitch at Esteem which is Jeff and his direct reports. So I would say people drive themselves towards this program. And also internal referrals.


Jiayi  24:59

So we start with, say 12 months exploration period, and this time is fairly similar to the other EIR programs. During this time, individual is tasked to identify an area or domain of our interest. And also, of course, we constantly receive feedback from senior leaders. And then, throughout our process, we use the model of Amazon. So we write one pagers in documents, to quickly capture our idea and concepts for those who gain traction, we start to put more data and prototypes behind that. And the exit round is a pitch to get to receive funding, we call that the seed round. And that is a turning point from the ideation phase into the operation phase.


[LED]  27:21

So how long did you spend working on your proposal - a year? And throughout time, are you working alone?


Jiayi  28:49

Correct. So I was a solo founder. At the same time, I have a pretty robust support network, meaning I was able to hire a part-time and contract team to support me. But I would say in the most ideal case, it would be terrific that I could have co-founders, like a small team between one to between two to four people, I would say that's a perfect size. 


Solo foundership is really, really tough. So in my next venture or for anyone that is interested in the startup world, find a co-founder that is going to make life easier, and make the journey a lot more fun.


[LED]  29:48

So tell us about the Jeff Bezos meeting. How was it?


Jiayi  29:53

So the meeting was great. You know, after a year, spending a year and a half doing it - I had butterflies in my tummy!

His laughter is really contagious, when he laughs, you can feel the tremor across the table. It was quite nerve wracking, preparing for that conversation. The benefit of this program is I can get funded by the world's largest VC. But the downside of this program was pretty risky. I only have one option, yay or nay. 


The Amazon pitch session is not a presentation. The Amazon pitch session is run by documents. So everyone comes in, sit down, read our pitch document, which is a six pager narrative seriously. And appendices, etc, etc. So we have an hour session, and then the first 15 minutes everyone sat down and read. So that was actually kind of, you know, looking around saying, how's everyone doing? Which page is everyone on? What note are they making, etc. So the first 15 minutes, I was like, hold my breath countdown. But then when everyone looked up, I was saying, Oh, my God. He was sitting right across me. The first thing he said was , you have a winner. Oh, wow. Yeah, I'm like, I wasn't expecting that. Right. I thought about all possible solutions. He could like fine, go do it. I'll give you like, 25% of what you're asked for. 


LED  33:07

Wow I'm sure this must have felt like a huge personal win for you, right? I mean, you just created the proposal for something which convinced someone like Jeff that it's amazing.


Jiayi  33:31

Thank you for that, I think, I will say I celebrated, I celebrate but at the same time is really something larger than just me myself. Because what excites people is the fact that we're working for a cause meaning something bigger, something, not just saying I want to be the first one doing something is actually the impact of developing this product or this cause. 


When we identify a great opportunity, let's have conviction, let's go all in. Let’s focus on building. Our approach is clear. And our outcome is clear. Let's go figure it out. Let's get the right people. Let's have the right resources. But let's go figure it out.


LED  35:32

Yeah. So now that you have your seed funding from Jeff and his team, are you the CEO of this startup inside Amazon? 


Jiayi  35:51

My official title is initiative lead in my organization. I'm the founder and the CEO, though in our internal tool, we actually don't have the CXO title. We thought it's kind of snobbish to use that title. So in essence, I'm the founder, and I'm the leader for this group. And with our initial funding, I was able to build up the team. And now we're at a team size of 14, going through this very quick concept, iteration phase, and then doing our early, early stage working prototype as a proof of concept. 


LED  36:40

In terms of your role, you are sort of playing the role of a typical founder? Do you have to hire your own marketing person or are you sharing Amazon's resources?


Jiayi  37:05

Yeah, great question. So for my initiative, I'm responsible to hire my team, the core team, the core team being my function, our engineering team, our design team and product team. So one benefit of being an internal initiative inside of a larger company is we get to use the shared service, such as finance, legal, and we receive recruiting help, as well. So that's really helpful. 


LED  38:11

And then do you have a manager? 


Jiayi  38:22

it's a great question. I do I do. So when it comes down to org structure, and my initiative, my own startup rolls up to the head of our incubation program. So this is a VP at our company. And then recently, we just had a reorg, where approved or funded initiatives will roll to a different leader who oversees all the operations, which actually makes a lot of sense. And then this operation leader rolls up to the VP, the head of the incubator. 


LED  39:11

Is your own performance linked to how your startup does?


Jiayi  39:40

Success is measured - a) whether we deliver on our product plan. Our goal is we want to build this amazing product and also deliver customer delight. So that's the first part. b) The second part is, I'm also assessed on how effective of a leader I am, as a leader of our initiative, guide the team through a period of ambiguity, build the team and develop them.


LED  40:15

I'm curious about what are the two possible outcomes, if we take what you're doing. So one outcome is you’re super successful and that's awesome. But let's say it didn't work out. Can you go back to your full time job at Amazon, or is that a challenge? How do you do that?


Jiayi  41:23

Yep, totally. So on the first note, what happens when the product is truly successful. So for our incubation program, it's been around for three years. So the first product project being funded, is about to ship. So it hasn't been launched yet. So therefore, on that note, I do not have to tell you what will happen to that. However, other organizations who are doing the title innovation, I can give you several examples. For example, Amazon Go, Amazon call the entire organization was this innovation focused org, they were super secretive until they were launched. They became their own standard business operation, rolling up to a SVP. So that's one the model of success, where I can similarly hypothesize or conclude that programs or initiatives, going through our incubation program, when successful can have a path of becoming their own business unit rolling to a different organization being merged to another business that is relevant, or company to be continued to operate in our world. So I think any three of that scenario could be possible. 

And then on the second note, what happens when things go south? One scenario is that they need different types of leaders or different types of competencies. A new CEO is brought on board. So that could be one scenario. In those case, happily to take on whatever role I fit in that organization. The second scenario is this concept entirely flopped. It's already failed. Well, in the course of building the business, there's always a chance that the business flops. And if that's the case, find another gig. Learn from it. Find another gig, not to worry about it.


LED  44:26

Yeah, and I guess that's the right attitude to have. What are 3-5 skills or qualities that really enabled you to get into this position?


Jiayi  44:53

I would say first of all, I'm a lifelong learner and resilient and patient. These are the three things come out at the top of the mind. 


The first one lifelong learner - there are always areas that we can improve on. And being strategic about what to learn and what to grow into will help us stay focused, and reform my journey of growing. I started by first picking up on the core part of cloud computing. And use that as a key to open a new world of innovation. Had I not done that, that learning, I would have not been today where I am. 


And the second part is about resilience. Resilience means ability, have to have the ability to endure the pain and setbacks in the process of growing. My measure of when I know learning and growing is how uncomfortable I am. Because I know when I'm uncomfortable, I'm learning something new. And at the same time, learning something new is painful, because that shows that we are in some area not good enough. Therefore having a very resilient response system will help us stay focused, stay motivated, instead of just saying, I'm giving up. 


And the last part is to be patient. In this day and age, a lot of venture money comes along, everyone wants to be rich fast. But sometimes that might not be the best way to arrive at a real goal. And what really helped me getting there is I knew where I wanted to get to, you know, back then in 2014 2015, when I started to pitch ideas I knew I want to build, and I know that I want to be the founder. And therefore I started by doing very basic, basic basic coding problems, right, repeat Latin translator, I wrote a small module for computer vision, control the camera unit, I started from very basic exercises, and then work my way up through larger, more complicated problems. And then when I went to socialize my concepts, I started with my peers who might know, and then ask them for referrals and talk to managers, directors and VPs. And that whole process took a year, a year and a half. Had I not had that patience to go through the whole process. I would have not had the humility or the amount of organizational awareness to get to where I am.


LED  48:09

One thing which really piqued my interest there is that you mentioned that how you used this step up approach - once you'd build your proposals and ideas, you initially reached out to people that you knew, but then you’d ask them for referrals. Do you think that helped you reach a big portion of the org?


Jiayi  48:46

The reality is that it comes down to knowing the business really well. I know the business really well. And that earns trust. And the way to do that is going back to say this one example - Amazon photo printing. I started as a side project when I realized it is a quite a pain for myself as a customer to identify photo printing options and have to either go to Walgreens, or go pick up versus every week, almost every week, I receive an Amazon box. Wouldn't it make sense for me to receive my photo prints in my Amazon box? It started as simple as that concept. 


At the same time, I also know that ideas are cheap. Ideas are cheap, but building a very solid business plan takes a lot more effort. So I knew that maybe I'm not the only person who has thought about this, but I want to at least leverage what people have discussed. And also add in my perspective. So part of the reason I did a round of conversation with people in, camera category or Amazon photos, is to understand again, going back to the humility part is what has been done. Here's my proposal. What else should I consider to make this more polished? That's what really got the conversation started. I remember for that project, I was on total printing, I talked to at least probably 30 individuals across the retail category, logistics, shipping, fulfillment, etc. It helped me build a very solid proposal, I captured why, in the previous two years, similar concepts had been pitched but didn't get funded. 


LED  53:29

Do you have equity in this initiative?


Jiayi  54:33

So great question. The way this program is structured, I do not take equity. There are other programs or other companies out there, for example, Google has a lab 123 and there’s equity discussion over there.


LED  54:50

Say someone outside Amazon hears this discussion. Is there an option for them to apply to this program?


Jiayi  55:21

I think it's going to be pretty hard to find it online. For for the reason I mentioned, meaning a lot of time the team does internal sourcing or we find referrals. 


Though I would ask these candidates to ask themselves, why are we interested in entrepreneur in residence program? What does it get us by joining an ER in a large company versus joining EIR in a venture backed company versus going through our own accelerator program or incubator program to do something? I think probably that's one question that’s important to answer. In my case, the reason I went with the internal incubator option is I was drawn by the scale and level of support.


So the two reasons that I chose to join the internal incubator is first scale and support. The second part is, this is my first time, my first time launching a commercial product. So by being in an environment where this happened all the time, I believed that will add to my chance for success. And as it turned out, a year and a half later, I am getting what I wished for. So these are my two rationale to try for the internal program. But to your point, let's think through why we want to do it. And going back to the framework of what is my goal? What is my approach? And what is our outcome? And decide which is the most appropriate path.


[LED]  1:00:09

Any parting advice you'd like to share with our listeners?


[Jiayi]  1:01:03

I would say, going back to being tenacious, being resilient - resilience is a habit. Let's get in that habit. And that's one thing that really can get us far. And then I would add, to note for what helps me to remain sane, and, quote, unquote, successful in what I'm doing. The first one is good health. So I will say the time when we learn coding, when we learn new things, let's also workout :) let's workout for 30 minutes a day. And one thing I noticed from Jeff in the meeting is he is really fit. All these great leaders are also really fit because they know investing in our health gives more,returns later. And then the second part is - remain grateful. Things can be hard at times, not everything goes according to our needs. But being grateful will ground us. And that will make us be more appreciative about the situation. And when the opportunity comes, I think we'll be ready. More ready, actually.


If you have any questions for Jaiyi or for us, you can email us at or tweet at us @led_curator or like us on Facebook at

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