How to Learn Product: Going from Product Manager to Founder with Erin Chan

Episode Transcription

Erin Chan:

It's the role of the PM to identify the most impactful, most important things for the team to work on and zero in on the most impactful things that the team could be working on to help move your area forward.

Christian Beck:

In this episode, we have our first ever Olympian, but before I tell you about that, let me tell you about her. Erin Chan was formerly Senior Product Manager at Shopify, and now is co founder and CPO at Rhenti, a real estate platform on a mission to make renting easier, faster and more transparent. Prior to getting into product, Erin was an Olympic synchronized swimmer. And because I was curious and I had to ask, we are going to share a quick snippet of Anna and I talking with Erin about her athletic career. Here's me asking how she got into synchronized swimming.

Erin Chan:

So both my sister and I, when we were young, we were pretty active kids. And the only way that we would sleep at night is if we were very active during the day. So she was constantly trying new sports and activities to get us tired. And she just came across synchronized swimmers one day, they were just swimming in the pool and she's like, "That is a beautiful sport. And I'm going to put my creative child Erin in this." And so I tried it and I happened to be pretty decent at it. And then it just went from there.

Christian Beck:

That's cool.

Anna Eaglin:

That's awesome. What do you think makes someone great as synchronized swimming?

Erin Chan:

So the first thing is the child or the person just needs to be creative. You have to swim to music and often you have to collaborate with your teammates and the coaches on choreography. So just being interested in coming up with creative movement is one thing. The second thing is you have to have a great feel for the water, that always helps. Although you can train through the kids who are a little bit more awkward in water. The third thing is flexibility. If you've ever watched synchronized swimming, extremely flexible moves, really bizarre, twisting weird moves. And if you're flexible, that definitely will take you a long way in the sport.

Christian Beck:

As you can probably tell, we went off on a bit of a tangent with her, but how rare is it to meet an athlete of that caliber? It's pretty rare. I think she's the first one. And if they gave out metals in leading product, I think Erin would also get the gold. As everybody cringes at that, I am a dad. So I'm allowed dad jokes now and then. But getting to product, you know what the show's all about. One of the many reasons we reached out to Erin is because of an article she wrote on Medium, which we'll link to in the show notes. In the piece, she shared her experience working on her first big project and specifically highlighted some of the challenges around complex software. So I asked what was it that got her to Shopify and what was she hoping to learn?

Erin Chan:

I knew that it was my time to start looking for my next opportunity. I applied to Shopify and with amazing luck, I got the job after many interviews, I have to say it was 11 or 12 interviews. And what I was looking for and what inspired me is just an incredible learning experience where I could grow, where I could expand my skills and just experience another industry in another company.

Christian Beck:

As we've discussed many times in this series, there really is no degree for product management and the paths people take to become product managers are always unique. Erin is no different. To launch us further into the conversation, Erin shares her own path to product management.

Erin Chan:

So I'm going to take this back. And I was at one of Canada's big banks. So one of Canada's top five banks, and there I was what you call a digital strategy manager. And I recognize that, again, the impetus for change is unhappiness. And so I recognize in that role, I was there for a year, year and a half, I was pretty unhappy and unsatisfied because I recognized that in this role I wasn't using any of my strengths, none of them. And there came a point where I just was like, "You know what? This isn't working. It's time to move on." And so I started researching other roles and I came across this role and I have to say that was back in 2014, I had never heard of product management, but here I was looking at this job description for a product manager.

And again, the title meant nothing to me, but I kept reading on into the job description and it was amazing. So I came across two things that really stood out to me. It was working very closely with people and collaborating. And that stood out to me because I come from a team sports background and I'm all about collaborating and achieving something by working with people. So that was one thing that really stood out to me. The second one was building something for someone, but getting really close to the people that you're building for and really understanding them. I'm like, that is amazing because I have my undergrad in design and what you do is you build for other people and you have to understand who those people are in order to build from them. And in grad school, I specialized in business design, same thing.

You get really close to the end user to build something for them. So it was like a dream come true. It was like a magical moment for me. I was like, this is the most perfect job for me. And I submitted my resume and I have to preface this with one thing. I did have a connection into the company who was able to get my resume in front of the hiring manager. Because without that, it would have been very hard for me. And one thing led to another, after a series of eight or nine interviews of interviewing everyone that I'd be working with, I got the job. And that was my foray into this awesome, awesome discipline of product management.

Christian Beck:

What do you think you were ready for through education or just maybe your own personal strengths, in what areas do you think that maybe surprised you that you had to actually learn on the job?

Erin Chan:

What I was ready for was the collaboration aspect and the leadership aspect. So getting a team and a group of people motivated to take on a mission or a big project, that I loved. It's perfect for me. The other thing that I was really ready for was getting close to that end user. The people that use the thing. That kind of work is just incredible. When you talk to these people and when you understand their lives or try to understand their lives around a problem space, that gets me incredibly excited. So I thrive off of those two things. One of the things that was most difficult for me was the stakeholder management. So when you do product management in a medium, I would say even large sized company, part of the job, it is literally part of the job, is you have to manage the expectations and the opinions and the point of views of many, many people. And that is hard to do. And the bigger the company, the more people come into play and it gets harder. And that's one of the areas where I had a lot of growing to do.

Christian Beck:

You started your PM career extensively at Koodo, but it sounds like Shopify was your first job where you knew product management and now you're setting out to do it somewhere else. So what changed this time around when you started there?

Erin Chan:

What was different when I jumped from Koodo to Shopify was I learned product management at Koodo, and I learned the theory of product management, and I had the great opportunity to carry out that theory. And usually the reality is very different from theory. I must say, first of all, and then going to Shopify, which in terms of product management discipline, much more mature organization. I had to essentially level up my discipline. I would say the most prominent area of growth for me, like I mentioned before, was stakeholder management, but also prioritization, extreme prioritization. And at a large company that is so incredibly ambitious. There are so many things that you can do to help push that flywheel, help push that company forward. But at the end of the day, it's the role of the PM to identify the most impactful, most important things for the team to work on and zero in on the most impactful things that the team could be working on to help move your area forward. And that's where I had the most growth.

Christian Beck:

I want to stop on something you said really quick. You said the theory of product management you learned, and then it almost seemed like you were contracting with Shopify being much more mature? Can you tell us a little bit about what you mean by the theory of PM or how organizations might just have the theory of PM, but not the practice?

Erin Chan:

Yeah. And actually, I want to pinpoint this down to Agile specifically. So I learned the theory of Agile at Koodo, and the whole idea is the entire team is working at this table and you're working incredibly nimbly to move things forward. And there's a bit of a structure to it. There are sprints, there are all these ceremonies that you do. But when I come to Shopify, it was bizarre in the way that Agile wasn't a huge thing. And the company was so big, one of the things was they let every team and product manager operate in their own way, at the time. And so I came in to find that no one was really using Agile, they were doing their own thing. And they were doing things in ways that worked best for them.

And so some of them were choosing to not use Agile and just do what suited them. And so it was like this mishmash of processes. I'm not saying that's the way Shopify operates today, because it has grown quite a bit in the past few years, both in terms of size, as well as in terms of PM discipline. But at the time there weren't really many playbooks. And so I found that really interesting, and I found it actually quite mature to give your PMs and your product teams, the space and the agency to do what they see fit. And that comes with maturity and trusting the people that you bring into the organization and trusting that they will find the right process for them. Because not every team in Shopify is the same. They're working on different problems and their team sizes are very different. Their dependencies are very different.

Anna Eaglin:

You've mentioned a lot of important skills or skills that you found that have really helped you become a better product manager, things that you've had to work on. What do you think are those crucial skills for a product manager?

Erin Chan:

There are a bunch of them. But I want to pinpoint just a few of them. The first one, you just have to be really good at working with people and collaborating with people. Because at the end of the day, you are trying to achieve a goal or an experience and in order to achieve that, you have to get everybody in the game. And the better that you work together, the better the product is going to be. And I think it's really important to keep in mind that as the PM, I'm not the one building the thing. You have a team of devs or engineers, and you have designers, you have data people, marketing people, and those are the people that are truly building the thing to solve the problem that you, as a PM, have identified. So collaboration is key.

The second skill, and I'm not sure if this is a skill, but traditionally for a lot of people, they will have experienced companies where you are expected to know everything and you are expected to almost be perfect at your job. The best PMs are really good at embracing humility and curiosity. And so that means I'm bundling the behaviors that you had before, which is when I'm asked a question in a meeting, I have to have a really good answer, and I have to answer it perfectly and with authority. But I would argue that the best PMs are really good at asking questions and asking the right questions to surface the right insight or the right answers. And not only should it be the PM's that ask the questions, the PM should foster an environment, a team environment, where everybody is comfortable saying, "I don't know the answer to that question. We should go and find it out together."

And the thing with tech is the landscape changes so quickly, whether it be your competitors, the company itself, or user behaviors change, can change on a dime. And even if you had say 90% of the information at one time, the landscape will change and then you, as the PM, have to go back and start asking questions again. And just embracing humility, embracing curiosity, and having that growth mindset is really important for PMs. The last skill is storytelling. It's after you've identified a problem space, being able to tell the story in a very compelling manner to get everybody onboard. And not just onboard, but really excited about the problem space and the mission and the path that you're about to go down.

Christian Beck:

And so catching up more to present day, you left Shopify to found your own company. I'd like to even just pause on that transition, because I would say over the last several years, I've been observing more product managers going and starting their own companies. And so I'm curious, from your perspective, what is it about that that makes product managers good founders?

Erin Chan:

One of the things that make product managers really good founders is identifying the problem space and knowing how to be close to the people that potentially use the product. Those two behaviors and skills really lend well for product managers growing really successful companies.

Christian Beck:

To be clear. So Rhenti is finding rental homes. This is very different from any industry you'd worked in there. So how did you get that firsthand knowledge?

Erin Chan:

I've been a renter for almost half my life. And my husband has been a long time renter as well. And we identified that renting as a renter is a really crappy experience. It is full of opaqueness and really the power is in the hands of property owners. So we were really passionate about the problem space, essentially boiled down to we experienced a problem in our lives, and we are very passionate about solving that problem for us and for other people.

Anna Eaglin:

As you made that transition from senior product manager to founder. What did you expect being a founder would be like? And then what was it actually like?

Erin Chan:

Being a founder close to matched my expectations of what a founder is and does. It's pretty intense. If you think that product management is intense, being a founder is actually more intense than that. Because not only are you trying to build this great experience and this great product that creates value, you're also thinking about this product needs to make money, this company needs to generate revenues and profits eventually. Inspiring a team who has taken a big chance on joining your team as a tiny startup. How do you keep these people inspired and motivated to do their work? So there's all this complexity layered on top of the role of product management that founders do take on, and it is incredibly stressful.

Christian Beck:

What skills do you think that you had that have served you well so far in the highly stressful role as a founder?

Erin Chan:

The most important skill that has served me well from going as a PM to a founder product person is prioritization. There is so much opportunity and possibility, but when you only have so much funding and you have a very small team, you have to pick and choose what you tackle. That's where the skill of extreme prioritization comes into play. Especially when it comes to building the product. We have this environment where I try to insent the team to provide their point of views, give their ideas. But at the end of the day, I have to ask them what problem are we trying to solve? And is it the most important problem that we can solve right now? And sometimes it's no. And sometimes it's yes. So prioritization is key.

And also being a founder, prioritization is key because now I'm PM. I'm also leading marketing. I also do people work, traditionally called HR, I take on some of that. And also fundraising. So when you have your hand in so many disciplines, it's like, what can I do today, or this week, that is the most highest impact thing that I can do to help the team move forward? And again, it comes down to prioritization. I always have to remind myself the most important thing or the most impactful thing, most of the time, that I can do is drill down on getting the product right, and getting the team to work on the right things. That's usually the answer that I will fall back on.

Christian Beck:

I'm wondering if there's a transition from say, leading product for a product company that that's not yours necessarily, to now having to do it for something that's yours, where you're also overseeing a little bit of the business and this is yours and it was also born out of your own personal experience? Have you found it challenging to maybe separate the professional side of what you need to do as a product manager and then the maybe personal side on what you want to see with the product?

Erin Chan:

It is. It's challenging to separate. Because I live in breathe our company and the product and the experience that we're trying to build. It doesn't end. 9:00 to 5:00 does not exist here. I would love to say, I know there's this stigma against the word hustle these days, but I have to say, we hustle. We are really trying to build this company as fast as we can. We're trying to push our creative limits on finding ways to grow it. But my professional life is now my personal life. And I hate to say it. I hate to say it, but it's true. So it's hard to separate it now. One day, maybe next year, maybe the following year, when we have a bigger team, we will be able to separate it a little bit better, but right now we just don't have the team to have that freedom to have many off hours.

Christian Beck:

Hustle is the safe word on this podcast.

Erin Chan:

Okay, great.

Christian Beck:

So you're okay saying that.

Erin Chan:

Okay.

Christian Beck:

I was one of the co founders of our agency as well. I am very well aware of it. It is become a bad word, but it's like when you glorify the hustle for hustle sake, that's different than hustling to get your product to come to life and doing the things that you need. Because you're right, there's so many things you have to balance. Some mornings you wake up and you just feel like you're hours away from everything falling apart and you just have to do things to keep it alive. But I wonder too, as you scale the team, maybe it's too early to tell, but do you maybe hope one day that you bring someone in that leads product and you move out of that or do you feel like even as a founder and leader of Rhenti that, that's still something that you want to be a part of?

Erin Chan:

I think I will always want to be a part of it.

Christian Beck:

As you're leading product in Rhenti, and you're doing this it's emerging alongside you. What's something that surprised you so far from what the vision was maybe three or four years ago versus today?

Erin Chan:

So when we started out, when this was a seed of an idea, because we felt it in our own lives. So we felt that this perhaps was an overriding problem. That the rental, leasing process was really crappy. We started interviewing renters and we started interviewing property owners. We did a nice big survey and we got insights from that back. And then we started going down a path of what a solution could be. And I think one of the most disappointing things for me was the solution that we had come up with wasn't the right one. So when we went back to these property owners and we're like, "Okay, this is what we're thinking." And they just weren't comfortable with what we were building.

So in a sense, I think we were a little bit too innovative and trying to move too fast and people weren't ready for that change. And so the surprising thing was, was like, "Okay, we need to take a few steps back and pair this solution and this vision down to something that is actually tangible for people." And I think that was one of the most surprising things for me is people wanted something different, but they weren't willing to accept it.

Christian Beck:

How did you figure that out? What were the signals? What was telling you that they're not comfortable with us?

Erin Chan:

They flat out were willing to try the solution. They're like, "I'm not comfortable with this thing." And there was one thing in particular that very much stood out and they're like, "I am not comfortable with that. And so I can't try your solution because your solution is predicated around that thing." So it was very easy to see that this wasn't going to work. And so we had to go back a little bit, take a few steps back, go back to the drawing board and make some tweaks. So it was just the buy in from prospects, it wasn't happening.

Christian Beck:

Are you still getting feedback today, fast forwarding to now, or have some of your user feedback mechanisms changed?

Erin Chan:

We get a lot of feedback now. So the Enterprise Property owners that we work with, we work with very closely. So whether that be me chatting with them, it's mostly our CEO. So Thomas, as well as Justin, who is our head of revenue, all three of us loop in with these people and understand how A, how the current solution is working for them. And B what are the other needs that are not being met? What are those? And so through those conversations, we're able to understand how do we better reiterate on what are exists. And also it determines what our roadmap looks like or part of our roadmap. So those conversations are incredibly valuable. And just one of the big parts of product management is constantly talking to users, or the people, I hate to call them users. The people that use the thing that you've built or your solution.

Anna Eaglin:

So one thing that we hear a lot from founders is they don't know how to deal with customer feedback or user feedback, because you don't want to feel like you're waving in the wind to how your feedback comes in. But you want to be really receptive what people are telling you. How do you figure out what that stake in the ground is? And then how do you make changes?

Erin Chan:

It depends on who the feedback is coming from. So if the feedback is coming from a particular, say, Enterprise Property manager or owner that is really in the target market that we are trying to build for, because there are many types of property owners, but we are trying to build for a certain slice. And we are trying to be really great for that slice of the target market. And if the feedback is coming from them, we take it very seriously.

And if there are numerous of those users that are giving the same feedback, we're like, "Okay, we are going to take this very seriously." If it's just one, then it's like you put it on the radar, put it in the backlog, and until it becomes either a larger problem for this user, or if numerous, many of them, are talking about that particular issue, then we start raising it to become a priority. And also we need to assess the impact. What is the level of impact? Is it just the design of a few buttons or a form? Okay. Maybe the impact is medium. Maybe it's high. We need to assess that. So it's how many people are requesting it or complaining about it? And what is the impact of that thing that they're requesting or complaining about?

Christian Beck:

What are you looking forward to in the next six months with Rhenti?

Erin Chan:

The next six months are really exciting for me. Because if we achieve what we set out to achieve, we, in theory, will have developed a product and a solution that will be incredibly valuable to our slice of the target market, which is Enterprise Property owners of a certain size. And so I'm really excited for when we build those things and when we push them out and release them, I'm really excited to see what the traction is like. Because from our research and from our conversations, the traction should be good. And if we stay close with those property owners and we build it the right way, and when we build it alongside them, all signs indicate that we should be in a very good place by the end of the year.

Christian Beck:

You think about where you want to be, what does that look like to you? Is it numerical? Is it is a quantifiable? Is it maybe milestone oriented? Is it getting these features out there or adoption? How do you at least categorize so that you could look back at the year and be like "We did what we wanted to do."

Erin Chan:

It's always such a great accomplishment for the build team to release. And release big milestones. So yes, from a product perspective, it's nice to get that work packaged up and out there. But also from a product perspective, it's a numbers thing. So in theory, if you build the thing right, it should develop traction. And so what I'm really excited for is seeing that traction and it is a numbers thing. It's like for us, we quantify our business on how many rental units are using our platform. So that's how we quantify Rhenti and our success. But also what I'm really excited to see is how much easier did we make it for the sales team to sell the product? And I'll be watching very closely for that. Because when you're not ready yet the sales discussions are very difficult. You're really trying to push a product that's not ready. But when it is ready, those discussions, all of a sudden should become a lot easier.

Christian Beck:

I also imagine in a lot of the startups that we work with, sometimes it's the time to value. Sometimes the value can take a while to prove out. And it's like, initially when you're selling it, you're selling on the promise of a value. Once you actually have something out there, you can actually have data to back up that, "Hey, we actually can show an ROI on this now." It definitely makes that conversation a lot easier.

Erin Chan:

Yeah. And being a startup who has gone down the funding route, these numbers and these milestones are incredibly important to achieve. So there is a lot of pressure on the team to deliver and get those numbers.

Anna Eaglin:

So, Christian, that was a great conversation with Erin. What would you say are some of the key insights for our community?

Christian Beck:

She covered a lot of ground. The one thing that continues to stick with me is hearing her journey from leading someone else's product to leading her own product. And I just kept imagining the way that everything changes. So there's a lot of aspects of running product that all of a sudden become a lot more personal. But I think what stood out to me is that a lot of the key skills or the key activities she did as a PM for other products, she still does now. And I think that, that's what helps her. So for example, I know we talk about talking to users all the time, but she genuinely does that a lot. It's really easy to, I think, build a practice of talking to users when you're building someone else's product, because you maybe aren't as intimately familiar with them, or you maybe aren't even an end user of the product.

Once you shifted over to founding something that was based off of her own personal experience, and now she's got really personal interest in it, she still is talking to those users. And I think now it serves a different purpose. It almost makes sure that she doesn't get confirmation bias or tunnel vision of just trying to execute things that are in her head. It still gives her that separation between the product. So I to hear and just paint that picture. The other thing that stood out was the focus that she put on prioritization. But I feel like maybe you might have some more to say on that, Anna, because I think you do a good job of that, even in your own work.

Anna Eaglin:

I agree with everything you said that a lot of the skills that she learned that made her a successful PM have seemed to have made her a very successful founder, at least in a very product led company. And yeah, prioritization is huge. She's used to being, like she mentioned being in Shopify, a large company, and almost the microcosm of what she's doing now. It's a big company, they have a lot of resources and they can do anything, but what is the most important? What is the biggest problem to be solved? So you think it's almost like... I thought it was really interesting that she talked about to be a great PM, you have to have a growth mindset. And I think you could easily see that that one of the threads throughout her journey has been that growth mindset that she is always willing to learn. And she's always willing to take in new information and adjust to a situation. And I think that to be one of the most important skills for a PM, and then also as a founder starting a new company.

Christian Beck:

Yep. Definitely agree. I have actually one question to throw your way as you're talking is reminded me of another aspect she talked about, which is user feedback. And she talked about the story at Rhenti and we asked her what was something that surprised you and something basically the initial concept that they designed was a little bit too forward-looking and they weren't ready for it. And so I asked her, what about that told you that they weren't comfortable and her answer was good, but I couldn't help but think for a lot of product managers, that's actually a really hard thing to do is figure out how to actually analyze the data that you're getting. And so I'm curious from your perspective, when you look at feedback from people, what types of things are you looking for to really hone in on when you're talking to someone to understand how they feel about something? Or can you even do that?

Anna Eaglin:

That's a really good thing to call out because I think it's important to understand that in the product world, there are multiple right answers to the same question. And so from user research perspective, you understand a person, you get at that what they will want to accomplish and how they want to accomplish it. But then when you build a solution to solve that problem, you can solve in so many different ways. And that's where a lot of times you are user informed, but then you bring in some of your product expertise to solve that problem. And sometimes you just overshoot your user or the person using your product, you've just pushed them too far ahead.

And I think we saw... I don't know, maybe a good example of that is how ChatBots were just everywhere all the time. And I think we saw them as we have a problem, here's one way we can apply a solution that's like a ChatBot. And a lot of times that was just too much for people. You know what I mean? It's a one way to solve a problem is that people want to be guided through a process, but maybe let's stick with a wizard before we jumped to a ChatBot, if you will. That sounds like a really good science fiction novel.

Christian Beck:

Or maybe it's like the segue and all we really wanted was a lime scooter. Recipe segue.

Anna Eaglin:

Exactly. There's that PM [inaudible 00:33:03] of you build the bike and then you build the scooter and then you build the car. Honestly, sometimes it's a strategy to be like, "Check out this car." And they're like, "Whoa, that's too much for me." And then you can understand where they fall. What's their threshold of innovation. People are very different in that way. So I think it's a matter of as long as you have a good why, you can adjust how you're solving the problem, but just making sure that you are solving the right problem. That's the thing that's really going to throw you off.

Christian Beck:

Anna, and what else might be at play in her story is that in tying together what you said, if there's multiple solutions to problems, some of them, even if they're innovative, they could work. Maybe even the idea that she had could work, but it would have maybe say required content marketing. It would have required a lot more handholding by customer success. So maybe there is ways that they could have made people more comfortable for it, but that's just maybe not the best way for them to be set up. You can already get a sense for the way the company is growing the product right now has got to align with the way that you're serving users. And so there's the Teslas of the world that are very forward looking and then they have a marketing engine and a wild CEO to back it up. But for a lot of us, who are starting products, you don't necessarily have that luxury and so you have to treat it a little bit differently and solve it in ways that you yourself can support.

Anna Eaglin:

Yeah. That's a good point. It's sometimes... We've talked to founders who had a crazy idea and people, I don't think got it, but they were dedicated to educating the market on it. And you're right. So they had a total content play to be like, "We are going to teach people that this is the thing that they want, and we're going to make that investment." And other people, you need to, I don't know, put the frog in boiling water. Slowly turn up the heat a little bit.

Christian Beck:

Wait what now?

Anna Eaglin:

To get it to where you want it.

Christian Beck:

Do I have to eat the frog too?

Anna Eaglin:

I'm not sure how the... I guess that's the only reason you would cook a frog is to eat it.

Christian Beck:

Yeah, to eat it.

Anna Eaglin:

You know that analogy, right? The frog won't know that the water is being turned up if you turn up slowly.

Christian Beck:

I do know, but I like to react like I don't know. Because then it makes it awkward.

Anna Eaglin:

It is.

Christian Beck:

There is also a gym by the way, called Eat The Frog, which is weird.

Anna Eaglin:

I think that that's a different metaphor. I think that that metaphor is like, do the thing you hate the most in the morning. So if you're going to eat the frog though, you should heat it up slowly. Okay.

Christian Beck:

Yeah. As a sick experiment for whatever reason.

Anna Eaglin:

Yep.

Christian Beck:

Okay. So this needs to end.

Anna Eaglin:

Join us next week as we continue the series on How to Learn Better Product. I'm Anna.

Christian Beck:

And I'm Christian, and this is Better Product.

Anna Eaglin:

This is Better Product. Thanks for listening to the show this week. If you're looking for more resources on how to design, build, market and sell better products than head over to betterproduct.community to join well, the community. And as always, we're curious, what does better product mean to you? Shoot us an email at podcasts@innovatemap.com.