From PM to VP of Product: Jiaona Zhang’s career advice from Webflow, Airbnb & Dropbox

 There are so many product topics that you and I could chat about. Um, but I think what stands out to me most is how you've crafted your career in product. You've worked at these amazing companies making your way from first-time PM to now VP of product. And so I'd love to dig into that more today and specifically your framework here.

And you've said this to me before, you know, you think of it less as a career ladder and more about three distinct phases of the career journey. Why is that? And why is this an area that product folks and founders should spend more time thinking about. 

 Yeah. So I really think that the career ladder can be so different from company to company, which is why I really like to think about it as three different phases where you're directly contributing as a PM. And then when you're managing PM's and your impact is actually through your team. And then finally, where you're leading the entire.

And, you know, each of those phases are really quite different, you know, how to navigate them, how to be successful in them is quite different. And as a company grows, you know, to your point around, you know, why is it important for founders even think about this? Um, you know, you need people to do the different types of work across these three dimensions, and it's really important as your company scales

 So before we dive into your thoughts on each of these phases, I was curious, are there any commonly held beliefs or advice on product careers that you disagree with? 

 maybe I'll start first with this one, commonly held belief, which is that you have to be technical in order to be an effective PM. And I think that is in conversation a lot, especially with people who are thinking about moving into. I think it's a lot less about being technical in order to be effective.

 Um, you know, for example, I myself did not have a CS degree. I had an econ degree, but it's really more about asking the right questions and using those questions to guide your team. another really commonly held belief is that the best way to get started is actually through a structured APM program.

And, you know, I do think they're great. And if you can get into one, like you take the opportunity, but what's even better in my mind is the combination of a really committed manager. Um, and you know, a lot of times with APM programs, you actually don't know who your manager is. And even more importantly than that is having more work to be done at that company that you're at at the stage that they're at, then you have people to do it.

And then I guess the last commonly held belief that, um, I would challenge is some thinking around this idea of finding role models. Um, I think it's really about fighting. Advocates. And then if you are looking to model your behavior off of someone, I'd really recommend finding someone who's just a little bit ahead of you and understand, you know, what have they mastered recently to be successful, as opposed to finding a person that, you know, you might want to be in five years or 10 years.

 I love those. Okay, awesome. So maybe we start JZ by kind of framing the product manager job. Uh, what do PMs do and, and what does the day-to-day look like? 

 the PM role really is different from industry to industry and even company to company and sometimes team to team. And so what I will probably do is break it up into the following pieces. The first one is a big part of your job is just understanding what to build.

 And you do that by understanding your users problems and also really defining what business success looks like in the context of your particular company. Then it's about working with a team to build a solution and like the actual product itself. And as part of that, you're working with, you know, a lot of partners, marketing sales support to effectively get whatever it is you've built to market.

There are so many great products that are great products, but without that go to market motion are not successful. And then finally, it's, it's closing that loop. Almost no product is the perfect right product the first time around or . And so you really have to iterate, you have to learn from user feedback, you know, the data you see and then use all those things to improve your product.

And so I guess your question around the day to day, a lot of that is really just doing a lot of communication. You're communicating with your users. You're understanding them, you're communicating your team. You're making a really clear to them what success looks like and what you've learned. And then you're communicating with, you know, those partners and your stakeholders.

 And so given that set of responsibilities, who is a good fit for being a PM or I guess conversely, why should you not become a PM? 

 yeah. Great question. Um, in terms of a good fit, you know, I just mentioned a lot around this concept of you're spending a lot of your day collaborating and communicating. So I think to be a good PM, you have to really enjoy that. And that doesn't mean you're an extrovert or you're talking all the time.

You know, I actually think that written communication is, is equally important if not even more important, but you have to enjoy the process of communicating and all of the details that come with that. Um, another thing that I think you have to be really good at is actually sweating the details. So having that deep care for your users and the ultimate product experience, if you don't sweat the details, it's so easy for low quality products to slip through.

And then I also think you need to be intensely curious. You, you know, you have to be really curious about what do your users actually want, what is the right solution for them? And you have to be not afraid to take initiative. You know, a lot of times, you know, the thing won't happen unless you put it in motion somehow.

So the combination of having that really deep curiosity and that proactiveness go do something about it is really. critical. Um, to your point about like, what are, what are the things that you should not maybe, you know, think about or care about if you really want to be a PM? I think there are several actually, um, I think the first big one is, you know, if you want to be a PM because you want to make all the decisions or dictate what the team should build, um, it's not gonna really work out.

You know, I think there's that common saying out there, which I actually find very problematic, which is, you know, as a PM, you're a mini series. Um, instead like, yes, you have all the accountability, but you have very limited. In fact, oftentimes no direct authority because nobody on the team, the engineers, the designers, nobody reports to you.

And so, you know, in many ways you're an editor, you're taking all these inputs and figure out what to do with them, as opposed to let's say like barking out orders and expecting your team to snap to them. So that concept of like, if you want to be a PM, because you're like, I'm going to make the decisions, it's probably not going to be the case.

 Totally. And the, the, the mini CEO thing I think has always kind of rubbed me the wrong way as well. And I 

love the sweat, the details thing, you know, Dropbox core value. So we connected on that. 

Um, JC, what is it you want to tell us your personal backstory? What is the backstory on how you initially became. 

 Yeah. So, you know, I served my career and actually, um, worked in consulting. That was the natural path. It was either banking or consulting coming out of school, then econ major. And after working consulting for a little bit, I realized that I really craved I'm actually building something. So I spent a lot of my time, you know, doing research, putting a deck together, making a recommendation to a client and then walking away and just hoping that they'd implement, um, the recommendation.

And I really wanted to actually be on the other side of the table where I was building and operating and working with teams directly. And so, you know, at the time I actually really didn't even know that product management was a role. Um, I was looking around to see what, what would allow me to do that.

And it was actually a little bit disheartening at the time because, you know, I learned that. To be a product manager. Um, you, for a lot of companies, you know, let's say the Google was out there, you had to have that computer science degree in order to even be considered for an interview. And so, um, what I ended up doing, you know, my, my journey to becoming a PM was I actually found a startup.

It was called pocket gems. Um, it was a time where gaming was really taking off. It was, you know, during Zynga's heyday. Um, and so I found a company that, uh, was in that space and they really valued PM's that brought a strong analytics background. And, and that's what I had, like working in consulting with my econ major.

Um, and also I wanted to beat one somewhere small, which is why I went to like a pocket gems instead of like a Zynga. And I wanted specifically to be working on. Building on mobile because I really felt at the time that was the future. And at the time, honestly, I think Facebook didn't even really have a mobile app.

And so that strong conviction and where the world is going and also wanting to be in a place where I would be learning all the time and have a lot of responsibility because the company was so small, that's what drove me to pocket gems. Um, and to get my first PM role there

 That's awesome. So I guess maybe on the advice side, you know, and it could be for, uh, somebody who wants to switch into PM from a different industry or someone who's a new grad when you're early in your career, and you're looking to join a company as a PM. What should you be on the lookout for?

 And are there any specific questions that you, that you recommend asking maybe during the interview. 

 Yeah, I think that when you're early in your career, it's all about how much you're going to learn. So I would really, you know, ask the questions and, and walk away feeling like this place is where I'm going to learn the most, this group of people that I'm going to be working with. And I'm to be surrounded by they're going to help me and push me the most.

And also it's the network, um, that you kind of establish in your earlier career that really builds over time. And, um, it's just compounding. Um, I think there are a lot of questions you can even ask in order to gauge whether or not you're going to learn it and that rate of learning.

So things like asking your manager, how do you define success for me over the next six months over the next year? And what are the biggest challenges that I will be facing? How do you see me growing? Or, you know, what are the most important skills for me to be successful both here, but more broadly in my career as a PM, those types of questions will help you understand if your future manager is going to be invested in our growth and also whether or not the challenges that you're going to meet are actually things that will push you to grow as opposed to potentially challenges that you have no control over.

That can actually be very disheartening. Um, the thing that's a lot 

 can, let me jump in, like, what are good answers to those questions? Like if you were to ask a perspective, man, Hey, what are the biggest challenges I'm going to face? How do you see me growing? What are good answers to these questions that you want to hear? 

 Yeah. Well, first of all, getting answers to those questions is really important. There are times when, um, you know, for a first time PM their future manager could very likely be a first-time manager. That's not a deal breaker at all, but even having someone who has been thoughtful about providing those answers for you, that's not a given.

 but specifically, I think, you know, going back to this challenges question, if the challenges that they're articulating are things where they're like, Hey, this is a challenge, but this is how you can learn from it and overcome it. That's great. Versus like, Hey, an, a challenge that we're going to be facing is something that is pretty large, pretty strategic, at the company level, then you're going to be in a situation again, going back to this concept of like not having the control to then, you know, learn and iterate on, on what's ahead of you.

 Got it. let's switch gears a little bit. I know that you actually teach a class in product management at Stanford. Uh, I'm curious, what's the first lesson. What do you.

 Yeah. So, um, the first class covers the product life cycle, um, which is important because that's essentially what you're doing as a first time PM really getting features through the entire lifecycle. But specifically we go deep on this one concept, which is separating the problem space from the solution space.

So, so what is that? Um, a lot of times people jump straight to solution. They're like, wouldn't it be great if we built X or like, wouldn't be great if users had Y and that's a huge mistake. You've, you've skipped the most important part of your job, which is actually understanding the problem and the opportunity.

So the problem for your users and the opportunity for your business. And so the first lesson is really even helping students identify that that's a thing that happens And that most likely 90% of the time they've jumped ahead. And so pulling them back into the problem space and helping them understand how to navigate that.

 Got it. And related to that, I mean, you mentioned that as a challenge that a lot of PMs face, what are the other big challenges as an early career PM and maybe what are some of the most important lessons that you learned in your first few years?

 I think that the biggest mistake that I see first-time PMs make is that they spend way too much time trying to prove value. It's almost like you want to be accepted by your teams. He spent all this time doing, you know, pretty low leverage tasks, 

 Like cleaning a bugs or project managing or, you know, chasing down a very specific thing. And again, those things are important. I have this concept of like, you know, you're both looking at the big picture and then you're also going down to the details and you need to be responsible for them. But if you get stuck doing those low leverage tasks all the time, that's a big mistake because your job success is actually building a great product, not just, you know, making your team happy or executing on what you've been given.

 And what's an underrated quality. Do you think of, of great PMs or a skill that you don't see PM spending enough time on in the early careers? 

 I would say it's saying no. So it's very hard to say no, I think generally as a human trait, it's difficult to say no, but it's so important for the PM to do that. And it's not always intuitive. You're like, well, why is it so important to say no, the reason is because how much you are usually asked to do is always greater than what you're able to do.

And so being able to say no, not that. That is the essence of good prioritization. Another thing that I don't see PM spend enough time on is actually working on their communication. So I mentioned earlier that so much of your job is just communicating. And so spending the time learning to be really concise, concise emails, concise slacks presentations.

I'm also thinking about how do you tailor your message to an audience because you're gonna be speaking to all these different types of people, whether it's users or your direct team, or to leadership, tailoring your communication and your messaging is critical.

 Are there any tactics that you found particularly useful when you were early in your career, either in terms of building features, working with engineers, communicating internally, et cetera, like what are some of these tasks? 

 I'm actually going to share something that isn't specifically about what you asked me, Todd, in terms of, you know, building features or working with engineers, I'm going to share a thing that I thought was really useful for me. And that is also very tactical. And that's almost like a Metta point, which is the piece of advice I would give is actually become really exceptional, become known for something at the company.

And what that means is, you know, again, you don't have to be good at everything, like shoot for exceptional at that one thing, you know, pretty good at call it like one or two other things. And then at least average, like get to table stakes level with your other skills. But the reason why it's so important to be exceptional, that one thing is then people will come to you.

Your teams leadership will come to you with more and more opportunities because they know that you, um, really are great at a particular thing. And that's how you get more responsibility. That's how you have more. And so, you know, tactically, I'll give you maybe some examples from, from my career when I joined pocket gems.

Um, the thing that I really strove to be known for was to be, um, operationally excellent, but not just operationally excellent. Someone who could drive business outcomes. And so what I worked really hard on was, you know, owning the biggest live game and generating the most amount of money out of that game.

Um, because I knew I wasn't the most technical, but not even close. I literally was like, I don't understand a lot of these things And again, it was great because I was learning so much. Um, I also wasn't the, the person who was best at fun gameplay design, like before pocket Jones, I, if you ask me about certain camps, I would be like, I have no idea what those things are.

And so, because I knew that I couldn't shine in those areas, I could just get to, again, table stakes, understanding I worked really hard to become exceptional at operational excellence and that business like leadership and, and driving business outcomes. And so then when I went to Dropbox, you know, I had a similar mindset of like, how do I become known for something where I could be given more and more opportunity? And what I found that I could become really great at was that I could become the person that was known to be able to get the most complex launches over the finish line and do it with the leanest team.

And the way I thought about it was I didn't want to be known for the exact same thing. I was known for pocket gems, because from a learning perspective, I wanted to be in a slight different scenario and situation, but that being said, I was also thinking about my core strengths, like, because I was so great at execution.

Um, I can translate some of those skills into working through these like complex technical launches and working with very lean teams and inspiring those teams. Um, I actually think even to this day, people at Dropbox have this like nickname for me as a Honeybadger, which again, I'm not sure how flattering that is given some of the YouTube videos out there.

 Oh, I think it's flattering, honey badgers are known for like relentlessness and ferocity. 

 Yes, but hopefully also empathy, which is what I think is also important as a PM. Um, but just even just like having that as like, oh, this is what Jesus is good for, put her on anything and she'll kind of relentlessly drive through it. Um, you know, I think what just really helped give me more opportunities and therefore more learning experiences,

 Awesome. And then, so Airbnb, we work, was it? Same thing, different 

 different things. And I think it's related to this concept of like, I wanted to push myself. I want to be known for other things, because as part of that, I would be learning growing in very different ways. So Airbnb, I actually, you know, became the person who, you know, was really known for team building.

And that was again, very different than previous experiences, where it was more of an IC and individual contributor. And then also, um, this was a new challenge for me personally, but, um, I actually became known as someone who was a deep systems thinker. I worked on a lot of platform work and could see how things across business lines could tie together.

And we could do really interesting platform investments to bring that to life. And that for me was a very different challenge than execution, which was a little bit more what I lean into when I was a direct PM. Right. You know, at pocket gems and at Dropbox. And so, yeah, I became known as the platforms person, which is, it was surprising to me, but, um, was something that, um, pushed me to grow in a lot of ways.

And then Uh, we work, I became the person who could really translate between, um, all the business teams and the rest of the company with the actual like infer team. And so it leaned on some of what I'd picked up at Airbnb, this concept of being that translator, that systems thinker.

But I pushed myself to go a lot deeper. I actually worked on, um, infrastructure for the very first time. And, uh, the reason I did that was because I seen so many PMs that had only done feature work or only infrastructure, and they were speaking different languages. And I knew that ultimately, if I wanted to be a really great all around product leader, I want to have worked on both sides.

So I can actually see the points that the two sides were making and bridge that gap.

 I think this is an incredible piece of advice about being known for something at a given company. It strikes me that the four examples that you gave JCR are pretty different, right? Pocket gems, running live games better than anyone else, Dropbox, most complex launches, Airbnb building teams and thinking about platform.

And then we work with infrastructure. Like what's the advice that you'd give there, like, because these are very different things. Um, they're all good. And in what ways are they related or how did it come from a core part of you that made it possible to be good at all these different things? 

 speak first, the motivation, which goes back to a lot of what I was talking about earlier, which is this desire for learning. And that's honestly what I think people earlier in their career should just optimize for. So the reason that these things feel different was because at every company, I wanted to push myself in a different way and become excellent in a different way.

Um, but at the end of the day, you know, I do think there are some similarities. I think if you, if you pick a thing that is just so out of your comfort zone, the chances that you're going to be exceptional at that thing is, is pretty low. And so I think you see some threads in here, one thread being, being able to get things done, right.

That's what really drove a lot of the earlier. Reputations, I would say, and then I took that and I was able to say, okay, well, that's not enough. And I think, especially when you become a manager and a leader, we'll talk about this more. It's not enough to just be operationally. Excellent. It's really about that strategic thinking, that critical thinking and being able to motivate teams.

And so, because I knew that was so important in being a great product leader, I pushed myself to learn those things, um, and get good at those things. 

 Got it. So, I mean, these are household name companies, Dropbox, Airbnb, we work web flow. Is the PM role the same at all of these companies? Or is it very different? 

 Yeah. I mean the PM role is always different. There are times where even the title PM is different company by company, you know, at Microsoft, they call them program managers and sometimes they even call them product owners, um, or even producers.

 I also think how practicing is actually get made really differs by company in terms of how involved founders are, or what stakeholders need to weigh in the feature development process is also really, really different company by company or their product reviews, design reviews, what are the phases?

And then it can even differ by team the exact role and responsibility of the PM versus the ESM or the designer that can differ. Okay. So let's flip it around now to the founder point of view. Cause there's a lot of founders who listened to this podcast for early stage founders out there. What are the signals that you need to hire your first PM? 

I think by the time that you actually have an engineering team call it seven to 10 engineers, and you're no longer spending your own time, essentially being the PM. I think that's true for many, many founders at the beginning. It is time to start thinking about that first PM. Hire.

 Okay, awesome. And who are you looking for? 

 you definitely want to find someone who's cut their teeth somewhere. Um, who's excited to be that first PM and the impact that comes with that, um, it means that, you know, they have enough experience that they can do a good job and they may even be able to start building out a team, but it's not someone who comes in expecting that they have a team under them or the way they get impact is through others.

 You, your first PM needs to be able to execute and get in the weeds, you know, very, very quickly

 And so what's the, advice to founders, what's the best place to look? How do I identify these PMs? Who might be my first PM? 

 Yeah, I think it's finding those people who have seen hypergrowth. And, um, one other tip is find someone who might not have the opportunity they have, whether it's management or in kind of the scope that they want at an existing company. And so they're kind of motivated and craving to do more, but they've been at a place where again, they've seen some of the things that your company's likely going to see over the next couple of years.

 The hyper-growth thing is interesting to me because I think sometimes it's not possible to find PMs who have seen hyper-growth at a prior company, or sometimes maybe I think you want to take a bet on a, on a PM who hasn't necessarily done it before. is that controversial to you or do you, uh, do you agree with that in some ways.

 I think a lot of times you can take a bet on an internal candidate and the reason it's worth doing that for an internal candidate is because usually they have contexts. That's very, very helpful. So for example, there's someone who sits on your sales team on your support team, um, or maybe on your data team.

And they just see so much of that user feedback or that data that would enable them to make great product decisions. So I would say, you know, I personally would not hire someone who's never done it before and take a bet on an external person, but I would potentially take a bet on your first time PM on internal candidate.

 I love that. And I've seen a lot of examples of that, where you take someone who's in a non PM role, but they know the customer really well. They know your company really well, and they turn out to make great PMs. 

 So let's, let's transition now and move up the stack a little bit from the individual contributor PM to the manager phase, uh, when you're managing a team of PMs. So what changes when you start managing, and then eventually when you start managing managers, 

 yeah. The biggest thing is that your impact is now through your team and not what you do yourself. So you have a lot less control, but you actually have a lot more influence.

I think someone who actually enjoys having that impact through others, you know, enjoys coaching, enjoys, helping people make good prioritization decisions, helping people execute. these things, make someone more fit to be a great manager. why should not offer the leadership track if you really like having that direct impact?

So again, not through others, but yourself making those decisions, having that control, you know, that's not a great reason to move to management. In fact, we have call it principal or staff PM roles for you there. Um, another big thing, you know, if you, if you find yourself unable to be what I call an emotional dampener for the team, meaning like, Hey, I know my team is really upset.

I know people are frustrated, but I'm going to coach them and help them and kind of like. Uh, dampen the emotions as opposed to rile them up. That's a really important skillset of being a good manager. And so if that's not something that is easy for you, I think you should think twice about being a manager.

I think there's a saying of like a good manager is often, you know, a punching bag and a therapist in addition to having to do all these other things around, um, setting strategy. And so I do think knowing that, and going in with eyes wide open is really important.

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Jiaona Zhang shares her framework for building a product career—from PM, to manager, to exec—with tactical advice and frameworks from her time at Webflow, Airbnb, WeWork and Dropbox.

From PM to VP: Product career advice from Webflow, Airbnb & Dropbox

Jiaona Zhang shares her framework for building a product career, from PM, to manager, to exec.