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

Todd Jackson: JZ. Welcome to the show. 

Jiaona Zhang: It's great to be here, Todd.

Todd Jackson: 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. 

Jiaona Zhang: 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.

Jiaona Zhang: 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.

Todd Jackson: 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.

Jiaona Zhang: 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.

Todd Jackson: 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? 

Jiaona Zhang: 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.

Todd Jackson: 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. 

Jiaona Zhang: 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?

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

Jiaona Zhang: 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 

Todd Jackson: 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? 

Jiaona Zhang: 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.

Todd Jackson: 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.

teach in your class? 

Jiaona Zhang: 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.

That's critical.

Todd Jackson: 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, 

Jiaona Zhang: 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? 

Jiaona Zhang: 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? 

Jiaona Zhang: 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.

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

Jiaona Zhang: 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,

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

Jiaona Zhang: 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.

Todd Jackson: 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? 

Jiaona Zhang: 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. 

Todd Jackson: 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.

Jiaona Zhang: 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.

Todd Jackson: 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.

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

Todd Jackson: 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? 

Jiaona Zhang: 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.

Jiaona Zhang: 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.

Todd Jackson: 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. 

Jiaona Zhang: Yes, absolutely.

Todd Jackson: 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, 

Jiaona Zhang: 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.

Todd Jackson: As someone who has reported to emotional dampeners in the past. Criteria. And I think it really does make for a, a very warm and supportive managers. I've, I've definitely benefited from that in my career.

Jiaona Zhang: it completely changes your ability to feel like you have autonomy and work. So it's huge.

 So what advice would you share with a first time, man? Is there anything that you think is important to pay attention to as a people manager that is unique to product or to managing product managers, 

Jiaona Zhang: definitely, as a first-time manager, the biggest thing to think about. What got you to where you are is most likely not going to get you to the next point, which is, you know, a lot of times what got you to where you are is that strong execution, that ability to get in firsthand and debug something, untangle something, and that's not what you're doing anymore.

You are coaching, you are supporting, you're helping your team and your influence is through, you know, your reports. specifically to managing product managers, a big part of your role is actually setting strategy, like taking the vision and strategy at the overall company level, translating it down to your particular area.

And then you're also managing a portfolio. How do you balance all the levers, all the investments, all the work within your area of influence.

Todd Jackson: So let's focus on strategy and maybe we can demystify strategy a little bit, because I think a lot of people think of it as this, this big concept. That's hard to understand. How do you think about strategy and how do you think about moving from being an execution oriented PM to a more strategic thinker? 

Jiaona Zhang: Yeah, absolutely. I know so many people who really do get overwhelmed by this, this word strategy. It feels really daunting and we're like, what is strategy? Um, but it's actually quite simple. Strategy is what are the things you're going to do to get to where you need to go. And so part of that is first defining where you want to go.

And that really is defining success, defining your goals and then working backwards and saying, okay, these are my levers to get there. Like, what is each lever? How much do I want to invest in each? And what is the sequencing behind the things I want to do?

Todd Jackson: So when you talk about levers to achieve success, what do you mean by that? 

Jiaona Zhang: Yeah. So I use this term and actually, you know, I teach about this in my class because I think a lot of people, when they think about a roadmap, they will literally Les out all the features. I've seen so many people just create like an Excel spreadsheet and you're like, these are the features and I've raced them all.

Meaning, you know, I've like estimated the impact and the cost. And I've compared to everything that is not how I believe we should be thinking about, you know, strategy or your roadmap again, which is a reflection almost of your strategy. Instead. I really, I stress a lot around like telling human stories.

So you're able to say this. Bucket of work. And there's a theme around that bucket of work. You know, someone could could say it in 30 seconds, like this is what we're doing for our users. It's really important to get to that level of storytelling, communication. And that's what I mean by lever. So what are you doing?

You know, a, B, C these three things we're going to do these three buckets, these three levers. When we do them, we will accomplish our goal. And then that way, you know, everyone, that company, whether it's your own team or your leadership team, they will understand what your strategy actually is versus. 50 features in this order.

And then people can have debate around that. They can say, Hey, I don't know if this makes sense, because we learned this new thing or, you know, is, is the sequencing of that bucket. And then this other bucket, does that make sense or can really do these in parallel or should they be flipped? And so that's what I really mean by levers.

And I think this whole concept of strategy is at the end of the day, you're telling a story and that story is based on what you know, right. what your you've learned from your users and your data. And then you're saying, this is the path we're going to take to get to where we want to go.

what were the most important lessons that you learned in your, in your own career and your own journey from individual contributor to manager? Are there any mistakes that you made or failure modes that you see. 

Jiaona Zhang: My biggest learning is actually. Much more time on this concept of defining success at the end of the day, you know, you're not here to come up with the right answer. You're not here to figure out the, how you are here to empower an entire team or several teams. And so in order to do that effectively define success for them in a way that they fully understand it.

And they feel empowered to go, come up with their own solutions. People just get into the weeds and they start, you know, pair program solving with our teams and it might be fast for the first time around, but that's actually not how your team learns and is able to problem solve on their own and come up with their own innovative ideas, which at the end of the day will always eclipse yours because the number of people, the number ideas, how close they are to the actual details will be greater than you as a manager.

Another thing that, you know, related to this concept of defining success is actually drawing the box a little bit more concretely. And what I mean by that is a lot of times, you know, you're either on the spectrum of like, Hey, go do acts, which we should never be doing.

We should be like, this is a problem you should be solving for, or the outcome we should be achieving. Or it's it's on the whole other side of the spectrum where it's like, Go figure this big ambitious thing out. And it's so big and ambitious, it doesn't match the skillset of the PM. That's actually working on the project.

 if you say something like, let's go figure out, um, the next evolution of Dropbox to a senior PM, they're going to be like, wow, that is a big, big, big ask. You know, how do you draw the box a little bit smaller for them?

Jiaona Zhang: So you're able to say, Hey specifically, we want people to be collaborating more with Dropbox. How do you think about that specific problem? So I do think, you know, people can err on the side of one or the other being way too specific or being way too vague. And that's a balance that I've really worked through and I'm kind of grown from throughout, throughout my career.

Todd Jackson: So this idea of drawing the box, I think it's a great metaphor. do you draw the right box? Like where, how have you learned to do this and to make the box appropriate for the level that the person that you're talking to is at. 

Jiaona Zhang: I think that there are two pieces to this. The first one is understanding the company strategy very, very deeply. I think sometimes managers can just get into the act of quote-unquote managing and they start doing the thing. They start coaching without really being like, wait, wait, do I understand how my team, my area really ladders up to the overall whole?

Like where are the open questions and the company strategy that I don't understand, because if I don't understand those holes, I can't then make it clear to my team and then create leverage for everyone beneath me. And so I think the first piece of dry in the box is like, do you have a really clear understanding of the company's strategy of the opportunities of your user base so that you can help draw quote, unquote, a box for your team to really.

 and then on the other side, it's really understanding your team and rapport. What are their strengths? What are their weaknesses? How did they approach strategic thinking? are they good at goal setting themselves and knowing their strengths and weaknesses will help you draw the box in a way that is the right size and the right focus area for your particular report.

Todd Jackson: And so I imagine that when you're working with a PM, who's a bit more junior. You draw the box in a kind of narrow fashion. And if you're, if you're working with a PM, who's more senior, you draw a wider box and more expensive box for those senior folks. Do you give them these wide open thought exercises and then just sort of let them run?

Or when you draw the box really wide for a senior person, how do you then manage it? 

Jiaona Zhang: Yeah. So the way I think about it is if you are working with call it a first-time PM, you're drawing the box, uh, both narrowly and with a thick marker, meaning, you know, meaning you're like, okay, this is the future that we're trying to do. This is the goal that we're trying to achieve. And you tell them both of those things, then as they get more senior, right, you no longer have to tell them, this is exactly what you have to build and said, you can be like, I don't know what we're going to build per se, but this is the outcome that we do achieve.

And then they can actually go in and start drawing their own boxes or like filling in the box, um, in terms of what exactly we're going to do and how we're going to do it. And as a person gets more senior, you know, to your question, sometimes their job is to draw the box with you where it's like, actually, what problems should we solve for the company at this point in time, a very, very senior PM and especially a PM, you know, leader manager of a particular area.

It's part of their job to help draw that box.

 So when you are looking for PMs to bring onto your team, what are you looking for in candidates? I've heard you talk a little bit about different PM archetypes, and I'm wondering if you could go through those here. 

Jiaona Zhang: yeah. Overall, you know, when I look to brown PM's I really look at their communication skills, you know, their ability to think critically and from first principles. But yes, I definitely do have some archetypes Because the type of PM you hire on a team with very specific work, looks different and the skills that accompany that, um, do look a little bit different.

So I think a lot about, you know, the first archetype being a growth PM. You know, these are the PMs that are on a growth team. There's a lot of high velocity experimentation. Um, those PMs are very metrics driven. They like optimizing and working very, very quickly and getting learnings very quickly. Um, the next archetype I think about 

Is this concept of a core product PM. And this really is the biggest bucket of PMs. You know, these are PMs that, work on existing features or net new features. Um, they sweat the details of the user experience. They really, really understand, um, user problems. They go into the data, um, and they're able to really, um, improve a feature set or a product.

area. Uh, the next archetype is what I call more of a platform PM. And this doesn't apply to every single company, but I do see a lot more companies thinking about, you know, how do I actually build a platform that gives me the ability to move faster in the future, like, you know, high, upfront investment to build the platform, but this platform will then enable us to scale faster to do something that is a repetitive thing over and over again, much easier.

And so that kind of person is someone where it really is important that they are strong systems thinker and that they can both understand the business need, but then understand the system that is needed to support the business. So this was a very difficult person to find because a systems thinker, in addition to a, business driven mind is not necessarily easy to come across in, in one person.

The next one is more of an PM. And again, by company, there are times where, you know, these are less PMs and more TPMS or technical product managers or technical program manners. So depending on how strategic infrastructure is for your company and for your team, you know, do you sell some of it as a product itself?

Is it going to give you an unfair advantage, um, that changes whether or not you have an actual PM on it, um, or not. And then finally, um, you know, this last one, I think like you could take some of the other PMs and have them do this type of work. But I think in general, like they're motivated by different things.

This concept of like a zero to 1:00 PM, they're really into prototyping. They love the early phases and by the time it gets to, you know, one and it's like sailing from one to a hundred, they're just less interested. Those PMs have a very specific skillset and also a thing that motivates them and they make them unique at that stage.

Todd Jackson: so five different archetypes you gave there. I imagine that the interview questions that you ask them are going to be pretty different across the five types. What are some of your favorite interview questions? 

Jiaona Zhang: Yeah, I do think there are some standard questions that actually think apply to all the rules. But yes, of course, if you're going to dig deeper on a specific area, you're going to want to, um, test for that specific skillset. But the common ones that I do ask is, you know, just really understanding their product sense.

So, you know, what are your favorite products, but more importantly, like why are they your favorite products and seeing if people actually spend the time thinking about the things they use it a day. Um, I'm a big fan of an analytics question at the end of the day, every PM is going to have to be analytical and think critically.

 And so I typically ask a CEO dashboard question, which is like, what would you actually pull together that you should be looking at from a metrics perspective for a given feature or a given product. and then finally, in addition to the product, since question the analyze question, it's really important to do a lot of behavioral questions because at the end of the day, you know, so much of the PM role is how do you interact with people? And so understanding how they will work with engineering design, all of their partners, asking those questions where you know, this, the hard situations they've been in the failures that they've had, how they've responded, how they, you know, rise to challenges.

Jiaona Zhang: Those behavioral questions are also really. 

Todd Jackson: important. 

and what makes a great answer to that CEO dashboard question? What are you looking for for a top end? 

Jiaona Zhang: I want, um, the ability to synthesize in addition to the ability to go deep. So I think one common, a bad answer is you have a list of metrics and all of them feel like they're created equally being able to say these are the most important metrics. And then if you want to double click into them, okay, these are the secondary metrics that you'd look at.

That's a really big part of having a good answer here.

Todd Jackson: okay. So now you've, you've found some of these PMs, you've made some great hires. Now it comes to how to best support them and how to retain them and how to help them have great careers at your company. What are some of the tactics that you've found work? Well, there. 

Jiaona Zhang: yeah. At the end of the day, you know, people really crave clarity and they want to know that they're making an impact. And so specific tactics include helping people understand how they're doing, doing a actual monthly development chat with them, where they know that they're going to spend the time with you really reflecting on their growth plan.

Um, when it comes to seeing the impact they're having, you know, one of the most demoralizing things is actually for a PM, um, to feel like the product didn't go anywhere. So being able to tie what they're working on with broader goals and ultimately company level goals and company trajectory, that's also really.

important. and then lastly, it's not just about having a clear career ladder. You know, those are important things and some of the stuff I mentioned, but ultimately, you know, people want to be at a company that's really growing and again, growing doesn't have to be your over year annual revenue growth.

It has to feel like they're the companies doing innovative things, moving in a direction that is going to support users and change the world. And so being able to just really understand your report's conviction, the company and what motivates them, and then tying that back to what the company is actually doing.

That's a big part of supporting the team and improve.

Todd Jackson: And so managers, you know, might be thinking about career ladders, but sometimes folks on their team are thinking about whether to stay at the company or switch and join a new company. Um, when do you think it's time to stay put versus time to switch jobs? 

Jiaona Zhang: overall, if you find yourself too comfortable, I do think that's a good time to at least think about, you know, am I growing? Am I learning? And is this the best environment for me to be in that being said, I do think a lot of times people will run away from something and that doesn't usually work out and said, I really encourage people to be like, I am running towards something.

I am really, really excited about this new opportunity, what I'll learn there as opposed to running away from your current situation. Um, if you are feeling like, ah, I'm just really frustrated with my current job, a thing that I'd encourage you to think about is. Are you actually hitting a roadblock? That is truly frustrating, whereas actually how you're learning, because the times when we're learning the most are those times where we're not comfortable and we are feeling like there's some degree of failure.

Todd Jackson: Okay. And let's flip it around for the founders again, as a founder, what are the signals that you need to add more product leadership? And how do you think about promoting internally versus potentially layering here? 

 that's actually a really great question. I think that there are a lot of internal folks that make amazing PMs. You know, as we talked about earlier, they have the relationships, they have the context.

Jiaona Zhang: Um, but at some point they really need guidance from someone who's just seen the story before, who have a lot more reps and can up-level them. And so that's when it's important to really start thinking about adding more product leadership and in terms of, you know, promoting internally, um, I do think it's unusual to have someone get promoted all the way from being, you know, the first PM of the company all the way to head of product of given what I just mentioned before that kind of skill is an experience gap, but it's really not unusual to go from being the first PM to being a really effective, you know, group PM or manager of PMs.

I think a lot of the people who are early again, have that context and that knowledge to be able to really teach other PMs, new PMs, new external hires, how to be successful at a given company.

Todd Jackson: Is this something you see founders struggle with about deciding whether to promote someone from within to be their product leader versus. 

Jiaona Zhang: I do see a lot of founders sit with their first PM for too long thinking that that person will scale for a lot longer than they're actually scaling

Todd Jackson: Got it. Okay. So let's continue to move up the stack here from the manager phase to the executive phase. So now talking about VP of product, chief product officer, uh, what changes at the VP level 

 At the VP level, honestly, the puck stops with you. And so you are responsible for the entire team, you know, ultimately the decisions that get made. And one of the big things that changes is you start viewing the product team as an incredibly critical product in itself. So given that, you know, building the product team really, really should give you energy.

Jiaona Zhang: And that's a big part of what you do at the VP.

 Do you have a thought on what kind of product managers make it all the way to VP versus, you know, the ones who don't make it all the way there and what is the difference?

Jiaona Zhang: a lot of it does come down to what gives you energy. And so if you, if you get a lot of energy from recruiting, which is a huge part of your job as a head of product, um, or org design, another big part of your job, if those things give you energy, the chances of you being exceptional them is higher because you're going to spend a lot of time practicing it.

I think another big thing is, um, you have to get. Comfortable making hard, potentially unpopular decisions. A lot of your job is potentially saying no to a founder, um, or being a hold your own on exec team. And so that ability to hold your ground and have a strong perspective is, is really, really critical to, to be in a good VP.

 I want to go into both of those actually one at a time. So the first one, this idea of team as a product, how do you put that into practice? 

 Yeah. I mean, your org is essentially your strategy and practice. And so I think a lot about how do you, future-proof your org? How do you think about where your strategy is going and make sure that. Design into the way your organization is laid out. I also think a lot about creating processes that scale, you know, when you think about your team as a product, you have to think about the processes that they need in order to be successful.

Jiaona Zhang: So the same way that you think about building a product, where you're thinking about the users and their pain points, you should think about your team and the problems are facing so that you have clarity on what you're solving for. And ultimately you can create processes that really enable people to do their best work.

Todd Jackson: And then what tactics have you found effective for working closely with your CEO or your peers on the exact team or, or even the board? 

Jiaona Zhang: Let's go ahead and start with CEO. I mean, honestly, every CEO is so different, um, but I I'll share a little bit of my experience, you know, for me partnering with lad, who's the CEO, what flow, you know, he's very product minded. Um, originally an engineer went to art school and so my job partnering with him is to really pull him out of being in solutions mode, you know, and it's something you can just default to naturally given his background.

I think in general, zooming out, you know, the partnership between a head of product and a CEO is really about complimenting them. Like how do they think and how do you bring out the best in them in addition to what is the overall vision? How do you translate that into a clear strategy?

And then how do you actually get a whole group of people executing on that strategy at scale? I ran into that at Dropbox too. You know, it reminds me a lot of my working relationship with drew. I'm also an engineer by background, really good engineer. And the idea of, of sort of helping pull him out of solutioning, working together on the why, what is the big strategy?

Todd Jackson: What are the major choices we have to make and then into what we have to build? Um, that was always a big thing for me as well. So that resonates. 

Jiaona Zhang: absolutely. I think it's, it's very common, right? Because a lot of founders, they are used to making the call on what to build from the beginning, because that's how they got to initial product market fit, but it's not, what's going to get them to the next step of their company.

Todd Jackson: Right. And so what about the rest of the exec team? 

Jiaona Zhang: Working with the exec team is a huge part of the job. when it comes to tactics. A couple of things that come to mind for me, the first one is just really making sure there's clarity across the team on who is making, what decision, who takes the lead from whom on what? I'll give you a very specific example on how we've created these relationships on our exec team. So for example, when I partner with , who's my head of engineering.

We know the relationship is one where she takes the lead from me when it comes to why and what we're trying to accomplish. But I do take the lead from her on how, because the engineering team at the end of the day is going to have the most input on, are we going to be able to meet our deadlines? How do we do this in a way that is scalable?

And so knowing who takes a lead from the other person on what things is really, really important to decision making and effective decision making on exec team. Part of that, I think a lot of exec teams do not do this well. A lot of teams don't do this well is knowing when to disagree and commit. And actually what commitment looks like day to day in terms of supporting that decision that that team has made and making sure it's as successful as possible.

 that totally resonates. It seems the idea of disagree and commit is, is easy to say, but hard to be. 

Todd Jackson: How do you, how do you, guys make that work at Webflow? 

Jiaona Zhang: even calling out when we've hit a moment of, okay, we've all disagreed, but now we're committing. I think a lot of times that moment of commitment is not clearly articulated and that's a big pitfall for a lot of teams. People are like, well, we're talking about it and we're sort of aligned. Um, so being very explicit on the differences, like even articulating and documenting, these are the differences in opinion, but then saying, okay, we've crossed the threshold where we have committed.

And so those differences actually need to go on the back burner and everyone for the function, they represents me to show up fully supporting this decision because one of the things that can be most toxic to a company is when the leadership team can't actually align and agree on a direction.

Todd Jackson: Okay. And how about the board? Because. It's something that a lot of early career PMs don't do, don't think about. And even managers of PMs don't often do, but as the VP of product, you are visible to the board, how do you think about that? What is, what is the role and, and how do you succeed at that? 

Jiaona Zhang: Yeah, I do think it depends on your stage and the relationship that you have with your board. And so here at Webflow, it really is a partnership. And so, you know, to everyone who is on the board, who's an investor, you know, we've made it really clear that we're here to build an infinite company, which means that we'll actually pick, you know, longterm solutions over short term ones.

And so given that context, we have just a very candid relationship with our board. We view them as sounding boards, you know, people who can help. Um, I often give them homework, whether it is recruiting homework or, you know, product strategy, deep dives. But I think that can be pretty unique to our company.

At the end of the day, what I'd recommend is, you know, just understand that relationship and make sure that how you are interacting with the board is consistent with how your CEO and how your peers on the exec team are engaging with the board. I do think it's really important to have a unified front.

And sometimes it's hard to find that line of having that unified front, but yet also leveraging the board to help give advice on hard decisions where there might be disagreement.

Todd Jackson: And so when you reflect back now, JZ your journey to VP of product, what were the most important lessons you learned? And even as an experienced product leader, things that might've surprised you when, when you became. 

Jiaona Zhang: I think the biggest lesson I've learned, it's not that different from the manager lesson, which is, what exactly is your job? your job is not to figure out what to build your job is instead to figure out what the world needs to look like, what the business should look like and what success should look like, and then let your teams feel empowered to figure out exactly how to get there.

 So when it comes to hiring, how does your hiring advice change when recruiting very senior product leaders? 

Jiaona Zhang: you should be looking for candidates who can really bring that strategic thinking and the ability to kind of grow mentor and scale a team. Those are the two big things I need to look for. Um, in terms of how I go about hiring. I actually changed my hiring process quite a bit. We talked a little bit about the questions I asked, you know, for a PM, but for, you know, a leader, um, who is quite.

And owning a whole area at including potentially even a VP. I think it's really important to do something like a 30, 91 80 day plan. It gives the ability for the candidate to really showcase, like what would they do? What kind of initiative would they take? And I also do send them a lot of materials, just, you know, here's a bunch of decks.

You parse them at your own time. You decide what's important. I think even just seeing what people pick out and seeing how they reach out and ask questions with you as part of the process is a huge part of knowing that that person's going to be successful.

Todd Jackson: And then let's flip it around again for the founders. Uh, what are the common mistakes that you see founders make when they hire their first product? 

Jiaona Zhang: So I see a couple of things. The first one is not hiring at the right level that you need for the scale of your company. It's really important in my mind to hire for two years out, essentially, a person who has seen the scale that you will be into years so that when they join, they're not quickly over their skis and not sure how to operate at the same time.

You can't hire too much further than that. If you hire someone who's way too senior, or way more experienced than you actually need, that person is not going to feel utilized, they're gonna get bored, or they will ask for things that is actually not the best thing for your company or something your company is ready for.

And then the last mistake I see is even just the, the traits that founders look for. I see a lot of times people doing one of two things, either they will look for a founder who's essentially going to execute their vision. So, you know, this, this feeling of. build my vision and just make it come true.

Like either someone looking for someone who's really, really strong in execution and not recognizing the importance of strategic thinking or founders who are looking for someone, who's dazzling them with their strategic thinking, finding someone who is, you know, a visionary product leader and thinking that that's what you need when there are times where that actually really makes it harder.

when the founder's vision and that product leader's vision clash, how do you work through the differences? How are you going to find the best solution for your users and the market that you have? And so finding that balance of no, not someone who's just going to execute and also not someone who's just going to pontificate on vision and potentially have a vision that doesn't quite map to yours.

Jiaona Zhang: Finding that balance is really, really.

Todd Jackson: To wrap it up. what is the best piece of career advice you've ever received? 

Jiaona Zhang: It's asked for help. And. Potentially un-intuitive is that, that is Eve like that is increasingly important. The more senior you get and, you know, people might say, Hey, you know, you're more senior. Therefore you have to have all the answers or you should have the answers as opposed to constantly asking for help.

But the more senior you get, the bigger challenges that you're going to be facing. And the answers are very rarely going to be obvious. And so the best way to accelerate again, we talked a lot about learning and optimizing for learning. If you ask for help, you are increasing your rate of learning and just getting those reps in and that's the best way to accelerate your career.

And so I think about that every day, especially now, how do I ask for help as much as I can from Vlad, from my team, from, you know, mentors from, um, the board asking for help is really the best way to get as much input as possible so that you can make the best decision.

Todd Jackson: Well, that's a great place to end it. Thank you so much, JC for spending all this time with us, I really enjoyed it. 

Jiaona Zhang: Absolutely. This was so fun.