“Sweat the Details” and Other Commandments for Mapping Out a Career in Product

“Sweat the Details” and Other Commandments for Mapping Out a Career in Product

Veteran product leader Jiaona Zhang walks us through the biggest lessons from her entire career in product at Dropbox, Airbnb, WeWork and now Webflow, from breaking into the function as a first-time PM to tactical tips for navigating transitions into more senior roles.

The first lesson Jiaona Zhang teaches in her graduate-level product management course at Stanford is embracing problems.

Currently the VP of Product at Webflow, Jiaona Zhang—or JZ as she prefers to be called—has watched early career and senior PMs alike slip into a  “solutioning” mindset too quickly, rather than sitting with the problem at hand. Her observations are collected from the past decade working in product management at companies like Dropbox, Airbnb, and WeWork.

“A lot of times people want to jump straight to a solution,” Zhang says. “‘Wouldn't it be great if we built X or our users could do Y?’ And that is a huge mistake.”

The problem with leap-frogging to a resolution, Zhang says, is that this skips over what she feels is the most important part of the product-building process: understanding the problem for your users and identifying the opportunity for your business.

“In the course that I teach, we go deep into separating the issue from the solution space,” Zhang says. “Most likely, 90% of the time, they’ve jumped ahead. Pulling them back into the problem space and helping them understand how to navigate that is critical.”

As a product leader, Zhang’s flexed her problem-solving chops on products generating millions of dollars in revenue, from popular mobile gaming apps to launching Airbnb Plus, its luxury home marketplace. Longtime readers of the Review might also remember her shrewd advice for building MVPs in the popular article “Don’t Serve Burnt Pizza (and Other Lessons Building Minimum Lovable Products).

In this exclusive interview, Zhang shares candid and thoughtful advice earned from every stage of her career journey, from an early career PM to the executive role she holds now.

She covers everything from how to break into the function for new grads or folks considering a career pivot and some of the most common missteps she sees PMs make in their early careers. As we continue up the ladder, Zhang unpacks the essential skills needed to ace the transition from IC to managing PM, and tactical pointers for Heads of Product when working with a CEO and an executive team.

Whether you are exploring a new career path in product management, a mid-career PM with sights on the executive suite, or are a CEO looking to understand more about the product function at your own startup, Zhang reveals invaluable nuggets of truth as she recalls the most important lessons she’s learned in each stage of her career path.


Just as it's common for many entry-level roles to vary drastically, the day-to-day duties of an early product manager can run the gamut based on the size of the company or the industry. The role of a PM at an early-stage startup might not reflect the same experiences of one at a bigger tech company, for example.

But no matter the size or scope of the product you are working on, Zhang offers up three foundational building blocks for every PM to stand on:

  • Understanding: The first skill is all about deciphering what to build, Zhang says. “You do that by deeply understanding your user’s problems and also really defining what business success looks like in the context of your particular company.”
  • Collaborating: The second (and a huge chunk of what a PM’s day-to-day looks like) is working with a team to build a solution. “As part of that, you are working with a lot of partners to effectively get whatever it is you’ve built to market. There are so many great products out there, but without that go-to-market motion, they aren’t successful.”
  • Iterating: Finally it's closing that loop. Almost no product is perfect the first time around. You must learn to iterate and not be too precious about your ideas. “You have to learn from user feedback, the data you see and use all those inputs to improve your product,” she says.

Zhang breaks down her early career PM playbook into four chapters, sharing step-by-step advice for those starting from the outside as they make their journey into the product function. Along the way, she flags the mistakes she made herself that other folks can sidestep.

Advice for breaking into the function

As many product leaders have shared with us before on The Review, every path into the org looks different.

Zhang herself graduated from Yale with a degree in economics and worked for a few years as a consultant before exploring what doors might open for her in product. At the time, she says she didn’t even know about PMs.

But what she knew for sure was that she wanted to spend her time crafting creative solutions. At every chance she got as a consultant, she would take small steps toward this goal — spending her days researching, putting decks together and making product suggestions to clients.

“I would walk away just hoping the client would implement my recommendation,” Zhang says. “I really wanted to be on the other side of the table where I was building and operating and working with teams directly.”

When Zhang eventually learned about product management and that a career path was out there for folks with a builder’s mindset like herself, she felt rather discouraged.

“It was actually a little bit disheartening at the time, because I learned that to be a product manager for a lot of companies, you know, let's say the Google's out there, you had to have a computer science degree in order to even be considered for an interview,” Zhang says.

The stringent requirements of a tech PM in the early 2010s forced Zhang to think deeply about what environment might be best for her future goals. “I wanted to be somewhere small, and I specifically wanted to be building on mobile, because I believed that was the future.”

Her strong conviction about where the world was going mixed with astute leveraging of her background in analytics was how she landed at Pocket Gems in 2011, a mobile gaming startup, as her first full-time PM gig. The startup was one of the first to experiment with developing games for iOS and Android, and its games have since been downloaded over 325 million times.

Pocket Gems also provided Zhang with the opportunity to own several projects even as an early PM, such as its top revenue-generating game, Tap Paradise Cove, which consistently ranked in the Top 10 grossing list of Apple’s App Store.

“I knew I wasn’t the most technical, not even close,” Zhang says. “But I’ve learned over time that for a PM role you don’t have to be extraordinarily technical to be effective. What I worked really hard on becoming someone who could drive business outcomes by owning the biggest live game and generating the most amount of money.”

For early PMs looking to maximize their business impact, here are three traits to cultivate:

  • Excel at communication. Zhang emphasizes that the best PMs enjoy the details of getting their messages across, and develop precise methods to do so. “The day-to-day of a PM is a lot of communication. You're communicating with your users, you're understanding them, you're communicating with your team, and you're making it really clear to them what success looks like and what you've learned. And then you're communicating with any partners and stakeholders.”
  • Sweat the details. For Zhang, the archetype of a high-impact PM is someone who’s keen to get into the thorny details. This could mean working to optimize existing features or diving into the data to improve a feature set. Essentially, these PMs are meticulous and detail-oriented. “You need to have deep care for your users and for the ultimate product experience. If you don’t sweat the details, it’s so easy for low-quality products to slip through.”
  • Be intensely curious. Zhang compares the job of a PM to that of an editor acting as liaisons between the user experience and the team building for them. Being intensely curious about what your users actually want, figuring out the right solution for them and channeling all of that information into the product is the crux of the PM role. “A lot of times, change won’t happen unless you put it in motion somehow. So the combination of having that really deep curiosity and the proactiveness to go do something about it is really critical."

As for who shouldn’t go into product management? Anyone who wants to call all the shots.

There’s a common saying out there that as a PM, you’re like a mini CEO. I find this very problematic. Yes, you may have the accountability as a CEO, but you have very little authority — oftentimes none at all. So if you want to be a PM just to make decisions and dictate what the team should build, it’s not going to work out.

Common mistakes to sidestep

Drawing from Zhang’s personal experience as PM and her time leading teams at various tech companies, Zhang shares the most common mistakes she sees early PMs make, and how they can be avoided:

Mistake #1: First-time PMs try to prove value in the small wins, not the big picture

Zhang notes the pressure a first-time PM can feel when starting out. You might have a natural inclination to take on quick-win tasks like bug fixes or project management, but Zhang warns that’s a big mistake. “Success in your job is actually building a great product, not just making your team happy or executing on whatever small task crops up.”

Instead, she encourages a mindset of looking both at the big picture and then going many layers down to the details. A PM is ultimately responsible for both, and finding value that drives innovation is the surest way to make an impact on any new team — not just squashing bugs.

Mistake #2: Not learning to say no

Operating in such a cross-functional role, product managers are often asked to take on more than their bandwidth allows. And Zhang sees early career PMs biting off more than they can chew — but developing an intuition on when to say no is an important part of becoming a stronger PM.

“Generally as a human trait, it's very hard to say no,” Zhang says. “But it's so important for the PM to do that. And it's not always intuitive.”

What you’re asked to do is always greater than what you’re able to do. So being able to recognize what’s not worth spending your time on is the essence of good prioritization.

Mistake #3: Not spending time on good communication skills.

Folks can often misconstrue that crisp communication just rolls off the tongue (or the keyboard). But Zhang reiterates that good communication takes practice, even for folks that it appears to come naturally. Coming up with a clear and precise framework for how you tailor your message to a specific audience is the bulk of a PM’s job, and spending the time on your own communication style will pay off.

“How do you tailor your message to an audience? You are going to be speaking to all these different types of people, whether it’s users, your direct team, or leadership. Tailoring your communication and messaging is critical.”

Tactically, Zhang recommends practicing being concise in everything you write. Start with trimming down emails and Slack messages, then work up to bigger presentations. Drilling down your thoughts into shorter, simpler sentences is the bread and butter of what makes a good communicator — and thus, a good product manager.


When Zhang transitioned from Pocket Gems to Dropbox, she also made the leap from IC to manager — introducing a whole new skillset beyond the nuts and bolts of product management.

At this level, it’s no longer enough to be operationally excellent, Zhang says. Through her observations, she sees the most successful leaders master the balance of strategic thinking and motivating their teams.

“The biggest change in this phase is that your impact is measured through your team and not what you do yourself. What got you to where you are is most likely not gonna get you to the next point,” she says.

As a manager, you have a lot less control, but a lot more influence. You are coaching and supporting your team — your influence is now through your reports.

For those looking for advice in navigating this tricky transition, here are her two main takeaways on how to successfully stick the landing from IC to people manager.

Learn to be an emotional dampener

Motivational work is a challenge for managers in any discipline. Taking on emotional labor to boost your team’s morale while also massaging their frustrations is its own unique skillset.  As such, Zhang encourages anyone eyeing the manager’s seat to carefully consider if motivating a team (and all the soft skills that come with it) is something you’d enjoy taking on.

“An important skillset of being a good manager is what I call being an ‘emotional dampener’ for the team,” Zhang says. “An emotional dampener finds themselves in situations where they know their team is upset, they know people are frustrated about a certain problem but choose to coach them and help them by dampening their emotions as opposed to riling them up. If that’s not an easy role for you to take on, you should think twice about being a manager.”

There's a saying that a good manager is often a punching bag and a therapist. It’s important to go into the role with eyes wide open and be aware of all the emotional hats a good manager needs to wear.

Think strategically as you get more senior

Strategy, more often than not, is treated as a bit of a buzzword. Yet, when taken seriously, it is the difference between a successful startup and a failing one. Zhang spends a large section of her product management course teaching students how to think of strategy and how not to. Zhang’s hack to good strategy isn’t an Excel spreadsheet or a cost-benefit analysis comparing all the features in your roadmap. Rather, good strategy is good storytelling.

“People tend to overcomplicate it, but it’s actually quite simple. Strategy is outlining the things you are going to do to get where you need to go,” says Zhang  “I stress a lot around telling human stories. A good strategist should be able to say in 30 seconds what we’re doing for our users.”

As you widen the aperture and help your teams think strategically, Zhang reminds you to tailor your method to your audience.

“If you are working with a first-time PM, you are drawing a narrow box with a thick marker,” she says. “Inside the box, you are explaining the future we want to build. Outside is the goal we’re trying to achieve. As your team gets more senior, you no longer have to tell them, ‘this is exactly what you have to build.’ Instead, explaining strategic decisions turns into ‘I don't know what we’re going to build per se, but this is the outcome that we need to achieve.’”

Jiaona Zhang (“JZ”), VP of Product at Webflow


The final jump Zhang discusses in her career is the leap from manager to executive. Here she shares tactical advice for VPs of Product, Chief Product Officers, or any other roles that sit on the executive team and report directly to a CEO. Founders and CEOs will also find guidance here on how to work collaboratively with their product teams and scale up their impact.

Zhang currently operates as the VP of Product at Webflow, a no-code website builder geared toward designers and marketers. Her responsibilities extend well beyond product management, overseeing product design, research, developer relations and product partnership teams.

As you level up to the executive suite, you leave behind most of the day-to-day duties of a typical PM job description and instead are focused on bigger-picture problems, like org design and collaborating with other company leaders, like marketing, sales and finance.

“At this stage,  you have to get comfortable making hard, potentially unpopular decisions,” Zhang says. “A lot of your job might be saying no to a founder or being able to hold your own on an exec team. That ability to stand your ground when needed and have a strong perspective on not just your own functions, but others across the business is critical to being a good VP.”

Treat your org as a product

In Zhang's view, one of the most essential secret weapons up a VP of Product’s sleeve is to simply treat their team like a product itself, by thinking of your org members as customers — and the processes and tools they might need to be successful.

Build a team in the same way you would build a product. Just as you would think about your users and their pain points, you should think about your team and the problems you’re facing so that you have clarity on what you’re solving for.

What comes of this, is processes that enable people to do their best work—at scale.

To get started with diagnosing some of the pain points your team may be facing, Zhang offers up a few questions to ask yourself:

  • How am I thinking about where my strategy is going?
  • How can I make sure that strategy is designed for the way my organization is laid out?

Tactical pointers for working with the CEO and exec team

As you expand your scope beyond a team of PMs, an executive product leader must work in tandem with several other stakeholders with the ultimate goal of growing the business.

Tips for working with the CEO

Zooming out, the relationship between the CEO and the Head of Product is about complementing each other's skillsets. Product leaders must think about how they can bring out the best in the CEO, aligning out an agreed-upon company vision and then channeling that into a clear product strategy. In essence, the partnership between a CEO and a Head of Product succeeds if they can get the rest of the executive team on board to execute their strategy.

Building a solid relationship will vary based on personality (and the CEO’s own product chops), and of course — every CEO is different. Zhang shares her experience partnering with current Webflow CEO Vlad Magdalin.

“He’s very product-minded, originally an engineer that went to art school,” Zhang says of Magdalin. “My job partnering with him is to pull him out of being in purely solutions mode and instead sit with problems as we work to understand them more deeply. It’s something he can default to naturally given his background.”

Zhang advises when working with a founder or CEO to keep in mind they are used to making the call. Oftentimes they’ve called the shots on what to build from the beginning, because that’s how they built an MVP and got to initial product-market fit. But it’s with the advice, skill and experience of a Head of Product that will take their company to the next step.

Tips for working with the executive team

Any executive team, regardless of how harmonious, will face its fair share of disagreements. But key to moving forward is to make sure these conflicts stay contained, rather than percolating into resentment that derails the business. The antidote, in Zhang’s eyes, is in the relationships you build with each member of the team, and learning to communicate in your own shared language. She illustrates this in her working relationship with the VP of Engineering.

“When I partner with our engineering exec, I take the lead when it comes to why and what we're trying to accomplish,” Zhang says. “But they take the lead on how we would accomplish it, because the engineering team at the end of the day is going to have the most input on if we are going to meet our deadlines, and do that in a scalable way.”

This kind of trust, and ability to lean on each other, is something Zhang says she's seen exec teams flounder with. But as anyone in the C-suite knows, there’s often a loud chorus of differing opinions each time a decision needs to be made. To navigate around this corner, execs must continually practice “disagree and commit” — and document these inflection points clearly.

“A big pitfall for leadership teams is not explicitly articulating or documenting differences in opinion before a decision is made,” Zhang says. “When our team hits a moment where we all disagree on a direction, but a commitment has been made, we point back to our notes where each different opinion has been written down. To move forward, we say ‘we’ve crossed the threshold where we have committed and these differences need to now go on the back burner.”

Everyone that represents a function needs to show up fully supporting leadership’s decision. 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.


For founders who are ready to take the next step for their startup and start scaling their product org, nabbing the right product executive who will execute on their vision while also growing with the company can be one of the trickiest hires.

So how can founders make sure they are choosing the right product executive for their company? And how does hiring a more senior product leader differ from hiring someone earlier on in their career? “Look for candidates who can really bring that strategic thinking and the ability to grow, mentor and scale a team,” Zhang says.

Zhang shares some of the most common mistakes she sees founders stumble over when it comes to building out their product org with a senior hire for the first time to help you get a lay of the land.

Mistake #1: Not hiring for scale

“A common mistake I see founders make is not hiring at the right level that they need for the scale of their company,” Zhang says. “It's really important to plan for what sort of leader you’ll need two years out.”

Zhang recommends looking for someone who understands the scale of the company and can operate what that would look like two years out. “You especially want a person who has seen that scale so that when they join, they’re not getting out over their skis and unsure how to operate,” she says.

Mistake #2: Hiring someone too senior

“At the same time, you can’t hire someone with skillsets you’ll too much further than the two-year time frame. If you onboard someone who is way too senior or has more experience than you actually need, that person is not going to feel utilized in the right way,” Zhang says.

She reiterates that it's not unexpected for senior product leaders in these scenarios to get bored or start asking for things that the company is not ready for, which ultimately can harm the best interest of the company.

Mistake #3: Hiring for the wrong traits.

The last mistake Zhang sees is around the traits that founders deem as valuable in a product hire. She groups these mishires into two main buckets.

“People will either do one of two things. Either they will look for a ‘founder-type' who is essentially just going to execute their vision and make it come true. This person is usually really strong in execution but doesn’t recognize the points of strategic thinking,” Zhang says.

“Or it’s the opposite, where a founder is looking for someone that dazzles them with their strategic thinking or someone that’s a visionary product leader, but isn’t thinking about how their founder vision and the product vision might clash later on.”

To help swerve around these mistakes, Zhang shares two tactical tips for how to discover product leaders that stand out during the interview process:

  • Ask for 30/90/180-day plan. “Especially when hiring for a leader that will be overseeing an entire area of the company, It’s really important to ask for a 30/90/180-day plan. It gives the ability for the candidate to showcase what they would do and what kind of initiative they would take.”
  • Send materials. “I like to send candidates product strategy decks and ask them to parse them independently and decide what’s important. Even just seeing what people pick out or if they reach out to you with questions as part of that process is a huge part of knowing if that person is going to be successful long term.”


It’s common for folks in any function to aspire to move through the ranks, looking at the upper levels of the career ladders with tunnel vision. With that mindset, when seeking out advice or mentorship, it’s not uncommon to go straight to the leaders at the very top of the org chart — like a new grad PM looking for guidance from their company's Head of Product. But one of the most helpful things Zhang said she practiced throughout her career was continually asking for help and seeking the advice of senior managers only one rung above her.

“Find someone who is only a little bit ahead of you,” Zhang says. “Understand what they’ve mastered recently to be successful as opposed to someone you want to be in five years or ten years from now. These people can become your advocates and are better positioned to help answer your questions and open up their network to you.”

And if there is one final piece of advice Zhang could leave with any aspiring product leader it is this: you don’t have to be good at everything. But become exceptional at something.

“The reason why it's so important to be exceptional at one thing is that people will come to you with more opportunities because they know that you’re phenomenal at a particular thing, and that's how you get more responsibility. That's how you have more impact.”

Cover image by Getty Images / JGI / Jamie Grill