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Becky Flint: Bora is a highly regarded product and business executive in Silicon Valley. She has held many roles, from product executive and CPO to support member and angel investor, while working at world-class companies. I had the privilege of working with Bora earlier in my career at PayPal, where she led global expansion, and I learned a lot from her.
I’m so excited to have Bora here to share her journey and the lessons she’s learned from building companies, from growing to scaling, and taking them to multi-billion dollar IPOs. So without further ado, Bora, welcome to the summit!
Bora Chung: Thank you so much, Becky. Thank you for having me. I think you and I overlapped at PayPal when we were both early in our careers. I believe you were a product operations leader, and I was a product manager. It’s great to reconnect after so many years while we’re both pursuing different paths, and I’m happy to share my story with all of you today.
Bora Chung’s Career Journey
Becky Flint: Cool! Let’s take a quick look at your career journey.
Bora Chung: To set the background, I want to introduce myself and tell you a little bit of my career journey. I think this will be a good context for future questions. I guess pictures speak a thousand words, so I couldn’t quite get to the level of making a Tiktok video out of my career, but I did my best to at least get it on a graphic format.
After business school, I joined PayPal, which was my entry into the high-tech world, specifically into Fintech. I started as a summer intern in 2000 when PayPal had just about 100 employees. And I think the famous story is that Elon Musk was the CEO back then. I got a full-time offer in 2001 and became a product manager on the international team, during the early stages of PayPal’s global expansion. Just like Becky said, she learned a lot. She grew a lot professionally and personally at PayPal, so did I. I think this is what happens when you become a part of a rocket ship. I spent nine years at PayPal, where I held multiple roles. One exciting role was leading the Express Checkout product toward the end of my career there. It was the bread and butter of the business. I believe it still is for PayPal.
Then, I joined Apple, where I led payments and financing for all online and offline customer experiences worldwide. I was fascinated by Apple’s innovation and wanted to understand how they achieved it.
When 2014 rolled around, one of my managers at Apple became the first-ever Chief Product Officer of eBay. This was the time when a lot of the Silicon Valley companies were elevating product leaders to C-suite officers. I think they were learning that product was quite important. There was a lot of product-driven growth to be had. So he basically pinged me, and I followed him to eBay during the spin-off of PayPal, which required eBay to build in-house payment capabilities. I also had the opportunity to be the CPO of eBay Korea during an expat assignment in Seoul, Korea, which is my home country.
After returning to the U.S., I joined BILL, a mature startup in 2018, as the CPO. I later became the CxO, which is a bit of a funny title, overseeing product design and customer success. Had a really fantastic four-year run there as an operator.
Bora’s Second Career: Advisory and Investment Roles
Bora Chung: In 2022, I did a lot of reflection after having done product for 20+ years in Silicon Valley. I wanted to become an advisor for the second half of my career so for the last two years, that’s what I have been doing.
My second half career includes a few different roles. I’m on two public boards—Remitly, a fintech company in Seattle, and Krafton, a gaming company based in Korea. I’m not sure if there are any gamers out there in the audience, but PUBG, Battleground, is one of their really popular worldwide well-known game. I’m also advising startups in both Silicon Valley and Korea and working with venture capital funds on due diligence and portfolio companies. My husband and I are also angel investors. One thing I fear in my advisory role is losing touch with current technologies and trends, so angel investing helps me stay connected and maintain that entrepreneurial spirit.
Throughout my career, I’ve always loved product because I always get to work with design and engineering teams to solve problems creatively. You work with definitely a lot of different functions, but designers and engineers are great problem solvers, they approach the problems in a little bit of a different way. I also like the daily activities of the product manager. You usually do multiple things at the same time, but you generally ideate, and then you define, you debate, and really polish your idea. You build things, you launch things, you measure and see what went right, what went wrong, and then you rinse and repeat. So I love that journey. And I love just building teams, working with different functions, and creatively solving problems throughout the journey.
Transitioning from Product Manager to CPO
Becky Flint: What an amazing career, Bora. It’s very interesting. You’ve gone from product manager to product leader, then CPO, and even CxO. What would you say is the key difference between a VP of Product and a CPO?
Bora Chung: The main difference is the scope. As a VP of Product, you’re focusing on optimizing your specific area, such as payments or search capabilities. But as a CPO, you’re responsible for the end-to-end product experience, thinking about global optimization and ensuring the entire journey is aligned across all teams.
When I was a VP, I worked alongside other VPs, each owning a domain like shopping cart, checkout, or seller experience. But as CPO, my peers were leaders from other functions like sales, marketing, and engineering. I was responsible for setting the product strategy and explaining it to all teams.
Additionally, as a CPO I also started to think about, what are some of the teams that I need to have as a CPO to multiply our team? And that’s when I started to think about three sub -functions in product. Product analytics, just to measure how we’re doing. Product operations, a lot of the work that you and your team are doing. And then product strategy. So at a certain scale, and with the responsibility of the chief product officer, I started to think about this core shared functions that are, in my mind, multipliers for the entire team that focus on analytics, operations, as well as strategy.
Managing Product Strategy and Operations
Becky Flint: That is very cool. And in particular, you’re saying the multiplier. I think that’s, a lot of times, definitely heard. I think, like you said, as your VP product, you focus on the areas you’re in. But when you became a CPO, how do you… When you were a VP of product, obviously you have some challenges, right? And then when you become a CPO, what are the different types of challenges? And also how you kind of not really balance. Business changes, right? Sometimes these areas are more important. Sometimes the other areas are important. Being the person in the role, definitely you’ve gone to different shares of structure. So share it with us a little bit more on, when you start to think about product strategy, product operations, and analytics, how does it tie to your need as CPO? And how does it benefit the rest of the organization, like the rest of your domain leaders, for example?
Bora Chung: For sure. I’ll pick on kind of the local optimization versus global optimization point I mentioned earlier, then expand on it. Becky, you remember the annual planning process we had at PayPal, and it got more expensive and complicated as the company grew bigger, right? I think CPO, with the help of product operations team, set the rhythm of the company and of the execution.
I will use an annual planning cycle. I think each of you in the audience, you would have… Sometimes if you work for a bigger company, very much elaborate planning cycle. Maybe, pardon me, for startups, it could be a little bit more nimble, ad hoc, and agile. But anyway, maybe for midsize to bigger companies, there is a cadence of annual planning cycle. So what happens is that there is a company corporate strategy, and usually a financial goal for the next year or so. If you’re a public company, there’s even longer time horizon, and even a firmer bar of goals and strategies, right? And I firmly believe that product strategy has to be well-nested under the corporate strategy. It cannot be one-off or an oddball. And it should also pay attention to the financial goal as well, because a lot of times these days, depending on the nature of the business, product could unlock a lot of the revenue opportunities as well. So if you think about an annual planning cycle, it starts with a great aligned corporate and product strategies. And then there are some areas of demands, right? So what we need to improve, what new ideas we have, what new businesses we need to start, or new features we need to build to win against competition or serve greater customer needs. And then there are some of the resource decisions, right? So, Becky, you remember that, especially at PayPal, when we were growing like Ambuster, the supply and demand was always out of match, out of balance, right?
I think our demand was maybe oversubscribed, over the demand, over the supply, rather, three to four times usually, right? So then I think as a CPO, I think this kind of gets to the core of your question. You have to prioritize and allocate the resource portfolio for the team. At the company level, first understanding what customers need. So I feel that what really is important is having the rhythm of the planning and execution and setting the direction with the great product strategy, and then making sure that each team knows how to work together and aggregate to achieve the goal.
And a lot of that, I think, comes with product operations. I think you and I have talked about multiple metaphors to describe the critical role of the product operations. I said that the CPO and the product operations together set the kind of beat of the execution. It also balances the supply and demand misbalance. It also is kind of an oil for the well-oiled machine. If the speed, this plan of record, the supply and demand understanding is off, I don’t think there is a well-functioning and very, very kind of productive organization. As a CPO, you basically have to solve all of that and really balance based on the priorities.
Balancing Local and Global Optimization
Becky Flint: Right. You mentioned so many important parts. I’d like to dive deeper into that. For example, you talked about global optimization versus local optimization. This is never easy for product managers, whether you’re a product manager or a product VP. Obviously, your area feels like the most important. A lot of times, product managers may feel like they own the experience or their product. So, why is it necessary to do things like annual planning, which can sometimes feel less intuitive? How do you manage that? And how does this apply not only at PayPal but also at other companies you’ve worked for? How do you balance the bigger picture and long-term innovation with the immediate needs?
Bora Chung: I think I’ll bring up some humility and vulnerability here, Becky. When I was a new product leader, I was very focused on fighting for my team’s agenda, fighting for their resources because I was placing too much weight on local optimization. But as I went through my learning journey and growth, I realized there was a paradox. Once I let go of my team’s agenda or personal agenda and zoomed out to think about the bigger picture—what does the customer want? What’s best for the company? What’s the CEO thinking, not just the product leader of a specific domain?—then my perspective shifted. And in a paradoxical way, this helped me become a better product leader. I could balance the needs of my team and the bigger picture.
One of the reasons I was able to become a CPO was because I wasn’t always pushing for my team. Of course, I always supported them and deeply understood what they were doing. But I realized that when I elevated my thinking, when I looked at the larger strategic point of view, it benefited both my team and me. And I hope that makes sense to some of you. I also hope you don’t take as long to learn this as I did. That’s why I always think about local optimization versus global optimization.
Measuring Success as a Product Leader
Becky Flint: Wow, that’s really cool. But I want to dive deeper into that. What you said—when you were a product manager, you focused on your area, and you did a great job at it. But then you weren’t always making it strategic because you were thinking about just one small part, not the business or the customer. When you elevated your perspective, let go of your focus, and opened up to the bigger picture, it helped you grow into the CPO role. That’s such a profound insight. It reminds me of a conversation I had a couple of days ago with another CPO. He said, “You are not your product. I’m not my product. We’re just here to progress and accelerate the company’s goals and customer benefits.” That aligns so much with what you said. It’s really eye-opening. Now, I want to ask: how do you measure success when you’re not focusing just on your domain or area? How do you measure success on the path to becoming a CPO?
Bora Chung: Yeah, for sure. Let me share how I was evaluated along my career journey. When I was an early career PM, I didn’t have to worry too much about the bigger picture. I just focused on mastering my craft as a PM and understanding my area in depth. But as I progressed to roles like director or senior director, I started to hear something important. It wasn’t just about what I delivered, but how I delivered it. That “how” is important in leadership. You could argue that it’s hard to quantify thought leadership or stitching together an end-to-end experience with a KPI. But I believe there are thought leaders who think expansively and beyond the constraints of what’s in front of them. These leaders are rewarded. The natural progression goes from executing well in your area to understanding the whole picture, and eventually to anticipating what’s next. What new technologies will disrupt us or enable us? What competitive forces might unseat us? Or do we need to team up with someone to win more customers? Seeing around the corner is key as you grow into a senior leadership role.
So, I think that’s the progression. In summary, I do believe that sometimes, especially for analytical types, product managers tend to hug their metrics, and everything has to be quantifiable. But there are definitely soft skills involved in leading and influencing the organization, such as anticipating changes and understanding external dynamics like the competitive landscape.
What Makes a Great Product Operations Leader?
Becky Flint: This is super helpful. There are tangible things, but also intangible things. Of course, you need to do the tangible things well—that’s a given. If you don’t do that, you can’t move forward. But it’s not enough, right? It ties into the next step. Going back to your point, you mentioned product operations and product strategy. As a CPO, you need to run your product organization, drive the business, and anticipate what’s coming. So, the fuzzy part of leadership—what differentiates a good product leader from a great one? What’s the difference in product operations? You’ve worked with different product operations leaders across various companies. What differentiates the great ones from the not-so-great ones?
Bora Chung: That’s a tough but important question, Becky. I’ll answer it in two parts. First, communication—super communication—and I’ll elaborate on that. The second is guiding the organization through change management. So, communication and change management are the two things that differentiate great product operations leaders.
Every job description I see for product operations mentions excellent communication, but it needs to be taken to the next level. It’s about leading with the headline first. Whether things are good or there’s a problem, you need to state it clearly. Often, there’s a lot of data and details, but it’s essential to start with the key message. Don’t overwhelm with complicated dashboards or JIRA boards. A great communicator gives the one-sentence synthesis of the situation. Once that’s clear, you can dive into the details.
So I would say super communication, knowing when to level up, knowing when to drill down to the details, knowing when to use science, knowing when to use art of persuasion. I think super communication is, I think what differentiates a really top-notch product operator versus not.
The second differentiator is change management. The only constant in a product organization is change. I think a really capable product operations leader could guide the organization through a lot of changes. What does that mean? It’s anticipating different scenarios, having plan Bs all the time. And then when there’s changes, repeating the key messages, also telling different teams what this change means for you and what needs to start, stop, continue, right? So if you could actually deliver that, and I think you’re nodding vigorously, Becky, this actually is the multiplying force because there’s nothing more stressful in human nature, in team context than change. But if the product operators could help us get through the change, this still stays the same as before, but this got to change. We have made a trade-off decision because of this reason. And now the new plan of record is this. If we could really crystallize this change management, I think a lot of the stress, the noise, the miscommunications, the misdirections will be diminished.
Knowledge Learned During the Journey – Key Takeaways
Becky Flint: That’s great. You mentioned how data is not the same as information. The headline communication is important—it’s about setting the direction clearly, whether it’s good or bad. Then, you mentioned change management. A lot of this comes down to roadmap changes, trade-offs, and priorities. It’s true—product operations leaders who work cross-functionally with domain leaders and the CPO on trade-offs are vital. Effective communication is key to successful product operations, it’s really core part of effective product operations for sure.
You’ve shared so much. I wish we had more time, but I know we’re wrapping up. Before we go, could you summarize the key takeaways and learnings from your career?
Bora Chung: Yes, thank you. In closing, I want to share three takeaways that I’ve learned throughout my career. If I can help accelerate your career and give you tips to avoid mistakes, here they are: Customer empathy, technical chops and kind of commercial sense, right?
Oftentimes people say that you buy a product or software to reduce pain, either reduce pain or bring joy. So you have to have customer empathy and everything you do has to be rooted with customer needs and customer pain points. And oftentimes people get that. So I want to make sure that we always get grounded on customer empathy. And then at the end of the day, we are in the software business. So technical capabilities, especially understanding how we could solve these problems, is keen. A lot of times, we are not in a charity or public sector. So we have to make money. We have to commercialize what we’re building. So having a keen commercial sense is also helpful. So I think these are really hard three qualities to get, but if I have to distill what makes a good product leader and a great product operations leader, I think these are the three. But of the three, I would argue that you should always be grounded and start with the customers.
I talked about this a little bit already. When you go through a P&L of software companies, the three key P&L elements are R&D, right? Research and development. And that’s where a lot of the product design, engineering and kind of technology resources are. And then there’s sales and marketing and there is kind of admin, right? So R&D is usually the most expensive resource. And I talked about how supply is usually one third, one quarter of the demand, right? So then it is upon the CPO and the product operations team and the entire product team to have vigorous, vigilant prioritization so that the most expensive resource is put into the most impactful thing for the customer. So that’s one. And then with all the metaphors that I use for execution, we have to seamlessly do roadmap execution. I feel that the roadmap is like a contract from product to the rest of the company. We commit to do this. And when it changes because of some internal or external reason, we are, I think, obliged to tell the rest of the company that this is gonna be the new plan, right? So these are definitely one of the many critical deliverables. So I want to make sure that if we do product operations well, it means that we actually put the most scarce and most expensive resource in usually software companies into great use. And then the job satisfaction for all of us is gonna be great because of it and thanks to this, right?
And then the last part is around trade-off and change management. Oftentimes, because we’re so busy, we forget to elaborate why we have to change something. And then what still stays the same and what needs to change, right? So if we could lead with really fast and clear, crisp communication, again, changes will not be received as stressfully. It’s definitely hard, but when this is done well, and I think all of you could think about a period or company where this is done really well, the whole team is gonna come along.
They’re gonna be happy. They’re gonna buy in. Even this change could be a little stressful. And then they’re gonna be like, who moved my cheese? But I think they will jump along to make this change happen, right? So just wanted to leave you with these three takeaways and hopefully it was helpful to provoke some of your thinking juices.
Becky Flint: Super helpful, Bora. I learned a lot and I think it’s really helpful for a lot of the folks that are going through various journey in their career, regardless of you’re not yet a product executive or you’re a product executive turning to a CPO and from a CPO into the next level, the investors and the board. I think there are always something and I’m definitely taken away. Hopefully you did take some tidbits and learnings from Bora. And if there’s any questions from the audience, is there a way to find you?
Bora Chung: Yeah, for sure. So I am still learning. So I would love to share and learn from you. So the best way to reach me, if you want to discuss any of the topics that I outlined here is to just find me on LinkedIn. I’m usually pretty good and responsive. Thank you so much, Becky, for having me. It was so much fun to share my journey with all of you. I wish all of you a great professional and personal success.
Becky Flint: Thank you so much. I really appreciate it. Take care, bye.
