Today we're talking to Gaurav Chandrashekar, a PM at PayPal with a ton of international experience at places like Spotify and Grab. Gaurav talks about his career journey as a PM, how to make big career decisions, and how to maintain a sense of wellbeing and motivation.
Thanks for joining us, Gaurav! It’s nice to connect. First up, can you tell us more about what you do at PayPal?
Sure! Long story short, I’m currently a PM at PayPal. I work on the banking partnership and payment experience team. I’m responsible for one of the ‘Add Card’ flows in the app, which is where users can link their cards by directly connecting their PayPal account to their bank (e.g. Bank of America, Chase Capital One, and so on).
From a user’s point of view, they’re looking to make a transaction — buying something with PayPal at checkout, making an in-store transaction by scanning with a QR code, or even paying with the cards in their wallet. Our core focus is to make sure nobody drops off when they have an intent to purchase.
Nice! How did you come to be in that role? What was your background, pre-PayPal?
Well, after I graduated I worked at Spotify for awhile. This was back in 2011, when it was still just based in Sweden. I learned from some amazing technologists there about how to build great software. It was really eye-opening, and I realized that you can have this global impact by building fantastic software and focusing a lot on the user experience.
I was really excited about entrepreneurship, so next I joined a startup with a couple of ex-Spotifyers who were focused on visual search. We didn’t achieve product market fit, but we moved to the US, and that was my introduction to North America and to Silicon Valley.
I was an engineer all through this time, and the startup experience taught me a lot. I was excited about technology, and as an engineer was thinking a lot about “okay, how do I build this?” I thought, if you build it, they will come. But I learned the hard way that this isn’t the case, after building things nobody used.
Next I wanted to think more about what problem was actually the right one to be solving. It sounds like an easy question to ask, but it takes a lot of effort and thought to really nail it. (I’ve learned a lot from people who focus on questions like this — folks like Shreyas Doshi and Marty Cagan.)
From there, I wanted to pick a place a little more long term, so I ended up choosing Singapore. It’s nice to be closer to family, and there are some amazing companies in the region. I joined Grab as a PM — it’s like Uber, in this part of the world. And then from there I ended up at PayPal. I love the global atmosphere at PayPal.
Awesome, you’ve lived in a lot of places. That’s a real series of adventures. What was the process like that allowed you to build your career at these different companies? And how did you make the decision to move from one to the next?
Great question. Earlier on, I was evaluating opportunities based on, “is this someone I’d love to work with as a manager, a teammate, a collaborator a colleague? Will this be something I’ll be excited to wake up every day and work on?” It was that simple. I also started thinking, “do I get to explore a different culture, a different country, a different way of life?” So that sense of exploration led me to Sweden, and New York, and Latin America.
And eventually, after building up a little experience, I was also asking myself, “is this is the kind role I can excel in? Is this where I want to spend time and grow my career?” Long term, I want to be somewhere that can demonstrate value as a business, and for customers. That makes it sustainable.
You can also join a startup, which is a little high risk because often you’re still trying to figure out the answers to those questions.
So that’s the framework I was thinking about, at a high level.
Ultimately it comes down to, which location, what stage of company, what kind of manager and culture do you want to be working with? And of course, compensation.
I built a career decision framework for myself, which I’ve shared with some friends and am happy to share here too.
That’s super helpful! So having lived and worked in so many different countries, you must have experienced a bunch of different business cultures, as well as differences company to company. Is there anything you’ve learned from these different business cultures that has been really helpful to you, or made you see things differently?
That’s a great question. I haven’t thought a ton about it, but one thing that stands out is that, having spent a couple of years in Sweden, I love the way they work for three reasons. One, they think about building technology in a long term way. You can see that from the likes of Spotify, iZettle (which is part of PayPal), Klarna, Skype, and so on. They had broadband internet pretty early on, which I think gave them a leg up when it comes to technology innovation.
The second thing is that they have a very good social safety net, so if you take a risk and it doesn’t work out, you’ll have support from the government, to some extent. It gives people more freedom to do whatever they want. They’re not as worried about, “oh no, I have to pay these bills right away, I can’t afford to focus on my creative pursuits.” And that’s a bit of a luxury. Maybe people can’t imagine the value that different systems of government can give you. So I think that’s something really beautiful.
And the third thing is, they really value work-life balance. I think that supports the mindset where they build things for the longer term — it’s not just about rushing to get things out in the next six weeks or for the next quarter. Instead, they’re really thinking through some of the bigger decisions and the impact those will have. So those things were really eye-opening for me in Sweden.
All that said, I find the common elements still remain the same from place to place at different technology companies, working in a very globalized environment. I don’t see very many differences in terms of processes and principles from one company to the next.
Personally, I seem to gel more with cultures that are global. At PayPal we have a pretty global team, that values diversity and inclusion, and I feel at home.
PayPal is such a big organization, how do that manage working as a global team?
Well, first of all, PayPal has been around for more than two decades. I’ve heard that some of the code that Max Levchin wrote 20 years ago still runs in production, which is amazing. What that means, I think, is that the culture has developed to think globally about platforms from the get go. It’s never a question of, “hey, can we launch this in Germany or Spain, immediately?” Instead, we think, “okay, if we do this, how would it impact the US, or Brazil, if we launched it in those countries?” And what’s cool about this is that often these questions come from engineering. They can see the truth in the code, and they know they’ll have to figure out what changes need to be made.
As a PM, it makes me really think on my feet, and think far ahead. The fact that we’ve built the systems over decades to think in this way — by default, thinking globally — allows us to have a big impact.
Some of it is changing, too. I sit in Singapore, and the development centre here was opened eight plus years ago. The team has been growing. In part, it’s an initiative to help make us available in different time zones, and not just focus our efforts in the US (although of course the US is one of our major markets).
But if you think about where we have to go next, where our next billion users will come from, they’re not going to be in the US or even in Europe. So there’s been a lot of focus on rapidly emerging markets, including APAC.
How big is the product team at PayPal?
Good question. PayPal has a slew of product groups, including Crypto, Installments, and Credit, as well as others like BrainTree, IZettle, and Venmo that are also part of the group. I wouldn't be surprised if our core PM community internally is in the hundreds.
Do you find the function really different being part of such a large product team, as opposed to be on a small startup team?
It’s great that bring that up. My early experiences at startups were as an engineer. And I realized that I wanted to learn fundamental principles of product market fit, like, “how do you do user research? How do you synthesize it? What are the right questions to ask? What products should you build?”
And there are two ways you can really learn that. One is by joining a company that maybe seems to have product market fit, but it’s still unclear if it’s sustainable. It could be a startup or scale-up that’s taking off globally.
The other way is to join an established company with proven product market fit, where the question is more about what kinds of enhancements you can make, and what new products you can build on top of the existing ones, with the distribution channels and customers you already have.
Having spent time at scale-ups and now at PayPal, it’s clear to me that the principles of “how to build a product” don’t change. You ask the same questions, it’s just the mechanics of how you translate that into execution that change. The speed you work at changes a little. But the principles remain the same.
Absolutely. You started out as an engineer. Obviously many PMs come from an engineering background, and many don’t. If you were to offer advice to someone starting out, what would you tell them? Should they become an engineer first? How should they think about that question?
Yeah, I get this question a lot, and there a couple of ways I think about it.
One thing I love is the creative aspect of coding. I still do it today, on side projects. Running a small app on the side, or coding something to automate one of your own work processes — it’s great to be able to do, and it’s something I hope to still be doing 10 years from now. It gives me a sense that I can create something with mown two hands.
On the other hand, it’s not something I’d like to do full time. Having made the mistake of building things nobody used, I realized the value of a PM — trying to understand the problem, figure out if there’s business value, figure out what’s feasible and viable.
For me, as much as I love to code and spend time thinking about systems, I also love the value of communication. One of my mentors early on said, “I notice you’re starting to think a lot about some product thinking principles, why don’t you start to take on some fo that work?” In a startup, that’s very easy to do because there’s always more work. So I started doing that.
The technical knowledge really helps. It gives me confidence that I know what I’m talking about. At PayPal I see a lot of people who are technical in nature, which is amazing, because conversations are really effective then. But it’s a double-edged sword. I often find that when I’m talking to engineers, it’s very easy to think about how we’ll build something, and forget about the customer. At some point you have to remove yourself from the equation and say, “hey, look, these are the user problems.”
So I try to keep a little distance — I leave it to the engineers to figure out how they’re going to do it. I can say, “here’s the problem that needs to be solved, but you guys figure it out.”
What are some of the biggest challenges you’re facing in your role right now?
Well, there are a lot of stakeholders at PayPal, and the complexity of getting sign-offs increases when you have a lot of processes in place. This is a function of big organizations, it’s not specific to PayPal. But understanding these processes takes awhile. I’m still relatively new, so it can be hard at times, especially if you have a startup mindset where you want to hustle to get things done. So, working with a long list of stakeholders, I try to focus on breaking things down into Step 1, Step 2, Step 3, and having patience.
The other challenge is my timezone. A lot of our stakeholders are in San Jose, which is great. It keeps me connected to what’s happening in the Mecca of tech, essentially. But it means I have to think ahead a lot. I don’t want to miss a day, so I have to plan, and work hard to keep close stakeholders aligned. I’m always trying to be better at building that working relationship across teams, and across different timezones and regions.
And how do you approach that?
One thing I do is keep a list of all my stakeholders, and I try to figure out what their communication style is. It’s not something they’ll always explicitly tell you, but it’s something you can learn for yourself. Do they respond on Slack? Are they more of an email person? Do they need nudges for you to get a response from them? So it’s just a model that you update as you continue to work with people, but it helps.
On Twitter you talk a lot about your internal approach to work. How do you think about maintaining your motivation, your energy levels, and your work life balance?
I started doodling recently and putting these diagrams up on Twitter, just about whatever I’m thinking about. It’s often to do with motivation, taking care of your mental health, productivity, and so on. It’s not specific to the PM role, but I think wellbeing is so important to take care of. Especially when there’s no differentiation between your work life and your personal life. I feel really privileged to be at a company like PayPal that really values wellbeing. It’s one of our core values. There are a lot of resources available to help you take care of yourself.
The other thing is, your ‘why’ can change. I’m always going back to, “why am I doing this role? Why am I at this company? What am I trying to achieve?”
For me, for instance, the common theme has always been that I really like working with the people I’m working with. Getting on calls energizes me. When I can solve a user problem, learn something new, launch something and start getting feedback, I really enjoy that process.
Great framing! Do you have a favorite app or tool that you’re obsessed with right now?
For me, it’s the Oura ring. It’s amazing. I love the app. I check it first thing every morning. It’s not because they have any new kinds of data. There are lots of fitness trackers out there. What they do really well is that package that content in a useful way. I love the user experience, and how they show you your scores. They also turn them into useful insights. They’ll say, “hey, did you drink alcohol yesterday that maybe affected your sleep?” Or “it seems like you’re sleeping later than usual, why don’t you prioritize your sleep today?” So the user experience, plus using the data to generate insights instead of just showing dashboards — it’s really cool.
I think you’ve convinced me to get one. Last but not least, have you read anything lately that you loved?
I’m reading The Almanack of Naval Ravikant, by Eric Jorgensen. It’s amazing, it’s so succinct. I’ve followed Naval for awhile, but I love having this info in book form because I can read a little and let my mind wander and think about how I can apply it to my life, as opposed to just continuing to scroll on Twitter.