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A podcast Series With Chet Kapoor

Season 2 · Episode 4

What you Don’t Know Helps you Grow: Life-Long Learning with PayPal’s EVP & CTO

Sri Shivananda, EVP and CTO of PayPal, discusses how having a shared purpose leads to aligned execution across teams. He talks about the three things that help bridge the skills gap, and urges us to always seek new knowledge.


Published April 6th, 2021  |  22:37 Runtime

Episode Guest

Sri Shivananda

Sri Shivananda

EVP & CTO at PayPal

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Episode Transcript

Narrator: Inspired Execution is a podcast featuring tech leaders from some of the world's largest enterprises and fastest growing startups. Hosted by DataStax chairman and CEO, Chet Kapoor, each episode follows a leader's journey to scaling a massive business while inspiring their teams. Join us to learn about the experiences that have shaped them, challenges they've overcome, and the advice they'd give to their younger selves.

Narrator: Sri Shivananda, EVP and CTO of PayPal is a computing enthusiast with a passion for innovating on technologies and building effective teams. In this episode, Sri tells us the simple question that sparked his interest in technology and how it led him to where he is today. You'll learn about his lifelong commitment to learning, how a shared purpose drives aligned execution at PayPal, and the important roles tech and culture play in bridging the skills gap.

Chet: Sri, really excited to connect with you today. Thank you very much for joining the podcast.

Sri: Chet, thanks for having me on the podcast.

Chet: So you've been at PayPal for over five years and before that with eBay for 13 years. Tell us about your journey and how you got here.

Sri: The journey actually starts a lot before my time at eBay and PayPal. As a teenager, I went to a high school which was filled with other students whose parents were all in the armed forces. And my ambition was to go into the armed forces and be a pilot in the Indian Air Force. I gave it a few attempts and then eventually, whether destiny or luck or whatever had it, I went to college to pursue engineering.

Sri: And when I was pursuing engineering, I got very interested in computers. It came from a choice that I made. My father came to me and he offered me one of two choices. He said, "You can either buy a motorcycle like all your buddies are buying or there's this thing– they're selling a computer at work for people to have at home and I can get you that." It didn't take me a lot of thought. I decided and I actually got a computer. And that actually started my passion for computing. First, in terms of just learning everything there was to learn with programming. Keep in mind, this is early '90s, a desktop with an 8086 chip and one floppy drive with 360 KB in it. You put a boot disk first, you remove it, you put a programming disk. If you mess with memory, everything comes crashing down and you start from scratch.

Sri: And at the same time what I realized is computing actually started a little bit of a hobby network on the side where I had a social circle, but I also had a hobby circle. What I eventually realized is for an hour of computer time, I could get a full day of motorcycle time from anybody. So in some ways it turned out to be a win-win. That's how I got into computing.

Sri: But long story short, I came to the US in '96, did my master's here, moved up to Detroit, Michigan, and worked for Ford Motor Company. For somebody who comes from Hyderabad and tropical weather, Michigan is a little too cold. So we over-corrected, we moved to Austin, Texas. Worked in Austin, Texas, for a few years for a small company that was eventually bought by eBay in December of 2000. Became a part of eBay at that time. In 2002, moved to the Bay Area, worked for eBay all the way up to June of '15. And in June of '15, with the split between eBay and PayPal, I came over to the PayPal side to learn about payments, learn a new area, to demonstrate to myself that I didn't just grow at a company because I was nurtured in a certain way and I can do it elsewhere too. And it's been an outstanding five years so far at PayPal.

Chet: I'm going to come back to the air force pilot part later on, but what came easy? And then what was hard?

Sri: I think what came easy was a passion and a sense of purpose, curiosity, eagerness, and wanting to learn more and more. Everything else somewhat came hard. I was not very ambitious in my 20s. Came from a somewhat negative situation actually. When the company was closing down in Austin, Texas, and I applied to roles at eBay in the San Jose office, the first five roles didn't actually work out. And I eventually had to take a role that was a bit smaller than where I was at that time in my career. But that trigger point changed something in me. There was this need to prove to myself and at that time to others as well, that I could do something, I was worth something. And I would say that was probably the beginning of my ambition. It was not a great experience at that time, but if you ask me now, I'm so glad it happened because that was like a catapult.

Sri: And I've been in various such situations over time. I feel like each year stretches me as a person, stretches me as a professional, whether it's in the area of technology or in terms of people leadership or in terms of business acumen or other areas. I think when you look around, there is an opportunity to take risks, there's an opportunity to learn and grow, and there is no concept of arrival. You'll agree with me that particularly as we gain more experience in age, we have a tendency to start to realize that huh, well, I don't know as much as I thought I knew and there's so much more to know. You feel less knowledgeable each year you grow, but that becomes a fire, that becomes a compelling force to learn. I'm very thankful to all of the opportunities that stretch me in that way and challenged me, which is the reason why I do what I do today. And I see a trajectory for a lot more of that learning going forward.

Chet: Totally agree with you. In the early parts of one's career, the beginner's mind is an intellectual thing. You think about it, you want it, but you don't want it as bad. And then as your career progresses, what lands up happening is you fail, you're humbled by life itself across all aspects of your life. And the second thing you realize is you meet other people who are really good in what they do and you're like, "Oh my god, I have so much better to do in what I do." And so that combination gets you to say, "Always be in a beginner's mind and drive really hard to learn and to hopefully inspire like you have never done before, the best version of yourself."

Sri: You made a great point there, Chet, which is the inspiration that comes through plain observation of your surroundings and other people around you is huge. And if you have the capability to observe, learn and aspire to be a better self each day, there's no end, you just keep going.

Chet: PayPal supports four billion payment transactions per quarter, and last quarter 100 currencies serving more than 361 million accounts across 200 markets. And I'm sure the numbers are different this month than they were last month, but that's a massive scale. How do you motivate your global teams to execute thoughtfully with speed?

Sri: When we look at ourselves as a company, we are a purpose-led company. And I think our purpose does the magic. There is no doubt we are a significant part of the economy around the globe in terms of the rails that we provide for commerce to occur. E-commerce and payments, particularly in the digitized sense, have made the world a smaller place. It's eliminated physical distance. Anyone today can actually reach out and aspire for anything that's on an unlimited shelf of goods– that's available around the world and that can get shipped to you and you can pay for it digitally fairly easily. Now, while that is the commercial aspect of what we provide, our main mission is to democratize financial services to include people who have been excluded in the past, either because the financial systems that we have around us have been too hard to get to or too expensive.

Sri: Our CEO, Dan Schulman, leads with this purpose and leads with customer championship and that's a tone that he sets all across the company. In doing so, what we desire is to go to those 1.8 billion people who are excluded from the current financial system and to participate in safe, secure, convenient, and cheap ways of moving and managing money that would actually give them more opportunity. Now, when you lead with purpose, agnostic of what you do every day, whether it's a project or initiative or using a technology and so on, those are just means to an end. The end actually is the difference you're making in the world. And when you see signals from your business in the growth that you're seeing, that inspires you. The purpose inspires you no doubt, but progress inspires even more. And as we make progress every day, most of us spring out of bed to come to work to do more towards the purpose.

Chet: I like that. And I think it actually cuts across all functions, and that's the interesting part. So everybody seems to be working at the same cadence and doing it thoughtfully.

Sri: Exactly. Aligned execution is so important. And the alignment when you have a cross-functional organization where you have designers, engineers, product managers, product marketers, finance people, compliance people, risk people, and so on– it has to be something that's beyond your function, beyond your day-to-day. It has to be centered externally on the customer. And that's exactly what we have is that purpose that inspires execution.

Chet: The pandemic has definitely accelerated the adoption of payments in e-commerce. You can see it in the results of all these different companies. Did you have to adjust your strategy significantly? Were there technical challenges you had to face or were there people challenges you had to face? How has the pandemic affected what you are driving for as part of the bigger purpose?

Sri: All of it, Chet. And let me actually start with our most important constituency, which is our employees. The pandemic caused us to make a very quick and swift decision in March to say, "We're all going to work from home." The whole world did. And while we are a digitally native company, we still had to make some more adjustments to make sure everyone was safe, healthy, secure, and productive when working from home. Imagine going from 57 offices around the world to 35,000 offices around the world. How do you still collaborate as a team? How do you actually make sure your values of inclusion, innovation, collaboration, wellness are upheld?

Sri: All of that was our first priority: to make sure that our employees are served well in all the things that they want to do both in terms of engagement and in terms of thriving and creating value. Of course, in the meantime, we're a big utility on the internet. We need to make sure that we are serving all our customers. Suddenly, everyone staying home is participating in more digital commerce. That means the security of the service we provide, the stability of the service we provide, the scalability of service we provide are all extremely important. These merchants who don't have any other avenue to sell anymore are now counting on us to be the avenue through which they sell and make their living as well.

Sri: And at the same time, this was not just about being on the defense. There was a set of conversations we had internally around like, "Okay, we are seeing these trends, what are the things that we can do?" And we started to figure out strategies and initiatives to execute. And as you know from very recent launches that we have done innovations like QR code and the release of that, things related to making sure that we scale to the volumes. For example, Cyber Friday and Cyber Monday are the biggest days in the year. Last year’s was the biggest so far. But now this year, you've seen many days that match that volume. And we're seeing a new trajectory and acceleration in digital payments. Scaling to that was extremely critical as well.

Sri: So much more, whether it is in terms of engaging with the community and doing more in terms of digital kindness, engaging with the community internally and actually addressing the right kind of coping, compassion, camaraderie and so on. It has been a very interesting seven months so far on behalf of the customer, on behalf of the employee– both in terms of the things that we needed to do to cope, sustain, and thrive, but also in terms of going on the offensive and accelerating strategies that were desired in the market.

Chet: Fahim said the same thing, it's like Black Friday every day. And he's from Home Depot so it was really interesting to get that perspective, which is that it's gone up. We used to prepare for one day a year, and now it's nearly happening every day. Thank you. That was great.

Chet: We all know there's a skills gap. You're a strong believer in open source. And you and I have talked a bunch about how open source works and the economies of scale and things like that. Any tips and tricks you may have for our audience on how do you get over the skill gap? Because there are not enough people out there in any facet or any skill-set that gets us to where we want to go. How do you think about it? How do you address it within PayPal?

Sri: I think it's a very broad question. And let me see if I can address it from multiple perspectives. One is, like you said, you have to make choices to build where it's your core. You have to make choices to buy where it's more of the context. And there is an in-between in terms of a great community of developers that are building open source alternatives that are extremely strong, compelling, and that you can both leverage and provide inputs into. So I think in terms of making sure that the technology stack you're building is leveraging from all sources of innovation, that's the smart thing to do.

Sri: Second is, we focus a lot in terms of our internal employees and their development. Chet, we have seen three million minutes of online training that our employees have consumed this year so far. The pandemic has definitely played a role in it, all kinds of different things, whether it is our subscription to Udemy or LinkedIn Learning or whatever the online channels may be– three million minutes for the first time. And this is substituting all the classroom stuff that we did before. So growing people internally, giving them the opportunities, giving them avenues to learn, upskill, and so on is one of the ways you address the skill gap.

Sri: Number three is the process of sourcing, hiring, and onboarding people. It is smart to say that the talent that we desire is all across the globe. And being a global company, how do we subscribe to all of that talent wherever it is? Have a global talent strategy. And in doing so, create an amazing interviewing and onboarding experience for them. As they come in, shower them with the right kind of narratives on our value system, the mission we are on, and the exciting things that we are doing in innovation. And then helping them get to their first success and allowing them to thrive over time. That is what makes us talent-minded. Modern tech, amazing culture and great hiring and onboarding. All of those are different ways in which you can help bridge the talent gap. It continues to be a challenge, but I think there are a lot of great people out there and PayPal is an amazing place for them to be.

Chet: So on the personal side, you've dedicated a lot of time for mentoring and giving back to the next generation of leaders. What advice would you give to a younger version of yourself?

Sri: I think the biggest advice I'd give is to figure out how to cultivate confidence. A lot of that actually comes from smart risk-taking. I have often found that growth I've had has come from me running to things that other people are running from. I'm not asking people to take random risks; I'm asking them to take smart risks. And these are fully knowing that something is a little out of reach and it will stretch you. It'll make you learn new things, new skills, new competencies, new behaviors, new methods, help you build new networks and so on. And if you can take a little bit of risk, you succeed at it, your appetite for more risk comes up. You take that, you succeed, your appetite becomes a little more. Sometimes it doesn't work, but you don't start from scratch. You just start from the previous place you were at. And if you can make that a continuous approach with the right kind of micro-ambitions, the sky's the limit, you can do anything you set your mind to.

Chet: There's a lot of studies that a lot of people have done Sri, which is, is there a direct correlation to success? And you can take any definition of success you want. And the one thing that people have found through every study that they've done is that it is not the school, it is not the upbringing–I'm sure all of those are contributing factors–but what matters the most is risks. I like the way you put it, which is “smart risks,” because no matter how smart you are, there will be some bad decisions you make. And recovering from them and getting back on the horse, if I can say that, and doing it again and again and again, but making it a theme is phenomenal advice.

Sri: You're right. I think you summed it up well: the chances you take, the choices you make, and then of course, grit. That's a great summary. Thanks.

Chet: Who inspires you?

Sri: A lot of people inspire me. Like I told you before, I'm somebody who learns from observation. And I actually get inspiration from many people. Of course, there are big names, including historical ones and even current ones that, of course, inspire you. Books inspire me a lot in terms of concepts. But there are days where I get inspiration from my peers on the C-staff, including my boss, who is the CEO. But there are days where I'm sitting in a conversation with engineers and there is this very early career individual who spins out an idea and I go like, "Wow, that is really cool." And that's the reason I say it's not any specific profile or specific individual. I think I look for inspiration in small things surrounding me. And I feel like I have a 360-degree approach to inspiration, if you will, for myself.

Chet: How do you make sure that while you have 7,000 things to do helping run PayPal, how do you make sure that you're present and observing while you're driving and executing?

Sri: I actually think that a core aspect of leadership is connecting. And for connecting, presence and warmth are the most important ingredients. If you're in a conversation, but you're distracted–you're looking at your phone or you're looking away, or you're thinking of something in your head–that is the worst put-off you can have. That individual will not want to interact with you ever again.

Sri: Leadership happens in daily moments. And someday when a crisis strikes, the reason people will actually come along and want to help in that situation is because of the investments that you made over the years with them in every single interaction. So I pay a lot of attention to each interaction and making sure that I'm fully present in those. And if that means that I have to work harder at other times when I'm not in the middle of interaction, in terms of thought time or decision time and so on, that's what I do.

Sri: And I'm actually extremely surgical in time management. I believe in the concept of habits, rhythms, and rituals. And I use that to create the right kind of sandboxing of what is a must-have, but what's also a need-to-have... Both in terms of execution, outcomes, and strategies, on the one hand (the what), but also in terms of customers, employees, and my network, which is the who. I feel both are extremely important. But give it full attention no matter what you're doing.

Chet: That is awesome. I just absolutely love that. It is about warmth and presence. That was great. Sri, this has been awesome. We really appreciate your time. And I'm sure all our listeners are going to really appreciate your perspective on being purpose-driven with PayPal and your advice that you follow, which is being present and warm being cornerstones of leadership. Thank you so much.

Sri: Chet, thanks for having me. I enjoyed the conversation.

Chet: Thank you.

Narrator: Growth is a lifelong process. We should always seek new knowledge, draw inspiration from the people around us, and take risks to build confidence. Sri also reminds us about the power of purpose-driven leadership and how it motivates teams to execute thoughtfully with speed. In his words, purpose does the magic.

Narrator: Thank you so much for tuning in to today's episode of the Inspired Execution podcast, hosted by Chairman and CEO of DataStax, Chet Kapoor. We have many more guests and amazing stories to come, so stay tuned. If you haven't already done so, subscribe to the series to be notified when a new episode is released. And for Apple Podcasts listeners, please rate and review the show to help give it a wider reach to listeners such as yourself and feel free to drop us any questions or feedback at