Lenny Rachitsky: uncertainty

Transcript context

…I just remember we were working on a project called next-gen checkout. It was the next generation checkout, and I was about to go on maternity leave. My son was going to be born, it was my first child, and we kicked off the project. And then right after that, I went on leave. I came back, I actually handed my team over to my colleague who was a friend of mine and he was my successor, Mike Woo, and he took over the team and he was doing a great job and I didn't want to displace him so I went to corporate strategy. I worked with Rajeev who was the CEO of PayPal at the time and did strategy for him. And then eventually, I started the charity and social commerce verticals at PayPal. I was in the verticals job for a while, then I ended up going to eBay. And when I got to eBay, I led the end-to-end buyer experience, including next-gen checkout. And they were still working on it. Actually, and we celebrated. We actually had drinks on the lawn of eBay, and we celebrated when the project was done and my son had just turned two. You think about that, we did the first integration between the two sites. We actually planned it, my team and the team at eBay between the announcement of the integration, which was July, and we shipped it on October when the deal was cleared. We actually, we weren't even allowed to talk to each other for a long time because the deal was actually a due diligence, so we actually only did the integration in a very short period of time. You think about the next gen of that checkout took two years. And then after that we shipped that product and it was successful. And then they said, "Okay, we're kicking off unified checkout. We're going to integrate the checkouts even more." We looked at the roadmap and it was going to be another two years. At that point, I said, "I can't do this again." I ended up leaving to go to Facebook at that point. But what I learned from that experience was that it wasn't for lack of trying or care. It wasn't that the teams weren't working hard. On both sides, the team was eagerly eager to work on it from both PayPal and eBay, but each individual team had insufficient information and support to actually get it done. And that was the big issue. And yet, there was a lot of misunderstandings in between. It was like, "Well, they're not supporting us, they're not picking our features." But actually, I was literally at both sides of the project and that was not really what was happening. What was happening was there was insufficient support on both sides. And so thus, you end up in a case where you end up fighting over prioritization, and in the end, when you're starving, what you're focused on is what you need to get done on your side. And so really I think instead you either fund something like that, fully get it done quickly, or when you elongate it like this where things are just, you're just creating hostility between the teams. It's so cool that you were on both sides of this experience and saw how very different teams and approaches worked. Something that I don't know if people know is that you joined PayPal when you were very young and it was maybe your first PM role and you ended up taking on some significant responsibility super quickly. I'd love to hear a bit about that part of your career and how you were able to take on such a big role so quickly and how you scaled and learned as you went. I had come to the table at the career fair, and I saw Tim Wenzel who had put together a lot of the PayPal Mafia. He was the recruiter. He is one of the first recruiters at PayPal. I think he might be the first recruiter at PayPal. And then Katherine Woo, she's the head of airbnb.org today. She was a year ahead of me at Stanford and he said, "Hey, we have jobs in marketing and product, which do you prefer?" I look at Catherine since she was, I kind of knew her. I said, "What do you do?" She said, "I'm in product." I'm like, "That sounds good." I have no idea what a product manager did. I mean, at the time it was just not a thing. It was not the thing it is today. And so thus, I ended up interviewing for product. As I was interviewing, they would say, "What would you build?" I had all these ideas. As an eBay seller, I had many things I wished PayPal did, and so I would describe all these ideas, all those things I wanted to do. And then I started the job and I went to the VP of product and I said, "What is the actual job of being product manager? I have no idea." I realized that I had taken a job, I had no idea what it entails. And she actually very patiently isolated, my manager, Dave Lee also did, and just really mentored me and showed me the ropes. Being a new product manager and having no idea what your job is, I was able to really look at the product from a very customer-centric way. A lot of PayPal employees were not eBay sellers. In fact, some in the company were hostile towards eBay. Whereas I said, "This is the best opportunity. You have this marketplace of sellers who have their own websites. If we could just get them all on board, this is a massive win for both companies." And so I looked at it from a very different perspective, and I think that it gave me this ability to see the world from a customer perspective, but also from a product lens. Turns out that I'm a very natural product manager, but I think if you had asked me at the start, I just had no idea what it entailed.…

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