Carlos begins by asking Oliver how he broke into product management.
"I mostly fell into product management. When I was young, the thing I was most passionate about was building products. My means to do that was coding, though I never was passionate about coding. Making something out of nothing was a super satisfying feeling. This was my first taste of product."
Oliver’s first project, a social media app, went through Y-combinator back in 2011. Since then, he has held roles as VP of Product and Engineering at Udacity, Co-Founder and CEO at Voyage, and most recently VP of Product at Cruise.
Oliver describes some differences between small and large teams. He says, "There’s a need in a small group of builders to communicate well, get the team excited, and be really focused on problems you are solving." Even though the tactics in which you go about exercising these skills are different at each stage of a product team, the skills tend to be transferable.
"It turns out most of the intuition that’s necessary to do that in a small team transfers rather well to a big team. It's a process of iteration."
Workflows tend to break down as the team grows. Experimenting, making mistakes, and learning lessons helped Oliver learn the tactics needed to be successful.
Product teams at Cruise work with a variety of stakeholders in both software and hardware disciplines.
“The truth is it’s less about the area being more complex or anything like that, and it’s more about scaling your own ability to connect dots. The great PMs (not the good PMs) intuitively understand which dots to connect at any one time. In self driving world, there’s just more dots to connect - you have legal dots, hardware dots, and marketplace dots. What I do expect a PM to be able to do is understand that this person needs to talk to this person and we need to make this happen by this date. As long as they can help each partner team that they work with understand what is necessary to ship a truly great product, then that PM is more than doing their job.”
Carlos asks how Oliver applies user testing to make the experience feel safe for consumers. Oliver says he is a huge believer in assembling a team of PMs that have a strong intuition of what’s necessary.
"I believe it’s critical that you empower your PMs to make decisions that might be unpopular, according to data, and they are strongly attuned to what the needs of their customers are."
He mentions the best PMs know when to push on or change constraints. The complexity involved requires them to make decisions fast.
Carlos asks Oliver to share his take on the future of self-driving cars.
"There’s a big difference between the tens of companies that are testing self-driving cars, and the number of cars that have successfully removed the need for human oversight on those self-driving cars. Cruise is the first in San Francisco that has successfully removed the need for that person in the front seat. That’s a huge leap. This technology really stands on decades of development in robotics, machine learning, sensors, and compute, all to make that simple looking thing of removing a human in the front seat happen."
Oliver says they think about the business like any transportation product and use repeat usage, star ratings, and extremes of the product to guide their roadmap and intuition.
"When I look at my career, one of the things I felt is that I’ve taken companies from $0 all the way to that $100M mark in ARR. That’s a period I really enjoy. That’s effectively something from nothing, and taking it to reasonable scale. The next step going from $100M to $1B ARR is a step I look forward to at Cruise. I think we’ll surprise people by how fast that step occurs here."
"What are some key moments in your life that really helped you take leaps of faith?" Carlos asks.
Oliver tells the story of his first app’s success and how asking for feedback changed his career. Most of the time he thinks a lot of folks talk themselves out of asking.
"If I was to put a point on the moment in my career where a lot of things changed, it was the result of asking someone something."
When Oliver was a teenager, he got to know a bunch of folks in the Mac ecosystem. After completing his first app, he reached out to someone who he knew had experience in software distribution. He thought, "I’m just gonna send him a version of this app. I’m just gonna get his feedback."
That one connection introduced Oliver to a publisher who promoted it.
"That moment really triggered so many subsequent steps for me. I owe a lot to that one person, and that one chance encounter of saying, ‘can you help me take this a little further than I feel like I can currently take it.’"
"The truth is - you can only just ask. If no one replies, it doesn’t matter... who cares. But if they do answer...and it does turn out to be something pretty cool, well, you might have found this game-changing moment in your career." Carlos says, "I think that’s beautiful. And very powerful."
