Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)

You've worked at two businesses that have done incredibly well combining product and ops.

Uber always have this mentality, and Opendoor does too, of the product operations twin turbine jet plane where you can, like, fly the plane on one engine for a little bit if you need to, but it's operating most efficiently and effectively if both are working together.

What has having been in ops done to make you a better product leader?

Give a really deep understanding of how the business actually works is a pretty good foundation for them going on to say, "Okay, what do we actually want to build in a more, uh, scalable technology way?"

Something else I've heard that you're very good at is staying very calm under pressure.

I've slept on the floor in China before launching UberPOOL, and, like, when you reflect the stress onto your teams, everybody tenses up. It counterintuitively doesn't produce better outcomes.

(instrumental music) Today my guest is Brian Tolkin. Brian is currently head of product and design at Opendoor. Before that, he spent nearly five years at Uber, where he joined as employee 100 before Uber had UberX or UberPOOL or any kind of shared rides. He actually started on the ops team at Uber, moved into product, ended up leading product and launch of UberPOOL and then taking it global. He also started the product operations function at Uber before that function was really even a thing, which I didn't know until the chat that we had. In our conversation, Brian shares a ton of lessons about building products with a heavy operational component, also how to run great product reviews, how he implements the jobs to be done framework at Opendoor successfully, the story behind Zillow trying to compete with Opendoor, failing, and then partnering instead, plus a ton of great stories from the early days of Uber and Opendoor, and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Brian Tolkin. Brian, thank you so much for being here, and welcome to the podcast.

Thank you. Appreciate it. Thanks for having me.

First of all, just a huge thank you to Keyvan Baigpour for connecting us, introducing us. He said all kinds of amazingly nice things about you. He also gave me some very hard questions to ask you. I hope you've come prepared.

Terrific. Put me in the hot seat.

Okay. I want to spend a bunch of time talking about product and ops. You started your career in operations at Uber. You actually started on the ops team, and you moved into product. You've also worked at both Uber and at Opendoor, which have both huge operational components. I think it's really rare that people, one, see a company scale to the heights of Uber and Opendoor with such a heavy operational component that are still tech companies. And, also, it's really where someone starts in ops and then moves into product and ends up where you are, where you're chief product officer at really successful company. So, I have a bunch of questions here. Maybe the first is just, what has having been in ops done to make you a better product leader? How does that change the way that you operate as a product leader?