Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)
Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into:
• How to enable product and ops to work well together
• How to run great product reviews
• How to make good decisions with limited data
• How he uses the jobs-to-be-done framework at Opendoor
• How to stay calm under pressure as a leader
• Wild stories from his time at Uber
• Challenges faced at Opendoor during the pandemic
• Much more
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Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin
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Where to find Brian Tolkin:
• X: https://x.com/briantolkin
• LinkedIn: https://www.linkedin.com/in/briantolkin/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Brian’s background
(02:14) Career beginnings at Uber
(02:49) Transitioning from product operations to product management
(06:47) Product and operations synergy
(10:00) Surge pricing at Uber
(12:18) Scaling challenges, and stories
(15:47) Opendoor and Covid adaptations
(25:38) Product reviews and Jobs to Be Done
(40:30) The challenges of A/B testing
(42:23) Increasing conviction in solutions
(44:33) Leveraging intuition in product decisions
(47:07) Partnering with Zillow
(52:55) Staying calm under pressure
(56:25) Finding the “kernel of truth” in product management
(01:00:21) Failure corner: Early days of Uber Pool
(01:06:11) Lightning round and final thoughts
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Lenny may be an investor in the companies discussed.
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Building Product & Ops at Uber (with Brian Tolkin)
[on Uber’s Early Organizational Structure] “Uber always thought about it as a twin-turbine plane: maybe for a short period of time, you could operate on one engine. But if you want to operate at full efficiency, you need both engines working in tandem and working effectively together.” Brian Tolkin, (@briantolkin)
We’re super excited to be joined by Brian Tolkin, one of Uber’s first ~100 employees who built their “Product Ops” organization and then went on to lead Product Management for UberPOOL and all shared rides on the platform. We dive into the nitty gritty of how Uber built their “twin turbine” engine of decentralized real-world Ops and centralized Tech Product, and how the organization evolved as it scaled. We also cover Brian’s new role at OpenDoor and the tight ops + product coupling they’re building now in real estate.
Sponsors:
Sierra: https://bit.ly/acquiredsierra
Be sure to follow the Acquired Podcast:
Acquired.fm
@AcquiredFM
Links from the Show:
Stanford Venture Capital Club
Ben Evans: The End of the Beginning (video)
Lyft IPO (Acquired)
Pre-Meeting Narrative Example
OpenDoor.com