All Segments
Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)
39 segments available
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 — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application: https://www.pendo.io/lenny • Explo—Embed customer-facing analytics in your product: https://explo.co/lenny • Attio—The powerful, flexible CRM for fast-growing startups: https://attio.com/lenny Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin Where to find Brian Tolkin: • X: https://x.com/briantolkin • LinkedIn: https://www.linkedin.com/in/briantolkin/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Segments Timeline
The Twin Turbine Jet Plane of Product and Ops
Brian Tolkin discusses the synergy between product and operations at Uber and Opendoor, likening it to a twin turbine jet plane that operates most efficiently when both engines are working together. He emphasizes how his experience in operations has shaped his approach as a product leader, providing a deep understanding of business mechanics and customer interactions.
"you've worked at two businesses that have done incredibly well combining product and Ops Uber always have this mentality and Open Door does to of the product opertions twin turbine jet plane where you..."
Staying Calm Under Pressure
Brian shares his philosophy on maintaining composure in high-pressure situations, recounting a personal experience of sleeping on the floor in China before launching UberPool. He explains how reflecting stress onto teams can lead to negative outcomes, highlighting the importance of calm leadership.
"what has having been an Ops done to make you a better product leader gave a really deep understanding of how the business actually works it's a pretty good foundation for them going on to say okay wha..."
From Operations to Product Leadership
In this segment, Brian reflects on his journey from starting in operations at Uber to becoming a product leader. He discusses the unique perspective gained from working closely with operations and how it informs his decision-making and product development strategies.
"slept on the floor in China before launching lpool and like when you reflect the stress onto your teams everybody tenses up it counterintuitively doesn't produce better outcomes today my guest is Bria..."
Building Products with Operational Insight
Brian explains how his operational background provides a solid foundation for building products that require a heavy operational component. He emphasizes the importance of understanding customer needs and the day-to-day realities of the business to create scalable technology solutions.
"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 ..."
The Birth of Product Operations
Brian discusses the inception of the product operations function at Uber, aimed at bridging the gap between centralized product teams and globally distributed operations teams. He highlights the importance of a strong feedback loop to enhance product development and market adaptation.
"open door and so much more if you enjoy this podcast don't forget to subscribe and followed in your favorite podcasting app or YouTube it's the best way to avoid missing future episodes and it helps t..."
Surge Pricing: A Manual Approach
In this segment, Brian shares insights into the early days of surge pricing at Uber, explaining how it was initially managed by local General Managers. He discusses the balance between local knowledge and algorithmic pricing, illustrating the challenges of implementing dynamic pricing in real-time.
"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..."
Wild Stories from Uber's Early Days
Brian recounts a humorous story about the naming of UberX, which started as a placeholder name. He reflects on the rapid pace of innovation at Uber and how sometimes temporary solutions become permanent fixtures in the product lineup.
"you a better product leader how does that change the way you operate as product leader starting on the operation side gave a really deep understanding of like how the business actually works right you..."
Launching Uber Pool in China
Brian shares a gripping story about the launch of Uber Pool in China, detailing the challenges faced just hours before going live. He describes the intense pressure of ensuring the matching algorithm worked correctly and the late-night efforts to resolve issues before the launch.
"to the customer actually is a is a pretty good foundation for them going on to say okay what do we actually want to build in a more um scalable Technology Way this episode is brought to you by pendo t..."
The Birth of UberX
Brian Tolkin shares the amusing origin story of UberX, which started as a placeholder name during the rapid development of the product. He recounts the intense experience of launching UberPool in China, highlighting the challenges faced just hours before going live, including a malfunctioning matching algorithm. This segment illustrates the high-pressure environment of launching new products and the unexpected joys that come from stressful moments.
"hybrids and had had a bunch of different uh potential names I was not U personally driving this this was someone else on the operations team but they built the model for what this product could be and..."
Adapting to COVID-19 at Opendoor
Tolkin discusses the significant challenges Opendoor faced during the onset of the COVID-19 pandemic, particularly the need to halt home buying due to safety concerns. He reflects on the stress of the situation and how the team adapted by virtualizing the home buying process. This segment emphasizes the importance of flexibility and innovation in response to unforeseen circumstances.
"it was we launched it was great we monitored everything was good and then we walked out um for breakfast at like 7:30 in the morning everyone sleep dead no no one slept all night and we got this um th..."
What is Opendoor?
In this segment, Brian Tolkin provides a concise overview of Opendoor's business model, explaining how the platform simplifies the process of buying and selling real estate. He highlights the core offering of making all-cash offers to sellers, aiming to provide certainty and ease in a traditionally stressful process. This explanation is crucial for understanding Opendoor's value proposition in the real estate market.
"the moment uh where where it feels very very difficult just since you mentioned open door I think many people have heard of open door maybe just give a quick explanation of what Open Door does for peo..."
Synergy Between Product and Operations
Tolkin shares insights on fostering collaboration between product and operations teams, emphasizing mutual respect and understanding of each function's strengths. He discusses the importance of intentional resource allocation, especially in early-stage companies, and how technology can help scale operations effectively. This segment provides valuable lessons for leaders looking to integrate product and operations in their organizations.
"there's no uh no hassle sounds sounds amazing I want that um coming back to Ops and product just to kind of close This Thread uh again you've worked at two businesses that have done incredibly well co..."
Scaling Operations at Uber
Brian Tolkin illustrates the evolution of Uber's onboarding process for drivers, detailing how it transitioned from in-person sessions to automated systems as the company scaled. He explains the challenges faced during this transition and the importance of leveraging technology to improve efficiency. This segment highlights the necessity of adapting operational strategies as businesses grow.
"time as the business needs let's actually spend more time there you keep saying things that I want to that make me want to dig deeper so at Airbnb we went through the same thing where there there's al..."
The Role of Operations in Efficiency
In this segment, Tolkin discusses the perception of operations as a sign of inefficiency and the goal of streamlining processes through technology. He emphasizes the importance of freeing up operational teams to tackle new challenges and innovate. This perspective is crucial for understanding how to balance operational needs with product development in fast-growing companies.
"that a previous podcast guest shared in a newsletter post Casey winers he talked about that operations is usually and this is kind of it's a hot take that operations is a sign of inefficiency and over..."
Effective Product Reviews
Brian Tolkin shares his approach to conducting effective product reviews, emphasizing the importance of creating a supportive environment that encourages improvement rather than fear. He outlines the dual goals of accountability and enhancing product quality, providing insights into how to foster constructive discussions during reviews. This segment is essential for leaders aiming to cultivate a positive culture around product development.
"completely different direction good uh I hear you're very good at product reviews okay a few people few people told me this I'm curious how you set up a product review and any things you've learned an..."
Creating a Safe Review Culture
Tolkin explains how to foster a culture in product reviews that avoids the 'firing squad' mentality. He emphasizes the importance of context and collaboration, encouraging leaders to engage with their teams in a way that values their insights and promotes a constructive dialogue.
"specifically to make it not feel like a firing squad like you're coming in here to be attacked and criticized is there you said context at the beginning of the meeting is this just a part of the cultu..."
The Power of Small Teams
In this segment, Tolkin discusses the dynamics of product review meetings, advocating for smaller groups to facilitate better conversations. He highlights the significance of documentation and how it aids onboarding and understanding of product development within the team.
"I need to do this so he has a whole set of hashtags that communicate how important this is to him from hash FYI to uh to suggestion to uh plea yes pleading you yeah this was actually explained to me I..."
Implementing Jobs to Be Done
Brian Tolkin dives into the Jobs to Be Done framework, explaining its application at Opendoor. He emphasizes the importance of empathy and understanding customer perspectives, particularly in the context of real estate, where transactions are infrequent and complex.
"cing cycling through on a corly basis this episode is brought to you by ATO a radically new type of CRM there's a world where your CRM is powerful easily configured and deeply intuitive ATO makes that..."
Framework Flexibility
Tolkin discusses the need for flexibility in applying frameworks like Jobs to Be Done. He stresses that while templates can guide discussions, the real value comes from understanding the customer's context and the nuances of their needs.
"yeah I think like all Frameworks um the right answer is to to pick your set of Frameworks have more Tools in your tool box and then actually understand when and and and how to apply them so we try to ..."
Cultural Integration of Frameworks
In this segment, Tolkin highlights the importance of cultural integration when implementing frameworks like Jobs to Be Done. He shares insights on how to encourage team members to think critically about customer needs and the broader context of their problems.
"deeper to talk about how you actually implement it do you have like templates of like you have a startup project there's like as a blank I blank blank blank how do you so we we we do have I would say ..."
Choosing the Right Framework
Brian Tolkin concludes with thoughts on the importance of selecting the appropriate framework for different situations. He cautions against dogmatism in framework application, advocating for a balanced approach that considers the unique needs of each project.
"stage so you could be in the ideation stage which might look very different than uh you the very end of the process like hey we're getting we're getting ready to you know speak speak now forever hold ..."
Navigating A/B Testing Challenges
In this segment, Tolkin addresses the complexities of A/B testing at Opendoor, where the volume of transactions is significantly lower than at Uber. He shares insights on how to effectively conduct experiments, the importance of power analysis, and alternative methods to validate hypotheses when traditional A/B testing isn't feasible.
"you're talking your friends with Kavon and jobs you done on Twitter was uh quite quite the journey for them traumatic for a lot of people I think it went very far to the extreme of the yeah I think th..."
Building Conviction in Product Decisions
Brian Tolkin elaborates on the necessity of increasing conviction in product solutions, especially when A/B testing is limited. He discusses various techniques to gather insights, including customer conversations and observational data, and emphasizes the importance of trusting intuition when data is scarce.
"um it is obviously the gold gold standard and so we do as much as we we can of AB testing that are parts of our funnel and flow that have more volume than others so top funnel AB testing easier than t..."
The Role of Intuition in Product Management
Tolkin shares his perspective on leveraging intuition in product management at Opendoor. He discusses the balance between data-driven decision-making and trusting one's instincts, highlighting the importance of feedback loops to validate product hypotheses and ensure alignment with customer needs.
"okay but what the the only mistake here is like thinking you'll get an answer in a month when you won't and then pretending you do and then waking up a month later and being like well it was insignifi..."
Lessons from Zillow's Market Entry
In this segment, Brian Tolkin reflects on Zillow's attempt to enter the iBuyer market and the challenges they faced. He discusses the complexities of the real estate business and the importance of vertical integration, drawing lessons on how companies must be prepared for operational demands when expanding into new markets.
"Precision I want to spend more time on the last point but real quick the power analysis you talked about there's people don't know there's calculators out there that you could just plug in here's how ..."
Staying Focused Amidst Competition
Tolkin emphasizes the importance of maintaining focus on customer needs rather than getting distracted by competition. He shares insights from his experiences at Uber and Opendoor, illustrating how understanding the broader market dynamics can help companies thrive despite competitive pressures.
"data driven and then it's when we come into this challenge right where we say okay like let's that is another technique or tool in the toolbox I think the generalized version of that is customers prod..."
Navigating Competition with Zillow
Brian Tolkin discusses the competitive landscape with Zillow entering the real estate market. He emphasizes the importance of being competition-aware but not competition-focused, highlighting that the majority of home transactions still occur through traditional methods. Tolkin shares insights on maintaining confidence and focus on customer needs despite external pressures.
"that just like when you're taking on something completely different uh you may it may not fit into the way your company operates and partnering makes sense anything else there that's interesting to sh..."
Staying Calm Under Pressure
In this segment, Tolkin shares his strategies for remaining calm and level-headed during high-pressure situations. He reflects on his experiences at Uber, where stress was a constant factor, and discusses the importance of not reflecting stress onto teams. He introduces mantras that help maintain perspective and clarity in chaotic environments.
"comes from being able to stay focused on that regardless in thetive environment again because it's not like the market is fully saturated this is the same thing back in in the Uber days as well like t..."
The Importance of Perspective
Brian Tolkin elaborates on the necessity of experiencing stressful situations to develop a calm demeanor. He discusses the value of learning from past experiences and the importance of understanding that challenges are often not as dire as they seem. This segment emphasizes the need for leaders to maintain a clear head to foster a positive team environment.
"kind of along these lines something else I've heard that you're very good at is staying very calm under pressure and staying very level-headed when things are really crazy this is something that a lot..."
Finding the Kernel of Truth
Tolkin explains the concept of finding the 'kernel of truth' in product management amidst a sea of ambiguity. He discusses how to sift through various signals and feedback to identify what truly matters for customers. This segment highlights the importance of focusing on core customer needs rather than getting distracted by noise.
"next time it comes around you can you can say hey I you know I've been here before you know I've I've slopped on the floor in China before launching you know Uber pool and thinking we're going to miss..."
Leveraging Technology for Impact
In this segment, Tolkin reflects on his time at Uber and the importance of focusing on the core functionalities that drive the business. He shares insights on prioritizing tasks that directly impact customer experience and the significance of understanding market dynamics to leverage technology effectively.
"so just hearing of other people's crazy experiences and kind of building on this muscle of like okay they've gone through crazy stuff things work out yeah totally we'll make it we'll make it through o..."
Documenting Ideas for Clarity
Brian Tolkin discusses the importance of documenting ideas and feedback within product teams. He emphasizes that capturing insights not only helps in referencing them later but also ensures that contributors feel heard and respected. This practice aids in identifying what truly matters for product development.
"that uh if there's not an example that's totally fine but when you talk about this finding this kernel where Tech could be highly leveraged is there any example that comes to mind of that working out ..."
Lessons from Uber Pool's Launch
Tolkin shares a story about the early days of Uber Pool and the challenges faced during its launch. He reflects on the importance of liquidity in the carpooling product and how initial strategies needed to pivot based on real-world feedback. This segment highlights the learning process from failures and the necessity of adapting strategies.
"anything you find to actually operationalize that I've seen different companies do it do it differently but wherever you tend to try and keep a backlog whether that's yeah a Google sheet or your actua..."
The Evolving Role of Product Managers
In this final segment, Tolkin discusses the evolving landscape of product management and the diverse skill sets required for different types of PMs. He emphasizes the importance of aligning a PM's skills with the specific challenges of a project, advocating for a thoughtful approach to hiring that considers the unique needs of each product.
"people in it yep also your $5 promotion made me think of the early promotions of like the ice cream and the bunnies delivery and all that stuff yeah that was by the way uh a example of like Bully dist..."
Lightning Round: Book Recommendations
Brian shares his top book recommendations during the lightning round, including 'Shoe Dog,' 'Black Swan,' and 'The Design of Everyday Things.' He humorously acknowledges his tendency to break the rules by suggesting more than the requested number of books, showcasing his enthusiasm for learning and sharing knowledge.
"we've reached our very exciting lightning round are you ready let's do it can't wait let's do it first question what are two or three books they you've recommended most to other people shoe dog Black ..."
Favorite Movies and Documentaries
Brian discusses his enjoyment of sports documentaries on Netflix, such as 'Full Swing' and 'Drive to Survive.' He also mentions a recent Nike documentary featuring Ben Affleck, highlighting his interest in stories that inspire and entertain. This segment reflects his passion for storytelling in both sports and business.
"there that Nike documentary recently with Ben affle there is which I have not seen so uh if it's good I don't know if that's a recommendation or just an acknowledgement it's worth watching if you like..."
Influential Figures in Brian's Career
Brian reflects on the mentors who have shaped his career, particularly Jeff Holden, the former Chief Product Officer at Uber. He expresses gratitude for the guidance he received early in his product journey and emphasizes the importance of mentorship in professional growth.
"should have said on your pending child thank you lucky for you I have a newsletter post with all the products you should buy it's called Uh new parent gift guide for product managers love it will um d..."
A Wild Interview Experience at Uber
Brian recounts the story of his unconventional interview at Uber, which took place on July 4th. He describes the intense five-hour gauntlet interview process and his unexpected conversation with Travis Kalanick, the CEO at the time. This anecdote illustrates the high-pressure environment of early-stage startups and the unique experiences that come with them.
"um grow my career but also uh try to pay it forward a little bit in terms of people who are't really in the career that was where meure me last question I hear that your interview at Uber was pretty w..."
Closing Thoughts and Online Presence
In the closing segment, Brian shares how listeners can connect with him online and expresses his openness to feedback about Opendoor's product. He encourages engagement from the audience, highlighting the importance of community and communication in product development. This segment wraps up the conversation with a call to action for listeners.
"pretty flexible I'll have about next Tuesday great so we scheduled it and then on uh Friday or Saturday over the weekend uh I looked and like oh Tuesday's July 4th I'm like I scheduled my interview fo..."