Feb 7, 2025 · 46m · news
Brian Tolkin, Head of Product @Opendoor: How to Hire the Best Product Teams | E1257 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of the 20VC podcast, host Harry Stebbings interviews Brian Tolkin, Head of Product at Opendoor, exploring key product management lessons from his tenure at Uber and Opendoor, the evolution of the PM role in the AI era, and strategic frameworks for scaling product teams.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 23.9% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 3.4 Guest disagreement 1.7 Harry pushing back 2.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 37:25 Brian pushes back on Harry's AI thesis
When Harry asserts that AI will commoditize engineering and make it less important, Brian immediately rejects the premise with 'Why would you say less?' and defends high-level system architecture.
Hardest push from Harry ▶ 35:20 Harry attacks management buzzwords and disagree-and-commitHarry forcefully pushes back on corporate culture norms, calling alignment a BS management term and questioning whether high performers ever truly commit when they disagree.
Biggest teaching moment ▶ 14:05 Brian breaks down multi-product scaling matrixBrian educates Harry on multi-product development by mapping capabilities against customer sets in a 2x2 matrix to show how companies avoid innovator's dilemmas.
Harry holds his own ▶ 37:30 Harry presents counter-thesis on AI design valueHarry demonstrates strong sector domain knowledge by articulating how AI commoditizes median coding tasks, shifting leverage to high-end design craftsmanship.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Best Product Decision and Upfront Pricing | 2 | 3 | 1 | 1 | Harry references Brian's historical background launching Uber China Pool in Chengdu to kick off the interview. Brian explains the operational and technical realities of mapping complexity in China that were underappreciated at launch. | |
| Regional Variations in Mobile App Design | 2 | 3 | 1 | 1 | Harry asks whether Western product design is converging with Asian design paradigms like TikTok and Red Note. Brian notes the UI differences and shares a personal mistake at Uber where liquidity goals were prioritized over clear user UI. | |
| The Evolving Role of PMs with AI | 2 | 4 | 1 | 2 | Harry cites the trend of PMs moving from Figma to Replit. Brian clarifies that while prototyping tools change the execution speed, the core skillset of understanding user needs remains unchanged. | |
| What Makes a Great One-Pager | 3 | 4 | 1 | 2 | Harry sets up a specific hypothetical scenario regarding Series A trade-offs between growth and technical debt. Brian details why early-stage land-grab companies must earn the right to survive before allocating resources to debt. | |
| The Early Stage CPO and Multi-Product Scaling | 3 | 4 | 2 | 3 | Harry pushes on whether new products must directly benefit the core product. Brian breaks down a 2x2 matrix of customer segments versus core capabilities to frame multi-product strategy. | |
| Cutting Through Noise and Product Simplification | 2 | 3 | 1 | 1 | Harry quotes Brian's written commentary on product simplification. Brian explains how product managers must filter cross-functional noise to uncover the core user need. | |
| The Structural Alignment of Goal Setting | 2 | 3 | 2 | 2 | Harry asks about OKR management and questions stage-based founder limitations. Brian emphasizes human agency and explains how teams earn the right to plan over longer time horizons. | |
| Speed of Execution vs. Quality and Design | 3 | 4 | 1 | 2 | Harry brings up user resistance during major UI changes like the iPhone home button removal. Brian explains how to structure experiments to avoid novelty bias by measuring weeks five through eight. | |
| Gut Instinct vs. Fast Consensus | 5 | 4 | 3 | 5 | Harry challenges a quote from Spotify's CPO and argues that dictatorial product leadership is underrated. Brian differentiates between gathering all inputs and consensus decision-making. | |
| Hiring Strategy and Career Alignment | 3 | 3 | 1 | 2 | Harry asks how founders should evaluate PM candidates during interviews. Brian shares his philosophy that companies 'hire their strategy' and outlines effective take-home case studies. | |
| Sprint Timelines, Internal Transfers, and Team Culture | 4 | 3 | 3 | 5 | Harry challenges corporate jargon, calling 'alignment' a BS term and questioning if 'disagree and commit' leads to mediocre execution. Brian defends both concepts when bound by clear context and limited timeframes. | |
| The Real-World Complexity of Physical Products | 5 | 3 | 3 | 5 | Harry forcefully argues that AI commoditizes engineering while elevating design importance. Brian pushes back, arguing system architecture and high-level technical skills become even more crucial. | |
| Commitment vs. Valley Hopping | 2 | 3 | 2 | 2 | Harry asks about career duration in Silicon Valley. Brian advocates for staying longer at companies to compound context and effectiveness rather than job-hopping every 18 months. |
Statements from this episode (33)
Tolkin: UberPool launched with post-hoc pricing before upfront pricing was built
“When we first launched, it was variable pricing, depending on whether you matched or not. You open the Uber app, you say, this is where I'm going, and it was just like, okay, and then based on minutes and miles, the cost would post hoc calculate until we built…”
Tolkin: Chinese mobile app design favors bold visuals over Western minimalism
“And the reality is you go to China and there's, it's different, right? It's not as like the sleek, elegant design isn't where design sort of falls into the background isn't as prominent and it's a lot more, you know, color and red and big buttons and that type…”
Tolkin: Western and Asian mobile app design styles are converging
“I think there's absolutely a convergence. I think probably the influence is a little bit more being pulled towards us, but the reality is like apps like, you know, TikTok, there's a lot of things going on, things flying around, scrolling, all that stuff. Like …”
Tolkin: Defaulting the Uber app to UberPool was a poor product decision
“And for a little bit the default was Uber pool. And I think that was a poor product decision. Because even if you had chosen Uber X on your last ride, it defaulted back to Uber pool. And so the UI wasn't clear enough what was happening. And so people were acci…”
Tolkin: AI will cause engineering, product, and design roles to converge
“And I think we will see that we'll see a collapsing or converging of the end product design triad. I think they will never be the same, but I think everything will be pulled in tighter. So I think all of that will change.”
Tolkin: AI expands PM tools but core product skillset stays unchanged
“I think what changes is your ability to communicate those ideas, your ability to do more upfront, your ability to do better user research because you can show prototypes easier. So I think the tool chest gets bigger, but the core skillset of like, Actually fig…”
Tolkin: More PMs will start development in prototyping than design tools
“I think maybe, maybe the generalized version of that is do more PM start in prototyping land than they do in strictly design land? And I think the answer to that is yes.”
Tolkin: AI will collapse product cycles by skipping documentation for prototyping
“And I think AI completely collapses that cycle and accelerates a lot of the upfront up funnel work where, where again, you can just do, you can build a prototype and you can show that to customers and like the PM and the designer might just work collaborativel…”
Tolkin: One-pagers fail when focusing on solutions rather than problems
“I think people get wrong where the one pager is the solution description, not the problem statement.”
Tolkin: Early-stage startups should prioritize growth over technical debt
“Like you have to earn the right to exist in the future and paying down tech debt doesn't pay the bills. And so I think at that stage, it's probably a little bit early to start paying down technical debt.”
Tolkin: Early-stage CEOs must act as Chief Product Officers
“Always no, but in the early stages, yes. So, you know, there are certain scales of companies where that, you know, maybe doesn't make sense anymore. But in the early days, yeah, I do think they should. I think outsourcing your, if you think that the most impor…”
Tolkin: Launch new products in sandboxes to protect core offerings
“I think the best way that I've seen this approached is by giving new products a little bit of a sandbox, a contained sandbox that relaxes a bunch of the constraints of the company. But does it in a way that if it's completely fails or whatever, it actually doe…”
Tolkin: Uber Eats was created as an entirely separate app and org
“In, you know, Uber's case, even more extreme is you do what Uber Eats was, which was like a totally separate app, a totally separate org and totally separate, separate everything.”
Tolkin: Second products must leverage core advantages or existing users
“It doesn't have to benefit the first, but it has to take advantage of some competitive advantage that your company has, right? And so if you think about sort of a classic two by two matrix where you have, you know, your customer set and your competitive advant…”
Tolkin: Opendoor is shifting its multi-product focus to seller capabilities
“We had a bunch of initiatives over the year, building a retail buyer business, building a mortgage business. And I think we could have been better about focusing on what are our core strengths and how do we not be in sort of that new customer set, new capabili…”
Tolkin: Uber's early success relied on speed, availability, and price
“For a second, there's a ton of things that make that product work or in the early days that made that product work. But at the end of the day, is there a car available? Can it get to me quickly, you know, within, within five minutes at a price that's reasonabl…”
Brian Tolkin: Opendoor's variations of a mortgage product failed
“Opendoor's had different variations of, you know, a mortgage product that, that didn't succeed.”
Tolkin: Teams earn long-term OKR planning by delivering on short-term horizons
“The more nuanced answer is you earn the right to set OKRs on longer time horizons by proving you can execute on shorter time horizons.”
Tolkin: Shipping low-quality MVPs produces false negative product signals
“I don't think you can throw out crap, right? Because the risk is then you have like a negative signal where actually your execution was just bad, right? And that's the reason it didn't work.”
Tolkin: Judge major product redesigns on weeks five through eight of data
“We're going to look at all the data, but we're not going to make a decision in the first two weeks. We have to have the fortitude, the guts, the gumption to say, we might see patterns in the behavior where behavior is slowly changing over time. And so we actua…”
Tolkin: Talking to ten customers provides as much data as 150 quantitative points
“Talking to users is data. Like that is real. If you talk to 10 customers and they tell you something that is just as much data as I looked at a 150 data points and, you know, here was the insight.”
Tolkin: Consensus product decision-making is wrong
“So I think consensus product decision making is challenging and wrong.”
Tolkin: A PM's background dictates how they define product success
“In a pithy way, someone that opened door where we're closely with had this phrase, which is you hire your strategy. Right. And so the person you pick to play that role will dictate how that person defines, you know, the success of that product.”
Tolkin: Failed hires are almost always the company's fault
“So I believe that poor hiring decisions are almost, are never just the person, never just the responsibility of the person being hired, the new person who it didn't work out with. It's almost always the company or the hiring person's fault, right?”
Tolkin: PM interview tests should measure clarity of thought over tactics
“And I think the Important part here is it can't be so narrowly scoped because the tactics of the job you can learn, how to run a sprint, how to do prioritization, like that, that stuff you can learn. That's not what the test is. The test is the clarity of thou…”
Tolkin: Chronic disagree-and-commit signals an employee is in the wrong role
“Can I disagree and commit for sure? Right? Because that, that is like how we make velocity based decisions. If I'm disagreeing and committing too much, Then, yeah, I agree with you. Then, like, I'm in the wrong place because I'm not aligned to where we're goin…”
Tolkin: Internal transfers into product are an undervalued PM hiring source
“I think there is a tremendous amount of undervalued appreciation for internal transfers from other functions into product at the same company.”
Tolkin: Top 5% of tech talent gains value in the AI era
“The top one percent, the top five percent of all of the skill sets get a lot more valuable and the median gets a lot less valuable.”
Tolkin: Opendoor includes product ops in core product team structure
“At Opendoor, and I think this is true at a lot of operationally intense companies we actually consider sort of the classic triumvirate of end product and design and product ops and design, because it's so difficult to divorce your digital product from, you kno…”
Tolkin: Frequent job hopping limits professional growth and impact
“I think the reality is you just become more effective and therefore you can do more more, more, more quickly. You have deeper relationships, you have deeper context on the company, you have deeper context on the customer base, and therefore you can be more eff…”
Tolkin: Operations creates the most cross-functional tension with product teams
“Operations. The speed and cadence and types of problem solving is, is, is very, very different. And so it can be very challenging to all speak the same language on things that have a product or technical solution versus an ops based solution.”