YouSaid · the spoken record

Ayesha K. Khanna

lines on the record: 88
first: 2025-12-08
most recent: 2025-12-08
sittings or episodes: 1
sources: podcast

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“Would guess that there would be very nominal changes in this. Like, if you think a lot of companies already do roundups to help charities and other kind of local initiatives. So I believe that the elimination of the penny and kind of rounding up a little bit isn't going to like meaningfully change the behaviors we see just in the industry. Time will only tell, though.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“So I think a couple things. First is many countries, Canada and Australia already do this, right? We're alive in Canada and Australia, so we've had to build the features and capabilities to let sellers do roundups and all that other stuff. So we're excited to just enable that for US sellers. Now there's always a transition period where it's a little bumpy to start and then it gets better over time. And from just a pure point of sale helping sellers run a business, we're ready and set for them to make this transition.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Just going to say, I've been asking for years. Why would anyone spend a Bitcoin? And no one has ever given me a reason. We've talked about the future of money. Let me just drag us into the past of money to close this out. You run point of sale terminals. You run hardware. You have to accept cash. The United States government just decided to round up all cash to five cents. Like we're just getting rid of pennies. Goodbye. How is that affected your business? Did you know that was coming? Do you have to recode the point of sale terminals to be done with pennies”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Ultimately, you know, people need to make decisions for themselves, right? And I think I want to build the technology so that people can make those decisions and that they don't have gatekeepers, right, that are making decisions for them. And as long as I can do that.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“This is what I mean. I can't think of a reason to sell Bitcoin. By the way, I'm not allowed to hold Bitcoin. It's like just like holding stocks. It's a thing we can affect the price of. But I understand why you would hoard Bitcoin, like why a seller would be like, oh, I can just convert my revenue to Bitcoin. This is great. It's very easy. Can you think of a reason why you should use a Bitcoin if you're holding one?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Comment specifically on the kind of number of transactions. We're seeing a lot of adoption and interest in just a Bitcoin product portfolio, right? So conversions is taking off a ton, right, which is basically taking a percentage of your sales and converting those to Bitcoin. And there's a ton of excitement from a lot of sellers and a lot of customers on our very recent Bitcoin payment rail launch a couple weeks ago.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Not significant, no, but I believe what we want to see over time is giving both sellers and customers an option, right? At the end of the day, there's not a lot of options for digital currencies or digital ways to do transactions, let's just say, that aren't Visa and MasterCard, right? You have ACH, kind of slow, right? You have other payment mechanisms and payment rails. So we just believe that it's important to offer options. sellers and customers again will choose technologies that are both more cost effective, better user experiences, and as long as we keep investing in that, I believe good things happen over time.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I think about crypto generally and why am I transacting it, why you might not transact in it, the idea that, you know, number always go up, just the first thing that comes to my mind. And it actually today you and I are talking, and Bitcoin is down substantially. So maybe the answer is it feels different today than on every other day. But if I had a Bitcoin, I can't think of a good reason to spend it. To me, this is a real problem is that the culture of Bitcoin is you should just hold it as long as possible because number always go up. Are you seeing significant transaction volume in Bitcoin on your network?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“A very philosophical crypto question, but here we are, you know, the argument against lightning is that it centralizes Bitcoin in specific ways, right? People actually hold the Bitcoin and then now you've just built a database again that some centralized providers hold and it you've reduced the actual decentralized nature of Bitcoin. Do you buy into that?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“The Bitcoin mainnet, like the Bitcoin network, isn't fast enough to transact. However, Lightning is fast enough. And this is where Block has made, I would say, monumental investments in the Lightning Network, where one of the largest lightning nodes. And if you combine those capabilities, you get both all the benefits of the Bitcoin network with the speed that Lightning provides.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“That we're building within the Bitcoin space. It's really that it's helping sellers accept Bitcoin and they can settle in fiat. They don't have to take Bitcoin. That's fine. Bitcoin as a payment rail is super interesting. Our goal is to make Bitcoin everyday money. That doesn't mean you have to like hold Bitcoin, right? You can choose to hold fiat if you'd like to. And again, giving sellers that choice, I believe, is super important.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I think effectively the whole space is fascinating. And if I think just from a square perspective that we always want to help sellers accept any sort of payment, right? And just make the sale. That's how we were founded. And that's one of our core principles. Sellers can't control how customers want to pay, right? Which is why we truly believe helping sellers accept any type of payment is super important. Back to my point about democratizing technology, right? You know, there's a lot of talk around Wall Street having Bitcoin treasuries and all the other kind of tools that they have. I truly believe providing those as options to small businesses and guardrails and guidance and education is important, right? We should give sellers choice. I believe that they're far more intelligent and can make those decisions for themselves. And I think if you kind of see about all the investments and all the tools.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“The weirdest way to think about databases, in my opinion, is to think of money as one giant weird database. You know, the banks are all just databases with fancy faces on top of them. Credit card companies are just databases. Jack Dorsey is big into crypto, which is a decentralized database of money. Bitcoin is just an openly readable database that you can transact on. How do you think about that interaction? Block has big investments in crypto and Bitcoin. Those numbers go up and down that might change the company's balance sheet day to day. And then obviously you can transact in alternative currencies. How do you think about that relationship? Because it is like the last database to conquer.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“At the end of the day, we have to help sellers sell where they want to sell, right? We can't control that. We shouldn't control that. We should enable that in whatever ways. I think the goal for us is to provide enough tools to enable sellers to create direct connections with customers. It's one of the reasons why we launched this new neighborhoods product built into Cash App, because we want sellers to maintain and kind of enhance the interactions that these sellers have with customers, mainly around loyalty programs and re-engagement. I think the more that we can do that, the better it is for the seller. And also over time, the better it is for customers.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“You're saying this Square has done a big integration with Uber Eat store Dash Grubhub because that is the audience funnel. That's where the customers come from for a lot of these restaurants. Is that intention with one of our goals is to enable more direct customer relationships?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I think everyone is going to. Want to expose capabilities to these agents, right? And let those agents do certain things on their behalf. I think at the end of the day, we want to make sure that sellers and customers can build some sort of relationship, right? I think I firmly believe that the main streets and the neighborhoods of the world are better because of interactions that you have at those small businesses. DoorDash is notorious for trying to kind of separate the customer from the seller, right? And have kind of the DoorDash tax as you call it. I think for us, what we want to do is just support end-to-end seller. Interactions, right? And if we can have agents enable that and make that better, then that's definitely something we're interested in”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“And then the AIs can just come and use that database and services like Uber or DoorDash might lose the value add, right? They might all just become wholesalers or commodity providers of sandwiches. Small businesses have that same problem in different ways. Square sitting on top of business or running a business, having a bunch of AI features that can talk to a bunch of other AI agents that might run around and do things kind of creates that problem. Burrito delivery might change, and maybe we actually bring the power back to the quickservice restaurant in the neighborhood to just be the provider of burritos without a DoorDash sitting on top of them and extracting fees. Is that on your mind as a potential solution or change that AI might bring about?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Just a part of me that says if you don't show people what they can do, they won't even try. And then what scrambles that with AI is you can ask it to do anything and it will just confidently say it's happening whether or not it actually is happening. And there's some new dynamic that needs to be invented there. I want to just talk about databases for one more second and that how AI might interface with them. And then I want to talk about just money. Because it is a weird time for money, and I want to make sure we talk about that a little bit. I've been talking a lot about what I call the DoorDash problem, which is you turn every business into a database.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, I mean, it's kind of a very interesting philosophical discussion. I think the way that I would think about this is, you know, back in the day where, you know, I used computers back then too with file systems and dragon, you know, as we've built more software on top of those things, we've been able to do more with the tools, right? And honestly, I don't know if Gmail has files and folders behind it. I don't really care, right? I can do way more with Gmail than I can do with all those things in the past. Part of me is that one, like AI tools need to build trust with the customers and people using it. That's, I think, a bedrock belief that we have when building these. And that means there's some sort of like explainability about what's happening. And our strategy is to be able to present sellers, kind of what's going to happen and let them take some control over what's going to happen. As far as how this is going to impact, you know, my kids or the next generation.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“That's the tension that I find the most fascinating, all of this. I am a proponent that no UI should be hidden. This is just, I grew up in the sort of Windows and Mice era. Like we just put all the UI in front of your face. Like we moved from the command line to here are all the buttons and then over time we have abstracted everything away and now the kids don't know how to use file systems. There's a real push and pull there that has some real consequences. The iPad kids do not know what files and folders are. Now we're going to abstract more of the UI away, but you can just ask the magic box to do anything and it will at least tell you that it's doing it. How do you see that transition? Part of me that says people won't actually know the full capabilities of the tools you're giving them”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“So if it's pretty straightforward to have these large language models generate those UIs. And then what you can actually do is for the longest time, the builders of tools, right, like the software teams were specifying and designing the user interfaces. I think for the first time ever, the interface is generated by the customer or the user. I think that's like a pretty profound way to think about what the future over the next couple years is going to be with how these products are going to be built.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Bulk update all the prices of my menu, right? Let's say increased prices by 5%. In one world, you would just have the agent go do that and commit those changes. And those would go live on your point of sale and your buyer surfaces. That's pretty risky, in my opinion. Another path you could be say, okay, I'm going to generate a form in a list of all the things I want to change, and then the user, the customer, needs to go click OK. Boop, and then that actually goes and commits those changes. And I think that's the next frontier after we've done a lot of work as an industry on kind of this tool use agentic thing is like, how do we have more natural interactions in a generative UI construct to help sellers kind of use these tools? And I think that the realization behind all of that was that if you look at most UI, it's really forms and lists of things.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“My mental model now is more that these large language models are becoming more like the CPU different products that we're building. And you need to give the CPU different things, right? You needed to give it access to data. You need to teach it how to use sandboxes and different tools so that it can effectively learn and get stuff done. You need some working memory, right? You need all these constructs. I think ultimately even if you ask someone to go do something, like they sometimes do the job wrong some percentage of time, right? Humans using computers are also not deterministic, even if clicking the button is 100% deterministic. And this is where I think there's really interesting UI challenges and things that we're working on and going to be releasing kind of in our spring release next year is how can we have these large language models prompt the user with actual generative interface. I'll give you another example.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I think it's an extension and just a realization of how to use for many years I don't think we totally knew how to apply these things to real problems. It was this like very cool technology and there was this like capability overhang that we just didn't know how to apply this perfectly tool use and context window expansion right both of those you kind of have to do together because you kind of have to put all this data somewhere are really the two big unlocks. And then the ability for these agents to work over a longer time horizon, right? So 30 seconds, one minute, two minutes, five minutes. Like it'd be totally reasonable for proactive insights for an agent to work for a couple of minutes or more, right? Collecting data, testing it, making sure it's right before builds a comprehensive report, kind of like deep research and others. And I think those two innovations have really unlocked, I would think, far more tangible business value.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“This hybridization between we're going to make it write real SQL code so it's actually doing deterministic calculations. This feels like the turn that the whole industry is making, right? We're not just going to let the models run off and do their thing. We're going to use the models to accept natural language input. And then we're going to make sure we do real computers in the back. That turn feels very big, right? It feels like not just we're figuring out how to use the models better, but maybe we're acknowledging that the models can actually do the work that everyone thinks they can do. Do you see that as a limitation or do you see it as an extension of capability?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Is part of the art of building, I would say products in today's age, right? So there's a few things. When first ChatGPT first came out and a lot of these large language models came out, there was a lot of quote hallucination, right? You would ask these things, they'd just be like blatantly not true. The real innovation, in my opinion, is one, yeah, they've gotten better at pre-training and better kind of data inputs. But the second really is that we've taught basically these large language models to do better agent loops. This is one of the reasons why like Gemini and ChatGPT are much better now is that they in a”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Square have a database of historical weather patterns. You have to go out and get it, like that's right, just foundationally, that's the first task. We need to know what the weather was like on Sundays. We need to understand whether it was raining or not. Maybe how much it was raining. We need to synthesize that with a database of sales that has both the core revenue and then the tip revenue in it. And then we need to plot that out. I have asked various LLMs to do tasks like this, and sometimes it works. It works to a degree that is high enough that I understand why the entire industry is betting on it. And sometimes it just crashes out, man. Like, just doesn't work at all. First, tell me, do you have a database of weather that you've been tracking against sellers? Like, right, this is just a first problem. And then how do you make sure it works every time?”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“So there's kind of two things that we're thinking about. One is Sellers intuitively know their business far better than we do, right? Like just honestly, right? They wake up, they're in it every single day. They know the things that are keeping them up at night, right? Should I stay open an extra 30 minutes? And what does that do to my tips on Thursdays or whatever? I don't want to discount how well they know their business is. So, you know, there's very specific things they want to find out to help them run a better business. And I think the interesting next step is how we can be more proactive and proactivity for suggesting things that they may not be thinking about. And this is also when you combine these large language models with tool use, right? You can actually get very grounded correct things to help them understand what's happening. And that's like a really key investment area for both us and most of the industry.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“And I think that's super unique in kind of a set of technologies. So you're talking about the interface isn't so different. I would argue that the interface is completely different now for two reasons. One, almost every interface in, let's say maybe Web 2.0 world was synchronous. You had to sit there and you had to push a button to get an action. Now for the first time, you can have asynchronous things, right? It can do something on your behalf and it'll check with you for approvals and making sure that I can go do that. But I think that combined with the fact that it's a more natural, both voice and text, right? Soon we're going to, you know, voice is really good. And, you know, honestly, I know Siri had some struggles, but like, you know, voice is getting like really, really good as an ajentic interface. When you combine both of those and you combine just that these sellers are busy, right? And now they can meaningfully meaningfully know how their business is working and make better decisions. What I think happens is that we see”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“UI with a bunch of drop downs and buttons and charts that are A, not always, even if you. Them beautifully, like just hard to use, right? Getting access to data across all the different dimensions of your business, right? Sales customers, et cetera. And then the intuitive thing about like, okay, I want to look at my sales on a rainy day versus not a rainy day over the past, you know, summer. There's a pretty complex question or like, how are my tips different on rainy days versus not, right? I think for the first time these kind of agentic systems give sellers a natural language way to answer questions about their business, like kind of letting their curiosity run free.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Just Craig, I don't think Square is only differentiator is hardware. It's one of the key things, but I'm going to come back to the customer, right? These small businesses, whether you're running one location or like 10 locations, making good decisions is actually like one of the hardest things about running a small business. You just don't have a ton of time, right? You're sweating, making sure that, you know, the, you know, you've got your food delivery, the ingredients showing up that day, that your staff is showing up that day, that you're doing enough on marketing to make sure that you can generate interest for your business. At the same time, you know, you have access to data, but it's very difficult and interrogate that data in a meaningful way for your specific business. So if you kind of just think about the customer, it's really the first time that the interface for accessing decisions and data is not some complicated.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“A big user interface shift, right? That is a software architecture shift. Now the databases can just talk to each other like old friends or like whatever they're going to do, but it's not a, we need phones to make Uber because the internet is with you all the time. How do you bridge the gap? Because that is the thing that I see most of all. We started off by talking about how squares differentiation is hardware. And now we're at, we have to rearch for the AI era. And I can't quite connect those two things together.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“The idea that a business is just a collection of databases and that you should connect those databases and run your business more efficiently, right? That's the metaphor. I see it everywhere now. Everyone that I talk to about AI is like, finally, I can send my agent off into some database that previously had some weird API and it was very brittle. I can set up the MCP server and I can just finally tell me all the information that I've always needed to know to sell widgets more effectively. And I say that not with derision. I just say it because I hear it so much. But even on Squares roadmap, that is kind of what Squares AI roadmap looks like, right? You're going to have a bunch of information in your business and you, the small business owner, are never going to set up all the tools to get value from that data. So you'll just ask the AI. The AI will build the tools and then you'll have it. And that is a very big vision of the future. I see that. I see why you're describing it as a big vision of the future. That is not.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Lot of companies at that stage had like a little mobile team off to the side building a little app right and that was the strategy for a lot of companies a lot of those companies didn't make it right the companies that made it were the ones that reimagined how they should work with this new way of reaching customers and this new technology right uber reinvented transportation in a mobile device right square i would argue reinvented payments on a mobile device right and i think you know that we could debate if ai is another one of those kind of seismic shifts i believe it is um and i think companies that embrace ai and kind of really ingrain it with both the products that they're building but also the internal processes they have are the ones that are going to make it and the ones that don't you know might not”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“He's pushing the hardest on AI. We have kind of automation is one of our top priorities as a company. And it's not just automating products for sellers. It's also just automating internal processes. And that's everything from support sales all the way through compliance, risk, et cetera. And there's just this fundamental belief that if there is a process, we should try as hard as possible to automate it. I think it's the right, exactly the right push just because of how much and how fast this technology is changing and improving, there hasn't been a technology in, let's say, like past 20 years that improves by like an order of magnitude every 12 months. They're just really hasn't in a long period of time. And we can debate on a lot of the impacts of that, but you kind of have to skate to where the”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I think it's one of the reasons why I'm still here 11 years in. I think Jack is an incredible visionary leader. I sometimes joke, and I think he lives in the future. His has a great intuitive sense about what's important for customers and where markets and things are going. Jack and kind of his directs are really responsible for setting the overarching strategy of like, these are the big opportunities where we want to go. We've made some good decisions and we've made some bad decisions at the kind of corporate level. I think with the new focus of kind of these functionalized teams, we're making better decisions every single day. Again, from that alignment and actually forms for Jack to weigh in and kind of provide guidance and input on things that teams might be struggling with.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Or whatever, great. It's really just another way to say, can we align on this thing and can we go run as fast as possible? So I think a lot of my job and a lot of my team's job is to make sure that we have that alignment at Block and Square specifically, the kind of singular roadmap and top of priorities help with that. And then within that, the DRI model can help make sure those decisions are cascaded down, owned, and kind of driven towards completion.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“You can be quote good at making strategic decisions. Then if you think about actually making them, the biggest thing is like, should you make it or should someone on your team make it? And like if it should be you, great. Then you need to decide how much information you need to make said decision. And in that case, it's usually starting from the customer and working backwards, right? One ask you last note. I think decisions are kind of important, but what's even more important is just alignment of the entire org, right? So this is why startups can move fast. Alignment is simple. You're like literally sitting with 20 of your coworkers and you can make a decision and just run immediately. Right now, if you think about a remote company or a larger company, alignment becomes more and more difficult as you add more people into the equation, right? So I think it's important that when decisions are made that, you know, I know a lot of people talk about disagreeing commitment.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“The thing that I've kind of been reflecting on is that I think you need the terror of decision making, right? You need the right ingredients as a leader to be able to make decisions. And I think it's really steeped in a few things. First is deep customer empathy. It's hard for me to believe that you can make great decisions if you don't really understand who you're building for and why you're building for them. I think two is you have to understand the market. You have to understand the history, the market, like kind of like maybe the environment that you're competing and building products in. And the last one is just constraints. And I think you need to understand, you know, effectively, intuitively almost, what the different trade-offs and constraints are. If you have kind of all those, and I joke with my team, like your gut is the best trained ML model on the planet, right? Like it's just the synthesization of all the things that you've seen over your entire career day to day, right, in and out. And I think if you have kind of a lot of those components, then you could.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“I'm excited for this question. So, I think one is, I kind of think about this in two ways, tactical and strategic decisions, right? So at any org of any size, speed and decision making and making sure that the machine doesn't get jammed up, so to speak, is critical, right? So part of our decision-making process, I think, for the org, and I'll get into mine specifically, is that you want to make sure teams, right, the squads and the teams at the ground level have rituals that they can get decisions made quickly. So at the team level, we do pit stops, which are multi times per week. They can get unblocked. And then at the leadership level, we have what we call unblock meetings, right? Which is anyone can kind of sign up and bring a decision to kind of cross-functional leadership to kind of weigh in on a path. We aim to have decisions made within 48 hours or less. Very difficult to get to that timeline all the time. But that's kind of just a stake in the sand that we've put. So that's the tactical side. I think on the strategic side,”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“It really starts with the strategy and the customer problem, right? So we strategically say that QSRs and FNB is a priority for Square, which it is. They're kind of the core cornerstone to the neighborhood. And it's kind of a...”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“We have a financial suite team. So Financial Suite is think about a lot of the cost of goods sold. So things like reporting, accounting, kind of et cetera. Then we have a growth team. Every team needs kind of a growth growth org that helps with onboarding conversion, et cetera. We have an identities and trust org, right? Helping sellers take payments safely and effectively is super important. We have a foundations team, right? So one of the things you need in, I would say most orgs, either functional or divisional, is a team that's helpful for ensuring that the general experience, right, whether that be like navigation, design systems, things like that are cohesive and good. And it kind of acts as a check and a balance to a lot of the product teams that are moving very fast to build capabilities across their areas.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“The biggest challenge with Square, like I mentioned earlier, is that we serve every segment, right? We serve food, retail, health and beauty, services, kind of a long tail of other kind of types of sellers. So the core decision that we had to make when we kind of kind of restructure around functional versus GM was do we organize by customer or do we organize by like like functional surface right so like you know do you need do you need like a retail team that wakes up every single day living and breathing kind of the retail customers and the retail workflows or do you kind of just have more generic pillars like you know orders and payments and stuff like that i think ultimately the decision we came to was both and that we have um kind of key product areas that are focused on food and bev retail local services and then we have a whole set”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Kind of really build interesting products at the intersection between all those. So that's kind of the journey, I believe Square has gone over the past couple years. And one of the reasons why very invigorating to work, I've been here for almost 11 years, a little over 11 years now. And I think it's the ability to move fast, the ability to make quick decisions, and the ability to kind of build these products at the intersection of both the business units is just incredibly exciting and fun.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, yeah, totally. And I do think they oscillate based on different things. And I think the reason that kind of leads us to square 3.0, which is really that there was a realization that the benefit of block as a company and the benefit of the two great products that we've built with Cash Appen Square is that their strength really is at the connections between the business units. It was just very difficult to do that in a divisional model, right? Like the incentives are just completely misaligned. Divisional models work super well if you have like completely separate P&Ls and the products rarely have to talk to each other. You can kind of hire and build whatever cultures you want within each of those areas. It doesn't work super well when you want kind of that one plus one to equal three, let's just say, right? And I think that's kind of the realization for Square 3.0 is that we wanted to, one, build with velocity across the business units and two,”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Maybe I'll just take a step back about where Square has gone over the past 10 years, right? In my journey at Square, a little bit. So, you know, square in the beginning, square 1.0. All right, this was a little white reader. We talked about earlier, right? This is kind of solely focused on growing kind of helping sellers make any sale. And then we went to Square, let's say 2.0. This is where Cash App kind of grew and scaled as a separate business unit within Square. There was a GM divisional structure where we kind of really exploded our software ecosystem to help sellers with a bunch of different jobs, right? There was a GM for the staff tools and there was a GM for kind of the order system, et cetera. As you know, companies go between kind of divisional versus functional structures all the time for various reasons. And I don't think there's a single right one for every company, right? It depends on the circumstance and the culture and the kind of market and a bunch of other reasons.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“So, not everything has to harmonize at exactly the same strategy or exactly the same things that we're working on. It's more that when you functionalize a company, you can also make sure that each discipline is operating kind of at the highest levels, right? So both from a performance perspective, but also accountability perspective. I think that's one of the key points. It's not like we're trading off people necessarily between title and square all the time. It's title as a team, square as a team, cash app as a team, et cetera. And at the margins we might make prioritization trade-offs. But in the broad strokes, that's, you know, kind of, we have our strategies and we go execute on them.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Functional structure is that alignment is super, super important in a large organization, right? And if you create kind of different, effectively different mini startups or kind of Product areas, which happens in a divisional org, then yes, you can kind of go fast in each of those directions, but you're usually going fast in like 14 different directions, right? Versus going fast and making trade-offs and being able to build together and kind of build something really incredible.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“My thesis for teams and prioritization is one, when we functionalize the company, we created a single set of priorities, right? So a single shared roadmap, right? If you have a single shared roadmap with clear DRIs for each of the areas, it makes a lot of these decisions a lot clearer, right? Because you can be like, this is more important than this. And then we can staff appropriately. I think that's one. And two, though, it's also really important to make sure that the teams and the squads are stable at kind of the kind of ground level that they're building. They have autonomy, mastery purpose. They can go kind of go build the things for customers. And you kind of need to synthesize both kind of stability at the squad team level with kind of top-down strategic prioritization that's kind of happened. And I think that's been the biggest change and benefit from going from a divisional business unit structure to a functional”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so block is the kind of company that has a bunch of brands in it. I'm responsible for the square brand from a product perspective. We obviously have like sibling teams or sister teams in Cash App, et cetera. We functionalize the entire company earlier this year, actually late last year. And it was a big change, right? Before we had kind of a divisional GM business unit kind of organization, and we went to a purely functional. So there's engineering, product design kind of at the highest levels. And then within that kind of brand focused teams that think about the different areas. Jack is an incredible leader and spends time with each of our brands kind of both guiding really the strategy, but also feedback on fit form and kind of the actual products and the pixels that we're building. So it's kind of been great to work together with him a lot closer over the past kind of year and couple.”
2025-12-08 · Decoder with Nilay Patel · Square's product chief on the death of the penny and the future of money · IDENTIFIED FROM THE TRANSCRIPT