Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

[MUSIC] Well, let's do it. Thanks for joining. Thanks for having me here. So maybe a place to start is just your definition of what an excellent chief product officer does and what's the impact they're having on the business. Yeah, I think a lot of people think a good chief product or an excellent chief product officer actually helps ship stuff. But that's from my experience far from the truth. The key job of a great chief product officer is essentially setting the direction, not worrying about every single feature, not worrying about even reasonably reasonable size products down to every feature level, but setting the vision and the direction for the product, which then aligns with the vision and direction for the company. And then building a team around it that can execute down into the details. Because if you have achieved product, most people think a chief product officer is someone that decides the roadmap, someone that decides how each feature ships, how it's designed, et cetera. And I don't think you get really good products based on that. So that's one. I think the other thing for an excellent chief product officer is just like understanding your customers deeply so that you can decide what bets to make because you can't make every bet. And so if you don't truly understand your customers deeply, what ends up happening is you make bets that don't really add value. And then the third thing I would say is resource allocation. Right. Where do you actually, let's say you made four bets, they're not all equally important and they're not all equally complex. So how do you design your org, design your resources or allocate your resources in a way that you can move those forward? And people think resource allocation or design is a one time thing, but it's not the world around us these days changes every quarter. So these are decisions you have to revisit almost every quarter. Do you think that definition that you outlined is the same for all great companies? Or do you think that chief product officer role is quite context and maybe CEO or founder dependent that you're working with? So I think that the basics of being able to explain to your team, the direction of the product, understanding your customers and resource allocation, bets and resource allocation is the same. I think the process of getting to it is very different, different companies. So if you have a founder as a CEO, the founders had a vision for a while. So really is, you can't go off into a room with your team and co-creative vision. That's usually hard because I've worked for a founder. I was it octahed up before zero and I went for a founder. You have to co-create the vision with the founder and to a very large extent actually influence the founder because at the end of the day, they've been thinking dreaming of this for 10 years. What you can often get to the table is the depth of understanding of the customer. That's where you can come from because very often a founder starts with the deep understanding and intuition of the customer, but then they're running a company at the end of the day. And so it becomes all that understanding. And that's where you can help co-create the vision. So that's one. I think if you are working with more of a, I'd say, an of a executive CEO, you still co-create the vision, but you co-create the company vision almost because product is such an important part of the company vision. And then once the company vision is co-created, you then have room to actually genuinely create the product vision. The operational CEOs are not in the, why does this button on this UI look different, but a founder will be in that much of detail. Do you think it takes a certain type of chief product officer to be successful in a founder run company that is different than a hired CEO run company or not really? I think definitely. Talk more about what? The difference is you have to be willing to give up some level of autonomy when thinking about the product in a founder-like company. In a founder-like company. And you have to be willing to, you have to know how to influence really well. And you have to be able to understand what influences the other person because often for operational executives or off at an executive CEO, it is metrics are clear business growth, customer happiness. For a founder often there, what makes them a founder and I try to start a company and I kind of got a taste of it, which is the reason they become successful is the whole world says they're on a fail. Nobody likes their idea about them. So they got instinct made them or whatever insight they had is what made them succeed. So more often than not, they will go by their instinct, whereas I think an executive CEO more often goes by repeat patterns of things that are known or data. And so how do you influence in either case is very different. Being with a founder CEO, a CEO with a founder CEO requires probably more EQ and understanding into what the founder values in addition to just the business growth. What's that dynamic of sort of like navigating that feel like? Particularly because I would assume to your point one of the things that are special about founder run companies not always different than then externally higher CEOs, but they have this feel and to your point gut instinct for the business and the customer. And so it seems, you know, you join and it seems in one way you can be overly deferential. And then in the other way, not push back enough. Like there seems like a very specific tension that you have to navigate. Look at the end of the day founders on the company to succeed. Right. So that's one thing. So if you put the best of the company before and you are recognized, and I think this is true for anyone, if you have a team player in any company that puts the company before themselves, then people know where you're coming from. Right. You're coming in the best interests of the company. You define the outcomes and you debate the outcomes. Right. So I think that is the way to neither become deferential and to not be able to have an open debate. So I think always take it back to what you're trying to achieve. That's important. And that works across the board. How you how you drive to or how you convince someone maybe different ways. One is more like, well, this is the world we could build if we did this. And the other is these are the customers we can go target. And this is the revenue we'll get or this is the value we give the customer and they become more sticky or the lifetime value, whatever you want to do. So I think those are different. But at the end of the day, if you are aligned in the outcome, I want to build a great company. I want to build a great product for my customers. And I don't care where the idea comes from. Right. The other thing everybody thinks is like pms or cpos are supposed to come up with television. Like honestly, like a vision is a collection of people coming together and understanding customers deeply enough and stitch and then yes, usually a cpo will stitch it together. But honestly, unless your job is there are very few people running around that like just sit in a room all day and can like be like end to end. This is the perfect thing to do. Do you think about it value to the customer or value to the business? I am a firm believer that if you add value to the customer, you will find a way to capture the value of engineer. And yes, I almost think of it as if you cannot capture value. Then you are fooling yourself that you added value to the customer. Right. Or enough value to the customer. So I think I almost think of those two as interlinked. And if you go with I am adding, if you focus on adding value to the customer, you will figure out a monetization model eventually or how to monetize it. So that's one thing work. I there are other frameworks that are hard that are easier to do like when you do large scale planning. So like annual planning, you always want to make sure there are rules of thumbs all over the place. I am a very Google PM in some ways. 30 to 40% in existing customers, 30 to 40% on new time, 20 to 30% on things that are really big in the shots. Right. And so you use those interchangeably. Right. You go by the rule of thumb, but really rule of thumb by itself does not work in all situations. So right now for most people, you better be taking a lot of risk in your roadmap. Right. On things that will work or not work. So and these rules of thumbs don't really work right now with everything that's happening with technology change. Sure. More about that. Well, I mean, I think right now where things are at, we all know, yes, AI will automate things. We all know AI will give you more insights. But what will it change in the product in the workflows will will apps become headless, right? What does it mean in terms of for us in accounting? Do we take risk on the accuracy? Should we in which cases? These are all like risks. Do we like does our workflow change now from a workflow that drove action now agents are driving actions to workflow that does reviews and proves it took the right action. These are all unknown, right? So we built automatic bank reconciliation. What this means is your transactions in an accounting system are matched to your cash in your bank. Our customers are like, no, no, no, no, no, you can't do this. You can't do this with the machine. There's so much nuance to it. What do you mean? I will do it and we're like, okay, but like it seems silly not to do this. And so we're still like we'll do it. But in the process of doing it, AI we achieved 97% accuracy. So we saved them like 22 hours. Each small business 22 hours a week or a month. Sorry. And then the thing we learned and we iterated our way into was people aren't comfortable till they can see how what you did. The second you can show them exactly what you did. People are happy. So but when we went into it and we went into it relatively early, it was unclear if this was a ton of effort that was going to be completely wasted. So I think, but if you didn't go into it in this era two years later, we would have been way behind. Right. So I think the pace of change is so fast right now. And the customers themselves are changing the way they use and behave with products. The day themselves don't know what they'll be comfortable with. So you do have to take some leap surface. fits and take more risk in what you're building right now. If all you're doing is what customers are asking for right now, I think you'll get a left behind. Going back to the start of the conversation, when you think about being effective as a chief product officer, what does that now look like? Let's say in 2026, you want to make more bets that are obviously EV positive, but are lower probability but the payoff could be enormous, or at least high variance. There's a wide degree of uncertainty. And you have to execute through it to sort of understand that. How do you go from that in a very high level sense to what is going to happen at any point in time and then to the point you made at the beginning, how do you think about resource allocation? Over the last couple of years in the AI now have become not mainstream. They're in your 20% bucket, but they're not the 20% moonshot bucket. It's not moonshot, but it's like innovative. And what's truly moonshot has become even more forward thinking. So like what's the difference? So an example is auto-bank-regulation work. Can we automate bookclos? Can we automate tax emissions? Those things are becoming more common. You're almost sure. If I can automate, if reconciliation works, you can automate books close. If books close works, you can automate tax. So those don't seem like things that customers wouldn't adopt anymore. It's just a question of how to build them at the right accuracy with the right workflows. Resource allocation used to be a problem. Today, you can get a lot of certainty whether you're in the right direction or with a very small team reasonably fast. The question more is how do you make sure they're not sucked in by the system and the garden ways of doing things? This is a more about that. So innovation of our different ways of thinking often happen when you have to start with nothing. Let's say we are thinking about if we were to start an accounting software company today or payments company today because we're both what would it look like? If you're sitting in an existing system, there are so many constraints as well as so much distraction that it's really hard to rethink it from scratch. So a person would go, "Okay, if I'm going to rethink an accounting system, our ledger does X, Y and Z. I need to think how I can build something to fit this." Worse somebody that doesn't have a ledger would start from, "Okay, what is the experience and then what do I need to build from there?" Somebody doing it in the system would go, "Okay, I have this other thing to worry about. I have this meeting to attend. There's this team meeting to attend." So there are multiple constraints in free space like in the ability to think and go deep. You tend to go to your existing customers which often they may not be the tech like the early adopters. So I think it's just generally relatively hard to innovate. Something from the ground up that is completely new in an existing system. So the question becomes, how do you find a team, invest in a team, create a team and keep them sheltered so that they're not sucked in that system? And is it just doing that is the answer or there's nuance to how you do that well? Well, there's nuance. The nuance is like, you're trying to create a startup if you're really. So then you have to find the right people, the right teams, the right goals. It looks, in many ways it looks very much like what you guys do except you can only lay one bet on one team and one set of people. So the probability of success also is much lower. But the difference is you do have some industry knowledge or depth of knowledge and you do have a hypothesis before you go in. You don't just say, "I'm going to start a team on the site that's going to innovate." You say, "I think the world is going to evolve in this way." SAS versus license-based model versus one in a build-of-trans action-based model. Super hard to do it in the current system. Existing customers will reward. Billing systems won't work. Sales incentives won't work. But if you put someone on the site, this is something very easy for people to understand. They have none of those constraints, right? So your hypothesis is eventually the world will move to a transaction-based model. You're not going and saying, "Oh, just figure out what to do." That's why the chances are higher. Building sort of on the AI theme for a second. What do you think is different about being excellent as the Chief Product Officer in 2026 versus excellent as the Chief Product Officer in 2022? Understanding your customers is important, but understanding your customers can mean multiple things. Understanding your customers can mean what they're asking for, and understanding your customers can also mean bringing technology to bear in a way that they don't know what they need. The second is obviously harder, and that is more important now. So it can't just be, "I go have a bunch of customer conversations. These customers want to X." It does require a depth of understanding of what the problem is. A good example there is we were being told repeatedly that we needed to show the actual bank statement during the reconciliation process. And they're like, "You have to show it. You have to show it." And when you dug deeper as an example, the issue was not that we weren't showing the bank statement. The issue was they just wanted the total. So we could have calculated our total as an example. This is not an AI example, but this kind of thinking normally in the old, before AI, you could have gone there and been like, "Hey, customer's asking for this. You dig a little deeper and it works." Here, if you don't truly understand what they're trying to do and how you can bring this new technology to bear, to deliver even more value than they're asking for, it becomes hard. So that's one thing. I think the second thing is it's not so much about I need to give this capability anymore. It is more now the way you need to think is how do I make their workflows easier? Right? It's shifted from here's the capability, do they do utilization? To how do I take what exists in front of me and collapse the workflows and make it easier so that in a lot of cases, you create new outcomes or timesaved. Business grown, right? Because you can actually do stuff for the business now. So I think it's just a different orientation. From where you sit right now, does it feel like incremental? Change? Or it's just night and day. Expand on that. Like, I understand sort of those two points, but when you pull on that, why is that so profound? Concept of an app has changed. So your ability to think about it, customers' entire day in life is just like, you can no longer think my customer wants to do this in an app. You think you have to think, my customer wants to get paid by their customer. What is the best way for me to get them paid? Worse is, I'm going to put a button that resends an email, right? Resents an email to ask their customer to pay. Now it's like, can I bring them on WhatsApp? Can I remind my customer ask them if they're visiting that? It's so many other, like, can I send them a text message? How often should I do it? When should I remind? What's the best way to get paid? All of these things are a lot more possible. So you're designing software and not with, I'm helping humans conduct work, but I'm actually trying to get to an outcome. Do you think you're flying at a lower altitude on average more in the details or the same? Here's why you're flying at a lower altitude because you're trying to change the way people work. You're trying to change people because you as one of, as you as the senior product and engineering leader are the catalyst for change for a firm, right? Because otherwise people will just keep doing what they do. So I think the way things look is, you're having deeper discussions on, you're more in the initial sausage making, you are having deeper discussions on, how does a technical architecture need to change to be able to support? Right? Like, usually technical architectures are reasonably well underserved, but now it's like, should we do this? So we have more flexibility. Should we be model agnostic? How quickly should we be able to change models? What can be probabilistic? What cannot be probabilistic? What has to be deterministic? Do we need a UI here? Will the UI be chat-based? Or will it be, will it look like it's traditional? Should chat be a sidecar? Should chat be the UI, right? Like, so you get into all these levels of details because you have fundamentally changed the app. Three years ago, we would have said, oh, I'll give you a very basic example. Let's build for the mid-market segment, right? Like, we don't just want to be small business. You'd go and say, okay, can you guys figure out how to build for the mid-market segment? And let's go figure it out. And you do a bunch of customer calls and you'd be like, okay, here are the list of features we need to build. And then your team's been through the process of building the UX, trusting the work, like, building the workflow, so they could go work autonomously and then come back. Here, every decision starts becoming very strategic and fundamental to the direction of the product, the way it evolves and the tech stack, the way it evolves for the future. What's your definition of politics or a political company or executive team? Whenever there are more than two people in the room, there's politics. This is at home. This is in a home less because you've lived with each other. And like, but this is everywhere, right? Like, it's three people, which means any two can have an opinion that the other person doesn't have. And so the way it is changed on that one person that's left out. So to me, like, if you have a company of three people, there's politics. I think to me, politics means at its core form two things. People are not rowing in the same direction, which means there's friction in the system to achieving an outcome. And people are carrying more burden of convincing, influencing a lining than they have to. And then I think that politics at the surface level, if you touch the Y, it is incentives are not aligned for some reason. What about when you think about the different businesses that you've worked at and you think about the most political environments and the least political environments? What's going on? Like, what is a CEO doing that's different? What is an executive team, you know? So I think one is so when I talk about incentives the incentive system has to be set. right, but by the CEO and then subsequently by the executives. When a leader jumps in and solves problems across their teams, there is a lot of reason for the teams to lobby for their self-interest, which then creates a me versus them. When a leader rewards collaboration, even if the collaboration resulted in an imperfect situation, as much as their reward impact, or enough, like impact is important, like enough, then I think that sets the behavior of collaboration, because it is an outcome that is, again, it goes back to incentives. If you're recognized for it, you will do it. If you reward putting the company first, versus the best answer always, okay? That's a system where, that's another thing a CEO can do, right? And when you say, "Reward the company first," it would be, "You may have the right answer," and then you're saying, "You're going to actually make 100 people demotivated," right? So is that ultimately the right thing for the company? If you think like that, and you reward that, I think that is what leads to lack of politics. And then I think, look, I think the other things are how safe do. What culture, do you create a culture of, how do you support your people? How safe do you feel? Because when you feel safe, you generally tend to act in the best increase when you feel unsafe, then you either want something for the environment or you want to change the environment. When you go back to the comment about the incentive structure, can you make that more tangible, like what? Even incentives are important for a whole host of reasons, but one is to get people to do what's best for the company. It's maybe one simple way to think about it. Talk about like the different levers. If somebody's project did not go well, but they went out of their way, project product launched did not go well, but they went out of their way to make another team better. Do you increase their comp? Does that go into their performance? Is that recognized in all hands? Do you think that is more important, less important, or the same importance versus comp? There is a balance. Autonomy, sense of purpose, growth and comp. They all need to be balanced. I don't think most people for long periods of time can just be going operated. Even beings are not made like this. Imagine working in an environment that gives you a ton of money, but you do it again and again and again and again. And you're doing the same job again. I just don't think it works in term. You tend to have a ton of attrition. You talked a little bit about the courts are creating a safer or supportive environment. What are your thoughts on when you're leading a function, the role of being demanding and having high expectations and how those fit together? I think you have to do both. If you demand, you have to demand a lot to get results, especially in this day and age. But if you demand without giving people the support to succeed and letting them know that taking risks is okay and failure is okay, you're going to have a culture where nobody takes risks, nobody tries to grow. It's a fear-based culture. There's no innovation, there's no growth, everybody's doing the easiest things, your roadmaps are sandbag, your revenue numbers are sandbag, right? Like nobody's willing to take risks. So I think what I tell my team is like, look, we can't know the future. We can only try. You can't be wrong 100%. You can't fail 100% of the times. But I don't expect a success. I don't expect a badting average of 100%. 100% I expect a badting average of depending on level. 70, 80, 70%, etc. If you go back to OKRs, your OKR should be that your average should be 0.7 in the score of the OKR. If it's always one, you haven't stretched yourselves. And it should be OK to be 0.7. So that's what I mean by creating an environment that's supportive and allows you to stretch to that's one. I think the second thing is when a person is fitting into. Let's say somebody gets promoted and is trying to do a new role. Can you make sure that not you personally, but you've created a culture where there's enough support around them? How do I do X? What does it mean to do Y? Can you give people enough time to grow into their roles? Is another example, right? If somebody takes a huge bet, can you go? So for example, we took a bet where we said and I did this. I'm like, I don't wake up in two years and find out that the entire app is agents in a chat. So we're going to go off and build our own app on the side. That is where you're going to do accounting from a chat. And it's all agents. And the effort failed mainly because customers are not there. Like they're not ready. And maybe accounting will never become purely a chat just because of the amount of data. But the team we had there, can you like celebrate their failures? Can you celebrate failures you learned from? The question isn't, shouldn't we, did you fail or did you not achieve an outcome? The question is, what is your batting average? Is it an acceptable batting average? And then when you fail, did you learn from it and you're repeating the same thing multiple times? Do you find that a portion of your job is to raise the ambitions of the org? And somebody says, well, you know, we can ship it on. That's literally my number one job. Expand on that. What you get as you get more senior in the org is you start noticing things across teams. And you also write for your wrongly have input from outside the company. And your job is to bring input from outside the company in terms of how things should function within. And so you, you're not stuck in the doing as much. So oftentimes you have more perspective. And we just went through it. My whole team is so stressed out that we were committed for next year. And I was like, no, I don't think so. I saw us go from as a system, not as individual teams, because they're looking at their own teams. I saw us go from a velocity of X to a velocity of Y, from a architecture change of X to an architecture change of Y. I am seeing the trajectory. I'm seeing which teams are of outperforming the trajectory, which means other teams can get there. And my decisions based on that. And I'm seeing where the slack in the system is. So I think you do end up getting a better sense in many ways, unfortunately, of how far you can push the teams. And so your job is to get them to rise to that level. Now, if you're always unrealist, somebody told me you're being unrealistic, right? Like they're like, when you talk like this, it sounds like you're unrealistic. And I'm like, okay, let me show you the data I'm seeing. The data I'm seeing is here's the benchmark. Here's where we are at. We've increased by productivity by, let's say 50% in the last two years. And the world is increasing productivity by another 50%. So we should be able to do that. We've caught up to the world. There's no reason we cannot. And oh, by the way, here's where I think the slack is. They're like, oh, that makes sense. Right. So I think I think often your job is to raise ambitions and push in a way where if you push so hard that people always fail, that is a doom loop. Right. And then people are going to start saying, if sure, we'd say yes, Stephen, it won't work. So there's this judgment call of like how far you raise the ambitions. And then what data you be raising those based on, which is usually not the way people think about it. Like usually people will say, here's the amount of work I have to do. And this is how long it'll take. And this is what it means. You look at more macro friends, both inside the company and outside. And based on that, it's more quantitative. Or it's really there's just a one when you're really experienced. This is getting this right. It's a combo of both. Right. It's not knowing that X team is performing better than Y team is really hard to say what is performing better. Yeah, because it's complex. It's complex. But knowing you're getting more output from this team versus this team. And so this team has found some secret. Why can't you raise your other team to the level of this team? That's a gut call. Right. So going, yes, I think the complexity is the same. Yes, I think people on this side might need a little bit of change or need to learn to scale or something. Those are gut calls. There are also obviously you can benchmark externally benchmark internally and go, we did X last year. We did Y the year after. And like industry benchmarks says here's how productivity is increasing. Who in your career has done the best job of this of demanding the most of you. And like what's the story behind it? So again, there's the same. Right. Like as probably taught me an exceptional amount while giving me a tremendous amount of autonomy. What does she teach you? How do you keep raising the bar while being supportive? Zero is globally so complicated. How do you globally scale this way? What excellence looks like outside of product and engineering? What is excellence in marketing? What is excellence in sales? What's excellence in finance? Right. Because here I have someone who is actually an expert in all the demands I'm not in. How are you relentless without tiring our teams up? What do you find very tricky about being a chief product officer? What's really, I keep been doing this for a while. What's really hard about it or maybe if you're not in the seat, you don't quite get it. I think a lot of people would think it is about making a lot of decisions. And I think the more senior you get in any role, especially in the product role, it is about making a few decisions that are big and irreversible. And you need more time to think than to do. And the only way to get there is to have very, very strong returns, which I've been blessed with, I've been able to build up my team to have that, so that you actually don't have to do a lot of the execution. So, like I said, I'm not going to be able to execute my way out or my team is not going to be able to execute their way out of whether what a headless app looks like. That's a deep thinking, you need time. You're not going to be able to execute your way out of what the next genus SaaS app looks like, right? You will do a bunch of experiments in the wrong direction. So I think that's what people think it means more reviewing, more doing. I think it actually, you need to be very focused about which decisions matter and what matters and then spending time on those things. I am famously, I am awful at email because I'm like email is tactical, right? And I am terrible at it. It's not because I run out of time, it's because I'm like, okay, that's today's problem and there are enough people in the org that will solve it. My job is not solving today's small problem. My job is figuring out where we should go in the future. And I think that's a good functioning org and that's not understood very much. I think oftentimes when you step into the role, you go, my job is like actually making sure everything is done. Is it easy for you to figure out what are the decisions that you really have to sit with and wrestle with versus those that should be pushed down? So there are two mechanisms, right? One mechanism is I will push down stuff and then wait and see what feels, okay? Because often if I try to do, I may hold too much, but I'll generally push down stuff and then keep enough of an eye to see if it fails or not. Actually, I'll push down stuff that has impact below a certain amount and not worry about it till somebody escalates. Then there's stuff like this really matters for competitive next year, this set of product we're launching. So we're building tax into you, okay? That really is a big meaty thing that can change our position if we can do integrated tax, closing your books to tax. I'll push it down, but I will make sure I have enough status updates to know when things are going well enough in as light touch away as humanly possible or I've delegated it to a direct that I have a law faith in that is delivered quickly in which case I want to worry about it. I put decisions in three buckets. One is like impact on the business, but like not make a break for the business. Those are delegated down till somebody escalates. Decisions that have big impact on the business, but what you have to do is fairly certain in which case I delegated down, but do keep an eye whether it's by putting a trusted lieutenant that will raise escalate that I trust to catch the issues in escalate or by making sure there's enough status update. And then there are decisions that are just ambiguous. What will the UI have tomorrow look like? Right? That you just can't delegate. So most of my time is spent in the big things that go wrong and even more time is spent on the things that are just ambiguous. You just don't know the answer. How much of a given week or month goes into those big ambiguous? Right now 50% of the month. That's impressive. I feel like great executives would want to do that and then the day to day just gets in the way of that. So I have a trick, right? I do two things. You never respond to an email. It saves you a lot of time. If you respond very quickly, what happens? You get more email. Exactly. Exactly. So like I've all been emailing, I was truly breaking. In many ways, it is bad because I forget like I don't get to urgent emails sometimes, but people know that they can find me on the phone if it's fully urgent, right? But yes, I am notorious at being awful at email and slack, like awful. My trick is the following. So I actually will carve out one full day where I will not do meetings every week. It doesn't matter. I will not do meetings. And you really protect it. I really protect it. And again, like people will tell me I have more flexibility to do that than others, but I will try really hard. The second thing is it is harder in this job, but I also protected at least two hours a day, usually at the end of the day, my brain, I'm a night person. So like I, most of my creative ideas happen like, unfortunately, between nine and 12. It's harder in this job because of the global nature, but I would do that. But that's another thing I do. So like I, and then it's not only about thinking yourself, then it's like you have to bring people into a room. So I, most of my ears laugh because I am militant about my calendar. I can literally militant about what meetings get on my calendar. And I'd say you don't always need 50% right? Like, but right now, if you are not spending 50% of your time thinking about what your product will look like, what a value it will deliver, it's just going to be hard to compete. And you have to be blessed with a great team. I, I, in the last three years, I think I'm at a place where like I can close my eyes and my team can do it down to the heavy lifting on day to day. So when you have this step one is creating the time for it, what do you actually, but let's say on tomorrow, Friday, you have the whole day clear. What are you actually doing to work on these really important, ambiguous problems that at least in your mind are kind of your core job? I won't say I'll make progress and all of it. So at any given time, I think you can go very deep on one. So let's say a new problem because I've been talking about how the Apple changed for while let's say I want to figure out how SaaS business models are changing. So tomorrow, tomorrow, I would go close all the tabs that are open, basically actually switch my browser from Chrome to Safari so that I can't actually get into my word browser and literally go and see like what are people saying about it? Has anybody else done it? What feedback have they gotten? Can I try a product like that? If I were to write down what it would take us to move in that direction, what would I be worried about? What would I not be worried about? What are the risks? So it's really is like just exploring the world outside, exploring the world outside, gathering information, coming in thinking about it, building a structure from where you can have a debate, team the debate up. And maybe you're likely for something like this, you can't debate up in one time. You probably do this for like let's say two, three, four weeks and then you can te a debate up and then it becomes okay. If you've debated it, then you go okay. Now that I've debated with everyone, it's big enough where like I need to give it more structure. So then for the next two, three, four weeks after that will be I'll be giving it structure to render right either a document or a bit of the prototype. Now it's very easy to build a prototype. And then it would be okay. Bring it back. Either at that point you hand it off to someone or if it's still too big, then you take feedback once again, socialize it. That's what you would do. And then when it comes to execution, you're very clear on what has to execute. When you think about the last few years in this category of very big ambiguous problems that you have to solve, what's the one that is like you really nailed? What's the story behind it? And all world example is how does a company like zero compete in the US? This was our head of M&A. How do we compete in the US? It's very clear if we just do it organically, it will take too long. But what is the right bet to make? If you do something in organically, is it to acquire another bookkeeping provider here? Is it to acquire tax provider here? Is it to acquire, what should we do? And I think we bet on we bet on milieu, which everyone knows, we've acquired milieu. And the decision we made which since has proved out to be in retrospect proved out to be an amazing decision. For small businesses, the most important thing is their cash flow. They don't think about accounting. They don't think about, yes, they think about paying people as a requirement. If you could own controlling their cash flow or making them have better cash flow, that I would, in a way that is world class, that would probably be a great way to attract attention and get entry. Invoicing, there are about 100, like AR, there are hundreds and thousands of companies like doing AR. So it's probably not the best place to go to. Bills interestingly enough, even before you incorporate a company or you invoice someone, you do, you pay legal fees, you, you, and tech you might pay to do a prototype somewhere else you may pay for supplies. This is actually interestingly enough the first thing a small business does. So a payments company that is early in the flow of a relationship with small business. And then trying to find a company that had the right tech stack, right, the right founders had the right culture, right, had the right product. Do you find most of the time, that's the case? I think most of the time, it's just, it's not glaringly obvious. I think the big decision. I think the big decisions are not glaringly obvious. And I honestly think like batting averages on big decisions, if every one of the big decisions you take turns out correct, you're doing something very wrong. You're not taking enough risk, something's very wrong. So the batting average again, like I say this, like on big decisions is like, if you're batting averages to thirds, you're probably doing a good job. What was the AI example you were going to share? Everyone around us in our category was doing, was staying away from, they were doing agente actions. The bet we took was agente actions are important. The ability to chat with your app to get financial insights is really important as well. And insights are going to turn, quote unquote, agente as well. In accounting, people were really worried that what if the thing he'll loosen it's any return wrong information. We made a bet early on. We call this our insights product. So financial insights where you literally can go to our chatbot, jacks, our chat, jacks and you can basically do a whole scenario planning. And when we were making the decision, we're like, can you do this at accuracy? What if we make mistakes? What if we misguide people? And I think in retrospect, just going and saying, we're going to do it, we're going to do it at accuracy. And then pushing the teams to do it at accuracy and putting in the scaffolding that was needed for the accuracy, it completely just, one is like, we're ahead in the market. Nobody else does it. Second, and we're at like 95% accuracy or something like in the answers return on. And you can do pretty complicated things like you can go, should I add another shift? Should I buy? Get a loan? Should I buy a car? Like you can do pretty well. Like it's literally like talking to your advisor, but it also helped us just up our AI infrastructure. What I mean by that is how do we do e-vals? How do what do we use for ground truth right like it just because the problem was so hard It just completely changed the game. Do you find that often that if if the if you sort of raise the bar on what you're willing to do It forces a lot of the enabling pieces to come into place. Yes This is why as often as I'm called irrational I'm like no you give human beings something to do and you motivate them to do it will get done You don't way bigger things. We learn how to fly like so We got rockets in space like we've done a lot a bunch of bigger things at a business of your scale How far in the future are you spending most of your cognitive calories? It differs from what it was let's say three years ago to know now things are so uncertain That you're really thinking for months and that's become the future because things are moving so fast and nobody knows Historically you would be laying the groundwork for more than two years out in the future Right, you would be going okay I've set these things that are going to come to fruition in two years and What do I want to do after that? How do I start laying the seeds forward like making the decisions and laying the seeds for what Or needs to happen after that. I think now it's more like how do I lay the seeds to reach a completely different situation in two years How do I start getting the org to execute and oh by the way execute in a very different way to reach a completely different state in two years or 18 months? Do you think given the environment that we're in that that you need just many more bets? Just the total number of bets needs to go up towards more just the nature of what the bets are so saying many more bets is a little dangerous Right because you could do a hundred things today, but do they amount to something? I think today if you have one hypothesis on how the world will work very dangerous if you have I'd say Somewhere around two to four hypotheses over the world will be and then your probabilities on that and then You line up your bets accordingly will apps get more headless? Yes, so like we need to start up Will apps get more agentech almost a certain probability so there should be a bunch of resources on that will apps get more headless Notching completely headless high possibility. So you should have some bets there will Sass apps completely disappear. I Will the workflows disappear? Sass is an overloaded term probably not at least in our category just because it's compliance You need like you need the workflows to prove that you're doing the right thing to submit the taxes as an order trail Do you want a little bit of a bet there? But are you going to put like more than 5% of your 10% of your bet resources? They're probably not but you do want to keep up with the learning so that you can make a pivot as soon as you can Something you only hinted at that we haven't talked that much about is What does it mean to be on an executive team? What does it mean if you're excellent in the capacity of Being a team member on sort of the e-staff of the company and is that any different than you know You have your executive team underneath you is that any different than being world-class as an executive that's underneath you versus this pure set that is running the company When you get to the C staff you are truly holding the Business or the the context one is you need to understand multiple domains at some level of depth to truly have impact Especially as I think especially as a CPU. It's very very hard if you don't understand multiple domains in some ways The second thing I think is you are problem solving you switch between Problem solving in your domain to problem solving at the company level a great example there is I can talk about What air is going to do to the face of an app till I'm blue with my team and believe that's an existential threat But that conversation does not make a ton of sense in depth at the sea level what makes a ton of sense at the sea level is With my peers is like okay, what do we need to do to make our numbers this year? But what do we also need to do to make sure we're there in three years? What does the resource allocation look like oh by the way? What does that mean from a cost perspective? Do we need to go acquire something why in which category so it is it's just different? I think you put on different hats. It's not even altitude. I think you put on different hats In those functions when there's a senior PM that is a star and wants to have a lunch with you or you know Then you have your direct and then in between that you have a director of VP for maybe a few of those different levels What's the advice that you tend to give if they want to eventually be a cheap product officer? I haven't said I want title X ever right the recipe that's worked for me And this is what I tell them I'm like I don't know if you should worry about a title I think if the title happens great, but you should worry about what you want to look back at when you end your career and be proud of and to me It's been a few things which is how do you continue to grow and what makes you continue to grow keep seeking those experiences out Growth by itself is not enough. How are you having impact because impact feels growth? It's just if there's like the more impact you have the more chances you get for growth Yeah, and then work with people that bet on you and will help you grow So that's one one formula I've used and every time I take a new job like it literally is that formula right the second thing is I think people get to stuck in one experience So to the extent you can and this this is why I say don't worry about titles because often you need to go back to go forward Seek out as many different experiences whether that means you're working you do startups mid-size big companies whether you change domains I'm I often get this a lot even if they're not quote trying to climb the ladder, but they're they're Expanding scope and impact are there bottlenecks that you see that that tend to be patterns like that pop up that get people stuck Being able to buy them on high performance from your team often to people feels like You're pushing them too hard and why will they want to work here and why will they want to work for you and you're a bad manager etc etc and that taking the extreme performance management feels very bad and it's a very hard thing for even the best of people to learn I think the second thing that people really struggle with is not knowing everything the more senior you get and How you balance for that and I think the third thing people struggle with is not doing everything So this goes back to the the more senior you get the fewer things you pick as your focus and I think the last thing is As a junior person to you have the most flexibility to car what thinking thinking time I think at the two ends either you're very senior or you're very junior in the middle It's very hard to car what you're on thinking time because you're at the behest of too many people and too many things and too many fires So I think but if you don't do that you can't Invest in having higher impact or your growth sometimes the investment is for your growth sometimes the investments for impact So those are the places where I see people start to sort in each one of those are there do you have a piece of advice or Or or something that can be condensed or is it just too multifaceted? No, I think for the performance stuff like look you build a gut intuition on what's possible and What performance you need and generally your gut intuition is right like demanding Demanding of other people what you would demand of yourself is never a bad thing, right? And then demanding more of yourself is also not a bad thing So so one of my big rules is like if I won't do it, I won't ask people to do it, right? This is why I often get told you do too much and you ask too much and I think the Not having performance in a team is actually detrimental to the whole you won't get the right the whole team won't get the right opportunities You won't retain stars you won't learn from other people than dealing with someone who is not performing well Because even one person can push pull a performance of a team down by 20 20% right because other people are carrying the weight This second one was getting okay with not knowing everything. I think the the advice I give people is and I've had so many people struggle with this Which is like you need to hire people who can do their jobs without you need to hire people who can step into your role in a couple of years And by the way you can learn from today because nobody's immune to learning right and they obviously learn a lot from you But you can learn from them That's the only way you're gonna succeed and Focusing your time on moving the ball forward and bigger things and I think it takes a while for people to get there and it's okay Not to know everything. It's okay to say I have to go ask so and so person as long as it is not as long as you know enough To make sure that things are not a fact thinking time I think look it's hard but like this what I tell people like every company has a rhythm some companies start really fast on Mondays but then Fridays are at store some companies start very slow and Literally run into the weekend some companies actually like slow down in the middle of the week find the thing that works Right like find something that works and try to reinforce it to the best of your abilities And if you don't ask to if you don't tell people that that is the situation people are gonna travel over the calendar This one's easier said than done to be honest, but you have to find a way I when I was a director I literally would call in sick to get my thinking time once in a while because I'm like I just like this is like and I would tell my manager. I'm doing this because you'll respect the fact that I need to get Stuff done and any time to think but like I can't convince the hundred other people so do them. I'm sick Maybe lastly you mentioned this at the very beginning of our convert or maybe it was towards the middle when we're talking about politics The companies what is it that you want your reputation to be multifaceted but honestly known for actually being able to build products at change industry is one and Second build businesses that help like that last for a long time good place to end. Thanks so much for doing this. Yeah, we really appreciate it. It was great