The Exchanges

Q No wonder you look so young. Poor you having to go about that. Um, in terms of the team, so the four team, honestly, it gave me shivers. Like, how do you structure the team now to be much more aligned and cohesive?

A I'll tell you like an ugly little secret here. So like we had 14 teams or 13, I don't know how many there were. And about seven or eight of them got combined into the thing that's now called Shopify core, which is the thing that I run. And part of what we learned in code red was, Hey, these teams aren't aligning and stuff wasn't getting done. And the checkout was getting worse. And so I was like, great, let's put them into this thing called core. So now it's just one team and that will help us align better. And therefore the checkout won't have these problems. And we'll, we won't have this code red thing happen again. Dirty little secret. The day after Toby was like, hey Glenn, cool, you run these eight teams together, these eight teams now, like, please smush them all into one. I was like, great, thank you, and the first thing I did was I split core into eight teams.

AI assessment note: “the first thing I did was I split core into eight teams.”

Q So what would an example be of an assumption?

A Let's go back a few years when, you know, like mobile is on the rise, right? You could see someone building like a mobile product for Shopify, or maybe like a mobile web mode for Shopify, where in the back of their head, they're like, okay, mobile's on the rise. I assume that like all web traffic is going to eventually become mobile, right? And so like the way they're building the product becomes like very extreme because they're like basically all on online shopping is eventually going to be mobile. And another person might have an assumption that's like, hey, I agree mobile's on the rise, but I think it's going to asymptote somewhere around like 60% of all web traffic, which means that 40% is still going to be desktop, which means the desktop's still very, very, very important. And if you, if those two people, if two people on the same team have those two different assumptions, The product that they're going to end up building is going to be wildly different, and they're not going to understand why.

AI assessment note: “I assume that like all web traffic is going to eventually become mobile”

Q Can I ask, what's the most challenging element or segment of this framework? Which is the one that's like, ah, this one's always the fucking hardest.

A The one that is done the least well, is probably, weirdly, the outcomes one, and partly because that's, especially in my team, in core, a lot of what we do in core tends to be fairly low in the stack. So it's like, Like, there are some things at Shopify that are very close to financial results, so they're like, hey, our capital product is really easy to point to, okay, we did this thing and this many more dollars came in, but for many of the core features of, like, a developer platform or a commerce platform, it's really hard to tie, like, oh, we moved this, you know, we made this part of the UX better, and this many more dollars came in, because it's like, it's just like, the web of dependencies is so insane, you can never really unpack it.

AI assessment note: “The one that is done the least well, is probably, weirdly, the outcomes one”

Q What was the biggest, like, oh god, that was hard when building the Shopify app ecosystem? We see it today.

A But what was the big, oh, actually one of the things that we added last year, I would argue has been one of the most insane technical challenges. Um, so we added a thing last year called Shopify functions. The traditional problem with making SaaS platforms extensible is that they're all hosted in the cloud, right? So like Shopify is running its own servers and we're hosting all the websites and all the back offices and whatever. And then if you're an app developer, You really want to be able to, like, we've always given people ways to have their own UI, and that part of it works, but when the third party wants to run its own logic inside of Shopify, we could never really do that because it's insecure, right? It's like, we don't want to take your code and run it on our servers, because what if you're a hacker and he writes something and it gets out and it starts, like, stealing people's data and doing bad stuff, right? So what happens is we ended up having to say, you have to run your code on your servers, but now you have like these horrible performance problems. Cause it's like, you know, our servers are trying to talk to you and everything's just getting slower and it's getting awful. Right? So we released this thing last year called Shopify functions, which leverages a technology called web assembly. And it allows us to take logic written by third party developers compiled d…

AI assessment note: “one of the things that we added last year... one of the most insane technical challenges”

Q What's the biggest weakness? Why are you like, oh God, we need to sort that out?

A I think one of Shopify's challenges today is that we fundamentally do not control the top of the funnel, right? Like the, the top of the funnel for shopping on is something else, right? It's a social media site. It's a news site. It's an ad on Google. It's somewhere else. You know, we're doing a lot of great stuff around Shopify audiences, Shopify buyers. We're doing stuff To help us, like, help our merchants get to the top of the funnel. But at the end of the day, if you don't actually control any part of the top of the funnel, you are always downstream from someone else that you are depending on. And I think that is a fundamental strategic issue that we need to think about.

AI assessment note: “we fundamentally do not control the top of the funnel”

Q So what would an example be of an assumption?

A Let's go back a few years when, you know, like mobile is on the rise, right? You could see someone building like a mobile product for Shopify, or maybe like a mobile web mode for Shopify, where in the back of their head, they're like, okay, mobile's on the rise. I assume that like all web traffic is going to eventually become mobile, right? And so like the way they're building the product becomes like very extreme because they're like basically all on online shopping is eventually going to be mobile. And another person might have an assumption that's like, hey, I agree mobile's on the rise, but I think it's going to asymptote somewhere around like 60% of all web traffic, which means that 40% is still going to be desktop, which means the desktop's still very, very, very important. And if you, if those two people, if two people on the same team have those two different assumptions, The product that they're going to end up building is going to be wildly different, and they're not going to understand why.

AI assessment note: “I assume that like all web traffic is going to eventually become mobile”

Q Can I ask you, you speak about kind of the effect on the world and the product magnitude there. You mentioned kind of, I think it was like the 14 different teams earlier. How do you think about retaining simplicity in product with great depth of customer base and great needs? How do you retain that simplicity?

A I mean, look, in the product itself, there's really only two solutions to, like if you want to do the stretch up thing, which is something we say at Shopify about, like we serve people who are like, you know, it's like literally a 12 year old kid running a lemonade stand up to, you know, like Supreme and like, you know, JB Hi-Fi and like all these insane companies. If you really want to stretch like that, there's very, very, very few pieces of software that have ever adequately served both ends of that market. Um, and The only two pieces of leverage you really have to allow that stretch is one is, um, extremely good execution of progressive disclosure in the core product. So like features that appear at the right time only when you need them. A good example of this is something like, um, like the canonical example of this is like users and permissions management in business software, right? Like when you only got one user, you literally do not need user and permissions management because there's nothing to do, right? So the user permissions management thing being there is like literally making the product worse because there's nothing to do and it's just adding complexity, right? So Part A is progressive disclosure of like what I would describe as anti features, like a feature that makes the product worse by being there because it's not needed yet. And then the second thing, wh…

AI assessment note: “extremely good execution of progressive disclosure in the core product”

Q I'm in. I'm in. Made for a great podcast guest. I do want to, uh, one final question before we do a quick fire. And it's, I think you learn a lot from mistakes that one makes in terms of strategic mistakes. Can you take to a product decision that you made that was a mistake? What did you learn and what was that process?

A There was a mistake strategically underneath Handshake that basically was an ongoing tax for its entire lifetime that I think was a tax that we sort of ended up being, like, pretty tough, and this was misreading what I would call, like, the arrow of progress in, in technology. So when I started Handshake, which was in 2010, and remember I described, like, you know, a lot of it was about working at trade shows, like, you know, sales reps out there on the road, And this is in the era where like LTE and like three G and stuff like just wasn't very good. And so a lot of, um, the use case for handshake was assuming that the person might be offline. Right. And so a huge amount of the tech sack of handshake was built around this fundamental assumption that the user might be offline and you might need to have Basically pre-synced all of the data down to the device that would be necessary for the job to continue to work offline, right? That was actually, like, the killer feature when we launched. Like, when we launched, everyone was, like, mind blown. They're like, I can't believe it. I'm on the basement floor of the Javits Center, and it still works perfectly, and this is the best thing since sliced bread, and it basically, it's huge, like, the combination of leveraging the launch of the iPad, which was in Being excellent at working offline because nobody had iPads that had perfect fiv…

AI assessment note: “There was a mistake strategically underneath Handshake that basically was an ongoing tax”

Q What was the biggest, like, oh god, that was hard when building the Shopify app ecosystem? We see it today.

A But what was the big, oh, actually one of the things that we added last year, I would argue has been one of the most insane technical challenges. Um, so we added a thing last year called Shopify functions. The traditional problem with making SaaS platforms extensible is that they're all hosted in the cloud, right? So like Shopify is running its own servers and we're hosting all the websites and all the back offices and whatever. And then if you're an app developer, You really want to be able to, like, we've always given people ways to have their own UI, and that part of it works, but when the third party wants to run its own logic inside of Shopify, we could never really do that because it's insecure, right? It's like, we don't want to take your code and run it on our servers, because what if you're a hacker and he writes something and it gets out and it starts, like, stealing people's data and doing bad stuff, right? So what happens is we ended up having to say, you have to run your code on your servers, but now you have like these horrible performance problems. Cause it's like, you know, our servers are trying to talk to you and everything's just getting slower and it's getting awful. Right? So we released this thing last year called Shopify functions, which leverages a technology called web assembly. And it allows us to take logic written by third party developers compiled d…

AI assessment note: “has been one of the most insane technical challenges”

Q Can I ask, what's the most challenging element or segment of this framework? Which is the one that's like, ah, this one's always the fucking hardest.

A The one that is done the least well, is probably, weirdly, the outcomes one, and partly because that's, especially in my team, in core, a lot of what we do in core tends to be fairly low in the stack. So it's like, Like, there are some things at Shopify that are very close to financial results, so they're like, hey, our capital product is really easy to point to, okay, we did this thing and this many more dollars came in, but for many of the core features of, like, a developer platform or a commerce platform, it's really hard to tie, like, oh, we moved this, you know, we made this part of the UX better, and this many more dollars came in, because it's like, it's just like, the web of dependencies is so insane, you can never really unpack it.

AI assessment note: “The one that is done the least well, is probably, weirdly, the outcomes one”

Q What's the biggest weakness? Why are you like, oh God, we need to sort that out?

A I think one of Shopify's challenges today is that we fundamentally do not control the top of the funnel, right? Like the, the top of the funnel for shopping on is something else, right? It's a social media site. It's a news site. It's an ad on Google. It's somewhere else. You know, we're doing a lot of great stuff around Shopify audiences, Shopify buyers. We're doing stuff To help us, like, help our merchants get to the top of the funnel. But at the end of the day, if you don't actually control any part of the top of the funnel, you are always downstream from someone else that you are depending on. And I think that is a fundamental strategic issue that we need to think about.

AI assessment note: “we fundamentally do not control the top of the funnel”

Q And you told me so much trash. Before we dive into Shopify, I just have to ask, man, I actually tweeted recently that the best founders I work with have a background in either game design or being exceptional, like, game players themselves. Why do you think game design works? Or being very skilled at gaming leads to very high quality, talented founders.

A That's an interesting question. I mean, I think whether it's video games or, uh, even like traditional games like chess or something like that, I mean, I guess you have to have a very analytical mind and a very competitive mind to like, want to keep basically smashing your head against the wall at the same thing over and over and over and over again. And like getting better and better and better and better at it in a way that's usually very frustrating, but like sort of fun at the same time. And I guess in a way, like founding a company and building a product is an exercise in smashing your head against the wall repeatedly and like only getting better slightly. Right. And then getting a little nibble of cheese every so often that makes you feel good, but mostly an exercise in getting in losing. Right.

AI assessment note: “founding a company and building a product is an exercise in smashing your head”

Q And, and so what makes a good answer, like, a measurable, definable, binary, yes or no?

A Yeah, I mean, look, some things can be measured by numbers. Like, sometimes you can say, hey, I want to take a conversion rate from x to y. I want to take a performance metric from z down to p. Sometimes you can, sometimes the answer is a metric. Not everything is a metric, though. Like, sometimes the answer can be, um, when Toby looks at this page, he's not going to vomit anymore, right? Like, it can be something subjective, because sometimes the work we do is, is really, Aesthetic work. You know, it's, it's like, make this page beautiful. It's goddamn awful right now. So, but, but just being clear upfront on like, like really like, Hey, when you do this project, when we come back six months later and I'll ask you, did it go well, how are you going to answer that question? Like, let's just agree upfront what the format of your answer is going to be. So we all know what we're actually working towards. And you'd be surprised the number of times people don't even know what the answer that is, or people have different answers to what that's going to be.

AI assessment note: “let's just agree upfront what the format of your answer is going to be”

Q Can I ask you, you speak about kind of the effect on the world and the product magnitude there. You mentioned kind of, I think it was like the 14 different teams earlier. How do you think about retaining simplicity in product with great depth of customer base and great needs? How do you retain that simplicity?

A I mean, look, in the product itself, there's really only two solutions to, like if you want to do the stretch up thing, which is something we say at Shopify about, like we serve people who are like, you know, it's like literally a 12 year old kid running a lemonade stand up to, you know, like Supreme and like, you know, JB Hi-Fi and like all these insane companies. If you really want to stretch like that, there's very, very, very few pieces of software that have ever adequately served both ends of that market. Um, and The only two pieces of leverage you really have to allow that stretch is one is, um, extremely good execution of progressive disclosure in the core product. So like features that appear at the right time only when you need them. A good example of this is something like, um, like the canonical example of this is like users and permissions management in business software, right? Like when you only got one user, you literally do not need user and permissions management because there's nothing to do, right? So the user permissions management thing being there is like literally making the product worse because there's nothing to do and it's just adding complexity, right? So Part A is progressive disclosure of like what I would describe as anti features, like a feature that makes the product worse by being there because it's not needed yet. And then the second thing, wh…

AI assessment note: “The only two pieces of leverage you really have to allow that stretch is one”

Q Well, I mean, there were skills and challenges. I just thought I would admit the challenges and be more polite. I'm British, you know, we're charming. Um, but so my question to you was, what works and what doesn't in how you run product? Teams. I know it's blunt and bland, but I do just want to stop there.

A Well, I can tell you what people would have said doesn't historically, but I think it's become, at least at Shopify, I think we've embraced this style of leadership a bit more in the last few years, which is, we have this thing inside of Shopify now called, and when this first was released, I was like, this sounds so stupid, but I've actually come to really excel, like, appreciate it. Have this idea of, like, aiming, assembling, and achieving. Aiming is, like, deciding, like, Here's the direction we're going in. Here's what we're doing, right? Assembling is like, you could think of it as like the operational part. Like how do we get the people, the resources, the timing, the meetings, blah, blah, blah, blah, blah, to actually do this. And then the achieving is the actual doing. It's like coding, designing, whatever, like actually doing the work to do the thing. I would say my style of leadership and Toby's and Kaz's, and I would say this is actually common to basically all of the leadership at, uh, at Shopify now is The willingness to be a senior aimer, where you say, I think the product should be this, and like, I insist we go in this direction. Which is, if we're being honest, like over the past 10 years, this sort of was a, the flavor of the month was like, sort of bottoms up everything, like empower, like power to the edges, like whatever you want to describe that thing as.…

AI assessment note: “The problem with power to the edges and bottoms up decision making”

Q And you told me so much trash. Before we dive into Shopify, I just have to ask, man, I actually tweeted recently that the best founders I work with have a background in either game design or being exceptional, like, game players themselves. Why do you think game design works? Or being very skilled at gaming leads to very high quality, talented founders.

A That's an interesting question. I mean, I think whether it's video games or, uh, even like traditional games like chess or something like that, I mean, I guess you have to have a very analytical mind and a very competitive mind to like, want to keep basically smashing your head against the wall at the same thing over and over and over and over again. And like getting better and better and better and better at it in a way that's usually very frustrating, but like sort of fun at the same time. And I guess in a way, like founding a company and building a product is an exercise in smashing your head against the wall repeatedly and like only getting better slightly. Right. And then getting a little nibble of cheese every so often that makes you feel good, but mostly an exercise in getting in losing. Right.

AI assessment note: “founding a company and building a product is an exercise in smashing your head”

Q I love that. Actually, that was your second, and then third was, how did that come to be?

A Yeah, so at the end of twenty-twenty, um, the Code Red was wrapping up, and, you know, Checkout was in a much better place, and actually one of the things that Um, one of the things that was sort of instructive for both Toby and me in that Code Red was that, like, the, the previous, and, and this is, this sort of gets to, like, Conway's Law and, like, org chart shipping, and, you know, this is a thing that all PMs eventually, like, run into and, like, gnash teeth at, but the old org structure of Shopify, uh, like, 20, 20, and, and maybe for the three or four years trailing was that there was something like, I think there was something like 12 or 13, uh, Um, different, what we called product lines, which are basically divisions. And each one had their own full stack, like product engineering, UX data, everything. And they all had their own little part of the product they're responsible for. And it turned out that one of the reasons that the checkout got into so much trouble was that a lot of the fundamental problems that existed in the checkout required multiple of these divisions to collaborate. Because again, like the checkout kind of bridges like everything in Shopify. And so when you have this org that's cut all these lines, it suddenly gets really hard to coordinate solutions that bridge the lines, right?

AI assessment note: “at the end of twenty-twenty, um, the Code Red was wrapping up”

Q And the cheese is called secondary. So tell me, so the handshake comes to beef, um, you and Mike, and then what happens? You get a, you get acquired by Shopify, what happens?

A Right, so yeah, Mike and I built, I mean, we'll fast forward nine years, so we built the company, uh, you know, and ups and downs for nine years, it was a great experience, um, you know, obviously we learned a ton. Towards 2018, 2019, we got to know some of the folks at Shopify. Shopify was in this zone where it was kind of towing around the edges of, like, starting to do some wholesale stuff. We were, like, Like specialists in only doing wholesale, um, e-commerce. And then it just kind of came to be that it was like, hey, let's, let's do this. Let's get together. One plus one equals two, or I mean, a thousand plus one equals 2000, whatever you want to phrase it. But yeah. And then, so since I've been at Shopify, I've basically had three roles since I've been here. My initial role was just doing the wholesale thing. Did that for about the first year. Um, and that was for the most part running the handshake team within Shopify. Um, And then I spent the first year of the pandemic in 2020 moving over to run checkout. So that was a year in which there was some really fundamental things in the checkout that needed to be fixed, like rather promptly. And so Toby asked me to move over and basically like run a, what's called a code red on checkout. And that code red went.

AI assessment note: “Towards 2018, 2019, we got to know some of the folks at Shopify.”

Q And, and so what makes a good answer, like, a measurable, definable, binary, yes or no?

A Yeah, I mean, look, some things can be measured by numbers. Like, sometimes you can say, hey, I want to take a conversion rate from x to y. I want to take a performance metric from z down to p. Sometimes you can, sometimes the answer is a metric. Not everything is a metric, though. Like, sometimes the answer can be, um, when Toby looks at this page, he's not going to vomit anymore, right? Like, it can be something subjective, because sometimes the work we do is, is really, Aesthetic work. You know, it's, it's like, make this page beautiful. It's goddamn awful right now. So, but, but just being clear upfront on like, like really like, Hey, when you do this project, when we come back six months later and I'll ask you, did it go well, how are you going to answer that question? Like, let's just agree upfront what the format of your answer is going to be. So we all know what we're actually working towards. And you'd be surprised the number of times people don't even know what the answer that is, or people have different answers to what that's going to be.

AI assessment note: “let's just agree upfront what the format of your answer is going to be”

Q Not at all, but I want to start with a little bit on you. So how did you make your way into the world of startups first? And then come to lead the product door at Shopify today.

A I've had a winding and weird career that just looks stupid on paper, but, um, I, uh, I was a comp sci grad, I, I was a video game developer for three or four years, um, I ended up in San Diego, uh, basically one of my high school teachers asked me to move to the States and run, like, the US warehouse of his, him and his wife's eco-friendly shopping bag business. Which was, I was like, I want to move to the U S let's do this. And so I ended up in, in San Diego in a warehouse with forklifts whizzing around me and, you know, that kind of stuff. And I was like, I was a video game developer a second ago, what just happened? Um, and as part of that business, which did a lot of wholesale business, I ended up going to a lot of trade shows in New York and being on the floor of the Javits center. And, you know, I would be writing orders in these order books for like, when, you know, people would come to the booth and say, I want to Have your bags in my store. And so after doing a bunch of these trade shows, I kept thinking, well, there should be an iPhone app for entering these orders. This writing orders in books thing is like a nightmare. And so after a while there was no, I just kept thinking someone would build an iPhone app for this and it just kept not happening. And so after a couple of years of that, I was just like, fuck it. I'll just, you know, I'll just download the X code. I'…

AI assessment note: “I built a prototype of what eventually became handshake, which is just literally an iPhone app”

Q And the cheese is called secondary. So tell me, so the handshake comes to beef, um, you and Mike, and then what happens? You get a, you get acquired by Shopify, what happens?

A Right, so yeah, Mike and I built, I mean, we'll fast forward nine years, so we built the company, uh, you know, and ups and downs for nine years, it was a great experience, um, you know, obviously we learned a ton. Towards 2018, 2019, we got to know some of the folks at Shopify. Shopify was in this zone where it was kind of towing around the edges of, like, starting to do some wholesale stuff. We were, like, Like specialists in only doing wholesale, um, e-commerce. And then it just kind of came to be that it was like, hey, let's, let's do this. Let's get together. One plus one equals two, or I mean, a thousand plus one equals 2000, whatever you want to phrase it. But yeah. And then, so since I've been at Shopify, I've basically had three roles since I've been here. My initial role was just doing the wholesale thing. Did that for about the first year. Um, and that was for the most part running the handshake team within Shopify. Um, And then I spent the first year of the pandemic in 2020 moving over to run checkout. So that was a year in which there was some really fundamental things in the checkout that needed to be fixed, like rather promptly. And so Toby asked me to move over and basically like run a, what's called a code red on checkout. And that code red went.

AI assessment note: “hey, let's, let's do this. Let's get together... since I've been at Shopify”

Q No wonder you look so young. Poor you having to go about that. Um, in terms of the team, so the four team, honestly, it gave me shivers. Like, how do you structure the team now to be much more aligned and cohesive?

A I'll tell you like an ugly little secret here. So like we had 14 teams or 13, I don't know how many there were. And about seven or eight of them got combined into the thing that's now called Shopify core, which is the thing that I run. And part of what we learned in code red was, Hey, these teams aren't aligning and stuff wasn't getting done. And the checkout was getting worse. And so I was like, great, let's put them into this thing called core. So now it's just one team and that will help us align better. And therefore the checkout won't have these problems. And we'll, we won't have this code red thing happen again. Dirty little secret. The day after Toby was like, hey Glenn, cool, you run these eight teams together, these eight teams now, like, please smush them all into one. I was like, great, thank you, and the first thing I did was I split core into eight teams.

AI assessment note: “the first thing I did was I split core into eight teams.”

Q Well, I mean, there were skills and challenges. I just thought I would admit the challenges and be more polite. I'm British, you know, we're charming. Um, but so my question to you was, what works and what doesn't in how you run product? Teams. I know it's blunt and bland, but I do just want to stop there.

A Well, I can tell you what people would have said doesn't historically, but I think it's become, at least at Shopify, I think we've embraced this style of leadership a bit more in the last few years, which is, we have this thing inside of Shopify now called, and when this first was released, I was like, this sounds so stupid, but I've actually come to really excel, like, appreciate it. Have this idea of, like, aiming, assembling, and achieving. Aiming is, like, deciding, like, Here's the direction we're going in. Here's what we're doing, right? Assembling is like, you could think of it as like the operational part. Like how do we get the people, the resources, the timing, the meetings, blah, blah, blah, blah, blah, to actually do this. And then the achieving is the actual doing. It's like coding, designing, whatever, like actually doing the work to do the thing. I would say my style of leadership and Toby's and Kaz's, and I would say this is actually common to basically all of the leadership at, uh, at Shopify now is The willingness to be a senior aimer, where you say, I think the product should be this, and like, I insist we go in this direction. Which is, if we're being honest, like over the past 10 years, this sort of was a, the flavor of the month was like, sort of bottoms up everything, like empower, like power to the edges, like whatever you want to describe that thing as.…

AI assessment note: “The willingness to be a senior aimer, where you say, I think the product should be this”

Q setting is, like, not making them gameable. I've, uh, you know, I, I realized this last week when, you know, with my investment team, I was like, we need to meet 20 companies a week. Well, they, you could meet 20, anyone can meet 20 companies a week, but you just, like, meet your corner shop. That's a company. Do you know what I said? Like, they have to be.

A This is the, this is the marketing is red, sales is green problem. Like, that I used to have at Handshake, which is, One other thing, I mean, sorry, we're getting off product now, but like, one of the things that like you, you, you always seen, you often see in go to market organizations is that because sales and marketing people are very like goal oriented and like in often compensated on the numbers, they really want numbers that they're in control of. Like they really want the number that they're going to be paid on to be a number that they actually control. And so this, this leads marketing teams to want to declare goals that are about like The marketing funnel, but not the bottom of the sales funnel, which is exactly what you just said, like, oh, I met 20 people this week. Well, were 19 of them homeless? Like, you know what I mean? It doesn't, it doesn't.

AI assessment note: “which is exactly what you just said, like, oh, I met 20 people”

Q I love that. Actually, that was your second, and then third was, how did that come to be?

A Yeah, so at the end of twenty-twenty, um, the Code Red was wrapping up, and, you know, Checkout was in a much better place, and actually one of the things that Um, one of the things that was sort of instructive for both Toby and me in that Code Red was that, like, the, the previous, and, and this is, this sort of gets to, like, Conway's Law and, like, org chart shipping, and, you know, this is a thing that all PMs eventually, like, run into and, like, gnash teeth at, but the old org structure of Shopify, uh, like, 20, 20, and, and maybe for the three or four years trailing was that there was something like, I think there was something like 12 or 13, uh, Um, different, what we called product lines, which are basically divisions. And each one had their own full stack, like product engineering, UX data, everything. And they all had their own little part of the product they're responsible for. And it turned out that one of the reasons that the checkout got into so much trouble was that a lot of the fundamental problems that existed in the checkout required multiple of these divisions to collaborate. Because again, like the checkout kind of bridges like everything in Shopify. And so when you have this org that's cut all these lines, it suddenly gets really hard to coordinate solutions that bridge the lines, right?

AI assessment note: “one of the reasons that the checkout got into so much trouble was that”

Q And Marika told me that you're an exceptional storyteller. How do you think about telling that story to the team as to why you made the decision and why they should follow you?

A This storytelling thing was beaten into me, like, almost as an existential threat when I was, like, trying to raise money at Handshake. I had this, like, let me spend a couple of minutes here because I think it's worth it. Like, the, I was a member of a CEO peer group. When I was running Handshake, and this is when we were coming up, we had done our Series A, we're on the way to the Series B, and I was a member of a CEO peer group that met in San Francisco. I was from New York, so I'd fly out there once every three months and do the meetings, and I went to the first meeting, and one of the guys in the, most of the guys in the peer group were CEOs of tech companies or biotech companies, but one of the guys in the, in the group was the, uh, the managing partner of a VC fund, and his name is Phil. And on the first one of these meetings, each founder got up and like did the little pitch for their business. And I got up and I was like, yeah, it's handshaking. It's wholesale. And like, there's these sales reps and there's these businesses and they need to like trade. And like, it's a huge problem. And we've got this mobile app and blah, blah, blah, blah, blah. And I told my whole thing. And I think most people in the room were like, oh, we totally get it. Like, you know, we see the business thing here. And at the dinner that evening, Phil kind of like sat down next to me at the dinne…

AI assessment note: “This storytelling thing was beaten into me, like, almost as an existential threat”

Q And Marika told me that you're an exceptional storyteller. How do you think about telling that story to the team as to why you made the decision and why they should follow you?

A This storytelling thing was beaten into me, like, almost as an existential threat when I was, like, trying to raise money at Handshake. I had this, like, let me spend a couple of minutes here because I think it's worth it. Like, the, I was a member of a CEO peer group. When I was running Handshake, and this is when we were coming up, we had done our Series A, we're on the way to the Series B, and I was a member of a CEO peer group that met in San Francisco. I was from New York, so I'd fly out there once every three months and do the meetings, and I went to the first meeting, and one of the guys in the, most of the guys in the peer group were CEOs of tech companies or biotech companies, but one of the guys in the, in the group was the, uh, the managing partner of a VC fund, and his name is Phil. And on the first one of these meetings, each founder got up and like did the little pitch for their business. And I got up and I was like, yeah, it's handshaking. It's wholesale. And like, there's these sales reps and there's these businesses and they need to like trade. And like, it's a huge problem. And we've got this mobile app and blah, blah, blah, blah, blah. And I told my whole thing. And I think most people in the room were like, oh, we totally get it. Like, you know, we see the business thing here. And at the dinner that evening, Phil kind of like sat down next to me at the dinne…

AI assessment note: “This storytelling thing was beaten into me, like, almost as an existential threat”