Shopify's VP Product on Why the Founder is Always the Head of Product

Yeah. I’ve had a winding and weird career that just looks stupid on paper. I was a CompSci grad. I was a video game developer for three or four years. I ended up in San Diego. Basically, one of my high school teachers asked me to move to The States and run, like, The US warehouse of him and his wife’s eco friendly shopping bag business, which was I was like, I wanna move to The US. Let’s do this. And so I ended up in in San Diego in a warehouse with forklifts whizzing around me and that kind of stuff.

And I was like, I was a video game developer a second ago. What just happened? 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. I would be writing orders in these order books for, like, when people would come to the booth and say, I wanna have your bags in my store. And so after doing a bunch of these trade shows, I kept thinking there should be an iPhone app for entering these orders.

This writing orders in books thing is like a nightmare. After a while, I just kept thinking someone would build an iPhone app for this, and it just kept not happening. After a couple of years of that, I was just, fuck it. I’ll download Xcode. I’ll learn Objective C. Haven’t coded in a couple years. Let’s go. And I built a prototype of what eventually became Handshake, which is just literally an iPhone app for entering waters at a trade show. I moved to New York around the same time, and then I basically applied to go to business school, went to business school, went for one day, and then I was like, actually, this is not what I wanna be doing.

I’d actually rather be coding twelve hours a day. And so I quit business school, and then Handshake just happened, and that’s where I my old friend, Mike Elmgreen, came on board as my cofounder to run sales and marketing. I think you met Mike and he’s probably told you all the trash about me.

That’s an interesting question. I guess you have to have a very analytical mind and a very competitive mind to want to keep basically smashing your head against the wall at the same thing over and over and over again and getting better and better and better at it in a way that’s usually very frustrating but fun at the same time. And I guess in a way, founding a company and building a product is an exercise in smashing your head against the wall repeatedly and 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 losing.

is

So, yeah, Mike and I built I mean, we’ll fast forward nine years. So we built the company, and then, yeah, towards 2018, 2019, we got to know some of the folks at Shopify. Shopify was in this zone where it was towing around the edges of starting to do some wholesale stuff. We were specialists in only doing wholesale ecommerce. And then it just came to be that it was like, hey. Let’s do this. Let’s get together. Yeah. And then so since I’ve been at Shopify, I’ve 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, and that was for the most part running the Handshake team within Shopify. 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 rather promptly. And so Tobi asked me to move over and basically run a what’s called a code red on checkout. That code red went the code red?

Code red is everyone drop everything. This is the most important project. If the people running this project ask you to do something on their project instead of what you’re already doing, please do it.

Yeah. So at the end of twenty twenty, the Code Red was wrapping up, and checkout was in a much better place. One of the things that was constructive for both Toby and me in that Code Red was and this is this sort of gets to, like, Conway’s Law and, like, org chart shipping, and this is a thing that all PMs eventually run into and gnash teeth at. But the old org structure of Shopify 2020 and maybe for the three or four years trailing was, I think, it was something like 12 or 13 different what we called product lines, which are basically divisions.

And each one had their own full stack 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, checkout kind of bridges, like, everything in in Shopify. And so when you have this org that’s cut on all these lines, it suddenly gets really hard to coordinate solutions that bridge the lines.

Right?

Yeah. There we go. What does that mean? Do you mean a framework other than just being an opinionated asshole? Preferably, yes. Or an Australian. Those are synonyms. You know that. Yeah. Look, I do my best. I think at some level, you can’t reduce product to frameworks because if you could, we wouldn’t have you know, and it’s just one of those things where at its base, product management is making good decisions about what to build and when. At some level, you can’t just reduce that to frameworks, but you do want to reduce the amount of wasted work that just goes in the trash can, which is wasteful.

It’s frustrating. It’s shit. Everyone hates it. One of the things that I encourage teams at Shopify to do, especially in Core so Core is now about half of all in r and d in Shopify. Core is what the outside world would think of as the built in bits when you sign up for Shopify. So the stuff you get in the box, it’s the online store, the checkout, all of the back office, all those bits, that’s core, and that’s about half of the r and d team, is what I currently oversee product for.

And so you can imagine there’s a lot of teams in there. And then, like, at any given time, there could be a thousand projects running. Can’t look at all of them. Can’t dive into all of them. So the framework that I try to have people think about, I like to ask people to sketch out your outcomes, your assumptions, and your principles at the start of a project because these are the places where things can go off the rails, and it’s really good to catch those things early because you can just find, oh, let’s get ahead of this because you’re gonna go off in the wrong direction here.

Yeah. What’s No. No. No. Let’s let’s start with outcomes because it’s probably the easiest. Outcomes is how do we know this is gonna go well? When this is all done, you’re telling me you wanna run this project, and it’s gonna take 10 engineers for six months. At the end of this, how are we gonna know that it was worth it? It’s a really easy question, and you’d be surprised how often teams do not have an answer to this question. So what makes a good answer, like, a measurable, definable,

Yeah. Look. Some things can be measured by numbers. Sometimes you can say, hey. I wanna take a conversion rate from x to y. I wanna take a performance metric from z down to p. Sometimes the answer is a metric. Not everything is a metric, though. Sometimes the answer can when Tobi looks at this page, he’s not gonna vomit anymore. It can be something subjective because sometimes the work we do is really aesthetic work. It’s make this page beautiful. It’s goddamn awful right now. But just being clear upfront on really, hey, when you do this project, when we come back six months later and I ask you, did it go well, how are you gonna answer that question?

Let’s just agree upfront what the format of your answer is gonna 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 to that is or people have different answers to what that’s gonna be. Okay. So that’s outcome. Next. Principles are probably the most difficult and counterintuitive, but principles are basically how are we gonna make the very hard decisions, the fifty one forty nine decisions that reasonable people could take either side of in this project.

We can anticipate that there are gonna be some forks in the road in here, and reasonable people might take either side. And as a team, we all wanna go into one side. We don’t wanna do this thing where half of us are pulling in one direction, of us are pulling in the other. Principles tend to be things like I’ll give you a good example. So, obviously, at Shopify, we serve primarily three constituents. The merchants who run their business on Shopify, developers who build apps and themes on Shopify, and then the buyers who are buying from Shopify stores.

We have these three constituents that are always circling. So a principle you might put into a project would be something in the cases where the interests of merchants and developers conflict, we are going to break for merchants every time. Right? Now, different people might take reasonably either side of that argument, but it’s really bad if half the team is taking one side and half the team is taking the other. When you can see that a project is gonna have these conflicts in it, it’s good upfront to say, hey.

When we hit this fork in the road, we’re all going left so that the team doesn’t just split in half and start destroying itself.

Very, very often. Especially at the scale Shopify exists at. It’s often the case that you have to trade off against, and it’s not always between those three constituents. You might even have trade offs between small merchants and large merchants. Like, how do we think about the needs of very small businesses and so the trade offs can vary, but once your businesses make commerce better for everyone, everyone, pretty big word, and the interests within everyone tend to conflict quite a bit, and so you do need to anticipate these conflicts and try to get ahead of them.

And then what was the third? Assumptions. This is often where I get into these very funny conversations with Tobi where we’re, like, railing at each other about two. I’m like, I can’t believe you wanna do this. It is it’s insane to me that you wanna do that. And then we get into the bottom of the conversation, and what we realize is that we have some foundational assumption about reality that’s different, which explains why we are are talking past one another. So what would be an assumption?

Let’s go back a few years when mobile is on the rise. Could see someone doing 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 all web traffic is gonna eventually become mobile. The way they’re building the product becomes very extreme because they’re like, basically, all on online shopping is eventually gonna be mobile. And another person might have an assumption that’s, hey, I agree mobile’s on the rise, but I think it’s gonna asymptote somewhere around 60% of all web traffic, which means that 40% is still gonna be desktop, which means desktop’s still very, very important.

If two people on the same team have those two different assumptions, the product that they’re gonna end up building is gonna be wildly different, and they’re not gonna understand why. What’s

done the least 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. There are some things at Shopify that are very close to financial results, sort of, 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 a developer platform or or a commerce platform, it’s really hard to tie, like, oh, we made this part of the UX better, and this many more dollars came in because it’s just like the web of dependencies is so insane.

You can never really unpack it. I think

have This is the marketing is red, sales is green problem that I used to have at Handshake, which is one of the things I’m sorry. We’re getting off product now, but No. It’s good. One of the things that, like, you often see in go to market organizations is that because sales and marketing people are very goal oriented and often compensated on the numbers, they really want numbers that they’re in control of. They really want the number that they’re gonna be paid on to be a number that they actually control.

This leads marketing teams to want to declare goals that are about the marketing funnel, but not the bottom of the sales funnel, which is exactly what you just said. Oh, I met 20 people. Were 19 of them homeless?

Exactly. And this is when you get into the weird parts in businesses where, oh, god, the marketing’s doing great, but sales is doing terrible. What’s going on? Or like, marketing and sales are doing amazing, but customer success seems to be really struggling.

Yeah. I think the closer you are to the bottom of the stack, the more responsibility you have to build for the future. There’s basically a direct relationship between like, in a platform that has, like, primitives, APIs, going all the way up to the user facing features in the apps, the closer you are towards the bottom of the stack, you really need to be thinking about the long term future. It’s actually one of the things that I’ve learned. And when you’re in a startup, you have a bias towards thinking towards basically on a one to two year time frame because that’s how much cash you have.

And one of the super refreshing things about being at Shopify has been actually, two things. Because Toby’s had basically a fifteen year bull run of it’s been hard, but he’s mostly been an outrageously successful technologist. He has built up this immense muscle memory for being like, I’m always thinking to five to ten years out on where’s the Internet gonna be and what’s gonna happen to the world of trade and like that. He’s awesome at ten years, and he’s awesome at what can we do this week.

Whereas, like, people like startup founders who are more like, man, we’re always trying to get to the next round, we’re really trained on this one to two year hamster wheel of what we need to do in the next one to two years. And so one of the things I had to learn at Shopify was understanding when you build APIs, when you build new primitives, when you build things into the base layer of a platform that has millions of merchants, tens of thousands of developers, When you make those fundamental changes, how is it gonna reshape the world of the Internet and trade for the next two, three, four, five years in a way that you don’t think about at startups?

Because at startups, you don’t have 10% of Internet ecommerce running on you. And I think Sadly not. Right? And this is like, you know, when Apple makes a decision like, hey, we’re gonna change ITP and ATT. It’s like you change one little thing that because it’s so close to the bottom of the stack, it literally reshapes the entire planet. That’s when you have to be thinking about the long term because of the effect it’s gonna have on the world.

Look, in the product itself, there’s really only two solutions to if you wanna do the stretch up thing, which is something we say at Shopify about we serve people that’s, like, literally a 12 year old kid running a lemonade stand up to, like, Supreme and JB Hi Fi and, like, all these insane companies. If you really wanna stretch like that, there’s very few pieces of software that have ever adequately served both ends of that. And the only two pieces of leverage you really have to allow that stretch is one is extremely good execution of progressive disclosure in the core products, so features that appear at the right time only when you need them.

The canonical example of this is, like, users and permissions management in business software. Right? When you only got one user, you literally do not need user management because there’s nothing to do. So the user and permissions management thing being there is literally making the product worse because there’s nothing to do, and it’s just adding complexity. Part a is progressive disclosure of 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, which is probably the bigger piece of leverage, is an app platform and an app ecosystem.

Apps can be built on top. They extend the platform with functionality that doesn’t have out of the box. But the really critical thing here is you need two things, and they’re actually basically conjoined at the hip. You need an app platform that allows apps to be built that are of equal quality to the core features of the platform. That is absolutely critical. Look at iOS. IOS is, like, a great example of this.

Like, when I open up a first party app like Messages, and I open up a third party app like Spotify or Lyft or something, the third party apps are as good quality as the first party apps because they’re all built on the same toolkit, and Apple made the tools available such that third party apps could be as good as the first party apps. This strategy does not work if the third party apps are all trash, and it’s only the first party apps that are actually good.

But if you have an app platform that basically gives the same tools to third party developers that the first party ones have, then you enable this rich ecosystem of actually high quality apps that allow the large enterprises to scale up because they add apps as they need them, but the core product stays simple for the people who don’t need that yet, which is again just part of that stretching. I guess apps in a way are a form of progressive disclosure. Can I ask, Glen? Yeah.

Actually, one of the things that we added last year, I would argue, has been one of the most insane technical challenges. So we added a thing last year called Shopify Functions. What’s the best way to describe this? The traditional problem with making SaaS platforms extensible is that they’re all hosted in the cloud. 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, 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? We don’t wanna take your code and run it on our servers because what if you’re a hacker and you write something and it gets out and it starts stealing people’s data and doing bad stuff. So what happens is we ended up having to say, you have to run your code on your servers, but now you have these horrible performance problems because it’s our servers are trying to talk to you, everything’s just getting slower and it’s getting awful.

We’ve released this thing last year called Shopify Functions, leverages a technology called WebAssembly. It allows us to take logic written by third party developers, compiled down to this thing called WebAssembly, which we can run-in secure environments that are safe on our servers. And now we have this magical best of both worlds thing, which is we can take third party code, and we can run it on our servers. So we’re getting the third party code, but we’re getting all the performance benefits as if Shopify wrote it ourselves.

And now you get this perfect harmony benefits of fully hosted SaaS platform, but also the benefits of fully third party applications. And that was a very difficult thing to overcome. As far as I’m aware, Shopify was the first at scale SaaS platform to do that. And that’s been a problem in SaaS and software forever until last year. So that was really difficult, that one.

Yeah. I’ll we don’t. I’ll tell him, like, an ugly little secret here. We had 14 teams, 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. You gotta go take a shot now. These eight teams were not aligning, and stuff wasn’t getting done, and the checkout was getting worse. And so it’s 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 won’t have this Code Red thing happen again. Dirty little secret, the day after Toby was like, hey, Glen. Cool. You run these eight teams together. Please smush them all into one. Was like, great. Thank you. And the first thing I did was I split core into eight teams. Why? Because you need an org chart. You need a way of organizing teams together in same sizes that can actually work together.

Of course, it does. But the Dunbar number is the Dunbar number, which is the number of people that anyone can reasonably deal with without having a brain aneurysm. There’s just a physical limit on how many people. Core is about two and a half thousand people. There’s now 10 of these teams inside core, so there are about 200 people each, which is about the Dunbar number, which is not a coincidence. But here’s the thing. In the old org structure, the first point in the org chart where all those 14 teams actually joined at the top was Tobi.

So anytime someone has an escalation, the first point in the escalation tree was Tobi. He’s a public company CEO. That’s not a reasonable expectation for someone like Tobi to have to take on. The thing that works better now than it did before is that there’s a team including me, my head of design, my head of engineering, head of data, head of product marketing. We sit above these 10 teams, but we consider our jobs to be understanding what’s going on in these teams, handling the escalations, making sure that when kid a and kid b both wanna go to university, we’re like, you know what?

You get to go in university. You get to be happy. You get to be sad. But the good news is no one’s confused about what we’re doing. And in the old world, teams could be at odds for six months, they’d be like, I wanna do this. And they’d like, I wanna do that. They’d be like, are we escalating to Tobi? And it’s like, I don’t know. And then you just sit there for six months, and it’s frustrating.

Stop there. I can tell you what people would have said doesn’t historically, but 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. And when this first was released, I was like, this sounds so stupid, but I’ve actually come to really appreciate it. I have this idea of aiming, assembling, and achieving. Aiming is deciding, here’s the direction we’re going in. Here’s what we’re doing. Assembling is you could think of it as the operational part.

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 coding, designing, whatever, doing the work to do the thing. I would say my style of leadership and Tobi’s and Kaz’s, and I would say this is actually common to basically all of the leadership at Shopify now, the willingness to be a senior aimer where you say, I think the product should be this, and I insist we go in this direction, which is, if we’re being honest, over the past ten years, this sort of was a the flavor of the month was bottoms up everything, power to the edges, whatever you wanna describe that thing as.

But the problem with power to the edges and bottoms up decision making, the value of a product like Shopify, not even a product, like a product suite, because Shopify has many products. And look at Apple. The Apple is like the Mac, the iPhone, the iPad, the watch, the everything. The value of that suite is to a large extent the way it all works beautifully together. And if all the decisions are coming from the edges, the chance that it’s all gonna work together and feel like it came from pen of a single creator just goes through the floor.

And that’s what makes using an iPhone and an iPad such an amazing experience is that it really does feel like it all came from the hand of a single creator, and you need at some point for there to be a single hand on the wheel in order for that to be true.

Oh, I don’t think they don’t move down the field quite as fast, but there is a difference between moving downfield at 80% speed and literally digging your heels in. Yeah. Have you had problems there? I’ve had problems there. But it’s fine. I’ll do it, and it’s done shitty. Yes. For sure. Sometimes that’s a problem with the person who’s disagreeing and not really committing, and maybe they just have to say, I disagree with this way of running a company. I disagree with this product direction. I should just leave the company.

Sometimes it’s a failure of the leadership to explain why they’re aiming in a particular direction. I think saying we’re going over here and just fucking do it is quite different than saying we’re going over here. Here’s why. Let’s do this together.

This storytelling theme was beaten into me almost as an existential threat when I was trying to raise money at Handshake. I was a member of a CEO peer group while I was running Handshake. We had done our series a. We’re on the way to series b. And I was a member of a CEO peer group that met in San Francisco. 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 most the of guys in the peer group were CEOs of tech companies or biotech companies.

But one of the guys in the group was the managing partner of a VC fund, and his name was Phil. And on the first one of these meetings, each founder got up and did the little pitch for their business. And I got up and I was like, yeah, it’s Handshake, it’s wholesale, and there’s these sales reps, and there’s these businesses, and they need to trade, and it’s a huge problem, and we’ve got this mobile app and blah blah blah blah blah. I told them my whole thing.

And I think most people in the room were like, oh, we totally get it. We see the business thing here. At the dinner that evening, Phil sat down next to me, and he was like, hey, man. Tell me the story. And I was like, I did tell you the story. And he’s like, man, tell me the story. Tell me something that I can feel. And I was like, oh, yes. This wholesale thing, and there’s the truck lifts, and there’s the FedEx trucks, and there’s the iPads, and there’s the order books, and blah blah blah.

No. Dude. Tell me a story. And he beat me into the ground over I don’t know. I must have sat there with him for an hour with him just being like, just tell me the story over and over and over again. And I eventually got to a story. I literally ended up making it up on the spot. I was like, you know when you go into a store and you walk in there looking for a particular thing, you want a white t shirt in a particular size, and you go to the shelf where that shirt should be, and it just isn’t there, and it should be there.

That is literally what we are doing. We help the companies with the shirts make sure that they get to the right stores in the right time, so that when you get to the store, the shirt that you expect to be on that shelf is actually there, and just multiply that by all the people in the world and all the shelves in the world and all the number of times that you’ve gone there and it’s not been there. That’s what we’re solving. That’s not even a very good story.

But finally, Phil was like, I get it. I could explain that to my mom, and she’d actually understand what you did. Since then, I’ve just understood that if you do not tell someone a story that they can see themselves in and they can empathize with, You can say all the numbers in the world. You can describe all the processes and analysis in the world. No one gives a shit. No one’s got time for your shit. I really try to encourage people to find a way to tell the story.

Humans are emotional creatures. If you can’t get me to feel something, I’m probably not gonna care no matter how many numbers you throw at me. Totally do.

The best stories work for everyone. They don’t make two versions of Aladdin. There’s one version of Aladdin. Great stories work. Until you can get there, you’re not really doing your job.

I don’t actually know what the answer to this is because I think this is another one of those things that if there was an answer, everyone would be an amazing storyteller. I think people can tell when you, the speaker, actually feel the thing. It’s just like the passion and the enthusiasm that you tell the story with. And Do you make sense which are random relatable?

a story you don’t feel? I can’t. That’s one of my problems is that sometimes people give me scripts to read, and I’m like, I’m not gonna read this bullshit because if I did, you would hate how I would read it because everyone would know I didn’t mean it.

you’d be shocked how fast people forget things. This is why compelling storylines with just memorable sound bites are so important, because you only get to lodge, like, a few words in someone’s brain before every word you add pops one out their other ear. And you only get to choose maybe three words you can lodge in someone’s brain at any given point in time, and you really need to choose what they are. Do think

tell me. What do you think Shopify does based on just the words that you just read? I think it’s just a bit bland. Isn’t it? It’s bit boring. That’s It’s on the transcript of this to I want it empowerment.

That sounded pretty good.

Dude, I totally agree. I think our.com could be a lot better. I’m not gonna trash it too hard right now. By the way, I do this with a lot of people, and I’ve never ever had anyone who’s been like, no. Actually, it’s great. Yeah. No. Look, I think software product marketing is an insanely difficult thing to do. So I loved the message you just delivered. One of the hard things that happens when you get Shopify scale, which is not an excuse, but it’s a thing that is a fact, is that Toby’s had the mission of Shopify to make commerce better for everyone for a long time.

But if you cycle back five years, what everyone actually meant was mostly pretty small businesses, mostly selling fashion, mostly in North America. Shopify today is actually getting a lot close to actually everyone and coming up with a message that resonates for all countries, all sizes of business, all industries, online, offline, all the stuff, you do eventually start to hit the problem you’re describing. And again, I agree with you. The blandness does tend to seep in because you’re like, gotta talk to everyone. You get into how do you market tied kind of problems.

And with you

Supreme and MrBeast are actually examples of people who I think your message would land with. It’s not so much them. It’s more like legacy risk averse retail is the group. It’s like Sears is gonna come like, they’re gonna see the message you just said, and they’re gonna be like, maybe we should go to Salesforce. That feels a bit more safe. Feels like they’re probably gonna give us some nice brochures. Maybe that’ll feel better. This Or are they actually gonna be listening to Toby’s quarterly report and going, this guy hard thing.

This isn’t you’re getting to the true art of product marketing, which is how do you have a message which still speaks authentically to who you are and what you actually give a shit about without alienating an unacceptably large part of your customer base. And this is the art.

managing? The thing that is important to state as a fact here is that Tobi, like all great CEO founders, is actually the head of product at Shopify and will always be. I think the day that Toby’s not running a product at Shopify is the day that he’s not at Shopify. I run half of product, but I don’t run all of product. The part of the product that I run has a specific focus that I think would be diluted if I had to take on more. I could, but I’d be less good at the part that I do, and the part that I do is pretty fucking important.

The part of Shopify that I run is really the platform part, and there are other parts of Shopify, namely shop and Shopify logistics, which are more aggregator plays. And I think the strategy and execution of platform businesses and aggregator businesses are fundamentally different. The best businesses are the ones that can actually do both and find the touch point between both. It’s actually part of why I find working at Shopify so exciting right now is because the aggregator part of Shopify shop has now reached such critical mass that the things that we can do by combining the shop buyer base with the Shopify core platform are starting to become exponentially valuable versus what either of those two things can do individually.

And by the way, basically, all of our competitors are just pure platforms, which is why these days, not to toot our own horn, but these days, I’m like, I’d be fucking terrified to be competing with Shopify in commerce. We have a great platform, but we’ve got it joined at the hip to an incredible buyer aggregation engine, which it’s hard to overcome how powerful that is. Does Shopify compete with

That’s a great question. 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 ended up being pretty tough. This was misreading what I would call the arrow of progress in technology. So when I started Handshake and remember I described a lot of it was about working at trade shows, sales reps out there on the road. This is in the era where LTE and three g and stuff just wasn’t very good. And so a lot of the use case for Handshake was assuming that the person might be offline.

A huge amount of the tech stack 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. And so that was actually, like, the killer feature when we launched. 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 a huge the combination of leveraging the launch of the iPad, which was in 2009, I think, and being excellent at working offline because nobody had iPads that had perfect five g at the time. That was the killer feature, and that catapulted our growth for probably the first two, three, four years of the company. But then eventually, LTE was everywhere. Five g was everywhere.

All the convention centers had Wi Fi. All the stores on the road had Wi Fi. Internet’s everywhere now. And so suddenly, we’ve now got this feature, which actually isn’t that valuable because there’s basically Internet everywhere. And we’ve got an insane amount of technical debt sitting in the product that is specifically designed to cope with offline situations. We basically hit an inflection point where it’s like, okay. Now we’re not innovating as fast because we’ve just got this immense amount of tech debt that governs everything we do, and we’ve got a feature that increasingly no one gives a shit about.

By misreading if you’d said to me in 2010, hey, Glen, how long do you think it’s gonna be until there’s literally Internet connectivity everywhere? I might have actually sat down and thought, k. How long is that really gonna be, and how should I think about building platform that knows that is coming in whatever I would have guessed, three years, four years, five years? I never really had that conversation with myself, and I put a check-in the mail that had a huge bill in it that we were ultimately never able to pay down.

That’s a stressful moment. Refreshation.

wow, true user delight, and why? Oh. Sorry. Nerdy example, but this is my drum kit, the Roland v drum kit. You would not believe how incredible the way this thing works is, the way the response is on cymbals and the drum heads, and it’s shocking how well this thing emulates the feel of a real drum kit. Head versus heart, what wins? In the end, heart, which is bad for me because I’m basically a head guy. Ideal relationship between CEO and VP product. The relationship between the lead singer and the drummer in a band just jamming together all the time.

As the founder, if you ever say the words like this other person is the head of product, you just quit your job.

You started a company and you’re explicitly, I’m the business guy founder and this other guy is the product guy founder, fine. But if you are a product founder like Tobi look. Let’s be honest. Most of the very, very successful tech companies, the founder is the product person. The minute that person says this other person is the head of product, they’ve done one of two things. They’ve either quit their job, or they have given that other person a title that everyone knows is bullshit, and they’ve basically given that person’s a death sentence.

Don’t sit on the fence, mate. What is Shopify’s biggest strength today? As a company, I would say it’s that we have at pretty significant scale. There’s 10,000 people in the company. I would say we are moving in terms of actual innovation and shipping. We are moving as fast as I’ve seen any other company of this scale. Just go and look at the additions that we just put out. The number of features that we put out in this edition and the previous edition just six months ago.

It’s all there in black and white. I don’t think anyone can step to us in terms of how much we’re actually putting out right now. And then as a product, would say, it’s the thing that I said a second ago. It’s a product that has an incredible built in user experience for the merchant. It has a developer platform that is becoming every month an incredible developer experience and, like, really powerful, that this is the critical thing. It’s a platform that is joined at the hip to an aggregator pool that is rapidly becoming the most powerful buyer population on the Internet, and it’s the combination of the platform success and the aggregator success that makes it literally unstoppable.

weakness? Why are you like, oh, god. We need to sort that out. I think one of Shopify’s challenges today is that we fundamentally do not control the top of the funnel. Right? The top of the funnel for shopping 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. We’re doing a lot of great stuff around Shopify audiences, Shopify buyers. We’re doing stuff to help us 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.

That is a fundamental strategic issue that we need to think about. The alliance that is a recession proofness. Like, when you have consumer demand down in a recession, obviously, global trade It’s direct access to your audience. It’s why Sam Harris can say stuff, and you can’t cancel Sam Harris because he literally maintains direct control to his audience at all times. That’s a different situation to be in.

the world of product? PMs are not gonna like it when I say this.

I wish PMs would be a little bit less fixated on the process and technique of PM ing as a craft and just focus a little more on am I making good decisions? Do I do what I say I was gonna do? Do I work well with the people that I work with? And do I get shit done? At the end of the day, the job isn’t actually much harder than that. It’s do you make smart decisions? Do you get shit done? Good? Great.

And I worry a little bit that PMs sometimes get very navel gazey about what the art and science of being a PM is to the point where I’m like, hey, can you just go do some work and just be good at your job and make great decisions and ship products and make people happy? I find

Exactly. Exactly. The best PMs have this feeling about them where it’s like a freight train that, like, if you try and stand in front of this thing, you’re gonna get fucking flattened. The best PMs have this sense of, I’m building this thing. It’s gonna be great. Stand in front of me at your fucking peril. Let’s go.

Sorry. This is such a boring answer because literally everyone would give it, but the way Microsoft is going at the AI thing is brilliant. Why do you think so? They correctly picked years ago that partnering with OpenAI would be at least strategic. Lots of people knew that AI would be the thing. But the thing that they are doing right now with Bing and AI driven search is that they are basically correctly realizing that Bing is a dead thing. Bing’s dead, and they’ve literally got nothing to lose.

And they’ve got a business that is completely defensible in other revenue streams, like Office and Windows and and all the other stuff they do. Search is like a non part of their business, but search is everything to Google. Like, if search ads stop working, Google is not a thing anymore. They are swinging for the fences with a completely novel approach, which might not work, but if it works, basically completely alters the business of one of their competitors and creates a business for them that could be really compelling.

And if it doesn’t work, who gives a shit? Bing was dead anyway. Man, you’re my fucking hero. Have loved the show.