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Glen Coates: Why Shopify Will Dominate Amazon; How Microsoft Made Smartest Move of 2023 | E986

Glen Coates is the VP of Product @ Shopify, leading the development of Shopify’s core commerce platform. He also oversees the core developer platform and Shopify’s partner ecosystem, which includes over 10,000 publicly available apps in the Shopify App Store. Originally a CompSci grad, Glen moved from Sydney to San Diego in 2008 to run US distribution and e-commerce for an Australian eco-products company. In 2010, he attended Columbia Business School for one whole day before quitting to start Handshake, a SaaS B2B e-commerce platform. Glen joined Shopify in May 2019 when the company acquired Handshake. Glen has been in the Vice President role since October 2020. --------------------------------------------- Timestamps: 0:00 How Glen Made His Way into The World of Product 7:02 Glen’s Product Framework 15:00 How To Set Product Goals 22:03 Hardest Part of Building Shopify’s App Ecosystem 27:06 Lessons on Team Management 31:00 What Makes Exceptional Storytelling and Messaging 42:30 How to “Manage Up” and Shopify’s Competition with Amazon 45:36 Biggest Product Mistake 48:50 Quick Fire Round ----------------------------------------------- In Today’s Episode with Glen Coates We Discuss: 1. From Game Developer in Sydney to Running E-Commerce Warehouse in NYC: How Glen made his way into the world of product and e-commerce having started life as a game developer? Why does Glen believe that the best founders and product people often have their roots in gaming? What does Glen know now that he wishes he had known when he joined Shopify? 2. The Art of Product and Product Management: Is product more an art or a science? If you had to put a number on it, what would it be? What is “product management”? Why can it not be reduced to frameworks? What are “product principles”? How do Shopify use them? How should product teams set them? What makes the very best PMs today? What are the commonalities in them? What is the sign of a poor PM? What would Glen most like to change about the world of PMs? 3. The Art of Product Marketing: What does Glen believe is the true art of product marketing? How did a CEO group teach Glen how to tell truly great stories? How can one tell great stories when you have to cater to multiple different customers/personas? How does Glen evaluate the current state of Shopify’s product marketing? 4. Shopify and The Future of Shopify: Why does Glen think it is important for Shopify to have a tops down decision-making process for product strategy? What does Glen believe is the #1 reason why Shopify is such a large and successful company? What is the single hardest element of Glen’s role today? How does Glen believe that Shopify will be larger than Amazon in 5-10 years time? --------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Glen Coates on Twitter: https://twitter.com/glencoates Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com ------------------------------------ #GlenCoates #Shopify #HarryStebbings #VPproduct #productmanager #productmanagement

Harry StebbingshostGlen Coatesguest
Mar 8, 202356mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 7:02

    How Glen Made His Way into The World of Product

    1. HS

      The things that you love can be funded by Shopify technology. We make your life and your dreams possible.

    2. GC

      That sounded pretty good.

    3. HS

      Glenn, I am so excited for this. I've heard so many great things from your love of pad thai to your learning the drums.

    4. GC

      (laughs)

    5. HS

      I'm... Uh, this is just gonna be a fun show, so thank you-

    6. GC

      Yeah.

    7. HS

      ... so much for joining me, man.

    8. GC

      Uh, yeah. Happy to be here, man. Thanks for having me.

    9. HS

      Not at all. But I wanna start with a little bit on you. So, how did you make your way into the world of startups first, and then come-

    10. GC

      Mm-hmm.

    11. HS

      ... to lead the product org at Shopify today?

    12. GC

      I've had a winding and weird career that just looks stupid on paper. But, um...

    13. HS

      (laughs)

    14. GC

      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 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, you know, that kinda 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 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, "Well, there should be an iPhone app for entering these orders." These writing orders in books thing is like a nightmare. And so after a while, there was no... I, I just kept thinking someone would build an iPhone app for this, and it, it just kept not happening. And so after a couple years of that, I was just like, "Fuck it. I'll just, you know, I'll just download the Xcode." 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 orders at a trade show. I moved to New York around the same time, and then I... What happened? I basically applied to go to business school, went to business school, went for one day, and then I was like, "Actually, this is kind of not what I wanna be doing. I'd actually rather be coding 12 hours a day." And so I quit business school, and then I, and then Handshake just happened, and that's where I... You know, my old friend Mike Elmgreen came on board as my co-founder to run, um, uh, to run sales and marketing. I think you met Mike, and he's probably told you all the trash about me. Um, yeah.

    15. HS

      Well, then, and y- he told me so much trash. Before we dive into Shopify-

    16. GC

      Yep.

    17. HS

      ... I just have to ask, man.

    18. GC

      Yeah.

    19. HS

      I, 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.

    20. GC

      Mm-hmm.

    21. HS

      Why do you think game design or being very skilled at gaming leads to very high-quality, talented founders?

    22. GC

      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, (clears throat) I mean, I guess you have to have a very analytical mind and 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?

    23. HS

      Yeah, for sure.

    24. GC

      (clears throat)

    25. HS

      And the cheese is called secondary. (laughs)

    26. GC

      (laughs) Yeah.

    27. HS

      Um, so, so tell me. So, the Handshake comes to be, um-

    28. GC

      Yep.

    29. HS

      ... you and Mike, and then what happens? You get, uh, you get acquired by S- Shopify? What happens?

    30. GC

      Right. So, yeah, Mike and I built... I mean, um, 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 kinda toeing around the edges of, like, starting to do some wholesale stuff. We were, like, specialists in only doing wholesale, um, e-commerce. And then it just kinda 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 2,000 (laughs) , whatever you wanna phrase it, but 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, um, 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, the- 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-

  2. 7:02 – 15:00

    Glen’s Product Framework

    1. HS

      And I heard that-

    2. GC

      (laughs) .

    3. HS

      ... you have this product framework to ensure you build the right products with the-

    4. GC

      Yeah.

    5. HS

      ... least amount of misalignment. (laughs)

    6. GC

      Yeah.

    7. HS

      There we go. Um, what does that mean?

    8. GC

      D- Do you mean a, a, a framework other than just being an opinionated arsehole?

    9. HS

      Preferably, yes.

    10. GC

      Right.

    11. HS

      Or an Australian. (clears throat)

    12. GC

      (laughs) Those are synonyms.

    13. HS

      (laughs)

    14. GC

      You know that, right?

    15. HS

      Yeah.

    16. GC

      Um, um, look, look, I do my best. I mean, I think at, at some level, you can't reduce product to frameworks, because if you could, like we wouldn't have jo-... You know what I mean? It's just one of those things where at, at its, at its base, product management is making good decisions about what to build and like what to build and when.

    17. HS

      Mm-hmm.

    18. GC

      And 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 like wasteful, it's frustrating, it's shit, everyone hates it. One of the things that I have encouraged teams at Shopify to do, especially in core, so like core is now about half of all our R&D in Shopify, right? And core is what the outside world would think of as like the built-in bits when you first, when you sign up for Shopify. So, like the stuff you get in the box, it's like the online store, the checkout, all of the back office, all those bits, that's core, and that's about half of the R&D team, which is what I, I currently oversee product for. And so you can imagine there's a lot of teams in there.

    19. HS

      (laughs)

    20. GC

      Like at any given time, there could be like 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 is I like to ask people to sketch out like 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 like find, oh, let's, let's get ahead of this 'cause you're gonna go off in the wrong direction here.

    21. HS

      Can we actually take an example? So, outcomes, assumptions, principles.

    22. GC

      Sure.

    23. HS

      How, how would we do one of those? I'm sorry for the naive question.

    24. GC

      Yeah, yeah.

    25. HS

      What's an example?

    26. GC

      L- Let's, let's start with outcomes, 'cause it's probably the easiest.

    27. HS

      Mm-hmm.

    28. GC

      Outcomes is like, how do we know this is going to go well? Like when this is all done, like you're telling me you want to run this project, so it's going to take 10 engineers for six months. At the end of this, how are we gonna know that it was worth it, right? It's a really easy question, and like often, you'd be surprised how often teams do not have an answer to this question.

    29. HS

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

    30. GC

      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 gonna vomit anymore, right? Like, it, it can be something subjective because sometimes the work we do is, i- 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 ask you, 'Did it go well?' How are you gonna answer that question?" Like, 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.

  3. 15:00 – 22:03

    How To Set Product Goals

    1. HS

      thing that I've learned actually on like objectives and goal setting is like not making them gameable. Uh, I've s-

    2. GC

      Yeah.

    3. HS

      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-

    4. GC

      Yeah.

    5. HS

      Any... You could meet 20 comp- Anyone can meet 20 companies a week, but you're just like-

    6. GC

      No.

    7. HS

      ... meet your corner shop.

    8. GC

      No.

    9. HS

      As a company (laughs) . Do you know what I say? Like they have to see-

    10. GC

      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-

    11. HS

      No, it's great.

    12. GC

      ... one of the things that like you, you, you always see and y- and 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 gonna be paid on to be a number that they actually control.

    13. HS

      Yeah.

    14. GC

      And so this w- 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 it doe-... You know what I mean? It doesn't-

    15. HS

      I-

    16. GC

      It doesn't...

    17. HS

      I to- I totally get you and it's like-

    18. GC

      Yeah.

    19. HS

      But even if you have it on like converted dollars or acquisition, it's not-

    20. GC

      Yeah.

    21. HS

      ... tied into retention. You could just-

    22. GC

      Exactly.

    23. HS

      ... nab everything to get them over the line, then be shittier quality leads that churn after two months, but you've actually hit your numbers.

    24. GC

      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?" You know? Or like, "Marketing and sales are doing amazing, but customer success seems to be like really struggling. What's up with that?" You know?

    25. HS

      Can I, can I ask you, you mentioned there about kind of being close to the finances in the products that we build.

    26. GC

      Yeah.

    27. HS

      How do you... And this is a really tough one I find with products. How do you balance in terms of product decision-making between what's generating revenue today and innovation for the future?

    28. GC

      I think the closer you are to the bottom of the stack, the more responsibility you have to build for the future. I mean, it's just like, there's basically a direct relationship between... Like in a, in a platform that has like primitives, APIs, going all the way up to like the user-facing features in the apps, like 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. When you're in a startup, you have a bias towards thinking towards like basically on a one to two-year timeframe because that's how much cash you have.

    29. HS

      Yeah.

    30. GC

      And one of the super refreshing things about, um, being at Shopify has been actually two things. One is because Tobi is... Because Tobi's had basically a 15-year bull run of like... I mean, he's ha- it's been hard, but he's mostly been an outrageously successful technologist.

  4. 22:03 – 27:06

    Hardest Part of Building Shopify’s App Ecosystem

    1. GC

      disclosure.

    2. HS

      Can I ask, Glen-

    3. GC

      Yeah.

    4. HS

      ... what was the biggest like, "Oh God, that was hard," when building the Shopify app ecosystem? We see it today, but what was the big (groans) ?

    5. GC

      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 'cause it's insecure, right? It's like we don't want to take your code and run it on our servers 'cause what if you're a hacker and you write 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 re- released this thing last year called Shopify Functions, which leverages a technology called WebAssembly. And it allows us to take logic written by third-party developers, compiled down to this thing called WebAssembly, which we can run in like secure environments that are safe on our servers. And now we have this like magical best of both worlds thing, which is like 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 like perfect harmony of the benefits of like a fully hosted SaaS platform but also the benefits of like fully third-party applications. And that was a very, very difficult thing to overcome and I- I'm- as far as I'm aware, Shopify was the first at-scale, um, SaaS platform to, to do that. And that's been a, that's been a problem in, in, in SaaS and, and software forever until last year. So like that, that was really difficult, that one.

    6. HS

      No wonder you look so young. Poor you having to build that.

    7. GC

      (laughs)

    8. HS

      Um, I- in terms of the teams, like the 14 honestly, it gave me shivers. Like-

    9. GC

      Yeah.

    10. HS

      ... how do you structure the team now to be much more aligned and cohesive?

    11. GC

      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, Glen. Cool. You run these eight teams together, the eight, 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.

    12. HS

      Why?

    13. GC

      Because, well, you need an org chart. You need a way of organizing teams together in sane sizes that can actually work together.

    14. HS

      But if you make them into eight teams, surely that creates silos. It creates barriers of communication, information slippage. Like-

    15. GC

      Of course it does. But like, the Dunbar number is the Dunbar number, right? Like, which is the number of people that anyone can, like, reasonably deal with without having, like, a brain aneurysm, right? So, there's just a physical limit on how many people. So like, just so you know, Core is about, uh, two-and-a-half thousand people, right? 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, like, joined at the top, was Toby. So, anytime someone has an escalation, the first point in the escalation tree was Toby. Which if, you know, he's a public company CEO. Like, that's not a reasonable expectation for someone like Toby to have to take on. So, 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 are actually, like, we consider our jobs to be understanding what's going on in these teams, handling the escalations, making sure that like, you know, when kid A and ki- kid B both wanna go to university, we're like, "Do you know what? You get to go to university. You don't. You have to, you get to be happy, you get to be sad." But the good news is, is no one's under any... No one's confused about what we're doing. And in the old world, pe- confusion used to just sit there for like, you know, teams could be at odds for like six months and they'd be like, "Well, I wanna do this." And they'd be like, "Well, I wanna do that." And they'd be like, "Well, are we escalating to Toby?" And it's like, "Ah, I don't know. I don't know if we should do that." And then you just sit there for six months and it's like, frustrating.

  5. 27:06 – 31:00

    Lessons on Team Management

    1. GC

    2. HS

      Glen, I want to ask you about kind of team management in particular because I heard so many different elements about your leadership skills. What works and what doesn't? (laughs)

    3. GC

      Was skills in quote marks or was that, was it, was it clean?

    4. HS

      Well, I mean, there were skills and challenges. I just thought I would omit the challenges and be more polite. I'm British, you know?

    5. GC

      (laughs)

    6. HS

      We're charming. Um, but, so my question to you is what works and what doesn't in how you run product teams? I know it's blunt and bland, but I do just wanna start there.

    7. GC

      Mm-hmm. 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 Caza'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 there, 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. But the problem with power to the edges and bottoms up decision-making is that the value of a product like Shopify, or the value, uh, not even a product, like a product suite. Like, 'cause Shopify has many products, right? And look at Apple, right? Like, 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.

    8. HS

      Yeah.

    9. GC

      Right? And if all the decisions are coming from the edges, the chance that it's all gonna work together and like feel like it came from the, the, the pen of a single creator just goes w- like, goes through the floor, right? 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, the hand of a single creator. And you, you need at some point for there to be a single hand on the wheel in order for that to be true.

    10. HS

      My friend can I ask, do you agree with disagree and commit?

    11. GC

      I do, yeah.

    12. HS

      You think people will disagree and commit in the same way as if they agreed?

    13. GC

      Oh, I don't think they... Uh, they don't move down the field quite as fast.

    14. HS

      Yeah.

    15. GC

      But there is a difference between moving downfield at 80% speed and like literally digging your heels in.

    16. HS

      Yeah. Okay. Have you had problems-

    17. GC

      Yeah.

    18. HS

      I've had problems there where it's like, "Fine, I'll do it." And it's like done shittily and you're like, "Fuck's sake."

    19. GC

      Yeah. I mean, I'm sure I have.

    20. HS

      (laughs)

    21. GC

      I'm sure that I've had those pro- I know I have. I mean, I, I... Yes. For sure. And I think that's, sometimes that's a, a, a problem with the person who's disagreeing and not really committing.

    22. HS

      Yeah.

    23. GC

      And maybe they just have to say...... "I disagree with this way of running a company, I disagree with this product direction, and I should just leave the company." Um, (clears throat) sometimes it's a failure of the leadership to explain why they're aiming in a particular direction. Like, I think saying, like, "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."

    24. HS

      Well, I, I think there's two things here, and I want to ask you about both of them. It's like, the how and the why.

  6. 31:00 – 42:30

    What Makes Exceptional Storytelling and Messaging

    1. HS

      And I think-

    2. GC

      Yeah.

    3. HS

      ... why is the storytelling. And-

    4. GC

      Yeah.

    5. HS

      ... Maica 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?

    6. GC

      This storytelling thing was beaten into me, like, almost like as an ex- existential threat when I was, like, trying to raise money at Handshake. I had this, like... Let me spend a couple of minutes here 'cause 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, 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 was 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 Handshake and 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 dinner and he was like, "Hey man," he's like, "tell me the story." And I was like, "I did tell you the story." And he's like, "No, no, no, man. Tell me the story. Tell me something that I can, like, feel." And I was like, "Oh, yeah, it's 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." You know, and he was like, "No, no, dude. Tell me a story." And he beat me into the ground over, like... I don't know, I, I must have sat there with him for an hour with him just being like, "No, no, no, just tell me the story," over and over and over and over again. And I eventually got to a story that was... 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, and 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." And I've... Since then, I've just understood that I'm like, if you do not tell someone a story that they can see themselves in and they can, like, 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. And so, like, I really, really, really try to encourage people to find a way to tell the story. Like, humans are emotional creatures. And, like, if you can't get me to feel something, I'm probably not gonna care no matter how many numbers you throw at me. You know?

    7. HS

      I totally do. H- f- before you touch on like, that, the, uh, how in terms of the communication-

    8. GC

      Yeah.

    9. HS

      ... what do you do if you have two different personas? Say you have the customer and the retailer. The story may differ. Do you see what I mean? The pain is different.

    10. GC

      Yeah.

    11. HS

      What do you do then if you're storytelling? Do you just have different messages for different personas?

    12. GC

      You can, but I mean, at, at the end of the day, like, you, you, you really do need to... You, you need a story that... You want s- ... The best stories work for everyone, right? Like, they don't make two versions of Aladdin. There's one version of Aladdin. And like, you just... You know? Great stories work. And I, I just think until you can get there, you're not really doing your job.

    13. HS

      And how do you say that, then, to your team? Like, is it stand up at an all-hands and say, "Oh, you know that feeling when you go into the store and there's no T-shirt?" (laughs)

    14. GC

      Um, yeah. H- how do I tell the story to my team?

    15. HS

      Yeah. How do you imbue that to them and make them feel it?

    16. GC

      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, like, everyone would be an amazing storyteller. I think people respond to authenticity in stories. I think people can tell when you mean it. Like, I think people can tell when you, the speaker, actually feel a thing. Um, and yeah, I, I, I think it's just, like, the passion and the enthusiasm that you tell the story with, and-

    17. HS

      W- would you ever tell a story-

    18. GC

      ... the extent to which you made it relatable.

    19. HS

      Would you ever tell a story you don't feel?

    20. GC

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

    21. HS

      (laughs) Yeah. I totally get that. Can I... In terms of the communication, how do you-

    22. GC

      Yeah.

    23. HS

      ... make... I think a lot of founders struggle with the repetition, but-

    24. GC

      Mm-hmm.

    25. HS

      How important is repetition in storytelling and-

    26. GC

      All the time.

    27. HS

      All the time?

    28. GC

      All the time. You need to keep saying that the... Like, you'd be, uh, you'd be shocked...... how fast people forget things. Like, you need- this is why compelling storylines with just, like, memorable, memorable soundbites are so important, 'cause you get- you only get to lodge, like, a few words in someone's brain before, like, every word you add pops one out their other ear. And you only get to choose, like, 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.

    29. HS

      Do you think startups tell good stories? I think when it comes to product marketing, I'm always horrified at the state of product marketing. I'm just like-

    30. GC

      Yes.

  7. 42:30 – 45:36

    How to “Manage Up” and Shopify’s Competition with Amazon

    1. HS

      that, uh, you were exceptional and had an uncanny ability to manage up. What do you-

    2. GC

      Hmm.

    3. HS

      ... think he meant by this, and- and how do you think about managing up?

    4. GC

      Well, I mean, the- the thing that is important to state as a, uh, 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 Tobi's not running a pr- product at Shopify is the day that he's not at Shopify. You know, I run half of product, but I don't run all of product.

    5. HS

      Would you like-

    6. GC

      So, my job... Sorry?

    7. HS

      Would you like to?

    8. GC

      I don't think it would be, uh... So, 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 mean, I- I could, but I'd- I'd be less good at the part that I do, and the part that I do is pretty fucking important (laughs) . Um, and- and what I'm really getting at there is, like if you, if you ............................ you know, about like platform aggregator theory? The- 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 one- the best businesses are the ones that a- can actually do both and find the touch point between both. And that's why- 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 like 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 like 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, I mean, 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. Not- we have a great platform, but like we've got it joined at the hip to an incredible buyer aggregation engine, which is just hard to, it- it's hard to overcome how powerful that is.

    9. HS

      Does Shopify compete with Amazon in five years?

    10. GC

      Well, I mean, Shopify competes with Amazon today.

    11. HS

      But like in terms of scale and magnitude, like-

    12. GC

      Oh, absolutely. 100%. 100%.

    13. HS

      (laughs) You're still a founder, Glen (laughs) .

    14. GC

      (laughs)

    15. HS

      I love this.

    16. GC

      Gi- gi- gi- give me, just say like, "Hey, there's a war over there." I'm gonna be like, "Great."

    17. HS

      Let's ............................ (laughs)

    18. GC

      Yeah (laughs) .

    19. HS

      Made for a great podcast guest, uh... (laughs)

    20. GC

      (laughs)

    21. HS

      Hey, I do wanna, uh, one final question before we do a quick fire. And it's-

    22. GC

      Yeah.

    23. HS

      ... I think

  8. 45:36 – 48:50

    Biggest Product Mistake

    1. HS

      you learn a lot from mistakes that one makes in terms of strategic mistakes. Can you take-

    2. GC

      Mm.

    3. HS

      ... me through a, a product decision that you made that was a mistake? What did you learn and what was that process?

    4. GC

      There was a mistake strategically underneath Handshake that basically was an ongoing tax for its entire lifetime that I- 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 3G 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 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, right?

    5. HS

      Got you.

    6. GC

      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, a huge, like 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 5G 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. 5G was everywhere. All the convention centers had wifi. All the stores on the road had wifi. Ev- like internet's everywhere now. And so suddenly, we've now got this feature which actually isn't that valuable because like 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. And so we basically kind of hit an inflection point where it's like, okay, now we're not innovating as fast because we've just got this i- immense amount of tech debt that governs everything we do. And we've got a feature that increasingly no one gives a shit about. And so by misreading, like if you, if you'd said to me in 2010, "Hey Glen, um, how long do you think it's gonna be until there's literally internet connectivity everywhere?" I might have actually sat down and thought, "Okay, how long is that really gonna be? And how should I think about building a platform that knows that that is coming in, whatever I would have guessed, three years, four years, five years?" I never really had that conversation with myself. And so I ended up causing a, I put a check in the mail that had a huge bill in it that we were ultimately never able to pay down.

    7. HS

      Oh, that's a stressful moment (laughs) .

    8. GC

      (laughs)

    9. HS

      Sheesh. Fucking hell.

    10. GC

      (laughs)

    11. HS

      (laughs) My friend, I wanna do a quick fire round. So, I say a short statement, you give me your immediate thoughts. Does that sound okay?

    12. GC

      Hit me.

  9. 48:50 – 56:09

    Quick Fire Round

    1. GC

    2. HS

      So, what was the last product that made you go, "Wow"? Like, true user delight, and why?

    3. GC

      Sorry, nerdy example, but this is my drum kit, like the Roland V-Drum kit. You would not believe how incredible, like, the way this thing works is. Like, the way the response is on cymbals and the drum heads and, like ... It's- it's shocking how well this thing emulates, like, the feel of a real drum kit.

    4. HS

      Head versus heart, what wins?

    5. GC

      In the end, heart, which is bad for me 'cause I'm basically a head guy.

    6. HS

      (laughs) Ideal relationship between CEO and VP product?

    7. GC

      Like the relationship between the lead singer and the drummer in a band, just, like, jamming together all the time.

    8. HS

      What's the biggest mistake that founders make when hiring product teams?

    9. GC

      (laughs) I don't think founders should ever say that y- ... As the founder, if you ever say the words, like, "This other person is the head of product," you just quit your job.

    10. HS

      Why? That- that- because you could have a sales-led founder. You don't ha- ... Like, you know, if you're an enterprise product, you-

    11. GC

      Fair. If you, if you started a company and you were explicitly like, "I'm the business guy founder and this other guy is the product guy founder," fine. But like, if you are a product founder, like Tobi, and like ... Look, let's be honest. Most of the very, very successful tech companies, the founder is the product person.

    12. HS

      Yeah.

    13. GC

      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 a death sentence.

    14. HS

      (laughs) Don't sit on the fence, mate. Uh. (laughs)

    15. GC

      (laughs)

    16. HS

      Uh, what is Shopify's biggest strength today? If you were to say the one reason why Shopify is fucking stellar, what would it be?

    17. GC

      As a company, I would say it's that we have, at pretty significant sale- ... Scale. There's 10,000 people in the company right now. I would say we are moving, in terms of, like, actual innovation and, like, shipping, we are moving as fast as I've seen any other company of this scale. Like, just go and look at the editions that we just put out. Like, the number of features that we put out in this edition and the previous edition just six months ago, like it's all there in black and white. I don't think anyone can step to us in terms of how much, like, we're actually putting out right now. And then as a product, I would say it's the thing that I said a second ago. It's- 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 dev- developer experience and, like, really powerful. And, but 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, like, literally unstoppable.

    18. HS

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

    19. GC

      I think one of Shopify's challenges today is that we fundamentally do not control the top of the funnel.

    20. HS

      Hmm.

    21. GC

      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.

    22. HS

      I think also it, it aligns that it's like the recession-proofness, like when you have consumer demand down in a recession, obviously global trade ... (exhales) 8:10.

    23. GC

      I mean, this is- it's like, it's direct access to your audience, right? It's like why Sam Harris can say stuff and, like, not ... He- he- ... You can't cancel Sam Harris 'cause he literally maintains direct control to his audience at all times, right?

    24. HS

      Yeah.

    25. GC

      And that's just, that's a different situation to be in.

    26. HS

      Tell me, f- penultimate one, what would you most like to change about the world of product?

    27. GC

      PMs are not gonna like it when I say this.

    28. HS

      Don't worry, only 300,000 PMs listen.

    29. GC

      (laughs)

    30. HS

      Go on.

Episode duration: 56:09

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