 I'm joined by Mark Dunkley. Mark started off as a product manager at Shopify back in 2009 when you guys were only 10 employees. So you've really seen the growth of a startup to become a much larger company as a product manager. And now you've transitioned to a role leading one of the design projects, which is really cool because I think the designers and product managers are probably the two groups or two roles that work very closely together from the inception of a product to actually delivery of it. So welcome, Mark. Thanks Felix. Yeah, so what were you doing before product management? What kind of roles did you have before? What kind of jobs did you work at before? Yeah, when you're a company of around nine or 10 people, your roles are really loosely defined. Everyone's doing everything and obviously we didn't really have product managers until like officially probably around the nine year 100 mark. We didn't really have anyone specifically owning a specific product or a project even. It was all kind of in the air, if you will. And I think that works for some cultures and it doesn't work for some cultures, but around the 90 mark we started experimenting with with product managers and putting a formal team in place. So when I first joined, I was the first designer. The design co-founder hired me Daniel and I was the first like full-time designer for Shopify. So definitely got to grow from a small team to 550, I think we're at right now. Cool. So when you said that you were basically, you know, brought in one of their only 10 employees, how did you get the job? I was trying to apply for like a summer job and I just met Toby and Daniel, the two founders for Coffee and Cody's also founder too. Toby and Daniel and and they saw some of my Shopify work because I eventually got on to e-commerce for my freelance career. There's some small projects, one was like a bakery and the site was featured on like Shopify as like best design website and stuff. So we were having coffee and they just said like, hey, we'd love you to work for Shopify. And that was in the summer and then I dropped out of school after that because I just loved it so much and I did not like school at all. What were you going to school for? Business, business. I was in the University of Ottawa's business program and it was good. You meet a lot of people and did case competitions and the extracurricular stuff really helped but I can't recall a single like thing I learned in class from from school unfortunately. Yeah, that seems to be the kind of common theme. And would you say that you are a or are technical and you feel like you need to have a, I guess, how much of an understanding of the technical implementation of the products that you are designing, do you need to have to be a product manager? Yeah, I'm technical all the way up until like just don't ask me to write any tests like for my code and I'm fine. I swear just a little EIB snippets, designing HTML, CSS, JavaScript, all that fun stuff. Does a product manager need to be technical is a really interesting question. I feel like the most important thing for a product manager is he adds value to his team. And if you're working on a problem that's like super niche, maybe like for example shipping and you're talking about like UPS and how the brokerage deals with UPS or FedEx or whatever, then if that product manager has an extraordinary amount of knowledge in that field both from understanding the trials and tribulations of a merchant and also understands what it is from a UPS and FedEx perspective as well, that's an incredible amount of knowledge to bring to the table. And I don't think that person necessarily has to be as technical as long as he's flanked by some really head designer or lead developer as long as he has those resources available to him. In some ways being technical can be a bit of a burden because if you don't know how to step back and give your developers and designers breathing room to actually explore and make their own mistakes, it can get you in a lot of trouble. And that was definitely one of the mistakes I made when I first came in there. Obviously, I had a bit more knowledge about Shopify than everyone else. I was trying to bestow this cornucopia of knowledge upon these people and I think in reality, you should just let them make their own mistakes and really act as a mentor more than anything. So I think it depends on the project. I definitely would struggle in trying to estimate timelines and estimate the value of projects and how long it would take if I was non-technical and I think in a role like Shopify, you have to be technical because we're so engineering driven. It just gives you respect and you can communicate better with your peers. Yeah, I agree with that. I think that being too technical, I guess you can't really be too technical but you do want to let people that you've hired or let people that's on your team do the jobs that they're good at and that they were brought in to do. And I think what we were talking about before the start of this recording about how I think the product management role, product management job is very transferable to being the CEO or being the founder of a startup or founder of a company and those are kind of challenges that I think a lot of founders experience at first where when they are just by themselves, they have this kind of superhero mentality where they try to do everything themselves or try to have their hands in everything but this is not scalable and that's the main reason why you hire and as a product manager, that's the reason why you have people like designers, project managers and actual developers working with you rather than you doing everything yourself. And you were actually a founder for two companies and you previously worked as a freelancer which is I think a pretty common trait is entrepreneurial experience that a lot of product managers have and now that you are on the product management side and design side working at a company, how do you feel like the skills are transferable between a product manager at a company and then if someone wants to start a company of their own later? Yeah, I think they're very related, very closely related. I see like designers, entrepreneurs and product managers all kind of similar in the sense that they really care a little bit extra in the user experience. They really care about the overall how they sign up to how they get into the product and the first few days in the product especially. Those three roles really care about that initial experience so they're definitely transferable especially I think the biggest thing more so with entrepreneurial and CEO and product management is just time management and establishing a roadmap. Those are skills that are transferable. Even when you leave, if you become a designer again or a developer again you're able to kind of ask yourself, okay, is this something that we should be working on? Is this important? Does it fit my criteria? If you get a chance to do product management and you're a developer, designer, secretary, whatever, definitely jump on it because there's nothing more like as a designer right now, I'm living with the design projects at Shopify. I can communicate better with my product manager or director, whoever I'm speaking with because I understand what they value, what they're judged against and how we both can work together a lot better. So yeah, they're always transferable between the two. The only real difference between product management and design is just what you do day to day. Yeah, I actually want to jump into that next because I heard a lot of things there about the different teams that you work with, how prioritization is important. How does your actual day to day, when you were a product manager, how did it break out? What did you do first thing in the morning all the way to the rest of the day? That's a tough one, man. If you asked me if I was a designer, it'd be a lot easier. But as a product manager, I think Paul Graham wrote an essay on the schedules for manager versus makers. So we basically hypothesized that as a designer, engineer, developer, whatever, you're on the maker schedule in the sense that you have a morning, you have lunch, and then you have an afternoon to work on stuff. But as a manager, you're on an hour, hour by hour, half an hour time block. So you have a meeting here, a meeting here, I am here, coffee with this guy, interview with this guy. It's a lot more broken up. But to give you a typical day, I wake up and I stroll in the office around nine o'clock and just hammer out my inbox for at least an hour. Email is a very dangerous thing when you're a product manager because you can literally spend all day in your inbox perfecting every single little response and brainstorming ideas on how to respond to somebody's question. And if you don't time box, you're going to spend all day. It got to the point where I had to write down what I was doing every day just so I could remember what I did that day. Because as a designer, you have all this tangible output. You can see all the design, you can see all the impact. But as a product manager, it's just calendars and small, almost trivial interactions with people. Yeah. So it sounds like one of the, and I experienced this too as a product manager, one of the, I guess you can say cons of being a product manager, one of the difficult parts of being a product manager is that your job is interacting with so many different departments. And sometimes it is not very tangible what you did. And usually the products that you work on are so spread out over, you know, X periods of months or quarters that you don't really get to see the actual work that you produce. You know, but that doesn't mean that it's not valuable every day that you put in, you're the one kind of glue that holds the entire team together, making sure that communication happens throughout everything. So, you know, that's kind of, I think that's like, I guess a difficult part about being a product manager, what would you say is probably like the most fun part about being a product manager? What's like the biggest like pro for you that makes you say, yes, I'm happy, like, you know, I'm happy to be a product manager every day that you came into work as one. I think, I think there's probably like two things that jumped to mind right away. Number one is to get the bird's eye perspective on the company. You really understand what every team is working towards. And yeah, you can understand this as a as an engineer designer, but you don't do that on a regular basis. You don't talk to the people that you should be talking to on a regular basis. And as a product manager, you're forced to speak to everybody, even like, you know, the head of support, which you probably won't speak to as a designer. So it really gives you kind of a broad overview and you understand as a company that you're moving towards a certain goal, which is which is really, really nice. The next thing that kind of jumps out at me as being a product manager is just being able to see those like as a product manager, you don't actually produce anything. Can you always kind of let your team shine? You never kind of take credit for anything. So as a product manager, you never actually like really do stuff. You don't actually have responsibility. You're responsible for X. You are responsible for however, as those little ideas that you put into somebody's head where you're kind of facilitating these ideas. So for example, one, I remember one time specifically, I'm like, hey guys, people have a lot of problems building a Shopify template. This is from a web design or freelance perspective, a technical perspective. We were talking about it and one of the people said, hey, why don't we make a bootstrap for Shopify? I'm like, yeah, I love that. I just initiated the problem. I presented the problem to them and they came up with the solution. They have instant buy-in and they're able to continue on down that road. And I think that's really awesome. And you know that was kind of like your, like if you weren't there at the company, that may have not happened. That's one of the coolest parts. Yeah, one thing that I've heard and I think this is again, really related to or very similar to the experience that a CEO or a leader has is that if you have a big win, it's your teams. Is there a team around you that gave you that win? If there's something that goes wrong, then you take the responsibility as a product manager. So there are the emphasis on pushing your team through and putting them, in motivating them and getting them to really shine or help them really shining and do really good at what they do. And speaking of doing things that, working with these designers and project managers and other members, whether that be partners or clients, what kind of tools do you rely on a day-to-day basis to help you do your job as a product manager? I think the only special, aside from like IAM and Calder and all that, the only kind of tool that I use that not a lot of other people use is called Simple Note, which is essentially just like Evernote. And I just have a bunch of tabs for any current thoughts or projects. And I write down a lot. There's so many conversations, so many meetings. There has to be something that comes out of those conversations. If not, there's no point in me being there or talking to that person. So usually whenever I have a conversation, I just have a tab, this is meetings, and I just summarize what we talked about. The next thing is probably, and that's unique to me, is that we have an internal app called, I think it's just called a roadmap or something. And it lists all, for each product, it has a list of all the initiatives they're thinking about, that they're working on, that they've shipped, and that they're polishing on. So you can see different states of ideas. And then it also gives you a little bit of a framework to how easy it is, how valuable it is to customers, et cetera, et cetera. So you're able to kind of get a numerical value of the project. Obviously, it's not 100% accurate. But those are probably the two biggest tools that I use day to day. Who's responsible for updating something like that? Because at a company that I worked at as a product manager, we use like Jira for things like roadmaping. And similarly, we had states where things were in like a backlog, or currently being worked on, or prioritized for a certain quarter of the year to be worked on. And but who at Shopify would be responsible for moving things along or deciding how things move along the roadmap? Are you talking about like if it gets this like the stamp of approval, or are you talking about like who actually manages like the ideas and stuff? Yeah, I guess who, the former, like who's actually the one that decides what goes through each, when should it move to the next state? Right now with the way they focus on product management, but the way we kind of used to do it is if the product manager has an idea, he would share it with the director of product management during one of the either the monthly or weekly review or just meetups kind of thing. And then they talk about a little bit further. And then if it gets the green light, it's good to go keep going down that path. I don't think anyone at Shopify is going to tell you, no, you can't work on that. I've rarely ever had that happen. But I have happened like in a really bad, I've had the CEO go like, wait, what is this? Like, when did you start this? Like, what is this for? And like, that wasn't that was not a good move by me. Definitely like over communicate your ideas, if anything, but nothing. Yeah, it's your responsibility as a product manager to curate your roadmap, curate your ideas and present those in a in a presentable fashion. But yeah, no one ever said, said, no, don't do that. It's not that it's pretty flat the organization. What about like things like wireframes or mockups? You know, now that you work as a designer, I'm sure you experienced it a lot, but as a product manager, were you using tools to put together kind of very basic first draft mockups for your designer? Yeah, that's one of the things you got to watch out for. As a designer, that's what I did initially is I just created the mockups myself. But then this is one of the things that we're talking about earlier is you have to give designers space to be designers, and you have to give engineers the space to be engineers. You whenever I mock up something that could be an opportunity for the designer to explore the idea, because they're gonna be one running with it, right? They're gonna be want to continue it from that if I kind of show them this polished mockup, and it kind of gives the impression like, well, why don't you just do it? You already have done like most of the work. It's almost like they're picking up the scraps. So as a product manager, as a design, formerly a design product manager, I would definitely stay away from mocking up any concept. It's fine to mock up stuff and show them to your peers, your other product managers, or the CEO or whoever, but definitely draw the line when you show your team this stuff and keep it really light if anything, you know, whiteboard stuff. I mean, I really should start out the problem with your team. Your entire team should be with you as soon as you start thinking about this idea. It's really important not to go out on your own in brainstorming these ideas, because in a kickoff when you all together as a team talking about the problem, and you have all the answers, well, it's like, well, why are we here? Like, what's the point? And you've missed a lot of good feedback from everyone. And that's definitely the art of product management is being able to guide everyone to that solution you think is appropriate or can actually solve the problem. Yeah, I totally agree with that. I think that's one of the key benefits. If you are going to make mockups, it's really good exercise for you just to have a better understanding of the features that you want to build and kind of map it out in your mind and see like what parts you haven't thought about yet, whether that means from a user experience perspective or just, you know, empty forms that you didn't think that you didn't ever consider that are now really evidence now that it's laid out in a physical form for you. And, you know, speaking of, you know, working with a designer, or speaking of working with other teams, what's your number one tip for working with a designer than if you are, because you're saying that before that they are, they should be a part of the process from the beginning. Maybe we'll start there, you know, who should be working with you from the get go in determining the problem and, you know, from day zero essentially. I think, yeah, determining the problem is definitely the product manager's domain. You know, I don't think you should involve your necessarily involve your team in identifying problems that we should solve. A lot of the time people will look up to you for the problem to be solved. So in that case, the UX team is huge, you know, being in constant communication with them, being in constant communication with their customers trying to understand what they're trying to do with the product and what problems they're having in was blocking them from achieving what they want to achieve. So those groups definitely customers UX people are my two most favorite people to kind of involve in the problem assessing stage, as well as your peers on other product managers, you know, keep this in mind as well. They're always aware of all the problems that they face, and they can even elaborate on some of the problems in their areas. So like if we're talking about the product page and Shopify, you know, adding a product, well, like the guys that handle shipping may have something to say about this, the guys that are theme designers or the theme, theme product team may have like whenever the upload images, they're always the wrong aspect ratio. How can we solve that problem? So you always get a much broader vision as well talking product managers. Now when you work with a designer, what are you like handing off in terms of like actual artifacts or documents, like what do you do you meet with them? Like how do you transition your knowledge and your understanding of the problem and your proposed solution? How do you get that into the designers like hand so they can do their job? Yeah. So I try never kind of hand off anything. Again, like I'm very, I'm very conscious. Now I'm very conscious before I wasn't about about whenever you whenever you start to approach a problem, always make sure that they're involved right from the start. Because if you hand off, you know, a requirements list or, you know, user feedback or customer feedback, it almost makes them seem like they're not a part of the solution just yet. They're not a part of solving. They never had a say to begin with like, even when we talk with a problem like, well, is this actually the problem we're trying to solve and as soon as early as early as possible, bring in your designers and developers as soon as you're like the master of the problem, you fully understand all the variables and what potentially is a successful solution. That could be just a sentence. Like if we're trying to solve a specific problem in Shopify, you can kind of just say like, hey, we're trying to make sure that people can upload images without screwing up the aspect ratio. That's our solution. I don't know how we're going to get there guys, but anyone have ideas and just rapidly prototype stuff. And again, you always have a few ideas in your back pocket. I mean, I'm relying on your team to solve these problems for you. You're responsible as a product manager to guide and to form and sculpt these ideas and make sure that they're always on the right track and they're always, you know, towards that end goal of making sure that the aspect ratios of images are an all messed up or whatever. And what about developers? How do you work with developers when you were a product manager and any tips that you can provide on effectively communicating with developers? Developers is tough because I'm not a developer. And a lot of the time you feel like you're going blind in a lot of situations. If I say, hey, man, can you fix this bug? And it may take the developer one entire day. It may take almost one entire week. And you're kind of like, should this take an entire week? You're not actually sure if the person's performance is really being maximized here. So if you're not a designer, if you're not an engineer, it's really important to have somebody in the company that you can kind of talk to on a regular basis. In this case, we had a lead engineer, and I was able to sit down with him every Friday, like a minimum 10 minutes, I just explained to him what's going on. And then if I had any other things to bring up with him, like, hey, some guy was we're going to bug for a week, you like, is this crazy? Or is this stupid? And it also actually vet a lot of the ideas with the lead engineer, as well, before I kind of brought it to the team and be like, hey, man, is this like a crazy solution? What should I know? So having someone you trust in areas that you are not particularly, you know, fantastic at is definitely something that any product manager should consider. Yeah, having having like allies and like champions, essentially, in the different departments can go really far in terms of getting you the the resources that you need or balancing the feedback or getting feedback from ideas, you know, from them. And you know, you mentioned earlier that one of your favorite people to talk to are your customers. You know, how do you usually communicate with customers and you do you do these like customer interviews to uncover problems and and you know, figure out what what's next to work on on the roadmap. Yeah, I thought I knew how to talk to customers and I saw a UX team in action and like, wow, they did an amazing job. Whenever you're speaking to customers, it's really important not to I think one of the most important things is not to seem like you're digging at anything, it's to have a casual conversation, really see what kind of indirect feedback gets given to you and and and try and and if you do have a specific problem or something in mind that you would like to tackle, for example, if we're talking about product page, we'd say like, hey, like, whatever you're adding products, like, do you find that easy? Do you find like, how do you how do you like, I'm so bad at asking customers and in relation to our UX team, we keep it friendly, keep it a conversation. Don't kind of try and stay away from bias as much as possible. As you see, I just did there, do you find adding products easy? Well, that's kind of a biased, a biased question right there. So yeah, I don't think there's too much crazy, crazy stuff with talking to customers that I mean, the most important thing is that your mind has a really good way of kind of bubbling up the top issues like the human mind can only remember, you know, the top two or top three, or maybe even just one thing about that page. So kind of don't worry about writing every single little detail down because it's just going to get lost and probably never come back to it. So yeah, just having a casual conversation and usually that merchant will be able to list at least one thing that they really are passionate about or so forth. Yeah, you know, speaking of not having biases when you are talking to customers, one thing that one recommendation from a senior product manager that gave me really good advice was to always stay away from yes or no questions rather than saying that, you know, asking them how they feel or maybe even just having them walk you through what they do when they are adding a new product to a product page. You can reveal things that they would not verbalize through words, you know, so cool. So now I want to talk about, you know, getting a job as a product manager and you said that you, you know, hired out, hired straight from school or while you're still in school. So maybe your experience is a little bit different than other people out there that are, you know, already out of school in the job market. Do you have any recommendations on anybody that's reaching out if you were to interview a product manager? What kind of things can they do to really stand out above the crowd of all the other product managers that are, you know, sending in their resumes and applications? Yeah, I'm not too familiar with the whole resume approach. Obviously we just do the interviews and we have like a recruiting team in place to kind of browse through the resumes and stuff. Maybe I'll just kind of share a little bit about I'm never a huge fan of resumes or cover letters or anything like that. The way I got hired at Shopify is I met Toby and Daniel for coffee and then I went back home and that night I just redesigned the entire Shopify admin. There are things that I hated about it and just put it into a PDF document and I sent it to them that night. I'm like, Hey guys, I thought about like some of the ideas we could do with Shopify. Like here are some of the things that I have trouble with and then they were just blown away. Like they were super excited and I was hired on the spot. And the same story with product management, you know, I was a designer for a while and we had no kind of product team or product management team. I wanted to be, you know, I wanted to own something. I didn't necessarily want to be a product manager. I just want to own one area of Shopify that I could totally focus on and just kill. And I remember walking into Daniel's room and I sat down like, Hey Daniel, I want to own, I want to own theme store like the theme store where everyone gets their templates for for their online stores in Shopify. And he's like, well, I don't think that's like, you know, a full-time job. And I sat there and I'm like, Damn, like I don't have to say like, I could, I could say please, please. Like, no, it's not how you do it. You need to have like, well, I'll just continue the story on like, you know, a year later, I went up to Toby, the CEO, and I gave him a presentation saying like, here are five things I'd had to Shopify and identify the problem identified the solution with, you know, really polished mockups and prototypes and the results of these as well as the first thing we do after we implement it, whether it's an AB test or, you know, usage data, whatever. And then he said to me after meeting, he's like, Oh, maybe we'll make a product manager out of you yet. And three months later, I was a product manager. So going back to resumes and cover letters and how to get noticed. The biggest thing for me, my approach is always to be a lot more hands-on. I would take a problem in Shopify, or in any company you're applying for and explore it just as you were, if you were a real product manager, and, and that gives you so much to talk about in the interview. And it gives you a certain depth that no other candidate, I must say the same thing, will be able to touch. Yeah, totally. I think that one of the great things about the product management job when you're applying for one is that you can, it's really a meritocracy where you can prove that you can do the job before you, you do it, it really gives you a leg up. And you can't say the same for other, other, many other roles. You know, if you're applying for a sales job, you can't just go out and get a sale, you know, for somebody.