Expectations in Different Product Roles by Shopify Dir of Product, Agatha Krajewski

Thanks for having me. It's a pleasure to be on the show.

Yeah, I mean, I would say my parents are both electrical engineers and they were inside the tech industry, but they were really on the engineering front dealing with microservices or semiconductors, so very much on the hardware front. I knew I didn't want to go into the engineering front into computer hardware, but technology was always something that was present inside of my family. My exposure as I was growing up... that said, I actually was really interested in going into architecture as a child. And I focused on that so much growing up. And it was just at that last point when I was applying for colleges that I decided, well, why don't I try out business as well as architecture? It was more of like a gut instinctive side to go into business. So technology and the idea of going into information systems wasn't really a thing I thought about when I went first into college. But when I looked at my university and other people that were inside of my business program—finance, accounting, marketing—with just enormous classes with a lot of people moving into that space, and I tended to always be the person who goes into kind of the path less traveled. And I looked at the information management systems course, there was eight of us that were considering going into that particular major. I thought, okay, well, that's perfect for me. And as I learned a little bit more about management information systems, I kind of came to this conclusion that it's essentially the architecture of systems. So it kind of created that bridge for me and made me realize that it's really interesting and it hits a lot of the interest points I had. That was basically my path into technology, and from there everything else just laid itself out afterwards with the kinds of opportunities I got in terms of my career.

Yeah, sure. It's hard to talk about a day-to-day because I feel like every day and every week is completely different, but I think that's also part of the role. So in terms of my day-to-day and my responsibilities, I lead the online store for Shopify. That's basically the most mature and core product. When you think about the company, you think about the Shopify store—the merchant experience of setting up the new online store as well as the buyer experience of interacting with it. Beyond that, it's the email marketing product, it's a new product. So my day-to-day really looks at how we've broken down the online store and email marketing into kind of different subgroups, and I've got a product leadership team that's split between those different pillars. Depending on the area and the investments we're doing between those different key initiatives within the product organization and between my group, I might be more on a strategic advisory role, helping to make sure that the roadmap we're building out two years out is aligned with the long-term growth and opportunity that we see within the market for that area. So it's more of a strategic advisory guidance kind of growth. In other areas, we're talking about major infrastructure rebuilds of core components that impact the million-plus merchants that are on the platform. So there I might get into a much deeper kind of understanding and not just strategic direction of that rebuild, but really getting into the details of what is it that we're building, how do we scope up the MVP, what do we need to define, who do we need to work with across Shopify. Because nothing, I think in most companies, nothing is done in a singular lens of one particular team. As your company grows, there's interdependencies across all these different teams. So aligning your stakeholders, making sure that everybody's aligned with the vision of what you're building, but then you're also making the right technical decisions and compromises on whatever your first MVP is. So I might be going into a meeting where we're talking about resource and headcount planning a year out as part of our investment portfolio for the big things we want to focus on. And then I might be going into a very tactical conversation about use cases and analyzing to say, is this something that should be within the first MVP scope or not? Beyond that, I would say aside from that day-to-day product work, most of my time is then spent aligning with other product leaders or leadership individuals across Shopify to make sure that we're all working on a cohesive Shopify strategy and that we're all talking apples to apples. So I'm not working on something inside when somebody else is working in a different area. Bridging apps and actually referencing different people to other parts of the organization when they're talking about a particular feature that they're building to connect the dots so that everybody's working towards one overall goal and we're not duplicating efforts towards that vision.

Yeah, I mean, first is you've got to have relationships. It's so much easier to have a frank and serious conversation about priorities if you actually have some sort of a relationship with that person. That's really even just like a video call, especially in this world now, so that you have a face behind the voice or behind the name that you're messaging. And just gut-check alignments with different people, so checking in and seeing how your teams can help those teams align with their objectives always gives you a big advantage for when you as a team need help from that other group. Beyond that, having synthesized—I'm a huge proponent of frameworks and structure. Everybody on my team knows that I'm a very structured person. So having a synthesized overview of your roadmap with a clear... we all know that roadmaps change all the time, that you can't commit to everything on top of your roadmap, but it's a great way for people to know what you're thinking and at the current state and time what is your future plan. So it helps to build the trigger so anybody at any point in time in a different part of the business can take a look at your roadmap or your strategic plans and see how aligned they are and raise questions with you when they're uncertain. So I think between communicating broadly and sharing your plans and making it accessible, making it clear that you're not a wild card or guarded within what you're doing with the individual team, but be very open and transparent about your work. And then having those spot relationships between different people—you do not have a relationship with everyone in the company, but you have a relationship with someone, they've got relationships with other people, and all of a sudden you've got your network of the entire business to be able to lean towards different individuals if you need to get something delivered or aligned, or even just to get feedback and gut checks on what you're thinking about prioritizing.

Yeah, it's actually a funny... the reason I went into software development was completely arbitrary in the sense that I had a business degree, I did a couple programming courses on the side, and when I applied to my first job, I was applying for a consultant role. I really wanted to become a consultant when I came out of university. But because of my background and having a few computer science classes, the company recommended that I try software development first because they very rightfully kind of informed me that understanding how software is built and really getting hands-on it will help me then be able to shape my direction and to understand the implications when I'm doing consulting work in the future. So I very gradually—because it was my first job, you're going to say yes to it, you're going to be converted in your career—so of course I said yes, grudgingly but accepting that it's a step forward. I did software development. It was in the context of what's called the professional services department. So we had a platform in this company and I was responsible for taking that platform and actually building the product on top of it specifically for each individual customer. These are big enterprise customers that were asking for this software. Within the first year of doing a number of different implementations—I probably did about 10 or 15—but by the 15th one, I actually had a playbook of all the things that need to get fixed in the platform that I was leveraging in order to build my software. And it was kind of a rinse-and-repeat series of bug fixes, features, and enhancements that I would layer in, and then I would start the actual work that was like the specific needs for that particular customer. So after a year, which was kind of my agreement with that first company, I was saying that I will be a software developer for you as long as you give me the opportunity to move into consulting afterwards. So on the day after the first year, I basically came to my boss at the time and said, 'All right, it's been a year, I'd like to move to consulting.' And they said, 'Okay, you can move to consulting if you want, we'll transition you into it, but there's also this thing that we're doing in our R&D organization. We don't really know what it is, but we've been hearing about this need for product management. We don't have a team on it, but we're starting to build some building blocks around it. Might be something you're interested in.' And so it's actually by complete luck that at the time where I was trying to... I got that exposure to software development but wanting to change into something that was more business-oriented, the company was looking to create product management. I moved into their role at the time. They didn't have a title for the first, I think, three or four months. They didn't know what to call me. Eventually we landed on a product specialist because I was very junior in my career, but I was starting to work on that product angle. And since I got exposed to that, it fit perfectly to what I was doing before with the implementation team where I was already extracting the commonalities that we needed to do to improve the product, to fix the defects that were already in the platform. It just translated perfectly into that product support or product specialist role. And I basically never looked back from there.

There's definitely a difference. I can talk to it, but I think also to make it as a blanket statement, product management is different at every company. There's kind of core aspects of product management that are the same, but how product management operates at every business or every company that I've worked with or I've talked to people at, there's a completely different profile. I mean, some companies call them program managers but they are essentially product managers as well. Other ones you might have a product marketing manager who's doing a lot of the product management work as well. So titles, I think, are a little bit fluid. You kind of have to dig a little bit deeper to understand what are the expectations of that particular role. Let's say the difference in what I was doing before as Chief of Product Management—I was working as a Director before I went into Chief of Product Management. When I was working as a Director, it was quite similar to what I'm doing now, just at a smaller scale. In that lens, I was working at a sub-component of the bigger platform that we were building within Lithium or within ADP. When I moved into Chief of Product Management, my responsibility was really about looking at kind of taking a step back. We were building a completely new enterprise HR software that was going to target human capital management solutions for enterprise customers across the world. It was going to be—and is in the process of becoming—ADP's next-generation platform. We were talking about all components of HCM, from your core kind of organizational management system to payroll, benefits, time, compliance—everything that you think about at HR is basically that. And so when I moved into the Chief of Product Management role, I was responsible for looking at where we are today with the size of the enterprise customers that we're targeting, where we've committed to from our kind of strategic plans to the Board of Directors a year out, and what key initiatives do we need to start today to build the platform foundations in order to be able to actually hit those commitments a year out. So I was working on things like architecting and defining ADP's engine for workflows and approval processes, for authorization engines, for the core eligibility engines and compensation management. So a lot of these kind of big infrastructure projects. I was probably working about three to five at any given point in time, and in total probably worked around 25 of them during my time in that role. What was really unique about that role compared to kind of traditional product management is it was fully leadership through cross-functional management. What I mean by that is that I didn't have any direct reports. I had a dotted line for everybody in the product organization reporting to me, but I didn't actually manage anyone. My entire influence needed to be through generally thought leadership across the organization. And I would have at any point in time teams in a dotted line reporting up to me. I'd be driving the strategy behind that particular project, defining the vision, figuring out the MVP, doing the technical designs. So very much hands-on product work on big, complex net-new builds, and mentoring the entire team to be able to get to that first MVP. And once we would launch the MVP, I would kind of take that group and hand it over to one of my peers who would be in a VP or a Director role at the time, and then they would take it and then they would grow it, and I'd be on to the next key infrastructure pieces and working with my new team. So I was pretty fluid across the whole organization, working on the most complex and important projects for us to succeed in order to meet our kind of key milestones that we set as a company.

Well, I mean, partially I was still in the senior leadership group, right? So it was still at a senior level. So obviously I had influence on people's compensation, performance, and all of that. But more than anything, it was very much around influence and respect. You can't be a successful product manager if you don't have that. I mean, from step one when you're a product manager on a team, even at the first level of your career, you don't manage the people that you work with. You lead through influence and you lead through passion and mind from that group towards the vision you're building. And whether you're again a product manager who's working as a member of a team, or whether you're a Director of Product or VP or Head of Product of the company, you have the product group reporting to you, but you don't have the engineers, you don't have the go-to-market—sometimes you do, but not always—you don't have UX, you don't have the whole company rallied. So you have to be the salesperson, the person who rallies and motivates everybody around it. So it really wasn't any different than had I had all those people reporting to me. It made my job a little bit easier because I could really focus on the nutty problems to make those products a success without dealing with the day-to-day people management components, but rather focus on mentorship. But beyond that, there wasn't really much difference in lack of influence because at that point you've already matured in being able to create that rally around the vision and strategy that you're building.

Yeah, so we've been at Shopify working remote since mid-March, and we've actually announced that we won't be going back to the offices in the way that we were traditionally. So we will most likely be moving forward working from home indefinitely and still figuring out when we will be getting together in an office environment, likely for specific workshops or sessions. But I think the hardest part we had, particularly as a product team, is because of that element of influence and rallying people around your vision—it's harder, right? It's harder when you don't have the energy in the room to get people excited, to kind of share your energy. It's harder to share that energy through a video call than it is in person. We always do video—every call at Shopify is a video call—so at least you do get to interact with individuals and you see it's always easier when you see that person than when it's just a voice on the other side. But that's probably the biggest challenge I have to bring my product team around. It's how do you still have that same wave of influence and excitement and share that with the team to get them rallied to run where you want to take the product. And I think the second thing that we're all still struggling with is how do we do these workshops? It was so much easier when we could all just sit down in a room, get in a whiteboard, lock the doors, and just draw it out and hash out the problems and the differences and align together. We're trying out lots of different tools. I'm a huge slide person, so I've become a little bit of a slide master. So even when we're having conversations and we're just talking, I'll just start popping out slides and just start drawing things out as if you were whiteboarding, I'm on slides so that at least there's a visual to follow. You might have a whole 30 or 40 slides after a conversation of complete junk, but at least it helps guide the conversation towards an outcome. So I think what's been helping the team a lot is I use slides, other people use Figma for UX wireframe components. Find your own thing that helps engage the conversation. Don't just have a chat where you're all staring at one another in a video call, or even worse, you're just listening to each other's voices. Find a tool to bring you guys together and then push others to start kind of co-collaborating with you in that tool because that's the closest you can get to having a collaborative workshop. What's great about that exercise though that you didn't have in whiteboards is that you actually already have a digital copy of all the stuff that you've been discussing, versus before where you'd be taking pictures of the screen and then they end up like going into a folder or just sitting on your phone for ages and eventually you will start to make some of those into a digital format.

Yeah, so Shopify is in an unfortunate situation where we were an e-commerce platform, so we have the ability to help a lot of the businesses that really struggled through when COVID happened. And so we actually did a half-day project across all of Shopify because it's basically spend a few days, figure out what you could do within your business units to make things better for your merchants, especially focusing on our retail merchants or service merchants—people who had physical locations or provided services that you just couldn't do anymore. Restaurants as well, another great example. So we came up with a lot of different ideas across the board within Shopify. Specifically with online, we did a lot of things just to help those merchants get through the hard times at the beginning of COVID and to augment up. We extended our free trial period for setting up your online store from two weeks to three months. So we took the hit from ourselves, but we knew that that was the right thing to do for our merchants, for customer pace. We brought in a bunch of features that were typically available only in more premium versions of our software to the basic versions, things like being able to leverage gift cards. Gift cards were a huge help for a lot of the merchants because when they couldn't provide their services, when they couldn't manufacture their products because maybe it was an experience that you needed to have within a retail store, at least gift cards allowed customers to help support that brand through that particular period. We also created new quick experiences within the online store so that you can quickly get your business up to market, especially for restaurants, for services, companies that aren't used to e-commerce that are just getting in—created the most streamlined, easiest experience for you to get online. And then again, you have that free trial as well. We brought in Shopify Capital—not in my group, but in another area—to help businesses who weren't able to pay their employees because they weren't making money, to help bridge the gap and to get themselves set up to whatever it is that they needed to do, or even just to support them during that three-month period. So we definitely, we basically looked at our roadmaps and we said, okay, pause everything, take a look back, what is it that we can do to kind of pivot to be able to help our merchants today that'll be more impactful than some of the projects we're working on. There's projects that we obviously kept continued and didn't change because there's value for them regardless of what's happening in 2020. Those things help our merchants today, they'll help our merchants tomorrow. But for I would say a good 50% of the team, we took a pause and then we pushed for quick features and fixes or kind of revisited our business plan in order to be able to help them. And another example is we were just about to launch our email marketing product and then COVID happened, so we decided to defer pricing. We made it a free product until October because we found, well, email marketing can actually really help people today to communicate: what are you doing about COVID, what should I expect from you from a store if you just launched your online store presence because you're a retail business before, here's a template for how you can communicate that. So again, just trying to think of what were the things that would be most impactful to our merchants at that point in time to help them essentially sustain their business, because we were literally talking about companies surviving at this point in time and what we can do to help them.

Yeah, I think also a big part of it was data. I mean, we can see what's happening with our merchant stores, we can see their sales decreasing. We also have a retail division at Shopify, so it was very prominent for us to see what's happening with our retail businesses. And based on the ones that were most impacted, those are the ones that we said, okay, these are the businesses that we need to help get online as quick as possible. And then also just general data that was getting reported across the U.S., across North America, that gave us indicators as to who's having the most negative impact from the situation, and then how do we actually focus on them and help them through the Shopify platform.

Yeah, I guess there's no clear-cut answer. There wasn't one probably before, now either. I think there's probably still some ways you can network informally, obviously not in person, but joining local communities that still might have some kind of online sessions or even just connecting through people through that lens. But in terms of learning about product management specifically, there's no, in my opinion, there's no clear-cut one perfect profile of a product manager. It really, to me, when I'm hiring somebody, depends on what's the role I'm hiring for, what is the skill set of the peer leadership team—in the case of working in the trifecta, there's UX leaders and engineering leaders—what are their strengths, what am I trying to fill with this particular role that I'm hiring, and then what is the problem we're solving for. Are we solving for really complex, nutty problems that are very deep, or is this a very horizontal problem that has a lot of different ways in which it can be solved but there's not a definitive answer and it requires more of kind of like an innovative strategy and thought leadership in the space. So I think when I think about product managers who are going into the craft, I would say get familiar with the different types of problems that product managers solve for. In those examples, we're going really deep. I think about my checkout world—it's a very definitive answer. You've either charged the person correctly, you've taxed them correctly, and the transaction is complete. It's a black and white yes or no whether it was successful. To get to that state though, it's an extremely complex web of interdependencies and internal kind of infrastructures that we need to build out. Someone who would excel in that role is someone who really likes to go deep into a problem, and I think we can get quite technical in that space. Versus if I think about our email marketing product, there is no 'this is the right way to do email marketing.' It's a subjective product. It means that you need to define your own innovative positioning compared to the competitors in the market. So it's a different kind of perspective and product. So I'd say on one hand, think about kind of those two spectrums—which is the one that you think you're more specialized in or you think you would be more successful in? Is it bringing structure to a very unstructured problem, or is it really going deep into a complex problem and understanding all of the kind of edge cases and complexities? Different personalities kind of fit better between those two spectrums. So if you can figure out that, then that already gives you a clearer lens as to what kind of roles you could be interested in. It also helps you position yourself as a strong candidate for one of those two lenses. As new graduates coming out of college, you're kind of like dough in a way—you can be molded based on the experiences that you get to become specialized in one part of the craft or another part of the craft. I would say be open to the opportunities around you from a product perspective because every type of product challenge, and whether it's in technology or not, you still gain a lot of the core product management fundamentals. So again, it's not a really easy or kind of clear-cut answer, but those would be some of the things I would recommend that you kind of think about a little bit from a product perspective. And in your interviews, when you do get to a point of doing an interview, remember that it's just as much you validating if the fit is a good fit for you as it is for the company. And a big part of it is culture fit within the business. Understand how the manager thinks, will the manager be there to mentor you as a person entering that career? Mentorship is so incredibly important. Is this a person that will actually help guide you and teach you kind of their ways of product management? And that's to me so key because it's through multiple different managers or leaders and learning their different frameworks—because we're all different—that you actually get to understand your own way of doing product management, because we all do it a little bit differently.

Ah, that's an interesting question. I mean, there's lots of personal things—like my daughter's growing up, I'm really excited to see her get older and just see how she develops and see which traits of mine she actually has. In the world of product craft, I've spent the first year at Shopify really building up my team. We had nowhere near the amount of product managers we needed to have for the amount of engineers and UX designers, developers, and the demand in the company for what it is that we needed to build. So a big part of it was just growth and building up the building blocks to make the team sustainable. Now kind of making that pivot towards being able to myself actually also focus on some of the really interesting problems. I'm definitely the type of person who vectors towards the product from zero to one. I find it so fascinating to do these deep infrastructure builds to get to that first version of the product. I get less excited when we get to that from the five to a hundred. That's where I tend to hire product leaders that are really great on the growth of projects. So I guess what I'm really interested in is actually now at Shopify getting to really some of these really meaty infrastructures and planting some seeds and really supporting the company build up into kind of the future generation of a lot of the online store components. That's kind of where my passion always is, and it's a part of the job that I love by far the most.

Yeah, it's a doozy. I feel like I'm going to almost flip that a little bit and then you'll tell me if I need to come up with another answer afterwards. But yeah, in terms of what is the greatest lesson product management has taught me, I think it's actually the fact that from day one of myself having kind of my own personality, I was always a product manager in the way I acted as a child, in the way I grew up, in the way that I had little jars to allocate all of my different... like my allowance got allocated into different jars, but they were prioritized and I had a priority list of what I wanted to buy. Every time I was going on a vacation, I'd build literally a binder of all of the places that we wanted to go and see on our road trip. We're thinking about actually the entire group of people and what they would be interested in versus what it is that I'm interested in seeing, and then having that 'we must absolutely see these things, this would be nice to see if we happen to have extra time, maybe we should see this'—this kind of prioritization of my entire life and planning has kind of just been the way I've always operated. So I think the reason product management fit me so well was because it actually is my personality. The things that you succeed in product are the things that I've kind of always lived by principles my entire life. So it was such a great fit. I guess the realization from that is whether it's product or whether it's whatever discipline or job that makes sense for you, if you can find that fit that aligns with who you are, your passions, your personality, what drives you, with the job itself, you kind of don't need to worry about everything else because you're happy with what you do and success, kind of career growth and opportunity, it kind of comes with the fact that you're enjoying what you're doing. It's contagious at that point. That's probably the biggest lesson. So the fact that if you choose the right job, if you choose the right career, the options are endless for you, but it also doesn't matter because you just enjoy what you do on a day-to-day basis anyways.