Expert Roundup: A Discussion On Product Management Ft. Shopify, Planswell & More

By BrainStation July 31, 2017

Interested in learning more about Product Management? Curious to learn what it takes to successfully lead the product teams that build and manage the hottest digital products?

The role of the Product Manager is one of the most sought-after careers in the tech industry today. PdMs play a crucial role in driving the development of a product and act on behalf of customers’ interests. From facilitating communication between engineering and design teams to relaying customer needs, Product Managers oversee the product lifecycle from ideation to execution.

We sat down with three Product Management experts to learn more about how the role has evolved, how you can break into a career in Product Management, and what it takes to be a great Product Manager.

Our Experts

Brandon Chu is a Director of Product at Shopify where he leads the platform product group. This group builds the platform that supports tens of thousands of third-party developers as they build apps for merchants on Shopify. Previously, Brandon was a product director at FreshBooks and co-founder of Tunezy, which was acquired in 2013. Brandon writes a Medium publication called “The Black Box of Product Management” which aims to take Product Management from theoretical to practical through providing frameworks that help readers become better product people.

Zhi Hui Tai has experience working in product teams at B2C and B2B SaaS startups spanning across Singapore, Silicon Valley and Toronto. With her background in Applied Mathematics, Zhi Hui started her career in Data Analytics at Game Ventures, a social gaming startup which developed a best-in-class online cricket game, Howzat Cricket. She later moved to Toronto to join the early Product Management team at Influitive in 2013 to build an engaging marketing platform that provides B2B Marketers unprecedented access to engage with their customers directly for sales and marketing growth.

Zhi’s latest adventure is taking on the financial industry at Planswell, a fintech startup with the mission to give all Canadians greater access to sound financial planning services in order to help them work towards achieving financial freedom.

Tom Levesque has lived in three countries. In the Bay Area, he led data Product Management at Wildfire, which was acquired by Google. At VigLink, he was instrumental in raising a $20M Series B. Locally, Tom has worked with Bell, Rogers, Myant, Index Exchange, and enjoys advising a number of startups. He is currently co-founder of a deep learning project and a Product Management Educator at BrainStation.

Tom studied computer engineering at University of Waterloo; he did a work study as a software engineer. He applied for a job as a PdM and has been doing it ever since. His startup, attempts to compute what types of people in the world should meet, from a professional perspective.


Q: The role of a Product Manager is so multi-faceted; you’re in charge of the P&L statement, the development team, the design team. How did you learn to become effective?


Brandon: I had to learn everything from scratch, learning to build empathy with everyone you work with. When you join a team you’re actually slowing them down, so combating that is about having enough knowledge of everyone’s craft to understand how hard it is to build a product. Once you build that empathy you can make balanced decisions that the whole team can rally around.

Tom: I don’t want to do the same thing every day, wearing different hats. Product Management allows me to one day present to the board, the next day figuring out why the software won’t run, the next day writing copy for the website etc. That’s the fun part, you can’t possibly be an expert at all those things so you’re always learning. You can’t approach that from a formal learning perspective; you’d be 97 by the time you’d gotten a business degree, marketing degree etc.

Recognize there will always be things you don’t know and be ready for that. Be quick to identify what you don’t know; identify who the domain experts are in your company and rely on your counterparts for feedback and knowledge. Always be good about figuring out what you need to know and do it fast.

Brandon: PdMs get really good at how to hack stuff together; the more we don’t know the more exciting it becomes.


Q: Opinions on whether or not you can be an effective PdM without a technical degree?


Tom: A lot of people use the phrase technical or non-technical person. I don’t believe people exist in this binary world where we split people into these groups. People who are technical fall into all different categories, there’s nothing magical about technical knowledge. You can learn it the same way you can learn about anything else, history. Just start learning. Don’t take it as a big project like mastering Python, just learn one thing, and then learn one more thing. With regards to degrees, if you’re just starting out and you’re 18 I would advocate for computer science or engineering, but if you’ve already gone to University I don’t think you need to go to get the technical knowledge you need. We fake it a lot.

Brendon: There’s this weird imposter symptom that everyone feels in tech; people are afraid of looking dumb technically, you just need to fight that fear and when you don’t know a term, ask. You’ll become incrementally better and better. I learned everything I know about the web through doing it. What you learn post university can be really substantial.

Zhi: Should I get a technical degree is a question similar to should I get an MBA; I don’t come from a technical background which gives me an edge, I give developers the space to explore different options. But I’m good at identifying the problems and I oversee that they get solved.


Q: Your role on a day to day can change so much; there are two ends of the spectrum; the startup environment, focused on growth and making sure you don’t make mistakes and put out the right stuff at the right time and you’re focused on the growth data, and then there’s the other end of the spectrum, like an enterprise. You might be less inclined to define direction, more of a shepherd of the process. These are the same jobs but very different roles; what makes someone successful in either?


Zhi: On the startup spectrum, you have to be careful to not create too many processes as you don’t want to slow things down. Your core mission is to ensure when the product goes out that it’s successful. In a bigger company, there might be more speciality roles that can help you in those buckets, but in a startup it’s all on you to ensure it’s successful.

Brandon: Company size leads to a change in your style of Product Management, I also think culture can really determine how much the company buys into rigid vs. more fluid product development. I think the other side is how quickly the company is growing, if you’re a big tech company and you’re at 10,000 people for 10 years you’ll develop a cadence and process that’s more rigid, but if you’re a company that’s 1,000 people last year and 10,000 this year, it’s more chaotic than a 10 person company because no one knows what’s going on, there’s a million things you can do, so many people to wrangle and a lot of people building things that conflict with each other. So there’s a lot of different dimensions to it, the general thing to think about is how can I take the time that I have, knowing that I don’t actually build the product, how do I accelerate the team to build it faster by helping them make decisions, and more importantly getting them to make sure they can build the thing that matters to customers.

Tom: I think startups need generalists in every role, generalist Product Managers whereas facebooks of the worlds have more of an opportunity to specialize and dive deeper into something. You’re going to have more structure, more mentorship. My bias is that you can learn a lot more in the startup world, particularly if you’re self-directed, if you find you’re the kind of person that really needs process, then the more enterprise world might be better for you, especially if you can find a good manager. You’ll be forced to learn more in a startup. What you will get in a larger company is learning how to deal with scale; launching a product to 1 user vs. 1 million is very different, things come up at that scale like in the Shopify world that you’re just not going to run into at a startup.


Q: Do you think it’s possible to have an enterprise Product Manager that has the ability to work in a startup environment?


Brandon: You have an extra factor that there is something important to lose; I think you can have a founder’s mentality in any company, but you may have a smaller box in terms of creative direction and way more factors that you have to incorporate. When you launch a product into a very large user base you probably don’t want to go zero to 100, you want to figure out how to gradually role it out from 1% to 2%, because when a product hits scale, you don’t always know what’s going to happen because you want to be able to prove it’s stable. The mentality is always how can I do more with less, what resources do I have and how can I drive more impact in that and how do I understand all of the constructs and context to make a good decision.

Tom: I’d echo that, it’s not that you’re locked in necessarily, but you’ll spend more time making arguments for what it is you think the right thing to do is as opposed to just doing those things. That’s the tradeoff because there’s something there to protect, there’s something at stake so you’ll be more conservative.

Zhi: You want to have the entrepreneurial mentality regardless of what type of company you work for. You always want to be quick at learning, and taking risks, part of it is also knowing the bases you need to cover. Once I was too gung-ho about rolling something out, and it put a stop on everything and put frustration on me and my team but it was because I didn’t communicate how it was going to happen early on enough, so if we want to move quickly, we also need to know the bases we need to cover.


Q: At the end of the day, what you really do on a product team is make decisions and defend decisions. Ideally, you’re in an environment where you can point to data, a market that exists, or some kind of validation that what you’re doing is true. There are a lot of times where that’s not the case and you need to make a snap decision. In those situations, what is the framework that you lean on to make informed and effective product decisions?


Zhi: first thing that comes to mind is to determine if a particular decision needs to happen right now; if I need to make that decision right now I try to figure out at the technical/strategic level, is this something I need to make a decision on or something an Engineer or Designer can make a decision on. Part of it is empowering people who are working on the product, so over time, they become less and less dependent on you to make decisions. We add a layer to the process, so having the team figure out when they are the best person to make the decision is a way we scale the team.

Tom: I break it into two parts: there’s the scenario where it’s make this decision right now, where my advice would be similar to see if you can delay or make the least impactful decision that you can at that moment. Jeff Bezos says “if you can walk back through a door, then there’s no point in worrying about that decision because you can undo it”, so if it can be easily undone, go ahead and make it, but usually if it’s a snap decision try to delay until you have more information. In terms of the framework, I’m a big fan of Clayton Christiansan, Harvard Business School professor, wrote a couple of books, the Innovator’s Solution is the really critical one, I consider that one to be a Product Management bible. It does not contain the word Product Management in it, it’s a business book, but it’s super useful and will really unlock a lot of different things about product strategy and how to make optimal business decisions. So I really encourage you to pick that up.

Brandon: When a team is facing a decision, there is always that teachable moment where you can start to distribute decision making and asking what’s the worst thing that could happen if this is a bad decision, how many people are going to be affected by it, getting people to think about risk and reward every time they make decisions.

Zhi: If you feel too confident about making a decision, I would argue that you’ve waited too long. You should have some level of discomfort that something might be wrong, you might be taking some sort of risk. PdM’s always take the hit.

Brandon: With the design process, UX people are very big on validating their assumptions and testing their designs. What I have found is one of the hard things is there are times where you need to rely on judgment and experience too. You don’t need to recreate the wheel every time I create a form for example, that’s been done a million times on a million different products, we should be able to build on the research that the entire industry has done over the past couple of decades and be faster, so I think when people are being too conservative in their decision making, I try to step in and give them license to go with what they think is right.


Q: When a decision doesn’t go right; you make a gut call that backfires. Tell us a bit about a decision failure in your Product Management career, and what it taught you about the role.


Tom: Mine wasn’t one event or one day, but it was a long term thing where we had great technology and not a great product. Being a technology person I really loved working on the technology; every product person tends to have a particular area of strength, and you’re going to gravitate to that area, and for me that area is technology. So we ended up spending a lot of time building something that was really cool technology, but not very useful to any people alive today. And so you almost need to do the opposite of what feels natural to you, like working on the technology…don’t to try to force you to even out that skill set. That was my big learning. And the classic goes back to the customer, product 101 type thing.

Brandon: All of my big failures have just been that; the comedy of falling in love with our own idea, going in the hole for 6 months and launching it thinking it’s going to be great and then no one uses it and you find out that your base assumptions about why a person needed this was wrong. Always find a way to know what your biggest assumptions are that you’re making about what people want and why and take the fastest route possible to finding out if that’s true or not. Sometimes you’ll have to build something, but more often than not you can go ask them or find data, or build a landing page that is showing a product that doesn’t exist and says buy now and see how many people click. There are always ways to shortcut it. So be very cognizant if you’re ever going to actually build it that you should have some good foundations that you’re solving a real problem.

Zhi: One of the earliest projects I worked on at Influitive was creating the onboarding experience for users. Coming from a social game startup, I was super pumped about it, thought I was going to nail it, so I walked into it going through the exact same process. But the thing about building an onboarding process is you have up to 3 minutes to convince your user that this is the best product in the world, this is why you should use it, these are the benefits. Me and my team build that process, and the thing I forgot about was validation; at the social game startup we had the luxury of numbers. But at Influitive the numbers weren’t coming at the volume I was expecting. So the mistake I made was I used the same tools that I had in my toolbox, walking into a totally different industry, totally different product. The biggest value for a Product Manager is knowing when to use the right tools for the problem you’re trying to solve.


Q: How have you witnessed the role of Product Management change over the past few years?


Zhi: I think one of the biggest changes in the software development world is the speed at which we are deploying products. As a PdM, that’s super exciting because we are learning at a much faster speed and we can validate things at a faster speed, but then the flip side is this constant paranoia in my head, are my engineers going to have things to do? The worst thing that could happen is PdMs are “chained to our desks” creating stories to feed our engineers, not having time to do actual customer validation. Companies are trying to strike a good balance between PdMs and engineers, so the idea is to just give the PdMs enough resources to move fast, but not over resource the team such that the PdMs don’t have time to interact with the customers.

Tom: I think the role itself is moving from tactical to strategic, broadly speaking. You’re seeing more and more product people who are basically executives almost, without even a fancy title but they have that level of status within the company. And then to your point about the industry itself, all products are becoming technology products, we know this, so I find within Product Management a lot of people are narrowly thinking technology just as software or apps. There’s so much more out there right now, and the way that you do Product Management in these different areas of technology, whether it’s transportation or virtual reality or space, there’s all these interesting things that are up and coming and the way you do Product Management in each industry is a little bit different. The fundamental principles are the same, but there’s domain expertise that you can build up. Releasing every day doesn’t work if you’re building transportation system for example. I encourage people to think about technology broadly and not just software, not just apps, and if you do think about software I encourage you to think about the bleeding edge, machine learning, deep learning, because that’s where all of the interesting and new value is going to come from. It’s probably not going to come from another app. I’m sure there’s going to be 4 or 5 more photo sharing apps that are built and sold for billions of dollars, but beyond that, I really think the value is going to come out of machine learning types of things that drive a lot of automation.

Brandon: I think a general movement away from more project management, specing things, backlog management towards a more strategic role, leading teams, the soft skill side of how to energize and build a good team, and that’s an example of where technical skills are less important and ux skills are more important. My boss at Freshbooks told me that when he was at Microsoft he was working on Excel. He literally spent 8 months building this 150 page spec of every single nuance and feature that needed to get built, how to handle every error, all of the copy, and then they would have a two month process where they would debate engineers about what’s in this book, and then he would give it to them, and that was the end of his job. He literally never saw it get built, it launched two years later, that’s an example of the heritage of Product Management which was really about dealing with the complexity of building software, helping people break down things into these tasks and making sure that the project runs smoothly, whereas today we have tools and infrastructure and things like Github that allow things to be decentralized and to be done with a lot of teams. Where we apply leverage now is what is the direction, what is the purpose of our being as a team and as a company and what kind of impact are we trying to drive and how can we do it faster.


Q: Looking forward, do you think Product Management is vulnerable to disruption?


Brandon: Yes, I think it’s going to get disrupted. I think the same way that Product Management evolved from dealing with the complexity of software to where it is today, I think that can be even further distributed amongst the team. I would never advise someone 12 years old to try to become a career Product Manager. I’d say try designing some stuff, build some stuff, sell some stuff, market some stuff, and learn the basics of Product Management. Learn about what people do and I think I’m a minority in this opinion but I think a team operating together can be more efficient than having a dedicated Product Manager.

Tom: If you think of a business at a fundamental level, it’s build something and sell it for more than you paid to make it. At no point in there does it say “and Product Manage it”. There’s something extra that we’re doing to make sure we’re doing the right thing, but this isn’t the only way to figure that out.

Zhi: I think the role is going to change to some extent, but I feel that at the core of it, our job is really about communication and company-wide alignment. There’s always going to be a need for this job communicating in different languages to sales to developers to marketers, you’re always going to be dealing with different personas, so at the core level there’s going to be a need for a “glue”, but with technology catching up, part of the downstream work that PdMs do may be eliminated, especially the very repeatable stuff.


Q: Looking back at yourself 5 years ago, what advice would you give to someone who is targeting a career in Product Management early on? How can they position themselves to be as successful as possible?


Tom: It depends where you come from. Find a domain that is related to where your source of strength is and try to ask for the opportunity to champion a project in that area in the company you’re already in or in a new company. If you’re coming cold like I was from a completely different industry, I would say put yourself in the shoes of someone that is hiring a Product Manager and think about why they would take that leap for you. You actually have to give more evidence that you can learn quickly, that you can at least understand how the sausage is made in whatever type of product that is. So learn how to build an app, even just to display that you could learn that. Show that you understand how to design something, build up some sort of evidence that it’s not all talk and that you know how products in that area are made. And then network; most people find their jobs that way, so I keep recommending that.

Brandon: If your goal is to get a job in Product Management, there’s no amount of fancy words you can put on your resume that will compare to just building something. I would say start with software, Python is ridiculously easy to learn the basics of, and actually that’s not even the hard part. Anyone can build something in Python given a little bit of time, the hard part is getting people to use it, that’s actually the Product Management part of it. So try and see if you can get your family to use it to solve a problem for them. Show that to some employers and they’ll be interested.

Zhi: I think leverage what you use day to day as a user. How do you feel about that experience as a user? What would you change about it? What do you think could be better? What do you think is good about it? For example, who uses Car to Go? Car to Go comes with a built in navigation system, which is great for the user, but its keyboard is laid out from A-Z horizontally; it doesn’t use the most common layout. So as a user I’m keying in my address in 2-3 minutes versus 5-10 seconds. So as a user it’s extremely frustrating because it’s a pay per minute service. So, I’m paying for a bad UX decision. Look for opportunities like that to build your product instincts and gut for interviews when people ask you about your favourite products or ones that can be improved upon.

Tom: We’ve talked about all of the things that might make you a good Product Manager, but one anti-pattern to think about is if you don’t get frustrated by about ¾ of the products you use every day, you might not make a great Product Manager. You should be using products and services all day and be going, “why does it work like this? Who built this?” That’s the kind of mindset that you want to be in.

Brandon: Another approach is join a tech company in another role and work inside that company leapfrogging towards Product Management. Take your functional expertise, say you’re an Accountant, and join Shopify as an Accountant and then network and maybe you can work on x,y,z and leapfrog towards what you want to do.

Zhi: I think that’s actually the most common way for people to get a first PdM job where you get credibility internally first and then show an interest in product, volunteer your time to help PdMs. There’s always going to be ways that you can help out. So show your interest and curiosity around the product and eventually you’ll be able to work your way in.

Interested in building your own Product Management skill-set? Learn more about BrainStation’s part-time Product Management course offered evenings, weekends and weekdays.