Interview: Matthew, Head of Product

I wrote my first post on this blog on April 9, 2013. To put it in perspective, that’s nearly a decade, and I’ve published an article at least once a month. Perhaps it’s not strange then that I occasionally think I’ve run out of things to write about. But even if that IS true, it doesn’t mean there’s nothing new to tell. So for the coming weeks - or even months! - I’m going to try something new. Rather than me doing all the thinking and talking, I want to invite people I work with, people I admire, to share their thinking. You see, I’ve been fortunate to work with some insanely smart people with views on many different topics. So I invited them to tell me - and you - more about their work through their unique and valuable lens.

Another reason I want to do this is actuation because of one of my most popular posts. In “Working as a UX Lead”, I was able to share what I do and how I approach doing it. I’ve heard from others who had recently been promoted to UX Lead that it can be pretty ‘muddy’ as to the expectations of the role, even for the company they’re working for! So these next couple of posts will be me talking candidly to people about their role(s) and what that actually means to them and their companies. First out of the gate is Matthew Woo, Head of Product and Co-Founder at Summer Health. I’ve been fortunate enough to work alongside Matthew for the last few months, and he embodies something that I rarely experience. If you make a venn diagram of really smart people and really empathic people - Matthew is in the center of that diagram. Read on!


Matthew Woo

Anton: Hi, and welcome! I want to give you some context before we begin… One of my most popular blog posts that I wrote that had a lot of engagement is about working as a UX Lead. Many people reach out to me saying, “I was just promoted to UX lead in my company, but I don't really know what's expected of me in that role.” In this industry, as well, like, we have a ton of positions that are not always crystal clear on what you actually do. Obviously, there are differences from company to company, but the idea of this series is to create opportunities to talk to different people in different roles and hear a little bit more about what it is that they actually do in their current roles. So let's get started, and we'll do a quick intro first.

Matthew: Sure, quick intro, my name is Matthew will have been in product for the past, I just feel old when I say this, I think almost 10 years now. I started my career at a company called meetup as APM. And then from there went to a variety of startups, including a stint at a company called yo, where you’d just sent a notification that said, “Yo”, and then most recently, prior to Summer Health, I was at WhatsApp. And now, I'm the co-founder and Head of Product of Summer Health where we're trying to radically simplify access to health care, with a focus on pediatric care first.

Cool. So what would you say brought you into this role? Being a co-founder changes the dynamic a bit, but what made you want to take on the role as Head of Product?

First, I come from a very entrepreneurial family. So, obviously, part of it was new, starting something on my own, and in this case, joining something at the very early stages as a Co-Founder. I think the second thing was coming to be the Head of Product. I think, for me, it was because I had met Ellen early and got to work on the product at the early stages and build things in an early prototype. What convinced me was that even with a really terrible prototype with no login experience and just people messaging a number to get help, I saw the impact it was having on people's lives. So I was like, wow, this is a real problem that needs this solution. I had one parent share with us that she spent four hours trying to get help and was about to give up and just drive for the extra two hours to urgent care. She was lucky enough to find help through this and was able to triage the situation herself. She then understood that, hey, it's something that she could deal with in the morning, and that was a huge lifesaver for her. A third thing is probably just a bit of a quirk of mine. I'm very opinionated about the way products should be built. I really wanted to be able to build the type of culture and team that I thought could help provide the most impactful way to deliver value to people. That's really at the essence of what product is all about. Solving the right problems for the right person at the right time.

What would you say is the difference between being Head of Product versus a Product Designer?

One slight point of clarification, I'm more of a Product Manager than a Product Designer, and I am definitely not talented enough to be a Product Designer. But I think the biggest difference between a Product Manager and the Head of Product is that as a Head of Product, you have to constantly think about, what the long-term vision is. Where you need to get to, where you are now, and what immediately needs to get done. Sometimes, from the Product Manager's perspective, this obviously depends on the company, but you can be more focused on what needs to get done next. As a Head of Product, you need to have a multi-year type of vision and a strategy of how to get there. This is the biggest difference, from my perspective. So I know this isn't the most popular company right now, but Meta/Facebook did a really good job of fostering Product Managers to have more founder-like tendencies. It was a bottoms-up culture where you could talk to your director and be like, “I think there's a billion-dollar opportunity here, and here's the three-year plan to get there.” There was a sense within Facebook that if you can't get to a billion dollars in GMV, ads, or users in the first two years, why bother trying? So it really forced me to practice that big-level thinking, and that's only carried over here as well.

And so how do you, on a day-to-day basis, balance the things that you think need to be done now versus working towards that long-term goal?

I think the way products should be dialed in is by working backward from where you want to get. So, when I first joined Summer Health for the first two to three weeks, Ellen and I spent a lot of time together, thinking about what the vision looked like. What does it mean for the caregivers on our platform? What does it mean for the providers? If we succeed in the next three to five years, what does each of those milestones look like? And working backward from that, what would have to be true for us to get there? Only then did we know what to focus on now.

It helped us always think about, what is the next biggest question we need to answer was. To know whether we're on the right track or not. The reason why I mentioned this is I think that's an exercise people should probably do on a biannual basis, always revisit, what's in your three to five-year time horizon? What's the new set of information, and where are you now? Are you on track, or do you need to change your strategy or roadmap to get there?

This is how I balanced between, thinking about the long term, but also constantly making sure that we're focused on executing in the now. What you want to avoid is a situation where you have a good strategy but bad execution and, therefore, you can’t even tell if the strategy was wrong or the execution, and you'll never be able to launch a good product that way. But if you have excellent execution but a mediocre strategy, you can still build something. Okay. So that's kind of the way to think about it in some ways to balance between the two.

Yeah. Makes a lot of sense. I think it's interesting that it's often the seemingly obvious things, but a lot of companies fail at them. Still, what would you say? What are the characteristics of being a great Head of Product or even a great Product Manager?

I think it boils down to a few things.

  1. One is having a perspective and vision of what the world should be and why it's important. The reason why it's so important, not to sound like a broken record, is that it's the only way to align everyone to make the right long-term decision truly. It helps resolve short-term conflicts and the politics come up when it comes to trying to build things.
  2. The second thing I would say is if you can have a strong vision, then you constantly have to fight for that alignment. You need to constantly remind people, what we are doing and why we're doing it since you want to empower people to make their own decisions. Being a great product leader doesn't mean that you make all the decisions, rather, it’s that you empower everyone to make the right decisions for the company in the long term. So you are constantly driving alignment, what that practically means is having clarity of thought in what you write and how you share those ideas by constantly repeating it. People will probably say it's annoying, but I will constantly be like, ‘here are the top priorities for you, here's how we're doing about it, and here's why it's important.’ I think that just helps make sure that everyone's moving in the same direction.
  3. That leads to the third point, which is communication. Be very concise, clear, and explicit in what the team is focusing on and why, and the trade-offs that you're making. I think that is incredibly important. What you don't want to do is be afraid of communicating because you're worried about how people will judge it. It's better that you put something out there that is half-baked or not ready and get feedback than to have it all in your head and surprise everybody at the end. So communication is really important.
  4. That leads to the fourth point, which is collaboration. By having strong communication and communicating often, you can truly foster a team environment with collaboration, where people feel that they can share their thoughts early. Honestly, as a Product Manager, I think it's a false belief that you're the CEO of a product. You're not. You're there to help bring together the best ideas and foster thoughtful discussions on how you build the right product for the right person and solve the right problems.
  5. And then finally, whether it's your team or your customers, you constantly need to be, extremely empathetic and constantly listening. That helps you make better decisions. And so I think that's the five things I would say, alignment, empowerment, efficient communication, collaboration, and empathy.

Cool. Yeah, it's fascinating to hear this as well because it does come across as something that you’ve spent a lot of time thinking about as well. And, you know, being fortunate enough to work together, I can testify that this is how things are run and, despite having worked with a ton of startups as well as a lot of very large corporations, I don't think I've ever been in working with a company where priorities are this clearly communicated. It's really valuable just to get that alignment and direction constantly.

Awesome. Well, thank you for the kind words, I'm sure I could be doing it better, but it's a hard, hard, hard-fought lesson from times when I didn't do that and, things fell apart. So I’ve learnt it through trial and error.

So what would you say, if any at all, is the difference between designing and making consumer apps, like some of the health and some of the business-to-business things that you've worked on? At WhatsApp, for instance?

I think that the biggest difference between the two is, for b2b or SaaS like companies, it's a lot more clear what the problem is that you're solving. Then once you solve it, the benefit is almost immediate. Whereas for consumers, I think the difference is that most consumers are not making decisions that drive some incremental revenue or some immediate benefit. So for a lot of existing solutions, you're constantly competing with a default case, and a lot of the products and experience that you build is basically for a change in behavior. Sometimes is more difficult to know, especially at the early stages, if you're on track. One thing that I have noticed is you have to be extremely patient but constantly be talking to your users day to day to understand how their behavior is changing. You can either reinforce positive behavior, which is obviously engagement and also lower the barriers for situations where you're creating friction.

So, what are the top three things you spend your working days with, and they can't be as vague as meetings?

So Anton probably knows this about me, but I am an extremely early-morning person. I start my days at 4 AM, and I go to sleep at 8 PM. So it's not like I have this crazy, ‘I don't sleep’ type of situation; I just sleep early because I'm old. I think what I love to do in the morning is all my longer or deep work.

I split my deep work between a few things. One is thinking about the immediate product experience or features that are coming up and just going through creating UX flows, thinking through the different edge cases, and providing context of particular problems for the team to solve. The reason is that some of these things can take longer than you expect. Sometimes I'll write a PRD, and they'll take me twenty minutes, and sometimes it will take me an hour and a half to two hours. It's this unbounded thing. The most important thing is that I am being thoughtful about the experience so that when I talk to the team, we can focus the conversation on the key trade-offs.

The second area I spend the morning time is thinking a little longer term. This is probably a little bit more related to being Head of Product. Just thinking about, given our current trajectory, will we hit a particular milestone or the objective that we have? For example, in our case, raising a Series A and, if not, what are the other areas that we need to investigate to identify new opportunities?

And then, I think, the third thing that I spend a lot of my time with, honestly, is meetings and collaborations where we jam on different ideas with engineers or designers.

The last thing I'll say is that most of my time is just talking to customers. I try to schedule like three to four hours every week just talking to caregivers and providers that use a product constantly to understand how we can get better and identify emerging and changing behaviors as a metric. Consumers are very fickle in some ways, so you always have to be on the ball. It's not something where you figure it out once, and you can kind of leave it. So that's how I spend my time.

With you being an early morning person located on the West Coast, there's a nine-hour difference from me in Sweden. Since my partner works in a restaurant - starting work at lunch and working until late evening - it makes it, so your and mine days are pretty much matched despite the time difference!

Can you mention if anything particular comes to mind, something surprising, that you‘ve learned from a customer call?

Yeah, I think that’s one of the things that has surprised me the most, and I’ll stick to my experience with Summer Health. I think that it's fascinating talking to caregivers about Summer Health. The interesting thing that we found was that it was not that they didn't have access to good quality care, meaning their pediatrician, but the speed at which we provided a response changed their behavior. So, at least in the US, reaching out to your pediatrician with a question may take a couple of hours or maybe as quick as 30 minutes, but if you're at the pharmacy and you have a question about what medications you should buy for your child, you're not going to want to wait for an answer. You might just put off the purchase. But with Summer Health, you can message somewhere and get a healthy response. I think, on average, we respond within three minutes. And now they're like, oh wow, this is something where, when I'm on the go or in a rush and the kids are not feeling well, I can message someone for a quick response. That changes their behavior.

I think the second thing is that we're asynchronous because of the way we incentivize providers. We pay them on a per-visit basis, and that changes the way that care is delivered; it's no longer time-bound. When going to visit a provider in person, it's usually scheduled in 15-minute blocks because that's how our doctors are paid. In contrast, our providers can talk to multiple people at the same time and not be stuck in a billing-mandated schedule. They love the fact that, like, they don't feel like they need to finish a conversation in just 10 minutes or 15 minutes. Some of our people talk to our provider over the course of four hours, and it doesn't cost them anymore. You feel that Summer Health is now a companion and not just a service. I think that's another really powerful thing.

Sometimes people use us to basically replace Google and get a quick, reliable second opinion. So they'll have their own pediatrician log an opinion. Then they're like, ‘I want to be cautious and just use Summer Health for another opinion, and it only takes two or three minutes.’ So it's been interesting learning how the modality being text messaging and the speed at which we deliver services has really changed the behavior of caregivers who already have a good relationship with the pediatrician but still find reassurance in that second voice.

Ok, one last question. What would you say is the one tool or thing that is the most useful or critical to you in your profession? I know that you're, at least to me, it feels like you're a Notion power user. But anything else you want to highlight?

Yeah, so, like a tool? Is that the question? Or could it be a framework as well? What I think it comes back to is the most important thing a product manager needs to have. It comes from listening to other people to create an informed perspective of where the team needs to go and why. Having a very concrete vision.

This reminds me of an article that was sent to me. There is a PM at Shopify, his name's Alex Danko, and his belief was that it's not everyone's job to sell. It's everyone's job is to world build. If you're just trying to sell, you're just trying to sell someone something, but if you're trying to build something, you realise that you need to build a very concrete description of what that world is like so people can make all the micro-decisions needed to bring that world to life. And they think that's been super, and it sounds really cheesy. And it's probably very similar to Amazon's newsletter headline that you write when you first come up with a project but really working backward from what that ideal customer experience just simplifies so many different things because if you start from a pure bottoms-up approach, there's just too many different pathways and people are often afraid to commit to one because what if it's the wrong one? If you can start from the back and have the vision - while, yes, it might be wrong - but if you can convince enough people that is the right place or you've learned enough and have the conviction that it's the right direction to go. It's what is needed to get started, honestly and it's helped me remove a lot of the paralysis that I used to feel when I tried to go for the bottoms-up approach.

Thanks a lot, Matthew. This was awesome. I know a lot of my readers will find this super helpful, so thank you. Speak again soon!


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