Episode 4 – Jason Purdy – Go-To-Market Strategies

In this episode:

Matt Widdoes 

Welcome to Growth at Scale. I’m your host Matt Widows. This is a podcast for leaders who want to bring sustainable, predictable, scalable growth to their businesses. Every episode I sit down with world -class growth experts across product, marketing, finance, operations, you name it. The hope is that these conversations will give you real, actionable advice for building and sustaining company growth. Our guest today is Jason Purdy, Product Lead at Square. Jason’s here to talk Go -To -Market strategies. We deep dive into the life cycles of products and the importance of talking to everyone, but especially customers, when developing your Go -To -Market strategy. Welcome to the Maven podcast. I’m Matt Widows, your host and CEO of Maven .com. And today we have Jason Purdy, who’s here to talk to us about product. Jason, welcome. 

Jason Purdy 

Hey, thanks for having me. I really appreciate it. 

Matt Widdoes 

Yeah, 100%. So tell us about yourself. Who are you? What do you do? Where do you work? 

Jason Purdy 

I’m Jason Purdy. I’m a Product Lead at Square. I run the conversations team, which is really focused on connecting business owners with their customers. 

Matt Widdoes 

Okay, cool. And you’ve worked at a bunch of places. Walk us through a little bit of your history. 

Jason Purdy 

Yeah, I’ve been very fortunate to work for various companies throughout my career from the really small and starting my own companies to Apple, Yelp, and as I mentioned Square. I grew up in Cupertino, went to school in Santa Barbara, computer science, and mostly started my career making mobile games when the fancy phone was like the Motorola Razr, not to date myself too much. But you know, the I’ve heard of that. Yeah, the weird flip phone thing. And you know, the iPhone came out and that magical swipe to unlock moment was just amazing and it blew my mind. Taught myself Objective C and that’s really kind of how I got into product as I started a iPhone consultancy, making iPhone apps for larger companies and really fell in love with the full product development cycle. Really understanding what are my clients asking for? What are the needs that they have? And then starting from there and understanding, you know, what are the solutions and building products from there? 

Matt Widdoes 

So you started mobile gaming, which I had forgotten. And then you go into a consultancy at what peak iPhone days is that 2007? When is that? 

Jason Purdy 

Peak is an interesting word to use because every year is peak iPhone. Sure. But back then I think it’s 

Matt Widdoes 

Heyday. Is that better to say? In the heyday. I mean, it’s interesting to the shade that Mark Zuckerberg is getting for the metaverse. I mean, he’s making a big bet and, you know, the Apple iPhone was not exactly resoundingly approved by the market when it was first announced. You know, there were some really nice phones that were out from everything from Nokia and on up. So it was an interesting time. You know, the people who got it got it, but it was a very small market initially. I mean, even the App Store didn’t really show up until a little bit after the iPhone came out. 

Matt Widdoes 

So hold on, walk me through that because my memory of the iPhone. Now, granted, I was only six years old, but my memory of the iPhone was that it was like a powerhouse. I remember the first time I saw it and I was like, holy cow, this is like way different than anything in the market. I think the best phone at the time you’d mention the Razr. There were Blackberries. Yeah. People initially like, eh, you don’t need a video camera and a calculator in your pocket all the time. 

Jason Purdy 

Yeah. I mean, the first one had one of the worst cameras that you could buy in the market. 

Matt Widdoes 

Okay. 

Jason Purdy 

 You know, there was a Nokia device called the Nokia N95, which was $799, had a Carl Zeiss 5 -point -something megapixel camera. I mean, it was sweet. 

Matt Widdoes 

Which was unbelievable back then. 

Jason Purdy 

It was incredible. And of course, I had one and I showed it to my girlfriend and she loved it too or whatever. And then, you know, the iPhone comes out and, you know, it’s an Internet communicator, meaning it had a browser. 

Matt Widdoes 

That was the big thing. And Maps. Maps were, I think, did they have Maps early or no? 

Jason Purdy 

Yeah, I’m pretty sure it came with a version of Google Maps as my memory. There wasn’t like an, yeah. Yeah. And the Apple Maps came a lot, lot, lot later. But yeah, I mean, it was a small market. And the big thing was the price point. It was $1 ,000. People, you know, were like, who’s going to buy a $1 ,000 phone? 

Matt Widdoes 

Right. Yeah. Now that’s like every two years people have to have another one. That part’s insane to me. 

Jason Purdy 

Yeah. I would say it was probably somewhere between two and three years into doing iPhone development that I realized how big it was going to be. And, you know, the first few years, you know, not to go too far down a tangent, but my first client was Pabst Blue Ribbon. They were launching PBR Lite. And so my friend was, you know, his cousin was the CMO and we got in touch over a barbecue in San Francisco. And I built an app that allowed you to find PBR Lite so you could try it. And so it was, you know, an app that we built that had, you know, the map kit built on top of it. And, you know, it was pretty innovative at the time. But, you know, that’s kind of how niche and how kind of like weird some of my clients were. 

Matt Widdoes 

And now everybody drinks PBR Lite. 

Jason Purdy 

Everybody. 

Matt Widdoes 

So what other kind of apps did you build? I’m curious because, you know, this ends up taking you on a pretty amazing journey through Sports Illustrated in New York. Then you moved to Cupertino to work at Apple, which had to have been in many ways kind of a dream opportunity. You leave for, I think, a startup in between. You go to Yelp, which you did great work at Yelp. And now you’re doing some of the best work of your career at your current employer. So walk us through that. Like what other apps? Were there any crazy, I don’t know, goofy apps or like that was back when everything was so experimental where you’d build an app for light beer? Yeah. 

Jason Purdy 

Totally. We also built an app that was basically effectively catch. So kind of imagine, you know, Wii modes back then, you know, the Nintendo Wii. So you use the accelerometer in your phone and you kind of throw your phone. Hopefully you don’t actually throw your phone. And then the ball goes and then it’s the ball shows up to your friend, which could be on the other side of the country or the other side of the world. You know, a little kind of kitschy stuff like that was really fun. 

Matt Widdoes 

It was that remember the beer app was huge? The one where you like turn it? 

Jason Purdy 

Totally. 

Matt Widdoes 

And it like, it all leaves this people are trillionaires now. 

Jason Purdy 

And don’t even get me started on fart apps. 

Matt Widdoes 

And now I got to get started. 

Jason Purdy 

Yeah. And then I found a really, really good client in France and in Paris, a company called Quipit, which basically we took whiteboards and use OCR technology and digitize what you wrote on an iPhone or on a whiteboard and then it would show up on your iPhone. 

Matt Widdoes 

Sorry, what is OCR technology? 

Jason Purdy 

It’s basically you take a photo of a written piece of paper or in this case a whiteboard and then it translates that into actual digital text and it allowed you to basically using contrast and other kinds of filters. Basically we were Instagram before Instagram, but for whiteboards, Instagram for whiteboards. 

Matt Widdoes 

Instagram for whiteboards, that could be a deal today. So you leave the consultancy, you’re in San Francisco at the time, but then you move to New York anyways or you’re taken to New York? What happened there? 

Jason Purdy 

Yeah, I got a really great opportunity to work at the Associated Press and being in New York and kind of being the young engineering technical kid from the Bay Area was a really great opportunity to, you know, the tech scene in New York has come a long way since then. But at the time it was a lot of meeting people doing kind of very early stuff. It felt two, it felt three years behind Silicon Valley in a lot of ways. So just educating people about, hey, the iPhone is this thing, it’s getting really big and they have this new technology called in -app purchase and we should try it. Like why would we do this? 

Matt Widdoes 

This could be a thing. 

Jason Purdy 

Yeah, totally. So like after being at the Associated Press and helping build AP Mobile, which is kind of their first direct -to -consumer offering, I worked at Sports Illustrated as the director of digital and I’ll always remember my first board meeting walking in and just legitimately trying to explain to them the market dynamics of the app store. Like this is a channel that we could make money on. And one of the big challenges is that, I mean, the size back then at least of the print business from Sports Illustrated was hundreds and hundreds of millions of dollars. And you know, I’m coming in and being like, we could make four million dollars and they’re like, I don’t really care. So having to paint a picture that was a lot bigger about, yeah, maybe we make four million dollars this year, but I mean, this is 100. This is 300% growth month or year over year. If you think five years from now, if you think 10 years from now about where things are going, this is going to be a really big business. And that was a really big challenge to kind of paint that picture about where the digital system was going. 

Matt Widdoes 

To your previous point, is it your personal opinion that that is where the metaverse is today, roughly? I mean, it’s obviously much earlier. Are we pre -iPhone app store metaverse days? 

Jason Purdy 

The challenge with that is that I’m so biased with so much of the complexities that Facebook has kind of got itself into. And it’s hard not to be biased around some of Mark’s leadership and some of the decisions that they’ve made from how we think about free press and misinformation and other aspects of that. So I’m personally not super bullish on the metaverse. I think AR is going to be much bigger than VR. But again, as a product person, I always have to catch myself for that. I personally am a sample size of one. And a big part of that is, you know, I am very susceptible to motion sickness. I can’t go and watch a 3D movie, for instance, let alone wear a VR headset for more than 15 or 20 minutes. So, you know, maybe with some of the cameras inside the goggles and eye tracking and better motion sensors, maybe over time, things get better. So a person like, you know, I have an Oculus. It’s cool, but I can’t use it more than 10 or 15 minutes at a time. Right. AR I’m more bullish on, but both I think are have a long way to go to be proven out. 

Matt Widdoes 

So you mentioned, you know, being at Sports Illustrated, being an AP, you were also at Yelp after you left Apple. Yeah. You know, any insights on what you’ve learned, you know, in particular about kind of go to market and product strategy for those types of businesses? Are there any kind of lessons learned? 

Jason Purdy 

Yeah. I would say I learned the most out of any company I worked at Apple. And when you’re at Apple, there’s this whole Apple University thing that it’s, yes, part of it is around like, you know, employee training and improving your skills. But there’s also a very deep and consistent message around who Apple wants its Apple employees to be and how they think. And so one of the classic examples is there’s this whole hour long session at Apple University around how Sony did their TV remote and how the Apple TV remote. And then, you know, you put them side by side and the, you know, the Sony TV remote can swipe up and you have full touchpad and a whole keyboard and it’s got, you know, everything to control everything that you could imagine. And then the Apple TV remote, although the new one might have a couple of issues, but has, you know, four buttons. And this idea of simplicity, this idea of at its core, what is the thing you really need to do and wipe away everything else? And that was like a really, really big learning for me is from a product’s perspective because so often we’ll have really hard decisions to make in product. And like, well, put it in a setting, you know, we’ll default it to this, but if somebody wants to change it, they can go to settings and they’ll have a little tooltip and then like, we’ll make it really clear how to do it. It’s like, well, no, make the hard decision. Like, what is the good, best product that you think you can make? And it sometimes can be hard to make those calls. 

Matt Widdoes 

I’m curious, maybe more generally, when you start working for a new company, what are the fundamentals of go -to -market strategy that you always abide by? Are there consistent things across all? 

Jason Purdy 

First off, there’s a book called The First 90 Days, which I’ve read every time I started a new job. I’ve also read every time I’ve changed jobs inside of a company. It’s a really helpful reminder that the first thing you can do for those first 90 days is really listen to the people that were there before you. There’s a saying that anytime you get a new job, you should ask yourself, why does that job exist? Sometimes that’s because the business is growing and it’s a new opportunity. Sometimes that might be that somebody was there and it didn’t work out. The reasons can be different. But to remember that, hey, this job exists for a reason and they hired you for a reason and they’re looking for you to bring a certain set of skills and learnings to that job. First off, to listen to the people that were there before that somebody was doing that job before. It’s not totally net new. Then secondly, really talk to the customers and just be a lot more patient and not come in and try and make a whole bunch of decisions. The second learning from that book that I always take is try and find something very small that you can actually get to production that might be marketing language or a change on a website. That’s small. It’s just copy. But it shows that, hey, I have the ability to work the system, understand, okay, you’ve got a file, you’ve got a ticket, you’ve got to talk to this person. You’re showing you have the ability to execute. Those are the two biggest things that I always think about when I start a company or start on a new team is really listening and then try and find small things that you can do to try and show that momentum. 

Matt Widdoes 

What is the typical life cycle of a, I have an idea. I was thinking about it last night and I think we should add this whole other thing or this new flow or we should tweak an existing flow. What does that process from ideation all the way through final implementation typically look like? 

Jason Purdy 

I mean, coming all the way back to the beginning when I was running consultancy the number of times that I’d be at a barbecue, especially in San Francisco in 2009, 2010, “I have an idea for an app.” I have an idea for every single cocktail party, elevator, wherever. First off, I always start with whether it’s my idea or it’s someone else’s and the majority of the ideas don’t come from me. They come from the rest of the team is trying to understand, to use square parlance, the business owners that we work with, we call sellers. If we have a tweak to a sign up flow or we have a really big feature that we’re looking to add, we’re a communication software. Let’s say we want to add gifts. The first question is how do we validate this is something that the users actually want? How do we validate this is something sellers want? And there’s tons of ways to do that. So often I think we can get tied up in these week, three week, multiple month user research sessions where you’re setting up conversations with 10 or 50 people and you have a whole script. One of my favorite books is this book called The Mom Test, which I think is just, it’s a great name and it probably should have just been a blog post, but it’s a whole book, but it is really good though. The big part of it is you don’t necessarily need to do formal user research and a whole script and everything. Like go talk to a business out in the real world, buy a coffee and while they’re making your coffee, hey, how do you communicate with your customers? Oh, interesting. Would you ever want to send a gift? Oh, yeah, that would be great. It’s even just small little increments of validation can go a long way. And then the third one is surveys. I think I get a lot of them nowadays. It’s probably being overused, but it’s still a really helpful way to get that quantitative feedback as well as that qualitative feedback. And the kind of at the gist is this difference between qualitative feedback and quantitative feedback. I always love the early, early days because you kind of don’t really have either and you have to use a lot of intuition. But as you start, you have real users and you have an idea, it’s really helpful to talk to the people that your product is going to impact. 

Matt Widdoes 

And so how do you reconcile the gap between what people say they want and what they actually want, which is kind of unpredictable? 

Jason Purdy 

You know, Henry Ford has the, I think the quote, something on the lines of if I asked people what they wanted, they would have said a faster horse. 

Matt Widdoes 

Yes. 

Jason Purdy 

That’s why I love this book, The Mom Test so much. And so often when you talk to a friend or you do an interview like this, it’s like, yeah, it’s one of the more recent books that I read. So it’s kind of top of mind. But if I’m going to make a, I have this great idea to make an iPad recipe book. And I’m talking to my mom and she loves recipes and she’s got all the books in her kitchen and she owns an iPad. So like shoe in, right? But if you ask a bunch of leading questions are like, Hey mom, I your son, I’m thinking of building this, wouldn’t you love this? Oh yes, Johnny, I’d love to, you know, you know, the way that you structure the conversations with people in terms of understanding how they actually live their life. Sometimes you might have to kind of infer what the need that they might have is without leading them on too much. But that, that idea of leading questions is super important. I mean, you know, would you buy this? It’s like, well, they don’t want to hurt your feelings, you know? So they’re going to say yes. 

Matt Widdoes 

Right. Yeah, they’re sitting in front of you. Exactly. 

Jason Purdy 

But I mean, just to finish that though, I think the best question is asking people, what do you spend money on? And that’s actually speaking to their real behavior of where they do spend their money. That would be a much better question. 

Matt Widdoes 

You’re a published author and you creatively write on the regular. How do you find that time to stay creative? Does it help your other work and anything that you’re working on now? 

Jason Purdy 

I’ve had the pleasure with working with everybody from world -class designers to world -class engineers, marketers, etc. One of my favorite things in the world is when we do show and tell. I’ve done this on all the teams that I’ve worked with is not having show and tell just be pixels of a front -end engineer implementing something on an iOS app. Creativity comes from somewhere and seeing a designer in Figma real -time and how they can move around layers and experiment and show their work is just really inspiring. For me, I spend a lot of my creative muscle and energy on, it might sound really silly, but an email update every other week to the team that I forward to all of Square. 

Matt Widdoes 

Forward to all of, how many employees are at Square? 

Jason Purdy 

Well, so Square is part of block. I don’t know what the total number is. It’s thousands and thousands of employees. We have an alias call that’s just an alias at and you can easily unsubscribe from it. But a lot of companies have this idea of like, hey, this is an optional thing that you’re opted into by default, but of course you’re allowed to unsubscribe. And sometimes the history around it is that when Square was really small, any time there was a meeting, even if it was only two people, I think if it was more than two people, you had to take meeting notes and then you sent it to the whole company. But the bigger point is really writing it for the team. And I’m a big believer in forcing functions. And this every other week update is a forcing function for me to really go deep on all the things that we’re working on, understand where we are and the status for each. And it also gives me a chance to kind of tell that story about what is our team, what are our priorities, and how does this specific feature fit into that vision? 

Matt Widdoes 

All of that is so important because it gives people a sense for like, it’s easy to lose track of what we’re doing and like, why does any of this even matter? And some of those customer stories and some of those insights and other things are really, can be very inspiring and can be very, they’re like fuel to be like, all right, yeah, we’re doing this. 

Jason Purdy 

And it’s great to have that template for my weekly update that I write. I mean, it’s kind of crazy to talk about like, oh, what do you do for creative writing? I write an email, but it’s like, it’s true. Like I do spend a lot of time on it. And that template that I have, a big part of it is like, what’s the seller story this week? It’s like, oh, shoot, I haven’t talked to a seller in two weeks. And like it’s a reminder of like, I got to go and talk to somebody. So I have something for this email that I write. And it’s just a really helpful reminder. And the last thing I do is I include some kind of like, personal aspects around either what I’m reading, what I’m watching, and then usually, some photos of what’s going on in my life. And I’m a, it’s not for everybody. Not everybody does that. But I do include some personal aspects of how my life to just let people know kind of, what I’m going through and what I’m up to. 

Matt Widdoes 

You mentioned a number of books already on the podcast. You mentioned mom tests and you mentioned first 90 days. Any other books that you’d recommend? I love a good book, and I know you read a bunch and obviously you write a bunch. Other books that you’d recommend? 

Jason Purdy 

Yeah. Before even that, I think it’s important to talk about how does content fit in your life? For me, I really go out of my way to have this balance of more fun or more relaxing kind of content. It might be a good sci -fi book or something and something that’s more on the personal improvement or more on the work side. I always have the Overcast app and Audible on my phone and then I always have whether it be a physical book or something on my Kindle that I’m reading. I’m always balancing those.

Matt Widdoes 

 Do you read four things at a time and you go between them? 

Jason Purdy 

I usually have at least one Audible book on my phone if not two and then I usually have at least one if not three books in my Kindle and jump between them. 

Matt Widdoes 

It’s a lot. 

Jason Purdy 

Yeah, it is. There’s a really famous interview with Naval a long time ago and one of the things that that taught me was do not get stuck in a book. I was definitely that guy that would have a book on his shelf next to his bed for two and a half years because he got 100 pages in. I was like, this book is boring. I’m going to go to sleep. So I skip chapters all the time. I find if I go back to a book the second time and I’m still bored, I’ll skip ahead. Some of the books that I love and some I’ve listened to, some I’ve read, I’ll just go through a couple off the top of my head. First off, Good Strategy, Bad Strategy. I read this every year. We do a big annual planning thing at Square and it’s such a helpful reminder of how bad strategy can be. And similarly, a book that I think doesn’t get enough praise is one called Why We Sleep. And both of those, I think do a really good job more of teaching you why something is important because what happens when you don’t make it important or you don’t do it well. Strategy is a perfect example. Like there’s a famous example of a conglomerate canning factory and somebody takes it over and like, what’s your goal? We’re going to be 50% bigger next year. Okay, then what? Then we’ll be 80% bigger. And it’s like, well, growth is not a strategy. Like you might have a number that you’re shooting for based upon a certain strategy, but good strategy, bad strategy, I highly recommend it. And again, that’s that’s much more about like, what is bad strategy and how to find it? And there’s some good examples, but it’s more about that. And trust me, this is me to a T in my 20s. Like I would code until the sun came up and that was my alarm clock to go to bed, not to wake up. But we’ve had this sense of hard work kind of grilled into us. And I don’t think we take sleep nearly seriously enough. And I really hope people reevaluate why sleep is so important. 

Matt Widdoes 

100% agree. And I’m like fortunate in that I need, well, I don’t know if it’s fortunate or not, but I need nine hours of sleep. I get a lot of sleep and I’m not like ashamed of it. Now I go to bed at like 9 30. So it’s not like I’m waking up at 10 or something like that. But I just might I never deprive myself of sleep and I can’t function very well if I do. 

Jason Purdy 

And I really hate work from home. I’m a product person. I really miss those in architectures of the term called collisions, which is these natural interactions might just say the water cooler. But hopefully it happens more than just that. I really miss the office. But, you know, I’ve been to the square office after two and a half years. I don’t know, 10 times probably closer, maybe probably less than that. And I’m here on my couch. And I take two to three naps a week, at least I’m a good napper. I’m a real good napper. 

Matt Widdoes 

I can’t nap funny enough. But yeah, that’s good. I remember the days of napping and how a nice nap. My problem is if I nap, I’m now I’m like I’m a four hour napper. I’m not a. 

Jason Purdy 

Oh, yeah. No, I’m a 15, 20 minutes, 20, 20 minutes you’re stretching it. But yeah, 15, 10, 15 minutes, I’m ready to go. It just it resets the brain. I’m good to go. 

Matt Widdoes 

A lot of the people listening are early stage. They’re kind of call it series A, series B leadership. Any parting advice you’d give to kind of a leader or CEO, they just raise, call it 10 to 20 million. They have some new money in the bank one way or the other. They’ve got some product market fit. They’re just starting to scale any parting advice from your perspective that you’d say, well, hey, you know, if you don’t do anything else, do this. Or maybe a few bits of wisdom. 

Jason Purdy 

Yeah. There’s a guy named Rahul who started a company called Superhuman. And in some of his early days, he was doing a lot of podcasting to kind of get the word out around Superhuman. And he wrote an article on the first round capital blog really about product market fit. That speaks to it way better than I ever could. I highly recommend that. And then, you know, as you are in that stage and, you know, you’ve raised a little bit and you’re kind of thinking about like how to grow, you know, I always find that the best hires aren’t always the ones that I’m necessarily looking for. Like, you know, we had an amazing iOS engineer kind of fall into our lap and we didn’t really need another iOS hire. But it’s so often it’s the people that matter more than necessarily the role. That’s probably my biggest advice as I’ve grown teams and as I’ve kind of, you know, hired people throughout my career is, you know, the difference in somebody who’s good versus somebody who’s great is just so exponential. So that’s probably the big one. And then secondly, I love to just try things one percent, you know, doing a 50 percent A .B. test, we try all sorts of crazy stuff all the time. And, you know, there’s a big difference between the level of quality and detail that we put something even at 50 percent, let alone go into 100 percent versus something that we’ll try with our really kind of diehard sellers. So, you know, we set up this group called, you know, the messages beta group. And as I talk to sellers over the last two and a half years, you know, one of the questions I ask is, hey, would you be interested in being part of this kind of private group? And that’s where we ask questions. That’s where we, you know, post, hey, we have this new feature. Do you want to try it? And it kind of saves some of that risk and ability to kind of try things really fast and early. And that’s been really, really helpful for us as well. 

Matt Widdoes 

Awesome. Well, Jason, thank you so much for joining us today. It’s always a pleasure to speak and I look forward to next time. 

Jason Purdy 

Yeah, thanks so much. See you. 

Matt Widdoes 

All right. Cheers. That was Jason Purdy talking about go -to -market strategies. Thanks for listening to Growth at Scale. Check back soon for more chats about growth. Find more episodes, conversations and blogs at MAVAN.com. See you next time.