BUILD

SUCCEED

‍David: Welcome, Pierre. Thank you so much for joining us on Build to Succeed. How you doing today? 

Pierre: I'm doing well. I'm doing well. Thank you. 

David: Awesome. Let's get it started. I'm doing? great. Thank you for 

asking. can you, uh, let's start by maybe just giving an introduction. Introduce yourself and give us a little bit of your background story. 

Pierre: Yeah. Um, so my name is, uh, Pierre. Benz, I live in cloudy Port Oregon in the Pacific Northwest of America. I. and I am an engineering manager at, uh, Headspace. Headspace is kind of like known for a meditation app, mental health app. and I've, I've been here as part of the engineering organization for the last, just over three years.

I started my journey at Headspace as a iOS engineer. and, slowly but surely and [00:01:00] steadily kind of. Grew there and I'm now leading, I'm the manager in the team that is busy converting the app, exciting me to Flutter. 

David: So tell us, how did you get into tech in the first place? 

Pierre: you know, that's a good question. I think my love, in tech or technology probably came from an early age like I was. You know, one of those kids who grew up with video games, 

and just loved playing them. Unfortunately to my, dad's dismay, you know, he always kind of saw them as like a absolutely waste of time.

but got into just video games and wanting to make video games. And I remember like the first, one of the first books that I bought was How to Make a 3D Game Engine with C Plus out of all Languages. and I think like out of that came my love for tinkering with technology. I think like At a young age, maybe like, 13, 14 decided, hey, I didn't want to be, in my dad's windows computer. 'cause I kept on breaking and formatting things. got a Linux machine going up. I think I started with Linux from scratch and gen two. and I think my love for just tinkering and breaking things and messing around and [00:02:00] understanding how things work, uh, really started there.

ended up going to university studying computer science. and even there, my, my path was about, you know, making games. I think like undergraduate over there was about game development . And in that process I learned, you know, the very early on, you know, when I'm surrounded by so many clever people that could like out program me, in their sleep, I learned that I had a, I guess like my focus at that point was about understanding why do people.

Use technology, I think more so than the technical aspects of it. and that kind of took me in my career, over there as, doing postgraduate studies, really trying to like mesh, how does technology and psychology kind of intersect. and then I had a kid, and you know, at that point doing computer science at the University of Cape Town in South Africa.

And then I had a kid and that kind of like. and with a whole bunch of other stuff with supervisors and stuff like that, ended up moving to, the US and jumped on the [00:03:00] thing that I could do at that point, which was make apps. at that point, like my, my, dissertation was about, I think we were doing Android apps and iOS apps, and the easiest thing for me was like, okay, I, this is pretty easy for me to do.

I'll just make some iOS apps. Then slowly progressed in that career. went into startups, went into IOT devices, went to a design agency, A KQA, for a bit, and then more,agency life or startup life. and then I think like halfway through the pandemic, you know, I was at a startup that unfortunately had a close down, and.

I found myself knocking on the door again. I, surprisingly enough, interviewed at Headspace before and didn't get in and then interviewed again. and I was, luckily, unfortunately,got in, and in that scenario I was like, you know, also one of those, it was one of those moments where I was, just I guess through my own, how do you say it?

Like through my own, I think we all kind of went probably crazy in Covid, so probably in own, um,ability to kinda like find what do I want to do with my [00:04:00] skills? Headspace was a no-brainer for me. I'd used the app, I think I was a member since 2016. a Headspace user. it definitely helped me in patch in my life.

 and I think the pull to try to use technology for more than just. Solving an itch. that was kind of the drive there. and then I joined Headspace and, have been on this kind of crazy wild ride, for the last three and a bit years. And as I mentioned, I've been there from just an individual contributor to now, needing a team that's busy transforming how we're viewing our apps and our technologies over there.

Yeah. 

David: gave us a nice roadmap of things to talk 

Pierre: Yeah. 

David: Um, before we get into the Headspace stuff though, and what you're doing and some of that journey, I wanna go back to one of those things about the video game stuff. 

Pierre: Yeah, 

David: me, asking about that, 'cause you have kids, how old are your kids? 

Pierre: I have, yeah, I've got a 9-year-old and a 6-year-old. 

Yeah, 

David: given your exposure to video games and the influence that had, what's your strategy for technology and video games for your kids? 

Pierre: it's a good [00:05:00] question. if my kids have or are gonna listen to this, like unfortunately they have a bounded, they have a very constrained window of. Access to, games and technologies. I definitely, like with my son in particular, and probably with my daughter's, the, the 6-year-old of my, my son is a 9-year-old.

you know, I think over there I've learned, from myself that, as with most things, like it depends on the attitude in which we approach them, right? Like, so, so for example, with my son, I'm now in a place where I'm like, Hey, I have this. Library exposure that I've had to, here's a taste of this, like, do you like this?

here's a different one. he right now is really enjoying, legend of Zelda. think he's just finishing Breath of the Wild and he's gone down his own rabbit hole of reading the game guides and reading the books. And I think for me, the thing that I'm trying to cultivate in him in particular is persistence .

Like, you're gonna, you're gonna confront things in your life bosses scenarios where I. you're not gonna succeed the first time. And instead of just giving up, like, [00:06:00] can we cultivate persistence and grit, like in particular, you know, for him. so like he's on his own journey and you know, he's constantly asking me for, more games.

I haven't quite gotten, like, there's a whole genre I'm discovering like, as a parent, you know, you kind of put your kid in, in the wild at school and they come up with their own social, game exposures and what's really big for them are these kind of like horror games where you're being chased by something, which you know, clearly is speaking of.

Probably some other unconscious things that are going on in their lives as they're grappling with things that are scary and being chased and how to navigate that. So we haven't quite gotten there yet, with him. I think like maybe as a 9-year-old, I'm not quite gonna expose him to that. but I think some of the other games, like, like I mentioned, legend of Zel suffered.

We, we is being heroic and trying to overcome the, insane odds with our character is brought in. I'm like, Hey, this is. Is really great. And on, on the flip side, you know, he has like dived into [00:07:00] getting those game guides and it's like, like giant books, this thick reading them cover to cover without me having to prompt him.

And, you know, inadvertently he's, an amazing reader at the moment and, uh, really had little to do with me saying, Hey, you have to read these type of books. It was more like, find your interests, let's encourage that. Let's explore that. And he has himself discovered, the things that he enjoys. So 

that's worked well with my daughter on the other end, like she is, you know, she has, she's growing up with an older brother who's playing all sorts of games and she's starting to read now, and so she's starting to navigate games and what it means and what are things and learning instructions.

So she's in our own journey. She's not quite enjoying the fighting games as much. So she enjoys like the more, boating games. The, there's a whole spectrum of cooking games and stuff like that. and you know, but they actually both enjoy the untitled goose game, which, it's a lot of fun just being a goose and, you know, stealing keys from a farmer.

[00:08:00] Uh, but 

yeah. 

David: fun. 

Pierre: Yeah, Yeah, it's a lot of fun.

David: I think the games, why I wanted to ask about that is, you know, a lot of us grew up playing games. I, not to date myself, but I grew up playing tethered to a TV with a 

Pierre: Yeah. 

David: system, you know, super Mario and all the things that came with that. and then going through that journey and, you know, wouldn't, when you get a, as a parent, there's this thing of like, okay, how much are we gonna introduce? More screens there to have tv, all these other things. 

Pierre: Yeah. 

David: I have just found it to be like, just such a massive improvement over tv. Like if they watch a TV show, they're just like zombied, But when they play games, they're solving puzzles. They're thinking about, Yeah.

details. My daughter's the same way. She's got this book that's like two inches thick about this tears of the kingdom, 

Pierre: Yeah. 

David: thing like memorized 

Pierre: Yeah. 

David: Where I've been seeing it being really creative from the perspective.

'cause you, for you as a pathway into tinkering and getting to become software engineering, like how did these things work? they like to watch YouTube videos and they found this glitch. Turns out it does work. Like there's duplication glitch, that if you follow the sequence of 

Pierre: Yeah. 

David: you can somehow, like, you know, make five [00:09:00] more of the thing that you're holding just magically.

It's literally a glitch. And so I think like, but they've discovered these things. They find these things and then they start thinking about like, why that might be happening, right? Like, oh, well 

Pierre: Yeah. Yeah. 

David: like. When whoever wrote the game, they didn't properly handle this scenario. And the counter that's keeping track of how many items you're holding is out of sync with like the actual items out of your inventory.

Pierre: Yeah. 

David: there's a, it's a legitimate bug, you know? So it's been really fun to find those things. And I just think collaboration wise, it's such an interesting thing like that these kids are, capable of exploring these worlds and all the creativity that comes with it and the hero's narratives and all those sorts of things. and I think still today they get scoffed at a little bit, but I think that. They're really important, can be really important parts of someone's journey to even what they do professionally one day.

Pierre: Yeah, I mean, I think of like, just the act of self discovery that they're going on. You know, like, I think like before legend, I was out. My, my son was into like just Minecraft and. I don't think he really enjoyed the survival aspect of it. you know, of like, hey, like I've gotta, you know, at nighttime these things come out and [00:10:00] that's scary.

Like, but he really just enjoyed the playground aspect of, Hey, I'm gonna put these things together and, see what happens. and you know, for us at least, we have some constraints. I think, like, you know, I'm probably on the one spectrum of like 20 to 30 minutes a day where he can play whatever he wants to play, you know?

But the. Offscreen that's still continuing. Like we have a giant, he in particular has a giant Lego thing and he is consistently and constantly boating worlds. you know, we, we've got a, his room and his floor is just about like boating these platforms and stuff and role playing and doing all this type of stuff.

And, I'm slowly but surely getting him into d and d 'cause that's one of the things that I grew up with, as well, which wasn't. I think he enjoys the physical aspects where d and d for us was more mental. but it is, it absolutely is a, I think anything that, that we can do to, I guess as parents and as caretakers, is to participate with them [00:11:00] and growing that imagination.

And I think that's the fun thing, right? Like that's what games do is, Hey, what if I do this? What if I do that? and the games are a little bit more sophisticated to. Respond to your input. I think back in the day, ours were, quite, maybe not as sophisticated, but it was enough for us to want to be in that world.

Pierre: you know, but sometimes there's a danger, right? 'cause like you have that aspect and I'm sure we all are aware of there is the act of escaping that is there in present, or that is there in these really highly livable and breathing worlds. You know, where there's, I guess every parent has that tension of like.

I don't want you to miss out on life while you're enjoying this other life that you're creating. And they're, they both are lives to some degree. alive in our kids' lives, and so they're part of life. but it's that balance. I think that's the biggest thing I'm trying to kind of bring to my son is like, enjoy your games, balance it out with the other things in your 

life.

David: we're, uh, this is about technology and

Pierre: yeah. 

David: and [00:12:00] all those sorts of things. And so people listening to this point be like, all right guys, come on. You're talking about kids. Like what do we, but here's the thing. This is, you're not the first person that we've talked to that, Um, we get into something about kids, right?

And what it's like to be a parent. And in a way it's a very specific type of managing an engineering process in a way, right? All of the things we just discussed, you could go back and re-edit and talk about what it's like to be, to develop yourself in a professional 

Pierre: Yeah. 

David: your passions, finding things that you wanna like, consume voraciously, right?

Like you find that thing and you wanna read the book, you wanna get onto it. The balance between the two types of life. You know, there's your work life, there's the thing you're building, there's all these opportunities. And so I find that some, one thing interesting about. Parents is like not trying to compare managing people to managing a child.

It's very different, obviously, or managing a product or doing the work we do professionally. But one thing about being a parent is like you observe these behaviors that are all inherent to all of us, but you observe it in a context of somebody who, for them it is totally new. 

Pierre: Yeah. 

David: new and it's eyeopening.

We [00:13:00] learn new stuff all the time as adults, but it doesn't feel as like shockingly amazing as it does to a 9-year-old or a 6-year-old, right? So 

Pierre: Yeah. 

David: of being able to observe that learning happening in real time. And I think that kind of helps us to, mature a little bit and think about like, how do we bring this, some of these things like patience or how do we, um, figure out how to guide behaviors or certain things or. how to like, like really harness your passion areas and stuff. And I've always just found that really interesting. what sort of being a parent allows you to do that you can bring into your life and other spheres. so Yeah.

Pierre: Yeah, I mean, I, you know, I think blessing and the curse of being a parent and a manager is like, oh, you just never switch off. you're constantly place of, maybe being overstimulated, maybe being overwhelmed, maybe having to kind of put a lot of things out.

But I know for a fact that being a manager has made me a better parent, and being a parent has made me a better manager. in, you know, and definitely know in, earlier in my career when my kids were a lot [00:14:00] smaller, I particularly think of my son, you know, when he was a baby, I probably did not have the empathy or the, I don't know.

Like I didn't have all the tools that I have now raising a 9-year-old, 6-year-old back then. so I'm very fortunate enough that for me. I know there's some other people, like I work with some people, like my manager right now, she doesn't have kids and she blows me away. Right? And so, but I know for me at least that in my journey, both of those have helped me become better at both aspects of my life.

you know, and so that's, I'm fortunate for that.

David: Yeah. And

Pierre: and 

David: a leader, as a manager, like that. empathy and building that, whether you get it from, being a parent or some other thing that you learn or mentorship or other

Pierre: yeah.

David: and

I think you're right. It's like we're not saying to be an effective manager, you have to be a parent. 

Pierre: No. 

David: one's saying that, 

Pierre: No, 

David: but I 

Pierre: no. 

David: um, you know, paying attention to those things.

And I like just looking for those signals of like, what are the things we can learn as leaders as we grow in our career? Where can we draw pockets of inspiration? It doesn't have to be a business book that you buy in the airport, you [00:15:00] know, it doesn't have to be, something you would do as a parent.

It could just be like a random observation walking down the street of sea, somebody does an act of kindness and you think about how do I connect that back into a. Making a difference in the world and what I do on a regular basis. so it's using that. let's take some of these ideas from what it's, the things we've talked about, 

Pierre: Yeah. 

David: empathy and, finding passion and exploration and all those things.

Let's fast forward it to what you're doing at Headspace. I know you guys have been through a bit of a product journey. I know there was an acquisition mixed in there and, maybe it takes us back to like, whatever you think the appropriate beginning of the story is that kind of gets you to where you are today and give us a narrative. 

Pierre: Yeah. You know, so interestingly enough, I joined Headspace exactly when the merger of Headspace, the, iOS and Android app and Ginger. The, back then it was the Flutter app, which was mainly more about coaching and therapy. I joined right when they came together, and. I witnessed, you know, two companies try [00:16:00] to figure each other out.

two companies having, you know, working through their silos and integrating over there. and I would say that it was definitely eye-opening it, you know, having those scenarios and also having the directive of like, Hey, we want to get under one house, so we need to be in a place where.

We are not fragmented, or we don't have, we don't have to split our teams in multiple ways. But, you know, again, I was coming, when I joined, I was coming in as a iOS engineer. So my focus was mainly on iOS. somewhere in the journey that, you know, the product vision was, Hey, we don't wanna have separate apps.

We don't have a, just a legacy Ginger app or Headspace Care. I think we rebranded it there and Headspace, we wanted to bring it into one place because. I don't think people wanna have different apps when they switch to things, they want to have a one place where they go and do things. and our journey began with, hey, bring in the core functionality of the Ginger app into the Headspace app.[00:17:00] 

And historically at that point, that was a Flutter app, you know, through and through. And now we needed to, uh, to some degree like add. Add that functionality in there? I think internally we called it our Frankenstein moment or our Frankenstein things because we absolutely pulled it off. like my hat still goes off to all of the engineers and the people that were involved in that one because it was an insane feat, for us to do and for Headspace and for us, like we, we do have, sometimes when you're in the healthcare space, tight deadlines and they're oftentimes.

January 1st, right? Because that's when healthcare plans kick off. And so we have these kind of like, at some scenarios, and particularly for this one was one, one, that's your deadline. make it happen. and so, you know, heroically, we did that and we launched it and it was a success. But now we had more problems, right?

We had our legacy iOS and Android apps, and now you had this flutter. Shared library and this fluter component. [00:18:00] We had it in a scenario where it's like, this is a shared SDK that we are using in three different places. We're using it, the Headspace app, we're using it the Headspace Care app or the Legacy Ginger app.

And we're using some of that code in like a web scheduler that's more on the front end side of our 

clinical team and our coaching team. And making changes in one place took a long time. We had lots and lots of, just integration issues. And again, this was, our first, Hey, get it in there, you know?

And I think for many of us it was, like see what happens. and then, I think come coming at the end of 2023, or the last quarter of 2023, it was myself and a group of other. amazing engineers. We were tasked with the act of like, okay, well investigate what it would mean for us to go full flutter.

and we gave our recommendations. I think for many of us on the native side, egotistically, we were no, let's not do that. because we wanted to, you know, we had our own roadmaps, [00:19:00] right? Like we had our own things that we wanted to improve. We were just starting to work on, at least on the iOS side, we had maybe like 40% of stuff in Swift ui.

There was a whole bunch of, a whole bunch of stuff that we wanted to do. And all of a sudden you get this side conversation, which, for us it's like, you know, I've been around long enough to know that hey, like don't wanna do React native. I've done that before. I don't want to, all of these other things come with other costs.

we are just trying to kind of. We're just trying to land this plane and move in a way and scale this. and so I think, in retrospect, and that's not, I think our CCTO Vic, at that point, he made the right call, which was, you know, looking at the big picture of technology of what we're trying to do as a company, which is make mental healthcare affordable, scale.

get onto multiple devices, et cetera. Like with all of those other things in place, the preferences for the engineering team as much as what they need to be considered, they need to [00:20:00] be considered within the largest scope of things. you know, and, trust me from the native side, we tried everything.

We tried getting it on the, performance side, which, you know, there were some considerations that we had to do, but none of them were. Breaking, on the UI side, like, Hey, can it really match the native standpoint? Like, we try to kind of go from that route also really didn't move the needle as much.

 and then, you know, then came the hard goal of, okay, we are making this decision. Here we go. whoever is on board,I remember. From our perspective is like, Hey, this is the decision that we're making. It makes business sense. we can't be in a place where, at that point Headspace was still like, Hey, we're we have a limited amount of engineers.

I think everyone has limited amount of engineers, right? we're not just overflowing with engineers, we have limited capacity, uh, limited resources. but we wanna extract, we want to get value to people, right? And one of the biggest hurdles that we had was the ability for us to be feature complete across all [00:21:00] platforms.

So say, you know, you play a meditation or you sign up and you buy a subscription on the web, you're buying a subscription for features that you want to be able to have on iOS and an Android. And I don't think we had that parody feature parody. And that is one of the things that obviously, like when she's centralized to a different platform where you can build and your features are over there, it's a lot easier for us to kind of expand and provide those features to all users.

and yeah, that's kinda what started that journey for us was like, okay, we are gonna make that decision. And what has been part of my life now for the last year and. Year and four months, five months has been migrating the existing surfaces that we have, be it the players, explore profile, all those type of thing, onboarding, migrating that to flutter.

and it has been a journey. I'll tell you that one, it hasn't always been straightforward, but I definitely can see like, you know, one of the benefits of this one is that for us at least, [00:22:00] it has solved that silo. You know, before we had, you know, Flutter engineers and native engineers and native Android engineers.

And part of that getting together and building something really has, from my perspective, really helps solidify a cohesive team. the trick now is to make sure that team expands and that the knowledge that we're sharing and the comradery and community that we are growing over there and the culture and ethos that expands outside of the walls of our team that's busy.

Migrating it because we haven't quite said, Hey, pause on everything, while we are migrating this. Like, it's one of the, one of the design decisions that we chose, was like, Hey, we are not just gonna go into a cave and convert your flutter app or your native apps to flutter and then come back.

We, we decided not to do that. Maybe it would've been easier if we did do that. But you know, like we are also, I think everyone is in a scenario where like no one can just go away for six months and come back to predefined sets of designs or specs [00:23:00] because life's gonna change. And as we are now understanding and knowing like the last two years, Things have absolutely changed for I think most engineers. and even for us, like we started this journey and all of a sudden halfway through it was, Hey, by the way, don't just replace everything using the old APIs that you're doing. Let's make things server driven. Let's start to scale 

right, 

 let's ramp up experimentation.

It's start to scale things a bit more. And that was another little bit of a, beautiful curve ball that life kind of throws you. and. the nice thing is at least we had one platform where we can make those changes, because if we were staying under the old Android and iOS one, it would be, oh, we have more resources than iOS.

Now they can pump it out, and then Android stays behind and then you can't really release at the same time. 

so been a journey. it's really been a fun one. I think, you know, I constantly laugh at my team. Like if we finish and we are still working in sprints. the big thing is like, are we learning?

Are we learning? are we [00:24:00] failing and are we learning? 'cause that's great. and then we can make improvements on it. If it was just like classical music playing in the background and everyone's kind of like zen out and there's no chaos, I would be kind of questioning what we're doing. but, you know, so a little bit of that chaos and order kind of interplay and, we are succeeding.

I, I think is the. The 

long tail answer.

David: You know, you go to the gym and it does, it's not hard. You're not gonna build muscle, 

Pierre: 

David: this, I mean, there's so much in there and I like, that sort of phrase you said, like, the goal is to get value to people, 

Pierre: Yeah. 

David: in what you guys do, where like your value can like really help people. and so if you think about the, whether we can ship this in one month or three months. The number of people that you can really legitimately help two months might mean a very serious difference in terms of the impact you can have on people. And so I think that's what this is all about. I think, um, in engineering or product development, we can all get sort of very focused on, I. The camps we're in, the tools we use, the expertise we have [00:25:00] a lot of identity tied up in this stuff 

Pierre: Yep. 

David: and I think we lose fight sight of the fact that our objective here is to get value to people, like you said, and what are the things or choices we can make to streamline that as much as possible so that we don't spend our time figuring out how to define this in terms of how we did it in iOS or how we did it in Android.

And are we getting parody between those two things that are on different build trains and different release cycles. 

Pierre: Yeah. 

David: behind on that side. Not over here, you know? Yeah.

Part of this is just, and I think this is the natural progression of what engineers are trying to do. There's that whole thing like gimme a lazy engineer any day.

Like, I forget who said it, like some, you know, bill Gates or somebody, 

Pierre: Yeah. '

David: cause the lazy, like, you know, you wanna make it easy. that's sort of the point of engineering. So there's a lot in that. I wanted to ask you a question about that decision. So it sounds like your CTO like made the call 

Pierre: Yeah. 

David: are going to do this. That's a really tough thing to do, right? Because at some point someone has to decide and these types of situations, any transformation, you're never gonna get a hundred percent [00:26:00] agreement. Uh, and

Pierre: Yeah. 

David: in these types of cases. And it sounds like you guys had some people that were like trying to actively find ways to find ways to like, well, maybe we don't want to do this, or maybe there's another method or something like that. how did your company and your team, or your leadership like handle making that decision? And then I'm kind of curious like what happened immediately after that? Because I'm guessing there were some people that were like, Ugh, you know, throw the hand up. Like, how do you get people over the hump and get them on board? 

Pierre: Yeah, I was probably in those conversations myself. like, like if I'm, absolutely honest, right? which is like, hey, I know some of us probably, you know, to your point earlier, I think like we as human splits, you know, I remember back in my Linux days it was like, who uses, what is it cute or GTK or it's V or emax?

you know, it's, we split, we make this, these differences. And, I think the biggest call was. Hey, if as a company we're trying to drive costs down and we're trying to make mental [00:27:00] health accessible, right? And I think especially today where we're like, hey,the banner of like, let's get, let's people, let's get people to love their minds.

we need to kind of. Put that up there with regards to how we kind of value or judge technologies and the tools that we're using. I think the, one of the biggest conversations that I had, I remember with my CTO in this scenario, was again, just reframing that on like, whatever we do, we're using tools to build stuff.

and to your point, like the end goal is for people. And for Headspace, the culture at Headspace oftentimes is we often get readouts for how much the app has helped people. we often also get, uh, readouts for how much people are struggling with what we're building, and, hey, we wish we could kind of make these improvements, et cetera.

and trust me, we have our own long list of things that we want to do to elevate the plan and fighting against the, you know, the. Constant tech debt, which is inevitable whenever you're voting something, you're gonna have [00:28:00] tech debt based on what you're voting. but it wasn't.

I would be honest and say like, Hey, there definitely were people that weren't happy with that decision. you know, these were in, in many cases. These are, you know, I don't want to slight anyone, these were professionals, right? Like they've been doing and working with the technology and honing their skill for 10 plus years.

And as soon as you come and throw in a, Hey, let's learn something new there, there always was the conversation like, Hey, what? I'm really good at this one thing I can operate at speeds that I can't do at this one. What happens with my leveling? What happens with my performance stuff? Like what happens with all of those conversations?

am I still gonna be valued? Am I still gonna be, you know, in, in our economic climate with layoffs and stuff like that are there? What happens to me in that scenario? that definitely was. Conversations that we had to have with people, and honest conversations. And I think big picture, we were like, Hey, we're going on a [00:29:00] journey.

I, I we want everyone to give this six months, try it out for six months, learn the thing, go ahead and learn it. And we try to, as best as what we can, we could carve out capacity for people to, not after hours, but during their working hours. Go and learn dart and flutter. Just go take the time. and that's difficult to do itself, right?

Like some people come to a technology with like, like myself, like I grew up on, you know, turbo Pascal, cc plus. Like, those were my languages that I grew up with. So like jumping into, Dart for me was quick and easy. for other people, they're self taught, or iOS or Android could have been the only language that they were exposed to.

So coming up with any kind of training program or transitional program is going to be hard to do, and hard to kind of see value immediately. you know, unfortunately we did lose some people. We did lose people that said, Hey, there were. They were rock stars at Headspace, and they decided, hey, They wanted [00:30:00] to stick with their career. They wanted to keep on pursuing this thing because they really enjoy it and they wanted to, keep being an expert over there. and that's unfortunate. Like I've lost really good coworkers for that. but I think, you know, this also kind of bumps up with that kind of growth mindset, fixed mindset kind of mentality of, Like languages and tools and stuff like that are going to change what's our North Star. And as a company, I think that's the thing that we kind of have to hold to is, what is the North Star? Is the North Star goal for users or is it technology? and hopefully people aren't at Headspace just because of the technology that they're using.

Hopefully it is on the, I mean, what, the other day we had like. A number is like close to 50 million people that are active users, for the things that we build, that is impactful. 

from my side like that. I still can't kind of 

imagine that number. it's a lot of people that we have an impact on.[00:31:00] 

What can we do ruthlessly to help improve that? It shouldn't be about tool preferences. It should be aggressively, how do we solve those problems? 

David: Yeah, 

Pierre: 

David: fair, like for a person, individual choice in their career, they get 

Pierre: Yeah. 

David: choices and that's part of it. but it's like, are you pushing the vision? Are you pushing the mission and the objective of what you're trying to do? Or are you committed to the tool or the expertise, you know?

And I 

Pierre: Yeah. 

David: We need to always be changing anyway, you know? there it is not, there's all of these things we're talking about today, whether it's our kids growing up and the transformation they're going through, or your transformation of getting these apps to become a hundred percent flutter. These elements, the human side of it, the cultural change, the complexity of managing all the conversations and everything. This to any transformation it's applying right now. Like what are we doing about AI tooling, 

Pierre: Yeah. 

David: it's the 

Pierre: Yeah. 

David: of thing. Like if somebody's a, well, I'm really an expert in Swift. So is chat, GPT and Gemini. You know, like, so it starts to change some of these things, uh, a [00:32:00] little bit. I also, I had a mentor one time that I liked, it was a tough thing to hear, right?

But he was like, okay, look, the thing is, if you're gonna grow, if you're gonna grow fast, especially. Some people who are dear to you are not gonna make it. sometimes it's gonna be because they can't keep up or they, you know, they're not like, sometimes it's gonna be because their mission or their vision becomes misaligned with what you're trying to do. And I thought that was like really helpful guidance and I think it's helpful from a manager perspective is like, just because someone leaves it doesn't mean that it was a bad thing necessarily, right? It doesn't mean that, somebody like that person who left your team who was an amazing good friend, maybe I don't, you know, or an incredible engineer. They're gonna go off and do the thing that's right for them. But 

Pierre: Yep. 

David: as managers, we have to like be very clear, crystal clear about why we're making our choices and be comfortable with the fact that like not everyone's gonna be along for the ride. We can't convince 

Pierre: Yeah. 

David: to be as enthusiastic about the thing that we're trying to do as leaders and especially in these moments of like hard changes where we're 

Pierre: Yeah. 

David: really disrupting what's going on.

So, one quick question about it. So like, we talked a lot about sort of the, [00:33:00] some of the cultural things and some of the difficulties, right? And you said like there was a lot of things you had to work through. Was there anything like through this process that when you started you were like, oh my gosh, this is gonna be so hard. That ended up not being that big of a deal. Like, were there any surprise, both either technology or culturally or process or product-wise? Like, was there something that was surprisingly like not a big deal that you thought was gonna be a big deal? 

Pierre: Whew. That's a really good question. you know, I think as. There were many things that I think that we thought were easier to do, that, you know, came out and completely took us by surprise and completely decimated any timelines that I initially had, which is always great. I would say the thing that I'm really happy about, you know, like Headspace is known as being a very design.

LED company. we are loved by the things that we make and the, the unique branding that we have. I think the thing that really surprised me is how [00:34:00] easily what we built translated into beautiful ui, that works. I think there was always this, whenever you're adopting multi-platform.

technology. I mean, I remember back in the days of Swing and Java, right? where hey, build this thing and it, you have it on the screen and you can kind of tell that this is something weird and different. I think that was , the most surprising thing for me was, hey, build something that is beautiful and we can build something that is fast and beautiful and that works.

that for me was the biggest surprise. And, we could then. Get our design team on board with that. I think that for me was the, I thought I would have to fight a bit more for that, and that was surprising. and that was nice. That was a nice, that was a nice thing on the technical side.

 you know, the door swung a bit, the other way. And I think primarily just how we chose to do our migration, which was way more, it, you know, instead of, again, going into a closet and doing everything from file new, we decided to [00:35:00] approach things from an add to app model. And those are hard, 

especially when you are migrating existing functionality.

I think potentially if you're adding new functionality. You might get things a bit more for free. you know, when you're migrating existing technology, there are often things that you have overlooked or you didn't see, or, you know, some analytic event that you potentially forgot that brings everything down internally.

those are things that are hard. Um,they're hard to see, they're hard to plan for. the complexity is oftentimes hidden. When you're boarding those things out. but for me, I'm, I've been pleasantly surprised by how quickly, two things, right? Like, number one, I remember myself, like I was pleasantly surprised how quickly I could contribute.

I think it was something like, I had like two weeks of just flutter onboarding myself whilst doing day-to-day work. And all of a sudden I was giving a pr, a complex pr, Into our DART stuff. And for me it was like, oh, this is actually like, DART is programming on easy, [00:36:00] to some degree. Um,you know, so that for me was a real like, oh yeah, we are gonna be fine.

 you know, with,what we're building, like what we're boarding is not quite that complex yet. so for me it, there definitely was the view of, okay. Bring the cortisone, bring all of that kind of like unsure, like unsureness down and like, we're gonna be fine. We just need to kind of think about this a bit more.

David: Yeah, I mean I think that's critical to find those frameworks or models that help you like manage this complexity

Pierre: Yeah. '

David: cause you can really quickly fall into chaos if you don't have like strategies for that. so it sounds like you guys found some space to be able to kind of, I. Do this the right way. I mean, definitely that a doc model is very difficult, right?

But this is very, probably the most common way because you, like you said before, you can't stop, you can't stop shipping features. Like you don't really get the luxury. Sometimes you can, I think it depends on how complex your product is or like what your strategy is and some of those types of things.

Pierre: 

you know, I remember one of the reasons for that was when we started this journey, I remember [00:37:00] we, we reached out to a bunch of people and they all kind of mentioned, Hey, a migration takes two years. Like migrating your app takes from start to finish.

Like, Hey, we've done this before. This is gonna take two, three years. and I don't think anyone right on the exec team or anyone is gonna be like, okay, let's go do this for two years. that becomes a really hard sell, I think particularly when the dynamics of marketplace and user demands are gonna change.

so. we were kind of forced into that, that position of like, you have to do things incrementally, step by step. I think at that point, and this probably gives a bit more of like the underlying structure at that point, the way in which we were structured internally was we had our.

Core team, which was a few of us, uh, which I started off in and then started leading, which was like the foundations team, which was creating the bones and the structures for, [00:38:00] you know, how do you launch features on the iOS side and on the Android side, and making it played nicely on the flutter side.

And and then I think initially we had separate squads that would kind of do their domains of migrating things. That becomes hard to do because I'm sure every single squad has their own, or every single group has their own roadmap stuff to do, and no one really accounts for, oh, you gotta migrate this thing and that's gonna take you way more time than what you anticipated.

so we quickly learned, I think it took us a while, but we quickly learned that, hey, that model doesn't quite scale work, or that's going to be the thing that pushes your. Migrating to flutter over X amount of years because there's the larger piece of getting people on the same,how do you say?

Like, getting people up to speed with knowing flutter and being experts over there. and that can be slow depending on what that particular group is busy working on. Maybe they have a way more higher [00:39:00] priority item than converting something to flutter, right? Like they probably have someone like, Hey, this is a giant unlock for.

This group of people, Flutter migration is probably gonna be lower on that, on list of priorities, because it's a one-to-one migration in that 

sense.

so we quickly learned, you know, coming out of this year, in fact in 2025 Jan, we made the switcheroo, which is like, we're not doing that model anymore.

It takes too long. we are gonna kind of have a giant group, that is busy migrating. The app over, and obviously you have it split up in, into groups because you can't have everyone doing the same screen. but that has seemed to work a bit easier. So like that would be definitely be, in, in the vein of how do you centralize knowledge?

How do you get people to communicate with each other? you know, especially in a remote environment that we are in, which is, we have people all, all around the world and all around the country, getting everyone into kind of like a, almost a quasi. war room, oh gosh, I hate that term, but like one, [00:40:00] one, just one room where like, Hey, you're solving this problem and there's a little bit of osmosis that happens by just being there, but you have this constant like, Communication and problem solving, just generative ideas that worked better for us. maybe that works for other people. I don't know. Maybe other groups are smaller that they can kind of do that. But for us, we found that kind of centralized group, and it was a,way larger group.

It was about 27 people that came in. Hey, we're responsible for all the surfaces, while other groups are busy migrating things. or while other groups are busy building their own things. We've definitely seen a improvement in how do you get stuff done in that environment. The hard part is going to be, you know, the group that, that we have that's busy building it, they have to disperse at the end of this kind of quote unquote, migration.

the hope is that they then become the leaders within their respective and within their respective squads that can help mentor, help guide some of the other engineers that might not [00:41:00] be that. expert in Flutter or any of the other technologies. So that's kind of where we're going with it right now.

but so far, so good. 

David: Awesome. I 

Pierre: Yeah. 

David: And so now as you think about where you are, you've been through this experience, you've had a, you know, a career even before this particular project of this 

Pierre: Yeah. 

David: and things that you've learned, curious about,takeaways, like how you've grown and maybe even the company, how it's improved, has going through this experience making That call. Working through it, learning these things like changing the team structure, figuring out how to be successful of this. What is your company or you, what have you learned that helps you to, that you think will be helpful in the future, the next time? whether you're building a product from scratch or you're going through another transformation, what have you distilled out of this process that you think is an indicator or, something managers can do to maximize the performance and the outcomes?

overall, the success of the team. As you go through these complex technology changes.

Pierre: [00:42:00] That is a hard question. That's a really good question. I'm probably gonna butcher the answer because again, I'm still in it, right. I'm not able to have the kind of like the big picture view of this one. So I'm gonna completely kind of answer this from, you know, someone who is. Deep in the migration and battling with, all the fun stuff that happens in that one.

I think what this does do, or this kind of switch does do, at least for us at Headspace and, you know, potentially for any other, company that potentially is wanting to kind of move to photo or looking at like, Hey, what are,what are we trying to solve over here? I think it's that focus and clarity on what is the problem that you're trying to solve, and then looking at the tools that you have at your disposal for how you solve them.

and again, this kind of goes back to, hey, like I think people enjoy being in camps. People have their preferences and you kind of have to acknowledge that. You really have to be focused. I think companies nowadays, specifically companies that need to [00:43:00] potentially, everyone's being a little bit leaner than what they were.

Everyone's being a bit more focused compared to what they were. you have to make trade offs. and you know, I think choosing a technology like flutter. It's not a get out of jail card. Like there, there are pros and cons to every single technology that you use. for us, flutter is at this point a solve for a problem that we had, right?

Like in our problem was, fragmented code bases. Things were not, in parity, keeping resources. At the same, you know, rolling out value to users at the same time was a hard thing for us to solve. Flutter solves that problem for us. Flutter also introduces a whole bunch of other, you know, issues as,we are expanding, we are also realizing that hey, like there are gonna be scenarios, for example, widgets and Apple watches and 

the ecology of devices.

 I enjoy using that term because like the ecology of devices is one of the things of like why I [00:44:00] believe. Why we chose Fluter in the first place was people have multiple devices, they use them interchangeably. let's choose something that can accomplish the goal of getting things out that can cover all of those devices, and you're gonna be, you're gonna have little stragglers on the sides there that aren't going to be covered with that.

so the goal is about ruthless optimization. What can we do? what can we have that is. A source of truth, like, so we know, hey, when there's a bug, we know where to look. You know, that's partially also why we started looking at, you know, we did flutter on that side, which was, Hey, if we have a bug, we know where to look.

It's not just, oh, is it? there, it's one place. And our, evolution with adopting SDUI, it's also trying to solve that problem, which is like, hey, like when someone sees something on the ui, like is it an F statement? And the. In the client code that's doing it. Is it an API thing? It's making these trade-offs about like, how do we identify where the issue is [00:45:00] fast?

Because again, we wanna solve, for us it's a, you know, at Headspace it's a, hey, someone is potentially trying to regulate themselves, trying to help themselves. And for us it's like, oh, oh, we don't have another week to wait. We have to get a fix out to someone because. It could potentially help someone's lives or, save someone's life.

so for us, it's really about like, you know, from the engineering team. And I can promise you, I always get this joke from my friends that, you know, as they know that I'm a Headspace, they always think like, Hey, you guys are just a bunch of hippies that meditate all day. 

I think we probably should meditate more. you know, but it's about how do we, from the engineering team's, perspective. How can we solve problems quickly? and we found that the other route, you know, even in the, when we had the mix of, we have native iOS, we have native Android.

We have flutter. A big push was trying to get out of that place was when there were bugs. It was, it took us [00:46:00] days to kind of figure out where does that bug live? Does it live on a platform service that's just out of communication? is it something on the native side? Is it something on the flutter side?

Is it something that exists in the one app and not on the other app? Like those became so, just hard to solve that. I,we made the right choice. I'm like, okay, let's just like. Solve the problem over here, let's move to one place so that we can make life easier for us. And at Headspace, we are doing that not just on the apps, we're doing that on the infrastructure place where we're like trying to kind of solve those, just unifying a lot of our infrastructure.

I, I would say, and again, the goal is to, so that we can do more with less, I think is the big, the big push.

David: Makes sense. Get that value to, to people faster and you know, and Yeah.

commit to that. I mean, Sam Moore from Betterment, he had a line of like, everybody wants to come to the party. Nobody wants to stay to clean up, you know? And I 

think there's a lot of work, there's a lot of cleanup, there's a lot of things that are not the glamorous part of doing these things that you have to do to get 

to that [00:47:00] sort of final state. To get value to people faster. So this was awesome. Thank you so much for doing this. I guess just to bring us home,and land us here, maybe, you know, do you have any final sort of recommendations like to your past self or maybe even to your future self in a time capsule based on this experience?

maybe give us a little parting thought and then also just if you're hiring or where we can learn more about Headspace. 

Pierre: Yeah, I think. So this is something for me personally that I'm kind of dealing with. It's funny, I actually, I had a therapist appointment before this one. surprisingly enough, embrace failure. that capital F letter, that f letter is the way that we learn. and that's sometimes a hard thing to do in technology when we're, you know, when we are trying to get unit tests out and we have a very binary thinking.

Things are passing, things are failing. Embrace failure. From me on a manager perspective, it was to trust the engineers. to trust them, to trust the decisions that they make, to give them the space to make those decisions and to make the mistakes that they need to [00:48:00] make.

otherwise, um, you know, it's, it's gonna come out anyways, Like make them, embrace. non-pointing fingers, like, don't blame people, but just embrace the fact that like, hey, we're all learning. every technology is imperfect. and so to know that technology is imperfect and we're imperfect, it means that there are, that it's going to be, uh, how do you say it, like failure on the other side.

But then the goal is to like, not just keep it there, not just to avoid it, but to integrate that and to learn. Uh, I think that that for me is a, it's a hard lesson to learn. It's a hard lesson to, to accept. but the goal would be, you know, how do we get better? we don't get better from getting things right all the time.

we don't get things right from making the right decisions. you know, and even in this scenario, as we move to Flutter and embrace all of this change, things are going to not always work out. And that's okay. Uh, because, we can always fix it. [00:49:00] we can always improve. there is always tomorrow in that sense, as, as unfortunate as some, uh, probably as some of my product, uh, managers don't like me saying that there's always tomorrow. 

David: Yeah. Yeah. Tomorrow's expensive. I don't 

Pierre: tomorrow is very expensive.

you know, that's one. There's, there's so much, right? there's so much in the engineering, there's so many final takeaways. I would say like those are the ones that I'm learning in this journey at this point.

David: That's great. Great. So, and if you're hiring or where people, where can people find Headspace and download the app and give it a try? 

Pierre: we are aggressively hiring, photo engineers. There are still many open recs. reach out to me on LinkedIn if you need to reach out to, headspace.com. Uh, really simple, um, careers we have. Multiple openings over there. we are growing, we are aggressively trying to hire, we are, we're trying to make a really big impact.

so, and that will probably continue as we grow and as we, we have more success. 

Yeah. 

David: Awesome. Well, thanks again. Thank you so much. You've learned a lot today and great story, [00:50:00] and,you're very insightful and have a lot of like, great lessons for leadership and management, so 

Pierre: Thank you David. Thank you. Thank you so much. so, so, so happy to be here and just thank you for this opportunity. Thank you.

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