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When you think of a technical migration, you might picture lines of code, build systems, or platform APIs. But for Pierre Benz, Engineering Manager at Headspace, the real work of merging two mental health apps into one went far beyond the code. It was about people, purpose, and building the kind of technology that can truly support someone’s well-being, especially when they need it most.
In the latest episode of Build to Succeed, Pierre walks us through how his team navigated one of the most ambitious transformations in Headspace’s history. Along the way, he opens up about leadership, lessons learned from failure, parenting, and why sometimes the hardest part of change is letting go of what used to work.
A Career Built on Empathy and Experimentation
Before leading engineering at Headspace, Pierre’s career had taken him through design agencies like AKQA, startups in IoT and consumer apps, and even early explorations in game development. His technical roots are deep, but what stands out most is his focus on human behavior.
That focus began at the University of Cape Town, where Pierre blended his computer science studies with human-computer interaction and psychology. It’s a thread that has continued throughout his career, shaping how he approaches product development, team leadership, and user experience.
Surrounded by technically brilliant peers early in his career, Pierre chose to focus on a different strength: understanding the why behind technology use, not just how to build it.
The Merger That Changed Everything
Pierre joined Headspace just as the company merged with Ginger, a behavioral health platform offering coaching and therapy. The result? Two different apps, two different codebases, and one big challenge: how to bring everything together in a single product experience without losing momentum or user trust.
At first, they approached the problem the only way they could: by patching it. A shared Flutter SDK was built and embedded into the existing native apps, a move Pierre jokingly refers to as their “Frankenstein moment.” It worked, but it wasn’t scalable. Maintaining multiple stacks slowed development, and the team knew something had to change.
Making the Case for Flutter
That’s when the real decision-making began. After a round of internal research and heated debate, the team faced a turning point: go all-in on Flutter, or continue to juggle three partial implementations across iOS, Android, and web.
The final decision came from Headspace’s CTO, who saw the bigger picture: a single codebase would allow the company to scale faster, reduce costs, and deliver a more unified experience across platforms. It wasn’t just a tech decision, it was a mission decision. “Life’s gonna change. Let’s ramp up experimentation. Let’s scale things more. And we now have one platform where we can address those changes,” he recalls.
For Pierre and many native developers, it was a tough pill to swallow. Not everyone was on board. Some engineers left. Others took time to upskill in Dart and Flutter. But for those who stayed, it sparked a mindset shift—from resistance to curiosity to momentum.
“The ecology of devices is why we chose Flutter. People use multiple devices interchangeably. We can get an app out that can cover all those devices,” Pierre reflects.
Building While Migrating (and Not Burning Out)
One of the hardest parts of the migration was that they didn’t pause feature development: instead of stopping everything to rebuild, the team adopted an incremental approach, slowly replacing key surfaces with Flutter while continuing to ship updates. It wasn’t the cleanest method, but it was realistic, and it allowed the team to learn in motion.
Pierre speaks candidly about the complexity of this strategy, from keeping analytics intact to migrating UI components without breaking existing features. But he also highlights the unexpected wins, like how quickly new developers got up to speed and how Flutter exceeded design expectations.
Centralizing the Mission: One Team at a Time
Eventually, the team learned that spreading migration responsibilities across too many squads wasn’t working. So they pulled together a dedicated migration team: 27 engineers focused solely on rebuilding the app’s foundation. That centralized effort not only accelerated progress but also helped create a shared sense of ownership and clarity.
Once the migration is complete, those engineers will return to their respective teams as Flutter champions, mentoring others and helping maintain quality across the newly unified codebase.
Doing the Hard Things Right
At VGV, we believe technology should be built for people, and this story from Headspace proves exactly why that matters. It’s a rare and honest look at what it means to transform systems, cultures, and teams without losing sight of the human impact.
This is a blueprint for doing the hard things well: with empathy, clarity, and a willingness to rethink everything for the sake of delivering real value.
We would love to hear your story and help you start your Flutter journey. Get in touch with our team today!
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