Legacy architecture and outdated team structures impede agility
If your team’s velocity is slowing down and basic tasks are dragging out, it’s not a resource issue, it’s probably a structural one. At Wattpad, after more than a decade of iterating on product and infrastructure, things that should’ve been quick wins started taking too long. It wasn’t subtle either. Engineers were spending more time figuring out where to make changes than making the changes themselves.
Legacy architectures do one thing very well: they hang around. So if your company started building more than 12 months ago, and let’s be honest, most have, your technology likely has more layers than it needs. Pair that with a team structure that hasn’t evolved with the technology, and you get misalignment. That’s when agility dies. Your product team stops shipping quickly. Experiments stall. Users either notice the lag or your competitors take the lead.
This isn’t a weird problem. It’s growth. But growth done well means looking hard at whether your current system still enables speed. Most teams avoid the reset. It feels risky. But if you want your people to focus on innovation instead of maintenance, you’ll need to evolve the structure that got you here. And soon.
Legacy doesn’t just mean old code; it means institutional inertia. For executives, that’s a signal to go beyond incremental updates. This is strategy, not cleanup. Putting off architectural shifts because it’s politically or operationally inconvenient? That’s short-term thinking. You need to engineer for now and next, even if it means tearing up a few sacred workflows.
Increased complexity and siloed full-stack teams elevate cognitive load
Wattpad took an approach many companies favor, full-stack, product-aligned teams. On paper, it works. Teams own the end-to-end experience and can move fast. In practice, things changed. The platform grew, which sounds good. But the complexity grew with it.
Suddenly, each team needed to understand too much: systems they didn’t build, legacy workflows they didn’t design, and surface areas that grew exponentially. That’s not effective autonomy, it’s overload. When everyone owns everything, nobody owns anything. The result? Conflict. People pull the system in different directions based on local priorities, creating friction. Not because they’re wrong, but because they can’t see the full picture anymore.
This also raised the cognitive load. Engineers spent time just understanding what to change before they even began coding. And when coordination fails, even well-intentioned designs start to diverge. One team makes a smart decision that breaks someone else’s pipeline. Not because anyone screwed up, but because no one knew how deep the rabbit hole went.
From a leadership perspective, this isn’t a tooling issue. It’s structural. Cross-functional teams don’t scale linearly with product or technical complexity. If you don’t add boundaries and clarity along with growth, you end up with overlapping, inefficient roles. That leads to burnout, bugs, and blockers. Instead, design for predictable ownership and reduce unnecessary system exposure. Scale your organization like you scale your platform, intentionally.
Insufficient time dedicated to technical investment deepens existing challenges
Most companies don’t fall behind because they lack ideas or talent. They fall behind because they don’t prioritize system health. At Wattpad, the demands of new product initiatives consumed nearly all available time and focus. The consequence? No space was left for infrastructure upgrades or technical debt reduction. Every feature launch started to feel heavier, slower, and more uncertain.
This wasn’t a failure of engineering. It was a failure of balance. When teams are bogged down by the weight of fragile systems and outdated patterns, they move cautiously, even when speed is needed. Product teams will always prioritize what delivers value fast. That’s fine. But when leaders don’t make room for foundational improvements, the system slowly grinds itself down.
The longer technical investment is deferred, the more expensive it becomes. Engineers eventually spend their time sustaining the unsustainable, diving headfirst into legacy environments they’ve never touched, rebuilding the same abstractions repeatedly, and losing momentum. Meanwhile, the opportunity cost compounds.
For executives, the takeaway is straightforward. Your roadmap must reserve space to modernize at the same cadence you innovate. If technical work is always deferred in favor of features, what you’re really doing is increasing friction and future cost. Every executive who oversees product or engineering should be able to answer this: how much of your team’s time is protected for long-term system health? If the answer is “not enough,” you’re actively working against your own growth trajectory.
Misalignment between organizational structure and systems architecture requires intentional redesign
There’s a principle you should care about, Conway’s Law. It’s been referenced by engineering teams for years because it holds up. Simply put, the way you structure teams affects the way your systems behave. Wattpad realized their teams had evolved in ways that no longer matched the architecture they were building on. That misalignment started to erode technical clarity, system coherence, and team output.
When the structure of your organization diverges from how work actually gets done, friction increases. Teams don’t just slow down, they multiply complexity. At Wattpad, overlapping ownership meant redundant paths of system evolution. No central thread held it together. Smart engineers were making smart choices, but without organizational grounding, they couldn’t scale those choices across products or platforms.
To fix that, Wattpad didn’t just change tech. They rewired their organizational model alongside it. They defined clear systems boundaries and aligned teams to each of them. Leadership worked closely with engineers to ground the transformation in how the platform actually functions today, and how it needs to evolve in the next stage.
Most transformations fail not because the strategy is wrong, but because communications and incentive structures don’t match technical goals. For C-suite leaders, it’s essential to realize architecture is not a background decision, it’s directly shaped by how your teams are staffed, structured, and encouraged to collaborate. If you want scalable systems, start with scalable structures. Then redesign both.
Iterative redesign driven by engineer-led insights promotes scalable change
Wattpad didn’t treat its architecture overhaul as a top-down mandate. Instead, they pulled in the people closest to the systems, the engineers who live with the problems daily. Senior technical leaders and frontline engineers conducted deep system reviews and continuous diagnostics. That insight formed the basis for both architectural and organizational changes. Real-world input made everything more grounded, more flexible, and more likely to succeed.
Engineers were given choice and ownership. They opted into specific areas of the platform based on where they could contribute most. Leadership provided support and vision, but execution was distributed. This wasn’t about dictating what to fix, it was about removing blockers so engineers could make meaningful progress on what they already knew needed attention.
What came out of that approach wasn’t a perfect end state, it was momentum. Systems started moving in the right direction. Engineers were no longer reacting to outages or patching around legacy issues; they were designing forward, with strong architectural boundaries that let them work more independently and effectively.
For executives, the key here is empowerment backed by context. Engineers know where the pain points are far earlier than leadership does. Your job isn’t to prescribe the fix. It’s to ensure they have the time, autonomy, and information to solve real system-level problems. Strategy doesn’t succeed until it reaches the hands designing and deploying the work. The organizations that outperform are the ones where decision-making scales as intelligently as the infrastructure.
Ongoing organizational transformation requires flexibility
Wattpad’s transformation didn’t happen in isolation. This was a coordinated shift across systems, teams, and leadership perspectives. Changes to architecture were mirrored by changes in team structure, priorities, and how decisions were made. Some systems were rebuilt. Others phased out. The organization adapted, one step at a time, without compromising on core deliverables. That kind of dual-track progress requires clarity, discipline, and buy-in from across functions.
A key success factor was trust. Engineering leadership didn’t push change top-down. Instead, they invited collaboration. Engineers shaped solutions. Managers unblocked paths. Leaders stayed aligned on the long-term vision while accepting that today’s structure was transitional. This mix of confidence and agility ensured that even when every system wasn’t perfect, the teams had clear direction and momentum. Importantly, no one lost sight of the actual goal: enabling faster product development by restoring technical clarity.
They’re still evolving. The architecture and structure aren’t frozen. They’re designed to adapt. What matters is that the organization has a process now for change, one that doesn’t rely on emergency fixes or long backlogs. This is how you make capability the norm, not the exception.
For C-suite leaders, this is more than an engineering concern. Organizational resilience starts with aligned decision-making and a shared roadmap across functions. Transformation doesn’t wait for a final plan; it begins with structure that invites feedback, absorbs lessons, and maintains forward motion. If your teams don’t feel trusted, and if leadership isn’t willing to shift with reality, you’re not transforming, you’re stalling.
Key takeaways for decision-makers
- Prioritize architecture audits as systems mature: Legacy architecture and early-stage team structures degrade over time, slowing execution and reducing product agility. Leaders should reassess technical foundations early to maintain velocity at scale.
- Reduce system exposure to lower team cognitive load: Overextended full-stack teams face complexity that fragments ownership and slows delivery. Executives should simplify technology access by clearly bounding responsibility and system domains.
- Allocate protected time for technical investment: When infrastructure fixes are perpetually deprioritized, technical debt compounds and innovation stalls. Leaders must create space in roadmaps for long-term system health, not just product features.
- Align teams with how systems actually function: Disconnected communication structures and system architecture create inefficiencies. Redesign organizations around system boundaries to ensure collaboration, ownership, and platform scalability.
- Elevate engineers as partners in transformation: Top-down change limits effectiveness. Empowering engineers to lead systems redesign drives grounded, scalable improvements rooted in real-world usage and team-level insight.
- Treat transformation as an ongoing operating model: Lasting change requires flexibility, cross-functional trust, and constant iteration. Leadership should align vision with evolving team structures to maintain agility and momentum.
