Chapter 04
The Systems
2021–2024
Enterprise systems for airports and universities, EdTech across four countries, and the first AI-powered features — learning to hold complexity without simplifying it away.
After the coup
The military coup in February 2021 changed everything in Myanmar. Foreign investment froze. The economy stalled. Inflation climbed. For an e-commerce platform that depended on consumer confidence and a functioning logistics network, the environment became impossible.
I moved to Thailand and joined WeesWares remotely — a Singapore-based development studio that served enterprise clients. It was a sharp shift. At rgo47, I'd built a team and a product from scratch in an emerging market. Now I was managing projects for Changi Airport Group, Singapore Red Cross, and Singapore Management University.
The pace hit me first. Enterprise clients in Singapore operated with a precision and urgency that was completely different from what I'd known. Multiple projects ran in parallel, each with its own stakeholders and deadlines. I learned stakeholder management not from a textbook but from the pressure of keeping three institutional clients informed and confident at the same time.
A team across six countries
The WeesWares team was fully remote, spread across India, Myanmar, Thailand, Singapore, Hong Kong, and the Philippines. Remote-first was the norm, not a pandemic adjustment.
Then one morning, several of my team members in Myanmar went dark. No messages, no online status, nothing. An internet and electricity blackout had hit their region — one of those unplanned risks that no sprint planning accounts for.
We lost contact for a full day. I didn't know if they were safe.
Within hours, I'd recruited two freelancers on a scope basis to keep the project moving, briefed the client on the incident, explained the potential delay, and walked them through our mitigation plan. Transparency wasn't a strategy — it was the only option.
The team members came back online after a few days. We helped relocate them somewhere safer. The project was delayed by a week, but the client accepted it because we'd kept them informed throughout. That incident taught me more about stakeholder management than any certification ever could — that trust is built in the moments when things go wrong, not when they go right.
Back to products
WeesWares taught me enterprise discipline, but I missed building products that reached people directly. CommonTown — an A*STAR Singapore spin-off specialising in education technology — was exactly that fit. Their products helped students learn. That was a thread I could trace all the way back to Extraordinary Jenny Jones and Phew Myanmar Alphabets.
The flagship product I managed was CommonAcademy, a learning management system built in collaboration with master educators. It wasn't a simple course-hosting platform. The Learning Flow Engine let course designers define conditional branching rules through a visual interface — learners received different content paths based on quiz performance. Deliberate Practice used Item Response Theory algorithms for adaptive quizzing and spaced repetition.
The platform was deployed to schools across Southeast Asia and Hong Kong — four countries with different curricula, languages, and educational expectations.
I also managed Qoqolo, a Student Management System running across Star Learners Preschools' forty-five branches in Singapore. Different product, different audience, same discipline: understanding how an institution actually works before designing software around it.
The writing tools
We added AI-powered features to CommonAcademy: Writing Coach and Writing Feedback. This was before ChatGPT made AI writing tools a household concept. Both tools were built on the Cambridge Rubric — students received instant structured feedback on their writing, guided coaching for story crafting, and teachers could review the final output rather than marking every draft round by hand.
Teachers responded well. The tools saved hours of manual review without replacing their judgment, and students got feedback in real time instead of waiting days.
But the moment I remember most clearly came during a trial with a school in Phnom Penh, Cambodia. The teacher called me on a live video to show her classroom. Students were using the writing tools, and they were genuinely enjoying it — not just completing an assignment, but engaged in the process of crafting stories with real-time coaching.
That was the moment that makes product work worth it. Not the analytics dashboard, not the deployment metrics. A teacher holding up a phone to show you that something you shipped made a room full of students want to write.
What I carried forward
This chapter covered two companies and two roles, but the lesson was one: complexity is the work, not an obstacle to the work. At WeesWares, the complexity was institutional — airports, universities, humanitarian organisations, each with processes that existed for reasons nobody could fully articulate. At CommonTown, the complexity was pedagogical — adaptive learning across languages, cultures, and age groups.
I earned my PMP and PSM certifications during this period, formalising the project management practice I'd been building since Chapter 02. But the real education was the Myanmar blackout, the enterprise deadlines, and the Phnom Penh video call. Credentials tell employers what you know. Those moments taught me what kind of PM I wanted to be.