Chief Architect - TradeNet

GovTech is the lead agency driving Singapore’s Smart Nation initiatives and public sector digital transformation. As the Centre of Excellence for Infocomm Technology and Smart Systems (ICT & SS), GovTech develops the Singapore Government’s capabilities in Data Science & Artificial Intelligence, Application Development, Smart City Technology, Digital Infrastructure, and Cybersecurity. At GovTech, we offer you a purposeful career to make lives better where we empower our people to master their craft through robust learning and development opportunities all year round. Play a part in Singapore’s vision to build a Smart Nation and embark on your meaningful journey to build tech for public good. Join us to advance our mission and shape your future with us today! Learn more about GovTech at tech.gov.sg. How we build TradeNet is Singapore's National Single Window for trade permit processing. It handles over 9 million permit applications annually and accounts for around 10% of national tax revenues. We are replacing the decades-old legacy system with a modern, cloud-native platform. The rebuild touches everything: decomposing a monolithic Java/J2EE application into cloud-native services, reconstructing undocumented business logic from incomplete legacy code, clearing compliance and data-governance constraints, and delivering a platform that multiple government agencies depend on daily. The Chief Architect owns the technical coherence of this effort. You define how the system is structured, how teams interface with each other, and where the hard boundaries are. You work across product squads, TechOps, and programme leadership — but your authority is technical, not managerial. Teams here use AI-assisted development workflows daily, including LLM/agentic-AI tooling for spec building, code generation, and test automation. You are expected to push the boundaries of what's possible with these tools. [What you will be working on] Architecture & technical direction • Set the overall system architecture for the TradeNet platform — service decomposition, data architecture, API contracts, infrastructure patterns. • Make binding technical decisions across teams. Resolve cross-squad technical disputes. Own the architecture decision record. • Design for resilience: fault isolation, blast-radius containment, defensive API contracts, and graceful degradation across a system that cannot go down. • Define the architectural guardrails, contracts, and patterns that teams build on — enabling independent delivery without architectural drift. Legacy modernisation • Lead the technical strategy for decomposing and replacing the legacy monolith, including where to strangle, where to rewrite, and where to leave alone. • Reconstruct undocumented business logic from incomplete legacy codebases — using source analysis, documentation archaeology, dependency tracing, and AI-assisted reverse-engineering. • Navigate compliance and data-governance constraints that shape what can be migrated, how, and when. Hands-on technical work • Write architecture documents, design specs, and technical RFCs that teams implement against. • Review code and designs across squads — particularly at integration boundaries and in foundational components. • Prototype and prove out critical technical approaches before committing teams to them. • Lead root-cause analysis on hard production and programme-level technical problems. AI-assisted engineering • Pioneer and refine AI/LLM-assisted approaches to legacy analysis, code generation, test creation, and documentation. • Set the technical standards for how AI-generated output is evaluated, attributed, and held to quality. • Push the programme's use of agentic AI beyond basic code completion into architectural and analytical workflows. Technical leadership • Earn trust with engineering teams through technical credibility — you lead by being right and being helpful, not by title. Your authority comes from the quality of your decisions and your willingness to get into the details. • Resolve technical disputes across squads. People will disagree on approach, and you are the one who makes the call and gets buy-in from both sides. • Balance technical debt against migration timelines. Know when to take a shortcut to hit a delivery date and when to say no because the long-term cost is too high. Make these tradeoffs explicitly and visibly. • Grow technical leads across squads. Mentor senior engineers. Raise the bar on technical decision-making across the programme. • Provide technical input to programme-level decisions: sequencing, risk, feasibility, and pivot recommendations. • Secure executive alignment on technical direction, particularly under ambiguity or when course corrections are needed. [What we are looking for] • At least 12 years of hands-on software engineering, with significant time spent as a principal/staff engineer or architect on large-scale systems (not purely management track). • Experience as the overall technical lead across multiple teams (5+ teams, 40+ engineers) — setting architecture that others build on, without directly managing them. • Deep experience with legacy modernisation: decomposing monoliths, migrating off on-prem platforms, reconstructing business logic from incomplete or undocumented systems. You've done this before and know where it goes wrong. • Strong cloud-native architecture background — service design, event-driven systems, API-first platforms, infrastructure-as-code. Ideally on AWS. • Demonstrated ability to make hard technical calls under ambiguity — pivoting programmes, resolving cross-team disputes, and getting executive buy-in for technical direction when the path isn't clear. • Experience designing defensive/resilient architectures for systems that cannot afford downtime — fault isolation, contract enforcement, blast-radius containment. • Hands-on proficiency in a modern backend stack. The programme uses Kotlin, but deep experie…