Chief Architect - Tradenet

What you'll do 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 experience in Java/JVM ecosystems, PostgreSQL, and cloud-native tooling is the important part. • Experience with AI/LLM-assisted engineering beyond basic code completion — reverse-engineering pipelines, agentic workflows, or AI-augmented analysis at the architectural level. • Strong written technical communication. Your architecture documents and RFCs need to stand on their own and be implementable by teams without further explanation. Good to have • Experience in Singapore government technology ecosystem (GovTech, SGTS, IM8/CSA frameworks). • Background in trade, customs, regulatory, or financial platform engineering. • Prior engineering management experience (team lead, EM) — useful for mentoring and influence, though this is an IC role. • Experience with data-governance and compliance constraints that shape architecture (data residency, classification, audit trails). • Familiarity with the Java/J2EE legacy ecosystem you'd be migrating away from.