Lead/Principal Modernisation Strategist

Are you a seasoned technologist who thrives at the intersection of business strategy, architecture, and modern engineering practices?  Thoughtworks Singapore is looking for a seasoned technologist to partner with and guide our client organisations through complex platform and portfolio modernisation, translating technical strategy into measurable business value. In this high-impact role, you will be accountable for designing, selling, and leading the implementation of large-scale transformation and modernisation strategies, from initial vision through to successful execution. While this is not a primary hands-on coding role, you must possess the depth of technical credibility required to engage deeply with client C-suite and technical leadership, challenge assumptions, ask the right questions, and shape an ambitious modernisation strategy grounded in engineering excellence. You don’t need to tick every box. If you’re a strong seasoned technologist with a passion for driving change, we’d love to hear from you. Job responsibilities You will define the optimal target architecture for large-scale software application modernisation, explicitly leading the analysis of complex trade-offs to align the design with non-functional requirements and business objectives. You will partner with business and technology leaders to identify modernisation opportunities, shape transformation approaches, and align technology decisions with business goals. You will be involved with pre-sales, lead generation, creating proposals, shaping engagements for clients and helping to educate both clients and colleagues about the value of our services and the commercial success they can deliver. You will act as a trusted advisor to C-level executives, helping them navigate complex legacy landscapes, make informed technical trade-offs, and redefine what’s possible in their industry. You will contribute thought leadership through points of view, reusable patterns, accelerators, and modernisation practices that scale across regions. You will support delivery teams by providing architectural direction, context, and decision frameworks that help them execute modernisation programs effectively. You will mentor and develop consultants and technologists, nurturing the next generation of modernisation leaders at Thoughtworks. You will stay current with emerging technologies and Thoughtworks’ global strategy, contributing insights that help us evolve our approach to modernisation. Job qualifications Technical Skills A strong architectural foundation with the ability to reason about legacy systems, distributed architectures, and modern engineering practices. Experience driving large-scale application modernisation or migration programs in complex organisations (e.g., banking, insurance, telco, government, energy, logistics, or similarly scaled domains). You have experience designing and leading modern, distributed architectures (e.g., containers, service mesh, event streaming). Und...