Principal Enterprise Strategist

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.

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).

• Understanding of modern architectural approaches such as microservices, event-driven systems, API-first design, and cloud-native patterns.

• Familiarity with distributed systems concepts such as consistency models, data streaming, synchronous vs asynchronous communication, and resilience patterns.

• Knowledge of reliability, availability, and disaster recovery approaches across multi-AZ, multi-region, and multi-cloud environments.

• Appreciation for security-by-design and performance considerations from the outset of solution design.

• Ability to communicate technical positions effectively to skilled architects and senior engineering leaders.

• Experience guiding teams through Agile, Lean, Continuous Delivery, DevOps, or SRE-aligned delivery models.

Specific technologies we often encounter include Kubernetes, Kafka, Istio, event streaming platforms, and modern cloud services. Experience with these is helpful but not required — what matters is your ability to evaluate, reason, and guide decisions around modern distributed systems.

Professional skills

• Demonstrated experience working with senior business and technology stakeholders, including C-level executives

• Ability to translate complex technical concepts into business value and commercial outcomes

• Strong consultative, advisory, and influencing skills

• Comfort navigating ambiguity, shaping vision, and bringing structure to large-scale transformation

• A collaborative, inclusive, leadership style aligned with Thoughtworks’ values