Lead/Principal Modernisation Strategist

About the role

Thoughtworks Singapore is seeking an experienced technologist to guide clients through complex platform and portfolio transformations. You will bridge the gap between business strategy and engineering execution, designing high-level roadmaps that deliver measurable commercial results. This role focuses on architectural leadership, stakeholder advisory, and shaping large-scale modernisation programs.

Key facts

What you'll do

• Define target architectures for large-scale software modernisation while managing complex technical trade-offs.
• Partner with C-suite and technology leaders to align transformation initiatives with business objectives.
• Lead pre-sales activities, including proposal creation, engagement shaping, and identifying new opportunities.
• Provide architectural direction and decision frameworks to delivery teams.
• Mentor consultants and contribute to internal thought leadership, patterns, and accelerators.
• Advise executives on navigating legacy landscapes and implementing modern engineering practices.

Requirements

• Proven experience leading large-scale application migration or modernisation programs in complex sectors such as banking, insurance, telco, government, energy, or logistics.
• Strong architectural background with expertise in distributed systems, legacy system integration, and modern engineering.
• Proficiency in designing distributed architectures, including event-driven systems, microservices, and API-first designs.
• Deep understanding of cloud-native patterns, reliability, availability, and disaster recovery across multi-cloud or multi-region environments.
• Experience guiding teams through Lean, Agile, SRE, DevOps, or Continuous Delivery models.
• Ability to communicate complex technical strategies to senior stakeholders and C-level executives.

Nice to have

• Familiarity with Kubernetes, Kafka, Istio, and event streaming platforms.

Skills & tools

• Distributed systems (consistency models, data streaming, resilience patterns).
• Security-by-design and performance engineering.
• Consultative and advisory leadership.
• Strategic planning and stakeholder management.

Practical notes

• This is not a primary hands-on coding role.
• Expectation of working from the Thoughtworks office or the client site for all five working days, depending on project needs.
• Applications are kept confidential.