Lead/Principal Modernisation Strategist

Visa Hunt; Singapore; Hybrid; SGD 180,000 - 300,000; Full time

Job summary

Thoughtworks Singapore is seeking a seasoned technologist to partner with client organisations and guide multi‑year platform modernisation efforts. You will translate technical strategy into measurable business value while engaging with C-suite and senior leaders.

The role combines design, selling, and leading the implementation of transformation programs grounded in engineering excellence. You’ll contribute to thought leadership, mentor teams, and shape modernisation practices that scale across

Qualifications

• Seasoned technologist with the ability to translate technical strategy into business value.
• Experience guiding large-scale transformation and modernisation programs.
• Ability to communicate with C-level executives and senior engineering leaders.
• Familiarity with modern architectural patterns and cloud-native approaches.

Responsibilities

• Define the target architecture for large-scale software modernisation, aligning with business objectives.
• Partner with business and technology leaders to identify opportunities and shape transformation approaches.
• Lead pre-sales activities, proposals, and engagements to educate clients and colleagues on value delivered.
• Act as a trusted advisor to executives, navigating legacy landscapes and framing technical trade-offs.
• Contribute thought leadership and patterns that scale across regions.
• Provide architectural direction to delivery teams and mentor consultants.

Skills

Architectural leadership

C-suite engagement

Modernisation strategy

Distributed systems

Agile delivery

Tools

Kubernetes

Kafka

Istio

Job description

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).
  • 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

Other things to know

Learning & Development

There is no one-size-fits-all career path at Thoughtworks: however you want to develop your career is entirely up to you. But we also balance autonomy with the strength of our cultivation culture. This means your career is supported by interactive tools, numerous development programs and teammates who want to help you grow. We see value in helping each other be our best and that extends to empowering our employees in their career journeys.

Onsite Work Expectation

You may be expected to work out of our Thoughtworks office or at our client's office location for all five working days of the week, depending on business or clients' needs.

About Thoughtworks

Thoughtworks is a global technology consultancy that integrates strategy, design and engineering to drive digital innovation. For 30+ years, our clients have trusted our autonomous teams to build solutions that look past the obvious. Here, computer science grads come together with seasoned technologists, self-taught developers, midlife career changers and more to learn from and challenge each other. Career journeys flourish with the strength of our cultivation culture, which has won numerous awards around the world.
Join Thoughtworks and thrive. Together, our extra curiosity, innovation, passion and dedication overcomes ordinary.

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