Engagement Lead

ThoughtWorks, Inc.; Singapore; Hybrid; SGD 180,000 - 260,000; Full time

Job summary

ThoughtWorks, Inc. seeks an Engagement Lead to drive AI-native advisory engagements for C-suite level clients. You will translate strategic intent into executable plans, structuring delivery across teams and AI agents to achieve tangible outcomes.

You will manage risk, shape reusable delivery models, and ensure alignment between strategy and execution, guiding client executives through complex tech transformations.

Qualifications

• Proven ability to break down ambiguity into clear, actionable work streams.
• Experience leading complex engagements end-to-end in consulting or tech delivery.
• Strong stakeholder navigation across business and technology domains.

Responsibilities

• Own the delivery of outcomes, translating client goals into workstreams and milestones.
• Lead cross-functional teams and AI agents to ensure quality and relevance of outputs.
• Structure engagements, manage risks, and drive measurable business impact.

Skills

Structured Problem Solving

Delivery Leadership

System Thinking

AI-Native Execution

Job description

The Engagement Lead is the primary delivery, solution, and strategic leader for AI-native advisory engagements. Operating as a trusted advisor to C-suite executives (CTO, CIO, CDO), you lead building high-level technology strategies that define execution clarity and deliver measurable business outcomes. You sit at the absolute center of client engagements - connecting strategic intent with execution reality, structuring and leading strategy delivery, orchestrating human alongside sophisticated AI agents, and mitigating enterprise risks. Beyond engagement delivery, you drive account expansion, shape reusable delivery models, and establish benchmarks for AI-native execution across the consultancy.## Job responsibilities* You own the Delivery of Outcomes (Not Just Plans). You translate client goals into clear workstreams, milestones, and outputs. You ensure delivery leads to measurable business impact, not just recommendations and drive the “last mile” from idea → implementation → outcome.* You structure and lead the Engagement by breaking down complex problems into clear, actionable components, defining how work gets done across: Team members, AI agents & Client stakeholders, and maintain momentum, clarity, and focus across the engagement.* You orchestrate AI-Native Delivery by designing how AI is used across the engagement: Analysis, Scenario modeling, Code and workflow generation, Documentation. You delegate work effectively to AI while maintaining quality and judgment and you ensure outputs are accurate, relevant, and decision-ready.* You ensure Quality and Coherence by reviewing outputs across the engagement for: Logical consistency, Business relevance & Technical feasibility. You connect the dots across workstreams—ensuring a coherent narrative and solution.* You interface with Client Delivery Leadership as the primary counterpart to: CTO / CIO, Program leads & Product and engineering leaders. You translate advisory recommendations into practical execution paths and navigate constraints and tradeoffs in real time.* You manage Risk and Execution Reality by identifying delivery risks early (technical, organizational, or commercial), adjust approach proactively to maintain progress and ensure recommendations are grounded in what can actually be delivered.* You build Reusable Delivery Patterns by capturing and refining of repeatable approaches, workflows, and assets. You contribute to a growing library of: Engagement models, AI workflows and Decision frameworks.* You run your engagements with clarity, pace, and discipline. Your work consistently translates into decisions and outcomes, your clients trust you to bridge strategy and execution. AI is used effectively to increase speed and quality and your approaches become repeatable patterns used by others.## Job qualifications### Technical Skills* You have a long track record of working in consulting, product, or technology delivery roles.* Structured Problem Solving - you can break down ambiguity into clear, actionable work and you think in hypotheses, tradeoffs, and outcomes.* Delivery Leadership - You drive execution with focus and accountability and balances pace with quality.* System Thinking (Not Just Architecture) - you understand how business processes, technology, and data fit together and you can reason about end-to-end flows and dependencies.* AI-Native Execution - you are comfortable using AI to: Accelerate analysis, Generate outputs, Improve delivery efficiency and you know when to trust AI—and when not to.### Professional Skills* You have experience as Engagement Manager / Project Leader, or Product / engineering leader who has led complex initiatives end-to-end.* You have proven ability to lead multi-disciplinary teams in ambiguous environments.* Stakeholder Navigation - you work effectively across business and technology stakeholders and you communicate clearly and concisely.## Other things to know### Learning & DevelopmentThere 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.## Responsible Use of AI in RecruitmentAt Thoughtworks, we use AI tools to support our recruitment team with administrative tasks such as drafting communications, scheduling interviews and writing job descriptions. Crucially, our AI tools do not screen, assess, rank or make hiring decisions. Every application is reviewed by our team and all selection decisions are made exclusively by our interviewers and hiring managers. We are committed to fairness and responsible AI. We actively manage our AI systems by testing, monitoring for biased outcomes and implementing mitigation measures. We hold our third-party vendors to these same high standards through a rigorous governance process. For additional information, please see our full Thoughtworks AI Policy for Recruitment.## Job DetailsCountry: Singapore Location: Singapore Location type: Hybrid Date Posted: 10-16-2026 Industry: Information Technology Employment Type: Employee