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Thoughtworks

Engagement Lead

Thoughtworks is hiring an Engagement Lead in Singapore, Singapore. Level rates it ; you can apply on Thoughtworks.

Level's read on this job

  • On Level's scale, this role is Little AI ●○○○: aI is not part of the work.
  • The posting mentions AI agents and AI safety among its tools and skills.
  • Level classes it as a lead role.
  • Thoughtworks has 44 other open roles on Level.

AI in this role

ai-agentsai-safety

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 & 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.

Responsible Use of AI in Recruitment

At 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.

About Thoughtworks

Thoughtworks is a dynamic and inclusive community of bright and supportive colleagues who are revolutionizing tech. As a leading technology consultancy, we’re pushing boundaries through our purposeful and impactful work. For 30+ years, we’ve delivered extraordinary impact together with our clients by helping them solve complex business problems with technology as the differentiator. Bring your brilliant expertise and commitment for continuous learning to Thoughtworks. Together, let’s be extraordinary.

#LI-Onsite

See here our AI policy.

How we rate this

Engagement Lead at Thoughtworks rates 16 out of 100 for how much of the daily work is AI. That makes it Little AI (AI Level 1 of 4). The level is about AI in the job, not seniority.

Classification

Little AI. AI is not part of the work.

  1. ●●●● Builds AI80 to 100
  2. ●●●○ Works on AI60 to 79
  3. ●●○○ Uses AI40 to 59
  4. ●○○○ Little AI0 to 39

Levels come from how often the tools, models and workflows of the role are named in the posting itself. Read the description and count the AI tools, models and workflows it names.

Prepare for this job

Built from this posting and from similar jobs on Level.

Skills and AI tools this role asks for

AI agentsAI Safety

Questions you could be asked

  1. How do you decide when an AI agent can act on its own versus asking for approval first?
  2. How do you think about the risk of an AI system in this kind of role failing silently?

Adapt your resume

  • List these exact terms on your resume: AI agents and AI Safety. An applicant tracking system matches the wording, not the idea.
  • Attach one line of real, concrete experience to at least one of them. A tool named with nothing behind it rarely survives a human read.

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