Engagement Lead

Posted Yesterday
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Singapore, SGP
In-Office
Expert/Leader
Cloud • Information Technology • Software • Analytics
Global tech consultancy blending design, engineering and AI to help businesses thrive through innovation.
The Role
Leads AI-native advisory engagements from strategy through measurable implementation outcomes. Structures complex workstreams, orchestrates teams and AI agents, ensures technical and business quality, manages delivery risks, and advises C-suite technology leaders. The role also drives account expansion and develops reusable engagement models, AI workflows, and decision frameworks.
Summary Generated by Built In

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.

Skills Required

  • Long track record in consulting, product, or technology delivery roles
  • Structured problem-solving ability, including breaking ambiguity into actionable work and evaluating hypotheses, tradeoffs, and outcomes
  • Delivery leadership with accountability for execution, pace, and quality
  • Systems thinking across business processes, technology, data, and end-to-end dependencies
  • Comfort using artificial intelligence to accelerate analysis, generate outputs, and improve delivery efficiency
  • Ability to distinguish when AI outputs can be trusted and when human judgment is required
  • Experience as an Engagement Manager, Project Leader, Product Leader, or Engineering Leader responsible for complex initiatives end-to-end
  • Proven ability to lead multidisciplinary teams in ambiguous environments
  • Effective stakeholder navigation across business and technology stakeholders
  • Clear and concise communication skills

Thoughtworks Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Thoughtworks and has not been reviewed or approved by Thoughtworks.

  • Leave & Time Off Breadth Paid time off includes vacation accrual from day one with rollover, personal/sick days, development and service days, and a long‑tenure paid sabbatical. Policies also emphasize comprehensive leave for rest, illness, and rejuvenation.
  • Healthcare Strength Health coverage spans medical, dental, and vision and often extends to families, complemented by mental‑health support through Lyra and Headspace. In some regions, private providers and wellness rewards further bolster healthcare access.
  • Parental & Family Support Parental leave is positioned as generous across regions, with fully paid options in some markets and a comprehensive fertility policy. Adoption and broader family supports are also highlighted.

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The Company
HQ: Chicago, IL
7,674 Employees
Year Founded: 1993

What We Do

We are a global technology consultancy that delivers extraordinary impact by blending design, engineering and AI expertise. For 30 years, our commitment to design-led thinking, engineering excellence and innovation means we prioritize people, build teams with strong technical foundations and embed AI into every step of the process – not just as a tool but as a mindset. It’s this approach that sets us apart, sparks bold ideas and empowers us to drive real, lasting innovation. We’re not preparing for the future – we’re defining it.

Why Work With Us

As technologists, we have a unique role to play in how technology should benefit all of society, pursuing a more equitable future. Part of that role is to continuously educate ourselves on the issues that matter to the causes we believe in. We recognize our privilege and strive to see the world from the perspective of the most vulnerable.

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