AI-Driven Advisory Delivery Lead

Referrals Only; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job summary

Thoughtworks seeks an Engagement Lead to drive AI-native advisory engagements, combining delivery leadership, product sense, and systems thinking. You’ll own how client goals become actionable workstreams, and oversee the end-to-end delivery from ideas to measurable outcomes.

You will connect CTO/CIO and program leaders with practical execution paths, manage risks, and foster reusable delivery patterns across engagements. This role emphasizes accountability, clarity, and impact.

Qualifications

• Experience in consulting, product, or technology delivery roles.
• Proven ability to lead multi-disciplinary teams in ambiguous environments.
• Structured problem solving to break down ambiguity into actionable work.
• Delivery leadership with accountability and balance of pace and quality.
• Ability to apply AI tools to accelerate analysis and delivery while judging when not to rely on AI.

Responsibilities

• Own Delivery of Outcomes: translate client goals into clear workstreams, milestones and outputs.
• Structure and Lead the Engagement: break down complex problems and define work across team members, AI agents, and client stakeholders.
• Orchestrate AI-Native Delivery: design how AI is used for analysis, scenario modeling, code/workflow generation and documentation.
• Ensure Quality and Coherence: review outputs for logical consistency, business relevance, and technical feasibility.
• Interface with Client Delivery Leadership: act as primary counterpart to CTO/CIO and program leaders to translate advisory recommendations into execution paths.
• Manage Risk and Execution Reality: identify delivery risks early and adjust approaches to maintain progress.
• Build Reusable Delivery Patterns: capture repeatable approaches, workflows and assets.

Skills

Delivery leadership

System thinking

Structured problem solving

AI-native execution

Stakeholder navigation

Job description

Thoughtworks seeks an Engagement Lead to drive AI-native advisory engagements, combining delivery leadership, product sense, and systems thinking. You’ll own how client goals become actionable workstreams, and oversee the end-to-end delivery from ideas to measurable outcomes.

You will connect CTO/CIO and program leaders with practical execution paths, manage risks, and foster reusable delivery patterns across engagements. This role emphasizes accountability, clarity, and impact.