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Technology Advisory Engagement Lead

Job in Toronto, Ontario, C6A, Canada
Listing for: Thoughtworks
Full Time position
Listed on 2026-08-21
Job specializations:
  • Business
    AI Business & Operations, Business Systems & Technology Analysis
  • IT/Tech
    AI Business & Operations, Business Systems & Technology Analysis
Salary/Wage Range or Industry Benchmark: 159000 - 309000 CAD Yearly CAD 159000.00 309000.00 YEAR
Job Description & How to Apply Below

The Engagement Lead is the delivery and solution leader for AI-native advisory engagements. This role combines the responsibilities of an engagement manager, product leader, and systems thinker—owning how strategy translates into working solutions and measurable outcomes. You sit at the center of the engagement—connecting client intent, business outcomes, and execution reality.

Job responsibilities
  • Own Delivery of Outcomes
    • Translate client goals into clear work streams, milestones, and outputs.
    • Ensure delivery leads to measurable business impact, not just recommendations.
    • Drive the “last mile” from idea → implementation → outcome.
  • Structure and Lead the Engagement
    • Break down complex problems into clear, actionable components.
    • Define how work gets done across:
      • Team members
      • AI agents
      • Client stakeholders
    • Maintain momentum, clarity, and focus across the engagement.
  • Orchestrate AI-Native Delivery
    • Design how AI is used across the engagement:
      • Analysis
      • Scenario modeling
      • Code and workflow generation
      • Documentation
    • Delegate work effectively to AI while maintaining quality and judgment.
    • Ensure outputs are accurate, relevant, and decision-ready.
  • Ensure Quality and Coherence
    • Review outputs across the engagement for:
      • Logical consistency
      • Business relevance
      • Technical feasibility
    • Connect the dots across work streams—ensuring a coherent narrative and solution.
  • Interface with Client Delivery Leadership
    • Act as primary counterpart to:
      • CTO / CIO
      • Program leads
      • Product and engineering leaders
    • Translate advisory recommendations into practical execution paths.
    • Navigate constraints and tradeoffs in real time.
  • Manage Risk and Execution Reality
    • Identify delivery risks early (technical, organizational, or commercial).
    • Adjust approach proactively to maintain progress.
    • Ensure recommendations are grounded in what can actually be delivered.
  • Build Reusable Delivery Patterns
    • Capture and refine repeatable approaches, workflows, and assets.
    • Contribute to a growing library of:
      • Engagement models
      • AI workflows
      • Decision frameworks
Job qualifications

Technical Skills
  • Experience in consulting, product, or technology delivery roles.
  • Proven ability to lead multi-disciplinary teams in ambiguous environments.
Professional Skills
  • Structured Problem Solving:
    • Can break down ambiguity into clear, actionable work.
    • Thinks in hypotheses, tradeoffs, and outcomes.
  • Delivery Leadership:
    • Drives execution with focus and accountability.
    • Balances pace with quality.
  • System Thinking (Not Just Architecture):
    • Understands how business processes, technology, and data fit together.
    • Can reason about end-to-end flows and dependencies.
  • AI-Native Execution:
    • Comfortable using AI to: accelerate analysis, generate outputs, improve delivery efficiency.
    • Knows when to trust AI—and when not to.
  • Stakeholder Navigation:
    • Works effectively across business and technology stakeholders.
    • Communicates 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.

Accommodations

Thoughtworks is committed to providing reasonable accommodations to…

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