Technology Advisory Engagement Lead

Thoughtworksreferral; Chicago (IL); On-site; USD 196,000 - 380,000; Full time

Job summary

Thoughtworks in Chicago seeks an Engagement Lead to guide AI-native advisory engagements, bridging strategy and working solutions. You will own delivery outcomes, structure engagements, and orchestrate AI-enabled delivery from analysis to implementation, ensuring quality and measured business impact.

You will interface with CTO/CIO and program leaders to translate recommendations into practical execution paths, while managing delivery risks and maintaining momentum across workstreams.

Qualifications

• Structured Problem Solving: break down ambiguity into clear, actionable work.
• Delivery Leadership: drive execution with focus and accountability.
• System Thinking: understand how business processes, technology, and data fit together.
• AI-Native Execution: use AI to accelerate analysis and outputs.
• Stakeholder Navigation: work across business and technology stakeholders.

Responsibilities

• Own delivery of outcomes by translating client goals into workstreams, milestones, and outputs.
• Structure and lead the engagement, breaking down complex problems into actionable components.
• Orchestrate AI-native delivery, designing AI usage across analysis, modeling, code and documentation.
• Ensure quality and coherence by reviewing outputs for logical consistency, relevance, and feasibility.
• Interface with client delivery leadership to translate advisory recommendations into practical execution paths.
• Manage risk and execution reality, identifying delivery risks early and adjusting approach as needed.
• Build reusable delivery patterns and contribute to engagement models, AI workflows, and decision frameworks.

Skills

Experience in consulting, product, or

Lead multi-disciplinary teams

Job description

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 workstreams, 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 workstreams—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.

EEO

Thoughtworks is an equal‑opportunity employer. We are committed to providing equal employment opportunities to all qualified applicants and employees without regard to race, color, religion, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, military or veteran status, or any other characteristic protected by applicable federal, state, or local law. We prohibit discrimination and harassment of any kind and are dedicated to providing a work environment free from discrimination and harassment. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, stermination, layoff, recall, transfer, leaves of absence, compensation, and training.
Thoughtworks is also an affirmative action employer of veterans and individuals with disabilities.
For additional information, please see the Thoughtworks, Inc. Equal Employment Opportunity & Aff…

US - Work Authorization

Applicants for employment in the US must have work authorization that does not now or in the future require sponsorship of a visa for employment in the United States.

Accommodations

Thoughtworks is committed to providing reasonable accommodations to qualified applicants with disabilities or sincerely held religious beliefs, practices, or observances, in accordance with applicable law.
If you need a reasonable accommodation to complete any part of the application process, participate in interviews, or otherwise engage in the hiring process, you may request an accommodation by completing this form or speaking with your recruiter. Requests may be made at any stage of the application or interview process.
Once a request is received, Thoughtworks will engage in an interactive process with the applicant to determine an appropriate accommodation. Applicants are not required to disclose medical diagnoses or detailed personal information in order to request an accommodation. All accommodation requests will be handled in a timely, confidential, and respectful manner, consistent with applicable legal requirements.
Requesting an accommodation will not negatively affect your consideration for employment. Company prohibits retaliation against any applicant for requesting an accommodation or participating in the accommodation process. Accommodations made during the recruitment process are not a guarantee of future or continued accommodations once hired. If you are hired by Thoughtworks, and require an accommodation to perform the essential functions of your role, you may be asked to engage in our reasonable accommodation process.

Cancellations

As a technology consultancy, the projects we undertake are subject to change based on client needs and agreements. While we strive for consistency, please be aware that project scope or availability may shift, or projects may even be cancelled, during the recruitment and selection process, which is often outside of our direct control. Should the project related to this vacancy be significantly altered or cancelled, all impacted candidates will be promptly and duly informed of the change

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-Hybrid

Salary

Benefits: https://www.thoughtworks.com/en-us/careers/benefits

The annual salary range posted is subject to many factors and may vary depending on experience, geographic location, job responsibilities, performance, skills and/or training.

Salary

$196,000 — $380,000 USD

See here our AI policy.