Senior AI Technical Project Manager (Chicago)
Reuben Cooley Inc.
Roles & Responsibilities
We are seeking an experienced AI Technical Project Manager to lead the delivery and portfolio governance of Generative AI, AI/ML, and AWS-based solutions . This role will oversee multiple AI initiatives, drive end-to-end project execution, and provide consolidated portfolio updates to senior leadership
Key Responsibilities
- Own and lead end-to-end delivery of GenAI and AI/ML projects from planning through production deployment.
- Manage a portfolio of AI initiatives, creating consolidated dashboards, executive reports, and program health updates.
- Coordinate with project managers, architects, data scientists, engineers, and business stakeholders to ensure successful delivery.
- Lead all Agile/Scrum ceremonies, including Sprint Planning, Daily Stand-ups, Backlog Grooming, Sprint Reviews, Demos, and Retrospectives.
- Track project scope, timelines, budgets, dependencies, risks, and deliverables.
- Proactively identify risks, develop mitigation plans, manage escalations, and remove delivery roadblocks.
- Drive stakeholder communication, executive updates, governance reviews, and leadership presentations.
- Manage cross-project dependencies, resource conflicts, and portfolio-level priorities.
Required Qualifications
- 10+ years of Technical Project Management, Program Management, or Delivery Leadership experience.
- Proven experience delivering AWS-based AI/ML and Generative AI projects .
- Good understanding of:
- Generative AI, LLMs, RAG, AI Agents, Prompt Engineering
- Machine Learning Lifecycle
- MLOps / LLMOps concepts
- AWS AI services such as Bedrock, SageMaker, Lambda, S3, OpenSearch, etc.
- Experience managing multiple concurrent projects and providing portfolio-level governance.
- Strong expertise in Agile/Scrum methodologies and facilitation of all Scrum ceremonies.
- Hands-on experience with Jira, Confluence, Azure DevOps, Microsoft Project, Smartsheet, or similar project management tools .
- Excellent communication, executive presentation, stakeholder management, and leadership skills.
- Strong risk management, planning, prioritization, and problem-solving abilities.
Preferred Qualifications
- PMP, PMI-ACP, Certified Scrum Master, or SAFe certification.
- AWS Cloud or Machine Learning certifications.
- Experience in consulting, digital transformation, or customer-facing AI program.
Ideal Candidate
A strategic AI delivery leader who can effectively engage with business executives, technical teams, product leaders, and project managers while driving successful execution of multiple AI initiatives. The individual should be capable of providing portfolio-level oversight, proactive risk management, executive reporting, and predictable delivery of enterprise GenAI and AI/ML programs.
Need folks who discuss projects with CXO/stakeholders and not delivery team
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